Arylamine compound, organic electroluminescent device and electronic equipment

Abstract

According to the organic compound, the organic electroluminescent element and the electronic equipment provided by the invention, the compound with the benzocarbazole structure and the phenylene-dibenzofuran structure is high in hole transmission capability, can rapidly transmit holes to a light-emitting layer, has a proper energy level, can limit current carriers in the light-emitting layer, and improves the light-emitting efficiency. The organic electroluminescent element prepared from the compound disclosed by the invention has lower driving voltage and higher current efficiency, and is suitable for preparing the high-performance organic electroluminescent element. The compound has a structure as shown in a formula (1), # imgabs0, Ar3 has the following structure: # imgabs1 # A1 is selected from aromatic rings, A2 is selected from aromatic rings, L5 is selected from arylene, L4 is selected from dibenzofuranyl and dibenzothienyl, L1-L3 are respectively and independently selected from single bonds, arylene and heteroaryl, and Ar1 and Ar2 are respectively and independently selected from hydrogen, deuterium, halogen, cyano, alkyl, cycloalkyl, alkoxy, alkenyl, alkynyl, aryl and heteroaryl.

Description

Technical Field

[0001] The present invention relates to the field of organic electroluminescent technology, and more particularly, to an arylamine compound, an organic electroluminescent device and an electronic device. Background Art

[0002] An organic light emitting diode is a self-luminous display device based on organic electroluminescent materials, which has the characteristics of not requiring a backlight source and being thin, and is a technology suitable for flexible light emitting display devices.

[0003] Organic electroluminescent materials are high molecular or small molecular organic materials that can emit light under the action of an electric field. In order to improve the stability and efficiency of organic electroluminescent materials in organic electroluminescent devices, multiple layers of organic thin films are prepared between the anode and the cathode. The above-mentioned organic thin film layers can be divided into a hole injection layer, a hole transport layer, a light-emitting layer host, a light-emitting layer dopant, an electron transport layer, and an electron injection layer.

[0004] When an electric field is applied between the anode and the cathode of an organic electroluminescent device, holes are injected from the anode, and the injected holes move to the light-emitting layer through the hole transport layer. At the same time, electrons are injected from the cathode, and the injected electrons move to the light-emitting layer through the electron transport layer. The holes and electrons that move to the light-emitting layer combine to form excitons. When the excitons transition from the excited state to the ground state, energy is released in the form of light, realizing the light emission of the device.

[0005] To ensure the high performance (longer lifespan, higher current efficiency, lower driving voltage, higher color saturation, etc.) of organic electroluminescent devices, it is particularly important to improve the exciton generation efficiency of the light-emitting layer. In order to prevent the diffusion of excitons, as a hole transport material, it is required to have a high triplet energy.

[0006] At present, although there are reports of high-performance organic electroluminescent devices, the performance of the hole transport region has not been fully developed, and the existing hole transport region materials still cannot meet the requirements for high-performance organic electroluminescent devices. Summary of the Invention

[0007] In view of the above-mentioned defects or improvement requirements of the prior art, the present invention provides an arylamine derivative with a specific parent nucleus, which is used as an organic electroluminescent material, and especially shows excellent performance when used as a hole transport region material.

[0008] To achieve the above object, the present invention provides an arylamine compound, which has the structure shown in formula (1).

[0009]

[0010] Among them, Ar3 has the following structure:

[0011]

[0012] "----" represents the connection position;

[0013] A1 is selected from a substituted or unsubstituted C6-C14 aromatic ring,

[0014] A2 is selected from a substituted or unsubstituted C10-C14 aromatic ring,

[0015] L5 is selected from a substituted or unsubstituted C6-C60 arylene,

[0016] L4 is selected from a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl,

[0017] L1-L3 are each independently selected from a single bond, a substituted or unsubstituted C6-C60 arylene, a substituted or unsubstituted C3-C60 heteroarylene,

[0018] Ar1 and Ar2 are each independently selected from hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C1-C10 alkyl, a substituted or unsubstituted C3-C10 cycloalkyl, a substituted or unsubstituted C1-C10 alkoxy, a substituted or unsubstituted C2-C10 alkenyl, a substituted or unsubstituted C2-C10 alkynyl, a substituted or unsubstituted C6-C60 aryl, a substituted or unsubstituted C3-C60 heteroaryl;

[0019] When "substituted or unsubstituted", the substituents for substitution are selected from deuterium, halogen, cyano, C1-C10 alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C2-C10 alkenyl, C2-C10 alkynyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 carbocyclic group, C3-C60 heterocyclic group,

[0020] The heteroatoms in the heterocyclic group and heteroaryl are selected from at least one of N, O, S, Si, P.

