Arylamine compound and organic electroluminescent device thereof

By using aromatic amine compounds as hole transport layer and cover layer materials, the problems of unbalanced hole transport and insufficient cover layer performance are solved, the luminous efficiency and life of the organic electroluminescent device are improved, and light loss is reduced.

CN120682105APending Publication Date: 2025-09-23CHANGCHUN HYPERIONS TECH CO LTD
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Patent Information

Application Number
CN202511081061.X
Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Filing Date
2025-08-02
Publication Date
2025-09-23

AI Technical Summary

Technical Problem

The hole mobility of the hole transport layer material in organic electroluminescent devices is low, resulting in unbalanced electron and hole transport and low exciton recombination efficiency, which affects the luminous efficiency and service life. At the same time, the refractive index and glass transition temperature of the covering layer are low, and the improvement in light extraction efficiency is limited.

Method used

Aromatic amine compounds are used as hole transport layer materials and covering layer materials to improve hole transport capacity, reduce hole injection energy barriers, enhance carrier recombination efficiency, and improve device performance through good film forming properties and thermal stability.

Benefits of technology

The luminous efficiency and service life of the organic electroluminescent device are improved, light loss is reduced, and the overall performance of the device is improved.

✦ Generated by Eureka AI based on patent content.

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Patent Text Reader

Abstract

The invention provides an arylamine compound and an organic electroluminescent device thereof, and particularly relates to the technical field of organic photoelectric materials. The compound disclosed by the invention has good hole transport capability, and can improve the transport efficiency of holes in a device when being applied to a hole transport layer in the device, so that maximum recombination of current carriers is realized; and meanwhile, the energy barrier of the hole in the injection process is reduced, and the hole injection efficiency is improved, so that the luminous efficiency and the service life of the device are improved. The compound provided by the invention has good film-forming property and thermal stability, can improve optical efficiency and reduce loss of light reflected by a nearby electrode during luminescence when being used in a covering layer, and improves the performance of a device. 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.
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Description

Technical Field

[0001] The present invention relates to the technical field of organic photoelectric materials, in particular to an aromatic amine compound and an organic electroluminescent device thereof. Background Art

[0002] Organic Light Emitting Diode (OLED) has the characteristics of self-luminescence, wide viewing angle, short response time, high luminous efficiency, wide color gamut, low operating voltage, thin panel, flexible size design, flexible shape design and simple preparation method. It has been widely used in the fields of lighting and display and has been a hot research field in the past decade.

[0003] The luminescence mechanism of organic electroluminescent devices is that, driven by an applied voltage, electrons enter the electron transport layer from the cathode, and holes enter the hole transport layer from the anode. The two recombine in the light-emitting layer to produce excitons, which then radiatively transition back to the ground state and emit light. The structure of an OLED device generally includes an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, a cathode, a capping layer, and a charge generation layer.

[0004] Among them, the hole transport layer material in the organic electroluminescent device has the problems of low hole mobility, the electron and hole transport cannot reach a balance, and the excitons cannot be effectively recombinated, which affects the luminous efficiency and service life of the device; the refractive index and glass transition temperature of the covering layer in the organic electroluminescent device are low, resulting in a lack of obvious improvement in light extraction efficiency, and the luminous efficiency of the organic light-emitting device cannot be effectively improved.

[0005] Therefore, in order to solve the above problems, it is crucial to develop hole transport layer materials and cover layer materials for use in organic electroluminescent devices so that the devices have higher luminous efficiency and longer service life. Summary of the Invention

[0006] In order to solve the above problems, the present invention aims to provide an aromatic amine compound and an organic electroluminescent device thereof, which can improve the luminous efficiency of the organic electroluminescent device and extend the service life of the device.

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

[0008]

[0009] Wherein, R1, R2, and R3 are independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 Any one of an alicyclic ring and a fused ring of a C6-C30 aromatic ring; and at least one of R1, R2, and R3 is selected from any one of a halogen, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C3-C30 alicyclic ring and a fused ring of a C6-C30 aromatic ring;

[0010] Ar1, Ar2, Ar3, Ar4, Ar5, Ar6 are independently selected from Formula II or any one of the following groups; and at least one of Ar1, Ar2, Ar3, Ar4, Ar5, Ar6 is selected from Formula II;

[0011]

[0012] Said X1 is selected from C(R i R j )

[0013] Said X2 is selected from O, S, N (R s )

[0014] The v is independently selected from any one of CH and N;

[0015] The ring A is selected from a substituted or unsubstituted C3-C10 alicyclic ring;

[0016] The R i Any one independently selected from a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C3-C30 alicyclic group, and a fused cyclic group of a C6-C30 aromatic ring;

[0017] The R j 、R a 、R b 、R b' is independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring, or R i 、R j are connected to form a substituted or unsubstituted ring;

[0018] wherein R b The substituent in “substituted or unsubstituted” is selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, silyl, C1-C25 alkyl, C3-C9 cycloalkyl, C1-C25 heterocycloalkyl, C6-C30 aryl, C2-C30 heteroaryl, or a combination thereof;

[0019] The R s Any one independently selected from hydrogen, deuterium, tritium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;

[0020] The R i '、R j 'Independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl;

[0021] The a1 is selected from 0, 1, 2, 3 or 4; when there are two or more R a When two or more R a The same or different from each other, or two adjacent R a are connected to each other to form a substituted or unsubstituted ring;

[0022] b1 is selected from 0, 1, 2, 3, 4 or 5; b2 is selected from 0, 1, 2, 3 or 4; b3 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; b4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; b5 is selected from 0, 1 or 2; b6 is selected from 0, 1, 2 or 3; when there are two or more R b When two or more R b The same or different from each other, or two adjacent R bare connected to each other to form a substituted or unsubstituted ring;

[0023] The b'1 is selected from 0, 1 or 2; when there are two or more R b ', two or more R b 'same or different from each other;

[0024] The L1, L2, L3, L4, L5, and L6 are independently selected from a single bond or any one of the following groups or a combination of two or more of the following groups:

[0025]

[0026] Said X3 is selected from O, S, N (R t )

[0027] The z is independently selected from any one of CH and N;

[0028] The ring B is selected from a substituted or unsubstituted C3-C10 alicyclic ring;

[0029] The R c 、R c '、R p 、R q independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or R p 、R q are connected to form a substituted or unsubstituted ring;

[0030] The R t Any one independently selected from hydrogen, deuterium, tritium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;

[0031] Said q is selected from 1, 2, 3 or 4;

[0032] Said c1 is selected from 0, 1, 2, 3 or 4; said c2 is selected from 0, 1, 2, 3, 4, 5 or 6; said c3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said c4 is selected from 0, 1 or 2; when there are two or more R c When two or more R cThe same or different from each other, or two adjacent R c are connected to each other to form a substituted or unsubstituted ring;

[0033] The c'1 is selected from 0, 1 or 2; when there are two or more R c ', two or more R c ' are the same as or different from each other.

[0034] The present invention also provides an organic electroluminescent device comprising an anode, a cathode, and an organic layer located between the anode and the cathode or on the side of the cathode facing away from the anode, wherein the organic layer comprises at least one of the aromatic amine compounds described in the present invention.

[0035] Beneficial effects

[0036] The present invention provides an aromatic amine compound having good hole transport capability. When used in a hole transport layer in a device, the compound can improve the hole transport efficiency in the device and achieve maximum carrier recombination. At the same time, it reduces the energy barrier of holes during injection, improves the hole injection efficiency, and thus improves the luminous efficiency and service life of the device. The compound of the present invention has good film-forming properties and thermal stability. When used in a covering layer, it can improve optical efficiency and reduce light loss reflected by nearby electrodes during luminescence, thereby improving device performance. The compound preparation method provided by the present invention is simple, the raw materials are readily available, can meet industrialization needs, and has good industrialization prospects. DETAILED DESCRIPTION

[0037] The following is a clear and complete description of the technical solutions of the embodiments of the present invention. Obviously, the embodiments described are only part of the embodiments of the present invention, rather than all the embodiments. After reading this invention, modifications of various equivalent forms of the present invention by those skilled in the art all fall within the scope defined by the present invention.

[0038] Examples of the halogen atom according to the present invention may include fluorine, chlorine, bromine and iodine.

[0039] The aryl group described in the present invention refers to a group formed by removing a hydrogen atom from an aromatic carbon nucleus of an aromatic hydrocarbon molecule. It can be a monocyclic aryl group, a polycyclic 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. The monocyclic aryl group refers to an aryl group having only one aromatic ring in the molecule, such as, but not limited to, phenyl; the polycyclic aryl group refers to an aryl group containing two or more independent aromatic rings in the molecule, such as, but not limited to, biphenyl and terphenyl; the fused-ring aryl group refers to an aryl group containing two or more aromatic rings in the molecule and fused together by sharing two adjacent carbon atoms, such as, but not limited to, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, perylenyl, fluorenyl, benzofluorenyl, triphenylene, fluoranthenyl, spirobifluorenyl, etc.

[0040] The heteroaryl group described in the present invention refers to a group formed by replacing one or more aromatic carbon atoms in an aromatic group with a heteroatom, wherein the heteroatom includes but is not limited to oxygen, sulfur, nitrogen or phosphorus. The heteroaryl group can be a monocyclic heteroaryl group, a polycyclic heteroaryl group or a condensed-ring heteroaryl group, preferably having 2 to 30 carbon atoms, more preferably 2 to 18 carbon atoms, particularly preferably 2 to 15 carbon atoms, and most preferably 2 to 12 carbon atoms. The monocyclic heteroaryl groups include, but are not limited to, pyridyl, pyrimidinyl, triazine, furyl, thienyl, pyrrolyl, imidazolyl, etc.; the polycyclic heteroaryl groups include, but are not limited to, bipyridyl, bipyrimidinyl, phenylpyridyl, etc.; the fused-ring heteroaryl groups include, but are not limited to, quinolyl, isoquinolyl, indolyl, benzothienyl, benzofuranyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothienyl, benzodibenzothienyl, carbazolyl, benzocarbazolyl, acridinyl, 9,10-dihydroacridinyl, phenoxazinyl, phenothiazinyl, phenoxathiyl, etc., but are not limited to.

[0041] The fused cyclic radical of alicyclic ring of the present invention and aromatic ring refers to after alicyclic ring and aromatic ring are fused together and remove a hydrogen atom, the general name of the monovalent group obtained.Preferably there is 7 to 30 carbon atoms, more preferably 7 to 18 carbon atoms, most preferably 7 to 13 carbon atoms, the fused cyclic radical of described alicyclic ring and aromatic ring can comprise benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl etc., but is not limited to this.The attachment site of described fused cyclic radical can be on aromatic ring (such as phenyl ring), also can on alicyclic ring, but preferably on aromatic ring (such as phenyl ring).

