Arylamine compound, organic electroluminescent element and electronic equipment

Abstract

The present invention provides an arylamine compound, an organic electroluminescent element and an electronic device, the arylamine compound increases the hole mobility and improves the hole transport performance by introducing aryl to increase the distance between hydropyrene and arylamine, thereby improving the luminous efficiency of the device. The prepared organic light-emitting device is well improved in light-emitting efficiency and service life, the arylamine compound has a structure shown in a formula (1) # imgabs0 #, L1 and L2 are independently selected from a single bond, substituted or unsubstituted arylene of C6-C30 and substituted or unsubstituted heteroarylene of C3-C30, and R1, R2, R3 and R4 are independently selected from a single bond, substituted or unsubstituted arylene of C6-C30, substituted or unsubstituted heteroarylene of C3-C30, substituted or unsubstituted heteroarylene of C6-C30, substituted or unsubstituted heteroarylene of C6-C30 and substituted or unsubstituted heteroarylene of C6-C30. Ar1 and Ar2 are respectively and independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted aryl of C6-C60, and substituted or unsubstituted heteroaryl of C3-C60; r1 is selected from substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl X, Y is-CH2, n is 0 or 1, and when n is 0, connecting bonds on the two sides of X and Y do not exist.

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 element, 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 polymer or small molecule 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 is 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 luminescence efficiency and external luminescence efficiency. The internal luminescence efficiency is related to the light conversion efficiency of generating excitons 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 75%. The external luminescence efficiency is related to the light extraction efficiency of the light generated in the organic layer being emitted to the outside of the organic electroluminescent device. Generally, the external light extraction efficiency is about 20% of the internal luminescence 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 levels of the peripheral functional layers also affect the light-emitting efficiency. In order to fabricate high-efficiency and long-lifetime organic electroluminescent devices, the development of materials with high triplet energy levels and high lowest unoccupied molecular orbital (LUMO) energy levels is 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 not only be used as a high-performance light-emitting auxiliary layer material, but also be used as one or more layers of single-layer or laminated devices such as an electron blocking layer, a hole blocking layer, and a hole transport layer.

[0009] The technical solution adopted by the present invention to solve its technical problems is:

[0010] An arylamine compound having a structure represented by formula (1),

[0011]

[0012] In formula (1), L 1 and L 2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C3-C30 heteroarylene group.

[0013] Ar 1 and Ar 2 are the same or different and are each independently selected from hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted C6-C60 aryl group, or a substituted or unsubstituted C3-C60 heteroaryl group;

[0014] R 1Selected 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;

[0015] When the substituents in the "substituted or unsubstituted" are substituents, they are each independently selected from deuterium, halogen, cyano, silyl, C1-C10 alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C6-C30 aryl, C3-C30 heteroaryl,

[0016] X, Y are —CH 2 , n is 0 or 1. When n is 0, the connecting bonds on both sides of X and Y do not exist;

[0017] When the substituents in the "substituted or unsubstituted" are substituents, they are each independently selected from deuterium, halogen, cyano, silyl, C1-C10 alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C6-C30 aryl, C3-C30 heteroaryl,

[0018] In the heteroarylene, heterocycloalkyl, heteroalkenyl, and heteroaryl, the heteroatoms are each independently at least one of N, O, S, Si, and P.

[0019] Furthermore, the aromatic amine compound has the structure shown in formulas (2)-(5),

[0020]

[0021] In formulas (2)-(5), L 1 , L 2 are the same or different, and are each independently selected from a single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C3-C30 heteroarylene,

[0022] Ar 1 , Ar 2 are the same or different, and are each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl;

[0023] R 1Selected 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.

[0024] Further, L 1 and L 2 are the same or different and each independently selected from a single bond, divalent groups as follows: substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted perylenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted furyl, substituted or unsubstituted thienyl, substituted or unsubstituted indenyl, substituted or unsubstituted indolyl, substituted or unsubstituted benzofuryl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzofuryl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted carbolinyl, substituted or unsubstituted 9,9-dimethylfluorene, substituted or unsubstituted 9,9-diphenylfluorene, substituted or unsubstituted spirobifluorene.

[0025] Further, Ar 1 and Ar 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, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted perylenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted furyl, substituted or unsubstituted thienyl, substituted or unsubstituted indenyl, substituted or unsubstituted indolyl, substituted or unsubstituted benzofuryl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzofuryl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted carbolinyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirobifluorene, substituted or unsubstituted tetrahydropyrenyl.

