An arylamine compound and an organic electroluminescence device thereof

Abstract

The application provides an arylamine compound and an organic electroluminescent device thereof, and particularly relates to the technical field of organic electroluminescent materials. In view of the problems of poor carrier matching of existing hole transport materials, weak electron blocking ability, insufficient compactness and anti-aging performance of the covering layer material thin film, single function, low light-emitting efficiency of the device, poor stability and short service life, a new arylamine compound is developed. The compound has excellent performance, can effectively balance the carrier transport, reduce the power consumption of the device, improve the carrier recombination efficiency and the thin film stability, can also inhibit the non-radiation loss of the interface exciton, isolate the water vapor and oxygen erosion, effectively make up the performance short board of the traditional photoelectric material, and when the compound is applied to the organic electroluminescent device, the light-emitting efficiency of the device can be significantly improved, and the service life of the device can be prolonged.

Description

Technical Field

[0001] This invention relates to the field of organic electroluminescent materials technology, specifically to an aromatic amine compound and its organic electroluminescent device. Background Technology

[0002] Organic light-emitting diodes (OLEDs) have been widely used in the display and lighting fields due to their advantages such as self-emission, low power consumption, high response speed, and flexible fabrication. With the continuous iteration and development of high-end flexible display devices, the industry's requirements for the luminous efficiency, operational stability, and lifespan of OLED devices are constantly increasing. High-performance, multifunctional organic optoelectronic materials have become the key to breaking through the performance bottlenecks of these devices.

[0003] OLED devices rely on an electric field to drive carrier recombination for light emission. Under an applied voltage, holes in the anode and electrons in the cathode migrate to the light-emitting layer and recombine to form excitons, which then emit light through exciton radiative transitions. The hole transport layer is responsible for hole conduction and electron blocking, while the capping layer plays a role in energy level regulation, interface protection, suppressing exciton quenching, and blocking water vapor and oxygen erosion. The combined performance of the two layers directly determines the overall photoelectric performance and service stability of the device.

[0004] Current materials generally have significant defects. Traditional hole transport materials have poor carrier matching and weak electron blocking ability, which easily leads to carrier leakage, resulting in high driving voltage and low recombination efficiency. Conventional capping layer materials have poor energy level adaptability, insufficient film density, and weak anti-aging ability, and cannot effectively suppress interfacial exciton loss and external environmental erosion. Moreover, existing materials have limited functions. Therefore, it is necessary to develop high-performance organic electroluminescent materials to solve the above problems. Summary of the Invention

[0005] To address the issue of low performance in existing organic electroluminescent devices, this invention provides an aromatic amine compound and its organic electroluminescent device.

[0006] This invention provides an aromatic amine compound having the structure shown in Formula 1.

[0007] Wherein, Ar1 is selected from one or more R4-substituted groups of the following: aryl of C6 to C30, heteroaryl of C2 to C30, fused cycloalcoholic group of C3 to C30 aliphatic ring and C6 to C30 aromatic ring, fused cycloalcoholic group of C3 to C30 aliphatic ring and C2 to C30 heteroaromatic ring; At least one of the R4 groups is selected from an F-substituted alkyl group, and the remainder is selected from any one of hydrogen, deuterium, fluorine, cyano, substituted or unsubstituted silyl group, substituted or unsubstituted C1-C25 alkyl group, substituted or unsubstituted C3-C25 cycloalkyl group, substituted or unsubstituted C1-C25 heterocycloalkyl group, substituted or unsubstituted C6-C30 aryl group, and substituted or unsubstituted C2-C30 heteroaryl group. The Ar2 is selected from one or more R5-substituted groups of the following: aryl of C6 to C30, heteroaryl of C2 to C30, fused cycloalcoholic group of C3 to C30 aliphatic ring and C6 to C30 aromatic ring, and fused cycloalcoholic group of C3 to C30 aliphatic ring and C2 to C30 heteroaromatic ring. At least one of R5 is selected from F or an F-substituted alkyl group, and the remainder is selected from any one of hydrogen, fluorine, deuterium, silicon, cyano, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl. The Ar3, Ar4, Ar5, and Ar6 are independently selected from any one of the following: substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, fused cycloalcoholic groups of substituted or unsubstituted C3-C30 aliphatic rings and C6-C30 aromatic rings, and fused cycloalcoholic groups of substituted or unsubstituted C3-C30 aliphatic rings and C2-C30 heteroaromatic rings. R1, R2, and R3 are independently selected from any one of hydrogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 aliphatic ring, and fused cycloyl group of C6-C30 aromatic ring, and at least one of R1, R2, and R3 is not hydrogen; The L1, L2, L3, L4, L5, L6, L7, L8, and L9 are independently selected from any one of the following: single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted C3-C30 aliphatic ring and C6-C30 aromatic ring, substituted or unsubstituted C3-C30 aliphatic ring and C2-C30 heteroaromatic ring, and combinations thereof.

[0008] The present invention also provides an organic electroluminescent device, comprising an anode, an organic layer, and a cathode, wherein the organic layer is located between the anode and the cathode or outside either the anode or the cathode, and the organic layer comprises at least one of the aromatic amine compounds.

[0009] Beneficial effects: The aromatic amine compound provided by this invention, when applied to organic electroluminescent devices, can effectively improve the luminous efficiency and lifespan of the devices. When used as a hole transport layer, the compound can balance carrier transport, suppress electron leakage, reduce device energy consumption, and improve film stability. When used as a capping layer material, it can effectively suppress interfacial exciton nonradiative loss, isolate water vapor and oxygen erosion, and improve the film interface state, thereby further enhancing the performance of the devices. Detailed Implementation

[0010] The technical solutions of this invention will be clearly and completely described below with reference to specific embodiments. Obviously, the described embodiments are only some embodiments of this invention, and not all embodiments. Based on the embodiments of this invention, all other embodiments obtained by those skilled in the art without creative effort are within the protection scope of this invention.

[0011] In the compounds of this invention, any atom not specified as a particular isotope includes any stable isotope of that atom, and includes atoms at both their natural and non-natural isotopic abundances. In this invention, "H," "hydrogen," and "hydrogen atom" refer to isotopes with different numbers of neutrons, including protium, deuterium, and tritium.

[0012] In this specification, " "This refers to the portion that is connected to another substituent."

[0013] In this specification, when the position of the substituent on the ring is not fixed, it means that it can be attached to any of the corresponding optional sites on the ring. For example, Can represent , , ; Can represent , , ; Can represent , , , , , , , , , And so on.

[0014] In this specification, when a substituent or linking site lies within a bond that extends through two or more rings, it indicates that the substituent or linking site can be linked to any one of the two or more rings, specifically to any one of the corresponding optional sites within the rings. For example, Can represent or ; Can represent , , And so on.

[0015] Examples of halogen atoms described in this invention may include fluorine, chlorine, bromine, or iodine.

[0016] The "substituted or unsubstituted silyl group" mentioned in this invention refers to —Si(R k )3 groups, wherein each R k The same or different groups are selected from the following: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 aliphatic ring and C6-C30 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 aliphatic ring and C2-C30 heteroaromatic ring. Preferably, each R e The same or different groups are selected from the following: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C30 aryl. The alkyl group preferably has 1 to 25 carbon atoms, more preferably 1 to 15, even more preferably 1 to 8, and most preferably 1 to 6. The cycloalkyl group preferably has 3 to 25 carbon atoms, more preferably 3 to 15, even more preferably 3 to 10. The aryl group preferably has 6 to 30 carbon atoms, more preferably 6 to 18, and particularly preferably 6 to 12. Preferably, each R... kThe same or different groups are selected from the following: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted heptyl, substituted or unsubstituted octyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl. Preferably, the "substituted or unsubstituted C3-C25 silyl" refers to a silyl group substituted with a substituted or unsubstituted C3-C25 alkyl or aryl group, preferably substituted with 3 alkyl or 3 aryl groups. Examples of “substituted or unsubstituted silyl groups”, especially “substituted or unsubstituted C3-C25 silyl groups”, may include, but are not limited to, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, triphenylsilyl, etc.

[0017] The alkyl group described in this invention refers to a monovalent group obtained by removing one hydrogen atom from an alkane molecule. It can be a straight-chain alkyl group or a branched-chain alkyl group, preferably having 1 to 25 carbon atoms, more preferably 1 to 15 carbon atoms, more preferably 1 to 8 carbon atoms, and particularly preferably 1 to 6 carbon atoms. The alkyl group can be substituted or unsubstituted. Specific examples may include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, etc., but are not limited thereto.

[0018] The cycloalkyl group described in this invention refers to a monovalent group obtained by removing one hydrogen atom from a cyclic alkane molecule, preferably with 3 to 25 carbon atoms, more preferably with 3 to 15 carbon atoms, and particularly preferably with 3 to 10 carbon atoms. The cycloalkyl group can be substituted or unsubstituted. The cycloalkyl group includes, but is not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, etc.

[0019] The heterocyclic alkyl group described in this invention refers to a group formed by replacing one or more carbon atoms in a cyclic alkane molecule with heteroatoms. These heteroatoms include, but are not limited to, O, S, N, Si, or P atoms, preferably 1 to 25 carbon atoms, more preferably 2 to 15 carbon atoms, and particularly preferably 2 to 10 carbon atoms. The linking site of the heterocyclic alkyl group can be located on a cyclic carbon atom or on a cyclic heteroatom. The heterocyclic alkyl group can be a monocyclic heterocyclic alkyl group, a polycyclic heterocyclic alkyl group, or a fused-ring heterocyclic alkyl group. The heterocyclic alkyl group can be substituted or unsubstituted. The heterocyclic alkyl group includes, but is not limited to, heterocyclic propyl, heterocyclic butyl, heterocyclic pentyl, heterocyclic hexyl, and heterocyclic heptyl groups.

[0020] The aryl group described in this invention refers to a monovalent group obtained by removing a hydrogen atom from the aromatic carbon atom of an aromatic compound molecule. It can be a monocyclic aryl, polycyclic aryl, or fused-ring aryl, preferably having 6 to 30 carbon atoms, more preferably 6 to 18 carbon atoms, and particularly preferably 6 to 12 carbon atoms. The aryl group can be substituted or unsubstituted. The monocyclic aryl group refers to an aryl group with only one aromatic ring in the molecule, such as phenyl, but not limited to this; the polycyclic aryl group refers to an aryl group with two or more independent aromatic rings in the molecule, such as biphenyl, terphenyl, tetraphenyl, etc., but not limited to this; the fused-ring aryl group refers to an aryl group with two or more aromatic rings in the molecule that are fused together by sharing two adjacent carbon atoms, such as naphthyl, anthracene, phenanthrene, pyrene, peryl, thionyl, triphenylene, fluoranthyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, benzo[a]fluorenyl, 9,9'-spirodifluorenyl, etc., but not limited to this.