[0021] Furthermore, in an alternative embodiment of the present invention, the compound has the structure shown in formula (2),

[0022]

[0023] R2 is selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C2-C10 alkynyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl;

[0024] b is an integer between 0 and 10, preferably an integer from 0 to 9, more preferably an integer from 0 to 8, more preferably an integer from 0 to 7, more preferably an integer between 0-6, more preferably an integer between 0-5, more preferably an integer between 0-4, still more preferably 0, 1, 2, 3, particularly preferably 0, 1, 2, especially preferably 0, 1, most preferably 0; when b is 2 or greater, multiple R2s are the same as or different from each other;

[0025] The definitions of L1-L5, Ar1, and Ar2 are the same as those defined in the compound of formula (1) above;

[0026] The definition of the substituent when substituted in the "substituted or unsubstituted" is preferably the same as above;

[0027] Preferably, L3 is a single bond;

[0028] Preferably, L5 is selected from phenylene, naphthylene, biphenylene;

[0029] Preferably, L4 is selected from dibenzofuranylene, dibenzothiophenylene; more preferably, L4 is selected from dibenzofuranylene.

[0030] In an alternative embodiment of the present invention, in the structure shown by formula (2) of the arylamine compound, R2 is selected from deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C2-C10 alkynyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl;

[0031] The definition of the substituent when substituted in the "substituted or unsubstituted" is preferably the same as above.

[0032] Furthermore, in an alternative embodiment of the present invention, the arylamine compound has the structure shown by formula (2-1),

[0033]

[0034] Among them, R1-R3 are each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C2-C10 alkynyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl;

[0035] a is an integer between 0 and 4, preferably 0, 1, 2, 3, more preferably 0, 1, 2, and most preferably 0; when a is 2 or greater, multiple R1s are the same as or different from each other;

[0036] b is an integer between 0 and 10, preferably an integer from 0 to 9, more preferably an integer from 0 to 8, more preferably an integer from 0 to 7, more preferably an integer between 0 and 6, more preferably an integer between 0 and 5, more preferably an integer between 0 and 4, still more preferably 0, 1, 2, 3, particularly preferably 0, 1, 2, especially preferably 0, 1, and most preferably 0; when b is 2 or greater, multiple R2s are the same as or different from each other;

[0037] c is an integer between 0 and 6; preferably an integer between 0 and 5, more preferably an integer between 0 and 4, still more preferably 0, 1, 2, 3, particularly preferably 0, 1, 2, especially preferably 0, 1, and most preferably 0; when c is 2 or greater, multiple R3s are the same as or different from each other;

[0038] X is selected from O or S;

[0039] The definitions of L1, L2, Ar1, and Ar2 are the same as those defined in the compound of formula (1) above;

[0040] The definition of the substituent when substituted in the "substituted or unsubstituted" is preferably the same as above.

[0041] Furthermore, in an alternative embodiment of the present invention, the aromatic amine compound has the structures shown in formulas (3)-(8),

[0042]

[0043]

[0044] Among them, R1 - R3 are each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1 - C10 alkyl, substituted or unsubstituted C3 - C10 cycloalkyl, substituted or unsubstituted C1 - C10 alkoxy, substituted or unsubstituted C2 - C10 alkenyl, substituted or unsubstituted C2 - C10 alkynyl, substituted or unsubstituted C6 - C60 aryl, substituted or unsubstituted C3 - C60 heteroaryl;

[0045] a is an integer between 0 and 4, preferably 0, 1, 2, 3, more preferably 0, 1, 2, and most preferably 0; when a is 2 or greater, multiple R1s are the same as or different from each other;

[0046] b is an integer between 0 and 10, preferably an integer from 0 to 9, more preferably an integer from 0 to 8, more preferably an integer from 0 to 7, more preferably an integer between 0 - 6, more preferably an integer between 0 - 5, more preferably an integer between 0 - 4, more preferably 0, 1, 2, 3, particularly preferably 0, 1, 2, especially preferably 0, 1, and most preferably 0; when b is 2 or greater, multiple R2s are the same as or different from each other;

[0047] c is an integer between 0 and 6; preferably an integer between 0 - 5, more preferably an integer between 0 - 4, more preferably 0, 1, 2, 3, particularly preferably 0, 1, 2, especially preferably 0, 1, and most preferably 0; when c is 2 or greater, multiple R3s are the same as or different from each other;

[0048] X is selected from O or S;

[0049] The definitions of L1, L2, Ar1, and Ar2 are the same as those defined in the compound of formula (1) above;

[0050] The definition of the substituent when substituted in the "substituted or unsubstituted" is preferably the same as above.

