Arylamine compound and organic electroluminescent device thereof

Abstract

The invention provides an arylamine compound and an organic electroluminescent device thereof, and particularly relates to the technical field of organic photoelectric materials. The compound disclosed by the invention has proper refractive index, film-forming property and thermal stability, and can reduce the loss of light reflected by a nearby electrode during luminescence and improve the light extraction rate when being used as a covering layer material, so that the luminous efficiency of a device is improved, the service life of the device is prolonged, and the performance of the device is improved; the compound has good hole mobility when being used as a hole transport material, and can balance the transport of electrons and holes, so that excitons are efficiently compounded in a luminous layer, the luminous efficiency of a device is further improved, and the service life of the device is prolonged. The preparation method of the compound is simple, raw materials are easy to obtain, and the compound can be widely applied to the fields of organic thin film transistors, panel display and the like and has good application effects and industrialization prospects.

Description

Technical Field

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

[0002] Organic light-emitting diodes (OLEDs) are a type of self-emissive display technology. Compared with traditional display devices such as liquid crystal displays (LCDs), they have significant advantages in terms of self-emissiveness, wide viewing angle without distortion, extremely fast response speed, flexibility and bendability, and have unique advantages in terms of structure, performance and application scenarios.

[0003] The core of an OLED device is a multilayer thin-film stacked structure, which includes a substrate, anode, hole injection layer, hole transport layer, light-emitting layer, electron transport layer, electron injection layer, cathode, and capping layer. Its light-emitting mechanism is that, under the action of voltage, holes from the anode and electrons from the cathode are transported to the light-emitting layer and combine to form excitons. During the process of the excitons transitioning from the ground state to the excited state and then back from the excited state to the ground state, energy is converted from electrical energy into light energy.

[0004] Organic light-emitting materials play a decisive role in the lifespan and performance of devices. For example, a good capping layer material possesses high light transmittance and high barrier properties; a good hole transport layer material possesses high hole mobility and high thermal stability to ensure high luminous efficiency and extended device lifespan. However, in existing technologies, capping layers suffer from refractive index mismatch and poor stability, which reduces the luminous efficiency and shortens the device's lifespan. Furthermore, the low carrier mobility of hole transport layer materials leads to an imbalance in electron and hole transport, making it difficult for excitons to recombine efficiently in the light-emitting layer, thus affecting the device's luminous efficiency and lifespan.

[0005] Therefore, to solve the above problems, OLED materials need further improvement and development. It is crucial to develop new and efficient capping layer materials and hole transport layer materials so that the devices can have higher luminous efficiency and longer lifespan. Summary of the Invention

[0006] To address the aforementioned problems, the present invention aims to provide an aromatic amine compound and its organic electroluminescent device, which can improve the luminous efficiency of the organic electroluminescent device and extend its service life.

[0007] This invention provides an aromatic amine compound having a structure represented by Formula I:

[0008] Wherein, Ar1, Ar2, 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, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl groups, substituted or unsubstituted C1-C25 heterocyclic alkanes and C6-C30 aromatic ring fused cycloyl groups, and substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl groups; R1, R2, and R3 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, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cycloyl groups; and at least one of R1, R2, and R3 is not selected from hydrogen; When at least one of R1, R2, and R3 is selected from deuterium, at least one of Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 is replaced by F or CF3; When R1, R2, and R3 are not selected from deuterium, at least one of Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 is substituted by F or CF3, and at least one of the remaining ones is substituted by any one of deuterium, C1-C25 alkyl groups, and C3-C25 cycloalkyl groups. The L1, L2, L3, L4, L5, and L6 are independently selected from any one of the following: single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C6-C30 heteroarylene, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, and substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic rings.

[0009] The present invention also provides an organic electroluminescent device, comprising an anode, a cathode, and an organic layer, wherein the organic layer is located between the anode and the cathode or on the side of the cathode away from the anode, and the organic layer comprises at least one of the aromatic amine compounds described in the present invention.

[0010] Beneficial effects

[0011] This invention provides an aromatic amine compound with suitable refractive index, film-forming properties, and thermal stability. When used as a capping layer material, it can reduce light loss due to reflection from nearby electrodes during emission, improve light extraction efficiency, and thus enhance the luminous efficiency and lifespan of the device, thereby improving device performance. When used as a hole transport material, this compound exhibits good hole mobility, balancing electron and hole transport, enabling efficient exciton recombination in the luminescent layer, further improving the luminous efficiency and extending the device's lifespan. The compound provided by this invention has a simple preparation method, readily available raw materials, and can meet industrialization needs, demonstrating good industrialization prospects. Detailed Implementation

[0012] The technical solutions of the present invention will be clearly and completely described below with reference to the embodiments of the present invention. Obviously, the described embodiments are only some embodiments of the present invention, and not all embodiments. After reading the present invention, any modifications of the present invention in various equivalent forms by those skilled in the art fall within the scope defined by the present invention.

[0013] The alkyl group described in this invention refers to a monovalent group formed by removing one hydrogen atom from an alkane molecule. It can include straight-chain alkyl groups or branched alkyl groups, preferably having 1 to 25 carbon atoms, more preferably having 1 to 12 carbon atoms, more preferably 1 to 8 carbon atoms, and particularly preferably 1 to 6 carbon atoms. The straight-chain alkyl group includes, but is not limited to, methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, and dodecyl groups; the branched alkyl group includes, but is not limited to, isomers of isopropyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, and n-decyl groups.

[0014] The cycloalkyl group described in this invention refers to a monovalent group formed by removing one hydrogen atom from a cyclic alkane molecule, preferably having 3 to 25 carbon atoms, more preferably 3 to 12 carbon atoms, particularly preferably 5 to 10 carbon atoms, and most preferably 5 to 7 carbon atoms. Examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, camphenyl, etc., but are not limited thereto.

[0015] The heterocyclic alkyl group described in this invention refers to a group formed by removing one hydrogen atom from a heterocyclic molecule in which the atoms constituting the ring contain at least one heteroatom in addition to carbon atoms. The heteroatom includes, but is not limited to, oxygen, sulfur, nitrogen, or phosphorus, and preferably has 1 to 25 carbon atoms, more preferably 1 to 15 carbon atoms, more preferably 2 to 12 carbon atoms, and particularly preferably 2 to 6 carbon atoms. Examples include piperidinyl, piperazine, tetrahydropyrrolyl, morpholinyl, thiomorpholinyl, ethylene oxide, cyclothioethanediyl, etc., but are not limited thereto.

[0016] The aryl group described in this invention refers to a group formed by removing a hydrogen atom from one of the aromatic carbon atoms of an aromatic hydrocarbon molecule. It can be a monocyclic aryl, polycyclic aryl, or fused-ring aryl, preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 15 carbon atoms, and most preferably 6 to 12 carbon atoms. The monocyclic aryl refers to an aryl group with only one aromatic ring in the molecule, such as phenyl, but not limited thereto; the polycyclic aryl refers to an aryl group containing two or more independent aromatic rings in the molecule, such as biphenyl, terphenyl, etc., but not limited thereto; the fused-ring aryl refers to an aryl group containing two or more aromatic rings fused together by sharing two adjacent carbon atoms, such as naphthyl, anthracene, phenanthryl, pyrene, perylene, fluorene, benzo[a]fluorene, triphenylene, fluoranyl, spirodifluorene, etc., but not limited thereto.

[0017] The heteroaryl group described in this invention refers to a group formed by replacing one or more aromatic carbon atoms in an aryl group with heteroatoms. The heteroatoms include, but are not limited to, oxygen, sulfur, nitrogen, or phosphorus. The heteroaryl group can be a monocyclic heteroaryl, a polycyclic heteroaryl, or a fused-ring heteroaryl, preferably having 2 to 30 carbon atoms, more preferably 2 to 18 carbon atoms, particularly preferably 2 to 15 carbon atoms, and most preferably 2 to 12 carbon atoms. The monocyclic heteroaryl groups include, but are not limited to, pyridinyl, pyrimidinyl, triazinyl, furanyl, thiopheneyl, pyrroleyl, imidazolyl, etc.; the polycyclic heteroaryl groups include, but are not limited to, bipyridinyl, bipyrimidinyl, phenylpyridinyl, etc.; the fused-ring heteroaryl groups include, but are not limited to, quinolinyl, isoquinolinyl, indolyl, benzothiopheneyl, benzofuranyl, benzoxazolyl, benzoimidazolyl, benzothiazolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothiopheneyl, benzodibenzothiapheneyl, carbazolyl, benzocarbazolyl, acridinel, 9,10-dihydroacridinyl, phenoxazinyl, phenthiazinyl, phenoxthiazyl, etc., but are not limited to.

[0018] The fused cyclic group of alicyclic and aromatic rings described in this invention refers to the general term for the monovalent group obtained after removing one hydrogen atom from the fused alicyclic and aromatic rings. Preferably, it has 7 to 30 carbon atoms, more preferably 7 to 18 carbon atoms, and most preferably 7 to 13 carbon atoms. The fused cyclic group of alicyclic and aromatic rings may include, but is not limited to, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, etc. The linking site of the fused cyclic group can be on the aromatic ring (e.g., benzene ring) or on the alicyclic ring, but is preferably on the aromatic ring (e.g., benzene ring).

[0019] The fused cyclic group of heterocyclic alkanes and aromatic rings described in this invention refers to the collective term for the monovalent group obtained after removing one hydrogen atom from the fused heterocyclic alkanes and aromatic rings. Preferably, it has 6 to 30 carbon atoms, more preferably 7 to 18 carbon atoms, and most preferably 7 to 13 carbon atoms. The fused cyclic group of heterocyclic alkanes and aromatic rings may include, but is not limited to, benzo[a]tetrahydropyrrole, naph[a]tetrahydropyrrole, phenanthrene[a]tetrahydropyrrole, benzo[a]hexacyclic butyl, benzo[a]hexacyclic heptyl, benzo[a]piperidinyl, naph[a]piperidinyl, phenanthrene[a]piperidinyl, etc.

