Arylamine compound and organic electroluminescent device thereof

Abstract

The invention provides an arylamine compound and an organic electroluminescent device thereof, and particularly relates to the technical field of organic electroluminescent materials. The arylamine compound provided by the invention has high hole mobility and good thermal stability, and when the arylamine compound is applied to a hole transport region in an organic electroluminescent device, hole and electron transport rates can be effectively balanced, the recombination probability of excitons in a luminescent layer is improved, and maximum recombination of current carriers is realized. Therefore, the luminous efficiency of the device is improved and the service life of the device is prolonged. Besides, the arylamine compound provided by the invention also has a relatively high refractive index, and when the arylamine compound is applied to a device as a covering layer, the light extraction efficiency can be effectively enhanced, so that the luminous efficiency of the device is improved, and the service life of the device is prolonged. The arylamine compound provided by the invention can be applied to various fields such as display, illumination, business, medicine and the like.

Description

Technical Field

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

[0002] Organic light-emitting diodes (OLEDs) are one of the most promising new display technologies. They have advantages such as light weight, small thickness, wide viewing angle, fast response speed, low energy consumption, high efficiency, wide adaptability, and good color purity. They are widely used in many fields such as lighting and display and have broad application prospects.

[0003] OLEDs consist of a cathode, an anode, and an organic layer. The organic layer includes a hole injection layer, a hole transport layer, an electron blocking layer, an emissive layer, and a capping layer. These organic functional layers play a crucial role in improving the driving voltage, luminous efficiency, color purity, and lifespan of OLED devices. The light-emitting principle of OLEDs involves holes and electrons being injected from the anode and cathode into the organic layer, respectively, under the influence of an external electric field. They then pass through the hole transport region and electron transport region, respectively, into the emissive layer. In the emissive layer, they recombine to generate excitons, releasing energy. These excitons migrate under the influence of the electric field, transferring energy to the luminescent material in the emissive layer. Electrons in the luminescent material molecules transition from the ground state to an excited state, and then back to the ground state. During this process, energy is released in the form of light.

[0004] Hole transport materials are crucial in organic light-emitting diodes (OLEDs). Their role is to increase the hole transport rate within the device, balance the hole and electron transport rates, trap electrons within the emissive layer, and increase the recombination probability of excitons within the emissive layer, thus maximizing carrier recombination. Good hole transport materials should possess excellent properties such as high hole mobility, good thermal stability, good film-forming properties, and appropriate HOMO energy levels. However, most currently used hole transport materials suffer from poor film-forming properties and thermal stability, as well as low hole mobility. These issues negatively impact the luminous efficiency and lifespan of the device. Furthermore, to further improve OLED device performance, placing a high-refractive-index capping layer outside the semi-transparent electrode effectively reduces total internal reflection and waveguide losses in the OLED device, couples out trapped light, enhances light extraction efficiency, and consequently improves luminous efficiency and extends device lifespan.

[0005] In response to the current industrial application requirements of OLED devices, and in order to better address the issues of low luminous efficiency and lifespan of organic light-emitting devices, it is urgent to design new hole transport layer materials or capping layer materials with superior performance. Summary of the Invention

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

[0007] This invention provides an aromatic amine compound, wherein the aromatic amine compound is selected from the structure represented by formula I:

[0008]

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

[0010] The Ar2 is selected from chemical formula III;

[0011]

[0012] The Ar3 is selected from any of the following structures:

[0013]

[0014] L1 is selected from any of the following structures:

[0015]

[0016] Z is selected from either CH or N, and at least one of them is selected from N;

[0017] The V is selected from either CH or N, and at least one of them is selected from N;

[0018] The Y is selected from O, S, C(R) m R n ), N(R e Any one of the following;

[0019] The Y' is selected from O, S, C(R) p R q ), N(R r Any one of the following;

[0020] L2 and L3 are independently selected from any one of the following: single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, and substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic rings.

[0021] The R is selected from any one of substituted or unsubstituted C1-C25 alkyl groups, substituted or unsubstituted C3-C25 alicyclic groups, and substituted or unsubstituted C1-C25 heterocyclic alkyl groups;

[0022] The R1, R2, R3, Ra, R m R n R p R q Independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 alicyclic, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl group, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl group, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl group, or R m R n The connections between them form substituted or unsubstituted rings, or R p R q The links between them form substituted or unsubstituted rings;

[0023] The R e R r It is independently selected from any one of the following: substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C3-C25 alicyclic groups, substituted or unsubstituted C1-C25 heterocyclic alkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl groups, substituted or unsubstituted C1-C25 heterocyclic alkanes and C6-C30 aromatic ring fused cycloyl groups, and substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl groups;

[0024] The n1 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; when there are two or more R1s, the two or more R1s are the same or different from each other, or two adjacent R1s are connected to each other to form a substituted or unsubstituted ring;

[0025] The n2 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; when there are two or more R2s, the two or more R2s are the same or different from each other, or two adjacent R2s are connected to each other to form a substituted or unsubstituted ring;

[0026] The n3 is selected from 0, 1, 2, 3, 4 or 5; the n4 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the n5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; the n6 is selected from 0, 1, 2, 3 or 4; the n7 is selected from 0, 1 or 2; the n8 is selected from 0, 1, 2, 3, 4, 5 or 6; the n9 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; when there are two or more R3s, the two or more R3s are the same as or different from each other, or two adjacent R3s are connected to each other to form a substituted or unsubstituted aromatic ring;

[0027] a1 is selected from 0, 1, 2, 3 or 4; a2 is selected from 0, 1, 2, 3, 4, 5 or 6; when there are two or more Ra, the two or more Ra are the same or different from each other, or two adjacent Ra are connected to each other to form a substituted or unsubstituted ring.

[0028] 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 opposite to the anode, the organic layer comprising at least one of the aromatic amine compounds described in the present invention.

[0029] Beneficial effects

[0030] This invention provides an aromatic amine compound and its organic electroluminescent device. The aromatic amine compound of this invention possesses high hole mobility, good thermal stability, and good film-forming properties. When applied to the hole transport region in an organic electroluminescent device, it can increase the hole transport rate in the device, balance the hole and electron transport rates, block electrons within the light-emitting layer, increase the recombination probability of excitons within the light-emitting layer, and achieve maximum carrier recombination. This improves the luminous efficiency of the device and extends its lifespan. Simultaneously, the aromatic amine compound of this invention also has a high refractive index. When applied to the capping layer in an organic electroluminescent device, it effectively reduces total internal reflection loss and waveguide loss in the OLED device, couples out light trapped in the device, enhances light extraction efficiency, and further improves the luminous efficiency and extends the device's lifespan. Detailed Implementation

[0031] The technical solutions of the embodiments of the present invention will be clearly and completely described below. Obviously, the described embodiments are only some embodiments of the present invention, and not all embodiments. After reading the present invention, any modifications of the present invention in various equivalent forms by those skilled in the art fall within the scope defined by the present invention.

[0032] In this instruction manual, This refers to the portion that is connected to another substituent. It can be attached to any optional position of the attached group / fragment.

[0033] In this specification, when a substituent or linking site lies within a bond that extends through two or more rings, it indicates that the substituent or linking site can be linked to any one of the two or more rings, specifically to any one of the corresponding optional sites within the ring. For example, Can represent Can represent And so on.

[0034] In this specification, when the position of a substituent or linking site on the ring is not fixed, it means that it can be linked to any of the optional sites on the ring.

[0035] For example, Can represent Can represent Can represent And so on.

[0036] Examples of halogens described in this invention may include fluorine, chlorine, bromine, and iodine.

[0037] The alkyl group referred to in this invention is a general term for monovalent groups obtained by removing one hydrogen atom from an alkane molecule. It can be a straight-chain alkyl group or a branched-chain alkyl group, preferably having 1 to 25 carbon atoms, more preferably 1 to 12 carbon atoms, and particularly preferably 1 to 6 carbon atoms. Specific examples may include methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl, isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, etc., but are not limited thereto.

[0038] The alicyclic group mentioned in this invention refers to the general term for monovalent groups obtained by removing one hydrogen atom from an alicyclic hydrocarbon molecule. These groups can be cycloalkyl, cycloalkenyl, etc., preferably having 3 to 25 carbon atoms, more preferably 3 to 20 carbon atoms, particularly preferably 3 to 15 carbon atoms, more preferably 5 to 10 carbon atoms, and most preferably 5 to 7 carbon atoms. Specific examples may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, etc., but are not limited thereto.