[0042] The alkyl group described in the present invention refers to a monovalent group formed by removing a hydrogen atom from an alkane molecule, and may include a straight-chain alkyl group or a branched-chain alkyl group, preferably having 1 to 25 carbon atoms, more preferably 1 to 12 carbon atoms, more preferably 1 to 8 carbon atoms, and particularly preferably 1 to 6 carbon atoms. The straight-chain alkyl group includes, but is not limited to, methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl, etc.; the branched-chain alkyl group includes, but is not limited to, isopropyl, isobutyl, sec-butyl, tert-butyl, isomeric groups of n-pentyl, isomeric groups of n-hexyl, isomeric groups of n-heptyl, isomeric groups of n-octyl, isomeric groups of n-nonyl, isomeric groups of n-decyl, etc.

[0043] The cycloalkyl group herein refers to a monovalent group formed by removing a 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, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, and bornyl.

[0044] The heterocycloalkyl group of the present invention refers to a group formed by removing a hydrogen atom from a heterocyclic molecule whose ring atoms contain at least one heteroatom in addition to carbon atoms. The heteroatom includes, but is not limited to, oxygen, sulfur, nitrogen, or phosphorus. The group 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, but are not limited to, piperidinyl, piperazinyl, tetrahydropyrrolyl, morpholinyl, thiomorpholinyl, oxiranyl, and thiothioranyl.

[0045] The "substituted or unsubstituted silyl group" in the present invention refers to -Si(R n )3 groups, wherein each R n The same or different radicals are any one selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, 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, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, a fused ring group of a substituted or unsubstituted C1-C25 heterocycloalkane and a C6-C30 aromatic ring, and a fused ring group of a substituted or unsubstituted C3-C25 alicyclic ring and a C2-C30 heteroaromatic ring.

[0046] The substituents in the “substituted or unsubstituted” of the present invention may be independently selected from deuterium, tritium, 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, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, a substituted or unsubstituted C1-C12 alkoxy, a substituted or unsubstituted C1-C6 alkylthio, a substituted or unsubstituted C1-C12 alkylamino, a substituted or unsubstituted C6-C30 aryloxy, a substituted or unsubstituted C6-C30 arylamino, etc., but are not limited thereto, or two adjacent substituents may be connected to form a ring. Preferred are deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, C1-C25 alkyl, C3-C25 cycloalkyl, C6-C30 aryl, C2-C30 heteroaryl, C3-C30 alicyclic and C6-C30 aromatic fused ring, C1-C12 alkoxy, and specific examples include deuterium, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, propyl, butyl, cyclopropyl, cyclohexyl, adamantyl, norbornyl, phenyl, tolyl, mesityl, pentadeuterated phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, peryl, pyrenyl, fluoranthenyl, indenyl, dihydroindenyl, dihydronaphthyl, tetrahydronaphthyl, 9,9 -dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, spirobifluorenyl, carbazolyl, 9-phenylcarbazolyl, carbazolindolyl, pyrrolyl, furyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, oxazolyl, thiazolyl, imidazolyl, benzoxazolyl, benzothiazolyl, benzotriazolyl, benzimidazolyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, phenothiazinyl, phenoxazinyl, acridinyl, benzocyclobutanyl, benzocyclobutenyl, benzocyclopentanyl, benzocyclopentenyl, benzocyclohexanyl, benzocyclohexenyl, etc., but are not limited thereto. When there are multiple substituents, the multiple substituents may be the same as or different from each other; or adjacent substituents may be connected to form a ring.

[0047] In the present specification, "-*" means a portion connected to another substituent. "-*" can be connected to any optional position of the group / fragment to which it is connected.

[0048] In this specification, when a substituent or a bond at a connection site runs through two or more rings, it indicates that it can be connected to any of the two or more rings, specifically any of the corresponding optional sites of the rings. For example, Can represent Can represent And so on.

[0049] In the present specification, when the position of a substituent or a bonding site on a ring is not fixed, it means that it can be bonded to any of the optional sites of the ring.

[0050] For example, Can represent Can represent Can represent And so on.

[0051] The term "linked to form a ring" as used herein refers to two groups being linked to each other via a chemical bond and optionally aromatized. For example:

[0052]

[0053] In the present invention, the ring formed by connection can be an aromatic ring system, an aliphatic ring system or a ring system formed by fusion of the two. The ring formed by 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, cyclopentane acene, cyclohexene, cyclohexane, cyclohexane acene, quinoline, isoquinoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, phenanthrene or pyrene, but is not limited thereto.

[0054] In the present invention, the term "at least one" includes one, two, three or more. The term "more than two" includes two, three, four or more, where permitted.

[0055] The present invention provides an aromatic amine compound having a structure represented by Formula I:

[0056]

[0057] Wherein, R1, R2, and R3 are independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 Any one of an alicyclic ring and a fused ring of a C6-C30 aromatic ring; and at least one of R1, R2, and R3 is selected from any one of a halogen, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C3-C30 alicyclic ring and a fused ring of a C6-C30 aromatic ring;

[0058] Ar1, Ar2, Ar3, Ar4, Ar5, Ar6 are independently selected from Formula II or any one of the following groups; and at least one of Ar1, Ar2, Ar3, Ar4, Ar5, Ar6 is selected from Formula II;

[0059]

[0060] Said X1 is selected from C(R i R j )

[0061] Said X2 is selected from O, S, N (R s )

[0062] The v is independently selected from any one of CH and N;

[0063] The ring A is selected from a substituted or unsubstituted C3-C10 alicyclic ring;

[0064] The R i Any one independently selected from a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C3-C30 alicyclic group, and a fused cyclic group of a C6-C30 aromatic ring;

[0065] The R j 、R a 、R b 、R b ' is independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring, or R i 、R j are connected to form a substituted or unsubstituted ring;

[0066] wherein R b The substituent in “substituted or unsubstituted” is selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, silyl, C1-C25 alkyl, C3-C9 cycloalkyl, C1-C25 heterocycloalkyl, C6-C30 aryl, C2-C30 heteroaryl, or a combination thereof;

[0067] The R sAny one independently selected from hydrogen, deuterium, tritium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;

[0068] The R i '、R j 'Independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl;

[0069] The a1 is selected from 0, 1, 2, 3 or 4; when there are two or more R a When two or more R a The same or different from each other, or two adjacent R a are connected to each other to form a substituted or unsubstituted ring;

[0070] b1 is selected from 0, 1, 2, 3, 4 or 5; b2 is selected from 0, 1, 2, 3 or 4; b3 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; b4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; b5 is selected from 0, 1 or 2; b6 is selected from 0, 1, 2 or 3; when there are two or more R b When two or more R b The same or different from each other, or two adjacent R b are connected to each other to form a substituted or unsubstituted ring;

[0071] The b'1 is selected from 0, 1 or 2; when there are two or more R b ', two or more R b 'same or different from each other;

[0072] The L1, L2, L3, L4, L5, and L6 are independently selected from a single bond or any one of the following groups or a combination of two or more of the following groups:

[0073]

[0074] Said X3 is selected from O, S, N (R t )

[0075] The z is independently selected from any one of CH and N;

[0076] The ring B is selected from a substituted or unsubstituted C3-C10 alicyclic ring;

[0077] The R c 、R c '、R p 、R q independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or R p 、R q are connected to form a substituted or unsubstituted ring;

[0078] The R t Any one independently selected from hydrogen, deuterium, tritium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;

[0079] Said q is selected from 1, 2, 3 or 4;

[0080] Said c1 is selected from 0, 1, 2, 3 or 4; said c2 is selected from 0, 1, 2, 3, 4, 5 or 6; said c3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said c4 is selected from 0, 1 or 2; when there are two or more R c When two or more R c The same or different from each other, or two adjacent R c are connected to each other to form a substituted or unsubstituted ring;

[0081] The c'1 is selected from 0, 1 or 2; when there are two or more R c ', two or more R c ' are the same as or different from each other.

[0082] Preferably, the Select any one of the following structures:

[0083]

[0084] Preferably, the formula I is selected from any one of the following structures:

[0085]

[0086]

[0087] Ar1, Ar2, Ar3, Ar4, Ar5, Ar6, L1, L2, L3, L4, L5, L6, R1, R2, R3, R a The definitions of X1, a1 are the same as those in Formula I.

[0088] Preferably, the formula II (including the above structural formula ) is selected from any one of the following groups:

[0089]

[0090] The R i independently selected from the following substituted or unsubstituted groups: benzocyclopropanyl, naphthocyclopropanyl, benzocyclobutanyl, naphthocyclobutanyl, benzocyclopentanyl, naphthocyclopentanyl, benzocyclohexanyl, naphthocyclohexanyl, benzocycloheptanyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, perylenyl, pyridyl, pyrimidinyl, pyrazinyl , pyridazinyl, triazinyl, furanyl, thienyl, pyrrolyl, oxazolyl, benzoxazolyl, dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzimidazolyl, dibenzimidazolyl, quinolyl, benzoquinolyl, isoquinolyl, benzoisoquinolyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenanthrolinyl, naphthyridinyl, indolyl, acridinyl, phenoxazinyl, phenothiazinyl;

[0091] The R j 、R a 、R aindependently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropanyl, naphthocyclopropanyl, benzocyclobutanyl, naphthocyclobutanyl, benzocyclopentanyl, naphthocyclopentanyl , benzocyclohexyl, naphthiocyclohexyl, benzocycloheptyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, perylenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thienyl, pyrrolyl, oxazolyl, benzoxazolyl, dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzimidazolyl, dibenzimidazolyl, quinolyl, benzoquinolyl, isoquinolyl, benzoisoquinolyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenanthrolinyl, naphthyridinyl, indolyl, acridinyl, phenoxazinyl, phenothiazinyl;

[0092] The R v independently selected from hydrogen, deuterium, tritium, substituted or unsubstituted methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl , vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropanyl, naphthocyclopropanyl, benzocyclobutanyl, naphthocyclobutanyl, benzocyclopentanyl, naphthocyclopentanyl, benzocyclohexanyl, naphthocyclohexanyl, benzocycloheptanyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, perylenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl;

[0093] The a1 is selected from 0, 1, 2, 3 or 4; the a2 is selected from 0, 1, 2 or 3; when there are two or more R a When two or more R a The same or different from each other, or two adjacent R aThey are connected to each other to form substituted or unsubstituted: benzene ring, naphthalene ring, pyridine ring, pyrimidine ring, cyclopentane ring, cyclohexane ring;

[0094] a'1 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; a'2 is selected from 0, 1, 2, 3, 4, 5 or 6; a'3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; a'4 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 ', two or more R a ' are the same as or different from each other.