[0026] Preferably, the Ar 1 and Ar 2Same or different, 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, anthryl, phenanthryl, fluoranthenyl, pyrenyl, perylenyl, triphenylenyl, furyl, thienyl, indenyl, indolyl, benzofuryl, benzothienyl, dibenzofuryl, dibenzothienyl, carbazolyl, carbolinyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirobifluorenyl, tetrahydropyrenyl, and phenyl-substituted naphthyl, anthryl, phenanthryl, fluoranthenyl, pyrenyl, perylenyl, triphenylenyl, furyl, thienyl, indenyl, indolyl, benzofuryl, benzothienyl, dibenzofuryl, dibenzothienyl, carbazolyl, carbolinyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirobifluorenyl, tetrahydropyrenyl.

[0027] Further, R 1 is selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted perylenyl, substituted or unsubstituted triphenylenyl.

[0028] The present invention also provides a preparation, the preparation comprising at least one of the above-mentioned arylamine compounds and at least one solvent.

[0029] The present invention also provides an organic electroluminescent device, comprising:

[0030] A first electrode;

[0031] A second electrode disposed to face the first electrode; and

[0032] One or more organic material layers disposed between the first electrode and the second electrode and including a light-emitting layer,

[0033] wherein one or more of the organic material layers contain the arylamine compound of the present invention.

[0034] In one 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.

[0035] The present invention also provides an electronic device, the electronic device including a display device and a lighting device, and having the above-mentioned organic electroluminescent device.

[0036] Generally speaking, compared with the prior art by the above technical solutions conceived by the present invention, the following beneficial effects can be achieved:

[0037] 1. The arylamine compound of the present invention increases the hole mobility and improves the hole transport performance by introducing an aryl group to increase the distance between the hydroanthracene and the arylamine, thereby improving the luminous efficiency of the device. The prepared organic light-emitting device has a good improvement in luminous efficiency and lifespan. BRIEF DESCRIPTION OF THE DRAWINGS

[0038] Figure 1 FIG. 6 is a schematic diagram of the device structure of an organic electroluminescent element according to an embodiment of the present invention, where 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 are shown. DETAILED DESCRIPTION OF THE EMBODIMENTS

[0039] Exemplary embodiments will now be described in detail, with their examples illustrated in the accompanying drawings, where 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 descriptions set forth herein. Therefore, the exemplary embodiments are described below only by reference to the accompanying 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. Expressions such as "at least one (kind) of" modify the entire list of elements when preceding or following the list of elements and do not modify individual elements of the list.

[0040] It will be understood that when an element is referred to as being "on" another element, it can be directly in 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.

[0041] 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 the present 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).

[0042] The term "or" means "and / or". It will be further understood that the terms "comprises" or "comprising", 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 other features, regions, wholes, steps, operations, elements, components, and / or their combinations.

[0043] Unless otherwise defined, all terms (including technical and scientific terms) used herein 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 that is 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.

[0044] As used herein, "about" or "approximately" includes the stated value and means within an acceptable deviation range for a particular 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 the specific quantity (i.e., the limitations of the measurement system). For example, "about" can mean within one or more standard deviation ranges of the stated value, or within the ranges of ±30%, 20%, 10%, 5%.

[0045] Exemplary embodiments are described herein with reference to cross-sectional views that are schematic illustrations of idealized embodiments. Thus, deviations from the shape of the figures are to be expected as a result of, for example, manufacturing techniques and / or tolerances. Accordingly, the embodiments described herein should not be construed as limited to the specific shapes of the regions as illustrated herein, but include deviations in shape resulting from, for example, manufacturing. For example, regions illustrated or described as flat may typically have rough and / or non-linear features. Additionally, sharp corners illustrated may be rounded. Thus, the regions illustrated in the figures are schematic in nature, and their shapes are not intended to illustrate the exact shape of the regions and are not intended to limit the scope of the claims.

[0046] The present invention will be further described below in conjunction with specific embodiments. It should be understood that these embodiments are only for illustrating the present invention and not for limiting the protection scope of the present invention. In addition, it should be understood that after reading the content disclosed by 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; the reagents, materials, etc. used in the following examples, unless otherwise specified, can all be obtained from commercial channels.

[0048] Term Explanation

[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, adamantyl, and the like.