[0020] The fused cyclic group of alicyclic and heteroaromatic rings described in this invention refers to the general term for the monovalent group obtained after removing one hydrogen atom from the fused alicyclic and heteroaromatic rings. Preferably, it has 5 to 30 carbon atoms, more preferably 5 to 18 carbon atoms, and most preferably 5 to 12 carbon atoms. The fused cyclic group of alicyclic and heteroaromatic rings may include dibenzofuranocyclopropyl, dibenzofuranocyclobutyl, dibenzofuranocyclopentyl, dibenzofuranocyclohexyl, dibenzofuranocycloheptyl, dibenzothiophenocyclopropyl, dibenzothiophenocyclobutyl, dibenzothiophenocyclopentyl, dibenzothiophenocyclohexyl, etc. Benzothiophene-cycloheptyl, carbazo-cyclopropyl, carbazo-cyclobutyl, carbazo-cyclopentyl, carbazo-cyclohexyl, carbazo-cycloheptyl, carbazo-cyclopentenyl, pyrido-cyclopropyl, pyrido-cyclobutyl, pyrido-cyclopentyl, pyrido-cyclohexyl, pyrido-cycloheptyl, pyrido-cyclopentenyl, pyrimidino-cyclopropyl, pyrimidino-cyclobutyl, pyrimidino-cyclopentyl, pyrimidino-cyclohexyl, pyrimidino-cycloheptyl, pyrimidino-cyclopentenyl, etc., but not limited to these.

[0021] The arylene group described in this invention refers to a divalent group formed by removing one hydrogen atom from each of the two aromatic carbon atoms of an aromatic hydrocarbon molecule. It can be a divalent monocyclic aryl group or a divalent fused-ring aryl group, preferably having 6 to 30 carbon atoms, more preferably 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 18 carbon atoms, and most preferably 6 to 12 carbon atoms. Examples of arylene groups include phenylene, biphenylene, terphenylene, naphthylene, anthracene, phenanthrene, trimethyleneene, fluorene, pyrene, perylene, etc., but are not limited thereto.

[0022] The heteroaryl group described in this invention refers to a group formed by replacing one or more aromatic carbon atoms in an aryl group with heteroatoms. The heteroatoms include, but are not limited to, oxygen, sulfur, nitrogen, or phosphorus. The divalent heteroaryl group can be a divalent monocyclic heteroaryl or a divalent fused-ring heteroaryl, preferably having 2 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 15 carbon atoms. For example, it can be selected from pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, bipyridinyl, bipyrimidinyl, phenylpyridinyl, phenylpyrimidinyl, quinolineyl, isoquinolineyl, furanyl, thiopheneyl, carbazolyl, benzofuranyl, benzothiopheneyl, benzocarbazolyl, dibenzofuranyl, dibenzothiopheneyl, dibenzocarbazolyl, benzodibenzofuranyl, benzodibenzothiopheneyl, etc., but is not limited thereto.

[0023] The alicyclic and aromatic ring fused cyclic groups described in this invention refer to the divalent groups formed by removing two hydrogen atoms after the alicyclic and aromatic rings are fused together. Preferably, they have 7 to 30 carbon atoms, more preferably 7 to 18 carbon atoms, and most preferably 7 to 13 carbon atoms. Examples include, but are not limited to, benzo[a]cyclopropyl, benzo[a]cyclobutyl, benzo[a]cyclopentyl, benzo[a]cyclohexyl, benzo[a]cycloheptyl, naphtho[a]cyclopropyl, naphtho[a]cyclobutyl, naphtho[a]cyclopentyl, and naphtho[a]cyclohexyl.

[0024] The fused alicyclic and heteroaromatic ring cyclic groups described in this invention refer to the divalent groups formed by removing two hydrogen atoms after the alicyclic and heteroaromatic rings are fused together. Preferably, they have 5 to 30 carbon atoms, more preferably 5 to 18 carbon atoms, and most preferably 5 to 12 carbon atoms. Examples include dibenzofuranocyclopropyl, dibenzofuranocyclobutyl, dibenzofuranocyclopentyl, dibenzofuranocyclohexyl, dibenzofuranocycloheptyl, dibenzothiophenocyclopropyl, dibenzothiophenocyclobutyl, dibenzothiophenocyclopentyl, and dibenzothiophenocyclohexyl. Dibenzothiophene-cycloheptyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, pyridinyl-cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, benzophenyl-cycloheptyl, pyrimidinyl-cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, benzophenyl-cycloheptyl, pyrimidinyl-cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, benzophenyl-cycloheptyl, etc., but not limited to these.

[0025] Examples of halogen atoms described in this invention may include fluorine, chlorine, bromine, and iodine.

[0026] The "substituted or unsubstituted silyl group" mentioned in this invention refers to -Si(R n )3 groups, wherein each R nThe same or different from any one selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl.

[0027] The substituents described in the "substituted or unsubstituted" of this invention may be independently selected from deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcohols of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C1-C6 alkylthio, substituted or unsubstituted C1-C12 alkylamine, substituted or unsubstituted C6-C30 aryloxy, etc., but are not limited thereto, or adjacent substituents may be linked to form a ring. Preferred compounds include deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl groups, C1-C25 alkyl groups, C3-C25 cycloalkyl groups, C6-C30 aryl groups, C2-C30 heteroaryl groups, C3-C30 alicyclic and C6-C30 fused cycloyl groups, and C1-C12 alkoxy groups. Specific examples may include deuterium, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, propyl, butyl, cyclopropyl, cyclohexyl, adamantyl, norbornel, phenyl, tolyl, mesitylene, pentadeuterated phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, perylene, pyrene, fluoranyl, indene, dihydroindene, dihydronaphthyl, tetrahydronaphthyl, and 9,9 -Dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, spirodifluorenyl, carbazolyl, 9-phenylcarbazolyl, carbazo-indoleyl, pyrrololyl, furanyl, thiophene, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, pyridyl, pyrimidinyl, pyrazinyl, pyrazinyl, triazinyl, oxazolyl, thiazolyl, imidazolyl, benzooxazolyl, benzothiazolyl, benzotriazolyl, benzoimidazolyl, quinolinyl, isoquinolinyl, quinoxolinyl, quinazolinyl, phenothiazinyl, phenothiazinyl, acridineyl, benzocyclobutyl, benzocyclobutenyl, benzocyclopentyl, benzocyclopentenyl, benzocyclohexyl, benzocyclohexenyl, etc., but not limited to these. Or, when there are multiple substituents, the multiple substituents may be the same or different from each other; or adjacent substituents may be connected to form a ring.

[0028] In this specification, " "This refers to the portion that is connected to another substituent." "It can be attached to any optional position of the attached group / fragment."

[0029] 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 ring. For example, Can represent or ; Can represent , , And so on.

[0030] In this specification, when the position of a substituent or linking site on the ring is not fixed, it means that it can be linked to any of the optional sites on the ring.

[0031] For example, Can represent , , ; Can represent , , ; Can represent , , , , , , , , , .

[0032] And so on.

[0033] 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:

[0034] In this invention, the ring formed by the connection can be an aromatic ring system, an aliphatic ring system, or a ring system formed by the fusion of the two. The ring formed by the connection can be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring, or a fused ring, such as benzene, naphthalene, indene, cyclopentene, cyclopentane, cyclopentanophenene, cyclohexene, cyclohexane, cyclohexanophenene, quinoline, isoquinoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, phenanthrene, or pyrene, but is not limited thereto.

[0035] In this invention, "at least one" includes one, two, three, or more. "Two or more" may include two, three, four, or more, where permissible.

[0036] This invention provides an aromatic amine compound having a structure represented by Formula I:

[0037] Wherein, Ar1, Ar2, 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, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl groups, substituted or unsubstituted C1-C25 heterocyclic alkanes and C6-C30 aromatic ring fused cycloyl groups, and substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl groups; R1, R2, and R3 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, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cycloyl groups; and at least one of R1, R2, and R3 is not selected from hydrogen; When at least one of R1, R2, and R3 is selected from deuterium, at least one of Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 is replaced by F or CF3; When R1, R2, and R3 are not selected from deuterium, at least one of Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 is substituted by F or CF3, and at least one of the remaining ones is substituted by any one of deuterium, C1-C25 alkyl groups, and C3-C25 cycloalkyl groups. The L1, L2, L3, L4, L5, and L6 are independently selected from any one of the following: single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C6-C30 heteroarylene, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, and substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic rings.

[0038] Preferably, formula I is selected from any of the following structures:

[0039] The definitions of Ar1, Ar2, Ar3, Ar4, Ar5, Ar6, L1, L2, L3, L4, L5, L6, R1, R2, and R3 are the same as those in Equation I.

[0040] Preferably, R1, R2, and R3 are independently selected from hydrogen, deuterium, fluorine, cyano, nitro, and substituted or unsubstituted groups of the following: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, Benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyrene, perylene, pyridyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thiophene, benzothiophene, dibenzothiophene, benzodibenzothiophene, pyrroleyl, indolyl, carbazoleyl, oxazolyl, The following is a list of R1, R2, and R3: benzoxazolyl, dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzimidazolyl, dibenzoimidazolyl, quinolinyl, benzoquinolinyl, isoquinolinyl, benzoisoquinolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenantholinyl, naphridinyl, acridineyl, phenoxazinyl, and phenothiazinyl; and at least one of R1, R2, and R3 is not selected from hydrogen.