[0095] More preferably, the formula II (including ) is selected from any one of the following groups:

[0096]

[0097]

[0098]

[0099]

[0100]

[0101] Preferably, when Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 are not of formula II, they are independently selected from any one of the following groups;

[0102]

[0103]

[0104] The R b 、R bindependently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropanyl, naphthocyclopropanyl, benzocyclobutanyl, naphthocyclobutanyl, benzocyclopentanyl, naphthocyclopentanyl , benzocyclohexyl, naphthiocyclohexyl, benzocycloheptyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, perylenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thienyl, pyrrolyl, oxazolyl, benzoxazolyl, dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzimidazolyl, dibenzimidazolyl, quinolyl, benzoquinolyl, isoquinolyl, benzoisoquinolyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenanthrolinyl, naphthyridinyl, indolyl, acridinyl, phenoxazinyl, phenothiazinyl;

[0105] wherein R b The substituents in the "substituted or unsubstituted" are selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidine any one of 1,2-diphenylmethane, ...

[0106] The R sindependently selected from hydrogen, deuterium, tritium, substituted or unsubstituted methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl , vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropanyl, naphthocyclopropanyl, benzocyclobutanyl, naphthocyclobutanyl, benzocyclopentanyl, naphthocyclopentanyl, benzocyclohexanyl, naphthocyclohexanyl, benzocycloheptanyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, perylenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl;

[0107] The R i '、R j 'Independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl any one;

[0108] b1 is selected from 0, 1, 2, 3, 4 or 5; b2 is selected from 0, 1, 2, 3 or 4; b3 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; b4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; b5 is selected from 0, 1 or 2; b6 is selected from 0, 1, 2 or 3; b7 is selected from 0 or 1; when there are two or more R b When two or more R b The same or different from each other, or two adjacent R b They are connected to each other to form substituted or unsubstituted: benzene ring, naphthalene ring, pyridine ring, pyrimidine ring, cyclopentane ring, cyclohexane ring;

[0109] The b'1 is selected from 0, 1 or 2; when there are two or more R b ', two or more R b ' are the same as or different from each other.

[0110] More preferably, when Ar1, Ar2, Ar3, Ar4, Ar5, Ar6 (especially Ar2, Ar4, Ar6) are not of formula II, they are independently selected from any one of the following groups:

[0111]

[0112]

[0113]

[0114] Preferably, L1, L2, L3, L4, L5, and L6 are independently selected from a single bond or any one of the following groups or a combination of two or more of the following groups:

[0115]

[0116]

[0117] The R c 、R c '、R p 、R q independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropanyl, naphthocyclopropanyl, benzocyclobutanyl, naphthocyclobutanyl, benzocyclopentanyl, naphthocyclopentanyl , benzocyclohexyl, naphthiocyclohexyl, benzocycloheptyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, perylenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thienyl, pyrrolyl, oxazolyl, benzoxazolyl, dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzimidazolyl, dibenzimidazolyl, quinolyl, benzoquinolyl, isoquinolyl, benzoisoquinolyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenanthrolinyl, naphthyridinyl, indolyl, acridinyl, phenoxazinyl, phenothiazinyl;

[0118] The R tindependently selected from hydrogen, deuterium, tritium, substituted or unsubstituted methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl , vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropanyl, naphthocyclopropanyl, benzocyclobutanyl, naphthocyclobutanyl, benzocyclopentanyl, naphthocyclopentanyl, benzocyclohexanyl, naphthocyclohexanyl, benzocycloheptanyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, perylenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl;

[0119] Said c1 is selected from 0, 1, 2, 3 or 4; said c2 is selected from 0, 1, 2, 3, 4, 5 or 6; said c3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said c4 is selected from 0, 1 or 2; said c5 is selected from 0, 1, 2 or 3; said c6 is selected from 0 or 1; when there are two or more R c When two or more R c The same or different from each other, or two adjacent R c They are connected to each other to form substituted or unsubstituted: benzene ring, naphthalene ring, pyridine ring, pyrimidine ring, cyclopentane ring, cyclohexane ring;

[0120] The c'1 is selected from 0, 1 or 2; the c'2 is selected from 0, 1, 2, 3 or 4; the c'3 is selected from 0, 1, 2, 3, 4, 5 or 6; the c'4 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the c'5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; the c'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 c ', two or more R c ' are the same as or different from each other.

[0121] More preferably, L1, L2, L3, L4, L5, and L6 are independently selected from a single bond or any one of the following groups or a combination of two or more of the following groups:

[0122]

[0123]

[0124] Preferably, R1, R2, and R3 are independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropanyl, naphthoxycyclopropanyl, benzocyclobutanyl, naphthoxycyclobutanyl, benzocyclocyclobutanyl, Pentyl, naphthocyclopentyl, benzocyclohexyl, naphthocyclohexyl, benzocycloheptyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, perylenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thienyl, pyrrolyl, oxazolyl, benzoxazolyl, dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzimidazolyl, dibenzimidazolyl, quinolinyl, benzoquinolinyl, isoquinolinyl, benzoisoquinolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenanthrolinyl, naphthyridinyl, indolyl, acridinyl, phenoxazinyl, phenothiazinyl any one of; and at least one (1, 2 or 3) of R1, R2 and R3 is selected from halogen, cyano, substituted or unsubstituted groups: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutane alkenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, perylenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furyl, benzofuranyl, dibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, pyrrolyl, indolyl, oxazolyl, benzo any one of oxazolyl, dibenzooxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzimidazolyl, dibenzimidazolyl, quinolyl, benzoquinolyl, isoquinolyl, benzoisoquinolyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenanthrolinyl, naphthyridinyl, indolyl, acridinyl, phenoxazinyl, and phenothiazinyl.

[0125] More preferably, R1, R2, and R3 are independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropanyl, naphthocyclopropanyl, benzocyclobutanyl, naphthocyclobutanyl, benzocyclopentanyl, naphthocyclopentanyl, cyclopentanyl, benzocyclohexanyl, naphthocyclohexanyl, benzocycloheptanyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, perylenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thienyl, pyrrolyl, oxazolyl, benzoxazolyl, dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzimidazolyl, dibenzimidazolyl, quinolyl, benzoquinolyl, isoquinolyl, benzoisoquinolyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenanthrolinyl, naphthyridinyl, indolyl, acridinyl, phenoxazinyl, phenothiazinyl any one of; and at least one (1, 2 or 3) of R1, R2 and R3 is selected from halogen, cyano, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclocyclobutenyl, benzocyclocyclohexenyl, benzocycloheptenyl ... any one of pentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, perylenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furyl, benzofuranyl, dibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, pyrrolyl, indolyl, oxazolyl, benzoxazolyl, dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzimidazolyl, dibenzimidazolyl, quinolyl, benzoquinolyl, isoquinolyl, benzoisoquinolyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenanthrolinyl, naphthyridinyl, indolyl, acridinyl, phenoxazinyl, and phenothiazinyl.

[0126] Preferably, R1, R2, and R3 are all selected from halogen.

[0127] Most preferably, the formula I is selected from any one of the following structures:

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170] The above lists some specific structural forms of the aromatic amine compounds represented by Chemical Formula I of the present invention, but the present invention is not limited to these listed chemical structures. All chemical structures based on the structure shown in Chemical Formula I and with substituents as defined above are included.

[0171] The present invention provides an organic electroluminescent device comprising an anode, a cathode, and an organic layer located between the anode and the cathode or on the side of the cathode facing away from the anode, wherein the organic layer contains at least one of the aromatic amine compounds described in the present invention.

[0172] 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 covering layer, and at least one of the hole transport layer and the covering layer comprises at least one of the aromatic amine compounds described in the present invention.

[0173] More preferably, the hole transport layer comprises a first hole transport layer and a second 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 at least one of the first hole transport layer and the second hole transport layer comprises at least one of the aromatic amine compounds described in the present invention.

[0174] More 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, and 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 the present invention.

[0175] More preferably, the organic layer is located between the anode and the cathode, the organic layer comprises a first light-emitting portion, a second light-emitting portion and a charge generation layer, the first light-emitting portion is located between the anode and the cathode, the second light-emitting portion is located between the first light-emitting portion and the cathode, the charge generation layer is located between the first light-emitting portion and the second light-emitting portion, and the charge generation layer comprises at least one of the aromatic amine compounds described in the present invention.

[0176] More preferably, the charge generation layer is composed of an N-type charge generation layer arranged adjacent to the first light-emitting portion and a P-type charge generation layer arranged adjacent to the second light-emitting portion, and the P-type charge generation layer contains at least one of the aromatic amine compounds described in the present invention.

[0177] Preferably, the organic layer is located on a side of the cathode facing away from the anode, and the organic layer comprises a covering layer, and the covering layer comprises at least one of the aromatic amine compounds described in the present invention.

[0178] The anode of the present invention preferably has a large work function, including metals, alloys, conductive compounds, and mixtures thereof. Specific examples include, but are not limited to, indium tin oxide (ITO), indium zinc oxide (IZO), indium oxide (InO), zinc oxide (ZnO), zinc oxide:aluminum (ZnO / Al), silver / indium tin oxide (Ag / ITO), indium tin oxide / silver / indium tin oxide (ITO / Ag / ITO), aluminum / nickel (Al / Ni), aluminum / platinum (Al / Pt), gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), and the like.

[0179] The hole injection layer of the present invention is preferably made of a material with high hole injection properties. In addition to the aromatic amine compound provided by the present invention, metal compounds, aromatic amine derivatives, polycyano conjugated organic compounds, polymers, etc. are also included. Specific examples include but are not limited to 4,4',4"-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4"-tris(N-3-methylphenyl-N-phenylamino)triphenylamine (m-MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (DNTPD), molybdenum trioxide ( MoO3), vanadium pentoxide (V2O5), tungsten trioxide (WO3), nickel oxide (NiO), titanium dioxide (TiO2), copper phthalocyanine (CuPc), oxytitanium 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. The aromatic amine compound of the present invention is preferred.

[0180] The hole transport layer of the present invention is preferably made of a material with high hole transport properties. In addition to the aromatic amine compound provided by the present invention, other materials that can be used include aromatic amine derivatives, biphenylenediamine derivatives, carbazole derivatives, fluorene derivatives, and the like. Specific examples of the hole transport material include, but are not limited to, N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), N4,N4,N4',N4'-tetrakis([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine, 4,4'-cyclohexylbis[N,N-bis(4-methylphenyl)aniline] (TAPC), N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), 2,2,7,7-tetrakis(diphenylamino)-9,9-spirobifluorene (Spiro-TAD), 4,4',4"-tris(carbazol-9-yl)triphenylamine (TCTA), and the like. The aromatic amine compounds of the present invention are preferred.