[0021] The heteroaryl group described in this invention refers to a group obtained by replacing one or more aromatic carbon atoms in an aryl group with heteroatoms. The heteroatoms include, but are not limited to, O, S, N, Si, or P atoms, and preferably have 2 to 30 carbon atoms, particularly preferably 2 to 18 carbon atoms, and most preferably 2 to 12 carbon atoms. The linking site of the heteroaryl group can be located on a cyclic carbon atom or on a cyclic heteroatom. The heteroaryl group can be a monocyclic heteroaryl, polycyclic heteroaryl, or fused-ring heteroaryl. The heteroaryl group can be substituted or unsubstituted. The monocyclic heteroaryl groups include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thiopheneyl, pyrroleyl, oxazolyl, thiazolyl, imidazolyl, etc., but are not limited thereto; the polycyclic heteroaryl groups include bipyridyl, bipyrimidinyl, phenylpyridyl, phenylpyrimidinyl, etc., but are not limited thereto; the fused-ring heteroaryl groups include quinolinyl, isoquinolinyl, benzo[a]quinolinyl, benzo[a]isoquinolinyl, quinazolinyl, quinoxalinyl, benzo[a] ... Phinyl, o-phenanthroline, naphthidyl, indolyl, benzothiopheneyl, benzofuranyl, benzooxazolyl, benzoimidazolyl, benzothiazolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothiopheneyl, benzodibenzothiopheneyl, dibenzooxazolyl, dibenzoimidazolyl, dibenzothiazolyl, carbazoleyl, benzocarbazoleyl, acridineyl, phenoxazinyl, phenthiaazinyl, phenoxthiayl, spirofluorenexanthraceneyl, spirofluorenethixanthraceneyl, etc., but not limited to these.

[0022] The aliphatic rings described in this invention refer to cyclic hydrocarbons with aliphatic properties, containing closed carbon rings in the molecule, preferably with 3 to 30 carbon atoms, more preferably 3 to 15 carbon atoms, even more preferably 3 to 12 carbon atoms, and even more preferably 3 to 7 carbon atoms. They can form monocyclic or polycyclic hydrocarbons, and can be completely unsaturated or partially unsaturated. Examples include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopropylene, cyclobutene, cyclopentene, cyclohexene, cycloheptene, etc., but are not limited to these. Multiple monocyclic hydrocarbons can also be linked in various ways: two rings in the molecule can share a carbon atom to form a spiro ring; two carbon atoms on the ring can be connected by a carbon bridge to form a bridged ring; several rings can also be interconnected to form a cage-like structure.

[0023] The fused cyclic group of aliphatic and aromatic rings described in this invention refers to a molecule containing one or more aromatic rings and one or more aliphatic rings fused together by sharing two adjacent carbon atoms. The aromatic ring preferably has 6 to 30 carbon atoms, more preferably 6 to 18 carbon atoms, and most preferably 6 to 12 carbon atoms. The aliphatic ring preferably has 3 to 30 carbon atoms, more preferably 3 to 15 carbon atoms, more preferably 3 to 10 carbon atoms, and most preferably 3 to 7 carbon atoms. The fused cyclic group of aromatic and aliphatic rings can be substituted or unsubstituted. Examples include benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, naphthocyclopropane, naphthocyclobutane, naphthocyclopentane, naphthocyclohexane, naphthocyclopentenyl, naphthocyclohexenyl, etc., but are not limited thereto.

[0024] The fused cyclic group of aliphatic and heteroaromatic rings mentioned in this invention refers to a monovalent group formed by removing a hydrogen atom after the aliphatic ring and the heteroaromatic ring are fused together. Preferably, it has 5 to 30 carbon atoms, more preferably 5 to 18 carbon atoms, and most preferably 5 to 12 carbon atoms. Examples include, but not limited to, dibenzofuranocyclopropyl, dibenzofuranocyclobutyl, dibenzofuranocyclopentyl, dibenzofuranocyclohexyl, dibenzofuranocycloheptyl, dibenzothiophenecyclopropyl, dibenzothiophenecyclobutyl, dibenzothiophenecyclopentyl, dibenzothiophenecyclohexyl, dibenzothiophenecycloheptyl, carbazocyclopropyl, carbazocyclobutyl, carbazocyclopentyl, carbazocyclohexyl, carbazocycloheptyl, pyridinocyclopropyl, pyridinocyclobutyl, pyridinocyclopentyl, pyridinocyclohexyl, pyridinobenzocycloheptyl, pyrimidinocyclopropyl, pyrimidinocyclobutyl, pyrimidinocyclopentyl, pyrimidinocyclohexyl, pyrimidinobenzocycloheptyl, etc.

[0025] The arylene group described in this invention refers to the general term for the divalent group remaining after removing two hydrogen atoms from the aromatic carbon atom of an aromatic hydrocarbon molecule. It can be a monocyclic arylene, a polycyclic arylene, or a fused-ring arylene, preferably having 6 to 30 carbon atoms, more preferably 6 to 22 carbon atoms, even more preferably 6 to 18 carbon atoms, and most preferably 6 to 12 carbon atoms. Regarding the aforementioned arylene groups, monocyclic arylene groups can be phenylene, etc., but are not limited to these. The arylene group can be substituted or unsubstituted. Polycyclic arylene groups can be biphenylene, terphenylene, tetraphenylene, etc., but are not limited to these. Fused-ring arylene groups can be naphthylene, anthraceneene, phenanthrene, pyrene, fluorene, spirofluorene, triphenylene, perylene, fluorenyl, phenanthrene, etc., but are not limited to these.

[0026] The heteroaryl group described in this invention refers to the general term for a divalent group formed by removing two hydrogen atoms from the nucleus carbon of an aromatic heterocycle composed of carbon and heteroatoms. The heteroatoms can be one or more of N, O, S, Si, and P, and can be monocyclic heteroaryl, polycyclic heteroaryl, or fused-ring heteroaryl. Preferably, it has 2 to 30 carbon atoms, more preferably 2 to 22 carbon atoms, even more preferably 2 to 20 carbon atoms, and most preferably 3 to 12 carbon atoms. The heteroaryl group can be substituted or unsubstituted. Examples may include, but are not limited to, pyridinyl, pyrazinyl, pyridazinyl, triazinyl, thiopheneyl, pyrroloyl, furanyl, pyranyl, oxazolyl, thiazolyl, imidazolyl, benzoxazolyl, benzothiazolyl, benzoimidazolyl, carbazolyl, benzocarbazolyl, acridineyl, imoxazanyl, thionazanyl, phenazinyl, phenthiazolyl, phenoxazinyl, indolyl, quinolinyl, isoquinolinyl, benzothiopheneyl, benzofuranyl, dibenzofuranyl, dibenzothiopheneyl, quinoxolinyl, quinoxolinyl, naphthinyl, purineyl, and phenanthrolineyl.

[0027] The fused aliphatic and aromatic ring groups described in this invention refer to fused ring groups of aromatic and aliphatic rings with two linking sites, i.e., divalent groups. Apart from being divalent groups, they are subject to the above description of fused ring groups of aromatic and aliphatic rings.

[0028] The fused cyclic group of aliphatic and heteroaromatic rings described in this invention refers to a fused cyclic group of a heteroaromatic or aliphatic ring with two linking sites, i.e., divalent groups. Apart from being divalent groups, they are similar to the fused cyclic groups of heteroaromatic and aliphatic rings described above.

[0029] In this invention, "unsubstituted" in "substituted or unsubstituted" means that the hydrogen atom on the group is not substituted by any substituent; "substituted" means that at least one hydrogen atom on the group is substituted by a substituent, and the position of substitution is not limited. When multiple hydrogen atoms are substituted by multiple substituents, the multiple substituents may be the same or different.

[0030] The substituents described in the "substituted or unsubstituted" of this invention may be the same as or different from each other, and are selected from deuterium, cyano, nitro, trifluoromethyl, halogen atoms, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C2-C15 alkenyl, substituted or unsubstituted C3-C18 cycloalkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C2-C18 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C6-C The fused ring group consists of any one of an aromatic ring of C3-C30 and an aliphatic ring of C3-C30, preferably deuterium, cyano, halogen atom, trifluoromethyl, C1-C5 alkyl, C3-C5 cycloalkyl, C3-C25 silyl, C6-C30 aryl, or C2-C30 heteroaryl. Specific examples may include deuterium, fluorine, chlorine, bromine, iodine, cyano, trifluoromethyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated isopropyl, deuterated tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, etc. Norbornel, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, phenyl, biphenyl, terphenyl, tolyl, pentadeuterated phenyl, naphthyl, anthracene, phenanthrene, pyrene, triphenylene, phenylyl, peryl, acenaphthene, fluoranyl, tetrabenzoyl, pentabenzoyl, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, spirofluorenyl, carbazole, 9-phenylcarbazole, 9,9'-spirodifluorenyl, benzocyclopropane, benzocyclobutane, benzocyclopropane Cyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, pyrroleyl, furanyl, thiopheneyl, benzofuranyl, benzothiopheneyl, benzopyrroleyl, dibenzofuranyl, dibenzothiopheneyl, pyridyl, pyrimidinyl, pyrazinyl, pyrazinyl, triazinyl, oxazolyl, thiazolyl, imidazolyl, benzooxazolyl, benzothiazolyl, benzotriazolyl, benzoimidazolyl, quinolinyl, isoquinolinyl, quinoxolinyl, quinoxolinyl, phenothiazinyl, phenothiazinyl, acridineyl, etc., but not limited to these.

[0031] The "linked ring formation" described in this invention refers to two groups being linked together by chemical bonds and optionally undergoing aromatization. Examples are shown below: .

[0032] In this specification, the rings formed by the linkage can be aromatic or non-aromatic rings, and can be three-membered, four-membered, five-membered, six-membered, seven-membered, eight-membered, fused rings, etc., such as cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, adamantane, norbornene, benzene, naphthalene, phenanthrene, triphenylene, pyridine, pyrimidine, quinoline, isoquinoline, quinazoline, quinoxaline, fluorene, dibenzofuran, dibenzothiophene, carbazole, etc., but not limited to these.

[0033] This invention provides an aromatic amine compound having the structure shown in Formula 1.

[0034] Wherein, Ar1 is selected from one or more R4-substituted groups of the following: aryl of C6 to C30, heteroaryl of C2 to C30, fused cycloalcoholic group of C3 to C30 aliphatic ring and C6 to C30 aromatic ring, fused cycloalcoholic group of C3 to C30 aliphatic ring and C2 to C30 heteroaromatic ring; At least one of the R4 groups is selected from an F-substituted alkyl group, and the remainder is selected from any one of hydrogen, deuterium, fluorine, cyano, substituted or unsubstituted silyl group, substituted or unsubstituted C1-C25 alkyl group, substituted or unsubstituted C3-C25 cycloalkyl group, substituted or unsubstituted C1-C25 heterocycloalkyl group, substituted or unsubstituted C6-C30 aryl group, and substituted or unsubstituted C2-C30 heteroaryl group. The Ar2 is selected from one or more R5-substituted groups of the following: aryl of C6 to C30, heteroaryl of C2 to C30, fused cycloalcoholic group of C3 to C30 aliphatic ring and C6 to C30 aromatic ring, and fused cycloalcoholic group of C3 to C30 aliphatic ring and C2 to C30 heteroaromatic ring. At least one of R5 is selected from F or an F-substituted alkyl group, and the remainder is selected from any one of hydrogen, fluorine, deuterium, silicon, cyano, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl. The Ar3, Ar4, Ar5, and Ar6 are independently selected from any one of the following: substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, fused cycloalcoholic groups of substituted or unsubstituted C3-C30 aliphatic rings and C6-C30 aromatic rings, and fused cycloalcoholic groups of substituted or unsubstituted C3-C30 aliphatic rings and C2-C30 heteroaromatic rings. R1, R2, and R3 are independently selected from any one of hydrogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 aliphatic ring, and fused cycloyl group of C6-C30 aromatic ring, and at least one of R1, R2, and R3 is not hydrogen; The L1, L2, L3, L4, L5, L6, L7, L8, and L9 are independently selected from any one of the following: single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted C3-C30 aliphatic ring and C6-C30 aromatic ring, substituted or unsubstituted C3-C30 aliphatic ring and C2-C30 heteroaromatic ring, and combinations thereof.

