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. When the compound is used as a hole transport material, the compound has good hole mobility and can balance electron and hole transport, so that the luminous efficiency of a device is improved, and the service life of the device is prolonged; when being used as a luminescent layer material, the compound has a proper energy level and can promote electrons and holes to be compounded in a luminescent layer to form excitons, so that the luminous efficiency of a device is improved, and the service life of the device is prolonged; when the compound is used as a covering layer material, the compound has good thermal stability and refractive index, loss of light reflected by a nearby electrode during light emitting can be reduced, the stability of a film layer is effectively improved, and the performance of a device is improved. 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 materials are the core functional carriers of organic light-emitting diodes (OLEDs), and their performance directly determines the luminous efficiency, operational stability, and lifespan of the devices. OLEDs, with their self-emissive, fast-response, flexible, and customizable characteristics, have become a core technology in the display and lighting fields, and are widely used in smartphone displays, flexible display panels, and new lighting sources.

[0003] OLEDs are mainly composed of electrode material layers and organic functional material layers. When an appropriate voltage is applied, holes travel from the anode, through the hole injection layer and hole transport layer, and finally reach the emissive layer; while electrons travel from the cathode, through the electron injection layer and electron transport layer, to the emissive layer. These two types of charge carriers recombine in the emissive layer to form excitons, which transfer energy to the organic light-emitting molecules, causing them to transition from a low-energy ground state to a high-energy excited state. The molecules then return to the ground state via radiative transitions, releasing energy as light, thus enabling OLEDs to emit light.

[0004] In the functional layer system of organic light-emitting diodes (OLEDs), existing hole transport materials suffer from low hole mobility, leading to an imbalance in electron and hole transport. This makes it difficult for excitons to recombine efficiently in the light-emitting layer, thereby reducing the device's luminous efficiency and shortening its lifespan. Most host materials exhibit poor bipolar transport performance, with insufficient matching between the HOMO / LUMO energy levels and the hole transport layer, electron transport layer, and light-emitting dopants, easily triggering exciton quenching. Existing capping layer materials have a narrow refractive index tuning range and poor refractive index matching with the device substrate and encapsulation layer, limiting the improvement in light extraction efficiency. Furthermore, their glass transition temperatures are relatively low, making them prone to deformation during device fabrication and operation, compromising interface stability and long-term optical performance.

[0005] Therefore, in order to solve the above problems, it is of great significance to develop high-performance hole transport layer materials, light-emitting layer main materials and capping layer materials to solve problems such as carrier transport imbalance, low exciton utilization and insufficient light extraction efficiency. This is crucial for promoting the high performance and large-scale application of OLED devices. 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, wherein the aromatic amine compound is selected from the structure represented by formula I:

[0008]

[0009] Wherein, Ar1 is selected from formula II;

[0010]

[0011] Ring A and ring B are independently selected from any one of the substituted or unsubstituted structures in group 1, and ring A and ring B are not simultaneously selected from substituted or unsubstituted structures.

[0012] Group 1:

[0013] X is selected from either O or S;

[0014] The z is selected from C(R) t Any one of N;

[0015] The R t Independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, 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-C17 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;

[0016] Ar2 is selected from either Formula III or Formula IV;

[0017]

[0018] The v is independently selected from either C or N atoms, and when v is bonded to other groups, the v is selected from C atoms;

[0019] The Y is selected from either a single bond or N(R4);

[0020] R1, R2, and R3 are independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, 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;

[0021] The R4 is selected from any one of hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 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.

[0022] The value of e1 is selected from 0, 1, 2 or 3; the value of e2 is selected from 0, 1, 2, 3 or 4; when there are two or more R1s, the two or more R1s are the same as or different from each other;

[0023] The Ar3 is selected from hydrogen, deuterium, substituted or unsubstituted silyl groups, substituted or unsubstituted C1-C25 alkyl groups, substituted or unsubstituted C3-C25 cycloalkyl groups, formula III, formula IV, or any one of the following groups:

[0024]

[0025] X1 and X2 are independently selected from O, S, and N(R). z Any one of the following;

[0026] X3, X4, and X5 are independently selected from O, S, and C(R). p R q ), N(R z Any one of the following;

[0027] The t is independently selected from either C or N atoms, and when t is bonded to other groups, the t is selected from C atoms;

[0028] The t' is independently selected from either C or N atoms, and at most two of them are selected from N. When t' is bonded to other groups, the t' is selected from C atoms.

[0029] The ring C is selected from substituted or unsubstituted C3 to C10 alicyclic rings;

[0030] The R a R a '、R p R q Independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, 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 alkanes and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl, or R p R q The links between them form substituted or unsubstituted rings;

[0031] The R z It is selected from any one of hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 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;

[0032] a1 is selected from 0, 1, 2, 3, or 4; a2 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; a3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; a4 is selected from 0, 1, or 2; a5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; a6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; a7 is selected from 0, 1, 2, 3, 4, or 5; a8 is selected from 0, 1, 2, or 3; a9 is selected from 0, 1, 2, 3, 4, 5, or 6; 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;

[0033] 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 may be the same as or different from each other;

[0034] The L1 is selected from a single bond or any one of the following groups, or a combination of two or more of the following groups:

[0035]

[0036]

[0037] The u is independently selected from either C or N atoms, and at least one of them is selected from N. When u is bonded to other groups, the u is selected from C atoms.

[0038] The e is independently selected from either C or N atoms, and when e is bonded to other groups, the e is selected from C atoms;

[0039] Y1 and Y2 are independently selected from O, S, and N(R). s Any one of the following;

[0040] Y3, Y4, and Y5 are independently selected from O, S, and C(R). x R y ), N(R s Any one of the following;

[0041] The ring D is selected from substituted or unsubstituted C3-C10 alicyclic rings;

[0042] The R b R b '、R x R y Independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, 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 alkanes and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl, or R x R y The links between them form substituted or unsubstituted rings;

[0043] The R w It is independently selected from any one of deuterium, fluorine, trifluoromethyl, cyano, substituted or unsubstituted silyl, substituted or unsubstituted C1 to C25 alkyl, and substituted or unsubstituted C3 to C25 cycloalkyl;

[0044] The R sIt is selected from any one of hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 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;

[0045] The q is selected from 1, 2, 3, or 4;

[0046] The q' is selected from 1, 2, 3 or 4;

[0047] b1 is selected from 0, 1, 2, or 3; 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, 2, 3, or 4; b5 is selected from 0, 1, or 2; b6 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 The same or different between each other, or two adjacent R b They connect with each other to form substituted or unsubstituted rings;

[0048] 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 may be the same as or different from each other;

[0049] The w1 is selected from 1, 2, 3, or 4; when there are two or more R... w At that time, two or more R w They are the same as or different from each other;

[0050] The “” indicates the absence of a single bond. L2 and L3 are independently selected from any one of the following: a single bond, a substituted or unsubstituted C6-C30 arylene, a substituted or unsubstituted C2-C30 heteroarylene, a substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloalgide, or a substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloalgide. When “” indicates the absence of a single bond, L2 and L3 are connected to form a substituted or unsubstituted ring.

[0051] 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.

[0052] Beneficial effects

[0053] This invention provides an aromatic amine compound that, when used as a hole transport material, exhibits excellent hole mobility, balancing electron and hole transport and enabling efficient exciton recombination in the emissive layer, thereby improving device luminous efficiency and extending its lifespan. When used as an emissive layer material, the compound possesses suitable energy levels, promoting electron-hole recombination within the emissive layer to form excitons, thus improving device luminous efficiency and extending its lifespan. When used as a capping layer material, the compound exhibits excellent thermal stability and refractive index, reducing light loss due to reflection from nearby electrodes during emission, effectively improving film stability and device performance. The compound provided by this invention has a simple preparation method, readily available raw materials, and meets industrialization needs, demonstrating promising industrialization prospects. Detailed Implementation

[0054] The technical solutions of the embodiments of the present invention will be clearly and completely described below. 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.

[0055] In this specification, "-*" refers to the portion connected to another substituent. "-*" can be attached to any optional position of the group / fraction to which it is attached.

[0056] 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 Can represent And so on.

[0057] 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.

[0058] For example, Can represent Can represent Can represent And so on.

[0059] Examples of halogen atoms described in this invention may include fluorine, chlorine, bromine, and iodine.

[0060] The arylene group described in this invention can be a monocyclic arylene, a polycyclic arylene, or a fused-ring arylene. An arylene refers to a divalent group formed by removing two hydrogen atoms from the aromatic nucleus of an aromatic hydrocarbon molecule. It preferably has 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 include phenylene, biphenylene, terphenylene, naphthylene, anthracene, phenanthrene, trimethyleneene, pyrene, perylene, fluorene, phenylfluorene, dibenzo[a]fluorene, spirodifluorene, benzo[a]spirodifluorene, fluorenylene, etc., but are not limited thereto.