[0181] The electron blocking layer of the present invention preferably has a material with good hole transport ability and the ability to block electrons. In addition to the aromatic amine compounds provided by the present invention, aromatic amine derivatives, carbazole derivatives, etc. are also included. Specific examples of the electron blocking layer include, but are not limited to, 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 the present invention are preferred.

[0182] The light-emitting layer of the present invention may include a single material, a host material (also called a matrix material) and a dopant material (also called a guest material). The light-emitting layer material may include multiple host materials and multiple dopant materials. Regarding the type of dopant material, it can be a fluorescent material, or it can be a phosphorescent material or a TADF material. Fluorescent dopant materials may include: fused polycyclic aromatic derivatives, styrylamine 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 the present invention, the host material may also include fused aromatic ring derivatives, heterocyclic compounds, etc. Fused aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene derivatives, fluoranthene derivatives, etc., and heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, pyrimidine derivatives, etc., such as Alq3, BAlq, TPBi, TPD, CBP, TCTA, ADN, etc., but are not limited thereto.

[0183] The hole blocking layer of the present invention can generally be formed using 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, phenanthroline derivatives, polymer compounds, rare earth derivatives, triazine derivatives, quinoline derivatives, phenanthroline derivatives, azobenzene derivatives, anthrone derivatives, and the like. Specific examples of the hole blocking layer material include, but are not limited to, BCP, BAlq, TPBi, and the like, but are not limited thereto.

[0184] The electron transport layer of the present invention is preferably made of a material with high electron transport properties, including metal complexes, pyridine derivatives, imidazole derivatives, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, and the like. 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), bis(2-methyl-8-hydroxyquinoline)(4-phenylphenol)aluminum(III) (BAlq), etc.

[0185] The electron injection layer of the present invention is preferably made of a material with high electron injection properties, including metals, metal salts, metal oxides, etc. The electron injection material includes but is not limited to lithium fluoride (LiF), 8-hydroxyquinoline lithium (Liq), sodium fluoride (NaF), rubidium fluoride (RbF), cesium fluoride (CsF), magnesium phosphide (MgP), cesium carbonate (Cs2CO3), lithium oxide (Li2O), lithium boron oxide (LiBO2), aluminum oxide (Al2O3), vanadium oxide (V2O5), lithium (Li), cesium (Cs), etc.

[0186] The cathode of the present invention preferably has a material with a low work function. Cathode materials of the present invention include, but are not limited to, metals, metal alloys, conductive compounds, and mixtures thereof. Specific examples of cathode materials include, but are not limited to, aluminum (Al), silver (Ag), gold (Au), lead (Pb), lithium (Li), magnesium (Mg), magnesium-silver alloys (Mg:Al), lithium-aluminum alloys (Li:Al), and calcium-silver (Ca / Ag).

[0187] The cover layer material of the present invention is preferably a material having optical coupling properties, including imidazole derivatives, oxazole derivatives, thiazole derivatives, aromatic amine derivatives, and the like. Specific examples of the cover layer material include, but are not limited to, tris(8-hydroxyquinolinol)aluminum(III) (Alq3), N,N'-di(naphthalene-1-yl)-N,N'-di(phenyl)-2,2'-dimethylbenzidine (NPD), 4,4'-di(9-carbazole)biphenyl (CBP), N4,N4,N4',N4'-tetrakis(4-methoxyphenyl)-[1,1'-biphenyl]-4,4'-diamine (MeO-TPD), lithium fluoride, magnesium fluoride, and the like.

[0188] The N-type charge generation layer material of the present invention may include one of the following materials or a combination thereof: 4,7-diphenyl-1,10-phenanthroline (Bphen), 2,9-bis(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline (NBphen), 1,3,5-tris(p-pyridin-3-yl-phenyl)benzene (TpPyPB), 2,4,6-tris(3'-(pyridin-3-yl)biphenyl-3-yl)1,3,5-triazine (TmPPPyTz), etc., but is not limited thereto. Furthermore, in addition to the above materials, the N-type charge generation material may also include a dopant material. For example, alkali metals such as Li, Cs, K, Rb, Na, or Fr, etc., but are not limited thereto, or alkaline earth metals such as Be, Mg, Ca, Sr, Ba, or Ra, etc., but are not limited thereto.

[0189] The P-type charge generation layer material of the present invention may include one of the following materials or a combination thereof: the aromatic amine compound provided by the present invention, N,N'-di(naphthalene-1-yl)-N,N'-di(phenyl)-2,2'-dimethylbenzidine (NPD), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (HATCN), etc., preferably the aromatic amine compound of the present invention. In addition to the above materials, the P-type charge generation material may also include a doping material. Specific examples of the doping material may include vanadium pentoxide (V2O5), 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanodimethyl-p-benzoquinone (F4-TCNQ), etc., but are not limited thereto.

[0190] The following is a method for preparing the compound represented by Chemical Formula I of the present invention, but the preparation method of the present invention is not limited thereto. The core structure of the compound of Chemical Formula I can be prepared by the reaction scheme shown below. The substituents can be bonded using methods known in the art, and the type and position of the substituents or the number of substituents can be varied according to techniques known in the art.

[0191] [Synthetic route]

[0192] Preparation of compounds of formula I:

[0193]

[0194] When R2 and R3 are hydrogen, formula e is prepared by the following route:

[0195]

[0196]

[0197] when At the same time, the compound of formula I is prepared by the following route:

[0198]

[0199] when At the same time, the compound of formula I is prepared by the following route:

[0200]

[0201] Xa, Xb, Xc, Xd, Xe, Xf, Xg, and Xh are each independently selected from any one of Cl, Br, and I; the definitions of Ar1, Ar2, Ar3, Ar4, Ar5, Ar6, L1, L2, L3, L4, L5, L6, R1, R2, and R3 are the same as those above.

[0202] Description of raw materials, reagents and characterization equipment:

[0203] The present invention has no particular limitation on the sources of the raw materials and reagents used in the following examples. They may be commercially available products or prepared by methods well known to those skilled in the art.

[0204] Mass spectrometry was performed using a British Waters G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer, with chloroform as the solvent;

[0205] The elemental analysis was performed using a VarioELcube organic element analyzer from Elementar, Germany, with a sample mass of 5 to 10 mg.

[0206] [Synthesis Example 1] Synthesis of Compound 30

[0207]

[0208] Synthetic intermediate A-30

[0209] Under nitrogen, a-30 (50.29 g, 150.00 mmol), b-30 (36.80 g, 150.00 mmol), and sodium tert-butoxide (21.62 g, 225.00 mmol) dissolved in 1000 ml of toluene were added to a reaction flask. Pd(dppf)Cl2 (1.10 g, 1.50 mmol) was added with stirring, and the mixture was heated under reflux for 3.5 h. After the reaction, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallization from ethyl acetate gave intermediate A-30 (62.21 g, 83% yield); HPLC purity ≥99.73%. Mass spectrum: m / z: 499.2309 (theoretical value: 499.2300).

[0210] Synthetic intermediate B-30

[0211] Under nitrogen, a reaction flask containing c-30 (18.84 g, 120.00 mmol), d-30 (11.18 g, 120.00 mmol), and sodium tert-butoxide (17.30 g, 180.00 mmol) dissolved in 960 ml of toluene was added. Pd(OAc)2 (0.27 g, 1.20 mmol) and P(t-Bu)3 (4.80 mL, 2.40 mmol, in a 0.5 M solution in toluene) were added with stirring. The mixture was heated under reflux for 4.5 h. After completion of the reaction, 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 removed under reduced pressure. Recrystallization from toluene / methanol (6:1 volume ratio) afforded intermediate B-30 (16.45 g, 81% yield); HPLC purity ≥99.78%. Mass spectrum m / z: 169.0872 (theoretical value: 169.0891).

[0212] Synthetic intermediate C-30

[0213] Under nitrogen, e-30 (12.08 g, 40.00 mmol), A-30 (19.99 g, 40.00 mmol), and sodium tert-butoxide (5.77 g, 60.00 mmol) dissolved in 320 ml of toluene were added to a reaction flask. Pd(OAc)2 (0.09 g, 0.40 mmol) and P(t-Bu)3 (1.6 mL, 0.80 mmol, in a 0.5 M solution in toluene) were added with stirring. The mixed solution was heated under reflux for 6 h. After the reaction was completed, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. The mixture was purified by silica gel column chromatography using n-hexane / dichloromethane (volume ratio 7:1) to obtain intermediate C-30 (22.49 g, 78% yield); HPLC purity ≥99.84%. Mass spectrum m / z: 719.2159 (theoretical value: 719.2147).

[0214] Synthesis of compound 30

[0215] Under nitrogen, C-30 (14.41 g, 20.00 mmol), B-30 (6.77 g, 40.00 mmol), and sodium tert-butoxide (3.84 g, 40.00 mmol) dissolved in 200 ml of toluene were added to a reaction flask. Pd2(dba)3 (0.37 g, 0.40 mmol) and X-Phos (0.19 g, 0.40 mmol) were added with stirring, and the mixed solution of the above reactants was heated under reflux for 6.5 h. After the reaction was completed, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallization from toluene gave compound 30 (14.40 g, 73%). The solid purity was ≥99.96% as determined by HPLC. Mass spectrum m / z: 985.4381 (theoretical value: 985.4396). Theoretical element content (%): C 74 H 55 N3: C, 90.12; H, 5.62; N, 4.26. Measured element content (%): C, 90.14; H, 5.61; N, 4.28.

[0216] [Synthesis Example 2] Synthesis of Compound 116

[0217]

[0218] Synthetic intermediate e-116

[0219] Under nitrogen, intermediate f-116 (28.14 g, 80.00 mmol), g-116 (16.73 g, 80.00 mmol), Pd(PPh3)4 (1.39 g, 1.20 mmol), KOAc (15.70 g, 160.00 mmol), and 800 mL of a 4:1:1 toluene / ethanol / water mixture were added sequentially to a reaction flask. The mixture was stirred and heated under reflux for 7 hours. After the reaction, the mixture was cooled to room temperature and filtered to obtain a filter cake, which was rinsed with ethanol and recrystallized from toluene to obtain intermediate e-116 (20.14 g, 82% yield). HPLC analysis of the solid revealed a purity of ≥99.86%. Mass spectrum: m / z: 304.9435 (theoretical value: 304.9422).