[0039] The aryl group mentioned in this invention refers to the general term for the monovalent group obtained by removing a hydrogen atom from the aromatic carbon atom of an aromatic compound molecule. It can be a monocyclic aryl, polycyclic aryl, or fused-ring aryl, preferably having 6 to 30 carbon atoms, more preferably 6 to 18 carbon atoms, particularly preferably 6 to 15 carbon atoms, and most preferably 6 to 12 carbon atoms. The monocyclic aryl group refers to an aryl group with only one aromatic ring in the molecule, such as phenyl, but not limited to this; the polycyclic aryl group refers to an aryl group with two or more independent aromatic rings in the molecule, and specific examples may include biphenyl, terphenyl, tetraphenyl, 1-phenylnaphthyl, 2-phenylnaphthyl, etc., but not limited to this; the fused-ring aryl group refers to an aryl group with two or more aromatic rings in the molecule that are fused together by sharing two adjacent carbon atoms, and specific examples may include naphthyl, anthraceneyl, phenanthryl, pyrene, peryl, fluorenyl, benzo[a]fluorenyl, triphenylene, fluoranyl, spirofluorenyl, spirodifluorenyl, etc., but not limited to this.

[0040] The heteroaryl group described in this invention refers to the general term for groups obtained by replacing one or more aromatic carbon atoms in an aryl group with heteroatoms. The heteroatoms include, but are not limited to, oxygen, sulfur, nitrogen, silicon, or phosphorus atoms, and preferably have 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 linking site of the heteroaryl group can be located on a cyclic carbon atom or on a cyclic heteroatom. The heteroaryl group can be a monocyclic heteroaryl, polycyclic heteroaryl, or fused-ring heteroaryl. Specific examples of the monocyclic heteroaryl group may include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thiopheneyl, pyrroleyl, oxazolyl, thiazolyl, imidazolyl, etc., but are not limited thereto; specific examples of the polycyclic heteroaryl group may include bipyridyl, bipyrimidinyl, phenylpyridinyl, phenylpyrimidinyl, etc., but are not limited thereto; specific examples of the fused-ring heteroaryl group may include quinolinyl, isoquinolinyl, benzo[a]quinolinyl, benzo[a]isoquinolinyl, quinazolinyl, quinoxalinyl, benzo[a]quinolinyl, etc. Zolpidemolinyl, benzoquinoxolinyl, o-phenantholinyl, naphridyl, indolyl, benzoxazolyl, benzoimidazolyl, benzothiazolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothiophenyl, benzodibenzothiophenyl, dibenzoxazolyl, dibenzoimidazolyl, dibenzothiazolyl, carbazoleyl, benzocarbazoleyl, acridineyl, 9,10-dihydroacridyl, phenoxazinyl, phenthiazinyl, phenoxazinyl, spirofluorenexanthraceneyl, spirofluorenethionthanthraceneyl, etc., but not limited to these.

[0041] The arylene group referred to in this invention refers to the general term for the divalent group obtained by removing two hydrogen atoms from the aromatic nucleus of an aromatic hydrocarbon molecule. It can be a monocyclic arylene, a polycyclic arylene, or a fused-ring arylene, preferably having 6 to 30 carbon atoms, more preferably 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 18 carbon atoms, and most preferably 6 to 12 carbon atoms. Specific examples may include phenylene, biphenylene, terphenylene, naphthylene, anthracene, phenanthrene, pyrene, trimethyleneene, perylene, fluorene, fluorenylene, phenylfluorene, etc., but are not limited thereto.

[0042] The heteroaryl group described in this invention refers to a divalent group in which at least one carbon atom of the aryl group is replaced by a heteroatom. The heteroatom is selected from O, S, N, Si, B, P, etc., but is not limited thereto. Preferably, it has 2 to 30 carbon atoms, more preferably 2 to 18 carbon atoms, particularly preferably 2 to 15 carbon atoms, and most preferably 2 to 12 carbon atoms. The heteroaryl group includes monocyclic heteroaryl, polycyclic heteroaryl, fused-ring heteroaryl, or combinations thereof. Examples of the heteroaryl group include, but are not limited to, the following groups: pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, quinazolinyl, naphthinyl, dibenzofuran, dibenzothiophene, etc., but are not limited thereto.

[0043] The fused alicyclic and aromatic rings described in this invention refer to the monovalent group formed by removing one hydrogen atom after the aromatic ring and the alicyclic ring are fused together. The aromatic ring preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and most preferably 6 to 14 carbon atoms. The alicyclic ring preferably has 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, and most preferably 3 to 7 carbon atoms. Examples include benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, naphthocyclopropane, naphthocyclobutane, naphthocyclopentane, naphthocyclohexane, naphthocyclopentenyl, naphthocyclohexenyl, etc., but are not limited thereto.

[0044] The fused cyclic group of alicyclic and heteroaromatic rings described in this invention refers to the general term for a monovalent group remaining after alicyclic and heteroaromatic rings are fused together and one hydrogen atom is removed. The alicyclic ring preferably has 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, and particularly preferably 3 to 7 carbon atoms. The heteroaromatic ring preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 3 to 15 carbon atoms. Examples may include pyridocyclobutyl, pyridocyclopentyl, pyridocyclohexyl, pyridocycloheptyl, pyridocyclopentenyl, pyridocyclohexenyl, etc., but are not limited thereto.

[0045] The fused alicyclic and aromatic ring groups described in this invention refer to the general term for divalent groups obtained by removing two hydrogen atoms after the alicyclic and aromatic rings are fused together. The aromatic ring preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and most preferably 6 to 14 carbon atoms. The alicyclic ring preferably has 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, and most preferably 3 to 7 carbon atoms. Examples include benzo[a]cyclopropane, benzo[a]cyclobutane, benzo[a]cyclopentane, benzo[a]cyclohexane, benzo[a]cycloheptane, benzo[a]cyclobutenyl, benzo[a]cyclopentenyl, benzo[a]cyclohexenyl, benzo[a]cycloheptenyl, naphtho[a]cyclopropane, naphtho[a]cyclobutane, naphtho[a]cyclopentane, naphtho[a]cyclohexane, naphtho[a]cyclopentenyl, naphtho[a]cyclohexenyl, etc., but are not limited thereto.

[0046] The fused alicyclic and heteroaromatic rings described in this invention refer to the collective term for divalent groups remaining after removing two hydrogen atoms from the fused alicyclic and heteroaromatic rings. The alicyclic ring preferably has 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, and particularly preferably 3 to 7 carbon atoms. The heteroaromatic ring preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 3 to 15 carbon atoms. Examples may include, but are not limited to, pyridinocyclobutyl, pyridinocyclopentyl, pyridinocyclohexyl, pyridinocycloheptyl, pyridinocyclopentenyl, and pyridinocyclohexenyl groups.

[0047] The substituents described in the "substituted or unsubstituted" of this invention may be independently selected from deuterium, cyano, nitro, amino, halogen atoms, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C1-C6 alkylthio, substituted or unsubstituted C1-C12 alkylamine, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C30 arylamine, etc., but are not limited thereto, or adjacent substituents may be linked to form a ring. Preferred atoms include deuterium, cyano, nitro, amino, halogen atoms, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C2-C30 heteroaryl, and C1-C12 alkoxy. Specific examples may include deuterium, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclohexyl, adamantyl, norbornel, phenyl, tolyl, mesitylene, pentadeuterated phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, perylene, pyrene, fluoranyl, and fluorene. 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, spirofluorenyl, 9,9'-spirodifluorenyl, carbazole, 9-phenylcarbazole, carbazole-indole, pyrrole, furanyl, thiophene, dibenzofuranyl, dibenzothiophene, pyridinyl, pyrimidinyl, pyrazinyl, triazinyl, oxazolyl, thiazolyl, imidazolyl, benzoxazolyl, benzothiazolyl, benzotriazolyl, benzoimidazolyl, quinolinyl, isoquinolinyl, quinoxolinyl, quinazolinyl, phenothiazinyl, phenothiazinyl, acridineyl, etc., but not limited to these. Alternatively, when there are multiple substituents, the multiple substituents may be the same or different from each other; or adjacent substituents may be linked to form a ring.

[0048] The "linked ring formation" described in this invention refers to two groups being linked together by chemical bonds and optionally undergoing aromatization. Examples are shown below:

[0049]

[0050] In this invention, the ring formed by the connection can be an aromatic ring system, an aliphatic ring system, or a ring system formed by the fusion of the two. The ring formed by the connection can be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring, or a fused ring, such as benzene, naphthalene, indene, cyclopentene, cyclopentane, cyclopentanophenene, cyclohexene, cyclohexane, cyclohexanophenene, quinoline, isoquinoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, phenanthrene, or pyrene, but is not limited thereto.

[0051] This invention provides an aromatic amine compound, wherein the aromatic amine compound is selected from the structure represented by formula I:

[0052]

[0053] Wherein, Ar1 is selected from chemical formula II;

[0054] The Ar2 is selected from chemical formula III;

[0055]

[0056] The Ar3 is selected from any of the following structures:

[0057]

[0058] L1 is selected from any of the following structures:

[0059]

[0060] Z is selected from either CH or N, and at least one of them is selected from N;

[0061] The V is selected from either CH or N, and at least one of them is selected from N;

[0062] The Y is selected from O, S, C(R) m R n ), N(R e Any one of the following;

[0063] The Y' is selected from O, S, C(R) p R q ), N(R r Any one of the following;

[0064] L2 and L3 are independently selected from any one of the following: single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, and substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic rings.