[0051] In an alternative embodiment of the present invention, in the arylamine compounds of the structures shown in formulas (3) - (8), R1 - R3 are each independently selected from deuterium, halogen, cyano, substituted or unsubstituted C1 - C10 alkyl, substituted or unsubstituted C3 - C10 cycloalkyl, substituted or unsubstituted C1 - C10 alkoxy, substituted or unsubstituted C2 - C10 alkenyl, substituted or unsubstituted C2 - C10 alkynyl, substituted or unsubstituted C6 - C60 aryl, substituted or unsubstituted C3 - C60 heteroaryl;

[0052] The definition of the substituent when substituted in the "substituted or unsubstituted" is preferably the same as above.

[0053] Further, in an alternative embodiment of the present invention, the arylamine compound has the following structure:

[0054]

[0055] R1-R3, X, a, b, c, L1, L2, Ar1, and Ar2 are defined in the same manner as in the compounds of formulas (3)-(8) above.

[0056] Further, in an alternative embodiment of the present invention, the arylamine compound has the following structure:

[0057]

[0058] R1-R3, X, a, b, c, L1, L2, Ar1, and Ar2 are defined in the same manner as in the compounds of formulas (3)-(8) above.

[0059] Further, in an alternative embodiment of the present invention, the arylamine compound has the structures shown in formulas (9)-(26),

[0060]

[0061]

[0062] wherein R1-R3 are each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C2-C10 alkynyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl;

[0063] a is an integer between 0 and 4, preferably 0, 1, 2, 3, more preferably 0, 1, 2, and most preferably 0; when a is 2 or greater, the multiple R1s are the same or different from each other;

[0064] b is an integer between 0 and 10, preferably an integer from 0 to 9, more preferably an integer from 0 to 8, more preferably an integer from 0 to 7, more preferably an integer between 0-6, more preferably an integer between 0-5, more preferably an integer between 0-4, still more preferably 0, 1, 2, 3, particularly preferably 0, 1, 2, especially preferably 0, 1, and most preferably 0; when b is 2 or greater, the multiple R2s are the same or different from each other;

[0065] c is an integer selected from 0 to 6; preferably an integer from 0 to 5, more preferably an integer from 0 to 4, even more preferably 0, 1, 2, 3, particularly preferably 0, 1, 2, especially preferably 0, 1, and most preferably 0; when c is 2 or greater, the plurality of R3s are the same as or different from each other;

[0066] X is selected from O or S;

[0067] L1, L2, Ar1, and Ar2 are defined in the same way as in the compound of formula (1) above;

[0068] The definition of the substituent when substituted in the "substituted or unsubstituted" is preferably the same as above.

[0069] In an alternative embodiment of the present invention, in the structures represented by formula (9)-(26) of the arylamine compound, R1-R3 are each independently selected from deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C2-C10 alkynyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl;

[0070] The definition of the substituent when substituted in the "substituted or unsubstituted" is preferably the same as above.

[0071] Preferably, R1-R3 are each independently selected from deuterium, halogen, phenyl, biphenyl, naphthyl, anthracenyl, phenanthryl, fluoranthenyl, pyrenyl, perylenyl, triphenylenyl, pyrrolyl, furyl, thienyl, indenyl, indolyl, benzofuryl, benzothienyl, dibenzofuryl, dibenzothienyl, carbazolyl, carbolinyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirobifluorenyl;

[0072] a is an integer selected from 0 to 4; b is an integer selected from 0 to 10; c is an integer selected from 0 to 6;

[0073] Preferably, X is selected from O or S; more preferably, X is selected from O;

[0074] Preferably, L1 and L2 are each independently selected from a single bond, phenylene, biphenylene, naphthylene, anthracenylene, phenanthrylene, fluoranthenylene, pyrenylene, perylenylene, triphenylenylene, pyrrolylene, furylene, thienylene, indenylene, indolylene, benzofurylene, benzothienylene, dibenzofurylene, dibenzothienylene, carbazolylene, carbolinylene, 9,9-dimethylfluorenylene, 9,9-diphenylfluorenylene, spirobifluorenylene;

[0075] Preferably, each of Ar1 and Ar2 is independently selected from hydrogen, deuterium, halogen, phenyl, biphenyl, naphthyl, anthracenyl, phenanthryl, fluoranthenyl, pyrenyl, perylenyl, triphenylenyl, pyrrolyl, furyl, thienyl, indenyl, indolyl, benzofuryl, benzothienyl, dibenzofuryl, dibenzothienyl, carbazolyl, carbolinyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirobifluorenyl, benzonaphthofuryl, benzonaphthothienyl, phenyl-substituted carbazole, naphthyl-substituted carbazolyl, biphenyl-substituted carbazolyl;

[0076] Preferably, the structure is unsubstituted or substituted with one or more deuteriums, and most preferably the structure is unsubstituted.

[0077] Furthermore, in an alternative embodiment of the present invention, each of L1 and L2 is independently selected from a single bond, a substituted or unsubstituted group as follows:

[0078]

[0079] The definition of the substituent when substituted in the "substituted or unsubstituted" is preferably the same as above.