[0061] The heteroaryl group described in this invention refers to a group formed by replacing one or more aromatic carbon atoms in the aryl group with heteroatoms, including but not limited to O, S, N, Si, or P atoms. Preferably, it has 2 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 15 carbon atoms. Examples include, but are not limited to, pyridinyl, pyrimidinyl, triazineyl, furanyl, thiopheneyl, carbazolyl, benzofuranyl, benzothiopheneyl, benzocarbazolyl, dibenzofuranyl, dibenzothiopheneyl, dibenzocarbazolyl, benzodibenzofuranyl, benzodibenzothiopheneyl, isoquinolinyl, bipyridinyl, bipyrimidinyl, phenylpyridinyl, phenylpyrimidinyl, etc.

[0062] 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.

[0063] 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.

[0064] The aryl group described in this invention refers to a monovalent group formed by removing a hydrogen atom from the aromatic carbon atom of an aromatic compound molecule. It can be a monocyclic aryl group or a fused-ring aryl group, 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. Examples of aryl groups include, but are not limited to, phenyl, biphenyl, terphenyl, tetraphenyl, pentaphenyl, naphthyl, phenanthryl, anthraceneyl, fluorenyl, pyrene, triphenylene, fluoranthyl, benzo[a]fluorenyl, spirodifluorenyl, benzo[a]fluoranthyl, trefoilyl, etc.

[0065] 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. It can be a monocyclic heteroaryl or a fused-ring heteroaryl. The heteroatoms include, but are not limited to, oxygen, sulfur, nitrogen, silicon, and phosphorus atoms. Preferably, it has 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. These include, but are not limited to, pyridinyl, triazinyl, furanyl, thiopheneyl, pyrroleyl, imidazolyl, oxazolyl, thiazolyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzodibenzofuranyl, benzodibenzothiopheneyl, carbazolyl, benzocarbazolyl, acridineyl, phenoxazinyl, phenthiazinyl, phenoxthiazinyl, quinazolinyl, quinoxolinyl, quinolinyl, indolyl, azacarbazolyl, azafluorenyl, azaspirodifluorenyl, oxanthracenel, and thioxanthracenel.

[0066] The fused alicyclic and aromatic ring group described in this invention refers to a monovalent group formed by removing one hydrogen atom after the alicyclic and aromatic rings are fused together. Preferably, it has 7 to 30 carbon atoms, more preferably 7 to 18 carbon atoms, and most preferably 7 to 13 carbon atoms. Examples include benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, naphthocyclopropyl, naphthocyclobutyl, naphthocyclopentyl, naphthocyclohexyl, etc., but are not limited thereto.

[0067] The fused cyclic group of heterocyclic alkanes and aromatic rings described in this invention refers to the monovalent group formed by removing one hydrogen atom after a heterocyclic alkanes and aromatic rings are fused together. Preferably, it has 6 to 30 carbon atoms, more preferably 7 to 18 carbon atoms, and most preferably 7 to 13 carbon atoms. Examples include benzo[a]tetrahydropyrrole, naphtho[a]tetrahydropyrrole, phenanthrene[a]tetrahydropyrrole, benzo[a]hexacyclic butyl, benzo[a]hexacyclic heptyl, benzo[a]piperidinyl, naphtho[a]piperidinyl, phenanthrene[a]piperidinyl, etc., but are not limited thereto.

[0068] The fused cyclic group of alicyclic and heteroaromatic rings mentioned in this invention refers to a monovalent group formed by removing a hydrogen atom after the alicyclic and heteroaromatic rings are fused together. Preferably, it has 5 to 30 carbon atoms, more preferably 5 to 18 carbon atoms, and most preferably 5 to 12 carbon atoms. Examples include, but not limited to, dibenzofuranocyclopropyl, dibenzofuranocyclobutyl, dibenzofuranocyclopentyl, dibenzofuranocyclohexyl, dibenzofuranocycloheptyl, dibenzothiophenecyclopropyl, dibenzothiophenecyclobutyl, dibenzothiophenecyclopentyl, dibenzothiophenecyclohexyl, dibenzothiophenecycloheptyl, carbazocyclopropyl, carbazocyclobutyl, carbazocyclopentyl, carbazocyclohexyl, carbazocycloheptyl, pyridinocyclopropyl, pyridinocyclobutyl, pyridinocyclopentyl, pyridinocyclohexyl, pyridinobenzocycloheptyl, pyrimidinocyclopropyl, pyrimidinocyclobutyl, pyrimidinocyclopentyl, pyrimidinocyclohexyl, pyrimidinobenzocycloheptyl, etc.

[0069] The alkyl group described in this invention refers to a monovalent group formed by removing one hydrogen atom from an alkane molecule, preferably having 1 to 25 carbon atoms, more preferably having 1 to 12 carbon atoms, more preferably having 1 to 8 carbon atoms, and particularly preferably having 1 to 6 carbon atoms. This includes, but is not limited to, methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, isopropyl, isobutyl, sec-butyl, tert-butyl, etc.

[0070] 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.

[0071] 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, O, S, N, Si, or P atoms, 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, piperazineyl, tetrahydropyrrolyl, ethylene oxide, cyclothioethylene, propylenediyl, morpholinyl, thiomorpholinyl, etc., but are not limited thereto.

[0072] The "substituted or unsubstituted silyl group" mentioned in this invention refers to -Si(R k )3 groups, wherein each R k The same or different 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 alkanes and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl.

[0073] 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 aromatic 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.

[0074] 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:

[0075]

[0076] 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.

[0077] In this invention, "at least one" includes one, two, three, four, or more. "Two or more" may include two, three, four, or more, where permissible.

[0078] This invention provides an aromatic amine compound, wherein the aromatic amine compound is selected from the structure represented by formula I:

[0079]

[0080] Wherein, Ar1 is selected from formula II;

[0081]

[0082] Ring A and ring B are independently selected from any one of the substituted or unsubstituted structures in group 1, and ring A and ring B are not simultaneously selected from substituted or unsubstituted structures.

[0083] Group 1:

[0084] X is selected from either O or S;

[0085] The z is selected from C(R) t Any one of N;

[0086] The R t Independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, 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-C17 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;

[0087] Ar2 is selected from either Formula III or Formula IV;

[0088]

[0089] The v is independently selected from either C or N atoms, and when v is bonded to other groups, the v is selected from C atoms;

[0090] The Y is selected from either a single bond or N(R4);

[0091] R1, R2, and R3 are independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, 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;

[0092] The R4 is selected from any one of hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 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.

[0093] The value of e1 is selected from 0, 1, 2 or 3; the value of e2 is selected from 0, 1, 2, 3 or 4; when there are two or more R1s, the two or more R1s are the same as or different from each other;

[0094] The Ar3 is selected from hydrogen, deuterium, substituted or unsubstituted silyl groups, substituted or unsubstituted C1-C25 alkyl groups, substituted or unsubstituted C3-C25 cycloalkyl groups, formula III, formula IV, or any one of the following groups:

[0095]

[0096] X1 and X2 are independently selected from O, S, and N(R). z Any one of the following;

[0097] X3, X4, and X5 are independently selected from O, S, and C(R). p R q ), N(R z Any one of the following;

[0098] The t is independently selected from either C or N atoms, and when t is bonded to other groups, the t is selected from C atoms;

[0099] The t' is independently selected from either C or N atoms, and at most two of them are selected from N. When t' is bonded to other groups, the t' is selected from C atoms.

[0100] The ring C is selected from substituted or unsubstituted C3 to C10 alicyclic rings;

[0101] The R a R a '、R p R q Independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, 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 alkanes and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl, or R p R q The links between them form substituted or unsubstituted rings;

[0102] The R z It is selected from any one of hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 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;

[0103] a1 is selected from 0, 1, 2, 3, or 4; a2 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; a3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; a4 is selected from 0, 1, or 2; a5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; a6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; a7 is selected from 0, 1, 2, 3, 4, or 5; a8 is selected from 0, 1, 2, or 3; a9 is selected from 0, 1, 2, 3, 4, 5, or 6; 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;

[0104] The a'1 is selected from 0, 1, or 2; when there are two or more R a At that time, two or more Ra 'They may be the same as or different from each other;

[0105] The L1 is selected from a single bond or any one of the following groups, or a combination of two or more of the following groups:

[0106]

[0107] The u is independently selected from either C or N atoms, and at least one of them is selected from N. When u is bonded to other groups, the u is selected from C atoms.