[0052] As used in the present invention, the term "C2-C10 hetero cycloalkyl" refers to a monovalent substituent derived from a monocyclic or polycyclic group having 2 to 10 carbon atoms and containing at least one heteroatom selected from O, S, N, P, and Si in the ring.

[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 (i-propyloxy), n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, and benzyloxy.

[0054] As used in the present invention, the term "cycloalkenyl" refers to an unsaturated carbocyclic ring that is not aromatic.

[0055] As used in the present invention, the term "heterocycloalkenyl" refers to an unsaturated heterocyclic ring that is not aromatic.

[0056] As used in the present invention, the term "C6-C60 aryl" 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 side-bonded 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, removing one hydrogen atom from phenyl forms phenylene, and removing one hydrogen atom from naphthyl forms naphthylene.

[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 atom, preferably 1 to 3 carbon atoms, in the ring is replaced by a heteroatom such as N, O, S, P, B or Si. In addition, such a heteroaryl may have a form in which two or more rings are simply linked to each other or fused to each other or fused to an aryl group. Examples of such heteroaryl include pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, indolizinyl, indolyl, indolopyridyl, purinyl, phenanthrolinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, thiazolyl, imidazolyl, oxazolyl, furyl, thienyl, benzofuranyl, benzothienyl, benzothiazolyl, benzimidazolyl, benzoxazolyl, carbazolyl, dibenzofuranyl, 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 by removing one hydrogen atom.

[0060] As used in the present invention, the term "silyl" refers to a trisubstituted silyl, such as trimethylsilyl, triphenylsilyl, etc.

[0061] As used in the present invention, "carbon atom number of X - Y of Z group" or "C(X - Y) Z group" in the expression means that the carbon atom number of the Z group when it is unsubstituted, excluding the carbon atom number of the substituent when it is substituted. For example, an aryl group having 6 to 60 carbon atoms means that when it is unsubstituted, the number of carbon atoms in the aryl group is any integer from 6 to 60, that is, the number of carbon atoms when unsubstituted 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, carbazolyl, as long as it is not otherwise recorded in this specification, includes any of the following groups, but is not limited thereto,

[0063] represents the substitution position. "Unsubstituted" means retaining a hydrogen atom, and in this case, the hydrogen atom includes protium, deuterium, and tritium.

[0064] When there are two or more substituents, the two or more substituents can be the same or different.

[0065] As used in the present invention, the term "quinoline" includes

[0066] As used in the present invention, the term "terphenyl" includes

[0067] As used in the present invention, the term "benzoquinoline" includes

[0068] As used in the present invention, a hydrogen atom includes protium, deuterium, and tritium. The compounds described in the present invention may contain deuterium atoms of natural origin, 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 may be 100%, or less than 100%, or less than 95%, or less than 90%, or less than 80%. The deuteration rate may also be 1% or more, or 5% or more, or 10% or more. If the deuteration rate is not 100%, it means 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.

[0069] 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 constituent elements and do not limit the nature or order of the constituent elements corresponding to the terms.

[0070] Organic electroluminescent element

[0071] 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.

[0072] 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.

[0073] The light-emitting element of the present invention may be fluorescent light-emitting, phosphorescent light-emitting, or a combination thereof. The light-emitting element may be a single light-emitting element or a tandem type of multiple light-emitting units.

[0074] As a simple light-emitting element, the following can be cited, but are not limited thereto,

[0075] (1) Hole transport layer / fluorescent light-emitting layer / electron transport layer;

[0076] (2) Hole transport layer / phosphorescent light-emitting layer / electron transport layer;

[0077] (3) Hole transport layer / first fluorescent light-emitting layer / second fluorescent light-emitting layer / electron transport layer;

[0078] (4) Hole transport layer / First phosphorescent light-emitting layer / Second phosphorescent light-emitting layer / Electron transport layer;

[0079] (5) Hole transport layer / Fluorescent light-emitting layer / Spacer layer / Phosphorescent light-emitting layer / Electron transport layer;

[0080] (6) Hole transport layer / Electron blocking layer / Fluorescent light-emitting layer / Electron transport layer;

[0081] (7) Hole transport layer / Electron blocking layer / Fluorescent light-emitting layer / Hole blocking layer / Electron transport layer;

[0082] (8) Hole transport layer / Electron blocking layer / Phosphorescent light-emitting layer / Electron transport layer;