[0035] Preferably, the aromatic amine compound has the structure shown in any one of Formula 1-1, Formula 1-2, Formula 1-3, Formula 1-4, Formula 1-5, Formula 1-6, Formula 1-7, Formula 1-8, Formula 1-9, and Formula 1-10.

[0036] The limitations of Ar1, Ar2, Ar3, Ar4, Ar5, Ar6, R1, R2, R3, L1, L2, L3, L4, L5, L6, L7, L8, and L9 are the same as those described above.

[0037] Preferably, R1, R2, and R3 are independently selected from any one of hydrogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C18 aryl, and substituted or unsubstituted C6-C18 heteroaryl, and at least one of R1, R2, and R3 is not hydrogen; further, at most one of R1, R2, and R3 is a substituted or unsubstituted C3-C10 cycloalkyl, a substituted or unsubstituted C6-C18 aryl, or a substituted or unsubstituted C6-C18 heteroaryl.

[0038] Preferably, R1, R2, and R3 are independently selected from any one of hydrogen, cyano, nitro, trimethylsilyl, triethylsilyl, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C8 cycloalkyl, substituted or unsubstituted phenyl, and substituted or unsubstituted pyridine, and at least one of R1, R2, and R3 is not hydrogen; further, at most one of R1, R2, and R3 is a substituted or unsubstituted C3-C8 cycloalkyl, substituted or unsubstituted phenyl, or substituted or unsubstituted pyridine.

[0039] Preferably, the Ar1 is selected from any one of the following group A groups: Group A:

[0040] The v is independently selected from N or CH, and the v at the bonding site is selected from CH; The ring A is selected from substituted or unsubstituted C3~C30 aliphatic rings; X1, X2, X3, X4, and X5 are independently selected from any one of O, S, C (R1'R2'), and N (R3'); At least one of R4 is selected from F-substituted alkyl groups, and the remainder is selected from any one of hydrogen, deuterium, fluorine, cyano, substituted or unsubstituted silyl groups, substituted or unsubstituted C1-C6 alkyl groups, substituted or unsubstituted C3-C15 cycloalkyl groups, substituted or unsubstituted C1-C15 heterocycloalkyl groups, substituted or unsubstituted C6-C18 aryl groups, and substituted or unsubstituted C2-C18 heteroaryl groups. R1' and R2' are independently selected from any one of hydrogen, deuterium, fluorine, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 aliphatic ring and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C30 aliphatic ring and C2-C30 heteroaromatic ring; or R1' and R2' are connected to form a substituted or unsubstituted ring; or any one of R1' and R2' can be directly bonded to L1; R3' is selected from any one of hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl; or R3' can be directly bonded to L1; a1 is selected from 1, 2, 3, 4 or 5; a2 is selected from 1, 2, 3 or 4; a3 is selected from 1, 2, 3, 4, 5, 6 or 7; a4 is selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9; a5 is selected from 1 or 2; a6 is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; a7 is selected from 1, 2 or 3; when there are two or more R4s, the two or more R4s are the same or different from each other.

[0041] Preferably, the Ar1 is selected from any one of the following group A groups: Group A:

[0042] The limitations of X1, R4, R1', R2', R3', and R4' are the same as those described above.

[0043] The number e1 is selected from 0, 1, 2, 3, 4 or 5; the number e2 is selected from 0, 1, 2, 3 or 4; the number e3 is selected from 0, 1, 2 or 3; the number e4 is selected from 0, 1 or 2; the number e5 is selected from 0, 1, 2, 3, 4, 5 or 6; the number e6 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the number e7 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; when there are two or more R4s, the two or more R4s are the same or different from each other.

[0044] Preferably, at least one (1, 2, 3, 4, 5, 6 or more) of the R4 group is selected from any one of the following groups, and the remainder is selected from any one of hydrogen, deuterium, fluorine, cyano, substituted or unsubstituted silyl, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C1-C15 heterocycloalkyl, substituted or unsubstituted C6-C18 aryl, and substituted or unsubstituted C2-C18 heteroaryl.

[0045] Preferably, the Ar2 is selected from any one of the following group B groups: Group B:

[0046] The v' is independently selected from N or CH, and the v' at the bonding site is selected from CH; The ring B is selected from substituted or unsubstituted C3~C30 aliphatic rings; X'1, X'2, X'3, X'4, and X'5 are independently selected from any one of O, S, C (R4''R5''), and N (R6'); At least one of R5 is selected from F or an F-substituted alkyl group, and the remainder is selected from any one of hydrogen, fluorine, deuterium, silicon, cyano, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C1-C15 heterocycloalkyl, substituted or unsubstituted C6-C18 aryl, and substituted or unsubstituted C2-C18 heteroaryl. R4'' and R5'' are independently selected from any one of hydrogen, deuterium, fluorine, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 aliphatic ring and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C30 aliphatic ring and C2-C30 heteroaromatic ring; or R4'' and R5'' are connected to form a substituted or unsubstituted ring; or any one of R4'' and R5'' can be directly bonded to L2; The R6' is selected from any one of hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl; or the R6' can be directly bonded to L2; The b1 is selected from 1, 2, 3, 4, or 5; the b2 is selected from 1, 2, 3, or 4; the b3 is selected from 1, 2, 3, 4, 5, 6, or 7; the b4 is selected from 1, 2, 3, 4, 5, 6, 7, 8, or 9; the b5 is selected from 1 or 2; the b6 is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; the b7 is selected from 1, 2, or 3; when there are two or more R5s, the two or more R5s are the same as or different from each other.

[0047] Preferably, the Ar2 is selected from any one of the following group B groups: Group B:

[0048] The limitations of X'1, R5, R5', R4'', R5'', and R6' are the same as those described above.

[0049] The f1 is selected from 0, 1, 2, 3, 4 or 5; the f2 is selected from 0, 1, 2, 3 or 4; the f3 is selected from 0, 1, 2 or 3; the f4 is selected from 0, 1 or 2; the f5 is selected from 0, 1, 2, 3, 4, 5 or 6; the f6 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the f7 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; when there are two or more R5s, the two or more R5s are the same or different from each other.

[0050] Preferably, at least one (1, 2, 3, 4, 5, 6 or more) of the R5 is selected from F or any one of the following groups, and the remainder is selected from any one of hydrogen, deuterium, fluorine, cyano, substituted or unsubstituted silyl, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C1-C15 heterocycloalkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C2-C18 heteroaryl;

[0051] Preferably, five of the R5 groups are selected from F, or one, two, three, four or more are selected from any of the above groups, and the remainder are selected from hydrogen, deuterium, fluorine, cyano, substituted or unsubstituted silyl groups, or substituted or unsubstituted C1 to C6 alkyl groups.

[0052] Preferred, group B Optional , Optional , Optional , Optional ; R5 is selected from hydrogen, deuterium, fluorine, cyano, substituted or unsubstituted silyl group, substituted or unsubstituted C1-C6 alkyl group, and any one of the following groups; .

[0053] Preferably, Ar3, Ar4, Ar5, and Ar6 are independently selected from group A, group B, and any one of the following groups:

[0054] The t is independently selected from N or CH, and the t at the bonding site is selected from CH; The ring C is selected from substituted or unsubstituted aliphatic rings of C3 to C30; T1, T2, T3, T4, and T5 are independently selected from any one of O, S, C (R7R8), and N (R9); The R c R c R7 and R8 are independently selected from any one of hydrogen, deuterium, fluorine, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 aliphatic ring and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C30 aliphatic ring and C2-C30 heteroaromatic ring; or R7 and R8 are connected to form a substituted or unsubstituted ring; or any one of R7 and R8 can be directly bonded to any one of L3, L4, L5, and L6. R9 is selected from any one of hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl; or R9 can be directly bonded to any one of L3, L4, L5, and L6; c1 is selected from 0, 1, 2, 3, 4, or 5; c2 is selected from 0, 1, 2, 3, or 4; c3 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; c4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; c5 is selected from 0, 1, or 2; c6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; c7 is selected from 0, 1, 2, or 3; when there are two or more R... c At that time, two or more R c The same or different between each other, or two adjacent R c They connect with each other to form substituted or unsubstituted rings.

[0055] Preferably, Ar3, Ar4, Ar5, and Ar6 are independently selected from group A, group B, and any one of the following groups:

[0056] T1, T2, and T3 are independently selected from any one of O, S, C (R7R8), and N (R9); The s is independently selected from N or CH, and the s at the bonding site is selected from CH; The Rd It is independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloyl group of substituted or unsubstituted C3-C30 aliphatic ring and C6-C30 aromatic ring, and fused cycloyl group of substituted or unsubstituted C3-C30 aliphatic ring and C2-C30 heteroaromatic ring; The R7, R8, R c R c 'Independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, trifluoromethyl, substituted or unsubstituted silyl, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C1-C15 heterocycloalkyl, substituted or unsubstituted C6-C18 aryl, fused cycloalcoholic group of substituted or unsubstituted C3-C15 aliphatic ring and C6-C18 aromatic ring, substituted or unsubstituted C2-C18 heteroaryl; The R9 is selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C2-C18 heteroaryl, or fused cycloalgyl of substituted or unsubstituted C3-C15 aliphatic ring and C6-C18 aromatic ring; The d1 is selected from 0, 1, 2, 3, 4, or 5; the d2 is selected from 0, 1, 2, 3, or 4; the d3 is selected from 0, 1, 2, or 3; the d4 is selected from 0, 1, or 2; the d5 is selected from 0, 1, 2, 3, 4, 5, or 6; the d6 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; the d7 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the d8 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; the d9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12; the d 10 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14; the d 11 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; d 12 Selected from 0 or 1; when there are two or more R c At that time, two or more R c They are the same or different from each other.

[0057] Preferably, four (Ar3, Ar4, Ar5, and Ar6), three (Ar3, Ar4, and Ar5; or Ar3, Ar5, and Ar6), two (Ar3 and Ar4; or Ar3 and Ar5; or Ar5 and Ar6), one (Ar3, Ar4, Ar5, or Ar6), or zero are selected from Group A, Group B, or any of the following groups:

[0058] The R c R d The limitations are the same as those mentioned above; The d1 is selected from 0, 1, 2, 3, 4, or 5; the d2 is selected from 0, 1, 2, 3, or 4; the d3 is selected from 0, 1, 2, or 3; the d5 is selected from 0, 1, 2, 3, 4, 5, or 6; the d7 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; when there are two or more R... c At that time, two or more R c They are the same or different from each other.

[0059] Preferably, L1, L2, L3, L4, L5, L6, L7, L8, and L9 are independently selected from single bonds or any one of the following groups and combinations thereof:

[0060] The z is independently selected from C(R) 10 () or N, where z at the bonding site is selected from C atoms; p is selected from 1, 2 or 3; W1 and W2 are independently selected from O, S, and C(R). 11 R 12 ) or N(R 13 ); The ring D is selected from substituted or unsubstituted C3 to C30 aliphatic cyclic groups; The R 10 R 11 R 12 Independently selected from any one of hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 aliphatic ring and C6-C30 aromatic ring, substituted or unsubstituted silyl, or two adjacent R 10 They can connect to each other to form substituted or unsubstituted rings; or the R 11 R 12They can connect with each other to form substituted or unsubstituted rings; The R 13 It is selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and aromatic ring of C6-C30, and substituted or unsubstituted silyl.