[0041] Preferably, Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 are independently selected from any one of the following groups;

[0042] The v is independently selected from either CH or N; The ring A is selected from substituted or unsubstituted C3~C10 alicyclic rings; X1 and X2 are independently selected from O, S, and N(R). z Any one of the following; X3, X4, and X5 are independently selected from O, S, and C(R). x R y ), N(R z Any one of the following; The R a R a '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 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl; The R x R y 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, or R x R y The links between them form substituted or unsubstituted rings; The R z It is independently 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; a1 is selected from 0, 1, 2, 3, 4, or 5; a2 is selected from 0, 1, 2, 3, or 4; a3 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; a4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; a5 is selected from 0, 1, or 2; a6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; a7 is selected from 0, 1, 2, or 3; when there are two or more R... a At that time, two or more R a The same or different between each other, or two adjacent R a They connect with each other to form substituted or unsubstituted rings; The a'1 is selected from 0, 1, or 2; when there are two or more R a At that time, two or more R a 'They are the same as or different from each other.'

[0043] More preferably, Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 are independently selected from any one of the following groups;

[0044] The R a R a The group is independently selected from hydrogen, deuterium, fluorine, cyano, nitro, and the following groups, whether substituted or unsubstituted: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl. Benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyrene, perylene, pyridyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thiophene, benzothiophene, dibenzothiophene, benzodibenzothiophene, pyrroleyl, indoleyl, carbazole any one of the following: alkyl, oxazolyl, benzoxazolyl, dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzoimidazolyl, dibenzoimidazolyl, quinolinyl, benzoquinolinyl, isoquinolinyl, benzoisoquinolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenantholinyl, naphridyl, acridineyl, phenoxazinyl, phenothiazinyl; or two adjacent R groups. a They can be linked together to form substituted or unsubstituted rings: benzene ring, naphthalene ring, pyridine ring, pyrimidine ring; The R x R yThe group independently selected from hydrogen, deuterium, fluorine, cyano, nitro, or substituted or unsubstituted groups of the following: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl The following are all of the following: silyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyrene, perylene, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, and triazinyl; The R z The following groups, independently selected from hydrogen, deuterium, substituted or unsubstituted, are allowed: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl. The following are all of the following: vinyl dimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyrene, perylene, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, and triazinyl; a'1 is selected from 0, 1, or 2; a'2 is selected from 0, 1, 2, 3, or 4; a'3 is selected from 0, 1, 2, 3, 4, 5, or 6; a'4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; a'5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; when there are two or more R... a At that time, two or more R a 'They are the same as or different from each other.'

[0045] More preferably, Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 are independently selected from any one of the following groups; .

[0046] Preferably, at most three, two, or one of Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 are not [specific values]. And as described above The preferred method.

[0047] Preferably, when at least one of R1, R2, and R3 is selected from deuterium, at least one, at least two, or at least three of Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 are selected from: .

[0048] Preferably, when at least one of R1, R2, and R3 is selected from deuterium, the remainder is selected from hydrogen or deuterium. More preferably, one, two, or three of R1, R2, and R3 are selected from deuterium, and the remainder are selected from hydrogen.

[0049] When R1, R2, and R3 are not selected from deuterium, at least one, at least two, or at least three of Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 are selected from:

[0050] And the remaining at least one, or at least two, or at least three are selected from: .

[0051] Preferably, L1, L2, L3, L4, L5, and L6 are independently selected from single bonds or any one of the following groups:

[0052] The u is independently selected from either CH or N; Y1 and Y2 are independently selected from O, S, and N(R). s Any one of the following; Y3, Y4, and Y5 are independently selected from O, S, and C(R).p R q ), N(R s Any one of the following; The ring B is selected from substituted or unsubstituted C3~C10 alicyclic rings; The R b R b '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 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl; The R p R q 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, or R p R q The links between them form substituted or unsubstituted rings; The R z It is independently 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; The q is selected from 1, 2, 3, or 4; b1 is selected from 0, 1, 2, 3, or 4; b2 is selected from 0, 1, 2, 3, 4, 5, or 6; b3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; b4 is selected from 0, 1, or 2; when there are two or more R... b At that time, two or more R b The same or different between each other, or two adjacent R b They connect with each other to form substituted or unsubstituted rings; The b'1 is selected from 0, 1, or 2; when there are two or more R... b At that time, two or more R b 'They are the same as or different from each other.'

[0053] More preferably, L1, L2, L3, L4, L5, and L6 are independently selected from single bonds or any one of the following groups:

[0054] The R b R b 'Independently selected from hydrogen, deuterium, fluorine, cyano, nitro, or substituted or unsubstituted groups of the following: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclocyclohep ...hepane, benzocyclohepane, benzocyclohepane, benzocyclohepane, benzocyclohepane, benzocyclohepane, benzocyclohepane, benzocyclohepane, benzocyclohepane, benzocyclohepane, benzocyclohepane, Butenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthraceneyl, phenanthrene, triphenylene, pyrene, perylene, pyridyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thiophene, benzothiophene, dibenzothiophene, benzodibenzothiophene, pyrroleyl Any one of the following: indolyl, carbazolyl, oxazolyl, benzoxazolyl, dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzoimidazolyl, dibenzoimidazolyl, quinolinyl, benzoquinolinyl, isoquinolinyl, benzoisoquinolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenantholinyl, naphridyl, acridineyl, phenoxazinyl, phenothiazinyl; The R p R qThe group independently selected from hydrogen, deuterium, fluorine, cyano, nitro, or substituted or unsubstituted groups of the following: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl The following are all of the following: silyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyrene, perylene, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, and triazinyl; The R s The following groups, independently selected from hydrogen, deuterium, substituted or unsubstituted, are allowed: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl. The following are all of the following: vinyl dimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyrene, perylene, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, and triazinyl; b'1 is selected from 0, 1, or 2; b'2 is selected from 0, 1, 2, 3, or 4; b'3 is selected from 0, 1, 2, 3, 4, 5, or 6; b'4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; b'5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; when there are two or more R b At that time, two or more R b 'They are the same as or different from each other.'

[0055] More preferably, L1, L2, L3, L4, L5, and L6 are independently selected from single bonds or any one of the following groups: .

[0056] Most preferably, formula I is selected from any of the following structures: 。

[0057] The above lists some specific structural forms of aromatic amine compounds represented by chemical formula I according to the present invention. However, the present invention is not limited to these listed chemical structures. Any structure based on the structure shown in chemical formula I, with substituents as defined above, should be included.

[0058] The present invention provides an organic electroluminescent device, comprising an anode, a cathode, and an organic layer, wherein the organic layer is located between the anode and the cathode or on the side of the cathode away from the anode, and the organic layer comprises at least one of the aromatic amine compounds described in the present invention.

[0059] Preferably, the organic layer is located between the anode and the cathode, and the organic layer comprises at least one of a hole transport layer and a light-emitting layer, wherein at least one of the hole transport layer and the light-emitting layer comprises at least one of the aromatic amine compounds described in this invention.

[0060] Preferably, the hole transport layer comprises a first hole transport layer and a second hole transport layer, the first hole transport layer being located between the anode and the light-emitting layer, the second hole transport layer being located between the first hole transport layer and the light-emitting layer, and at least one of the first hole transport layer and the second hole transport layer comprising at least one of the aromatic amine compounds described in this invention.

[0061] Preferably, the hole transport layer comprises a first hole transport layer, a second hole transport layer, and a third hole transport layer. The first hole transport layer is located between the anode and the light-emitting layer, the second hole transport layer is located between the first hole transport layer and the light-emitting layer, and the third hole transport layer is located between the second hole transport layer and the light-emitting layer. At least one of the first hole transport layer, the second hole transport layer, and the third hole transport layer comprises at least one of the aromatic amine compounds described in this invention.

[0062] 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.

[0063] More preferably, the covering layer comprises a first covering layer and a second covering layer, the first covering layer being located on the side of the cathode opposite to the anode, the second covering layer being located on the side of the first covering layer opposite to the anode, and at least one of the first covering layer and the second covering layer comprising at least one of the aromatic amine compounds described in this invention.

[0064] More preferably, the capping layer comprises a first capping layer, a second capping layer, and a third capping layer, wherein the first capping layer is located on the side of the cathode opposite to the anode, the second capping layer is located on the side of the first capping layer opposite to the anode, and the third capping layer is located on the side of the second capping layer opposite to the anode, and at least one of the first capping layer, the second capping layer, and the third capping layer comprises at least one of the aromatic amine compounds described in this invention.

[0065] The cathode of this invention is preferably made of a material with a low work function. The cathode materials of this invention include, but are not limited to, metals, metal alloys, conductive compounds, and mixtures thereof. Specific examples of the cathode materials include, but are not limited to, silver (Ag), magnesium (Mg), lithium (Li), aluminum (Al), gold (Au), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag).

[0066] The electron injection layer described in this invention is preferably made of a material with high electron injection properties, including metals, metal salts, and metal oxides. The electron injection materials include, but are not limited to, lithium (Li), cesium (Cs), lithium 8-hydroxyquinoline (Liq), cesium carbonate (Cs₂CO₃), lithium oxide (Li₂O), lithium boron oxide (LiBO₂), aluminum oxide (Al₂O₃), vanadium oxide (V₂O₅), barium oxide (BaO), lithium fluoride (LiF), sodium fluoride (NaF), rubidium fluoride (RbF), cesium fluoride (CsF), and magnesium phosphide (MgP).