[0083] (9) Hole transport layer / Electron blocking layer / Phosphorescent light-emitting layer / Hole blocking layer / Electron transport layer;

[0084] (10) Hole injection layer / Hole transport layer / Phosphorescent light-emitting layer / Electron transport layer / Electron injection layer;

[0085] (11) Hole injection layer / Hole transport layer / Fluorescent light-emitting layer / Electron transport layer / Electron injection layer;

[0086] (12) Hole injection layer / Hole transport layer / Electron blocking layer / Phosphorescent light-emitting layer / Electron transport layer / Electron injection layer;

[0087] (13) Hole injection layer / Hole transport layer / Electron blocking layer / Fluorescent light-emitting layer / Electron transport layer / Electron injection layer;

[0088] The above phosphorescent / fluorescent light-emitting layers can each emit light of different colors.

[0089] 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 connection layer, etc. For example, when stacking a fluorescent light-emitting layer and a phosphorescent light-emitting layer, in order to prevent the 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.

[0090] 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.

[0091] The organic electroluminescent device of this 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).

[0092] As a cathode material, a material with a low work function is usually used to facilitate electron injection into the organic material layer.

[0093] The hole injection layer is a layer that injects holes from the electrode and has the ability to transport holes.

[0094] 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 is appropriately a material with a high hole mobility that can receive holes from the anode or the hole injection layer and transfer the holes to the light-emitting layer.

[0095] The light-emitting material is a material that can receive holes and electrons from the hole transport layer and the electron transport layer respectively and combine the holes and electrons to emit light in the visible light region. The light-emitting layer material includes a host material and a dopant material.

[0096] 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 is a material with a high electron mobility that can receive electrons from the cathode and transfer the electrons to the light-emitting layer.

[0097] The electron injection layer is a layer that injects electrons from the electrode.

[0098] The hole blocking layer is a layer that blocks holes from reaching the cathode.

[0099] The electron blocking layer is a layer that blocks electrons from reaching the anode.

[0100] Depending on the materials used, the organic light-emitting device of this specification can be a top-emitting device, a bottom-emitting device, or a dual-emission type device.

[0101] The charge generation layer refers to an intermediate layer located 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.

[0102] The core of the present invention is to provide an arylamine compound having the structure shown in formula (1).

[0103]

[0104] In formula (1), L 1 and L 2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C3-C30 heteroarylene group.

[0105] Ar 1 and Ar 2Same or different, each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl;

[0106] R 1 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 heterocycloalkenyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl;

[0107] When substituted in the "substituted or unsubstituted", 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,

[0108] X, Y are —CH 2 , n is 0 or 1, when n is 0, the connecting bonds on both sides of X and Y do not exist;

[0109] The heteroatoms in the heteroarylene, heterocycloalkyl, heterocycloalkenyl, and heteroaryl are each independently at least one of N, O, S, Si, and P.

[0110] The specific scheme is: The above-mentioned arylamine compound of the present invention includes the following structure:

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123] Those skilled in the art can synthesize the compounds of the present invention with reference to the synthesis of the following compounds and known synthesis methods. The synthesis methods of the present invention are only exemplary, and the compounds obtained by replacing the reactants with commercial raw materials or methods of the prior art are also included within the scope of this application.

[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 2-bromopyrene (42 g, 149.4 mmol) in ethyl acetate (500 mL), then add Raney nickel (20 g) and react at room temperature for 48 hours. After confirming the completion of the reaction, remove the catalyst using a diatomaceous earth column, add Pd / C (10 g) catalyst, and carry out a 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 silica gel column to obtain pure 2-bromo-4,5,9,10-tetrahydrobenzopyrene (35.7 g, yield 83%).

[0129] LC-MS (APCI): 285.82 (M+H + )

[0130] (2) Add 2-bromo-4,5,9,10-tetrahydrobenzopyrene (12.0 g, 42.1 mmol) and compound (4-bromophenyl)boronic acid (8.9 g, 44.3 mmol) to a four-necked flask, add toluene (70 mL), ethanol (30 mL), water (30 mL), potassium carbonate (11.61 g, 84.2 mmol), add tetrakis(triphenylphosphine)palladium(0) (0.97 g, 8.4 mmol), then displace with nitrogen three times, heat and stir for 3 hours. After the reaction is terminated, cool the obtained product to room temperature, wash with water, dry the organic layer over anhydrous magnesium sulfate, and then filter and concentrate. Purification can be carried out by column chromatography or distillation to obtain the intermediate compound 2-(4-bromophenyl)-4,5,9,10-tetrahydrobenzopyrene (13.7 g, yield: 90%).