[0065] The R is selected from any one of substituted or unsubstituted C1-C25 alkyl groups, substituted or unsubstituted C3-C25 alicyclic groups, and substituted or unsubstituted C1-C25 heterocyclic alkyl groups;

[0066] The R1, R2, R3, Ra, R m R n R p R qIndependently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 alicyclic, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl group, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl group, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl group, or R m R n The connections between them form substituted or unsubstituted rings, or R p R q The links between them form substituted or unsubstituted rings;

[0067] The R e R r It is independently selected from any one of the following: substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C3-C25 alicyclic groups, substituted or unsubstituted C1-C25 heterocyclic alkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl groups, substituted or unsubstituted C1-C25 heterocyclic alkanes and C6-C30 aromatic ring fused cycloyl groups, and substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl groups;

[0068] The n1 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; when there are two or more R1s, the two or more R1s are the same or different from each other, or two adjacent R1s are connected to each other to form a substituted or unsubstituted ring;

[0069] The n2 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; when there are two or more R2s, the two or more R2s are the same or different from each other, or two adjacent R2s are connected to each other to form a substituted or unsubstituted ring;

[0070] The n3 is selected from 0, 1, 2, 3, 4 or 5; the n4 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the n5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; the n6 is selected from 0, 1, 2, 3 or 4; the n7 is selected from 0, 1 or 2; the n8 is selected from 0, 1, 2, 3, 4, 5 or 6; the n9 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; when there are two or more R3s, the two or more R3s are the same as or different from each other, or two adjacent R3s are connected to each other to form a substituted or unsubstituted aromatic ring;

[0071] a1 is selected from 0, 1, 2, 3 or 4; a2 is selected from 0, 1, 2, 3, 4, 5 or 6; when there are two or more Ra, the two or more Ra are the same or different from each other, or two adjacent Ra are connected to each other to form a substituted or unsubstituted ring.

[0072] Preferably, Ar1 is selected from any one of the following structures:

[0073]

[0074] More preferably, Ar1 is selected from any one of the following structures:

[0075]

[0076] Preferably, the Ar2 is selected from any one of the following structures:

[0077]

[0078] The Rb is selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C25 alicyclic group, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl group, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl group, and substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl group.

[0079] b1 is selected from 0, 1, 2 or 3; b2 is selected from 0, 1, 2, 3 or 4; b3 is selected from 0, 1, 2, 3, 4 or 5; when there are two or more Rb, the two or more Rb are the same or different from each other, or two adjacent Rb are connected to each other to form a substituted or unsubstituted ring.

[0080] More preferably, the Ar2 is selected from any one of the following structures:

[0081]

[0082]

[0083] The Rf is selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C25 alicyclic group, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl group, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl group, and substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl group.

[0084] f1 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; f2 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; f3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; f4 is selected from 0, 1, 2, 3, 4, or 5; f5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, or 15; f6 The f7 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, or 13; the f8 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, or 19; the f8 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the f9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; the f 10 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12; the f 11 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, or 16; the f 12 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14; the f 13 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20; when there are two or more Rf, the two or more Rf are the same or different from each other, or two adjacent Rf are connected to each other to form a substituted or unsubstituted ring.

[0085] More preferably, the Ar2 is selected from any one of the following structures:

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092] Preferably, the Ar3 is selected from any one of the following structures:

[0093]

[0094]

[0095] The J is selected from either CH or N, and at least one of them is selected from N;

[0096] The Rc is selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C25 alicyclic group, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl group, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl group, and substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl group.

[0097] The c1 is selected from 0, 1, 2, 3, 4 or 5; the c2 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the c3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; the c4 is selected from 0, 1, 2, 3 or 4; the c5 is selected from 0, 1 or 2; the c6 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the c7 is selected from 0, 1, 2, 3, 4, 5 or 6; when there are two or more Rc, the two or more Rc are the same or different from each other, or two adjacent Rc are connected to each other to form a substituted or unsubstituted ring.

[0098] More preferably, the Ar3 is selected from any one of the following structures:

[0099]

[0100]

[0101]

[0102] Preferably, L1 is selected from any one of the following structures:

[0103]

[0104] The V' is selected from either CH or N, and at least one of them is selected from N;

[0105] Rd is selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 alicyclic group, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl group, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl group, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl group;

[0106] The d1 is selected from 0, 1, 2, 3 or 4; the d2 is selected from 0, 1, 2, 3, 4, 5 or 6; the d3 is selected from 0, 1 or 2; the d4 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; when there are two or more Rds, the two or more Rds are the same or different from each other, or two adjacent Rds are connected to each other to form a substituted or unsubstituted ring.

[0107] More preferably, L1 is selected from any of the following structures:

[0108]

[0109] Preferably, L2 and L3 are independently selected from single bonds or selected from any one of the following structures or a combination of two or more of the following structures:

[0110]

[0111] Z' is selected from either CH or N, and at least one of them is selected from N;

[0112] Y1, Y2, and Y3 are independently selected from O, S, and C(R). i R j ), N(R k Any one of the following;

[0113] The Re, R', R i R jIndependently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C25 alicyclic group, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl group, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl group, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl group, or R i R j The links between them form substituted or unsubstituted rings;

[0114] The R k It is selected from any one of the following: substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C3-C25 alicyclic groups, substituted or unsubstituted C1-C25 heterocyclic alkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cyclic groups, substituted or unsubstituted C1-C25 heterocyclic alkanes and C6-C30 aromatic ring fused cyclic groups, and substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cyclic groups.

[0115] The value of n is selected from 0, 1, 2, 3 or 4;

[0116] The e1 is selected from 0, 1, 2, 3 or 4; the e2 is selected from 0, 1, 2, 3, 4, 5 or 6; the e3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the e4 is selected from 0, 1 or 2; the e5 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the e6 is selected from 0, 1, 2 or 3; the e7 is selected from 0, 1, 2, 3, 4 or 5; when there are two or more Re, the two or more Re are the same or different from each other, or two adjacent Re are connected to each other to form a substituted or unsubstituted ring.

[0117] More preferably, L2 and L3 are independently selected from single bonds or selected from any one of the following structures or a combination of two or more of the following structures:

[0118]

[0119]

[0120]

[0121] Most preferably, the aromatic amine compound is selected from any one of the following structures:

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139] The above lists some specific structural forms of aromatic amine compounds represented by chemical formula I according to the present invention. However, the present invention is not limited to these listed chemical structures. Any structure based on the structure shown in chemical formula I, with substituents as defined above, should be included.

[0140] 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 opposite to the anode, the organic layer comprising at least one of the aromatic amine compounds described in the present invention.

[0141] Preferably, the organic layer is located between the anode and the cathode or on the side of the cathode away from the anode, and the organic layer includes a hole transport layer located between the anode and the cathode or a capping layer located on the side of the cathode away from the anode, wherein at least one of the hole transport layer or capping layer contains at least one of the aromatic amine compounds described in this invention.

[0142] Preferably, the organic layer is located between the anode and the cathode, and the organic layer sequentially comprises at least one of a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer, wherein the hole transport layer comprises at least one of the aromatic amine compounds described in this invention.

[0143] Preferably, the hole transport layer comprises a first hole transport layer and a second hole transport layer, the first hole transport layer being located between the anode and the light-emitting layer, the second hole transport layer being located between the first hole transport layer and the light-emitting layer, and at least one of the first hole transport layer and the second hole transport layer comprising at least one of the aromatic amine compounds described in this invention.

[0144] More preferably, the first hole transport layer comprises at least one of the aromatic amine compounds described in this invention.

[0145] More preferably, the second hole transport layer comprises at least one of the aromatic amine compounds described in this invention.

[0146] Preferably, the hole transport layer comprises a first hole transport layer, a second hole transport layer, and a third hole transport layer. The first hole transport layer is located between the anode and the light-emitting layer, the second hole transport layer is located between the first hole transport layer and the light-emitting layer, and the third hole transport layer is located between the second hole transport layer and the light-emitting layer. At least one of the first hole transport layer, the second hole transport layer, and the third hole transport layer comprises at least one of the aromatic amine compounds described in this invention.

[0147] More preferably, the first hole transport layer comprises at least one of the aromatic amine compounds described in this invention.

[0148] More preferably, the second hole transport layer comprises at least one of the aromatic amine compounds described in this invention.

[0149] More preferably, the third hole transport layer comprises at least one of the aromatic amine compounds described in this invention.

[0150] Preferably, the organic layer is located on the side of the cathode opposite to the anode, and the organic layer includes a capping layer containing at least one of the aromatic amine compounds described in this invention.

[0151] The anode of this invention is preferably made of a material with a high work function. The anode includes, but is not limited to, the materials described below: metals or alloys thereof, metal oxides, multilayer materials, conductive polymers, etc. Specific examples may include gold (Au), indium tin oxide (ITO), zinc oxide (ZnO), indium tin oxide / silver / indium tin oxide (ITO / Ag / ITO), polyaniline, etc., but are not limited thereto. The hole injection layer material of this invention is preferably a material with good hole-accepting ability. The hole injection layer material may include, but is not limited to, metalloporphyrins, oligothiophenes, anthraquinone compounds, arylamine derivatives, perylene derivatives, hexanitrile hexaazabenzophenanthrene compounds, quinacridone compounds, anthraquinone compounds, and conductive polymers based on polyaniline and polythiophene, etc.