[0067] The electron transport layer described in this invention is preferably made of a material with high electron transport properties. These include pyridine derivatives, imidazole derivatives, phenanthroline derivatives, metal complexes, oxadiazole derivatives, and triazole derivatives. The electron transport materials include, but are not limited to, bis(2-methyl-8-hydroxyquinoline)(4-phenylphenol)aluminum(III) (BAlq), tris(8-hydroxyquinoline)aluminum(III) (Alq3), 3,3'-[5'-[3-(3-pyridyl)phenyl](TmPyPB), 1,3,5-tris(N-phenyl-2-benzimidazole)benzene (TPBi), 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (PBD), 3-(biphenyl-4-yl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (TAZ), 4,7-diphenyl-1,10-phenanthroline (Bphen), and bis(10-hydroxybenzo[h]quinoline)beryllium (BeBq2), etc.

[0068] The hole-blocking layer described in this invention can typically be formed under the same conditions as the hole injection layer. 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, polymers, rare earth derivatives, etc. Specific examples of the hole-blocking layer material include, but are not limited to, BAlq, TPBi, and BCP.

[0069] The luminescent layer of this invention may include a single material, a host material (also called a matrix material), and a guest material (also called a dopant material). The luminescent layer material may contain multiple host materials and multiple guest materials. The guest material can be a fluorescent material, a phosphorescent material, or a TADF material. Fluorescent dopant materials may include: fused-ring amine derivatives, boron-containing compounds, pyrrole derivatives, indole derivatives, carbazole derivatives, fused polycyclic aromatic derivatives, styrene-based amine derivatives, etc., such as DPAVBi, C545T, BCzVBi, etc. Phosphorescent dopant materials may include: heavy metal complexes, phosphorescent rare-earth metal complexes, etc., such as FIrpic, F2Irpic, Ir(ppy)3, Ir(ppy)2(acac), etc. Host materials may include fused aromatic ring derivatives, heterocyclic compounds, etc. Fused aromatic ring derivatives include phenanthrene derivatives, fluoranthene derivatives, anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentanebenzene derivatives, etc., as well as heterocyclic compounds including carbazole derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, pyrimidine derivatives, etc., such as CBP, TCTA, AND, Alq3, BAlq, TPBi, TPD, etc., but are not limited to these.

[0070] The electron blocking layer of this invention is preferably made of materials with good hole transport capability and electron blocking capability. These include aromatic amine derivatives, carbazole derivatives, etc. Specific examples of the electron blocking materials, in addition to the aromatic amine compounds provided by this invention, 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., but are not limited thereto. The aromatic amine compounds of this invention are preferred.

[0071] The hole transport layer described in this invention is preferably made of a material with high hole transport properties, including aromatic amine derivatives, biphenyl diamine derivatives, carbazole derivatives, fluorene derivatives, etc. Specific examples of the hole transport materials, in addition to using the aromatic amine compounds provided by this invention, include, but are not limited to, N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), N4,N4,N4',N4'-tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine, 4,4'-cyclohexylbis[N,N-di(4-methylphenyl)aniline] (TAPC), N,N'-diphenyl-N,N'-di(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), 2,2,7,7-tetra(diphenylamino)-9,9-spirodifluorene (Spiro-TAD), and 4,4',4'-tris(carbazole-9-yl)triphenylamine (TCTA), etc. The aromatic amine compounds of this invention are preferred.

[0072] The hole injection layer described in this invention is preferably made of a material with high hole injectability. This includes metal compounds, aromatic amine derivatives, polycyano conjugated organic compounds, polymers, etc. Specific examples of the hole injection material, in addition to the aromatic amine compounds provided in this invention, include, but are not limited to, 1,4,5,8,9,11-hexaazabenzonitrile (HAT-CN), 4,4',4''-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4”-tris(N-3-methylphenyl-N-phenylamino)triphenylamine (m-MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (DPAB), 4,4'-bis(N-{4 The following compounds are preferred: [N'-(3-methylphenyl)-N'-phenylamino]phenyl-N-phenylamino)biphenyl (DNTPD), molybdenum trioxide (MoO3), vanadium pentoxide (V2O5), tungsten trioxide (WO3), nickel oxide (NiO), titanium dioxide (TiO2), copper phthalocyanine (CuPc), titanium phthalocyanine (TiOPC), 4,4',4”-tris[2-naphthylphenylamino]triphenylamine (2T-NATA), poly(3,4-ethylenedioxythiophene) / poly(styrene sulfonic acid) (PEDOT / PSS), etc. Aromatic amine compounds of the present invention are preferred.

[0073] The anode material preferred in this invention has a high work function, including metals, alloys, conductive compounds, and mixtures thereof. Specific examples include, but are not limited to, indium tin oxide (ITO), indium zinc oxide (IZO), indium oxide (InO), zinc oxide (ZnO), zinc oxide:aluminum (ZnO / Al), silver / indium tin oxide (Ag / ITO), indium tin oxide / silver / indium tin oxide (ITO / Ag / ITO), aluminum / nickel (Al / Ni), aluminum / platinum (Al / Pt), gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), and titanium (Ti).

[0074] The capping material described in this invention is preferably a material with photocoupling properties. Specific examples of the capping material, besides using the aromatic amine compounds provided in this invention, include aromatic amine derivatives, imidazole derivatives, thiazole derivatives, oxazole derivatives, etc. Specific examples of the capping material 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.

[0075] The following is one method for preparing the compound represented by chemical formula I of this invention, but the preparation method of this invention is not limited thereto. The core structure of the compound of chemical formula I can be prepared by the reaction route shown below. 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.

[0076] [Synthesis Route]

[0077] Preparation of compound I:

[0078] when , Similarly, the compound of formula I is prepared via the following route:

[0079] when , , Similarly, the compound of formula I is prepared via the following route:

[0080] Xa, Xb, Xc, Xd, Xe, Xf, Xg, Xh, and Xi are each 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, R1, R2, and R3 are the same as those described above.

[0081] Description of raw materials, reagents, and characterization equipment: The present invention does not impose any particular restrictions on the source of raw materials and reagents used in the following embodiments, which can be commercially available products or prepared using preparation methods well known to those skilled in the art.

[0082] Mass spectrometry was performed using a Waters G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer, with chloroform as the solvent. Elemental analysis was performed using a VarioELcube organic elemental analyzer from Elementar GmbH, Germany, with sample masses ranging from 5 to 10 mg.

[0083] [Synthetic Example 1] Synthesis of Compound 22

[0084] Synthetic intermediate A-22

[0085] Under nitrogen protection, a-22 (32.11 g, 150.00 mmol), b-22 (13.97 g, 150.00 mmol), and sodium tert-butoxide (21.62 g, 225.00 mmol) dissolved in 750 mL toluene were added to a reaction flask. Pd(dppf)Cl2 (1.32 g, 1.8 mmol) was added with stirring, and the mixture was heated to reflux for 4.5 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 (28.85 g, 85% yield); HPLC purity ≥ 99.74%. Mass spectrometry m / z: 226.0554 (theoretical value: 226.0565).

[0086] Synthetic intermediate B-22

[0087] Under nitrogen protection, c-22 (24.30 g, 108.00 mmol), d-22 (11.57 g, 108.00 mmol), and sodium tert-butoxide (15.57 g, 162.00 mmol) dissolved in 600 mL of toluene were added to a reaction flask with stirring. Pd(OAc)2 (0.24 g, 1.08 mmol) and P(t-Bu)3 (4.32 mL, 2.16 mmol, in 0.5 M toluene solution) were then added. The mixture of the above reactants was heated under reflux for 5.5 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 / methanol (7:1 v / v) yielded intermediate B-22 (22.25 g, 82% yield); HPLC purity ≥ 99.81%. Mass spectrometry m / z: 251.0936 (theoretical value: 251.0922).

[0088] Synthetic intermediate C-22

[0089] Under nitrogen protection, e-22 (16.34 g, 72.00 mmol), A-22 (16.29 g, 72.00 mmol), and sodium tert-butoxide (10.38 g, 108.00 mmol) dissolved in 432 mL of toluene were added to a reaction flask with stirring. Pd(OAc)2 (0.16 g, 0.72 mmol) and P(t-Bu)3 (2.88 mL, 1.44 mmol, 0.5 M toluene solution) were then added. The mixture of the above reactants was heated under reflux for 6.5 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 give intermediate C-22 (20.91 g, 78% yield); HPLC purity ≥ 99.85%. Mass spectrometry m / z: 371.0174 (theoretical value: 371.0161).

[0090] Synthetic compound 22

[0091] Under nitrogen protection, C-22 (13.40 g, 36.00 mmol), B-22 (18.09 g, 72.00 mmol), and sodium tert-butoxide (6.92 g, 72.00 mmol) dissolved in 240 mL of toluene were added to a reaction flask. Pd₂(dba)₃ (0.66 g, 0.72 mmol) and X-Phos (0.34 g, 0.72 mmol) were added with stirring. The mixture of the above reactants was heated under reflux for 7 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 22 (21.07 g, 73%). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 801.2487 (theoretical value: 801.2471). Theoretical elemental content (%) C 47 H 33 DF6N4S: C, 70.40; H, 4.40; N, 6.99. Measured elemental content (%): C, 70.44; H, 4.43; N, 7.03.

[0092] [Synthetic Example 2] Synthesis of Compound 76

[0093] According to the preparation method in Synthesis Example 1, a-22 was replaced with an equimolar amount of c-22, b-22 with an equimolar amount of b-76, c-22 with an equimolar amount of c-76, d-22 with an equimolar amount of b-22, and e-22 with an equimolar amount of e-76, yielding compound 76 (20.11 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 775.2880 (theoretical value: 775.2892). Theoretical elemental content (%) C 51 H 32 D2F3N5: C, 78.95; H, 4.68; N, 9.03. Measured elemental content (%): C, 78.94; H, 4.66; N, 9.00.