[0080] Furthermore, in an alternative embodiment of the present invention, each of Ar1 and Ar2 is independently selected from hydrogen, a substituted or unsubstituted group as follows:

[0081]

[0082] The definition of the substituent when substituted in the "substituted or unsubstituted" is preferably the same as above.

[0083] Furthermore, in an alternative embodiment of the present invention, the definition of the substituent when substituted in the above "substituted or unsubstituted" is preferably independently selected from one or more combinations of deuterium, fluoro group, cyano group, methyl group, ethyl group, tert-butyl group, cyclohexyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, fluoranthenyl group, triphenylenyl group, group, dibenzofuryl group, dibenzothienyl group.

[0084] Furthermore, in an alternative embodiment of the present invention, Ar3-L5-L4-L3- is selected from the following structures: X-m-n is the substituent number represented by Ar3-L5-L4-L3-, and X-m-n represents all substituents represented by X-1-1 to X-1-24, X-2-1 to X-2-24, X-3-1 to X-3-24,

[0085]

[0086]

[0087]

[0088]

[0089] Furthermore, in an alternative embodiment of the present invention, each of -L1-Ar1 and -L2-Ar2 is independently selected from the following structures:

[0090]

[0091]

[0092]

[0093]

[0094] Wherein, the structure is unsubstituted or substituted with one or more deuteriums, and most preferably the structure is unsubstituted.

[0095] Preferably, each of -L1-Ar1 and -L2-Ar2 is independently selected from the structures of Formula Y1 to Formula Y85, wherein the structure is unsubstituted or substituted with one or more deuteriums, and most preferably the structure is unsubstituted.

[0096] Furthermore, in an alternative embodiment of the present invention, the aromatic amine compound is selected from the following structures:

[0097] Wherein, Ar3-L5-L4-L3-, -L1-Ar1, and -L2-Ar2 are respectively connected to N;

[0098]

[0099]

[0100]

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[0147]

[0148] When Ar3-L5-L4-L3- is selected from X-3-1, the compound numbers are X-3-1-1 to X-3-1-3655,

[0149] When Ar3-L5-L4-L3- is replaced with X-1-1 for X-3-1, the compound numbers are X-1-1-1 to X-1-1-3655,

[0150] When Ar3-L5-L4-L3- is replaced with X-1-2 for X-3-1, the compound numbers are X-1-2-1 to X-1-2-3655,

[0151] When Ar3-L5-L4-L3- is replaced with X-1-3 for X-3-1, the compound numbers are X-1-3-1 to X-1-3-3655,

[0152] When Ar3-L5-L4-L3- is replaced with X-1-4 for X-3-1, the compound numbers are X-1-4-1 to X-1-4-3655,

[0153] When Ar3-L5-L4-L3- is replaced with X-1-5 for X-3-1, the compound numbers are X-1-5-1 to X-1-5-3655,

[0154] When X-3-1 is replaced with X-1-6 in Ar3-L5-L4-L3, the compound numbers are X-1-6-1 to X-1-6-3655,

[0155] When X-3-1 is replaced with X-1-7 in Ar3-L5-L4-L3, the compound numbers are X-1-7-1 to X-1-7-3655,

[0156] When X-3-1 is replaced with X-1-8 in Ar3-L5-L4-L3, the compound numbers are X-1-8-1 to X-1-8-3655,

[0157] When X-3-1 is replaced with X-1-9 in Ar3-L5-L4-L3, the compound numbers are X-1-9-1 to X-1-9-3655,

[0158] When X-3-1 is replaced with X-1-10 in Ar3-L5-L4-L3, the compound numbers are X-1-10-1 to X-1-10-3655,

[0159] When X-3-1 is replaced with X-1-11 in Ar3-L5-L4-L3, the compound numbers are X-1-11-1 to X-1-11-3655,

[0160] When X-3-1 is replaced with X-1-12 in Ar3-L5-L4-L3, the compound numbers are X-1-12-1 to X-1-12-3655,

[0161] When X-3-1 is replaced with X-1-13 in Ar3-L5-L4-L3, the compound numbers are X-1-13-1 to X-1-13-3655,

[0162] When X-3-1 is replaced with X-1-14 in Ar3-L5-L4-L3, the compound numbers are X-1-14-1 to X-1-14-3655,

[0163] When X-3-1 is replaced with X-1-15 in Ar3-L5-L4-L3, the compound numbers are X-1-15-1 to X-1-15-3655,

[0164] When X-3-1 is replaced with X-1-16 in Ar3-L5-L4-L3, the compound numbers are X-1-16-1 to X-1-16-3655,

[0165] When X-3-1 is replaced with X-1-17 in Ar3-L5-L4-L3, the compound numbers are X-1-17-1 to X-1-17-3655,

[0166] When X-3-1 is replaced by X-1-18 in Ar3-L5-L4-L3, the compound numbers are X-1-18-1 to X-1-18-3655,