[0220] According to the preparation method of Synthesis Example 1, a-30 was replaced with an equal molar amount of a-116, b-30 was replaced with an equal molar amount of d-30, and e-30 was replaced with an equal molar amount of e-116 to obtain compound 116 (12.08 g). The solid purity was ≥99.95% as determined by HPLC. Mass spectrum m / z: 838.4096 (theoretical value: 838.4084). Theoretical element content (%): C 62 H 42 D5N3: C, 88.75; H, 6.25; N, 5.01. Measured element content (%): C, 88.77; H, 6.23; N, 5.03.

[0221] [Synthesis Example 3] Synthesis of Compound 184

[0222]

[0223] According to the preparation method of Synthesis Example 1, a-30 was replaced with an equal molar amount of a-184, b-30 was replaced with an equal molar amount of d-30, and c-30 was replaced with an equal molar amount of c-184 to obtain compound 184 (14.89 g). The solid purity was ≥99.94% as determined by HPLC. Mass spectrum m / z: 1047.4567 (theoretical value: 1047.4552). Theoretical element content (%): C 79 H 57 N3: C, 90.51; H, 5.48; N, 4.01. Measured element content (%): C, 90.53; H, 5.46; N, 4.05.

[0224] [Synthesis Example 4] Synthesis of Compound 216

[0225]

[0226] According to the preparation method of Synthesis Example 1, a-30 was replaced with an equal molar amount of a-216, and b-30 was replaced with an equal molar amount of b-216 to obtain compound 216 (14.72 g). The solid purity was ≥99.96% as determined by HPLC. Mass spectrum m / z: 1021.4383 (theoretical value: 1021.4396). Theoretical element content (%): C 77 H 55 N3: C, 90.47; H, 5.42; N, 4.11. Measured element content (%): C, 90.50; H, 5.45; N, 4.16.

[0227] [Synthesis Example 5] Synthesis of Compound 227

[0228]

[0229] According to the preparation method of Synthesis Example 1, a-30 was replaced with an equal molar amount of a-227, and b-30 was replaced with an equal molar amount of b-227 to obtain Compound 227 (14.15 g). The solid purity was ≥99.97% as determined by HPLC. Mass spectrum m / z: 995.4226 (theoretical value: 995.4239). Theoretical element content (%): C 75 H 53 N3: C, 90.42; H, 5.36; N, 4.22. Measured element content (%): C, 90.41; H, 5.39; N, 4.26.

[0230] [Synthesis Example 6] Synthesis of Compound 249

[0231]

[0232] According to the preparation method of Synthesis Example 1, a-30 was replaced with an equal molar amount of a-216, b-30 was replaced with an equal molar amount of d-30, and c-30 was replaced with an equal molar amount of c-249 to obtain compound 249 (13.67 g). The solid purity was ≥99.95% as determined by HPLC. Mass spectrum m / z: 975.3836 (theoretical value: 975.3825). Theoretical element content (%): C 71 H 49 N3O2: C, 87.36; H, 5.06; N, 4.30. Measured element content (%): C, 87.32; H, 5.09; N, 4.34.

[0233] [Synthesis Example 7] Synthesis of Compound 308

[0234]

[0235] According to the preparation method of Synthesis Example 1, a-30 was replaced with an equal molar amount of a-308, b-30 was replaced with an equal molar amount of d-30, and e-30 was replaced with an equal molar amount of e-308 to obtain compound 308 (12.82 g). The solid purity was ≥99.96% as determined by HPLC. Mass spectrum m / z: 941.4179 (theoretical value: 941.4165). Theoretical element content (%): C 68 H 55 N3Si: C, 86.68; H, 5.88; N, 4.46. Measured element content (%): C, 86.64; H, 5.82; N, 4.49.

[0236] [Synthesis Example 8] Synthesis of Compound 310

[0237]

[0238] According to the preparation method of Synthesis Example 1, a-30 was replaced with an equal molar amount of a-310, and b-30 was replaced with an equal molar amount of b-310 to obtain compound 310 (14.52 g). The solid purity was ≥99.94% as determined by HPLC. Mass spectrum m / z: 1021.4383 (theoretical value: 1021.4396). Theoretical element content (%): C 77 H 55 N3: C, 90.47; H, 5.42; N, 4.11. Measured element content (%): C, 90.49; H, 5.44; N, 4.15.

[0239] [Synthesis Example 9] Synthesis of Compound 315

[0240]

[0241] According to the preparation method of Synthesis Example 1, e-30 was replaced with an equal molar amount of e-315, A-30 was replaced with an equal molar amount of B-30, and B-30 was replaced with an equal molar amount of A-249 to obtain compound 315 (15.68 g, 69%). The solid purity was ≥99.98% as determined by HPLC. Mass spectrum m / z: 1135.4851 (theoretical value: 1135.4865). Theoretical element content (%): C 86 H 61 N3: C, 90.89; H, 5.41; N, 3.70. Measured element content (%): C, 90.86; H, 5.47; N, 3.73.

[0242] [Synthesis Example 10] Synthesis of Compound 402

[0243]

[0244] According to the preparation method of Synthesis Example 1, C-30 was replaced with an equal molar amount of a-184, D-30 was replaced with an equal molar amount of D-402, and A-30 was replaced with an equal molar amount of B-30 to obtain Compound 402 (21.67 g). The purity of the solid was ≥99.96% as determined by HPLC. Mass spectrum m / z: 1615.6725 (theoretical value: 1615.6743). Theoretical element content (%): C 124 H 85 N3: C, 92.10; H, 5.30; N, 2.60. Measured element content (%): C, 92.15; H, 5.33; N, 2.64.

[0245] [Synthesis Example 11] Synthesis of Compound 458

[0246]

[0247] According to the preparation method of Synthesis Example 1, a-30 was replaced with an equal molar amount of a-458, and b-30 was replaced with an equal molar amount of d-30 to obtain compound 458 (13.31 g). The solid purity was ≥99.97% as determined by HPLC. Mass spectrum m / z: 923.4252 (theoretical value: 923.4239). Theoretical element content (%): C 69 H 53 N3: C, 89.67; H, 5.78; N, 4.55. Measured element content (%): C, 89.69; H, 5.74; N, 4.51.

[0248] [Synthesis Example 12] Synthesis of Compound 519

[0249]

[0250] According to the preparation method of Synthesis Example 1, C-30 was replaced with an equal molar amount of C-519, and A-30 was replaced with an equal molar amount of B-30 to obtain Compound 519 (17.48 g). The solid purity was ≥99.96% as determined by HPLC. Mass spectrum m / z: 1247.6128 (theoretical value: 1247.6117). Theoretical element content (%): C 94 H 77 N3: C, 90.42; H, 6.22; N, 3.37. Measured element content (%): C, 90.45; H, 6.23; N, 3.35.

[0251] [Synthesis Example 13] Synthesis of Compound 534

[0252]

[0253] According to the preparation method of Synthesis Example 1, a-30 was replaced with an equal molar amount of a-534, and b-30 was replaced with an equal molar amount of b-534 to obtain compound 534 (17.73 g). The solid purity was ≥99.97% as determined by HPLC. Mass spectrum m / z: 1247.6110 (theoretical value: 1247.6117). Theoretical element content (%): C 94 H 77 N3: C, 90.42; H, 6.22; N, 3.37. Measured element content (%): C, 90.41; H, 6.26; N, 3.39.

[0254] [Synthesis Example 14] Synthesis of Compound 548

[0255]

[0256] According to the preparation method of Synthesis Example 1, a-30 was replaced with an equal molar amount of a-216, b-30 was replaced with an equal molar amount of b-548, and c-30 was replaced with an equal molar amount of c-548 to obtain compound 548 (14.52 g). The solid purity was ≥99.96% as determined by HPLC. Mass spectrum m / z: 1007.4069 (theoretical value: 1007.4051). Theoretical element content (%): C 73 H 51 F2N3: C, 86.96; H, 5.10; N, 4.17. Measured element content (%): C, 86.99; H, 5.12; N, 4.19.

[0257] [Synthesis Example 15] Synthesis of Compound 564

[0258]

[0259] According to the preparation method of Synthesis Example 1, a-30 was replaced with an equal molar amount of a-564, and b-30 was replaced with an equal molar amount of d-30 to obtain compound 564 (13.23 g). The solid purity was ≥99.95% as determined by HPLC. Mass spectrum m / z: 905.4564 (theoretical value: 905.4554). Theoretical element content (%): C 67 H 39 D 10 N3: C, 88.80; H, 6.56; N, 4.64. Measured element content (%): C, 88.84; H, 6.52; N, 4.67.

[0260] [Synthesis Example 16] Synthesis of Compound 574

[0261]

[0262] According to the preparation method of Synthesis Example 1, a-30 was replaced with an equal molar amount of a-574, b-30 was replaced with an equal molar amount of d-30, and c-30 was replaced with an equal molar amount of c-574 to obtain compound 574 (12.87 g). The solid purity was ≥99.98% as determined by HPLC. Mass spectrum m / z: 905.4566 (theoretical value: 905.4554). Theoretical element content (%): C 67 H 39 D 10 N3: C, 88.80; H, 6.56; N, 4.64. Measured element content (%): C, 88.85; H, 6.55; N, 4.69.

[0263] [Synthesis Example 17] Synthesis of Compound 628

[0264]

[0265] According to the preparation method of Synthesis Example 1, a-30 was replaced with an equal molar amount of a-227, b-30 was replaced with an equal molar amount of b-628, and c-30 was replaced with an equal molar amount of a-227 to obtain compound 628 (19.07 g). The solid purity was ≥99.97% as determined by HPLC. Mass spectrum m / z: 1380.6130 (theoretical value: 1380.6118). Theoretical element content (%): C 105 H 68 D5N3: C, 91.27; H, 5.69; N, 3.04. Measured element content (%): C, 91.30; H, 5.67; N, 3.08.

[0266] [Synthesis Example 18] Synthesis of Compound 655

[0267]

[0268] According to the preparation method of Synthesis Example 1, a-30 was replaced with an equal molar amount of a-655, and b-30 was replaced with an equal molar amount of d-30 to obtain compound 655 (14.57 g). The solid purity was ≥99.96% as determined by HPLC. Mass spectrum m / z: 1039.4733 (theoretical value: 1039.4717). Theoretical element content (%): C 73 H 65 N3Si2: C, 84.27; H, 6.30; N, 4.04. Measured element content (%): C, 84.26; H, 6.35; N, 4.09.

[0269] [Synthesis Example 19] Synthesis of Compound 680

[0270]

[0271] According to the preparation method of Synthesis Example 1, a-30 was replaced with an equal molar amount of a-680, b-30 was replaced with an equal molar amount of d-30, and c-30 was replaced with an equal molar amount of c-680 to obtain compound 680 (14.97 g). The solid purity was ≥99.95% as determined by HPLC. Mass spectrum m / z: 1053.4860 (theoretical value: 1053.4874). Theoretical element content (%): C 74 H 67 N3Si2: C, 84.28; H, 6.40; N, 3.98. Measured element content (%): C, 84.26; H, 6.43; N, 3.95.