[0108] The e is independently selected from either C or N atoms, and when e is bonded to other groups, the e is selected from C atoms;

[0109] Y1 and Y2 are independently selected from O, S, and N(R). s Any one of the following;

[0110] Y3, Y4, and Y5 are independently selected from O, S, and C(R). x R y ), N(R s Any one of the following;

[0111] The ring D is selected from substituted or unsubstituted C3-C10 alicyclic rings;

[0112] The R b R b '、R x R y Independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, 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 alkanes and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl, or R x R y The links between them form substituted or unsubstituted rings;

[0113] The R w It is independently selected from any one of deuterium, fluorine, trifluoromethyl, cyano, substituted or unsubstituted silyl, substituted or unsubstituted C1 to C25 alkyl, and substituted or unsubstituted C3 to C25 cycloalkyl;

[0114] The R sIt is selected from any one of hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 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;

[0115] The q is selected from 1, 2, 3, or 4;

[0116] The q' is selected from 1, 2, 3 or 4;

[0117] b1 is selected from 0, 1, 2, or 3; 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, 2, 3, or 4; b5 is selected from 0, 1, or 2; b6 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 The same or different between each other, or two adjacent R b They connect with each other to form substituted or unsubstituted rings;

[0118] 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 may be the same as or different from each other;

[0119] The w1 is selected from 1, 2, 3, or 4; when there are two or more R... w At that time, two or more R w They are the same as or different from each other;

[0120] The “-------” indicates the absence of a single bond or a single bond. L2 and L3 are independently selected from any one of the following: a single bond, a substituted or unsubstituted C6-C30 arylene, a substituted or unsubstituted C2-C30 heteroarylene, a substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloid, or a substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloid. When “-------” indicates the absence of a single bond, L2 and L3 are connected to form a substituted or unsubstituted ring.

[0121] Preferably, the aromatic amine compound is selected from the structure represented by formula I-1 or I-2:

[0122]

[0123] The definitions of Ar1, Ar2, Ar3, L1, L2, and L3 are the same as those in Equation I.

[0124] Preferably, the Ar1 is selected from any one of the following groups:

[0125]

[0126]

[0127]

[0128] X is independently selected from either O or S;

[0129] The R t The group is independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, and the following groups, whether substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, n-decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, trimethylsilane. Triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane Benzocyclohexyl, naphthocyclohexyl, benzocycloheptyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyrene, perylene, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thiophene, benzothiophene, dibenzothiophene, benzene The following are all of the following: dibenzothiophene, pyrrole, indolyl, carbazolyl, oxazolyl, benzoxazolyl, dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzoimidazolyl, dibenzoimidazolyl, quinolinyl, benzoquinolinyl, isoquinolinyl, benzoisoquinolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenantholinyl, naphridyl, acridineyl, phenoxazinyl, and phenothiazinyl.

[0130] t1 is selected from 0, 1, 2, 3, 4, 5, or 6; t2 is selected from 0, 1, 2, or 3; t3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; t4 is selected from 0, 1, 2, 3, or 4; t5 is selected from 0, 1, 2, 3, 4, or 5; t6 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; when there are two or more R... t At that time, two or more R t They may be the same as or different from each other.

[0131] Preferably, at most 3, 2, or 1 z in each group are selected from N.

[0132] Preferably, in each six-membered ring containing z, at most two or at most one z are selected from N.

[0133] More preferably, the Ar1 is selected from any one of the following groups:

[0134]

[0135]

[0136]

[0137]

[0138]

[0139] Preferably, the Ar2 (or formula III or formula IV) is selected from any one of the following groups:

[0140] The Y' is selected from N(R4);

[0141] R1, R2, and R3 are independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, and substituted or unsubstituted groups of the following: methyl, ethyl, propyl, butyl, pentyl, hexyl, 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, benzocycloheptanyl ... Cyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthraceneyl, phenanthrene, triphenylene, pyrene, perylene, pyridyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thiopheneyl, benzothiopheneyl, dibenzothiopheneyl, benzodibenzothiopheneyl, 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;

[0142] The R4 is independently selected from hydrogen, deuterium, and substituted or unsubstituted groups of the following: methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, etc. The following is a list of compounds: methylsilyl, 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.

[0143] The e1 is selected from 0, 1, 2 or 3; the e2 is selected from 0, 1, 2, 3 or 4; the e3 is selected from 0, 1 or 2; the e4 is selected from 0 or 1; when there are two or more R1s, the two or more R1s are the same as or different from each other.

[0144] More preferably, the Ar2 (or formula III or formula IV) is selected from any one of the following groups:

[0145]

[0146]

[0147] The Y' is selected from N(R4);

[0148] R2 and R3 are independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, and ethylene. The following are all of the following: dimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyrene, peryl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, and triazinyl;

[0149] The R4 is independently selected from deuterium, methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl. Any one of the following: tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthraceneyl, phenanthrene, triphenylene, pyrene, peryl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, and triazinyl.

[0150] Preferably, the Ar3 is selected from hydrogen, deuterium, substituted or unsubstituted silyl groups, substituted or unsubstituted C1-C25 alkyl groups, substituted or unsubstituted C3-C25 cycloalkyl groups, formula III, formula IV, or any one of the following groups:

[0151]

[0152]

[0153] The R a R a '、R p R q The group is independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, and substituted or unsubstituted groups of the following: methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, 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, pyrrole, indole The following are all of the following: carbazolyl, oxazolyl, benzoxazolyl, dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzoimidazolyl, dibenzoimidazolyl, quinolinyl, benzoquinolinyl, isoquinolinyl, benzoisoquinolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenantholinyl, naphridyl, acridineyl, phenoxazinyl, phenothiazinyl;

[0154] The R zSelected from hydrogen, deuterium, and the following substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl Any one of silyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthraceneyl, phenanthrene, triphenylene, pyrene, perylene, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, and triazinyl;

[0155] a1 is selected from 0, 1, 2, 3, or 4; a2 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; a3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; a4 is selected from 0, 1, or 2; a5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; a6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; a7 is selected from 0, 1, 2, 3, 4, or 5; a8 is selected from 0, 1, 2, or 3; a9 is selected from 0, 1, 2, 3, 4, 5, or 6; 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;

[0156] 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; a'6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14; 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.'

[0157] More preferably, the Ar3 is selected from hydrogen, deuterium, methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, formula III, formula IV, or any one of the following groups:

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164] Preferably, when L2 and L3 are not connected, Ar3 is selected from the aromatic groups mentioned above.

[0165] Preferably, L1 is selected from a single bond or any one of the following groups, or a combination of two or more of the following groups:

[0166]

[0167] The R b R b '、R x R yThe group is independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, and substituted or unsubstituted groups of the following: methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, 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, pyrrole, indole The following are all of the following: carbazolyl, oxazolyl, benzoxazolyl, dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzoimidazolyl, dibenzoimidazolyl, quinolinyl, benzoquinolinyl, isoquinolinyl, benzoisoquinolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenantholinyl, naphridyl, acridineyl, phenoxazinyl, phenothiazinyl;

[0168] The R w The group is independently selected from deuterium, fluorine, trifluoromethyl, cyano, or any of the following substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, and vinyldimethylsilyl.

[0169] The R sSelected from hydrogen, deuterium, and the following substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl Any one of silyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthraceneyl, phenanthrene, triphenylene, pyrene, perylene, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, and triazinyl;

[0170] b1 is selected from 0, 1, 2, or 3; 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, 2, 3, or 4; b5 is selected from 0, 1, or 2; b6 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 The same or different between each other, or two adjacent R b They connect with each other to form substituted or unsubstituted rings;

[0171] 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.'

[0172] More preferably, L1 is selected from a single bond or any one of the following groups, or a combination of two or more of the following groups:

[0173]

[0174]

[0175]

[0176] Preferably, L2 and L3 are independently selected from single bonds or any one of the following groups, or a combination of two or more of the following groups:

[0177]

[0178] The r is independently selected from either C or N atoms, and when r is bonded to other groups, the r is selected from C atoms;

[0179] Y6 and Y7 are independently selected from O, S, and N(R) k Any one of the following;

[0180] The Y8, Y9, Y 10 Independently selected from O, S, C(R) i R j ), N(R k Any one of the following;

[0181] The ring E is selected from substituted or unsubstituted C3-C10 alicyclic rings;

[0182] The R c R c '、R i R j Independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, 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 alkanes and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl, or R i R j The links between them form substituted or unsubstituted rings;

[0183] The R k It is selected from any one of hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 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;

[0184] The number n is selected from 1, 2, 3, or 4;

[0185] c1 is selected from 0, 1, 2, 3, or 4; c2 is selected from 0, 1, 2, 3, 4, 5, or 6; c3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; c4 is selected from 0, 1, or 2; when there are two or more R... c At that time, two or more R c The same or different between each other, or two adjacent R c They connect with each other to form substituted or unsubstituted rings;

[0186] The c'1 is selected from 0, 1, or 2; when there are two or more R... c At that time, two or more R c 'They are the same as or different from each other.'

[0187] More preferably, L2 and L3 are independently selected from single bonds or any one of the following groups, or a combination of two or more of the following groups:

[0188]

[0189]

[0190] Most preferably, formula I is selected from any of the following structures:

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216] 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.

[0217] 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.

[0218] 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.

[0219] 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.

[0220] 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.

[0221] More preferably, the light-emitting layer comprises a host material, which comprises at least one of the aromatic amine compounds described in this invention.

[0222] 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.