[0167] When X-3-1 is replaced by X-1-19 in Ar3-L5-L4-L3, the compound numbers are X-1-19-1 to X-1-19-3655,

[0168] When X-3-1 is replaced by X-1-20 in Ar3-L5-L4-L3, the compound numbers are X-1-20-1 to X-1-20-3655,

[0169] When X-3-1 is replaced by X-1-21 in Ar3-L5-L4-L3, the compound numbers are X-1-21-1 to X-1-21-3655,

[0170] When X-3-1 is replaced by X-1-22 in Ar3-L5-L4-L3, the compound numbers are X-1-22-1 to X-1-22-3655,

[0171] When X-3-1 is replaced by X-1-23 in Ar3-L5-L4-L3, the compound numbers are X-1-23-1 to X-1-23-3655,

[0172] When X-3-1 is replaced by X-1-24 in Ar3-L5-L4-L3, the compound numbers are X-1-24-1 to X-1-24-3655,

[0173] When X-3-1 is replaced by X-2-1 in Ar3-L5-L4-L3, the compound numbers are X-2-1-1 to X-2-1-3655,

[0174] When X-3-1 is replaced by X-2-2 in Ar3-L5-L4-L3, the compound numbers are X-2-2-1 to X-2-2-3655,

[0175] When X-3-1 is replaced by X-2-3 in Ar3-L5-L4-L3, the compound numbers are X-2-3-1 to X-2-3-3655,

[0176] When X-3-1 is replaced by X-2-4 in Ar3-L5-L4-L3, the compound numbers are X-2-4-1 to X-2-4-3655,

[0177] When X-3-1 is replaced by X-2-5 in Ar3-L5-L4-L3, the compound numbers are X-2-5-1 to X-2-5-3655,

[0178] When X-3-1 is replaced by X-2-6 in Ar3-L5-L4-L3, the compound numbers are X-2-6-1 to X-2-6-3655,

[0179] When X-3-1 is replaced by X-2-7 in Ar3-L5-L4-L3, the compound numbers are X-2-7-1 to X-2-7-3655,

[0180] When X-3-1 is replaced by X-2-8 in Ar3-L5-L4-L3, the compound numbers are X-2-8-1 to X-2-8-3655,

[0181] When X-3-1 is replaced by X-2-9 in Ar3-L5-L4-L3, the compound numbers are X-2-9-1 to X-2-9-3655,

[0182] When X-3-1 is replaced by X-2-10 in Ar3-L5-L4-L3, the compound numbers are X-2-10-1 to X-2-10-3655,

[0183] When X-3-1 is replaced by X-2-11 in Ar3-L5-L4-L3, the compound numbers are X-2-11-1 to X-2-11-3655,

[0184] When X-3-1 is replaced by X-2-12 in Ar3-L5-L4-L3, the compound numbers are X-2-12-1 to X-2-12-3655,

[0185] When X-3-1 is replaced by X-2-13 in Ar3-L5-L4-L3, the compound numbers are X-2-13-1 to X-2-13-3655,

[0186] When X-3-1 is replaced by X-2-14 in Ar3-L5-L4-L3, the compound numbers are X-2-14-1 to X-2-14-3655,

[0187] When X-3-1 is replaced by X-2-15 in Ar3-L5-L4-L3, the compound numbers are X-2-15-1 to X-2-15-3655,

[0188] When X-3-1 is replaced by X-2-16 in Ar3-L5-L4-L3, the compound numbers are X-2-16-1 to X-2-16-3655,

[0189] When X-3-1 is replaced by X-2-17 in Ar3-L5-L4-L3, the compound numbers are X-2-17-1 to X-2-17-3655,

[0190] When X-3-1 is replaced by X-2-18 in Ar3-L5-L4-L3, the compound numbers are X-2-18-1 to X-2-18-3655,

[0191] When X-3-1 is replaced by X-2-19 in Ar3-L5-L4-L3, the compound numbers are X-2-19-1 to X-2-19-3655,

[0192] When X-3-1 is replaced by X-2-20 in Ar3-L5-L4-L3, the compound numbers are X-2-20-1 to X-2-20-3655,

[0193] When X-3-1 is replaced by X-2-21 in Ar3-L5-L4-L3, the compound numbers are X-2-21-1 to X-2-21-3655,

[0194] When X-3-1 is replaced by X-2-22 in Ar3-L5-L4-L3, the compound numbers are X-2-22-1 to X-2-22-3655,

[0195] When X-3-1 is replaced by X-2-23 in Ar3-L5-L4-L3, the compound numbers are X-2-23-1 to X-2-23-3655,

[0196] When X-3-1 is replaced by X-2-24 in Ar3-L5-L4-L3, the compound numbers are X-2-24-1 to X-2-24-3655,