[0061] Preferably, L1, L2, L3, L4, L5, L6, L7, L8, and L9 are independently selected from single bonds or any one of the following groups and combinations thereof:

[0062] The R 10 R 10 '、R 11 R 12 It is independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, trifluoromethyl, substituted or unsubstituted silyl, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C1-C15 heterocycloalkyl, substituted or unsubstituted germanyl, substituted or unsubstituted C6-C18 aryl, fused cycloalcoholic group of substituted or unsubstituted C3-C15 aliphatic ring and C6-C18 aromatic ring, and substituted or unsubstituted C2-C18 heteroaryl; The R 13 It is selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted germanyl, substituted or unsubstituted C2-C18 heteroaryl, fused cycloalcohols of substituted or unsubstituted C3-C15 aliphatic rings and C6-C18 aromatic rings, and combinations thereof; q1 is selected from 0, 1, 2, 3, or 4; q2 is selected from 0, 1, 2, 3, 4, 5, or 6; q3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; q4 is selected from 0, 1, 2, or 3; q5 is selected from 0, 1, or 2; q6 is selected from 0 or 1; q7 is selected from 0, 1, 2, 3, 4, or 5; when there are two or more R... 10 At that time, two or more R 10 They may be the same as or different from each other; or two adjacent R's10 They connect to each other to form substituted or unsubstituted rings.

[0063] Preferably, the aromatic amine compound is selected from at least one of the following structures: .

[0064] The above lists some specific structural forms of the aromatic amine compounds represented by Formula 1 of the present invention. However, the present invention is not limited to these listed chemical structures. Any structure based on the structure shown in Formula 1, with substituents as defined above, should be included.

[0065] The present invention also provides an organic electroluminescent device, comprising an anode, an organic layer, and a cathode, wherein the organic layer is located between the anode and the cathode or outside either the anode or the cathode, and the organic layer comprises at least one of the aromatic amine compounds.

[0066] Preferably, the organic functional layer is located between the anode and the cathode, and the organic functional layer includes at least one of a hole transport region, a light-emitting layer, and an electron transport region, wherein the hole transport region includes at least one of the aromatic amine compounds described in this invention.

[0067] Preferably, the hole transport region comprises at least one of a hole injection layer, a hole transport layer, and an electron blocking layer, wherein the hole transport layer material comprises at least one of the aromatic amine compounds described in this invention.

[0068] Preferably, the hole transport layer comprises a first hole transport layer and a second hole transport layer, and at least one of the first hole transport layer or the second hole transport layer comprises at least one of the aromatic amine compounds described in this invention.

[0069] Preferably, the light-emitting layer comprises a host material and a dopant material.

[0070] Preferably, the electron transport region comprises at least one of an electron injection layer, an electron transport layer, and a hole blocking layer.

[0071] Preferably, the organic layer is located on the side of the cathode opposite to the anode, and the organic layer includes a capping layer containing at least one of the aromatic amine compounds described in this invention.

[0072] This invention does not impose any particular limitation on the materials of the thin films in the organic electroluminescent device; substances known in the art can be used. The organic functional layers of the aforementioned organic electroluminescent device and the electrodes on both sides of the device are described below: The organic electroluminescent device of the present invention is typically formed on a substrate. The substrate can be any material that remains unchanged when forming electrodes or organic layers, such as glass, plastic, polymer films, silicon, etc.

[0073] In the organic electroluminescent device of the present invention, the anode material is preferably a high work function material that can promote hole injection into the organic layer. The anode material that can be used in the present invention can be selected from conductive polymers, metal oxides, metals, or alloys thereof. Specific examples include, but are not limited to, poly(3-methylthiophene), polypyrrole, polyaniline, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), vanadium, chromium, copper, zinc, and gold.

[0074] The hole injection layer material described in this invention is preferably a material with high hole injection capability, and may include metal oxides, phthalocyanine compounds, benzidine compounds, phenazine compounds, specifically such as silver oxide, vanadium oxide, tungsten oxide, copper oxide, N,N,N',N'-tetra(4-methoxyphenyl)benzidine (MeO-TPD), N,N'-diphenyl-N,N'-di-[4-(N,N-diphenylamine)phenyl]benzidine (NPNPB), etc., but is not limited thereto.

[0075] The hole transport layer material described in this invention is preferably a material with high hole mobility. It may include triarylamine derivatives, benzidine derivatives, fluorene derivatives, stilbene derivatives, and phthalocyanine compounds. Specific examples, in addition to the aromatic amine compounds provided in this invention, include N,N'-di(naphthyl-1-yl)-N,N'-di(phenyl)-2,2'-dimethylbenzidine (α-NPD), 4-[1-[4-[di(4-methylphenyl)amino]phenyl]cyclohexyl]-N-(3-methylphenyl)-N-(4-methylphenyl)aniline (TAPC), N,N,N',N'-tetra(3-methylphenyl)-3,3'-dimethylbenzidine (HMTPD), etc., but are not limited thereto. The aromatic amine compounds of this invention are preferred.

[0076] The electron blocking layer of this invention is preferably made of a material with good hole transport capability and electron blocking capability. This includes aromatic amine derivatives, Carbazole derivatives, etc. Specific examples of the electron blocking materials include, but are not limited to, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), etc.

[0077] The luminescent layer material of this invention includes a host luminescent layer material and a guest luminescent layer material. The luminescent layer can be a single luminescent layer or a composite luminescent layer. The guest material can be a fluorescent material or a phosphorescent material. Specific examples of the host material may include metal complexes such as aluminum complexes or zinc complexes, heterocyclic compounds such as oxadiazole derivatives or benzimidazole derivatives, fused aromatic compounds such as carbazole derivatives or anthracene derivatives, and aromatic amine compounds such as triarylamine derivatives or fused polycyclic aromatic amine derivatives, but are not limited to these. Specific examples of the guest material may include fluorescent compounds such as pyrene derivatives, fluoranthene derivatives, and aromatic amine derivatives, phosphorescent materials such as heavy metal complexes and phosphorescent rare earth metal complexes, but are not limited to these.

[0078] The hole-blocking layer described in this invention can typically be formed under the same conditions as the hole injection layer. Specifically, it may include triazine derivatives, quinoline derivatives, diazoxide-phenanthroline derivatives, azabenzene derivatives, anthrone derivatives, aluminum complexes, lithium complexes, beryllium complexes, oxazole derivatives, benzoxazole derivatives, thiazole derivatives, benzothiazole derivatives, imidazole derivatives, benzimidazole derivatives, phenanthroline derivatives, polymeric compounds, rare earth derivatives, etc., but is not limited to these.

[0079] The electron transport layer material described in this invention is preferably a material with strong electron-withdrawing ability. This includes imidazoles, triazoles, phenanthroline derivatives, quinolines, etc., specifically examples such as 4,4'-bis(4,6-diphenyl-1,3,5-triazinyl)biphenyl (BTB), 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene (TPBi), 4,7-diphenyl-1,10-phenanthroline (Bphen), 2-(4-biphenyl)-5-phenyloxadiazole (PBD), etc., but is not limited to these.

[0080] The electron injection layer material described in this invention is preferably a material with high electron injection properties. These include alkali metal salts, alkaline earth metal salts, metal oxides, etc., and the electron injection materials include, but are not limited to, lithium oxide, lithium fluoride, cesium carbonate, cesium fluoride, magnesium phosphide, etc.

[0081] The cathode material of this invention is preferably a material with a low work function. The cathode material of this invention includes, but is not limited to, metals, metal alloys, conductive compounds, and mixtures thereof. Specific examples of the cathode material include, but are not limited to, silver (Ag), magnesium (Mg), lithium (Li), aluminum (Al), gold (Au), and magnesium-silver (Mg-Ag).

[0082] The capping material described in this invention is preferably a material with photocoupling properties. Specific examples, in addition to the aromatic amine compounds described in this invention, may include aryl amine derivatives, biscarbazole derivatives, benzimidazole derivatives, benzoxazole derivatives, benzothiazole derivatives, etc. Specific examples include, but are not limited to, tris(8-hydroxyquinoline)aluminum(III) (Alq3), N,N'-di(naphthyl-1-yl)-N,N'-di(phenyl)-2,2'-dimethylbenzidine (NPD), 4,4'-di(9-carbazole)biphenyl (CBP), N4,N4,N4',N4'-tetra(4-methoxyphenyl)-[1,1'-biphenyl]-4,4'-diamine (MeO-TPD), lithium fluoride (LiF), magnesium fluoride (MgF2), etc. The aromatic amine compounds of this invention are preferred.

[0083] The present invention does not impose any special restrictions on the thickness of each organic layer of the organic electroluminescent device; thicknesses commonly used in the field can be adopted.

[0084] The organic electroluminescent device of the present invention can be made using any one of the following methods: vacuum evaporation, spin coating, vapor deposition, blade coating, laser thermal transfer, electrospray coating, slot coating, and dip coating. In the present invention, vacuum evaporation is preferred.

[0085] The organic electroluminescent device of the present invention can be a top-emitting type, a bottom-emitting type, or a bidirectional-emitting type.

[0086] The organic electroluminescent device described in this invention can be widely used in panel displays, lighting sources, flexible OLEDs, electronic paper, organic solar cells, organic photosensitive materials or organic thin-film transistors, signs, signal lights and other fields.

[0087] There are no particular limitations on the preparation method of the aromatic amine compound shown in Formula 1 of this invention, and conventional methods well known to those skilled in the art can be used. For example, carbon-nitrogen coupling reaction, carbon-carbon coupling reaction, etc. The aromatic amine compound shown in Formula 1 of this invention can be prepared using the synthetic route shown below.

[0088] Preparation of compound 1:

[0089] when , , At the same time, the compound of formula 1 is prepared via the following route:

[0090] when , Similarly, the compound of formula 1 is prepared via the following route:

[0091] when , , Similarly, the compound of formula 1 is prepared via the following route:

[0092] Xa is independently selected from any one of Cl, Br, and I; the limitations of Ar1, Ar2, Ar3, Ar4, Ar5, Ar6, L1, L2, L3, L4, L5, L6, L7, L8, L9, R1, R2, and R3 are the same as those described above.

[0093] The above-mentioned substituents can be bonded by methods known in the art, and the type and position or number of substituents can be changed according to techniques known in the art.

[0094] The invention is explained in more detail through the following examples, but is not intended to limit the invention. Based on this description, those skilled in the art will be able to practice the invention and prepare other compounds and devices according to the invention within the entire scope disclosed without inventive effort.

[0095] Preparation and characterization of compounds

[0096] Raw materials and reagents: This invention does not impose any particular limitations on the raw materials or reagents used in the following synthesis examples. They can be commercially available products or prepared using methods well-known to those skilled in the art. All raw materials and reagents used in this invention are of reagent purity.

[0097] Instruments: G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer (Waters Corporation, UK); Vario ELcube organic elemental analyzer (Elementar Corporation, Germany).

[0098] [Synthetic Example 1] Synthesis of Compound 22

[0099] Synthetic intermediate A-22

[0100] Under nitrogen protection, a-22 (22.39 g, 60.00 mmol), b-22 (17.58 g, 60.00 mmol), and sodium tert-butoxide (8.65 g, 90.00 mmol) dissolved in 300 mL toluene were added to a reaction flask. Pd(dppf)Cl2 (0.44 g, 0.60 mmol) was added with stirring, and the mixture was heated to reflux for 2.5 h. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallization from ethyl acetate yielded intermediate A-22 (30.20 g, 86% yield); HPLC analysis showed a solid purity ≥ 99.76%. Mass spectrometry m / z: 585.0562 (theoretical value: 585.0574).