[0223] The hole injection layer of this invention is preferably made of a material with high hole injection capability. In addition to the aromatic amine compounds provided by this invention, it may also include triaromatic amine compounds, metal compounds, quinone derivatives, phthalocyanine derivatives, polymers, axial alkene compounds, and other substances with high hole injection capability. Specific examples include, but are not limited to, tetracyanoquinone dimethyl ether (TCNQ), 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanoquinone-dimethyl ether (F4-TCNQ), 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), and 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]biphenyl] The following compounds are preferred: 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), 1,4,5,8,9,11-hexaazabenzonitrile (HAT-CN), poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS), etc. Aromatic amine compounds of the present invention are preferred.

[0224] The hole transport layer described in this invention is preferably made of a material with high hole transport properties. In addition to the aromatic amine compounds provided in this invention, it may also include aromatic amine derivatives, biphenyl diamine derivatives, carbazole derivatives, fluorene derivatives, stilbene derivatives, phthalocyanine compounds, anthraquinone compounds, quinacridone compounds, hexanitrile hexaazabenzophenanthrene compounds, polythiophene, polyaniline, polyvinylcarbazole, etc. Specific examples of the hole transport materials 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. Aromatic amine compounds of the present invention are preferred.

[0225] The luminescent layer of this invention may include a single material, a host material (also called a matrix material), and a dopant material (also called a guest material). The luminescent layer material may include multiple host materials and multiple dopant materials. The type of dopant material can be fluorescent, phosphorescent, or TADF. Fluorescent dopant materials may include: fused polycyclic aromatic derivatives, styrene-based amine derivatives, fused-ring amine derivatives, boron-containing compounds, pyrrole derivatives, indole derivatives, carbazole derivatives, etc., such as C545T, BCzVBi, DPAVBi, etc. Phosphorescent dopant materials may include: heavy metal complexes, phosphorescent rare-earth metal complexes, etc., such as FIrpic, Ir(ppy)3, Ir(ppy)2(acac), etc. In addition to the aromatic amine compounds provided by this invention, the host material of the luminescent layer may also include fused aromatic ring derivatives, heterocyclic compounds, etc. Fused aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentane derivatives, phenanthrene derivatives, fluoranthene derivatives, etc., and heterocyclic compounds including carbazole derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, pyrimidine derivatives, etc., such as Alq3, BAlq, TPBi, TPD, CBP, TCTA, ADN, etc., but not limited thereto. The aromatic amine compounds of the present invention are preferred.

[0226] 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 fluoride (LiF), lithium oxide (Li₂O), cesium fluoride (CsF), magnesium phosphide (MgP), cesium carbonate (Cs₂CO₃), lithium oxide (Li₂O), lithium boron oxide (LiBO₂), aluminum oxide (Al₂O₃), and vanadium oxide (V₂O₅).

[0227] The electron transport layer described in this invention is preferably made of a material with high electron transport properties. Electron transport layer materials may include metal complexes, pyridine derivatives, imidazole derivatives, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, etc. The electron transport materials include, but are not limited to, 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), bis(10-hydroxybenzo[h]quinoline)beryllium (BeBq2), and bis(2-methyl-8-hydroxyquinoline)(4-phenylphenol)aluminum(III) (BAlq), etc.

[0228] The electron blocking layer of this invention is preferably made of a material with good hole transport capability and electron blocking capability. In addition to the aromatic amine compounds provided by this invention, it may also include aromatic amine derivatives, carbazole derivatives, etc. Specific examples may include N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB), etc., but are not limited thereto. The aromatic amine compounds of this invention are preferred.

[0229] The hole-blocking layer described in this invention can typically be formed under the same conditions as the hole injection layer. It may include aluminum complexes, lithium complexes, beryllium complexes, oxazole derivatives, benzoxazole derivatives, thiazole derivatives, benzothiazole derivatives, imidazole derivatives, benzimidazole derivatives, phenanthrene derivatives, polymers, rare earth derivatives, triazine derivatives, quinoline derivatives, diazanphenanthrene derivatives, azirbenzene derivatives, anthrone derivatives, etc. Specific examples of the hole-blocking layer material include, but are not limited to, BCP, BAlq, TPBi, etc.

[0230] The capping material described in this invention is preferably a material with photocoupling properties. In addition to the aromatic amine compounds provided in this invention, the capping material also includes imidazole derivatives, oxazole derivatives, thiazole derivatives, and aromatic amine derivatives. 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, and magnesium fluoride. The aromatic amine compounds of this invention are preferred.

[0231] 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, aluminum (Al), silver (Ag), gold (Au), lead (Pb), lithium (Li), magnesium (Mg), ytterbium (Yb), calcium (Ca), magnesium-silver alloy (Mg:Al), lithium-aluminum alloy (Li:Al), and calcium / silver (Ca / Ag).

[0232] The anode material described in this invention is preferably a high work function material, including metals, alloys, conductive compounds, and mixtures thereof. It may include zinc (Zn), gold (Au), platinum (Pt), chromium (Cr), copper (Cu), palladium (Pd), titanium (Ti), and palladium (Pd), or alloys thereof; metal oxides may include zinc oxide (ZnO), indium oxide (InO), tin oxide (SnO2), indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides may include zinc oxide / aluminum (ZnO / Al), silver / indium tin oxide (Ag / ITO), and indium tin oxide / silver / indium tin oxide (ITO / Ag / ITO); conductive polymers may include poly[3,4-(ethylene-1,2-dioxothiophene)] (PEDOT), polypyrrole (PPY), and polyaniline (PANI), but are not limited thereto.

[0233] 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.

[0234] [Synthesis Route]

[0235] Preparation of Formula I compound when L2 and L3 are not cyclic:

[0236]

[0237] Preparation of compound I when L2 and L3 form a ring:

[0238]

[0239] Xa, Xb, Xc, Xd, and Xe are each independently selected from any one of Cl, Br, and I; the limitations of Ar1, Ar2, Ar3, L1, L2, and L3 are the same as those described above.

[0240] Description of raw materials, reagents, and characterization equipment:

[0241] 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.

[0242] Mass spectrometry was performed using a Waters G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer, with chloroform as the solvent.

[0243] Elemental analysis was performed using a VarioELcube organic elemental analyzer from Elementar GmbH, Germany, with sample masses ranging from 5 to 10 mg.

[0244] Synthesis Example 1: Preparation of Compound 10

[0245]

[0246] Preparation of intermediate A-10:

[0247] Under nitrogen protection, toluene (420 mL), a-10 (11.85 g, 70.00 mmol), b-10 (22.41 g, 70.00 mmol), sodium tert-butoxide (13.45 g, 140.00 mmol), palladium acetate (0.24 g, 1.05 mmol), and tri-tert-butylphosphine (0.85 g, 4.20 mmol) were added to a reaction flask and refluxed for 3.5 hours. After the reaction was complete, the reaction solution was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic phase was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. The solution was recrystallized from toluene:ethanol (5:1) to give A-10 (23.73 g, yield 83%). The purity of the solid was ≥99.86% as determined by HPLC. Mass spectrometry m / z: 408.1638 (theoretical value: 408.1626).

[0248] Preparation of compound 10:

[0249] Under nitrogen protection, toluene (240 mL), A-10 (12.26 g, 30.00 mmol), c-10 (10.42 g, 30.00 mmol), sodium tert-butoxide (5.77 g, 60.00 mmol), tris(dibenzylacetone)palladium (0.27 g, 0.3 mmol), and X-phos (0.29 mL, 0.60 mmol) were added to a reaction flask and refluxed for 5 hours. After the reaction was complete, the reaction solution was cooled to room temperature, water was added, and the mixture was extracted with chloroform. The organic phase was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. The mixture was recrystallized from toluene to give compound 10 (14.98 g, yield 74%). The purity of the solid was ≥99.98% as determined by HPLC. Mass spectrometry m / z: 674.2368 (theoretical value: 674.2358). Theoretical elemental content (%) C 50 H 30 N2O: C, 89.00; H, 4.48; N, 4.15. Measured elemental content (%): C, 89.01; H, 4.49; N, 4.11.

[0250] Synthesis Example 2: Preparation of Compound 23

[0251]

[0252] According to the preparation method in Example 1, a-10 was replaced with an equimolar amount of a-23, b-10 was replaced with an equimolar amount of b-23, and c-10 was replaced with an equimolar amount of c-23, yielding compound 23 (15.18 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 674.2372 (theoretical value: 674.2358). Theoretical elemental content (%) C 50 H 30 N₂O: C, 89.00; H, 4.48; N, 4.15. Measured elemental content (%): C, 89.03; H, 4.47; N, 4.18.

[0253] Synthesis Example 3: Preparation of Compound 48

[0254]

[0255] According to the preparation method in Synthesis Example 1, a-10 was replaced with an equimolar amount of a-48, b-10 was replaced with an equimolar amount of b-23, and c-10 was replaced with an equimolar amount of c-48, yielding compound 48 (15.87 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 724.2502 (theoretical value: 724.2515). Theoretical elemental content (%) C 54 H 32N₂O: C, 89.48; H, 4.45; N, 3.86. Measured elemental content (%): C, 89.45; H, 4.47; N, 3.81.