[0094] [Synthetic Example 3] Synthesis of Compound 93

[0095] According to the preparation method in Synthesis Example 1, a-22 was replaced with an equimolar amount of a-93, d-22 was replaced with an equimolar amount of b-22, and e-22 was replaced with an equimolar amount of e-93, yielding compound 93 (18.89 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 718.2623 (theoretical value: 718.2610). Theoretical elemental content (%) C 44 H 28D3F6N3: C, 73.53; H, 4.77; N, 5.85. Measured elemental content (%): C, 73.55; H, 4.79; N, 5.87.

[0096] [Synthetic Example 4] Synthesis of Compound 95

[0097] Synthetic intermediate B-95

[0098] Under nitrogen protection, c-95 (33.75 g, 150.00 mmol), b-22 (13.97 g, 150.00 mmol), and sodium tert-butoxide (21.62 g, 225.00 mmol) dissolved in 750 mL toluene were added to a reaction flask. Pd(dppf)Cl2 (1.32 g, 1.80 mmol) was added with stirring, and the mixture was heated to reflux for 4.5 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 B-95 (29.53 g, 83% yield); HPLC purity ≥ 99.72%. Mass spectrometry m / z: 237.0752 (theoretical value: 237.0765).

[0099] Synthetic compound 95

[0100] Under nitrogen protection, e-95 (11.44 g, 36.00 mmol), B-95 (25.62 g, 108.00 mmol), and sodium tert-butoxide (10.38 g, 108.00 mmol) dissolved in 450 mL of toluene were added to a reaction flask with stirring. Pd₂(dba)₃ (0.99 g, 1.08 mmol) and X-Phos (0.51 g, 1.08 mmol) were then added. The mixture of the above reactants was heated under reflux for 8.5 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 95 (19.54 g, 69% yield). HPLC analysis showed a solid purity ≥ 99.91%. Mass spectrometry m / z: 786.2471 (theoretical value: 786.2484). Theoretical elemental content (%) C 45 H 27 D3F9N3: C, 68.70; H, 4.23; N, 5.34. Measured elemental content (%): C, 68.72; H, 4.25; N, 5.37.

[0101] [Synthetic Example 5] Synthesis of Compound 114

[0102] According to the preparation method in Synthesis Example 1, a-22 was replaced with an equimolar amount of c-22, c-22 was replaced with an equimolar amount of c-114, d-22 was replaced with an equimolar amount of b-22, and e-22 was replaced with an equimolar amount of e-93, yielding compound 114 (20.52 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 802.3380 (theoretical value: 802.3363). Theoretical elemental content (%) C 55 H 37 D3F3N3: C, 82.27; H, 5.40; N, 5.23. Measured elemental content (%): C, 82.29; H, 5.43; N, 5.25.

[0103] [Synthetic Example 6] Synthesis of Compound 118

[0104] According to the preparation method in Synthesis Example 1, a-22 was replaced with an equimolar amount of a-118, b-22 with an equimolar amount of b-76, c-22 with an equimolar amount of a-93, d-22 with an equimolar amount of b-22, and e-22 with an equimolar amount of e-93, yielding compound 118 (20.03 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 794.2941 (theoretical value: 794.2923). Theoretical elemental content (%) C 50 H 32 D3F6N3: C, 75.55; H, 4.82; N, 5.29. Measured elemental content (%): C, 75.56; H, 4.83; N, 5.31.

[0105] [Synthetic Example 7] Synthesis of Compound 143

[0106] According to the preparation method in Synthesis Example 1, a-22 was replaced with an equimolar amount of c-22, b-22 with an equimolar amount of b-143, c-22 with an equimolar amount of a-93, d-22 with an equimolar amount of b-22, and e-22 with an equimolar amount of e-93, yielding compound 143 (18.65 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 750.3063 (theoretical value 750.3050). Theoretical elemental content (%) C 51 H 33 D3F3N3: C, 81.58; H, 5.23; N, 5.60. Measured elemental content (%): C, 81.59; H, 5.26; N, 5.65.

[0107] [Synthetic Example 8] Synthesis of Compound 163

[0108] According to the preparation method in Synthesis Example 1, a-22 was replaced with an equimolar amount of a-163, b-22 with an equimolar amount of b-163, c-22 with an equimolar amount of a-93, d-22 with an equimolar amount of b-22, and e-22 with an equimolar amount of e-93, yielding compound 163 (20.64 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 842.3664 (theoretical value: 842.3676). Theoretical elemental content (%) C 58 H 41 D3F3N3: C, 82.64; H, 5.62; N, 4.98. Measured elemental content (%): C, 82.62; H, 5.59; N, 4.96.

[0109] [Synthetic Example 9] Synthesis of Compound 194

[0110] According to the preparation method in Synthesis Example 1, a-22 was replaced with an equimolar amount of a-194, b-22 with an equimolar amount of b-194, c-22 with an equimolar amount of a-93, d-22 with an equimolar amount of b-22, and e-22 with an equimolar amount of e-93, yielding compound 194 (20.46 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 767.2968 (theoretical value: 767.2951). Theoretical elemental content (%) C 50 H 32 D3F3N4O: C, 78.21; H, 4.99; N, 7.30. Measured elemental content (%): C, 78.26; H, 5.02; N, 7.33.

[0111] [Synthetic Example 10] Synthesis of Compound 198

[0112] According to the preparation method in Synthesis Example 1, a-22 was replaced with an equimolar amount of a-198, d-22 was replaced with an equimolar amount of b-22, and e-22 was replaced with an equimolar amount of e-93, yielding compound 198 (21.34 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 834.3225 (theoretical value: 834.3236). Theoretical elemental content (%) C 53 H 36 D3F6N3: C, 76.24; H, 5.07; N, 5.03. Measured elemental content (%): C, 76.22; H, 5.04; N, 5.02.

[0113] [Synthetic Example 11] Synthesis of Compound 215

[0114] According to the preparation method in Synthesis Example 1, a-22 was replaced with an equimolar amount of c-22, c-22 was replaced with an equimolar amount of c-215, d-22 was replaced with an equimolar amount of b-22, and e-22 was replaced with an equimolar amount of e-93, yielding compound 215 (20.82 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 862.2482 (theoretical value: 862.2491). Theoretical elemental content (%) C 55 H 33 D3F3N3S2: C, 76.54; H, 4.55; N, 4.87. Measured elemental content (%): C, 76.52; H, 4.53; N, 4.86.

[0115] [Synthetic Example 12] Synthesis of Compound 222

[0116] According to the preparation method in Synthesis Example 1, a-22 was replaced with an equimolar amount of a-222, b-22 with an equimolar amount of b-194, c-22 with an equimolar amount of a-93, d-22 with an equimolar amount of b-22, and e-22 with an equimolar amount of e-93, yielding compound 222 (21.50 g). HPLC analysis showed a solid purity ≥ 99.91%. Mass spectrometry m / z: 904.3452 (theoretical value: 904.3468). Theoretical elemental content (%) C 62 H 39 D3F3N3O: C, 82.28; H, 5.01; N, 4.64. Measured elemental content (%): C, 82.26; H, 4.98; N, 4.61.

[0117] [Synthetic Example 13] Synthesis of Compound 237

[0118] According to the preparation method in Synthesis Example 1, a-22 was replaced with an equimolar amount of a-237, b-22 with an equimolar amount of b-194, c-22 with an equimolar amount of a-93, d-22 with an equimolar amount of b-22, and e-22 with an equimolar amount of e-93, yielding compound 237 (20.08 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 796.3845 (theoretical value: 796.3832). Theoretical elemental content (%) C 54 H 43D3F3N3: C, 81.38; H, 6.20; N, 5.27. Measured elemental content (%): C, 81.39; H, 6.22; N, 5.28.

[0119] [Synthetic Example 14] Synthesis of Compound 242

[0120] According to the preparation method in Synthesis Example 1, a-22 was replaced with an equimolar amount of a-242, b-22 with an equimolar amount of b-194, c-22 with an equimolar amount of c-242, d-22 with an equimolar amount of b-22, and e-22 with an equimolar amount of e-93, yielding compound 242 (19.07 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 778.3376 (theoretical value: 778.3363). Theoretical elemental content (%) C 53 H 37 D3F3N3: C, 81.72; H, 5.56; N, 5.39. Measured elemental content (%): C, 81.76; H, 5.57; N, 5.42.

[0121] [Synthetic Example 15] Synthesis of Compound 293

[0122] According to the preparation method in Synthesis Example 1, a-22 was replaced with an equimolar amount of c-22, c-22 was replaced with an equimolar amount of c-293, d-22 was replaced with an equimolar amount of b-22, and e-22 was replaced with an equimolar amount of e-93, yielding compound 293 (18.29 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 686.2559 (theoretical value: 686.2548). Theoretical elemental content (%) C 43 H 27 D3F5N3: C, 75.21; H, 4.84; N, 6.12. Measured elemental content (%): C, 75.26; H, 4.88; N, 6.16.

[0123] [Synthetic Example 16] Synthesis of Compound 295

[0124] According to the preparation method in Synthesis Example 1, a-22 was replaced with an equimolar amount of a-295, b-22 with an equimolar amount of b-76, c-22 with an equimolar amount of c-295, d-22 with an equimolar amount of b-22, and e-22 with an equimolar amount of e-93, yielding compound 295 (22.61 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 896.3596 (theoretical value: 896.3581). Theoretical elemental content (%) C 61 H 40 D3F4N3: C, 81.68; H, 5.17; N, 4.68. Measured elemental content (%): C, 81.71; H, 5.19; N, 4.70.

[0125] [Synthetic Example 17] Synthesis of Compound 337

[0126] According to the preparation method in Synthesis Example 1, a-22 was replaced with an equimolar amount of c-22, b-22 with an equimolar amount of b-76, c-22 with an equimolar amount of c-337, d-22 with an equimolar amount of b-22, and e-22 with an equimolar amount of e-93, yielding compound 337 (19.10 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 736.3689 (theoretical value: 736.3677). Theoretical elemental content (%) C 49 H 23 D 13 F3N3: C, 79.86; H, 6.70; N, 5.70. Measured elemental content (%): C, 79.88; H, 6.74; N, 5.73.