[0197] When X-3-1 is replaced by X-3-2 in Ar3-L5-L4-L3, the compound numbers are X-3-2-1 to X-3-2-3655,

[0198] When X-3-1 is replaced by X-3-3 in Ar3-L5-L4-L3, the compound numbers are X-3-3-1 to X-3-3-3655,

[0199] When X-3-1 is replaced by X-3-4 in Ar3-L5-L4-L3, the compound numbers are X-3-4-1 to X-3-4-3655,

[0200] When X-3-1 is replaced by X-3-5 in Ar3-L5-L4-L3, the compound numbers are X-3-5-1 to X-3-5-3655,

[0201] When X-3-1 is replaced by X-3-6 in Ar3-L5-L4-L3, the compound numbers are X-3-6-1 to X-3-6-3655,

[0202] When X-3-1 is replaced by X-3-7 in Ar3-L5-L4-L3, the compound numbers are X-3-7-1 to X-3-7-3655,

[0203] When X-3-1 is replaced by X-3-8 in Ar3-L5-L4-L3, the compound numbers are X-3-8-1 to X-3-8-3655,

[0204] When X-3-1 is replaced by X-3-9 in Ar3-L5-L4-L3, the compound numbers are X-3-9-1 to X-3-9-3655,

[0205] When X-3-1 is replaced by X-3-10 in Ar3-L5-L4-L3, the compound numbers are X-3-10-1 to X-3-10-3655,

[0206] When X-3-1 is replaced by X-3-11 in Ar3-L5-L4-L3, the compound numbers are X-3-11-1 to X-3-11-3655,

[0207] When X-3-1 is replaced by X-3-12 in Ar3-L5-L4-L3, the compound numbers are X-3-12-1 to X-3-12-3655,

[0208] When X-3-1 is replaced by X-3-13 in Ar3-L5-L4-L3, the compound numbers are X-3-13-1 to X-3-13-3655,

[0209] When X-3-1 is replaced by X-3-14 in Ar3-L5-L4-L3, the compound numbers are X-3-14-1 to X-3-14-3655,

[0210] When X-3-1 is replaced by X-3-15 in Ar3-L5-L4-L3, the compound numbers are X-3-15-1 to X-3-15-3655,

[0211] When X-3-1 is replaced by X-3-16 in Ar3-L5-L4-L3, the compound numbers are X-3-16-1 to X-3-16-3655,

[0212] When X-3-1 is replaced by X-3-17 in Ar3-L5-L4-L3, the compound numbers are X-3-17-1 to X-3-17-3655,

[0213] When X-3-1 is replaced by X-3-18 in Ar3-L5-L4-L3, the compound numbers are X-3-18-1 to X-3-18-3655,

[0214] When replacing X-3-1 with X-3-19 in Ar3-L5-L4-L3, the compound numbers are X-3-19-1 to X-3-19-3655.

[0215] When replacing X-3-1 with X-3-20 in Ar3-L5-L4-L3, the compound numbers are X-3-20-1 to X-3-20-3655.

[0216] When replacing X-3-1 with X-3-21 in Ar3-L5-L4-L3, the compound numbers are X-3-21-1 to X-3-21-3655.

[0217] When replacing X-3-1 with X-3-22 in Ar3-L5-L4-L3, the compound numbers are X-3-22-1 to X-3-22-3655.

[0218] When replacing X-3-1 with X-3-23 in Ar3-L5-L4-L3, the compound numbers are X-3-23-1 to X-3-23-3655.

[0219] When replacing X-3-1 with X-3-24 in Ar3-L5-L4-L3, the compound numbers are X-3-24-1 to X-3-24-3655.

[0220] Further, in an alternative embodiment of the present invention, the aromatic amine compound is selected from the following structures:

[0221]

[0222]

[0223]

[0224]

[0225] According to another aspect of the present invention, the present invention provides an application of the compound as an organic electroluminescent material.

[0226] An organic electroluminescent element includes a substrate, an anode, a hole transport region, a light-emitting layer, an electron transport region, and a cathode. The light-emitting layer is located between the anode and the cathode. The hole transport region is located between the anode and the light-emitting layer. The electron transport region is located between the light-emitting layer and the cathode. The hole transport region contains the aromatic amine compound of the present invention.

[0227] Preferably, the hole transport region includes a first hole transport layer and a second hole transport layer. The second hole transport layer is located between the first hole transport layer and the light-emitting layer. The second hole transport layer contains the aromatic amine compound of the present invention.

[0228] An electronic device includes one or more of a display, a monitor, and a lighting device, including the organic electroluminescent element described in the present invention; and a control unit for driving the above display device.