[0256] Synthesis Example 4: Preparation of Compound 57

[0257]

[0258] According to the preparation method in Example 1, a-10 was replaced with an equimolar amount of a-57, b-10 was replaced with an equimolar amount of b-57, and c-10 was replaced with an equimolar amount of c-23, yielding compound 57 (14.79 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 648.2217 (theoretical value: 648.2202). Theoretical elemental content (%) C 48 H 28 N₂O: C, 88.87; H, 4.35; N, 4.32. Measured elemental content (%): C, 88.82; H, 4.37; N, 4.31.

[0259] Synthesis Example 5: Preparation of Compound 66

[0260]

[0261] According to the preparation method in Synthesis Example 1, a-10 was replaced with an equimolar amount of a-66, b-10 was replaced with an equimolar amount of b-23, and c-1 was replaced with an equimolar amount of c-66, yielding compound 66 (16.18 g). HPLC analysis showed a solid purity ≥ 99.99%. Mass spectrometry m / z: 748.2504 (theoretical value: 748.2515). Theoretical elemental content (%) C 56 H 32 N₂O: C, 89.82; H, 4.31; N, 3.74. Measured elemental content (%): C, 89.80; H, 4.32; N, 3.78.

[0262] Synthesis Example 6: Preparation of Compound 77

[0263]

[0264] According to the preparation method in Synthesis Example 1, a-10 was replaced with an equimolar amount of a-77, b-10 was replaced with an equimolar amount of b-23, and c-10 was replaced with an equimolar amount of c-23, yielding compound 77 (14.96 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 664.2529 (theoretical value: 664.2515). Theoretical elemental content (%) C 49 H 32N₂O: C, 88.53; H, 4.85; N, 4.21. Measured elemental content (%): C, 88.57; H, 4.84; N, 4.24.

[0265] Synthesis Example 7: Preparation of Compound 95

[0266]

[0267] According to the preparation method in Synthesis Example 1, a-10 was replaced with an equimolar amount of a-95, b-10 was replaced with an equimolar amount of b-23, and c-10 was replaced with an equimolar amount of c-95, yielding compound 95 (14.78 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 665.2114 (theoretical value: 665.2103). Theoretical elemental content (%) C 47 H 27 N3O2: C, 84.79; H, 4.09; N, 6.31. Measured elemental content (%): C, 84.77; H, 4.12; N, 6.30.

[0268] Synthesis Example 8: Preparation of Compound 145

[0269]

[0270] According to the preparation method in Example 1, a-10 was replaced with an equimolar amount of a-145, b-10 was replaced with an equimolar amount of b-23, and c-10 was replaced with an equimolar amount of c-23, yielding compound 145 (15.08 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 688.2165 (theoretical value: 688.2151). Theoretical elemental content (%) C 50 H 28 N2O2: C, 87.19; H, 4.10; N, 4.07. Measured elemental content (%): C, 87.15; H, 4.12; N, 4.05.

[0271] Synthesis Example 9: Preparation of Compound 180

[0272]

[0273] According to the preparation method in Synthesis Example 1, a-10 was replaced with an equimolar amount of a-180, b-10 was replaced with an equimolar amount of b-180, and c-10 was replaced with an equimolar amount of c-23, yielding compound 180 (16.14 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 757.2175 (theoretical value: 757.2188). Theoretical elemental content (%) C 53 H 31N3OS: C, 83.99; H, 4.12; N, 5.54. Measured elemental content (%): C, 83.96; H, 4.15; N, 5.55.

[0274] Synthesis Example 10: Preparation of Compound 187

[0275]

[0276] According to the preparation method in Example 1, a-10 was replaced with an equimolar amount of a-187, b-10 was replaced with an equimolar amount of b-180, and c-10 was replaced with an equimolar amount of c-187, yielding compound 187 (17.67 g). HPLC analysis showed a solid purity ≥ 99.99%. Mass spectrometry m / z: 878.2946 (theoretical value: 878.2933). Theoretical elemental content (%) C 65 H 38 N2O2: C, 88.82; H, 4.36; N, 3.19. Measured elemental content (%): C, 88.79; H, 4.37; N, 3.24.

[0277] Synthesis Example 11: Preparation of Compound 230

[0278]

[0279] According to the preparation method in Synthesis Example 1, a-10 was replaced with an equimolar amount of a-230, b-10 was replaced with an equimolar amount of b-23, and c-10 was replaced with an equimolar amount of c-23, yielding compound 230 (17.02 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 798.3602 (theoretical value: 798.3610). Theoretical elemental content (%) C 59 H 46 N₂O: C, 88.69; H, 5.80; N, 3.51. Measured elemental content (%): C, 88.68; H, 5.83; N, 3.54.

[0280] Synthesis Example 12: Preparation of Compound 234

[0281]

[0282] According to the preparation method in Synthesis Example 1, a-10 was replaced with an equimolar amount of a-234, b-10 was replaced with an equimolar amount of b-23, and c-10 was replaced with an equimolar amount of c-234, yielding compound 234 (14.78 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 656.1911 (theoretical value: 656.1900). Theoretical elemental content (%) C 46 H25 FN2O2: C, 84.13; H, 3.84; N, 4.27. Measured elemental content (%): C, 84.11; H, 3.88; N, 4.26.

[0283] Synthetic Example 13: Preparation of Compound 255

[0284]

[0285] According to the preparation method in Example 1, a-10 was replaced with an equimolar amount of a-255, b-10 was replaced with an equimolar amount of b-23, and c-10 was replaced with an equimolar amount of c-23, yielding compound 255 (15.20 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 684.2185 (theoretical value: 684.2173). Theoretical elemental content (%) C 48 H 24 D4N2OS: C, 84.18; H, 4.71; N, 4.09. Measured elemental content (%): C, 84.24; H, 4.69; N, 4.10.

[0286] Synthesis Example 14: Preparation of Compound 263

[0287]

[0288] According to the preparation method in Synthesis Example 1, a-10 was replaced with an equimolar amount of a-23, b-10 was replaced with an equimolar amount of b-23, and c-10 was replaced with an equimolar amount of c-263, yielding compound 263 (16.31 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 754.2913 (theoretical value: 754.2922). Theoretical elemental content (%) C 56 H 30 D4N2O: C, 89.10; H, 5.07; N, 3.71. Measured elemental content (%): C, 89.11; H, 5.04; N, 3.72.

[0289] Synthesis Example 15: Preparation of Compound 267

[0290]

[0291] According to the preparation method in Synthesis Example 1, a-10 was replaced with an equimolar amount of a-267, b-10 was replaced with an equimolar amount of b-267, and c-10 was replaced with an equimolar amount of c-95, yielding compound 267 (16.63 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 791.2948 (theoretical value: 791.2937). Theoretical elemental content (%) C58 H 37 N3O: C, 87.96; H, 4.71; N, 5.31. Measured elemental content (%): C, 87.95; H, 4.73; N, 5.36.

[0292] Synthesis Example 16: Preparation of Compound 288

[0293]

[0294] According to the preparation method in Synthesis Example 1, a-10 was replaced with an equimolar amount of a-288, b-10 was replaced with an equimolar amount of b-23, and c-10 was replaced with an equimolar amount of c-288, yielding compound 288 (15.66 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 714.2145 (theoretical value: 714.2130). Theoretical elemental content (%) C 52 H 30 N2S: C, 87.37; H, 4.23; N, 3.92. Measured elemental content (%): C, 87.36; H, 4.26; N, 3.90.

[0295] Synthesis Example 17: Preparation of Compound 296

[0296]

[0297] According to the preparation method in Example 1, a-10 was replaced with an equimolar amount of a-296, b-10 was replaced with an equimolar amount of b-23, and c-10 was replaced with an equimolar amount of c-296, yielding compound 296 (15.31 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 689.1912 (theoretical value: 689.1926). Theoretical elemental content (%) C 49 H 27 N3S: C, 85.32; H, 3.95; N, 6.09. Measured elemental content (%): C, 85.34; H, 3.96; N, 6.08.

[0298] Synthesis Example 18: Preparation of Compound 304

[0299]

[0300] According to the preparation method in Synthesis Example 1, a-10 was replaced with an equimolar amount of a-304, b-10 was replaced with an equimolar amount of b-23, and c-10 was replaced with an equimolar amount of c-304, yielding compound 304 (15.15 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 691.2071 (theoretical value: 691.2082). Theoretical elemental content (%) C49 H 29 N3S: C, 85.07; H, 4.23; N, 6.07. Measured elemental content (%): C, 85.09; H, 4.22; N, 6.10.

[0301] Synthetic Example 19: Preparation of Compound 314

[0302]

[0303] According to the preparation method in Example 1, a-10 was replaced with an equimolar amount of a-314, b-10 was replaced with an equimolar amount of b-314, and c-10 was replaced with an equimolar amount of c-314, yielding compound 314 (15.30 g). HPLC analysis showed a solid purity ≥ 99.99%. Mass spectrometry m / z: 679.2096 (theoretical value: 679.2082). Theoretical elemental content (%) C 48 H 29 N3S: C, 84.80; H, 4.30; N, 6.18. Measured elemental content (%): C, 84.82; H, 4.27; N, 6.19.