[0152] The hole injection layer material described in this invention is preferably a material with good hole-accepting ability. The hole injection layer material may include, but is not limited to, metalloporphyrins, oligothiophenes, anthraquinone compounds, arylamine derivatives, perylene derivatives, hexanitrile hexaazabenzophenanthrene compounds, quinacridone compounds, anthraquinone compounds, and conductive polymers based on polyaniline and polythiophene.

[0153] The hole transport layer material described in this invention is preferably a material with good hole transport performance. Besides the aromatic amine compound provided by this invention, other materials that can be used include small molecule materials such as aromatic amine derivatives, carbazole derivatives, stilbene derivatives, triphenyldiamine derivatives, styrene compounds, and butadiene compounds, as well as polymer materials such as poly(p-phenylene) derivatives, polyaniline and its derivatives, polythiophene and its derivatives, polyvinylcarbazole and its derivatives, polysilane and its derivatives, and the aromatic amine compound provided by this invention, but are not limited thereto.

[0154] The luminescent layer material described in this invention can use red, green, or blue luminescent materials, and typically comprises a host material and dopants. The luminescent layer material may contain multiple host materials and multiple dopants. The dopants can be simple fluorescent or phosphorescent materials, or a combination of fluorescent and phosphorescent materials. The doping ratio of the host material and the dopants can vary depending on the materials used; preferably, the doping concentration of the dopant, based on the host compound, is less than 20 wt%. Fluorescent compounds can be used as dopants, such as pyrene derivatives, fluoranthene derivatives, aromatic amine derivatives, etc. Examples include 10-(2-benzothiazolyl)-2,3,6,7-tetrahydro-1,1,7,7-tetramethyl-1H,5H,11H-[1]benzopyran[6,7,8-ij]quinolineazine-11-one (C545T), 4,4'-bis(9-ethyl-3-carbazolevinyl)-1,1'-biphenyl (BCzVBi), 4,4'-bis[4-(di-p-tolylamino)styryl]biphenyl (DPAVBi), etc. Phosphorescent materials can also be used, such as iridium complexes, osmium complexes, platinum complexes and other metal complexes. Examples include bis(4,6-difluorophenylpyridine-N,C2)pyridinecarboxylated iridium (FIrpic), tri(2-phenylpyridine)iridium (Ir(ppy)3), acetylacetonate di(2-phenylpyridine)iridium (Ir(ppy)2(acac)), etc.

[0155] The electron transport material described in this invention is required to have excellent electron transport performance, effectively transporting electrons from the cathode to the light-emitting layer, and possessing a high electron mobility. It may contain any one or more of the following compounds: thiazole derivatives, quinoline derivatives, benzimidazole derivatives, oxazole derivatives, azirbenzene derivatives, diazanthracene derivatives, silicon-containing heterocyclic compounds, boron-containing heterocyclic compounds, cyano compounds, phenanthroline derivatives, metal chelates, etc., but is not limited to these.

[0156] The electron injection layer material described in this invention is preferably a material with good electron-accepting ability. The electron injection layer material may include metals, alkali metals, alkaline earth metals, alkali metal halides, alkaline earth metal halides, alkali metal oxides, alkaline earth metal oxides, alkali metal salts, alkaline earth metal salts, metal complexes, metal oxides, and other substances with high electron-injection properties. Specific examples may include: Li, Ca, Sr, LiF, CsF, CaF2, BaO, Li2CO3, CaCO3, Li2C2O4, Cs2C2O4, CsAlF4, Al2O3, MoO3, MgF2, LiO, Yb, Tb, cesium 8-hydroxyquinoline, tris(8-hydroxyquinoline)aluminum, etc., but are not limited to these.

[0157] The cathode material described in this invention is preferably a material with a low work function. The cathode includes, but is not limited to, the materials described below, metals or their alloys, multilayer materials, etc. Specific examples may include aluminum (Al), silver (Ag), lithium (Li), magnesium (Mg), magnesium:silver (Mg:Ag), etc., but are not limited to these.

[0158] The capping material described in this invention, in addition to the aromatic amine compounds provided by this invention, preferably includes materials with photocoupling properties. Besides the aromatic amine compounds provided by this invention, other materials may include: metal halides, metal oxides, metal nitrides, aromatic amine derivatives, carbazole derivatives, oxazole derivatives, etc. Examples include LiF, CsF, MgF2, CaF2, CsCl, CuI, V2O5, WO3, MoO3, TiO2, ZrO, ZnO, SiO2, SiN, Alq3, but are not limited thereto.

[0159] The following is one method for preparing the compound represented by chemical formula I of this invention, but the preparation method of this invention is not limited thereto. The core structure of the compound of chemical formula I can be prepared by the reaction route shown below. Substituents can be bonded by methods known in the art, and the type and position or number of substituents can be changed according to techniques known in the art.

[0160] [Synthesis Route]

[0161] Preparation of compound I:

[0162]

[0163] Xa and Xb are each independently selected from any one of Cl, Br, and I; the limitations of Ar1, Ar2, Ar3, L1, L2, and L3 are the same as those mentioned above.

[0164] Description of raw materials, reagents, and characterization equipment:

[0165] The present invention does not impose any particular restrictions on the source of raw materials and reagents used in the following embodiments, which can be commercially available products or prepared using preparation methods well known to those skilled in the art.

[0166] Mass spectrometry was performed using a Waters G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer, with chloroform as the solvent.

[0167] Elemental analysis was performed using a VarioELcube organic elemental analyzer from Elementar GmbH, Germany, with sample masses ranging from 5 to 10 mg.

[0168] [Synthetic Example 1] Synthesis of Compound 12

[0169]

[0170] Synthetic intermediate I-12

[0171] Under nitrogen protection, A-12 (10.96 g, 50.00 mmol), B-12 (20.57 g, 50.00 mmol), palladium acetate (0.09 g, 0.40 mmol), tri-tert-butylphosphine (0.16 mL, 0.80 mmol), sodium tert-butoxide (5.77 g, 60.00 mmol), and toluene (400 mL) were added to a reaction flask. The mixture was stirred under reflux for 5 hours, cooled to room temperature, and water was added. The mixture was extracted with ethyl acetate, and the organic phases were combined and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the mixture was recrystallized from toluene / ethanol (10:1) to give intermediate I-12 (22.81 g, yield 83%). The purity of the solid was ≥99.88% as determined by HPLC. Mass spectrometry m / z: 549.2468 (theoretical value: 549.2457).

[0172] Synthetic compound 12

[0173] Under nitrogen protection, intermediates I-12 (13.74 g, 25.00 mmol), C-12 (6.83 g, 25.00 mmol), sodium tert-butoxide (2.88 g, 30.00 mmol), tris(dibenzylacetone)palladium (0.23 g, 0.25 mmol), x-phos (0.24 mL, 0.50 mmol), and toluene (200 mL) were added to a reaction flask, and the reaction was carried out under reflux for 7 hours. After the reaction was completed, the mixture was cooled to room temperature, water was added, the organic phase was separated, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The crude product was recrystallized from toluene to give compound 12 (13.36 g, yield 72%), with a solid purity ≥99.96% as determined by HPLC. Mass spectrometry m / z: 741.3385 (theoretical value: 741.3396). Theoretical elemental content (%) C 57 H 43 N: C, 92.27; H, 5.84; N, 1.89. Measured elemental content (%): C, 92.24; H, 5.86; N, 1.84.

[0174] [Synthetic Example 2] Synthesis of Compound 29

[0175]

[0176] According to the preparation method in Example 1, A-12 was replaced with an equimolar amount of A-29, and C-12 was replaced with an equimolar amount of C-29 to obtain compound 29 (13.60 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 765.3020 (theoretical value: 765.3032). Theoretical elemental content (%) C 58 H 39NO: C, 90.95; H, 5.13; N, 1.83. Measured elemental content (%): C, 90.94; H, 5.15; N, 1.81.

[0177] [Synthetic Example 3] Synthesis of Compound 35

[0178]

[0179] According to the preparation method in Example 1, A-12 was replaced with an equimolar amount of A-35, and C-12 was replaced with an equimolar amount of C-35 to obtain compound 35 (14.09 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 840.3519 (theoretical value: 840.3504). Theoretical elemental content (%) C 64 H 44 N2: C, 91.40; H, 5.27; N, 3.33. Measured elemental content (%): C, 91.42; H, 5.25; N, 3.35.

[0180] [Synthetic Example 4] Synthesis of Compound 46

[0181]

[0182] According to the preparation method in Example 1, A-12 was replaced with an equimolar amount of A-46, and C-12 was replaced with an equimolar amount of C-46 to obtain compound 46 (14.35 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 843.3850 (theoretical value: 843.3865). Theoretical elemental content (%) C 65 H 49 N: C, 92.49; H, 5.85; N, 1.66. Measured element content (%): C, 92.45; H, 5.87; N, 1.63.