[0131] LC-MS (APCI): 361.26 (M+H + )

[0132] (3) The intermediate compound 2-(4-bromophenyl)-4,5,9,10-tetrahydropyrene (13.7 g, 37.9 mmol) and [1,1'-biphenyl]-4-amine were completely dissolved in 105 mL of xylene. Then, NaOtBu (4.17 g, 43.38 mmol) was added. After adding bis(tri-tert-butylphosphine)palladium(0) (0.16 g, 3.1 mmol), the mixture was heated and stirred for 3 hours. After the reaction was terminated, the resulting product was cooled to room temperature and extracted with distilled water and ethyl acetate. The organic layer was dried over MgSO 4 and filtered and concentrated. Using ethyl acetate and n-hexane as the eluent, the concentrated residue was purified by column chromatography to obtain the intermediate compound N-(4-(tetrahydropyrene-2-yl)phenyl)-[1,1'-biphenyl]-4-amine (14.9 g, yield 88%).

[0133] LC-MS (APCI): 450.61 (M+H + )

[0134] (4) The obtained intermediate compound N-(4-(4,5,9,10-tetrahydropyrene-2-yl)phenyl)-[1,1'-biphenyl]-4-amine (14.9 g, 30.10 mmol) and 2-bromo-9,9-dimethyl-9H-fluorene (9.05 g, 33.1 mmol) were added to a 500 mL four-necked flask. After adding bis(tri-tert-butylphosphine)palladium(0) (0.15 g, 3.0 mmol), the mixture was heated and stirred for 3 hours. The temperature was then lowered to room temperature and the reaction was refluxed for 6 h. After cooling to room temperature, sufficient dichloromethane was added to completely dissolve the mixture. It was passed through a small amount of silica gel funnel to remove the catalyst and salts. The filtrate was concentrated to a viscous state and purified by column chromatography to obtain compound 1-1 (19.1 g, yield: 81%).

[0135] LC-MS (APCI): 642.36 (M+H + )

[0136] Synthesis Example 2:

[0137] Preparation of Compound 1-18

[0138] Prepared according to the same synthesis method as that of Structural Formula 1-1 above, except that compound b was replaced with 4-amino-9,9-spirobifluorene, to obtain the compound of Structural Formula 1-18 (40.09 g, yield 80%).

[0139] LC-MS (APCI): 804.36 (M+H + )

[0140] Synthesis Example 3:

[0141] Preparation of Compound 1-35

[0142] Prepared according to the same synthesis method as the above Structural Formula 1-1, except that compound b was replaced with 9,9'-spirobi[fluorene]-2-amine and compound c was replaced with 4-bromodibenzofuran, to obtain the compound of Structural Formula 1-35 (39.05 g, yield 73%).

[0143] LC-MS(APCI): 778.59(M+H + )

[0144] Synthesis Example 4:

[0145] Preparation of Compound 1-51

[0146] Prepared according to the same synthesis method as the above Structural Formula 1-1, except that compound b was replaced with 4-(dibenzo[b,d]thiophen-4-yl)aniline and compound c was replaced with 9-(3-bromophenyl)carbazole, to obtain the compound of Structural Formula 1-51 (39.70 g, yield 79%).

[0147] LC-MS(APCI): 797.78(M+H + )

[0148] Synthesis Example 5:

[0149] Preparation of Compound 2-8

[0150] Prepared according to the same synthesis method as the above Structural Formula 1-1, except that compound b was replaced with 9,9'-spirobi[fluorene]-2-amine and compound c was replaced with m-bromobiphenyl, to obtain the compound of Structural Formula 2-8 (38.12 g, yield 77%).

[0151] LC-MS(APCI): 764.54(M+H + )

[0152] Synthesis Example 6:

[0153] Preparation of Compound 2-20

[0154] Prepared according to the same synthesis method as the above Structural Formula 1-1, except that compound b was replaced with 9,9'-spirobi[fluorene]-4-amine, compound 1-1-1 was replaced with compound 1-bromopyrene, and compound c was replaced with compound 1-1-2, to obtain the compound of Structural Formula 2-20 (43.54 g, yield 88%).