[0304] Synthesis Example 20: Preparation of Compound 336

[0305]

[0306] According to the preparation method in Example 1, a-10 was replaced with an equimolar amount of a-336, b-10 was replaced with an equimolar amount of b-23, and c-10 was replaced with an equimolar amount of c-336, yielding compound 336 (16.25 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 762.2537 (theoretical value: 762.2525). Theoretical elemental content (%) C 53 H 38 N₂SSi: C, 83.43; H, 5.02; N, 3.67. Measured elemental content (%): C, 83.42; H, 5.05; N, 3.66.

[0307] Synthesis Example 21: Preparation of Compound 338

[0308]

[0309] According to the preparation method in Example 1, a-10 was replaced with an equimolar amount of a-338, b-10 was replaced with an equimolar amount of b-23, and c-10 was replaced with an equimolar amount of b-23, yielding compound 338 (15.94 g). HPLC analysis showed a solid purity ≥ 99.99%. Mass spectrometry m / z: 727.2097 (theoretical value: 727.2082). Theoretical elemental content (%) C 52 H 29 N3S: C, 85.81; H, 4.02; N, 5.77. Measured elemental content (%): C, 85.84; H, 4.05; N, 5.78.

[0310] Synthesis Example 22: Preparation of Compound 386

[0311]

[0312] According to the preparation method in Synthesis Example 1, a-10 was replaced with an equimolar amount of a-386, b-10 was replaced with an equimolar amount of b-386, and c-10 was replaced with an equimolar amount of c-386, yielding compound 386 (16.13 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 746.2131 (theoretical value: 746.2140). Theoretical elemental content (%) C 51 H 30 N4OS: C, 82.02; H, 4.05; N, 7.50. Measured elemental content (%): C, 82.04; H, 4.04; N, 7.56.

[0313] Synthesis Example 23: Preparation of Compound 390

[0314]

[0315] According to the preparation method in Synthesis Example 1, a-10 was replaced with an equimolar amount of a-390, b-10 was replaced with an equimolar amount of b-390, and c-10 was replaced with an equimolar amount of c-314, yielding compound 390 (14.72 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 700.2767 (theoretical value: 700.2757). Theoretical elemental content (%) C 50 H 20 D 10 N2S: C, 85.68; H, 5.75; N, 4.00. Measured elemental content (%): C, 85.65; H, 5.76; N, 4.02.

[0316] Synthesis Example 24: Preparation of Compound 398

[0317]

[0318] According to the preparation method in Example 1, a-10 was replaced with an equimolar amount of a-398, b-10 was replaced with an equimolar amount of b-23, and c-10 was replaced with an equimolar amount of c-314, yielding compound 398 (16.57 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 766.2431 (theoretical value: 766.2443). Theoretical elemental content (%) C 56 H 34 N2S: C, 87.70; H, 4.47; N, 3.65. Measured elemental content (%): C, 87.73; H, 4.45; N, 3.61.

[0319] Synthesis Example 25: Preparation of Compound 405

[0320]

[0321] According to the preparation method in Synthesis Example 1, a-10 was replaced with an equimolar amount of a-405, b-10 was replaced with an equimolar amount of b-23, and c-10 was replaced with an equimolar amount of c-405, yielding compound 405 (17.21 g). HPLC analysis showed a solid purity ≥ 99.99%. Mass spectrometry m / z: 855.2722 (theoretical value: 855.2708). Theoretical elemental content (%) C 62 H 37 N3S: C, 86.99; H, 4.36; N, 4.91. Measured elemental content (%): C, 86.97; H, 4.35; N, 4.93.

[0322] Synthesis Example 26: Preparation of Compound 408

[0323]

[0324] Preparation of intermediate B-408:

[0325] Under nitrogen protection, d-408 (12.83 g, 45.00 mmol), e-408 (11.07 g, 45.00 mmol), and K₂CO₃ (12.44 g, 90.00 mmol) were dissolved in 225 mL of toluene / ethanol / water (2:1:1). Pd(dppf)Cl₂ (0.66 g, 0.90 mmol) was added with stirring, and the mixture was heated under reflux for 5 h. After the reaction was complete, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from the resulting solid using toluene / ethanol at an 8:1 ratio to give intermediate B-408 (15.55 g, 85% yield); HPLC purity ≥ 99.82%. Mass spectrometry m / z: 406.1485 (theoretical value: 406.1470).

[0326] Preparation of compound 408:

[0327] Under nitrogen protection, B-408 (12.19 g, 30.00 mmol), C-23 (8.91 g, 30.00 mmol), and sodium tert-butoxide (4.32 g, 45.00 mmol) dissolved in 135 mL of toluene were added to a reaction flask with stirring. Pd₂(dba)₃ (0.27 g, 0.30 mmol) and X-Phos (0.29 g, 0.60 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 408 (14.20 g, 76% yield). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 622.2057 (theoretical value: 622.2045). Theoretical elemental content (%) C 46 H 26 N₂O, C, 88.72; H, 4.21; N, 4.50. Measured elemental content (%): C, 88.70; H, 4.25; N, 4.51.

[0328] Synthesis Example 27: Preparation of Compound 454

[0329]

[0330] Preparation of intermediate B-454:

[0331] Under nitrogen protection, d-408 (17.11 g, 60.00 mmol), e-454 (16.83 g, 60.00 mmol), and K2CO3 (16.59 g, 120.00 mmol) were dissolved in 300 mL of toluene / ethanol / water (2:1:1). Pd(dppf)Cl2 (0.88 g, 1.20 mmol) was added with stirring, and the mixture was heated under reflux for 4.5 h. After the reaction was complete, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from the resulting solid using toluene / ethanol at an 8:1 ratio to give intermediate B-454 (21.69 g, yield 82%); HPLC purity ≥ 99.72%. Mass spectrometry m / z: 440.1071 (theoretical value: 440.1080).

[0332] Preparation of intermediate C-454:

[0333] Under argon protection, B-454 (19.84 g, 45.00 mmol), f-454 (5.53 g, 45.00 mmol), K2CO3 (9.33 g, 67.50 mmol), and 375 mL of toluene / ethanol / water (2:1:1) mixed solvent were added to the reaction flask. After purging the air with argon three times, Pd(PPh3)4 (0.52 g, 0.45 mmol) was added. The mixture was stirred and the system was heated under reflux for 5.5 hours. After the reaction was completed, the mixture was cooled to room temperature, distilled water was added, and the toluene layer was separated and dried with anhydrous magnesium sulfate. The solvent was concentrated by rotary evaporation after filtration, and crystals were precipitated by cooling and filtration. The crystals were then recrystallized from toluene / methanol at a ratio of 10:1 to obtain intermediate C-454 (16.97 g, yield 78%) with an HPLC purity of ≥99.88%. Mass spectrometry m / z: 483.1753 (theoretical value: 483.1735).

[0334] Preparation of compound 454:

[0335] Under nitrogen protection, C-454 (14.51 g, 30.00 mmol), C-95 (8.91 g, 30.00 mmol), and sodium tert-butoxide (4.32 g, 45.00 mmol) dissolved in 135 mL of toluene were added to a reaction flask with stirring. Pd₂(dba)₃ (0.27 g, 0.30 mmol) and X-Phos (0.29 g, 0.60 mmol) were added, and the mixture 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 454 (15.54 g, 74% yield). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 699.2303 (theoretical value: 699.2311). Theoretical elemental content (%) C 51 H 29 N3O: C, 87.53; H, 4.18; N, 6.00. Measured elemental content (%): C, 87.55; H, 4.17; N, 6.01.

[0336] Synthesis Example 28: Preparation of Compound 465

[0337]

[0338] According to the preparation method in Synthesis Example 27, d-408 was replaced with an equimolar amount of d-465, e-454 with an equimolar amount of e-465, f-454 with an equimolar amount of f-465, and c-95 with an equimolar amount of g-465, yielding compound 465 (16.20 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 739.2279 (theoretical value: 739.2260). Theoretical elemental content (%) C 53 H 29 N3O2: C, 86.04; H, 3.95; N, 5.68. Measured elemental content (%): C, 86.07; H, 3.94; N, 5.70.

[0339] Synthesis Example 29: Preparation of Compound 499

[0340]

[0341] According to the preparation method in Synthesis Example 26, d-408 was replaced with an equimolar amount of d-499, and c-23 was replaced with an equimolar amount of g-499, yielding compound 499 (16.29 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 775.2632 (theoretical value: 775.2624). Theoretical elemental content (%) C 57 H 33N3O: C, 88.24; H, 4.29; N, 5.42. Measured elemental content (%): C, 88.27; H, 4.31; N, 5.40.

[0342] Synthesis Example 30: Preparation of Compound 516

[0343]

[0344] According to the preparation method of Synthesis Example 27, f-454 was replaced with an equimolar amount of f-516, and c-95 was replaced with an equimolar amount of g-516 to obtain compound 516 (16.48 g). HPLC analysis showed that the solid purity was ≥99.98%. Mass spectrometry m / z: 773.2452 (theoretical value: 773.2467). Theoretical elemental content (%) C 57 H 31 N3O: C, 88.47; H, 4.04; N, 5.43. Measured elemental content (%): C, 88.45; H, 4.01; N, 5.44.