[0127] [Synthetic Example 18] Synthesis of Compound 362

[0128] According to the preparation method in Synthesis Example 4, c-95 was replaced with an equimolar amount of c-293, b-22 with an equimolar amount of b-362, and e-95 with an equimolar amount of e-362, yielding compound 362 (20.91 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 784.2910 (theoretical value: 784.2924). Theoretical elemental content (%) C 54 H 35 DF3N3: C, 82.63; H, 4.75; N, 5.35. Measured elemental content (%): C, 82.59; H, 4.72; N, 5.33.

[0129] [Synthetic Example 19] Synthesis of Compound 501

[0130] According to the preparation method in Synthesis Example 1, a-22 was replaced with an equimolar amount of a-501, c-22 with an equimolar amount of c-501, d-22 with an equimolar amount of b-22, and e-22 with an equimolar amount of e-93, yielding compound 501 (22.08 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 888.2379 (theoretical value: 888.2390). Theoretical elemental content (%) C 52 H 26 D3F 10 N3: C, 70.27; H, 3.63; N, 4.73. Measured elemental content (%): C, 70.25; H, 3.62; N, 4.70.

[0131] [Synthetic Example 20] Synthesis of Compound 521

[0132] According to the preparation method in Synthesis Example 1, a-22 was replaced with an equimolar amount of a-521, c-22 with an equimolar amount of c-521, d-22 with an equimolar amount of b-22, and e-22 with an equimolar amount of e-93, yielding compound 521 (18.97 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 731.2769 (theoretical value: 731.2751). Theoretical elemental content (%) C 47 H 29 D3F4N4: C, 77.14; H, 4.82; N, 7.66. Measured elemental content (%): C, 77.16; H, 4.86; N, 7.67.

[0133] [Synthetic Example 21] Synthesis of Compound 528

[0134] According to the preparation method in Synthesis Example 1, a-22 was replaced with an equimolar amount of a-528, c-22 with an equimolar amount of c-501, d-22 with an equimolar amount of b-22, and e-22 with an equimolar amount of e-93, yielding compound 528 (20.52 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 802.1885 (theoretical value: 802.1870). Theoretical elemental content (%) C 44 H 20 D3F 10 N3O: C, 65.84; H, 3.26; N, 5.24. Measured elemental content (%): C, 65.86; H, 3.29; N, 5.27.

[0135] [Synthetic Example 22] Synthesis of Compound 569

[0136] According to the preparation method in Synthesis Example 4, c-95 was replaced with an equimolar amount of c-501, and b-22 was replaced with an equimolar amount of d-22, yielding compound 569 (22.87 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 894.1907 (theoretical value: 894.1919). Theoretical elemental content (%) C 45 H 21 D3F 15 N3: C, 60.41; H, 3.04; N, 4.70. Measured elemental content (%): C, 60.37; H, 3.01; N, 4.67.

[0137] [Synthetic Example 23] Synthesis of Compound 589

[0138] According to the preparation method in Synthesis Example 1, a-22 was replaced with an equimolar amount of a-589, b-22 with an equimolar amount of d-22, c-22 with an equimolar amount of c-501, d-22 with an equimolar amount of b-22, and e-22 with an equimolar amount of e-93, yielding compound 589 (22.72 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 941.2669 (theoretical value: 941.2656). Theoretical elemental content (%) C 55 H 29 D3F 10 N4: C, 70.14; H, 3.75; N, 5.95. Measured elemental content (%): C, 70.16; H, 3.79; N, 5.98.

[0139] [Synthetic Example 24] Synthesis of Compound 596

[0140] According to the preparation method in Synthesis Example 1, a-22 was replaced with an equimolar amount of a-93, c-22 with an equimolar amount of c-501, d-22 with an equimolar amount of d-596, and e-22 with an equimolar amount of e-93, yielding compound 596 (22.68 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 874.3187 (theoretical value: 874.3173). Theoretical elemental content (%) C 50 H 36 D3F 10N3: C, 68.64; H, 4.84; N, 4.80. Measured elemental content (%): C, 68.66; H, 4.88; N, 4.83.

[0141] [Synthetic Example 25] Synthesis of Compound 649

[0142] According to the preparation method in Synthesis Example 1, a-22 was replaced with an equimolar amount of c-337, b-22 with an equimolar amount of b-649, c-22 with an equimolar amount of c-293, d-22 with an equimolar amount of b-22, and e-22 with an equimolar amount of e-93, yielding compound 649 (19.42 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 738.3426 (theoretical value: 738.3410). Theoretical elemental content (%) C 50 H 28 D8F2N4: C, 81.27; H, 6.00; N, 7.58. Measured elemental content (%): C, 81.29; H, 6.06; N, 7.62.

[0143] [Synthetic Example 26] Synthesis of Compound 664

[0144] According to the preparation method in Synthesis Example 1, a-22 was replaced with an equimolar amount of a-664, d-22 was replaced with an equimolar amount of b-22, and e-22 was replaced with an equimolar amount of e-664, yielding compound 664 (21.46 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 863.3688 (theoretical value: 863.3674). Theoretical elemental content (%) C 55 H 47 F6N3: C, 76.46; H, 5.48; N, 4.86. Measured elemental content (%): C, 76.48; H, 5.49; N, 4.87.

[0145] [Synthetic Example 27] Synthesis of Compound 700

[0146] According to the preparation method in Synthesis Example 1, a-22 was replaced with an equimolar amount of a-163, b-22 with an equimolar amount of b-700, c-22 with an equimolar amount of c-337, d-22 with an equimolar amount of b-22, and e-22 with an equimolar amount of e-700, yielding compound 700 (21.47 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 851.3922 (theoretical value: 851.3908). Theoretical elemental content (%) C 57 H 32 D 10 F3N3O: C, 80.35; H, 6.15; N, 4.93. Measured elemental content (%): C, 80.36; H, 6.18; N, 4.97.

[0147] [Synthetic Example 28] Synthesis of Compound 722

[0148] According to the preparation method in Synthesis Example 1, a-22 was replaced with an equimolar amount of a-722, b-22 with an equimolar amount of b-194, c-22 with an equimolar amount of c-242, d-22 with an equimolar amount of b-22, and e-22 with an equimolar amount of e-722, yielding compound 722 (23.06 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 955.4101 (theoretical value: 955.4113). Theoretical elemental content (%) C 67 H 52 F3N3: C, 84.16; H, 5.48; N, 4.39. Measured elemental content (%): C, 84.13; H, 5.46; N, 4.34.

[0149] [Synthetic Example 29] Synthesis of Compound 729

[0150] Synthetic intermediate A-729

[0151] According to the preparation method in Synthesis Example 1, a-22 was replaced with an equimolar amount of a-729 to obtain synthetic intermediate A-729 (43.51 g, 86%). The purity of the solid was ≥99.68% as determined by HPLC. Mass spectrometry m / z: 337.1279 (theoretical value: 337.1265).

[0152] Synthetic intermediate A-93

[0153] According to the preparation method in Synthesis Example 1, a-22 was replaced with an equimolar amount of a-93 to obtain synthetic intermediate A-93 (21.32 g, 84%), and the solid purity was ≥99.72% as determined by HPLC. Mass spectrometry m / z: 169.0875 (theoretical value: 169.0891).

[0154] Synthetic intermediate D-729

[0155] According to the preparation method in Synthesis Example 1, a-22 was replaced with an equimolar amount of f-729 to obtain synthetic intermediate D-729 (28.05 g, 83%). The purity of the solid was ≥99.74% as determined by HPLC. Mass spectrometry m / z: 225.1501 (theoretical value: 225.1517).

[0156] Synthetic intermediate C-729

[0157] According to the preparation method in Synthesis Example 1, e-22 was replaced with an equimolar amount of e-729, and A-22 was replaced with an equimolar amount of A-729 to obtain synthetic intermediate C-729 (45.33 g, yield 82%); HPLC purity ≥ 99.76%. Mass spectrometry m / z: 551.0463 (theoretical value: 551.0450).

[0158] Synthetic intermediate E-729

[0159] Under nitrogen protection, C-729 (41.46 g, 75.00 mmol), A-93 (12.69 g, 75.00 mmol), and sodium tert-butoxide (10.81 g, 112.50 mmol) dissolved in 450 mL of toluene were added to a reaction flask with stirring. Pd(OAc)₂ (0.17 g, 0.75 mmol) and P(t-Bu)₃ (3.00 mL, 1.50 mmol, 0.5 M toluene solution) were then added. The mixture of the above reactants was heated under reflux for 6 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 give intermediate E-729 (37.50 g, 78% yield); HPLC purity ≥ 99.83%. Mass spectrometry m / z: 640.2096 (theoretical value: 640.2080).

[0160] Synthetic compound 729

[0161] Under nitrogen protection, E-729 (23.08 g, 36.00 mmol), D-729 (8.11 g, 36.00 mmol), and sodium tert-butoxide (3.46 g, 36.00 mmol) dissolved in 150 mL of toluene were added to a reaction flask with stirring. Pd₂(dba)₃ (0.33 g, 0.36 mmol) and X-Phos (0.17 g, 0.36 mmol) were then added. The mixture of the above reactants was heated under reflux for 7 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 729 (21.10 g, 72%). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 813.3536 (theoretical value: 813.3518). Theoretical elemental content (%) C 51 H 45 F6N3: C, 75.26; H, 5.57; N, 5.16. Measured elemental content (%): C, 75.29; H, 5.61; N, 5.17.