[0155] LC-MS(APCI): 816.44(M+H + )

[0156] Synthesis Example 7:

[0157] Preparation of Compound 3-2

[0158] Prepared according to the same synthesis method as Structural Formula 1-1 above, except that Compound 1-1-1 was replaced with Compound 2-bromophenanthrene, and Compound b was replaced with 3-aminobiphenyl, to obtain the compound of Structural Formula 3-2 (40.56 g, yield 79%).

[0159] LC-MS (APCI): 616.31 (M+H + )

[0160] Synthesis Example 8:

[0161] Preparation of Compound 3-21

[0162] Prepared according to the same synthesis method as Structural Formula 1-1 above, except that Compound 1-1-1 was replaced with Compound 2-bromophenanthrene, Compound b was replaced with 9,9'-spirobi[fluorene]-4-amine, and Compound c was replaced with Compound 1-1-2, to obtain the compound of Structural Formula 3-21 (41.62 g, yield 86%).

[0163] LC-MS (APCI): 790.76 (M+H + )

[0164] Synthesis Example 9:

[0165] Preparation of Compound 3-40

[0166] Prepared according to the same synthesis method as Structural Formula 1-1 above, except that Compound 1-1-1 was replaced with Compound 2-bromophenanthrene, Compound b was replaced with 9,9'-spirobi[fluorene]-4-amine, and Compound c was replaced with 3-bromodibenzofuran, to obtain the compound of Structural Formula 3-40 (40.93 g, yield 72%).

[0167] LC-MS (APCI): 754.26 (M+H + )

[0168] Synthesis Example 10:

[0169] Preparation of Compound 3-56

[0170] Prepared according to the same synthesis method as Structural Formula 1-1 above, except that Compound 1-1-1 was replaced with Compound 3-bromophenanthrene, and Compound c was replaced with 2-(4-bromophenyl)naphthalene, to obtain the compound of Structural Formula 3-56 (41.13 g, yield 81%).

[0171] LC-MS (APCI): 626.24 (M+H + )

[0172] 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.

[0173] The following application examples further illustrate the application of the arylamine compounds described in the present invention in organic electroluminescent devices.

[0174] This embodiment 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.

[0175] Comparative Example 1

[0176] Evaporate HATCN on the ITO substrate to form a first hole injection layer (HIL) with a thickness of , evaporate HT on the above first hole injection layer to form a hole transport layer (HTL) with a thickness of , evaporate EB on the above hole transport layer to form a light-emitting auxiliary layer (EBL) with a thickness of , evaporate GH + GD (3 wt%) on the light-emitting auxiliary layer to form a light-emitting layer (EML) with a thickness of , sequentially evaporate an electron transport layer (ETL) with a thickness of , evaporate Al (with a thickness of ) to form a cathode, thereby manufacturing an organic electroluminescent device.

[0177] The structural formula of the device involved is as follows:

[0178]

[0179] Comparative Example 2

[0180] Prepare the organic electroluminescent device of Comparative Example 2 by the same method as in the embodiment of Comparative Example 1, except that the light-emitting auxiliary layer (EB) is replaced by compound EB-1 instead of compound EB in the embodiment of Comparative Example 1.

[0181] Comparative Example 3

[0182] Prepare the organic electroluminescent device of Comparative Example 3 by the same method as in the embodiment of Comparative Example 1, except that the light-emitting auxiliary layer (EB) is replaced by compound EB-2 instead of compound EB in the embodiment of Comparative Example 1.

[0183] Device Example 1

[0184] Prepare the organic electroluminescent device of Device Example 1 by the same method as in the embodiment of Comparative Example 1, except that the light-emitting auxiliary layer (EB) is replaced by compound 1-1 instead of compound EB in the embodiment of Comparative Example 1.

[0185] Device Example 2

[0186] The organic electroluminescent device of Device Example 2 was prepared by the same method as in the implementation scheme of Comparative Example 1 above, except that the light-emitting auxiliary layer (EB) was replaced by Compound 1-18 from Compound EB.

[0187] Device Example 3

[0188] The organic electroluminescent device of Device Example 3 was prepared by the same method as in the implementation scheme of Comparative Example 1 above, except that the light-emitting auxiliary layer (EB) was replaced by Compound 1-35 from EB.

[0189] Device Example 4

[0190] The organic electroluminescent device of Device Example 4 was prepared by the same method as in the implementation scheme of Comparative Example 1 above, except that the light-emitting auxiliary layer (EB) was replaced by Compound 1-51 from Compound EB.