[0183] [Synthetic Example 5] Synthesis of Compound 51

[0184]

[0185] According to the preparation method in Example 1, A-12 was replaced with an equimolar amount of A-46 to obtain compound 51 (12.80 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 691.3251 (theoretical value: 691.3239). Theoretical elemental content (%) C 53 H 41 N: C, 92.00; H, 5.97; N, 2.02. Measured elemental content (%): C, 92.02; H, 5.94; N, 2.04.

[0186] [Synthetic Example 6] Synthesis of Compound 67

[0187]

[0188] According to the preparation method in Example 1, A-12 was replaced with an equimolar amount of A-67, and C-12 was replaced with an equimolar amount of C-67 to obtain compound 67 (12.63 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 691.3253 (theoretical value: 691.3239). Theoretical elemental content (%) C 53 H 41 N: C, 92.00; H, 5.97; N, 2.02. Measured elemental content (%): C, 92.02; H, 5.95; N, 2.04.

[0189] [Synthetic Example 7] Synthesis of Compound 76

[0190]

[0191] Synthetic intermediate B-76

[0192] Under nitrogen protection, a-76 (33.52 g, 100 mmol), b-76 (20.64 g, 100 mmol), tetraphenylphosphine palladium (2.31 g, 2.00 mmol), potassium carbonate (27.64 g, 200.00 mmol), and 450 mL of a toluene / ethanol / water (2:1:1) mixed solvent were stirred under reflux for 4 hours. After the reaction was completed, the mixture was cooled to room temperature, toluene was added, and the phases were separated. The toluene phase was washed three times with distilled water, dried over anhydrous magnesium sulfate, and the solvent was concentrated by rotary evaporation. Crystallization was carried out after cooling, and the solid was filtered. The obtained solid was recrystallized from toluene to give intermediate B-76 (35.86 g, 86%); HPLC purity ≥99.75%. Mass spectrometry m / z: 416.1320 (theoretical value: 416.1332).

[0193] Synthetic compound 76

[0194] According to the preparation method in Example 1, A-12 was replaced with an equimolar amount of A-76, and B-12 was replaced with an equimolar amount of B-76 to obtain compound 76 (14.17 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 797.4011 (theoretical value: 797.4022). Theoretical elemental content (%) C 61 H 51 N: C, 91.80; H, 6.44; N, 1.76. Measured elemental content (%): C, 91.83; H, 6.42; N, 1.74.

[0195] [Synthetic Example 8] Synthesis of Compound 81

[0196]

[0197] According to the preparation method in Example 1, A-12 was replaced with an equimolar amount of A-46, and C-12 was replaced with an equimolar amount of C-81 to obtain compound 81 (14.04 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 813.3384 (theoretical value: 813.3396). Theoretical elemental content (%) C 63 H 43 N: C, 92.95; H, 5.32; N, 1.72. Measured element content (%): C, 92.92; H, 5.35; N, 1.73.

[0198] [Synthetic Example 9] Synthesis of Compound 87

[0199]

[0200] According to the preparation method in Example 1, A-12 was replaced with an equimolar amount of A-87, and C-12 was replaced with an equimolar amount of C-81, yielding compound 87 (13.99 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 822.3973 (theoretical value: 822.3960). Theoretical elemental content (%) C 63 H 34 D9N: C, 91.93; H, 6.37; N, 1.70. Measured elemental content (%): C, 91.95; H, 6.34; N, 1.72.

[0201] [Synthetic Example 10] Synthesis of Compound 91

[0202]

[0203] According to the preparation method in Synthesis Example 1, A-12 was replaced with an equimolar amount of A-46, and C-12 was replaced with an equimolar amount of C-91 to obtain compound 91 (15.05 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 925.4632 (theoretical value: 925.4648). Theoretical elemental content (%) C 71 H 59 N: C, 92.07; H, 6.42; N, 1.51. Measured elemental content (%): C, 92.04; H, 6.43; N, 1.55.

[0204] [Synthetic Example 11] Synthesis of Compound 99

[0205]

[0206] According to the preparation method in Example 1, A-12 was replaced with an equimolar amount of A-99, and C-12 was replaced with an equimolar amount of C-81 to obtain compound 99 (14.04 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 813.3382 (theoretical value: 813.3396). Theoretical elemental content (%) C 63 H 43 N: C, 92.95; H, 5.32; N, 1.72. Measured element content (%): C, 92.96; H, 5.34; N, 1.73.

[0207] [Synthetic Example 12] Synthesis of Compound 118

[0208]

[0209] According to the preparation method in Example 1, A-12 was replaced with an equimolar amount of A-118, and C-12 was replaced with an equimolar amount of C-118 to obtain compound 118 (14.24 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 849.3354 (theoretical value: 849.3367). Theoretical elemental content (%) C 63 H 39 D4NS: C, 89.01; H, 5.57; N, 1.65. Measured elemental content (%): C, 89.04; H, 5.55; N, 1.61.

[0210] [Synthetic Example 13] Synthesis of Compound 121

[0211]

[0212] According to the preparation method in Example 1, A-12 was replaced with an equimolar amount of A-46, and C-12 was replaced with an equimolar amount of C-121 to obtain compound 121 (14.08 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 815.3568 (theoretical value: 815.3552). Theoretical elemental content (%) C 63 H 45 N: C, 92.73; H, 5.56; N, 1.72. Measured elemental content (%): C, 92.71; H, 5.57; N, 1.76.

[0213] [Synthetic Example 14] Synthesis of Compound 122

[0214]

[0215] According to the preparation method in Synthesis Example 1, A-12 was replaced with an equimolar amount of A-46, and C-12 was replaced with an equimolar amount of C-122 to obtain compound 122 (13.87 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 815.3541 (theoretical value: 815.3552). Theoretical elemental content (%) C 63 H 45 N: C, 92.73; H, 5.56; N, 1.72. Measured element content (%): C, 92.75; H, 5.53; N, 1.74.

[0216] [Synthetic Example 15] Synthesis of Compound 131

[0217]

[0218] According to the preparation method in Example 1, A-12 was replaced with an equimolar amount of A-46, and C-12 was replaced with an equimolar amount of C-131 to obtain compound 131 (15.08 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 927.4818 (theoretical value: 927.4804). Theoretical elemental content (%) C 71 H 61 N: C, 91.87; H, 6.62; N, 1.51. Measured element content (%): C, 91.85; H, 6.64; N, 1.53.

[0219] [Synthetic Example 16] Synthesis of Compound 149

[0220]

[0221] According to the preparation method in Example 1, A-12 was replaced with an equimolar amount of A-67, and C-12 was replaced with an equimolar amount of C-149 to obtain compound 149 (14.72 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 891.3877 (theoretical value: 891.3865). Theoretical elemental content (%) C 69 H 49 N: C, 92.89; H, 5.54; N, 1.57. Measured elemental content (%): C, 92.86; H, 5.57; N, 1.55.

[0222] [Synthetic Example 17] Synthesis of Compound 151

[0223]

[0224] According to the preparation method in Example 1, A-12 was replaced with an equimolar amount of A-46, and C-12 was replaced with an equimolar amount of C-29 to obtain compound 151 (12.48 g). HPLC analysis showed a solid purity ≥99.99%. Mass spectrometry m / z: 665.2707 (theoretical value: 665.2719). Theoretical elemental content (%) C 50 H 35 NO: C, 90.19; H, 5.30; N, 2.10. Measured elemental content (%): C, 90.15; H, 5.32; N, 2.13.

[0225] [Synthetic Example 18] Synthesis of Compound 171

[0226]

[0227] According to the preparation method in Example 1, A-12 was replaced with an equimolar amount of A-171, and C-12 was replaced with an equimolar amount of C-171 to obtain compound 171 (12.34 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 666.2688 (theoretical value: 666.2671). Theoretical elemental content (%) C 49 H 34 N₂O: C, 88.26; H, 5.14; N, 4.20. Measured elemental content (%): C, 88.22; H, 5.16; N, 4.23.

[0228] [Synthetic Example 19] Synthesis of Compound 197

[0229]

[0230] According to the preparation method in Example 1, A-12 was replaced with an equimolar amount of A-67, and C-12 was replaced with an equimolar amount of C-197 to obtain compound 197 (13.64 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 757.2814 (theoretical value: 757.2803). Theoretical elemental content (%) C 56 H 39 NS: C, 88.74; H, 5.19; N, 1.85. Measured elemental content (%): C, 88.76; H, 5.15; N, 1.82.

[0231] [Synthetic Example 20] Synthesis of Compound 201

[0232]

[0233] According to the preparation method in Example 1, A-12 was replaced with an equimolar amount of A-46, and C-12 was replaced with an equimolar amount of C-35 to obtain compound 201 (14.09 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 816.3519 (theoretical value: 816.3504). Theoretical elemental content (%) C 62 H 44 N2: C, 91.14; H, 5.43; N, 3.43. Measured elemental content (%): C, 91.11; H, 5.46; N, 3.46.