[0229] Generally speaking, compared with the prior art through the above technical solutions conceived by the present invention, the following beneficial effects can be achieved:

[0230] 1. For the arylamine compound of the present invention, when the compound with the specific parent nucleus structure of the present invention is used as an organic electroluminescent material, especially as a hole transport region material, excellent performance is exhibited. BRIEF DESCRIPTION OF THE DRAWINGS

[0231] Figure 1 It is a schematic structural diagram of the organic electroluminescent element described in Application Example 1; wherein: Figure 1 The numbers in it represent: 1. Substrate, 2. Anode, 3. Hole injection layer, 4. First hole transport layer, 5. Second hole transport layer, 6. Light emitting layer, 7. Hole blocking layer, 8. Electron transport layer, 9. Cathode.

[0232] Figure 2 It is a mass spectrometry (LC-MS) diagram of compound X-3-1-10 prepared in Synthesis Example 12 in the compound preparation examples. DETAILED DESCRIPTION OF THE EMBODIMENTS

[0233] Now, exemplary embodiments will be described in detail. Their examples are illustrated in the accompanying drawings, in which the same reference numerals always refer to the same elements. In this regard, the present exemplary embodiments may have different forms and should not be construed as limited to the descriptions set forth herein. Therefore, the exemplary embodiments are described below only by referring to the accompanying drawings for illustrative purposes. As used herein, the term "and / or" includes any and all combinations of one or more of the related listed items. Expressions such as "at least one (kind) of" modify the entire list of elements when before or after the list of elements and do not modify the individual elements of the list.

[0234] It will be understood that when an element is referred to as being "on" another element, it can be directly in contact with the other element or there can be intervening elements therebetween. In contrast, when an element is referred to as being "directly on" another element, there are no intervening elements.

[0235] It will be further understood that the terms "comprises" or "comprising", when used in this specification, indicate the presence of the stated features, regions, wholes, steps, operations, elements, and / or components, but do not preclude the presence or addition of one or more other features, regions, wholes, steps, operations, elements, components, and / or their combinations.

[0236] Unless otherwise defined, all terms (including technical and scientific terms) used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this general inventive concept belongs. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning consistent with their meaning in the relevant art and the context of this disclosure, and will not be interpreted in an idealized or overly formal sense unless clearly so defined herein.

[0237] The present invention will be further described below in conjunction with specific embodiments. It should be understood that these embodiments are only used to illustrate the present invention and not to limit the protection scope of the present invention. In addition, it should be understood that after reading the content disclosed in the present invention, those skilled in the art can make various changes or modifications to the present invention, and these equivalent forms also fall within the protection scope defined by the present invention.

[0238] Unless otherwise specified, the experimental methods used in the following embodiments are all conventional methods; unless otherwise specified, the reagents, materials, reaction raw materials, etc. used in the following embodiments can all be obtained from commercial channels.

[0239] The room temperature mentioned in the following embodiments is all 25 °C.

[0240] Term Explanation

[0241] As used in the present invention, "X-m-n", "Y1……Y85", "Y1……Y85" are the substituent numbers corresponding to Ar3-L5-L4-L3-, -L1-Ar1, -L2-Ar2 respectively. According to the substituents corresponding to this numbering, the compounds of the present application can be determined. For example, when m = 1 and n = 1, Ar3-L5-L4-L3- is selected from the substituent numbered "X-1-1" If at this time -L1-Ar1 is selected from the substituent numbered "Y1" -L2-Ar2 is selected from the substituent numbered "Y1" At this time, the corresponding compound number is X-1-1-1, and the compound structure is

[0242] As used in the present invention, represents the substitution position.

[0243] As used in the present invention, represents that the benzene ring in the group is fused to one of the phenyl groups on the carbazole on either side, and the fused group includes but is not limited to

[0244] As used in the present invention, the above-mentioned A1 selected from substituted or unsubstituted C6-C14 aromatic rings means derived from a combination of a single ring or two or more aromatic hydrocarbon rings, where the number of carbon atoms is the number of ring-forming atoms, excluding the number of carbon atoms in the substituents, and the number of ring-forming atoms includes the number of these two carbons, C1 and C2;

[0245] As used in the present invention, the above-mentioned A2 selected from substituted or unsubstituted C10-C14 aromatic rings means derived from a combination of a single ring or two or more aromatic hydrocarbon rings, where the number of carbon atoms is the number of ring-forming atoms, excluding the number of carbon atoms in the substituents, and the number of ring-forming atoms includes the number of these two carbons, C3 and C4.

[0246] As used in the present invention, the term "halogen group" may include fluorine, chlorine, bromine or iodine.

[0247] As used in the present invention, the abbreviation Bpin represents the group where represents the connection position.

[0248] As used in the present invention, the abbreviation Pd2(dba)3 represents the compound tris(dibenzylideneacetone)dipalladium.

[0249] As used in the present invention, the abbreviation Xphos represents the compound 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl.

[0250] As used in the present invention, the abbreviation Pd(dppf)Cl2 represents the compound dichloropalladium(II) 1,1′-bis(diphenylphosphino)ferrocene.