[0101] Synthetic compound 22

[0102] Under nitrogen protection, m-22 (5.35 g, 15.00 mmol), A-22 (26.34 g, 45.00 mmol), and sodium tert-butoxide (2.16 g, 22.50 mmol) dissolved in 75 mL of toluene were added to a reaction flask. Pd₂(dba)₃ (0.18 g, 0.20 mmol) and X-Phos (0.093 g, 0.20 mmol) were added with stirring. The mixture of the above reactants was heated under reflux for 3.0 h. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallization from toluene gave compound 22 (19.64 g, 70% yield); HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 1869.21.80 (theoretical value: 1869.2191). Theoretical elemental content (%) C 78 H 36 F 45 N3: C, 50.10; H, 1.94; N, 2.25. Measured elemental content (%): C, 50.12; H, 1.91; N, 2.29.

[0103] [Synthetic Example 2] Synthesis of Compound 40

[0104] According to the preparation method in Example 1, a-22 was replaced with an equimolar amount of a-40, b-22 with an equimolar amount of b-40, and m-22 with an equimolar amount of m-40, yielding compound 40 (20.11 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 1637.2267 (theoretical value: 1637.2256). Theoretical elemental content (%) C 73 H 35 F 36 N3: C, 53.53; H, 2.15; N, 2.57. Measured elemental content (%): C, 53.49; H, 2.21; N, 2.54.

[0105] [Synthetic Example 3] Synthesis of Compound 95

[0106] According to the preparation method in Example 1, a-22 was replaced with an equimolar amount of a-95, and b-22 was replaced with an equimolar amount of b-95, yielding compound 95 (18.89 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 1527.1931 (theoretical value: 1527.1913). Theoretical elemental content (%) C 69 H 30 F 33N3: C, 54.24; H, 1.98; N, 2.75. Measured elemental content (%): C, 54.29; H, 1.95; N, 2.79.

[0107] [Synthetic Example 4] Synthesis of Compound 119

[0108] According to the preparation method in Synthesis Example 1, a-22 was replaced with an equimolar amount of a-119, b-22 was replaced with an equimolar amount of b-40, and m-22 was replaced with an equimolar amount of m-119, yielding compound 119 (21.07 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 1679.2714 (theoretical value: 1679.2726). Theoretical elemental content (%) C 76 H 41 F 36 N3: C, 54.33; H, 2.46; N, 2.50. Measured elemental content (%): C, 54.38; H, 2.44; N, 2.54.

[0109] [Synthetic Example 5] Synthesis of Compound 125

[0110] According to the preparation method in Synthesis Example 1, a-22 was replaced with an equimolar amount of a-125, and b-22 was replaced with an equimolar amount of b-40, yielding compound 125 (20.52 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 2097.3114 (theoretical value: 2097.3130). Theoretical elemental content (%) C 96 H 48 F 45 N3: C, 54.95; H, 2.31; N, 2.00. Measured elemental content (%): C, 54.90; H, 2.34; N, 2.01.

[0111] [Synthetic Example 6] Synthesis of Compound 152

[0112] According to the preparation method in Example 1, a-22 was replaced with an equimolar amount of a-152 to obtain compound 152 (20.03 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 1833.4437 (theoretical value: 1833.4447). Theoretical elemental content (%) C 87 H 63 F 36N3: C, 56.96; H, 3.46; N, 2.29. Measured elemental content (%): C, 56.90; H, 3.44; N, 2.34.

[0113] [Synthetic Example 7] Synthesis of Compound 155

[0114] According to the preparation method in Example 1, A-22 was replaced with an equimolar amount of A-155 to obtain compound 155 (18.65 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 1437.1619 (theoretical value 1437.1630). Theoretical elemental content (%) C 57 H 27 F 36 N3: C, 47.62; H, 1.89; N, 2.92. Measured elemental content (%): C, 47.66; H, 1.88; N, 2.89.

[0115] [Synthetic Example 8] Synthesis of Compound 166

[0116] According to the preparation method in Example 1, A-22 was replaced with an equimolar amount of A-166 to obtain compound 166 (20.64 g). HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 1299.0983 (theoretical value: 1299.0974). Theoretical elemental content (%) C 51 H 18 F 33 N3: C, 47.13; H, 1.40; N, 3.23. Measured elemental content (%): C, 47.15; H, 1.42; N, 3.17.

[0117] [Synthetic Example 9] Synthesis of Compound 167

[0118] According to the preparation method in Example 1, a-22 was replaced with an equimolar amount of a-167 to obtain compound 167 (20.46 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 1521.2580 (theoretical value: 1521.2569). Theoretical elemental content (%) C 63 H 39 F 36 N3: C, 49.72; H, 2.58; N, 2.76. Measured elemental content (%): C, 49.69; H, 2.57; N, 2.81.

[0119] [Synthetic Example 10] Synthesis of Compound 168

[0120] According to the preparation method in Synthesis Example 1, m-22 was replaced with an equimolar amount of m-168, and A-22 was replaced with an equimolar amount of A-166, yielding compound 168 (21.34 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 1299.0993 (theoretical value: 1299.0974). Theoretical elemental content (%) C 51 H 18 F 33 N3: C, 47.13; H, 1.40; N, 3.23. Measured elemental content (%): C, 47.10; H, 1.44; N, 3.25.

[0121] [Synthetic Example 11] Synthesis of Compound 200

[0122] Synthetic intermediate C-200

[0123] Under nitrogen protection, A-200 (21.11 g, 75.00 mmol), C-200 (14.36 g, 75.00 mmol), and sodium tert-butoxide (10.57 g, 110.0 mol) dissolved in 375 mL of toluene were added to a reaction flask. Pd(dppf)Cl2 (0.66 g, 0.9 mmol) was added with stirring, and the mixture was heated under reflux for 2.5 h. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallization from ethyl acetate yielded intermediate C-200 (28.48 g, 87% yield); HPLC analysis showed a solid purity ≥ 99.75%. Mass spectrometry m / z: 435.1576 (theoretical value: 435.1562).

[0124] Synthetic intermediate D-200

[0125] Under nitrogen protection, C-200 (23.01 g, 50 mmol), pinacol diborate (12.70 g, 50 mmol), and KOAc (9.81 g, 100 mmol) were dissolved in 450 mL of 1,4-dioxane. Pd(PPh3)4 (1.16 g, 1.00 mmol) was added with stirring, and the mixture was heated under reflux for 3.0 h. After the reaction was complete, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from the solid using toluene / ethanol in a 9:1 ratio to obtain intermediate D-200 (22.32 g, 88%). HPLC analysis showed a solid purity ≥ 99.88%. Mass spectrometry m / z: 483.3318 (theoretical value: 483.3309).

[0126] Synthetic intermediate E-200

[0127] Under nitrogen protection, B-200 (22.89 g, 75.00 mmol), c-200 (14.36 g, 75.00 mmol), and sodium tert-butoxide (10.57 g, 110.0 mol) dissolved in 375 mL of toluene were added to a reaction flask. Pd(dppf)Cl2 (0.66 g, 0.9 mmol) was added with stirring, and the mixture was heated to reflux for 2.5 h. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallization from ethyl acetate yielded intermediate E-200 (27.75 g, 89% yield); HPLC analysis showed a solid purity ≥ 99.79%. Mass spectrometry m / z: 415.0549 (theoretical value: 415.0562).

[0128] Synthetic intermediate F-200

[0129] Under nitrogen protection, E-200 (21.82 g, 50 mmol), pinacol diborate (12.70 g, 50 mmol), and KOAc (9.81 g, 100 mmol) were dissolved in 450 mL of 1,4-dioxane. Pd(PPh3)4 (1.16 g, 1.00 mmol) was added with stirring, and the mixture was heated under reflux for 3.0 h. After the reaction was complete, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from the solid using toluene / ethanol in a 9:1 ratio to obtain intermediate F-200 (22.07 g, 87%). HPLC analysis showed a solid purity ≥ 99.88%. Mass spectrometry m / z: 507.1823 (theoretical value: 507.1804).

[0130] Synthetic intermediate M-200

[0131] Under nitrogen protection, starting materials m-200 (8.04 g, 30.00 mmol), D-200 (14.51 g, 30.00 mmol), and Pd(OAc)2 (0.07 g, 0.30 mmol) were added to toluene / ethanol / water (2:1:1) (250 mL). The mixture was stirred, and then K2CO3 (8.29 g, 60 mmol) was added. The mixture was heated to reflux for 2 h. After the reaction was completed, the mixture was cooled to room temperature, and distilled water was added. The mixture was extracted with dichloromethane, allowed to stand, and the liquid was separated. The organic layer was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. The mixture was cooled to crystallize, filtered, and the resulting solid was recrystallized from ethyl acetate to obtain intermediate M-200 (12.91 g, yield 79%). HPLC analysis showed that the purity of the solid was ≥99.88%. Mass spectrometry m / z: 543.2448 (theoretical value: 543.2460).

[0132] Synthetic compound 200

[0133] Under nitrogen protection, raw materials M-200 (8.17 g, 15.00 mmol), F-200 (15.22 g, 30.00 mmol), and Pd(OAc)2 (0.07 g, 0.30 mmol) were added to toluene / ethanol / water (2:1:1) (300 mL), and the mixture was stirred. Then, K2CO3 (8.29 g, 60 mmol) was added, and the mixture was heated under reflux for 2.5 h. After the reaction was completed, the mixture was cooled to room temperature, and distilled water was added. The mixture was extracted with dichloromethane, allowed to stand, and separated. The organic layer was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. Crystallization was carried out at a lower temperature, filtered, and the resulting solid was recrystallized from ethyl acetate to give compound 200 (13.52 g, 73%). HPLC analysis showed that the solid purity was ≥99.98%. Mass spectrometry m / z: 1233.4848 (theoretical value: 1233.4830). Theoretical elemental content (%) C 75 H 63 F 12 N3: C, 72.98; H, 5.14; N, 3.40. Measured elemental content (%): C, 72.96; H, 5.19; N, 3.39.

[0134] [Synthetic Example 12] Synthesis of Compound 212

[0135] Synthetic intermediate M-212

[0136] Under nitrogen protection, m-200 (8.04 g, 30.00 mmol), A-212 (5.08 g, 30.00 mmol), and sodium tert-butoxide (4.32 g, 45.00 mmol) dissolved in 75 mL of toluene were added to a reaction flask. Pd₂(dba)₃ (0.03 g, 0.03 mmol) and X-Phos (0.01 g, 0.03 mmol) were added with stirring. The mixture of the above reactants was heated under reflux for 3.5 h. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallization from toluene yielded compound M-212 (8.44 g, 76% yield); HPLC analysis showed a solid purity ≥ 99.89%. Mass spectrometry m / z: 355.0881 (theoretical value: 355.0895).

[0137] Synthetic compound 212

[0138] Under nitrogen protection, M-212 (5.34 g, 15.00 mmol), B-212 (9.15 g, 30.00 mmol), and sodium tert-butoxide (2.16 g, 22.50 mmol) dissolved in 75 mL of toluene were added to a reaction flask. Pd₂(dba)₃ (0.41 g, 0.45 mmol) and X-Phos (0.21 g, 0.45 mmol) were added with stirring. The mixture of the above reactants was heated under reflux for 5.0 h. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallization from toluene yielded compound 212 (10.19 g, 76%); HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 893.2624 (theoretical value: 893.2639). Theoretical elemental content (%) C 49 H 35 F 12 N3: C 65.85; H 3.95; N 4.70. Measured element content (%): C 65.88; H 3.97; N 4.69.