[0234] [Synthetic Example 21] Synthesis of Compound 209

[0235]

[0236] According to the preparation method in Example 1, A-12 was replaced with an equimolar amount of A-46, and C-12 was replaced with an equimolar amount of C-209 to obtain compound 209 (13.96 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 820.3766 (theoretical value: 820.3756). Theoretical elemental content (%) C 62 H 40 D4N2: C, 90.70; H, 5.89; N, 3.41. Measured elemental content (%): C, 90.72; H, 5.86; N, 3.43.

[0237] [Synthetic Example 22] Synthesis of Compound 226

[0238]

[0239] According to the preparation method in Example 1, A-12 was replaced with an equimolar amount of A-226 to obtain compound 226 (13.18 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 731.3536 (theoretical value: 731.3552). Theoretical elemental content (%) C 56 H 45 N: C, 91.89; H, 6.20; N, 1.91. Measured element content (%): C, 91.86; H, 6.22; N, 1.93.

[0240] [Synthetic Example 23] Synthesis of Compound 251

[0241]

[0242] According to the preparation method in Example 1, A-12 was replaced with an equimolar amount of A-226, and C-12 was replaced with an equimolar amount of C-121 to obtain compound 251 (14.34 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 855.3878 (theoretical value: 855.3865). Theoretical elemental content (%) C 66 H 49 N: C, 92.59; H, 5.77; N, 1.64. Measured element content (%): C, 92.56; H, 5.75; N, 1.68.

[0243] [Synthetic Example 24] Synthesis of Compound 254

[0244]

[0245] According to the preparation method in Example 1, A-12 was replaced with an equimolar amount of A-226, and C-12 was replaced with an equimolar amount of C-254 to obtain compound 254 (14.55 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 855.3876 (theoretical value: 855.3865). Theoretical elemental content (%) C 66 H 49 N: C, 92.59; H, 5.77; N, 1.64. Measured element content (%): C, 92.55; H, 5.76; N, 1.68.

[0246] [Synthetic Example 25] Synthesis of Compound 262

[0247]

[0248] According to the preparation method in Example 1, A-12 was replaced with an equimolar amount of A-226, and C-12 was replaced with an equimolar amount of C-262 to obtain compound 262 (14.36 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 869.4010 (theoretical value: 869.4022). Theoretical elemental content (%) C 67 H 51 N: C, 92.48; H, 5.91; N, 1.61. Measured element content (%): C, 92.46; H, 5.94; N, 1.62.

[0249] [Synthetic Example 26] Synthesis of Compound 281

[0250]

[0251] According to the preparation method in Example 1, A-12 was replaced with an equimolar amount of A-226, and C-12 was replaced with an equimolar amount of C-81 to obtain compound 281 (14.52 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 853.3719 (theoretical value: 853.3709). Theoretical elemental content (%) C 66 H 47 N: C, 92.81; H, 5.55; N, 1.64. Measured element content (%): C, 92.82; H, 5.52; N, 1.67.

[0252] [Synthetic Example 27] Synthesis of Compound 316

[0253]

[0254] According to the preparation method in Example 1, A-12 was replaced with an equimolar amount of A-226, and C-12 was replaced with an equimolar amount of C-29 to obtain compound 316 (12.88 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 705.3045 (theoretical value: 705.3032). Theoretical elemental content (%) C 53 H 39 NO: C, 90.18; H, 5.57; N, 1.98. Measured elemental content (%): C, 90.16; H, 5.59; N, 1.96.

[0255] [Synthetic Example 28] Synthesis of Compound 333

[0256]

[0257] According to the preparation method in Example 1, A-12 was replaced with an equimolar amount of A-333, and C-12 was replaced with an equimolar amount of C-333 to obtain compound 333 (14.35 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 831.3513 (theoretical value: 831.3501). Theoretical elemental content (%) C 63 H 45 NO: C, 90.94; H, 5.45; N, 1.68. Measured elemental content (%): C, 90.96; H, 5.46; N, 1.64.

[0258] [Synthetic Example 29] Synthesis of Compound 341

[0259]

[0260] According to the preparation method in Example 1, A-12 was replaced with an equimolar amount of A-341, and C-12 was replaced with an equimolar amount of C-341 to obtain compound 341 (14.17 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 797.3102 (theoretical value: 797.3116). Theoretical elemental content (%) C 59 H 43 NS: C, 88.80; H, 5.43; N, 1.76. Measured elemental content (%): C, 88.83; H, 5.45; N, 1.72.

[0261] [Synthetic Example 30] Synthesis of Compound 357

[0262]

[0263] According to the preparation method in Example 1, A-12 was replaced with an equimolar amount of A-357, and C-12 was replaced with an equimolar amount of C-35, yielding compound 357 (14.36 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 856.3829 (theoretical value: 856.3817). Theoretical elemental content (%) C 65 H 48 N2: C, 91.09; H, 5.64; N, 3.27. Measured elemental content (%): C, 91.05; H, 5.68; N, 3.25.

[0264] [Synthetic Example 31] Synthesis of Compound 371

[0265]

[0266] According to the preparation method in Example 1, A-12 was replaced with an equimolar amount of A-371, and C-12 was replaced with an equimolar amount of C-121 to obtain compound 371 (15.93 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 979.4165 (theoretical value: 979.4178). Theoretical elemental content (%) C 76 H 53 N: C, 93.12; H, 5.45; N, 1.43. Measured element content (%): C, 93.15; H, 5.41; N, 1.46.

[0267] [Synthetic Example 32] Synthesis of Compound 374

[0268]

[0269] According to the preparation method in Example 1, A-12 was replaced with an equimolar amount of A-371, and C-12 was replaced with an equimolar amount of C-374 to obtain compound 374 (15.68 g). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 979.4163 (theoretical value: 979.4178). Theoretical elemental content (%) C 76 H 53 N: C, 93.12; H, 5.45; N, 1.43. Measured element content (%): C, 93.14; H, 5.42; N, 1.45.

[0270] [Synthetic Example 33] Synthesis of Compound 405

[0271]

[0272] According to the preparation method in Example 1, A-12 was replaced with an equimolar amount of A-371, and C-12 was replaced with an equimolar amount of C-405 to obtain compound 405 (16.14 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 977.4039 (theoretical value: 977.4022). Theoretical elemental content (%) C 76 H 51 N: C, 93.31; H, 5.26; N, 1.43. Measured elemental content (%): C, 93.33; H, 5.23; N, 1.45.

[0273] [Synthetic Example 34] Synthesis of Compound 421

[0274]

[0275] According to the preparation method in Example 1, A-12 was replaced with an equimolar amount of A-371, and C-12 was replaced with an equimolar amount of C-29 to obtain compound 421 (14.11 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 829.3331 (theoretical value: 829.3345). Theoretical elemental content (%) C 63 H 43 NO: C, 91.16; H, 5.22; N, 1.69. Measured elemental content (%): C, 91.18; H, 5.25; N, 1.65.

[0276] [Synthetic Example 35] Synthesis of Compound 456

[0277]

[0278] According to the preparation method in Example 1, A-12 was replaced with an equimolar amount of A-456, and C-12 was replaced with an equimolar amount of C-81 to obtain compound 456 (15.62 g). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 975.3850 (theoretical value: 975.3865). Theoretical elemental content (%) C 76 H 49 N: C, 93.51; H, 5.06; N, 1.43. Measured elemental content (%): C, 93.56; H, 5.04; N, 1.41.

[0279] [Synthetic Example 36] Synthesis of Compound 468

[0280]

[0281] According to the preparation method in Example 1, A-12 was replaced with an equimolar amount of A-468, and C-12 was replaced with an equimolar amount of C-91 to obtain compound 468 (15.28 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 939.4455 (theoretical value: 939.4440). Theoretical elemental content (%) C 71 H 57 NO: C, 90.70; H, 6.11; N, 1.49. Measured elemental content (%): C, 90.72; H, 6.13; N, 1.46.

[0282] [Synthetic Example 37] Synthesis of Compound 486

[0283]

[0284] According to the preparation method in Example 1, A-12 was replaced with an equimolar amount of A-468, and C-12 was replaced with an equimolar amount of C-29 to obtain compound 486 (12.58 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 679.2524 (theoretical value: 679.2511). Theoretical elemental content (%) C 50 H 33 NO2: C, 88.34; H, 4.89; N, 2.06. Measured elemental content (%): C, 88.37; H, 4.87; N, 2.04.

[0285] [Synthetic Example 38] Synthesis of Compound 498

[0286]

[0287] According to the preparation method in Example 1, A-12 was replaced with an equimolar amount of A-498, and C-12 was replaced with an equimolar amount of C-498 to obtain compound 498 (12.81 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 711.2067 (theoretical value: 711.2054). Theoretical elemental content (%) C 50 H 33 NS2: C, 84.35; H, 4.67; N, 1.97. Measured elemental content (%): C, 84.38; H, 4.65; N, 1.94.