[0162] [Synthetic Example 30] Synthesis of Compound 731

[0163] According to the preparation method in Synthesis Example 4, c-95 was replaced with an equimolar amount of c-22, b-22 was replaced with an equimolar amount of d-596, and e-95 was replaced with an equimolar amount of e-731, yielding compound 731 (23.98 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 993.4657 (theoretical value: 993.4644). Theoretical elemental content (%) C 60 H 60 F9N3: C, 72.49; H, 6.08; N, 4.23. Measured elemental content (%): C, 72.52; H, 6.11; N, 4.28.

[0164] [Synthetic Example 31] Synthesis of Compound 741

[0165] According to the preparation method in Synthesis Example 1, a-22 was replaced with an equimolar amount of a-741, b-22 with an equimolar amount of b-194, c-22 with an equimolar amount of c-741, d-22 with an equimolar amount of b-22, and e-22 with an equimolar amount of e-722, yielding compound 741 (22.71 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 913.3700 (theoretical value: 913.3711). Theoretical elemental content (%) C 58 H 54F3N3S2: C, 76.20; H, 5.95; N, 4.60. Measured elemental content (%): C, 76.16; H, 5.92; N, 4.57.

[0166] [Synthetic Example 32] Synthesis of Compound 757

[0167] According to the preparation method in Synthesis Example 1, a-22 was replaced with an equimolar amount of c-22, c-22 was replaced with an equimolar amount of c-757, d-22 was replaced with an equimolar amount of b-22, and e-22 was replaced with an equimolar amount of e-722, yielding compound 757 (21.92 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 833.3797 (theoretical value: 833.3808). Theoretical elemental content (%) C 52 H 54 F3N3Si2: C, 74.87; H, 6.53; N, 5.04. Measured elemental content (%): C, 74.85; H, 6.52; N, 5.03.

[0168] [Synthetic Example 33] Synthesis of Compound 811

[0169] According to the preparation method in Synthesis Example 1, a-22 was replaced with an equimolar amount of c-501, c-22 with an equimolar amount of f-729, d-22 with an equimolar amount of b-22, and e-22 with an equimolar amount of e-811, yielding compound 811 (21.83 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 853.3838 (theoretical value: 853.3851). Theoretical elemental content (%) C 53 H 52 F5N3Si: C, 74.53; H, 6.14; N, 4.92. Measured elemental content (%): C, 74.50; H, 6.11; N, 4.88.

[0170] [Synthetic Example 34] Synthesis of Compound 818

[0171] According to the preparation method in Synthesis Example 1, a-22 was replaced with an equimolar amount of a-93, and e-22 was replaced with an equimolar amount of e-818 to obtain compound 818 (20.39 g). HPLC analysis showed that the solid purity was ≥99.95%. Mass spectrometry m / z: 797.2440 (theoretical value: 797.2453). Theoretical elemental content (%) C 46 H 32F9N3: C, 69.26; H, 4.04; N, 5.27. Measured elemental content (%): C, 69.22; H, 4.01; N, 5.25.

[0172] [Synthetic Example 35] Synthesis of Compound 828

[0173] According to the preparation method in Synthesis Example 1, a-22 was replaced with an equimolar amount of c-501, b-22 with an equimolar amount of b-828, c-22 with an equimolar amount of a-93, d-22 with an equimolar amount of b-22, and e-22 with an equimolar amount of e-828, yielding compound 828 (20.14 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 776.2921 (theoretical value: 776.2938). Theoretical elemental content (%) C 49 H 37 F5N4: C, 75.76; H, 4.80; N, 7.21. Measured elemental content (%): C, 75.78; H, 4.83; N, 7.24.

[0174] [Synthetic Example 36] Synthesis of Compound 836

[0175] According to the preparation method in Synthesis Example 1, a-22 was replaced with an equimolar amount of c-22, b-22 with an equimolar amount of d-22, c-22 with an equimolar amount of a-93, d-22 with an equimolar amount of b-22, and e-22 with an equimolar amount of e-836, yielding compound 836 (19.39 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 737.3004 (theoretical value: 737.3018). Theoretical elemental content (%) C 50 H 38 F3N3: C, 81.39; H, 5.19; N, 5.69. Measured elemental content (%): C, 81.42; H, 5.23; N, 5.71.

[0176] [Synthetic Example 37] Synthesis of Compound 853

[0177] According to the preparation method in Synthesis Example 1, a-22 was replaced with an equimolar amount of a-729, b-22 with an equimolar amount of d-22, c-22 with an equimolar amount of a-93, d-22 with an equimolar amount of b-22, and e-22 with an equimolar amount of e-853, yielding compound 853 (20.91 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 806.2828 (theoretical value: 806.2844). Theoretical elemental content (%) C 50 H 36 F6N4: C, 74.43; H, 4.50; N, 6.94. Measured elemental content (%): C, 74.46; H, 4.54; N, 6.97.

[0178] [Synthetic Example 38] Synthesis of Compound 880

[0179] According to the preparation method in Synthesis Example 1, a-22 was replaced with an equimolar amount of c-501, b-22 with an equimolar amount of b-880, c-22 with an equimolar amount of a-93, d-22 with an equimolar amount of b-22, and e-22 with an equimolar amount of e-880, yielding compound 880 (20.19 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 824.3036 (theoretical value: 824.3018). Theoretical elemental content (%) C 54 H 33 D3F5N3: C, 78.63; H, 4.76; N, 5.09. Measured elemental content (%): C, 78.65; H, 4.77; N, 5.11.

[0180] [Synthetic Example 39] Synthesis of Compound 889

[0181] According to the preparation method in Synthesis Example 1, a-22 was replaced with an equimolar amount of c-22, b-22 with an equimolar amount of d-22, c-22 with an equimolar amount of a-93, d-22 with an equimolar amount of b-22, and e-22 with an equimolar amount of e-889, yielding compound 889 (18.87 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 717.3319 (theoretical value: 717.3331). Theoretical elemental content (%) C 48 H 42 F3N3: C, 80.31; H, 5.90; N, 5.85. Measured elemental content (%): C, 80.28; H, 5.87; N, 5.83.

[0182] [Synthetic Example 40] Synthesis of Compound 898

[0183] According to the preparation method in Synthesis Example 1, a-22 was replaced with an equimolar amount of c-22, b-22 with an equimolar amount of b-76, c-22 with an equimolar amount of b-242, d-22 with an equimolar amount of b-22, and e-22 with an equimolar amount of e-898, yielding compound 898 (20.72 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 833.3969 (theoretical value: 833.3957). Theoretical elemental content (%) C 57 H 50 F3N3: C, 82.09; H, 6.04; N, 5.04. Measured elemental content (%): C, 82.12; H, 6.09; N, 5.08.

[0184] [Device Examples]

[0185] A combined IVL testing system was used to test the luminous efficiency of organic electroluminescent devices (OLEDs), comprising testing software, a computer, a Keithley K2400 digital source meter, and a PhotoResearch PR788 spectral scanning luminance meter. Lifetime testing was performed using the McScience M6000 OLED lifetime testing system.

[0186] [Example 1]

[0187] The glass substrate was cleaned using distilled water and ultrasonic cleaning. After distilled water washing, ultrasonic cleaning was performed using solvents such as isopropanol, acetone, and methanol, followed by drying. After drying, the substrate was transferred to a plasma cleaner, and then transferred to an evaporation deposition machine. ITO / Ag / ITO was coated onto the glass substrate to form an anode. HI-1 was deposited on the anode to form a hole injection layer with a thickness of 450 Å. HT-1 was deposited on the hole injection layer to form a hole transport layer with a thickness of 1200 Å. A light-emitting layer was deposited on the hole transport layer, using GH-1 as the host material and doped with 6 wt% GD-1 to form a light-emitting layer with a thickness of 300 Å. ET-1:LiQ (mass ratio 1:1) was deposited on the light-emitting layer to form an electron transport layer with a thickness of 350 Å. LiF was deposited on the electron transport layer to form an electron injection layer with a thickness of 10 Å. Mg:Ag (mass ratio 1:9) was deposited on the electron injection layer to form a cathode with a thickness of 150 Å. CP-1 is deposited on the cathode layer to form a first capping layer with a thickness of 750 Å. Compound 22 of the present invention is then deposited on the first capping layer to form a second capping layer with a thickness of 250 Å. This forms an organic light-emitting device.

[0188]

[0189] [Examples 2-40]

[0190] Compound 76, 93, 95, 114, 118, 143, 163, 194, 198, 215, 222, 237, 242, 293, 295, 337, 362, 501, 521, 528, 569, 589, 596, 649, 664, 700, 722, 729, 731, 741, 757, 811, 818, 828, 836, 853, 880, 889, and 898 of the present invention were used to replace compound 22 in Example 1 as the second capping layer material. Otherwise, an organic electroluminescent device was prepared using the same preparation method as in Example 1.

[0191] [Comparative Examples 1-2]

[0192] Compounds P-1, P-2, and P-3 were used to replace compound 22 in device example 1 as the second capping layer material. Otherwise, an organic electroluminescent device was prepared using the same preparation method as device example 1.

[0193] The test environment was atmospheric, and the temperature was room temperature. The test results of the luminescence characteristics of the organic electroluminescent devices obtained by devices 1-40 and comparative examples 1-3 in the embodiments of the present invention are shown in Table 1 below.

[0194] Table 1:

[0195] As shown in Table 1, when the aromatic amine compounds of the present invention are applied to the second capping layer of organic electroluminescent devices, the devices exhibit higher luminous efficiency and longer lifespan compared to comparative compounds P-1 to P-2. The compounds of the present invention are high-performance capping layer materials.