[0191] Device Example 5

[0192] The organic electroluminescent device of Device Example 5 was prepared by the same method as in the implementation scheme of Comparative Example 1 above, except that the light-emitting auxiliary layer (EB) was replaced by Compound 2-8 from Compound EB.

[0193] Device Example 6

[0194] The organic electroluminescent device of Device Example 6 was prepared by the same method as in the implementation scheme of Comparative Example 1 above, except that the light-emitting auxiliary layer (EB) was replaced by Compound 2-20 from Compound EB in the implementation scheme of Comparative Example 1.

[0195] Device Example 7

[0196] The organic electroluminescent device of Device Example 7 was prepared by the same method as in the implementation scheme of Comparative Example 1 above, except that the light-emitting auxiliary layer (EB) was replaced by Compound 3-2 from Compound EB1 in the implementation scheme of Comparative Example 1.

[0197] Device Example 8

[0198] The organic electroluminescent device of Device Example 8 was prepared by the same method as in the implementation scheme of Comparative Example 1 above, except that the light-emitting auxiliary layer (EB) was replaced by Compound 3-21 from Compound EB in the implementation scheme of Comparative Example 1.

[0199] Device Example 9

[0200] The organic electroluminescent device of Device Example 9 was prepared by the same method as the implementation scheme of Comparative Example 1 above, except that the light-emitting auxiliary layer (EB) was replaced with Compound 3-40 instead of Compound EB in the implementation scheme of Comparative Example 1.

[0201] Device Example 10

[0202] The organic electroluminescent device of Device Example 10 was prepared by the same method as the implementation scheme of Comparative Example 1 above, except that the light-emitting auxiliary layer (EB) was replaced with Compound 3-56 instead of Compound EB in the implementation scheme of Comparative Example 1.

[0203] Evaluation of Organic Electroluminescent Element

[0204] 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: hour)) was measured. Taking the lifetime of Comparative Example 1 as 100%, the relative lifetime values of each comparative example and example with respect to Comparative Example 1 were obtained.

[0205] 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 with respect to Comparative Example 1 were obtained.

[0206] 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 with respect to Comparative Example 1 were obtained. The test results are shown in Table 1.

[0207] Table 1

[0208]

[0209] 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 light-emitting auxiliary layer, the driving voltage is reduced compared with the comparative examples, 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.

[0210] 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), In formula (1), L 1 , 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, Ar 1 、Ar 2 are the same or different and each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl; R 1 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; 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, X and Y are —CH 2 , n is 0 or 1. When n is 0, the connecting bonds on both sides of X and Y do not exist; in the heteroarylene, heterocycloalkyl, heterocycloalkenyl, heteroaryl, the heteroatoms are each independently at least one of N, O, S, Si, P.

2. The aromatic amine compound according to claim 1, characterized in that, the aromatic amine compound has the structures shown in formula (2)-(5), In formulas (2)-(5), 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. Ar 1 、Ar 2 are the same or different and each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl; R 1 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.

3. The aromatic amine compound according to claim 1, characterized in that, L 1 and L 2 are the same or different and each independently selected from a single bond and divalent groups as follows: substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted perylenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted indenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted carbolinyl, substituted or unsubstituted 9,9-dimethylfluorene, substituted or unsubstituted 9,9-diphenylfluorene, substituted or unsubstituted spirobifluorenyl.

4. The aromatic amine compound according to claim 1, characterized in that, Ar 1 、Ar 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, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted perylenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted furyl, substituted or unsubstituted thienyl, substituted or unsubstituted indenyl, substituted or unsubstituted indolyl, substituted or unsubstituted benzofuryl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzofuryl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted carbolinyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted tetrahydropyrenyl.

5. The aromatic amine compound according to claim 1, characterized in that, R 1 selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted perylenyl, and substituted or unsubstituted triphenylenyl.

6. The aromatic amine compound according to claim 1, characterized in that, the aromatic amine compound includes the following structure:

7. A preparation, characterized in that, the preparation contains at least one aromatic amine compound according to any one of claims 1-6 and at least one solvent.

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 layers of the organic material layer contain the aromatic amine compound according to any one of claims 1-6.

9. The 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 1-6.

10. An electronic device, characterized in that, the electronic device is provided with the organic electroluminescent element according to claim 9.

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