[0139] [Synthetic Example 13] Synthesis of Compound 217

[0140] Synthetic intermediate B-217

[0141] According to the preparation method of Synthesis Example 1, a-22 was replaced with an equimolar amount of a-217, and b-22 was replaced with an equimolar amount of b-40, to obtain intermediate B-217 (23.22 g). The purity of the solid was ≥99.79% as determined by HPLC. Mass spectrometry m / z: 455.0532 (theoretical value: 455.0543).

[0142] Synthetic compound 217

[0143] According to the preparation method in Synthesis Example 12, A-212 was replaced with an equimolar amount of A-217, and B-212 was replaced with an equimolar amount of B-217 to obtain compound 217 (20.08 g). HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 1198.2754 (theoretical value: 1198.2762). Theoretical elemental content (%) C 55 H 30 D5F 24 N3: C, 55.10; H, 3.36; N, 3.50. Measured element content (%): C, 55.08; H, 3.41; N, 3.48.

[0144] [Synthetic Example 14] Synthesis of Compound 231

[0145] According to the preparation method in Synthesis Example 12, A-212 was replaced with an equimolar amount of A-231, and B-212 was replaced with an equimolar amount of B-200, yielding compound 231 (19.07 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 993.2941 (theoretical value: 993.2952). Theoretical elemental content (%) C 57 H 39 F 12 N3: C, 68.88; H, 3.96; N, 4.23. Measured elemental content (%): C, 68.87; H, 3.91; N, 4.25.

[0146] [Synthetic Example 15] Synthesis of Compound 232

[0147] Synthetic intermediate D-232

[0148] According to the preparation method of D-200 in Synthesis Example 11, A-200 was replaced with an equimolar amount of A-232, and c-200 was replaced with an equimolar amount of c-232 to obtain intermediate D-232 (17.87 g); HPLC purity ≥ 99.85%. Mass spectrometry m / z: 425.2455 (theoretical value: 425.2464).

[0149] Synthetic intermediate M-232

[0150] Under nitrogen protection, starting materials m-200 (8.04 g, 30.00 mmol), D-232 (12.76 g, 30.00 mmol), and Pd(OAc)2 (0.07 g, 0.30 mmol) were added to toluene / ethanol / water (2:1:1) (250 mL). The mixture was stirred, and then K2CO3 (8.29 g, 60 mmol) was added. The mixture was heated under reflux for 2 h. After the reaction was completed, the mixture was cooled to room temperature, and distilled water was added. The mixture was extracted with dichloromethane, allowed to stand, and separated. The organic layer was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. Crystallization was carried out at a lower temperature, filtered, and the resulting solid was recrystallized from ethyl acetate to give intermediate M-232 (11.68 g, 80% yield); HPLC purity ≥ 99.87%. Mass spectrometry m / z: 485.1631 (theoretical value: 485.1615).

[0151] Synthetic compound 232

[0152] According to the preparation method of compound 212 in Synthesis Example 12, M-212 was replaced with an equimolar amount of M-232, and B-212 was replaced with an equimolar amount of B-200, yielding compound 232 (18.29 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 1023.3379 (theoretical value: 1023.3360). Theoretical elemental content (%) C 59 H 37 D4F 12 N3: C, 69.20; H, 4.43; N, 4.10. Measured elemental content (%): C, 69.16; H, 4.46; N, 4.15.

[0153] [Synthetic Example 16] Synthesis of Compound 238

[0154] Following the preparation method of Synthesis Example 12, A-212 was replaced with an equimolar amount of A-238, and B-212 was replaced with an equimolar amount of A-155, yielding compound 238 (22.61 g). HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 1265.2435 (theoretical value: 1265.2448). Theoretical elemental content (%) C 61 H 35 F 24 N3: C, 57.88; H, 2.79; N, 3.32. Measured elemental content (%): C, 57.95; H, 2.78; N, 3.37.

[0155] [Synthetic Example 17] Synthesis of Compound 241

[0156] According to the preparation method in Synthesis Example 12, m-200 was replaced with an equimolar amount of m-241, A-212 was replaced with an equimolar amount of A-241, and B-212 was replaced with an equimolar amount of B-241, yielding compound 241 (19.10 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 1121.2246 (theoretical value: 1121.2262). Theoretical elemental content (%) C 62 H 31 F 16 N3: C, 66.38; H, 2.79; N, 3.75. Measured elemental content (%): C, 66.35; H, 2.83; N, 3.76.

[0157] [Synthetic Example 18] Synthesis of Compound 242

[0158] According to the preparation method in Synthesis Example 12, m-200 was replaced with an equimolar amount of m-242, A-212 was replaced with an equimolar amount of A-242, and B-212 was replaced with an equimolar amount of B-242, yielding compound 242 (20.91 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 1255.3186 (theoretical value: 1255.3170). Theoretical elemental content (%) C 69 H 43 F 18 N3: C, 65.98; H, 3.45; N, 3.35. Measured elemental content (%): C, 65.97; H, 3.49; N, 3.31.

[0159] [Synthetic Example 19] Synthesis of Compound 243

[0160] According to the preparation method in Synthesis Example 12, m-200 was replaced with an equimolar amount of m-243, A-212 was replaced with an equimolar amount of A-243, and B-212 was replaced with an equimolar amount of B-243, yielding compound 243 (22.08 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 1117.3247 (theoretical value: 1117.3265). Theoretical elemental content (%) C 67 H 43 F 12 N3: C, 71.97; H, 3.88; N, 3.76. Measured elemental content (%): C, 71.95; H, 3.84; N, 3.74.

[0161] [Synthetic Example 20] Synthesis of Compound 244

[0162] Following the preparation method of Synthesis Example 12, A-212 was replaced with an equimolar amount of A-244, and B-212 was replaced with an equimolar amount of B-231, yielding compound 244 (18.97 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 1147.3360 (theoretical value: 1147.3371). Theoretical elemental content (%) C 68 H 45 F 12 N3O: C, 71.14; H, 3.95; N, 3.66. Measured elemental content (%): C, 71.16; H, 3.92; N, 3.71.

[0163] [Synthetic Example 21] Synthesis of Compound 249

[0164] Following the preparation method of Synthesis Example 12, A-212 was replaced with an equimolar amount of A-249, and B-212 was replaced with an equimolar amount of B-243, yielding compound 249 (20.52 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 1027.3716 (theoretical value: 1027.3735). Theoretical elemental content (%) C 59 H 49 F 12 N3: C, 68.93; H, 4.80; N, 4.09. Measured elemental content (%): C, 68.98; H, 4.84; N, 4.06.

[0165] [Synthetic Example 22] Synthesis of Compound 336

[0166] According to the preparation method in Synthesis Example 12, A-212 was replaced with an equimolar amount of A-336, and B-212 was replaced with an equimolar amount of B-336, yielding compound 336 (22.87 g). HPLC analysis showed a solid purity ≥ 99.91%. Mass spectrometry m / z: 1031.2274 (theoretical value: 1031.2292). Theoretical elemental content (%) C 49 H 31 F 18 N5: C, 57.04; H, 3.03; N, 6.79. Measured elemental content (%): C, 57.05; H, 3.07; N, 6.76.

[0167] [Synthetic Example 23] Synthesis of Compound 340

[0168] Synthetic intermediate M-340

[0169] Under nitrogen protection, m-340 (10.78 g, 30.00 mmol), B-242 (11.20 g, 30.00 mmol), and sodium tert-butoxide (4.32 g, 45.00 mmol) dissolved in 75 mL of toluene were added to a reaction flask with stirring. Pd₂(dba)₃ (0.03 g, 0.03 mmol) and X-Phos (0.01 g, 0.03 mmol) were then added. The mixture of the above reactants was heated under reflux for 3.5 h. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallization from toluene yielded compound M-340 (15.42 g, 85%); HPLC purity ≥ 99.75%. Mass spectrometry m / z: 603.0030 (theoretical value: 603.0011).

[0170] Synthetic intermediate N-340

[0171] Under nitrogen protection, M-340 (15.11 g, 25.00 mmol), B-340 (6.133 g, 25.00 mmol), and sodium tert-butoxide (4.81 g, 50 mmol) dissolved in 450 mL of toluene were added to a reaction flask with stirring. Pd(OAc)₂ (0.06 g, 0.25 mmol) and P(t-Bu)₃ (1.00 mL, 0.50 mmol, 0.5 M toluene solution) were then added. The mixture of the above reactants was heated under reflux for 3.5 h. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. The mixture was purified by silica gel column chromatography with n-hexane / dichloromethane (8:1 v / v) to obtain intermediate N-340 (15.19 g, 79%); HPLC purity ≥ 99.86%. Mass spectrometry m / z: 768.1932 (theoretical value: 768.1954).

[0172] Synthetic compound 340

[0173] Under nitrogen protection, N-340 (11.54 g, 15.00 mmol), H-340 (4.82 g, 15.00 mmol), and sodium tert-butoxide (2.88 g, 30.00 mmol) dissolved in 60 mL of toluene were added to a reaction flask. Pd₂(dba)₃ (0.14 g, 0.15 mmol) and X-Phos (0.07 g, 0.15 mmol) were added with stirring. The mixture of the above reactants was heated under reflux for 3.0 h. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallization from toluene yielded compound 340 (11.70 g, 74%). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 1053.3721 (theoretical value: 1053.3705). Theoretical elemental content (%) C 66 H 48 F9N3: C, 75.20; H, 4.59; N, 3.99. Measured elemental content (%): C, 75.16; H, 4.61; N, 3.97.

[0174] [Synthetic Example 24] Synthesis of Compound 341

[0175] Synthetic intermediate A-341

[0176] According to the preparation method of Synthesis Example 1, a-22 was replaced with an equimolar amount of a-341 to obtain intermediate A-341 (23.14 g); HPLC analysis showed that the solid purity was ≥99.77%. Mass spectrometry m / z: 455.0279 (theoretical value: 459.0293).

[0177] Synthetic compound 341

[0178] According to the preparation method in Synthesis Example 12, A-212 was replaced with an equimolar amount of A-155, and B-212 was replaced with an equimolar amount of B-341 to obtain compound 341 (22.68 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 1143.3787 (theoretical value: 1143.3797). Theoretical elemental content (%) C 67 H 50 F 13 N3: C, 70.34; H, 4.41; N, 3.67. Measured elemental content (%): C, 70.32; H, 4.46; N, 3.63.

[0179] [Synthetic Example 25] Synthesis of Compound 348

[0180] According to the preparation method in Synthesis Example 12, A-212 was replaced with an equimolar amount of B-241, and B-212 was replaced with an equimolar amount of B-348 to obtain compound 348 (19.42 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 1027.3182 (theoretical value: 1027.3173). Theoretical elemental content (%) C 66 H 41 F8N3: C, 77.11; H, 4.02; N, 4.09. Measured elemental content (%): C, 77.14; H, 4.06; N, 4.04.

[0181] [Synthetic Example 26] Synthesis of Compound 371

[0182] Synthetic intermediate A-371

[0183] According to the preparation method of Synthesis Example 1, a-22 was replaced with an equimolar amount of a-371, and b-22 was replaced with an equimolar amount of b-95 ​​to obtain intermediate A-371 (16.29 g). The purity of the solid was ≥99.78% as determined by HPLC. Mass spectrometry m / z: 327.0282 (theoretical value: 327.0294).