[0272] [Synthesis Example 20] Synthesis of Compound 704

[0273]

[0274] According to the preparation method of Synthesis Example 1, a-30 was replaced with an equal molar amount of a-704, b-30 was replaced with an equal molar amount of d-30, and c-30 was replaced with an equal molar amount of c-704 to obtain compound 704 (14.65 g). The purity of the solid was ≥99.98% as determined by HPLC. Mass spectrum m / z: 1045.4384 (theoretical value: 1045.4396). Theoretical element content (%): C 79 H 55 N3: C, 90.69; H, 5.30; N, 4.02. Measured element content (%): C, 90.66; H, 5.34; N, 4.08.

[0275] [Synthesis Example 21] Synthesis of Compound 807

[0276]

[0277] According to the preparation method of Synthesis Example 1, C-30 was replaced with an equal molar amount of C-807, E-30 was replaced with an equal molar amount of E-807, and A-30 was replaced with an equal molar amount of B-30 to obtain Compound 807 (15.32 g). The purity of the solid was ≥99.97% as determined by HPLC. Mass spectrum m / z: 1109.3968 (theoretical value: 1109.3957). Theoretical element content (%): C 80 H 50 F3N3: C, 86.54; H, 4.54; N, 3.78. Measured element content (%): C, 86.56; H, 4.55; N, 3.74.

[0278] [Synthesis Example 22] Synthesis of Compound 969

[0279]

[0280] According to the preparation method of Synthesis Example 1, a-30 was replaced with an equal molar amount of a-969, b-30 was replaced with an equal molar amount of d-30, and B-30 was replaced with an equal molar amount of B-574 to obtain compound 969 (14.43 g). The solid purity was ≥99.96% as determined by HPLC. Mass spectrum m / z: 1015.5639 (theoretical value: 1015.5650). Theoretical element content (%): C 75 H 53 D 10 N3: C, 88.63; H, 7.24; N, 4.13. Measured element content (%): C, 88.65; H, 7.26; N, 4.15.

[0281] [Synthesis Example 23] Synthesis of Compound 1040

[0282]

[0283] Synthetic intermediate A-1040

[0284] Under nitrogen, a-1040 (26.82 g, 80.00 mmol), b-1040 (21.71 g, 80.00 mmol), and sodium tert-butoxide (11.53 g, 120.00 mmol) dissolved in 500 ml of toluene were added to a reaction flask. Pd(dppf)Cl2 (0.59 g, 0.80 mmol) was added with stirring, and the mixture was heated under reflux for 4 h. After the reaction, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallization from ethyl acetate gave intermediate A-1040 (35.75 g, 85% yield); HPLC purity ≥99.79%. Mass spectrum: m / z: 525.2466 (theoretical value: 525.2457).

[0285] Synthesis of compound 1040

[0286] Under nitrogen protection, e-1040 (10.86 g, 20.00 mmol), A-1040 (31.54 g, 60.00 mmol), and sodium tert-butoxide (5.77 g, 60.00 mmol) were added to a reaction flask and dissolved in 250 ml of toluene. Pd2(dba)3 (0.55 g, 0.60 mmol) and X-Phos (0.29 g, 0.60 mmol) were added with stirring, and the mixed solution of the above reactants was heated under reflux for 8 h. After the reaction was completed, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallization from toluene gave compound 1040 (24.78 g). HPLC analysis showed that the solid purity was ≥99.92%. Mass spectrum m / z: 1875.8321 (theoretical value: 1875.8309). Theoretical element content (%): C 144 H 105 N3: C, 92.12; H, 5.64; N, 2.24. Measured element content (%): C, 92.14; H, 5.65; N, 2.26.

[0287] [Synthesis Example 24] Synthesis of Compound 1128

[0288]

[0289] According to the preparation method of Synthesis Example 1, a-30 was replaced with an equal molar amount of a-1128, and b-30 was replaced with an equal molar amount of b-1128 to obtain compound 1128 (15.44 g). The solid purity was ≥99.95% as determined by HPLC. Mass spectrum m / z: 1071.4568 (theoretical value: 1071.4552). Theoretical element content (%): C 81 H 57 N3: C, 90.72; H, 5.36; N, 3.92. Measured element content (%): C, 90.74; H, 5.38; N, 3.96.

[0290] [Synthesis Example 25] Synthesis of Compound 1138

[0291]

[0292] According to the preparation method of Synthesis Example 1, a-30 was replaced with an equal molar amount of a-1138, b-30 was replaced with an equal molar amount of d-30, and c-30 was replaced with an equal molar amount of c-1138 to obtain compound 1138 (15.83 g). The solid purity was ≥99.94% as determined by HPLC. Mass spectrum m / z: 1129.4369 (theoretical value: 1129.4356). Theoretical element content (%): C 81 H 55N5O2: C, 86.07; H, 4.90; N, 6.20. Measured element content (%): C, 86.05; H, 4.94; N, 6.25.

[0293] [Synthesis Example 26] Synthesis of Compound 1199

[0294]

[0295] Synthetic intermediate e-1199

[0296] Under nitrogen, intermediate f-1199 (20.83 g, 80.00 mmol), g-1199 (19.53 g, 80.00 mmol), tetrakistriphenylphosphine palladium (1.39 g, 1.20 mmol), potassium acetate (15.70 g, 160.00 mmol), and 800 mL of a 4:1:1 toluene / ethanol / water mixture were added sequentially to a reaction flask. The mixture was stirred and heated under reflux for 7 hours. After completion of the reaction, the mixture was cooled to room temperature and filtered to obtain a filter cake, which was rinsed with ethanol and recrystallized from toluene to obtain intermediate e-1199 (19.76 g, 83% yield). HPLC analysis of the solid revealed a purity of ≥99.82%. Mass spectrum: m / z: 295.9915 (theoretical value: 295.9926).

[0297] According to the preparation method of Synthesis Example 23, e-1040 was replaced with an equal molar amount of e-1199, and A-1040 was replaced with an equal molar amount of A-1138 to obtain Compound 1199 (19.55 g). The solid purity was ≥99.98% as determined by HPLC. Mass spectrum m / z: 1415.6134 (theoretical value: 1415.6117). Theoretical element content (%): C 108 H 77 N3: C, 91.56; H, 5.48; N, 2.97. Measured element content (%): C, 91.55; H, 5.49; N, 2.94.

[0298] [Synthesis Example 27] Synthesis of Compound 1243

[0299]

[0300] According to the preparation method of Synthesis Example 1, a-30 was replaced with an equal molar amount of a-1243, and b-30 was replaced with an equal molar amount of d-30 to obtain compound 1243 (13.16 g). The solid purity was ≥99.97% as determined by HPLC. Mass spectrum m / z: 900.4250 (theoretical value: 900.4240). Theoretical element content (%): C 67 H 44D5N3: C, 89.30; H, 6.04; N, 4.66. Measured element content (%): C, 89.34; H, 6.03; N, 4.69.

[0301] [Synthesis Example 28] Synthesis of Compound 1281

[0302]

[0303] According to the preparation method of Synthesis Example 1, a-30 was replaced with an equal molar amount of a-1281, b-30 was replaced with an equal molar amount of b-1281, and e-30 was replaced with an equal molar amount of e-1281 to obtain compound 1281 (12.60 g). The solid purity was ≥99.97% as determined by HPLC. Mass spectrum m / z: 874.4055 (theoretical value: 874.4035). Theoretical element content (%): C 64 H 50 N4: C, 87.84; H, 5.76; N, 6.40. Measured element content (%): C, 87.80; H, 5.75; N, 6.41.

[0304] [Synthesis Example 29] Synthesis of Compound 1309

[0305]

[0306] According to the preparation method of Synthesis Example 1, a-30 was replaced with an equal molar amount of a-1309, and b-30 was replaced with an equal molar amount of b-1309 to obtain Compound 1309 (15.72 g). The solid purity was ≥99.96% as determined by HPLC. Mass spectrum m / z: 1121.5119 (theoretical value: 1121.5104). Theoretical element content (%): C 82 H 67 N3Si: C, 87.74; H, 6.02; N, 3.74. Measured element content (%): C, 87.76; H, 6.03; N, 3.77.

[0307] [Synthesis Example 30] Synthesis of Compound 1343

[0308]

[0309] According to the preparation method of Synthesis Example 1, a-30 was replaced with an equal molar amount of a-1343, b-30 was replaced with an equal molar amount of d-30, and c-30 was replaced with an equal molar amount of c-1343 to obtain compound 1343 (14.06 g). The solid purity was ≥99.95% as determined by HPLC. Mass spectrum m / z: 989.4361 (theoretical value: 989.4345). Theoretical element content (%): C 73 H 55N3O: C, 88.54; H, 5.60; N, 4.24. Measured element content (%): C, 88.55; H, 5.63; N, 4.27.

[0310] [Synthesis Example 31] Synthesis of Compound 1377

[0311]

[0312] According to the preparation method of Synthesis Example 1, a-30 was replaced with an equal molar amount of a-1377, and b-30 was replaced with an equal molar amount of b-1377 to obtain compound 1377 (14.32 g). The solid purity was ≥99.96% as determined by HPLC. Mass spectrum m / z: 993.3380 (theoretical value: 993.3365). Theoretical element content (%): C 68 H 46 F3N3S: C, 82.15; H, 4.66; N, 4.23. Measured element content (%): C, 82.18; H, 4.62; N, 4.25.

[0313] [Synthesis Example 32] Synthesis of Compound 1409

[0314]

[0315] According to the preparation method of Synthesis Example 1, a-30 was replaced with an equal molar amount of a-216, and b-30 was replaced with an equal molar amount of b-1409 to obtain compound 1409 (16.11 g). The solid purity was ≥99.97% as determined by HPLC. Mass spectrum m / z: 1133.4721 (theoretical value: 1133.4709). Theoretical element content (%): C 86 H 59 N3: C, 91.05; H, 5.24; N, 3.70. Measured element content (%): C, 91.08; H, 5.26; N, 3.73.

[0316] [Synthesis Example 33] Synthesis of Compound 1424

[0317]

[0318] According to the preparation method of Synthesis Example 1, a-30 was replaced with an equal molar amount of a-1424, b-30 was replaced with an equal molar amount of d-30, and c-30 was replaced with an equal molar amount of c-1424 to obtain compound 1424 (13.17 g). The solid purity was ≥99.94% as determined by HPLC. Mass spectrum m / z: 953.4441 (theoretical value: 953.4457). Theoretical element content (%): C 69 H 55N5: C, 86.85; H, 5.81; N, 7.34. Measured element content (%): C, 86.87; H, 5.83; N, 7.35.