[0345] Synthesis Example 31: Preparation of Compound 533

[0346]

[0347] According to the preparation method of Synthesis Example 27, f-454 was replaced with an equimolar amount of f-533, and c-95 was replaced with an equimolar amount of c-23 to obtain compound 533 (17.70 g). HPLC analysis showed that the solid purity was ≥99.94%. Mass spectrometry m / z: 854.3283 (theoretical value: 854.3297). Theoretical elemental content (%) C 64 H 42 N2O: C, 89.90; H, 4.95; N, 3.28. Measured elemental content (%): C, 89.94; H, 4.93; N, 3.29.

[0348] Synthesis Example 32: Preparation of Compound 549

[0349]

[0350] According to the preparation method in Synthesis Example 27, f-454 was replaced with an equimolar amount of f-549, and c-95 was replaced with an equimolar amount of g-549, yielding compound 549 (16.59 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 778.2931 (theoretical value: 778.2922). Theoretical elemental content (%) C 58 H 30D4N2O: C, 89.43; H, 4.92; N, 3.60. Measured elemental content (%): C, 89.40; H, 4.91; N, 3.65.

[0351] Synthesis Example 33: Preparation of Compound 620

[0352]

[0353] Following the preparation method of Synthesis Example 27, f-454 was replaced with an equimolar amount of d-408, and c-95 was replaced with an equimolar amount of c-314, yielding compound 620 (17.91 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 877.2565 (theoretical value: 877.2552). Theoretical elemental content (%) C 64 H 35 N3S: C, 87.55; H, 4.02; N, 4.79. Measured elemental content (%): C, 87.56; H, 4.03; N, 4.76.

[0354] Synthesis Example 34: Preparation of Compound 649

[0355]

[0356] Following the preparation method of Synthesis Example 26, e-408 was replaced with an equimolar amount of e-649, and c-23 was replaced with an equimolar amount of c-304, yielding compound 649 (14.53 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 645.2244 (theoretical value: 645.2256). Theoretical elemental content (%) C 46 H 19 D7N2S: C, 85.55; H, 5.15; N, 4.34. Measured elemental content (%): C, 85.52; H, 5.16; N, 4.39.

[0357] Synthesis Example 35: Preparation of Compound 723

[0358]

[0359] According to the preparation method in Synthesis Example 27, d-408 was replaced with an equimolar amount of d-723, f-454 was replaced with an equimolar amount of f-723, and c-95 was replaced with an equimolar amount of g-723, yielding compound 723 (19.50 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 999.2882 (theoretical value: 999.2895). Theoretical elemental content (%) C 69 H 40F3N3S: C, 82.86; H, 4.03; N, 4.20. Measured elemental content (%): C, 82.83; H, 4.05; N, 4.22.

[0360] [Device Examples]

[0361] 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.

[0362] [Example 1]

[0363] The glass substrate was cleaned with distilled water and ultrasonically. 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 a vapor deposition machine. ITO / Ag / ITO was coated onto the glass substrate to form an anode. HI-1:HT-1 (mass ratio 3:97) was vapor deposited onto the anode to form a thickness of [missing information]. A hole injection layer. HT-1 is deposited on the hole injection layer to form a thickness of [missing information]. A hole transport layer is formed. A light-emitting layer is deposited on the hole transport layer, using BH-1 as the host material and 3wt% BD-1 doped with it, forming a layer with a thickness of [missing information]. The light-emitting layer is formed by evaporating ET-1:LiQ (mass ratio 1:1) onto the light-emitting layer to form a thickness of [missing information]. An electron transport layer is formed. LiF is deposited on the electron transport layer to form a layer with a thickness of [missing information]. An electron-injected layer was formed. Mg:Ag (mass ratio 1:9) was deposited on the electron-injected layer to form a layer with a thickness of [missing information]. The cathode. Compound 10 of the present invention is deposited on the cathode layer to form a layer with a thickness of... The covering layer forms an organic light-emitting device.

[0364]

[0365] [Examples 2-35]

[0366] Compounds 23, 48, 57, 66, 77, 95, 145, 180, 187, 230, 234, 255, 263, 267, 288, 296, 304, 314, 336, 338, 386, 390, 398, 405, 408, 454, 465, 499, 516, 533, 549, 620, 649, and 723 of this invention were used to replace compound 10 in Example 1 as hole transport layer materials. Otherwise, organic electroluminescent devices were prepared using the same preparation method as in Example 1.

[0367] [Comparative Examples 1-2]

[0368] Compounds P-1 and P-2 were used to replace compound 10 in Example 1 as hole transport layer materials. Otherwise, an organic electroluminescent device was prepared using the same preparation method as in Example 1.

[0369] The test environment was atmospheric, and the temperature was room temperature. The luminescence characteristics test results of the organic electroluminescent devices obtained by devices 1-35 and comparative examples 1-2 in the embodiments of the present invention are shown in Table 1 below.

[0370] Table 1:

[0371]

[0372]

[0373]

[0374] As shown in Table 1, when the aromatic amine compounds of the present invention are applied to the 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 aromatic amine compounds of the present invention are high-performance capping layer materials.

[0375] [Example 36]

[0376] 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 then deposited onto the anode to form a layer with a thickness of [missing information]. A hole injection layer. Compound 10 of the present invention is deposited on the hole injection layer to form a thickness of [thickness missing]. A hole transport layer is formed. A light-emitting layer is deposited on the hole transport layer, using GH-2 as the host material and doped with 6wt% GD-2, forming a layer with a thickness of [missing information]. The light-emitting layer. ET-2 is deposited on the light-emitting layer to form a thickness of [missing information]. An electron transport layer is formed. LiF is deposited on the electron transport layer to form a layer with a thickness of [missing information]. An electron-injected layer is formed. Al is deposited on the electron-injected layer to form a layer with a thickness of [missing information]. The cathode is used to form an organic light-emitting device.

[0377]

[0378] [Examples 37-70]

[0379] Compounds 23, 48, 57, 66, 77, 95, 145, 180, 187, 230, 234, 255, 263, 267, 288, 296, 304, 314, 336, 338, 386, 390, 398, 405, 408, 454, 465, 499, 516, 533, 549, 620, 649, and 723 of the present invention were used to replace compound 10 in Example 36 as hole transport layer materials. Otherwise, organic electroluminescent devices were prepared using the same preparation method as in Example 36.

[0380] [Comparative Examples 3-6]

[0381] Compounds P-3, P-4, P-5, and P-6 were used to replace compound 10 in Example 36 as hole transport layer materials. Otherwise, an organic electroluminescent device was prepared using the same preparation method as in Example 36.

[0382] The test environment was atmospheric, and the temperature was room temperature. The luminescence characteristics test results of the organic electroluminescent devices obtained in embodiments 36-70 and comparative embodiments 3-6 are shown in Table 2 below.

[0383] Table 2:

[0384]

[0385]

[0386] As shown in Table 2, when the aromatic amine compounds of the present invention are applied to the hole transport layer of organic electroluminescent devices, the devices exhibit higher luminous efficiency and longer lifespan compared to comparative compounds P-3 to P-6. The compounds of the present invention are high-performance hole transport layer materials.

[0387] [Example 71]

[0388] 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 a vapor deposition machine. Indium tin oxide (ITO) was coated onto the glass substrate to form an anode. HI-3 was then vapor deposited onto the anode to form a thickness of [missing information]. A hole injection layer was formed. HT-3 was deposited on the hole injection layer to form a thickness of [missing information]. A hole transport layer is formed. A light-emitting layer is deposited on the hole transport layer, using RH-3:compound 10 of this invention (mass ratio 1:1) as the host material and doped with 5wt% RD-3, forming a layer with a thickness of... The light-emitting layer is formed by evaporating ET-3:LiQ (mass ratio 1:1) onto the light-emitting layer to form a thickness of [missing information]. An electron transport layer is formed. LiF is deposited on the electron transport layer to form a layer with a thickness of [missing information]. An electron-injected layer is formed. Al is deposited on the electron-injected layer to form a layer with a thickness of [missing information]. The cathode is used to form an organic light-emitting device.

[0389]

[0390] [Examples 72-105]

[0391] Compounds 23, 48, 57, 66, 77, 95, 145, 180, 187, 230, 234, 255, 263, 267, 288, 296, 304, 314, 336, 338, 386, 390, 398, 405, 408, 454, 465, 499, 516, 533, 549, 620, 649, and 723 of this invention were used to replace compound 10 in Example 71 as the main material for the light-emitting layer. Otherwise, an organic electroluminescent device was prepared using the same preparation method as in Example 71.

[0392] [Comparative Examples 7-9]

[0393] Compounds P-7, P-8, and P-9 were used to replace compound 10 in Example 71 as the main material for the light-emitting layer. Otherwise, an organic electroluminescent device was prepared using the same preparation method as in Example 71.