[0184] Synthetic compound 371

[0185] According to the preparation method in Synthesis Example 12, A-212 was replaced with an equimolar amount of A-371, and B-212 was replaced with an equimolar amount of B-371 to obtain compound 371 (21.46 g). HPLC analysis showed a solid purity ≥ 99.91%. Mass spectrometry m / z: 1011.3788 (theoretical value: 1011.3799). Theoretical elemental content (%) C 64 H 49 F8N3: C, 75.95; H, 4.88; N, 4.15. Measured elemental content (%): C, 75.93; H, 4.84; N, 4.19.

[0186] [Synthetic Example 27] Synthesis of Compound 380

[0187] Following the preparation method of Synthesis Example 12, A-212 was replaced with an equimolar amount of A-380, and B-212 was replaced with an equimolar amount of B-380, yielding compound 380 (21.47 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 927.2998 (theoretical value: 927.2984). Theoretical elemental content (%) C 54 H 38F9N5: C, 69.90; H, 4.13; N, 7.55. Measured elemental content (%): C, 69.93; H, 4.17; N, 7.52.

[0188] [Synthetic Example 28] Synthesis of Compound 382

[0189] According to the preparation method in Synthesis Example 12, m-200 was replaced with an equimolar amount of m-382, A-212 was replaced with an equimolar amount of A-382, and B-212 was replaced with an equimolar amount of B-382, yielding compound 382 (23.06 g). HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 969.2433 (theoretical value: 969.2449). Theoretical elemental content (%) C 51 H 31 F 12 N7: C, 63.16; H, 3.22; N, 10.11. Measured element content (%): C, 63.14; H, 3.21; N, 10.17.

[0190] [Synthetic Example 29] Synthesis of Compound 383

[0191] According to the preparation method in Synthesis Example 12, A-212 was replaced with an equimolar amount of B-231, and B-212 was replaced with an equimolar amount of B-383, yielding compound 383 (23.06 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 991.3306 (theoretical value: 991.3321). Theoretical elemental content (%) C 61 H 43 F6N5O2: C, 73.86; H, 4.37; N, 7.06. Measured elemental content (%): C, 73.90; H, 4.42; N, 7.04.

[0192] [Synthetic Example 30] Synthesis of Compound 388

[0193] According to the preparation method in Synthesis Example 12, m-200 was replaced with an equimolar amount of m-388, A-212 was replaced with an equimolar amount of A-166, and B-212 was replaced with an equimolar amount of B-388, yielding compound 388 (23.98 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 999.2184 (theoretical value: 999.2175). Theoretical elemental content (%) C 54 H 36 F 11N3S2: C, 64.86; H, 3.63; N, 4.20. Measured elemental content (%): C, 64.81; H, 3.59; N, 4.23.

[0194] [Synthetic Example 31] Synthesis of Compound 404

[0195] According to the preparation method in Synthesis Example 12, m-200 was replaced with an equimolar amount of m-382, A-212 was replaced with an equimolar amount of A-382, and B-212 was replaced with an equimolar amount of B-404, yielding compound 404 (22.71 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 1045.2548 (theoretical value: 1045.2538). Theoretical elemental content (%) C 59 H 35 F 12 N3O2: C, 67.75; H, 3.37; N, 4.02. Measured elemental content (%): C, 67.77; H, 3.32; N, 4.06.

[0196] [Synthetic Example 32] Synthesis of Compound 407

[0197] Following the preparation method of Synthesis Example 12, A-212 was replaced with an equimolar amount of A-155, and B-212 was replaced with an equimolar amount of B-407, yielding compound 407 (21.92 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 1173.3146 (theoretical value: 1173.3164). Theoretical elemental content (%) C 69 H 43 F 12 N3O2: C, 70.59; H, 3.69; N, 3.58. Measured elemental content (%): C, 70.54; H, 3.65; N, 3.63.

[0198] [Synthetic Example 33] Synthesis of Compound 408

[0199] Synthetic intermediate D-408

[0200] According to the preparation method of D-200 in Synthesis Example 11, A-200 was replaced with an equimolar amount of A-212, and c-200 was replaced with an equimolar amount of c-408 to obtain compound D-408 (18.12 g). The purity of the solid was ≥99.78% as determined by HPLC. Mass spectrometry m / z: 421.2200 (theoretical value: 421.2213).

[0201] Synthetic intermediate M-408

[0202] According to the preparation method of M-212 in Synthesis Example 12, A-212 was replaced with an equimolar amount of B-242 to obtain compound M-408 (13.11 g). The purity of the solid was ≥99.86% as determined by HPLC. Mass spectrometry m / z: 559.0530 (theoretical value: 559.0516).

[0203] Synthetic compound 408

[0204] According to the preparation method in Synthesis Example 11, F-200 was replaced with an equimolar amount of D-408 to obtain compound 408 (11.48 g). HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 1077.3724 (theoretical value: 1077.3705). Theoretical elemental content (%) C 68 H 48 F9N3: C, 75.76; H, 4.49; N, 3.90. Measured elemental content (%): C, 75.74; H, 4.52; N, 3.95.

[0205] [Synthetic Example 34] Synthesis of Compound 432

[0206] According to the preparation method in Synthesis Example 12, m-212 was replaced with an equimolar amount of m-432, A-212 was replaced with an equimolar amount of A-155, and B-212 was replaced with an equimolar amount of B-432, yielding compound 432 (20.39 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 1327.7475 (theoretical value: 1327.7491). Theoretical elemental content (%) C 80 H 97 F 12 N3: C, 72.32; H, 7.36; N, 3.16. Measured elemental content (%): C, 72.30; H, 7.41; N, 3.11.

[0207] [Synthetic Example 35] Synthesis of Compound 481

[0208] Following the preparation method of Synthesis Example 12, A-212 was replaced with an equimolar amount of A-155, and B-212 was replaced with an equimolar amount of B-481, yielding compound 481 (20.14 g). HPLC analysis showed a solid purity ≥ 99.91%. Mass spectrometry m / z: 1037.3447 (theoretical value: 1037.3430). Theoretical elemental content (%) C 55 H 51 F 12 N3Si2: C, 63.63; H, 4.95; N, 4.05. Measured elemental content (%): C, 63.59; H, 4.98; N, 4.11.

[0209] [Synthetic Example 36] Synthesis of Compound 483

[0210] Synthetic intermediate A-483

[0211] According to the preparation method in Synthesis Example 1, a-22 was replaced with an equimolar amount of a-483 to obtain compound A-483 (23.45 g). The purity of the solid was ≥99.87% as determined by HPLC. Mass spectrometry m / z: 449.0839 (theoretical value: 449.0826).

[0212] Synthetic compound 483

[0213] According to the preparation method in Synthesis Example 23, B-242 was replaced with an equimolar amount of A-483, B-340 was replaced with an equimolar amount of B-242, and H-340 was replaced with an equimolar amount of B-241, yielding compound 483 (13.46 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 1263.2118 (theoretical value: 1263.2103). Theoretical elemental content (%) C 58 H 31 F 26 N3: C, 55.12; H, 2.47; N, 3.32. Measured elemental content (%): C, 55.16; H, 2.44; N, 3.33.

[0214] Device Examples

[0215] The organic materials used in the device fabrication examples were all purified by sublimation, with a purity of over 99.99%. The ITO glass substrates and ITO / Ag / ITO glass substrates used in the device fabrication examples were purchased commercially.

[0216] A combined IVL testing system was constructed, consisting of testing software, a computer, a Keithley K2400 digital source meter, and a Photo Research PR788 spectrophotometer. The device prepared according to this invention was tested at atmospheric pressure and room temperature at a current density of 10 mA / cm². 2 The luminous efficiency and driving voltage were measured. Using McScience's M6000 OLED lifetime testing system, the lifetime (T95: time (h) for brightness to decay to 95% of initial brightness) of the device prepared in this invention was tested at atmospheric pressure and room temperature. The current density during the test was 10 mA / cm². 2 .

[0217] [Device Example 1]

[0218] First, the ITO / Ag / ITO substrate was ultrasonically cleaned three times in distilled water for 10 minutes each time. After the distilled water cleaning was repeated twice, it was ultrasonically cleaned for 10 minutes each time. After the distilled water cleaning was completed, it was ultrasonically cleaned in sequence with isopropanol, acetone and methanol solvents, and then dried on a hot plate at 120°C.

[0219] An organic electroluminescent device was fabricated by vacuum evaporation on a pre-cleaned ITO / Ag / ITO substrate. The layers were: a hole injection layer HI-1:HT-1 = 3:97 (mass ratio, 15 nm); a hole transport layer HT-1 (100 nm); a second hole transport layer HT-2 (10 nm); a light-emitting layer BH-1:BD-1 = 99:1 (mass ratio, 30 nm); a hole blocking layer HB-1 (15 nm); an electron transport layer ET-1:Liq (mass ratio 1:1, 30 nm); an electron injection layer LiF (1.0 nm); and a cathode Mg:Ag = 1:9 (mass ratio, 15 nm). An inner capping layer CP-1 (70 nm) was then deposited on the cathode. Subsequently, an outer capping layer compound 22 (20 nm) was deposited on the inner capping layer. The structures of these compounds are shown in the following chemical formulas.

[0220]

[0221] [Device Examples 2-36]

[0222] Compounds 22, 40, 95, 119, 125, 152, 155, 166, 167, 168, 200, 212, 217, 231, 232, 238, 241, 242, 243, 244, 249, 336, 340, 341, 348, 371, 380, 382, ​​383, 388, 404, 407, 408, 432, 481, and 483 of this invention were used to replace compound 22 in device example 1 as the capping layer material. Otherwise, an organic electroluminescent device was prepared using the same preparation method as device example 1.

[0223] [Comparative Device Examples 1-2]

[0224] Comparative compounds R-1 and R-2 were used to replace compound 22 in device example 1 as the outer capping layer material. Otherwise, an organic electroluminescent device was prepared using the same preparation method as device example 1.

[0225] The luminescence characteristics test results of the organic electroluminescent devices obtained in Embodiments 1-36 of the present invention and Comparative Embodiments 1-2 are shown in Table 1 below.

[0226]

[0227] As can be seen from the data in Table 1, the application of the aromatic amine compounds described in this invention as capping materials in organic electroluminescent devices exhibits good light extraction efficiency and thermal stability, resulting in excellent luminous efficiency and lifespan for the devices.

[0228] [Device Example 37]

[0229] First, the ITO glass substrate was ultrasonically cleaned sequentially with pure water, isopropanol, acetone, and methanol, then exposed to ultraviolet light and ozone for 30 minutes before being placed in a vacuum evaporation apparatus for later use. The various organic layers were prepared using vacuum evaporation: First, a hole injection layer HI-2 (mass ratio, 30 nm); a first hole transport layer HT-3 (100 nm); a second hole transport layer compound 22 (40 nm); a light-emitting layer GH-1:GD-1 = 92:8 (mass ratio, 30 nm); an electron transport layer ET-2 : Liq = 1:1 (mass ratio, 30 nm); an electron injection layer LiF (1.0 nm); and a cathode Al (150 nm) were sequentially vacuum-deposited onto the ITO glass substrate (anode). This process fabricated an organic electroluminescent device. The structures of these compounds are shown in the following chemical formulas.