[0319] [Synthesis Example 34] Synthesis of Compound 1428

[0320]

[0321] According to the preparation method of Synthesis Example 1, a-30 was replaced with an equal molar amount of a-227, b-30 was replaced with an equal molar amount of d-30, e-30 was replaced with an equal molar amount of e-1428, and B-30 was replaced with an equal molar amount of B-704 to obtain compound 1428 (14.57 g). The purity of the solid was ≥99.96% as determined by HPLC. Mass spectrum m / z: 1039.4851 (theoretical value: 1039.4865). Theoretical element content (%): C 78 H 61 N3: C, 90.05; H, 5.91; N, 4.04. Measured element content (%): C, 90.09; H, 5.94; N, 4.03.

[0322] [Synthesis Example 35] Synthesis of Compound 1432

[0323]

[0324] According to the preparation method of Synthesis Example 1, a-30 was replaced with an equal molar amount of a-1432, b-30 was replaced with an equal molar amount of d-30, c-30 was replaced with an equal molar amount of c-1432, and e-30 was replaced with an equal molar amount of e-1432 to obtain compound 1432 (13.01 g). The solid purity was ≥99.98% as determined by HPLC. Mass spectrum m / z: 915.4564 (theoretical value: 915.4552). Theoretical element content (%): C 68 H 57 N3: C, 89.14; H, 6.27; N, 4.59. Measured element content (%): C, 89.17; H, 6.29; N, 4.53.

[0325] [Device Example]

[0326] A combined IVL test system, comprised of test software, a computer, a Keithley K2400 digital source meter, and a PhotoResearch PR788 spectrum scanning luminance meter, was used to test the luminous efficiency of organic electroluminescent devices. Lifespan tests were conducted using a McScience M6000 OLED Lifespan Test System.

[0327] [Example 1]

[0328] The glass substrate was cleaned with distilled water and ultrasonic waves. After the distilled water washing, ultrasonic washing was performed using solvents such as isopropyl alcohol, acetone, and methanol, and then dried. After drying, the substrate was transferred to a plasma cleaning machine. After washing, the substrate was transferred to an evaporation machine. Indium tin oxide (ITO) was coated on the glass substrate to form an anode. HI-1 was evaporated on the anode to form a thickness of The hole injection layer is formed by vapor deposition of the compound 30 of the present invention on the hole injection layer to form a hole injection layer having a thickness of The hole transport layer is deposited on the hole transport layer. The light-emitting layer is formed with RH-1 as the main material of the light-emitting layer and doped with 3wt% of RD-1 to form a hole transport layer with a thickness of ET-1:LiQ (mass ratio 1:1) was evaporated on the luminescent layer to form a film with a thickness of LiF is evaporated on the electron transport layer to form an electron transport layer with a thickness of Al is evaporated on the electron injection layer to form a layer with a thickness of Thus, an organic light-emitting device is formed.

[0329]

[0330] [Examples 2 to 35]

[0331] Organic electroluminescent devices were prepared by the same preparation method as in Example 1, except that the compounds 116, 184, 216, 227, 249, 308, 310, 315, 402, 458, 519, 534, 548, 564, 574, 628, 655, 680, 704, 807, 969, 1040, 1128, 1138, 1199, 1243, 1281, 1309, 1343, 1377, 1409, 1424, 1428 and 1432 of the present invention were used instead of the compound 30 in Example 1 as hole transport layer materials.

[0332] [Comparative Examples 1-2]

[0333] An organic electroluminescent device was prepared by the same preparation method as in Example 1 except that Compound P-1 and Compound P-2 were used instead of Compound 30 in Example 1 as hole transport layer materials.

[0334] The test environment is atmospheric environment and the temperature is room temperature. The test results of the luminescence characteristics of the organic electroluminescent devices obtained in the embodiments 1 to 35 of the present invention and the comparative examples 1 to 2 are shown in Table 1 below.

[0335] Table 1:

[0336]

[0337]

[0338] The results in Table 1 show that when the aromatic amine compound of the present invention is applied to the hole transport layer of an organic electroluminescent device, the device has higher luminous efficiency and longer service life than the comparative compounds P-1 to P-2. The aromatic amine compound of the present invention is a hole transport layer material with good performance.

[0339] [Example 36]

[0340] The glass substrate was cleaned with distilled water and ultrasonic waves. After the distilled water washing, ultrasonic washing was performed using solvents such as isopropyl alcohol, acetone, and methanol, and then dried. After drying, the substrate was transferred to a plasma cleaning machine. After washing, the substrate was transferred to an evaporation machine. Indium tin oxide (ITO) was coated on the glass substrate to form an anode. HI-2 was evaporated on the anode to form a thickness of HT-2 was evaporated on the hole injection layer to form a hole injection layer with a thickness of The first hole transport layer. The compound 30 of the present invention is evaporated on the first hole transport layer to form a layer with a thickness of The second hole transport layer is deposited on the second hole transport layer. The light-emitting layer is formed with GH-2 as the main material of the light-emitting layer and doped with 7wt% of GD-2 to form a thickness of ET-1:LiQ (mass ratio 1:1) was evaporated on the luminescent layer to form a film with a thickness of LiF is evaporated on the electron transport layer to form an electron transport layer with a thickness of Al is evaporated on the electron injection layer to form a layer with a thickness of cathode.

[0341] Thus, an organic light-emitting device is formed.

[0342]

[0343] [Examples 37 to 70]

[0344] The compounds 116, 184, 216, 227, 249, 308, 310, 315, 402, 458, 519, 534, 548, 564, 574, 628, 655, 680, 704, 807, 969, 1040, 1128, 1138, 1199, 1243, 1281, 1309, 1343, 1377, 1409, 1424, 1428 and 1432 of the present invention were used to replace the compound 30 in Example 36 as the second hole transport layer material. Except for this, an organic electroluminescent device was prepared by the same preparation method as in Example 36.

[0345] [Comparative Examples 3-4]

[0346] An organic electroluminescent device was prepared by the same preparation method as in Example 36, except that Compound P-3 and Compound P-4 were used to replace Compound 30 in Example 36 as the second hole transport layer material.

[0347] The test environment is atmospheric environment and the temperature is room temperature. The test results of the luminescence characteristics of the organic electroluminescent devices obtained in the embodiments of the present invention 36-70 and comparative examples 3-4 are shown in Table 2 below.

[0348] Table 2:

[0349]

[0350]

[0351] The results in Table 2 show that when the aromatic amine compound of the present invention is applied to the second hole transport layer of an organic electroluminescent device, the device has higher luminous efficiency and longer service life than the comparative compounds P-3 to P-4. The compound of the present invention is a second hole transport layer material with good performance.

[0352] [Example 71]

[0353] The glass substrate was cleaned with distilled water and ultrasonic waves. After the distilled water washing, ultrasonic washing was performed using solvents such as isopropyl alcohol, acetone, and methanol, and then dried. After drying, the substrate was transferred to a plasma cleaning machine. After washing, the substrate was transferred to a vapor deposition machine. ITO / Ag / ITO was coated on the glass substrate to form an anode. HI-3 was evaporated on the anode to form a thickness of HT-3 was evaporated on the hole injection layer to form a hole injection layer with a thickness of The hole transport layer is deposited on the hole transport layer. The light-emitting layer is formed with BH-3 as the main material of the light-emitting layer and 4wt% of BD-3 doped to form a hole transport layer with a thickness of ET-3:LiQ (mass ratio 1:1) was evaporated on the luminescent layer to form a thickness of LiF is evaporated on the electron transport layer to form an electron transport layer with a thickness of The electron injection layer is formed by evaporating Mg:Ag (mass ratio 1:9) on the electron injection layer to form a layer with a thickness of The cathode layer is deposited with the compound 30 of the present invention to form a layer with a thickness of Thus, an organic light-emitting device is formed.

[0354]

[0355] [Examples 72 to 90]

[0356] Compound 184, compound 216, compound 249, compound 308, compound 310, compound 315, compound 519, compound 548, compound 564, compound 574, compound 628, compound 680, compound 704, compound 969, compound 1128, compound 1138, compound 1243, compound 1281, and compound 1409 of the present invention were used to replace compound 30 in Example 71 as covering layer materials. Except for this, an organic electroluminescent device was prepared by the same preparation method as in Example 71.

[0357] [Comparative Example 5]

[0358] An organic electroluminescent device was prepared by the same preparation method as in Device Example 71, except that Compound P-5 was used instead of Compound 30 in Device Example 71 as the covering layer material.

[0359] The test environment is atmospheric environment and the temperature is room temperature. The test results of the luminescence characteristics of devices 71 to 90 in the embodiments of the present invention and the organic electroluminescent devices obtained in comparative example 5 are shown in Table 3 below.

[0360] Table 3:

[0361]

[0362]

[0363] The results in Table 3 show that when the aromatic amine compound of the present invention is applied to the covering layer of an organic electroluminescent device, the device has higher luminous efficiency and longer service life than the comparative compound P-5. The compound of the present invention is a covering layer material with good performance.

[0364] It should be noted that the present invention is particularly described using individual embodiments. However, without departing from the principles of the present invention, a person skilled in the art may make various improvements in form or detail to the present invention, and these improvements also fall within the scope of protection of the present invention.