[0394] The test environment was atmospheric, and the temperature was room temperature. The luminescence characteristics test results of the organic electroluminescent devices obtained by devices 71-105 in the embodiments of the present invention and comparative examples 7-9 are shown in Table 3 below.

[0395] Table 3:

[0396]

[0397]

[0398] As shown in Table 3, when the aromatic amine compounds of the present invention are applied to the light-emitting layer of organic electroluminescent devices, compared with comparative compounds P-7 to P-9, the devices have higher luminous efficiency and longer lifespan. The compounds of the present invention are high-performance light-emitting layer host materials.

[0399] 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 is selected from formula II; Ring A and ring B are independently selected from any one of the substituted or unsubstituted structures in group 1, and ring A and ring B are not simultaneously selected from substituted or unsubstituted structures. ; Group 1: X is selected from either O or S; The z is selected from C(R) t Any one of N; The R t Independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, 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-C17 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; Ar2 is selected from either Formula III or Formula IV; The v is independently selected from either C or N atoms, and when v is bonded to other groups, the v is selected from C atoms; The Y is selected from either a single bond or N(R4); R1, R2, and R3 are independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, 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 R4 is selected from any one of hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 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 value of e1 is selected from 0, 1, 2 or 3; the value of e2 is selected from 0, 1, 2, 3 or 4; when there are two or more R1s, the two or more R1s are the same as or different from each other; The Ar3 is selected from hydrogen, deuterium, substituted or unsubstituted silyl groups, substituted or unsubstituted C1-C25 alkyl groups, substituted or unsubstituted C3-C25 cycloalkyl groups, formula III, formula IV, or any one of the following groups: 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). p R q ), N(R z Any one of the following; The t is independently selected from either C or N atoms, and when t is bonded to other groups, the t is selected from C atoms; The t' is independently selected from either C or N atoms, and at most two of them are selected from N. When t' is bonded to other groups, the t' is selected from C atoms. The ring C is selected from substituted or unsubstituted C3~C10 alicyclic rings; The R a R a '、R p R q Independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, 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 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, or R p R q The links between them form substituted or unsubstituted rings; The R z It is selected from any one of hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 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, or 4; a2 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; a3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; a4 is selected from 0, 1, or 2; a5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; a6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; a7 is selected from 0, 1, 2, 3, 4, or 5; a8 is selected from 0, 1, 2, or 3; a9 is selected from 0, 1, 2, 3, 4, 5, or 6; 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 may be the same as or different from each other; The L1 is selected from a single bond or any one of the following groups, or a combination of two or more of the following groups: The u is independently selected from either C or N atoms, and at least one of them is selected from N. When u is bonded to other groups, the u is selected from C atoms. The e is independently selected from either C or N atoms, and when e is bonded to other groups, the e is selected from C atoms; 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). x R y ), N(R s Any one of the following; The ring D is selected from substituted or unsubstituted C3~C10 alicyclic rings; The R b R b '、R x R y Independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, 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 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, or R x R y The links between them form substituted or unsubstituted rings; The R w It is independently selected from any one of deuterium, fluorine, trifluoromethyl, cyano, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, and substituted or unsubstituted C3-C25 cycloalkyl; The R s It is selected from any one of hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 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; The q' is selected from 1, 2, 3 or 4; b1 is selected from 0, 1, 2, or 3; 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, 2, 3, or 4; b5 is selected from 0, 1, or 2; b6 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 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 may be the same as or different from each other; The w1 is selected from 1, 2, 3, or 4; when there are two or more R... w At that time, two or more R w They are the same as or different from each other; The " "" indicates the absence of a single bond. L2 and L3 are independently selected from any one of the following: a single bond, a substituted or unsubstituted C6-C30 arylene, a substituted or unsubstituted C2-C30 heteroarylene, a substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl group, or a substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroarylene ring fused cycloyl group. "" indicates that when there is no single bond, L2 and L3 are connected to form a substituted or unsubstituted ring.

2. The aromatic amine compound according to claim 1, characterized in that, The Ar1 is selected from any one of the following groups: X is independently selected from either O or S; The R t The group is independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, and the following groups, whether substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, n-decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, trimethylsilane. Triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane Benzocyclohexyl, naphthocyclohexyl, benzocycloheptyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyrene, perylene, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thiophene, benzothiophene, dibenzothiophene, benzene The following are all of the following: dibenzothiophene, pyrrole, indolyl, carbazolyl, oxazolyl, benzoxazolyl, dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzoimidazolyl, dibenzoimidazolyl, quinolinyl, benzoquinolinyl, isoquinolinyl, benzoisoquinolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenantholinyl, naphridyl, acridineyl, phenoxazinyl, and phenothiazinyl. t1 is selected from 0, 1, 2, 3, 4, 5, or 6; t2 is selected from 0, 1, 2, or 3; t3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; t4 is selected from 0, 1, 2, 3, or 4; t5 is selected from 0, 1, 2, 3, 4, or 5; t6 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; when there are two or more R... t At that time, two or more R t They may be the same as or different from each other.

3. The aromatic amine compound according to claim 1, characterized in that, The Ar2 (or formula III or formula IV) is selected from any of the following groups: The Y' is selected from N(R4); R1, R2, and R3 are independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, and substituted or unsubstituted groups of the following: methyl, ethyl, propyl, butyl, pentyl, hexyl, 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, benzocycloheptanyl ... Cyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthraceneyl, phenanthrene, triphenylene, pyrene, perylene, pyridyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thiopheneyl, benzothiopheneyl, dibenzothiopheneyl, benzodibenzothiopheneyl, 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 R4 is independently selected from hydrogen, deuterium, and substituted or unsubstituted groups of the following: methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, etc. The following is a list of compounds: methylsilyl, 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 e1 is selected from 0, 1, 2 or 3; the e2 is selected from 0, 1, 2, 3 or 4; the e3 is selected from 0, 1 or 2; the e4 is selected from 0 or 1; when there are two or more R1s, the two or more R1s are the same as or different from each other.

4. An aromatic amine compound according to claim 1, characterized in that, The Ar3 is selected from hydrogen, deuterium, substituted or unsubstituted silyl groups, substituted or unsubstituted C1-C25 alkyl groups, substituted or unsubstituted C3-C25 cycloalkyl groups, formula III, formula IV, or any one of the following groups: The R a R a '、R p R q The group is independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, and substituted or unsubstituted groups of the following: methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, 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, pyrrole, indole The following are all of the following: 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 z Selected from hydrogen, deuterium, and the following substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl Any one of silyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthraceneyl, phenanthrene, triphenylene, pyrene, perylene, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, and triazinyl; a1 is selected from 0, 1, 2, 3, or 4; a2 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; a3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; a4 is selected from 0, 1, or 2; a5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; a6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; a7 is selected from 0, 1, 2, 3, 4, or 5; a8 is selected from 0, 1, 2, or 3; a9 is selected from 0, 1, 2, 3, 4, 5, or 6; 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; 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; a'6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14; 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 is selected from a single bond or any one of the following groups, or a combination of two or more of the following groups: The R b R b '、R x R y The group is independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, and substituted or unsubstituted groups of the following: methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, 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, pyrrole, indole The following are all of the following: 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 w The group is independently selected from deuterium, fluorine, trifluoromethyl, cyano, or any of the following substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, and vinyldimethylsilyl. The R s Selected from hydrogen, deuterium, and the following substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl Any one of silyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthraceneyl, phenanthrene, triphenylene, pyrene, perylene, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, and triazinyl; b1 is selected from 0, 1, 2, or 3; 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, 2, 3, or 4; b5 is selected from 0, 1, or 2; b6 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 The same or different between each other, or two adjacent R b They connect with each other to form substituted or unsubstituted rings; 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.' 6. An aromatic amine compound according to claim 1, characterized in that, The L2 and L3 are independently selected from single bonds or any one of the following groups, or from two or more of the following groups: The r is independently selected from either C or N atoms, and when r is bonded to other groups, the r is selected from C atoms; Y6 and Y7 are independently selected from O, S, and N(R) k Any one of the following; The Y8, Y9, Y 10 Independently selected from O, S, C(R) i R j ), N(R k Any one of the following; The ring E is selected from substituted or unsubstituted C3~C10 alicyclic rings; The R c R c '、R i R j Independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, 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 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, or R i R j The links between them form substituted or unsubstituted rings; The R k It is selected from any one of hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 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 number n is selected from 1, 2, 3, or 4; c1 is selected from 0, 1, 2, 3, or 4; c2 is selected from 0, 1, 2, 3, 4, 5, or 6; c3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; c4 is selected from 0, 1, or 2; when there are two or more R... c At that time, two or more R c The same or different between each other, or two adjacent R c They connect with each other to form substituted or unsubstituted rings; The c'1 is selected from 0, 1, or 2; when there are two or more R... c At that time, two or more R c 'They are the same as or different from each other.' 7. An aromatic amine compound according to claim 1, characterized in that, The aromatic amine compound is selected from any one 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 comprises at least one of a hole transport layer and a light-emitting layer, wherein the at least one of the hole transport layer and the light-emitting layer comprises 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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