[0288] [Synthetic Example 39] Synthesis of Compound 516

[0289]

[0290] Synthetic intermediate B-516

[0291] Under nitrogen protection, a-76 (33.52 g, 100 mmol), b-516 (19.64 g, 100 mmol), tetraphenylphosphine palladium (2.31 g, 2.00 mmol), potassium carbonate (27.64 g, 200.00 mmol), and 450 mL of a toluene / ethanol / water (2:1:1) mixed solvent were stirred under reflux for 4.5 hours. After the reaction was complete, the mixture was cooled to room temperature, toluene was added, and the phases were separated. The toluene phase was washed three times with distilled water, dried over anhydrous magnesium sulfate, and the solvent was concentrated by rotary evaporation. Crystallization was carried out at a lower temperature, filtered, and the resulting solid was recrystallized from toluene to give intermediate B-516 (34.59 g, 85%); HPLC purity ≥99.77%. Mass spectrometry m / z: 406.1474 (theoretical value: 406.1488).

[0292] Synthetic compound 516

[0293] According to the preparation method in Example 1, A-12 was replaced with an equimolar amount of A-46, and B-12 was replaced with an equimolar amount of B-516 to obtain compound 516 (12.99 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 731.3568 (theoretical value: 731.3552). Theoretical elemental content (%) C 56 H 45 N: C, 91.89; H, 6.20; N, 1.91. Measured element content (%): C, 91.86; H, 6.22; N, 1.94.

[0294] [Synthetic Example 40] Synthesis of Compound 532

[0295]

[0296] According to the preparation method in Example 1, A-12 was replaced with an equimolar amount of A-532 to obtain compound 532 (12.96 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 709.3156 (theoretical value: 709.3145). Theoretical elemental content (%) C 53 H 40 FN: C, 89.67; H, 5.68; N, 2.68. Measured elemental content (%): C, 89.65; H, 5.66; N, 2.67.

[0297] [Synthetic Example 41] Synthesis of Compound 541

[0298]

[0299] According to the preparation method in Example 1, A-12 was replaced with an equimolar amount of A-541, and C-12 was replaced with an equimolar amount of C-541 to obtain compound 541 (14.08 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 815.3574 (theoretical value: 815.3586). Theoretical elemental content (%) C 60 H 49 NS: C, 88.30; H, 6.05; N, 1.72. Measured elemental content (%): C, 88.33; H, 6.02; N, 1.73.

[0300] [Device Examples]

[0301] A combined IVL testing system was used to test the luminous efficiency of organic electroluminescent devices (OLEDs), comprising testing software, a computer, a Keithley K2400 digital source meter, and a PhotoResearch PR788 spectral scanning luminance meter. Lifetime testing was performed using the McScience M6000 OLED lifetime testing system.

[0302] [Device Example 1]

[0303] The glass substrate was cleaned using distilled water and ultrasonic cleaning. After distilled water washing, ultrasonic cleaning was performed using solvents such as isopropanol, acetone, and methanol, followed by drying. After drying, the substrate was transferred to a plasma cleaner, and then transferred to a vapor deposition machine. Indium tin oxide (ITO) was coated onto the glass substrate to form the anode. Vapor deposition was then performed on the anode. HI-1 is used to form a hole injection layer. Compound 12 of the present invention is deposited on the injection layer to form a layer with a thickness of [missing information]. A hole transport layer is formed. A light-emitting layer is deposited on the hole transport layer, using GH-1 as the host material and 5wt% GD-1 doped with it, forming a layer with a thickness of [missing information]. The light-emitting layer. ET-1 is deposited on the light-emitting layer to form a thickness of [missing information]. An electron transport layer is formed. LiF is deposited on the electron transport layer to form a layer with a thickness of [missing information]. An electron-injected layer is formed. Al is deposited on the electron-injected layer to form a layer with a thickness of [missing information]. The cathode is used to form an organic light-emitting device.

[0304]

[0305] [Device Examples 2-41]

[0306] Compounds 29, 35, 46, 51, 67, 76, 81, 87, 91, 99, 118, 121, 122, 131, 149, 151, 171, 197, 201, 209, 226, 251, 254, 262, 281, 316, 333, 341, 357, 371, 374, 405, 421, 456, 468, 486, 498, 516, 532, and 541 of the present invention were used to replace compound 12 in device example 1 as the hole transport layer material. Otherwise, an organic electroluminescent device was prepared using the same preparation method as device example 1.

[0307] [Comparative Device Examples 1-4]

[0308] Compounds A, B, C, and D were used to replace compound 12 in device example 1 as hole transport layer materials. Otherwise, an organic electroluminescent device was prepared using the same preparation method as in device example 1.

[0309] The test environment was atmospheric, and the temperature was room temperature. The luminescence characteristics test results of devices 1-41 in the device embodiments of the present invention, and those obtained in comparative embodiments 1-4, are shown in Table 1 below.

[0310] Table 1:

[0311]

[0312]

[0313] As shown in Table 1, when the compound described in this invention is used as a hole transport layer material in an organic electroluminescent device, the device exhibits higher luminous efficiency and a longer lifespan. The compound described in this invention is a high-performance hole transport layer material.

[0314] [Device Example 42]

[0315] The glass substrate was cleaned with distilled water and ultrasonically. After distilled water washing, ultrasonic cleaning was performed using solvents such as isopropanol, acetone, and methanol, followed by drying. After drying, the substrate was transferred to a plasma cleaner, and then transferred to a vapor deposition machine. Indium tin oxide (ITO) was coated onto the glass substrate to form the anode. HI-2:HATCN (mass ratio 10:1) was vapor deposited onto the anode to form a thickness of [missing information]. A hole injection layer was formed. HT1 was deposited on the injection layer to form a thickness of [missing information]. The first hole transport layer. Compound 12 of the present invention is deposited on the first hole transport layer to form a layer with a thickness of... The second hole transport layer. A light-emitting layer is deposited on the second hole transport layer, using BH-2 as the host material and 4wt% BD-2 doped with it, forming a layer with a thickness of... The light-emitting layer is formed by evaporating ET-2:Liq (mass ratio 1:1) onto the light-emitting layer to form a thickness of [missing information]. An electron transport layer is formed. LiF is deposited on the electron transport layer to form a layer with a thickness of [missing information]. An electron-injected layer is formed. Al is deposited on the electron-injected layer to form a layer with a thickness of [missing information]. The cathode is used to form an organic light-emitting device.

[0316]

[0317]

[0318] [Device Examples 43-82]

[0319] Compounds 29, 35, 46, 51, 67, 76, 81, 87, 91, 99, 118, 121, 122, 131, 149, 151, 171, 197, 201, 209, 226, 251, 254, 262, 281, 316, 333, 341, 357, 371, 374, 405, 421, 456, 468, 486, 498, 516, 532, and 541 of the present invention were used to replace compound 12 in device example 42 as the second hole transport layer material. Otherwise, an organic electroluminescent device was prepared using the same preparation method as device example 42.

[0320] [Comparative Device Examples 5-8]

[0321] Compounds E, F, G, and H were used to replace compound 12 in device example 42 as the second hole transport layer material. Otherwise, an organic electroluminescent device was prepared using the same preparation method as device example 42.

[0322] The test environment was atmospheric, and the temperature was room temperature. The luminescence characteristics test results of devices 42-82 in the device embodiments of this invention, and those obtained in comparative embodiments 5-8, are shown in Table 2 below.

[0323] Table 2:

[0324]

[0325]

[0326]

[0327] As shown in Table 2, when the compound described in this invention is used as the second hole transport layer material of an organic electroluminescent device, the device has higher luminous efficiency and longer lifespan. The compound described in this invention is a high-performance second hole transport layer material.

[0328] [Device Example 83]

[0329] The glass substrate was cleaned using distilled water and ultrasonic cleaning. After distilled water washing, ultrasonic cleaning was performed using solvents such as isopropanol, acetone, and methanol, followed by drying. After drying, the substrate was transferred to a plasma cleaner, and then transferred to a vapor deposition machine. An anode was formed on the substrate with the reflective layer. HI-3:HATCN (mass ratio 10:1) was vapor deposited on the anode to form a thickness of [missing information]. A hole injection layer was formed. HT-3 was deposited on the injection layer to form a thickness of [missing information]. A hole transport layer is formed. A light-emitting layer is deposited on the hole transport layer, using BH-3 as the host material and doped with 6wt% BD-3, forming a layer with a thickness of [missing information]. The light-emitting layer is formed by evaporating ET-2:Liq (mass ratio 1:1) onto the light-emitting layer to form a thickness of [missing information]. An electron transport layer is formed. LiF is deposited on the electron transport layer to form a layer with a thickness of [missing information]. An electron-injected layer was formed. Mg:Ag (mass ratio 1:1) was deposited on the electron-injected layer to form a layer with a thickness of [missing information]. The cathode. Compound 12 of the present invention is deposited on the cathode layer to form a layer with a thickness of... The covering layer forms an organic light-emitting device.