Claims

1. An aromatic amine compound, characterized in that The aromatic amine compound has a structure represented by Formula I: Wherein, R1, R2, and R3 are independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 Any one of an alicyclic ring and a fused ring of a C6-C30 aromatic ring; and at least one of R1, R2, and R3 is selected from any one of a halogen, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C3-C30 alicyclic ring and a fused ring of a C6-C30 aromatic ring; Ar1, Ar2, Ar3, Ar4, Ar5, Ar6 are independently selected from Formula II or any one of the following groups; and at least one of Ar1, Ar2, Ar3, Ar4, Ar5, Ar6 is selected from Formula II; Said X1 is selected from C(R i R j ) Said X2 is selected from O, S, N (R s ) The v is independently selected from any one of CH and N; The ring A is selected from a substituted or unsubstituted C3-C10 alicyclic ring; The R i Any one independently selected from a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C3-C30 alicyclic group, and a fused cyclic group of a C6-C30 aromatic ring; The R j 、R a 、R b 、R b ' is independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring, or R i 、R j are connected to form a substituted or unsubstituted ring; wherein R b The substituent in "substituted or unsubstituted" is selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, silyl, C1-C25 alkyl, C3-C9 cycloalkyl, C1-C25 heterocycloalkyl, C6-C30 aryl, C2-C30 heteroaryl, or a combination thereof; The R s Any one independently selected from hydrogen, deuterium, tritium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; The R i '、R j 'Independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl; The a1 is selected from 0, 1, 2, 3 or 4; when there are two or more R a When two or more R a The same or different from each other, or two adjacent R a are connected to each other to form a substituted or unsubstituted ring; b1 is selected from 0, 1, 2, 3, 4 or 5; b2 is selected from 0, 1, 2, 3 or 4; b3 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; b4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; b5 is selected from 0, 1 or 2; b6 is selected from 0, 1, 2 or 3; when there are two or more R b When two or more R b The same or different from each other, or two adjacent R b are connected to each other to form a substituted or unsubstituted ring; The b'1 is selected from 0, 1 or 2; when there are two or more R b ', two or more R b 'same or different from each other; The L1, L2, L3, L4, L5, and L6 are independently selected from a single bond or any one of the following groups or a combination of two or more of the following groups: Said X3 is selected from O, S, N (R t ) The z is independently selected from any one of CH and N; The ring B is selected from a substituted or unsubstituted C3-C10 alicyclic ring; The R c 、R c '、R p 、R q independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or R p 、R q are connected to form a substituted or unsubstituted ring; The R t Any one independently selected from hydrogen, deuterium, tritium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; Said q is selected from 1, 2, 3 or 4; Said c1 is selected from 0, 1, 2, 3 or 4; said c2 is selected from 0, 1, 2, 3, 4, 5 or 6; said c3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said c4 is selected from 0, 1 or 2; when there are two or more R c When two or more R c The same or different from each other, or two adjacent R c are connected to each other to form a substituted or unsubstituted ring; The c'1 is selected from 0, 1 or 2; when there are two or more R c ', two or more R c ' are the same as or different from each other.

2. An aromatic amine compound according to claim 1, characterized in that The formula I is selected from any one of the following structures: Ar1, Ar2, Ar3, Ar4, Ar5, Ar6, L1, L2, L3, L4, L5, L6, R1, R2, R3, R a The definitions of X1, a1 are the same as those in Formula I.

3. An aromatic amine compound according to claim 1, characterized in that The formula II is selected from any one of the following groups: The R i independently selected from the following substituted or unsubstituted groups: benzocyclopropanyl, naphthocyclopropanyl, benzocyclobutanyl, naphthocyclobutanyl, benzocyclopentanyl, naphthocyclopentanyl, benzocyclohexanyl, naphthocyclohexanyl, benzocycloheptanyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, perylenyl, pyridyl, pyrimidinyl, pyrazinyl , pyridazinyl, triazinyl, furanyl, thienyl, pyrrolyl, oxazolyl, benzoxazolyl, dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzimidazolyl, dibenzimidazolyl, quinolyl, benzoquinolyl, isoquinolyl, benzoisoquinolyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenanthrolinyl, naphthyridinyl, indolyl, acridinyl, phenoxazinyl, phenothiazinyl; The R j 、R a 、R a independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropanyl, naphthocyclopropanyl, benzocyclobutanyl, naphthocyclobutanyl, benzocyclopentanyl, naphthocyclopentanyl , benzocyclohexyl, naphthiocyclohexyl, benzocycloheptyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, perylenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thienyl, pyrrolyl, oxazolyl, benzoxazolyl, dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzimidazolyl, dibenzimidazolyl, quinolyl, benzoquinolyl, isoquinolyl, benzoisoquinolyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenanthrolinyl, naphthyridinyl, indolyl, acridinyl, phenoxazinyl, phenothiazinyl; The R v independently selected from hydrogen, deuterium, tritium, substituted or unsubstituted methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl , vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropanyl, naphthocyclopropanyl, benzocyclobutanyl, naphthocyclobutanyl, benzocyclopentanyl, naphthocyclopentanyl, benzocyclohexanyl, naphthocyclohexanyl, benzocycloheptanyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, perylenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl; The a1 is selected from 0, 1, 2, 3 or 4; the a2 is selected from 0, 1, 2 or 3; when there are two or more R a When two or more R a The same or different from each other, or two adjacent R a They are connected to each other to form substituted or unsubstituted: benzene ring, naphthalene ring, pyridine ring, pyrimidine ring, cyclopentane ring, cyclohexane ring; a'1 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; a'2 is selected from 0, 1, 2, 3, 4, 5 or 6; a'3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; a'4 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 ', two or more R a ' are the same as or different from each other.

4. An aromatic amine compound according to claim 1, characterized in that, When Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 are not of formula II, they are independently selected from any one of the following groups; The R b 、R b independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropanyl, naphthocyclopropanyl, benzocyclobutanyl, naphthocyclobutanyl, benzocyclopentanyl, naphthocyclopentanyl , benzocyclohexyl, naphthiocyclohexyl, benzocycloheptyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, perylenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thienyl, pyrrolyl, oxazolyl, benzoxazolyl, dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzimidazolyl, dibenzimidazolyl, quinolyl, benzoquinolyl, isoquinolyl, benzoisoquinolyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenanthrolinyl, naphthyridinyl, indolyl, acridinyl, phenoxazinyl, phenothiazinyl; wherein R b The substituents in "substituted or unsubstituted" are selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidine any one of 1,2-diphenylmethane, ... The R s independently selected from hydrogen, deuterium, tritium, substituted or unsubstituted methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl , vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropanyl, naphthocyclopropanyl, benzocyclobutanyl, naphthocyclobutanyl, benzocyclopentanyl, naphthocyclopentanyl, benzocyclohexanyl, naphthocyclohexanyl, benzocycloheptanyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, perylenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl; The R i '、R j 'Independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl any one; b1 is selected from 0, 1, 2, 3, 4 or 5; b2 is selected from 0, 1, 2, 3 or 4; b3 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; b4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; b5 is selected from 0, 1 or 2; b6 is selected from 0, 1, 2 or 3; b7 is selected from 0 or 1; when there are two or more R b When two or more R b The same or different from each other, or two adjacent R b They are connected to each other to form substituted or unsubstituted: benzene ring, naphthalene ring, pyridine ring, pyrimidine ring, cyclopentane ring, cyclohexane ring; The b'1 is selected from 0, 1 or 2; when there are two or more R b ', two or more R b ' are the same as or different from each other.

5. An aromatic amine compound according to claim 1, characterized in that, The L1, L2, L3, L4, L5, and L6 are independently selected from a single bond or any one of the following groups or a combination of two or more of the following groups: The R c 、R c '、R p 、R q independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropanyl, naphthocyclopropanyl, benzocyclobutanyl, naphthocyclobutanyl, benzocyclopentanyl, naphthocyclopentanyl , benzocyclohexyl, naphthiocyclohexyl, benzocycloheptyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, perylenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thienyl, pyrrolyl, oxazolyl, benzoxazolyl, dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzimidazolyl, dibenzimidazolyl, quinolyl, benzoquinolyl, isoquinolyl, benzoisoquinolyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenanthrolinyl, naphthyridinyl, indolyl, acridinyl, phenoxazinyl, phenothiazinyl; The R t independently selected from hydrogen, deuterium, tritium, substituted or unsubstituted methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl , vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropanyl, naphthocyclopropanyl, benzocyclobutanyl, naphthocyclobutanyl, benzocyclopentanyl, naphthocyclopentanyl, benzocyclohexanyl, naphthocyclohexanyl, benzocycloheptanyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, perylenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl; Said c1 is selected from 0, 1, 2, 3 or 4; said c2 is selected from 0, 1, 2, 3, 4, 5 or 6; said c3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said c4 is selected from 0, 1 or 2; said c5 is selected from 0, 1, 2 or 3; said c6 is selected from 0 or 1; when there are two or more R c When two or more R c The same or different from each other, or two adjacent R c They are connected to each other to form substituted or unsubstituted: benzene ring, naphthalene ring, pyridine ring, pyrimidine ring, cyclopentane ring, cyclohexane ring; The c'1 is selected from 0, 1 or 2; the c'2 is selected from 0, 1, 2, 3 or 4; the c'3 is selected from 0, 1, 2, 3, 4, 5 or 6; the c'4 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the c'5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; the c'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 c ', two or more R c ' are the same as or different from each other.

6. An aromatic amine compound according to claim 1, characterized in that, Said R1, R2, R3 are independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropanyl, naphthoxycyclopropanyl, benzocyclobutanyl, naphthoxycyclobutanyl, benzocyclopentanyl, alkyl, naphthocyclopentanyl, benzocyclohexanyl, naphthocyclohexanyl, benzocycloheptanyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, perylenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thienyl, pyrrolyl, oxazolyl, benzoxazolyl, dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzimidazolyl, dibenzimidazolyl, quinolinyl, benzoquinolinyl, isoquinolinyl, benzoisoquinolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenanthrolinyl, naphthyridinyl, indolyl, acridinyl, phenoxazinyl, phenothiazinyl any one of the oxazine groups; and at least one of R1, R2, and R3 is selected from halogen, cyano, substituted or unsubstituted groups: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclohexenyl, naphthocyclohexenyl, benzocycloheptyl, benzocyclobutenyl, benzocyclobutenyl, benzocyclohexenyl, benzocyclohepten ... any one of benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, perylenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furyl, benzofuranyl, dibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, pyrrolyl, indolyl, oxazolyl, benzoxazolyl, dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzimidazolyl, dibenzimidazolyl, quinolyl, benzoquinolyl, isoquinolyl, benzoisoquinolyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenanthrolinyl, naphthyridinyl, indolyl, acridinyl, phenoxazinyl, and phenothiazinyl.

7. An aromatic amine compound according to claim 1, characterized in that, The formula I is selected from any one of the following structures:

8. An organic electroluminescent device comprising an anode, a cathode, and an organic layer located between the anode and the cathode or on a side of the cathode facing away from the anode, wherein: The organic layer contains at least one of the aromatic amine compounds according to any one of claims 1 to 7.

9. The organic electroluminescent device according to claim 8, wherein the organic layer is located between the anode and the cathode or on a side of the cathode facing away from the anode, The organic layer comprises at least one of a hole transport layer and a covering layer, and the at least one of the hole transport layer and the covering layer comprises at least one of the aromatic amine compounds according to any one of claims 1 to 7.

10. The organic electroluminescent device according to claim 8, wherein the organic layer is located between the anode and the cathode, The organic layer includes a first light-emitting portion, a second light-emitting portion and a charge generation layer, the first light-emitting portion is located between the anode and the cathode, the second light-emitting portion is located between the first light-emitting portion and the cathode, the charge generation layer is located between the first light-emitting portion and the second light-emitting portion, and the charge generation layer includes at least one of the aromatic amine compounds described in any one of claims 1 to 7.