[0230]

[0231] [Device Examples 38-72]

[0232] Compounds 22, 40, 95, 119, 125, 152, 155, 166, 167, 168, 200, 212, 217, 231, 232, 238, 241, 242, 243, 244, 249, 336, 340, 341, 348, 371, 380, 382, ​​383, 388, 404, 407, 408, 432, 481, and 483 of this invention were used to replace compound 22 in device example 37 as the second hole transport layer material. Otherwise, an organic electroluminescent device was prepared using the same preparation method as device example 37.

[0233] [Comparative Device Examples 3-4]

[0234] Comparative compounds R-3 and R-4 were used to replace the compounds in device example 37 as the second hole transport layer materials. Otherwise, an organic electroluminescent device was prepared using the same preparation method as device example 37.

[0235] The luminescence characteristics test results of the organic electroluminescent devices obtained in Examples 37-72 and Comparative Examples 3-4 of the present invention are shown in Table 2 below.

[0236]

[0237] As can be seen from the data in Table 2, the aromatic amine compound shown in Formula 1 of this invention, when used as a second hole transport layer material, effectively reduces the device operating voltage, improves carrier recombination efficiency, and can effectively improve the luminous efficiency and lifespan of the device.

[0238] It should be noted that the present invention has been specifically described with reference to individual embodiments, but without departing from the principle of the invention, those skilled in the art will understand the general concept.

[0239] Various modifications or improvements in detail may be made to this invention by the art, and these modifications also fall within the protection scope of this invention.

Claims

1. An aromatic amine compound, characterized in that, The aromatic amine compound has the structure shown in Formula 1. Wherein, Ar1 is selected from one or more R4-substituted groups of the following: aryl of C6 to C30, heteroaryl of C2 to C30, fused cycloalcoholic group of C3 to C30 aliphatic ring and C6 to C30 aromatic ring, fused cycloalcoholic group of C3 to C30 aliphatic ring and C2 to C30 heteroaromatic ring; At least one of the R4 groups is selected from an F-substituted alkyl group, and the remainder is selected from any one of hydrogen, deuterium, fluorine, cyano, substituted or unsubstituted silyl group, substituted or unsubstituted C1-C25 alkyl group, substituted or unsubstituted C3-C25 cycloalkyl group, substituted or unsubstituted C1-C25 heterocycloalkyl group, substituted or unsubstituted C6-C30 aryl group, and substituted or unsubstituted C2-C30 heteroaryl group. The Ar2 is selected from one or more R5-substituted groups of the following: aryl of C6 to C30, heteroaryl of C2 to C30, fused cycloalcoholic group of C3 to C30 aliphatic ring and C6 to C30 aromatic ring, and fused cycloalcoholic group of C3 to C30 aliphatic ring and C2 to C30 heteroaromatic ring. At least one of R5 is selected from F or an F-substituted alkyl group, and the remainder is selected from any one of hydrogen, fluorine, deuterium, silicon, cyano, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl. The Ar3, Ar4, Ar5, and Ar6 are independently selected from any one of the following: substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, fused cycloalcoholic groups of substituted or unsubstituted C3-C30 aliphatic rings and C6-C30 aromatic rings, and fused cycloalcoholic groups of substituted or unsubstituted C3-C30 aliphatic rings and C2-C30 heteroaromatic rings. R1, R2, and R3 are independently selected from any one of hydrogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 aliphatic ring, and fused cycloyl group of C6-C30 aromatic ring, and at least one of R1, R2, and R3 is not hydrogen; The L1, L2, L3, L4, L5, L6, L7, L8, and L9 are independently selected from any one of the following: single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted C3-C30 aliphatic ring and C6-C30 aromatic ring, substituted or unsubstituted C3-C30 aliphatic ring and C2-C30 heteroaromatic ring, and combinations thereof.

2. The aromatic amine compound according to claim 1, characterized in that, The Ar1 is selected from any one of the following group A groups: Group A: The v is independently selected from N or CH, and the v at the bonding site is selected from CH; The ring A is selected from substituted or unsubstituted C3~C30 aliphatic rings; X1, X2, X3, X4, and X5 are independently selected from any one of O, S, C (R1'R2'), and N (R3'); At least one of R4 is selected from F-substituted alkyl groups, and the remainder is selected from any one of hydrogen, deuterium, fluorine, cyano, substituted or unsubstituted silyl groups, substituted or unsubstituted C1-C6 alkyl groups, substituted or unsubstituted C3-C15 cycloalkyl groups, substituted or unsubstituted C1-C15 heterocycloalkyl groups, substituted or unsubstituted C6-C18 aryl groups, and substituted or unsubstituted C2-C18 heteroaryl groups. R1' and R2' are independently selected from any one of hydrogen, deuterium, fluorine, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 aliphatic ring and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C30 aliphatic ring and C2-C30 heteroaromatic ring; or R1' and R2' are connected to form a substituted or unsubstituted ring; or any one of R1' and R2' can be directly bonded to L1; R3' is selected from any one of hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl; or R3' can be directly bonded to L1; a1 is selected from 1, 2, 3, 4 or 5; a2 is selected from 1, 2, 3 or 4; a3 is selected from 1, 2, 3, 4, 5, 6 or 7; a4 is selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9; a5 is selected from 1 or 2; a6 is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; a7 is selected from 1, 2 or 3; when there are two or more R4s, the two or more R4s are the same or different from each other.

3. The aromatic amine compound according to claim 1, characterized in that, The Ar2 is selected from any one of the following group B groups: Group B: The v' is independently selected from N or CH, and the v' at the bonding site is selected from CH; The ring B is selected from substituted or unsubstituted C3~C30 aliphatic rings; X'1, X'2, X'3, X'4, and X'5 are independently selected from any one of O, S, C (R4''R5''), and N (R6'); At least one of the R5 groups is selected from F or an F-substituted alkyl group, and the remainder is selected from any one of hydrogen, fluorine, deuterium, silicon, cyano, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C1-C15 heterocycloalkyl, substituted or unsubstituted C6-C18 aryl, and substituted or unsubstituted C2-C18 heteroaryl. R4'' and R5'' are independently selected from any one of hydrogen, deuterium, fluorine, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 aliphatic ring and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C30 aliphatic ring and C2-C30 heteroaromatic ring; or R4'' and R5'' are connected to form a substituted or unsubstituted ring; or any one of R4'' and R5'' can be directly bonded to L2; The R6' is selected from any one of hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl; or the R6' can be directly bonded to L2; The b1 is selected from 1, 2, 3, 4, or 5; the b2 is selected from 1, 2, 3, or 4; the b3 is selected from 1, 2, 3, 4, 5, 6, or 7; the b4 is selected from 1, 2, 3, 4, 5, 6, 7, 8, or 9; the b5 is selected from 1 or 2; the b6 is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; the b7 is selected from 1, 2, or 3; when there are two or more R5s, the two or more R5s are the same as or different from each other.

4. An aromatic amine compound according to claim 1, characterized in that, The Ar3, Ar4, Ar5, and Ar6 are independently selected from Group A, Group B, and any one of the following groups: The t is independently selected from N or CH, and the t at the bonding site is selected from CH; The ring C is selected from substituted or unsubstituted aliphatic rings of C3 to C30; T1, T2, T3, T4, and T5 are independently selected from any one of O, S, C (R7R8), and N (R9); The R c R c R7 and R8 are independently selected from any one of hydrogen, deuterium, fluorine, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 aliphatic ring and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C30 aliphatic ring and C2-C30 heteroaromatic ring; or R7 and R8 are connected to form a substituted or unsubstituted ring; or any one of R7 and R8 can be directly bonded to any one of L3, L4, L5, and L6. R9 is selected from any one of hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl; or R9 can be directly bonded to any one of L3, L4, L5, and L6; c1 is selected from 0, 1, 2, 3, 4, or 5; c2 is selected from 0, 1, 2, 3, or 4; c3 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; c4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; c5 is selected from 0, 1, or 2; c6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; c7 is selected from 0, 1, 2, or 3; when there are two or more R... c At that time, two or more R c The same or different between each other, or two adjacent R c They connect with each other to form substituted or unsubstituted rings.

5. An aromatic amine compound according to claim 1, characterized in that, The Ar3, Ar4, Ar5, and Ar6 are independently selected from Group A, Group B, and any one of the following groups: T1, T2, and T3 are independently selected from any one of O, S, C (R7R8), and N (R9); The s is independently selected from N or CH, and the s at the bonding site is selected from CH; The R d It is independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloyl group of substituted or unsubstituted C3-C30 aliphatic ring and C6-C30 aromatic ring, and fused cycloyl group of substituted or unsubstituted C3-C30 aliphatic ring and C2-C30 heteroaromatic ring; The R7, R8, R c R c 'Independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, trifluoromethyl, substituted or unsubstituted silyl, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C1-C15 heterocycloalkyl, substituted or unsubstituted C6-C18 aryl, fused cycloalcoholic group of substituted or unsubstituted C3-C15 aliphatic ring and C6-C18 aromatic ring, substituted or unsubstituted C2-C18 heteroaryl; The R9 is selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C2-C18 heteroaryl, or fused cycloalgyl of substituted or unsubstituted C3-C15 aliphatic ring and C6-C18 aromatic ring; The d1 is selected from 0, 1, 2, 3, 4, or 5; the d2 is selected from 0, 1, 2, 3, or 4; the d3 is selected from 0, 1, 2, or 3; the d4 is selected from 0, 1, or 2; the d5 is selected from 0, 1, 2, 3, 4, 5, or 6; the d6 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; the d7 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the d8 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; the d9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12; the d 10 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14; the d 11 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; d 12 Selected from 0 or 1; when there are two or more R c At that time, two or more R c They are the same or different from each other.

6. An aromatic amine compound according to claim 1, characterized in that, The L1, L2, L3, L4, L5, L6, L7, L8, and L9 are independently selected from single bonds or any one of the following groups and combinations thereof: The z is independently selected from C(R) 10 () or N, where z at the bonding site is selected from C atoms; p is selected from 1, 2 or 3; W1 and W2 are independently selected from O, S, and C(R). 11 R 12 ) or N(R 13 ); The ring D is selected from substituted or unsubstituted C3 to C30 aliphatic cyclic groups; The R 10 R 11 R 12 Independently selected from any one of hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 aliphatic ring and C6-C30 aromatic ring, substituted or unsubstituted silyl group, or two adjacent R groups. 10 They can connect to each other to form substituted or unsubstituted rings; or the R 11 R 12 They can connect with each other to form substituted or unsubstituted rings; The R 13 It is selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and aromatic ring of C6-C30, and substituted or unsubstituted silyl.

7. An aromatic amine compound according to claim 1, characterized in that, The aromatic amine compound is selected from at least one of the following structures: 。 8. An organic electroluminescent device, comprising an anode, an organic layer, and a cathode, wherein the organic layer is located between the anode and the cathode or outside either the anode or the cathode, characterized in that, The organic layer comprises at least one of the aromatic amine compounds according to any one of claims 1 to 7.

9. The organic electroluminescent device according to claim 8, wherein the organic layer is located between the anode and the cathode, and the organic layer comprises a hole transport region, a light-emitting layer, and an electron transport region, characterized in that, The hole transport region comprises at least one of the aromatic amine compounds according to any one of claims 1 to 7.

10. The organic electroluminescent device according to claim 8, wherein the organic layer is located outside either the anode or the cathode electrode, and the organic layer includes a capping layer, characterized in that, The coating layer comprises at least one of the aromatic amine compounds according to any one of claims 1 to 7.

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