[0330]

[0331] [Device Examples 84-123]

[0332] Compounds 29, 35, 46, 51, 67, 76, 81, 87, 91, 99, 118, 121, 122, 131, 149, 151, 171, 197, 201, 209, 226, 251, 254, 262, 281, 316, 333, 341, 357, 371, 374, 405, 421, 456, 468, 486, 498, 516, 532, and 541 of the present invention were used to replace compound 12 in device example 83 as the capping layer material. Otherwise, an organic electroluminescent device was prepared using the same preparation method as device example 83.

[0333] [Comparative Device Examples 9-10]

[0334] Compounds J and K were used to replace compound 12 in device example 83 as the capping material, respectively. Otherwise, the organic electroluminescent device was prepared by the same preparation method as device example 83.

[0335] The test environment was atmospheric, and the temperature was room temperature. The luminescence characteristics test results of the organic electroluminescent devices obtained in the device embodiments of the present invention 83-123 and comparative embodiments 9-10 are shown in Table 3 below.

[0336] Table 3:

[0337]

[0338]

[0339] As shown in Table 3, when the compound described in this invention is used as a capping material for organic electroluminescent devices, the devices exhibit higher luminous efficiency and longer lifespan. The compound described in this invention is a high-performance capping material.

[0340] It should be noted that the present invention has been specifically described with reference to specific embodiments. For those skilled in the art, various improvements and modifications can be made to the present invention without departing from the principle of the present invention, and these improvements and modifications also fall within the protection scope of the present invention.

Claims

1. An arylamine compound, characterized by, The arylamine compound has a structure represented by Formula I: wherein the Ar1 is selected from the group consisting of Formula II; the Ar2 is selected from the group consisting of Formula III; the Ar3 is selected from any one of the following structures: the L1 is selected from any one of the following structures: the Z is selected from any one of CH and N, and at least one is selected from N; the V is selected from any one of CH and N, and at least one is selected from N; said Y is selected from O, S, C(R m R n )N(R e ) in any order; said Y' is selected from O, S, C(R p R q ), N(R r ) in any order; the L2 and L3 are independently selected from any one of a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C2-C30 heteroarylene group, a substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring group, a substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic fused ring group; the R is selected from any one of a substituted or unsubstituted C1-C25 alkyl group, a substituted or unsubstituted C3-C25 alicyclic group, and a substituted or unsubstituted C1-C25 heterocyclic alkyl group; R1, R2, R3, Ra, R m , R n , R p , R q are independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 alicyclyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclyl and C6-C30 aryl fused ring group, substituted or unsubstituted C1-C25 heterocycloalkane and C6-C30 aryl fused ring group, substituted or unsubstituted C3-C25 alicyclyl and C2-C30 heteroaryl fused ring group, or R m , R n are linked to form a substituted or unsubstituted ring, or R p , R q are linked to form a substituted or unsubstituted ring; said R e , R r is independently selected from any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C25 alicyclyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclyl and C6-C30 aryl fused ring group, substituted or unsubstituted C1-C25 heterocycloalkane and C6-C30 aryl fused ring group, substituted or unsubstituted C3-C25 alicyclyl and C2-C30 heteroaryl fused ring group; the n1 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; when two or more R1 are present, the two or more R1 are the same as or different from each other, or adjacent two R1 are connected to each other to form a substituted or unsubstituted ring; the n2 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; when two or more R2 are present, the two or more R2 are the same as or different from each other, or adjacent two R2 are connected to each other to form a substituted or unsubstituted ring; the n3 is selected from 0, 1, 2, 3, 4, or 5; the n4 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; the n5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; the n6 is selected from 0, 1, 2, 3, or 4; the n7 is selected from 0, 1, or 2; the n8 is selected from 0, 1, 2, 3, 4, 5, or 6; the n9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; when two or more R3 are present, the two or more R3 are the same as or different from each other, or adjacent two R3 are connected to each other to form a substituted or unsubstituted aromatic ring; the a1 is selected from 0, 1, 2, 3, or 4; the a2 is selected from 0, 1, 2, 3, 4, 5, or 6; when two or more Ra are present, the two or more Ra are the same as or different from each other, or adjacent two Ra are connected to each other to form a substituted or unsubstituted ring.

2. The arylamine compound according to claim 1, characterized by the Ar1 is selected from any one of the following structures:

3. The arylamine compound according to claim 1, characterized by the Ar2 is selected from any one of the following structures: Rb is selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C25 alicyclyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted fused ring group of C3-C30 alicyclyl and C6-C30 aryl, substituted or unsubstituted fused ring group of C1-C25 heterocycloalkyl and C6-C30 aryl, substituted or unsubstituted fused ring group of C3-C25 alicyclyl and C2-C30 heteroaryl; b1 is selected from 0, 1, 2 or 3; b2 is selected from 0, 1, 2, 3 or 4; b3 is selected from 0, 1, 2, 3, 4 or 5; when there are two or more Rb, the two or more Rb are the same as or different from each other, or adjacent two Rb are connected to each other to form a substituted or unsubstituted ring.

4. The arylamine compound according to claim 1, wherein Ar2 is selected from any one of the following structures: Rf is selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C25 alicyclyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted fused ring group of C3-C30 alicyclyl and C6-C30 aryl, substituted or unsubstituted fused ring group of C1-C25 heterocycloalkyl and C6-C30 aryl, substituted or unsubstituted fused ring group of C3-C25 alicyclyl and C2-C30 heteroaryl; said f1 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; said f2 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; said f3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; said f4 is selected from 0, 1, 2, 3, 4, or 5; said f5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, or 15; said f6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, or 13; said f7 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, or 19; said f8 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; said f9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; said f 10 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12; said f 11 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, or 16; said f 12 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14; said f 13 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20; when there are two or more Rf, two or more Rf are the same or different from each other, or two adjacent Rf are connected to each other to form a substituted or unsubstituted ring.

5. The arylamine compound according to claim 1, wherein Ar3 is selected from any one of the following structures: J is selected from any one of CH and N, and at least one is selected from N; Rc is selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C25 alicyclyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted fused ring group of C3-C30 alicyclyl and C6-C30 aryl, substituted or unsubstituted fused ring group of C1-C25 heterocycloalkyl and C6-C30 aryl, substituted or unsubstituted fused ring group of C3-C25 alicyclyl and C2-C30 heteroaryl; c1 is selected from 0, 1, 2, 3, 4 or 5; c2 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; c3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; c4 is selected from 0, 1, 2, 3 or 4; c5 is selected from 0, 1 or 2; c6 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; c7 is selected from 0, 1, 2, 3, 4, 5 or 6; when there are two or more Rc, the two or more Rc are the same as or different from each other, or adjacent two Rc are connected to each other to form a substituted or unsubstituted ring.

6. The arylamine compound according to claim 1, wherein L1 is selected from any one of the following structures: V' is selected from any one of CH, N, and at least one is N; Rd is selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 alicyclic group, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aryl fused ring group, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aryl fused ring group, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaryl fused ring group; d1 is selected from 0, 1, 2, 3 or 4; d2 is selected from 0, 1, 2, 3, 4, 5 or 6; d3 is selected from 0, 1 or 2; d4 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; when there are two or more Rd, the two or more Rd are the same as or different from each other, or two adjacent Rd are connected to each other to form a substituted or unsubstituted ring.

7. The arylamine compound according to claim 1, wherein L2 and L3 are independently selected from a single bond or any one of the following structures or a combination of two or more of the following structures: Z' is selected from any one of CH, N, and at least one is N; Y1, Y2, Y3are independently selected from O, S, C(R i R j ), N(R k ) in any one of the following combinations: The Re, R', R i R j Independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C25 alicyclic group, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl group, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl group, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl group, or R i R j The links between them form substituted or unsubstituted rings; R is selected from any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C25 alicyclyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclo and C6-C30 aryl fused ring group, substituted or unsubstituted C1-C25 heterocycloalkane and C6-C30 aryl fused ring group, substituted or unsubstituted C3-C25 alicyclo and C2-C30 heteroaryl fused ring group; k R is selected from any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C25 alicyclyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclo and C6-C30 aryl fused ring group, substituted or unsubstituted C1-C25 heterocycloalkane and C6-C30 aryl fused ring group, substituted or unsubstituted C3-C25 alicyclo and C2-C30 heteroaryl fused ring group; n is selected from 0, 1, 2, 3 or 4; e1 is selected from 0, 1, 2, 3 or 4; e2 is selected from 0, 1, 2, 3, 4, 5 or 6; e3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; e4 is selected from 0, 1 or 2; e5 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; e6 is selected from 0, 1, 2 or 3; e7 is selected from 0, 1, 2, 3, 4 or 5; when there are two or more Re, the two or more Re are the same as or different from each other, or two adjacent Re are connected to each other to form a substituted or unsubstituted ring.

8. The arylamine compound according to claim 1, wherein The arylamine compound is selected from any one of the following structures:

9. An organic electroluminescent device comprising an anode, a cathode, and an organic layer between the anode and the cathode or on the side of the cathode facing away from the anode, characterized in that The organic layer comprises at least one of the arylamine compounds of any one of claims 1 to 8.

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

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