[0196] [Example 41]

[0197] The glass substrate was cleaned using distilled water and ultrasonic cleaning. After distilled water washing, ultrasonic cleaning was performed using solvents such as isopropanol, acetone, and methanol, followed by drying. After drying, the substrate was transferred to a plasma cleaner, and then transferred to an evaporation deposition machine. Indium tin oxide (ITO) was coated onto the glass substrate to form an anode. HI-2 was deposited on the anode to form a hole injection layer with a thickness of 500 Å. HT-2 was deposited on the hole injection layer to form a first hole transport layer with a thickness of 1000 Å. Compound 22 of the present invention was deposited on the first hole transport layer to form a second hole transport layer with a thickness of 150 Å. A light-emitting layer was deposited on the second hole transport layer, using RH-2 as the host material and doped with 4 wt% RD-2 to form a light-emitting layer with a thickness of 300 Å. ET-2 was deposited on the light-emitting layer to form an electron transport layer with a thickness of 300 Å. LiF was deposited on the electron transport layer to form an electron injection layer with a thickness of 10 Å. Al is deposited on the electron injection layer to form a cathode with a thickness of 1200 Å, thus forming an organic light-emitting device.

[0198]

[0199] [Examples 42-80]

[0200] Compounds 76, 93, 95, 114, 118, 143, 163, 194, 198, 215, 222, 237, 242, 293, 295, 337, 362, 501, 521, 528, 569, 589, 596, 649, 664, 700, 722, 729, 731, 741, 757, 811, 818, 828, 836, 853, 880, 889, and 898 of the present invention were used to replace compound 22 in Example 41 as the second hole transport layer material. Otherwise, an organic electroluminescent device was prepared using the same preparation method as in Example 41.

[0201] [Comparative Examples 3-4]

[0202] Compounds P-3 and P-4 were used to replace compound 22 in Example 41 as the second hole transport layer material. Otherwise, an organic electroluminescent device was prepared using the same preparation method as in Example 41.

[0203] The test environment was atmospheric, and the temperature was room temperature. The luminescence characteristics of the organic electroluminescent devices obtained in embodiments 41-80 and comparative embodiments 3-4 are shown in Table 2 below.

[0204] Table 2:

[0205] As shown in Table 2, when the aromatic amine compounds of the present invention are applied to the second hole transport layer of organic electroluminescent devices, the devices exhibit higher luminous efficiency and longer lifespan compared to comparative compounds P-3 to P-4. The compounds of the present invention are high-performance materials for the second hole transport layer.

[0206] It should be noted that the present invention has been specifically described with reference to individual embodiments, but those skilled in the art can make various forms or details of improvements to the present invention without departing from the principles of the present invention, and these improvements also fall within the protection scope of the present invention.

Claims

1. An aromatic amine compound, characterized in that, The aromatic amine compound has the structure represented by Formula I: Wherein, Ar1, Ar2, 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, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl groups, substituted or unsubstituted C1-C25 heterocyclic alkanes and C6-C30 aromatic ring fused cycloyl groups, and substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl groups; R1, R2, and R3 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, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cycloyl groups; and at least one of R1, R2, and R3 is not selected from hydrogen; When at least one of R1, R2, and R3 is selected from deuterium, at least one of Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 is replaced by F or CF3; When R1, R2, and R3 are not selected from deuterium, at least one of Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 is substituted by F or CF3, and at least one of the remaining ones is substituted by any one of deuterium, C1-C25 alkyl groups, and C3-C25 cycloalkyl groups. The L1, L2, L3, L4, L5, and L6 are independently selected from any one of the following: single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C6-C30 heteroarylene, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, and substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic rings.

2. The aromatic amine compound according to claim 1, characterized in that, Formula I is selected from any of the following structures: The definitions of Ar1, Ar2, Ar3, Ar4, Ar5, Ar6, L1, L2, L3, L4, L5, L6, R1, R2, and R3 are the same as those in Equation I.

3. The aromatic amine compound according to claim 1, characterized in that, The Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 groups are independently selected from any one of the following groups; The v is independently selected from either CH or N; The ring A is selected from substituted or unsubstituted C3~C10 alicyclic rings; X1 and X2 are independently selected from O, S, and N(R). z Any one of the following; X3, X4, and X5 are independently selected from O, S, and C(R). x R y ), N(R z Any one of the following; The R a R a '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 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl; The R x R y 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, or R x R y The links between them form substituted or unsubstituted rings; The R z It is independently 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; a1 is selected from 0, 1, 2, 3, 4, or 5; a2 is selected from 0, 1, 2, 3, or 4; a3 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; a4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; a5 is selected from 0, 1, or 2; a6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; a7 is selected from 0, 1, 2, or 3; when there are two or more R... a At that time, two or more R a The same or different between each other, or two adjacent R a They connect with each other to form substituted or unsubstituted rings; The a'1 is selected from 0, 1, or 2; when there are two or more R a At that time, two or more R a 'They are the same as or different from each other.' 4. An aromatic amine compound according to claim 1, characterized in that, The Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 groups are independently selected from any one of the following groups; The R a R a The group is independently selected from hydrogen, deuterium, fluorine, cyano, nitro, and the following groups, whether substituted or unsubstituted: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl. Benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyrene, perylene, pyridyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thiophene, benzothiophene, dibenzothiophene, benzodibenzothiophene, pyrroleyl, indoleyl, carbazole any one of the following: alkyl, oxazolyl, benzoxazolyl, dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzoimidazolyl, dibenzoimidazolyl, quinolinyl, benzoquinolinyl, isoquinolinyl, benzoisoquinolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenantholinyl, naphridyl, acridineyl, phenoxazinyl, phenothiazinyl; or two adjacent R groups. a They can be linked together to form substituted or unsubstituted rings: benzene ring, naphthalene ring, pyridine ring, pyrimidine ring; The R x R y The group independently selected from hydrogen, deuterium, fluorine, cyano, nitro, or substituted or unsubstituted groups of the following: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl The following are all of the following: silyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyrene, perylene, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, and triazinyl; The R z The following groups, independently selected from hydrogen, deuterium, substituted or unsubstituted, are allowed: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl. The following are all of the following: vinyl dimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyrene, perylene, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, and triazinyl; a'1 is selected from 0, 1, or 2; a'2 is selected from 0, 1, 2, 3, or 4; a'3 is selected from 0, 1, 2, 3, 4, 5, or 6; a'4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; a'5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; when there are two or more R... a At that time, two or more R a 'They are the same as or different from each other.' 5. An aromatic amine compound according to claim 1, characterized in that, The L1, L2, L3, L4, L5, and L6 are independently selected from single bonds or any one of the following groups: The u is independently selected from either CH or N; Y1 and Y2 are independently selected from O, S, and N(R). s Any one of the following; Y3, Y4, and Y5 are independently selected from O, S, and C(R). p R q ), N(R s Any one of the following; The ring B is selected from substituted or unsubstituted C3~C10 alicyclic rings; The R b R b '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 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl; The R p R q 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, or R p R q The links between them form substituted or unsubstituted rings; The R z It is independently 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; The q is selected from 1, 2, 3, or 4; b1 is selected from 0, 1, 2, 3, or 4; b2 is selected from 0, 1, 2, 3, 4, 5, or 6; b3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; b4 is selected from 0, 1, or 2; when there are two or more R... b At that time, two or more R b The same or different between each other, or two adjacent R b They connect with each other to form substituted or unsubstituted rings; The b'1 is selected from 0, 1, or 2; when there are two or more R... b At that time, two or more R b 'They are the same as or different from each other.' 6. An aromatic amine compound according to claim 1, characterized in that, The L1, L2, L3, L4, L5, and L6 are independently selected from single bonds or any one of the following groups: The R b R b 'Independently selected from hydrogen, deuterium, fluorine, cyano, nitro, or substituted or unsubstituted groups of the following: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclocyclohep ...hepane, benzocyclohepane, benzocyclohepane, benzocyclohepane, benzocyclohepane, benzocyclohepane, benzocyclohepane, benzocyclohepane, benzocyclohepane, benzocyclohepane, benzocyclohepane, Butenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthraceneyl, phenanthrene, triphenylene, pyrene, perylene, pyridyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thiophene, benzothiophene, dibenzothiophene, benzodibenzothiophene, pyrroleyl Any one of the following: indolyl, carbazolyl, oxazolyl, benzoxazolyl, dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzoimidazolyl, dibenzoimidazolyl, quinolinyl, benzoquinolinyl, isoquinolinyl, benzoisoquinolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenantholinyl, naphridyl, acridineyl, phenoxazinyl, phenothiazinyl; The R p R q The group independently selected from hydrogen, deuterium, fluorine, cyano, nitro, or substituted or unsubstituted groups of the following: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl The following are all of the following: silyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyrene, perylene, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, and triazinyl; The R s The following groups, independently selected from hydrogen, deuterium, substituted or unsubstituted, are allowed: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl. The following are all of the following: vinyl dimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyrene, perylene, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, and triazinyl; b'1 is selected from 0, 1, or 2; b'2 is selected from 0, 1, 2, 3, or 4; b'3 is selected from 0, 1, 2, 3, 4, 5, or 6; b'4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; b'5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; when there are two or more R b At that time, two or more R b 'They are the same as or different from each other.' 7. An aromatic amine compound according to claim 1, characterized in that, Formula I is selected from any of the following structures: 。 8. An organic electroluminescent device, comprising an anode, a cathode, and an organic layer, wherein the organic layer is located between the anode and the cathode or on the side of the cathode facing away from the anode, 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. An organic electroluminescent device according to claim 8, wherein the organic layer is located between the anode and the cathode, characterized in that, The organic layer includes a hole transport layer, which includes at least one of the aromatic amine compounds according to any one of claims 1 to 7.

10. An organic electroluminescent device according to claim 8, wherein the organic layer is located on the side of the cathode opposite to the anode, characterized in that, The organic layer includes a capping layer, which contains at least one of the aromatic amine compounds according to any one of claims 1 to 7.

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