[0251] As used in the present invention, the abbreviation t-BuONa represents the compound sodium tert-butoxide.

[0252] As used in the present invention, the abbreviation SPhos represents the compound 2-bis(cyclohexylphosphino)-2′,6′-dimethoxybiphenyl.

[0253] As used in the present invention, the term "C6-C14 aromatic ring" means an aromatic hydrocarbon ring derived from a single ring or a combination of two or more rings and having 6 to 14 carbon atoms, which may be fused to adjacent rings, and the shared carbon atoms during fusion should also be included in the 6 to 14 carbon atoms. The term "C10-C14 aromatic ring" should be understood in the same way.

[0254] As used in the present invention, the term "C1-C10 alkyl" means a monovalent substituent derived from a straight-chain or branched-chain saturated hydrocarbon having 1 to 10 carbon atoms, and its examples include but are not limited to methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl and hexyl.

[0255] As used in the present invention, the term "C3-C10 cycloalkyl" refers to a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 10 carbon atoms. Examples of such cycloalkyls include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, norbornyl, adamantyl, etc.

[0256] As used in the present invention, the term "C2-C10 heterocycloalkyl" refers to a monovalent substituent derived from a monocyclic or polycyclic group having 2 to 10 carbon atoms and containing at least one heteroatom in the ring, said heteroatom being selected from O, S, N, P, Si.

[0257] As used in the present invention, the term "alkoxy" refers to a straight-chain, branched-chain or cyclic chain. The number of carbon atoms in the alkoxy is not particularly limited herein, but the alkoxy preferably has 1 to 10 carbon atoms. Specific examples thereof include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, benzyloxy.

[0258] As used in the present invention, the term "cycloalkenyl" refers to an unsaturated carbocyclic ring and does not have aromaticity.

[0259] As used in the present invention, the term "heterocycloalkenyl" refers to an unsaturated heterocyclic ring and does not have aromaticity.

[0260] As used in the present invention, the term "C6-C60 aryl" refers to a monovalent substituent derived from an aromatic hydrocarbon having a single ring or a combination of two or more rings and having 6 to 60 carbon atoms. Further, such aryl may have a form in which two or more of the rings are simply linked to each other or fused to each other. Examples of such aryls include, but are not limited to, phenyl, biphenyl, naphthyl, phenanthryl, anthryl, pyrenyl, triphenylenyl, fluoranthenyl, dimethyl 9,9-dimethylfluorene, 9,9-diphenylfluorene, spirobifluorene, etc.

[0261] As used in the present invention, the term "arylene" refers to a divalent aryl derived by removing one hydrogen atom from "aryl". For example, phenyl becomes phenylene by removing one hydrogen atom, and naphthyl becomes naphthylene by removing one hydrogen atom.

[0262] As used in the present invention, the term "heteroaryl having 3 to 60 carbon atoms" refers to a monovalent substituent derived from a monocyclic or polycyclic aromatic hydrocarbon having 3 to 60 carbon atoms. In this connection, at least one carbon atom, preferably 1 to 3 carbon atoms in the ring, is replaced by a heteroatom such as N, O, S, P, B or Si. In addition, such a heteroaryl may have a form in which two or more rings are simply linked to each other or fused to each other or fused to an aryl group. Examples of such heteroaryls include pyrrolyl, furyl, thienyl, benzofuryl, benzothienyl, carbazolyl, dibenzofuryl, dibenzothienyl, etc., but the present invention is not limited thereto.

[0263] As used in the present invention, the term "heteroarylene" refers to a divalent heteroaryl derived by removing one hydrogen atom from "heteroaryl", for example, pyridyl becomes pyridylene after removing one hydrogen atom.

[0264] As used in the present invention, "aromatic amine" includes arylamine, heteroarylamine, arylheteroarylamine.

[0265] As used in the present invention, "K group having M - N carbon atoms" or "K group of C(M - N)" in the expression "carbon atoms of M - N" means the number of carbon atoms of the K group when it is unsubstituted, excluding the carbon atoms of the substituents when it is substituted. For example, an aryl group of C6 - C60 means that when it is unsubstituted, the number of carbon atoms in the aryl group is any integer from 6 to 60, that is, the number of carbon atoms when unsubstituted can be 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20... 60.

[0266] As used in the present invention, the term "substituted" means that a hydrogen atom in a compound is replaced by another substituent. The position where substitution occurs can be the position where the hydrogen atom is replaced. That is, this position is not limited to a specific position, as long as the hydrogen at this position can be replaced by a substituent. For example, carbazolyl, as long as not otherwise specified in this specification, includes any of the following groups, but is not limited thereto.

[0267] "Unsubstituted" means retaining a hydrogen atom, in which case the hydrogen atom includes protium, deuterium, and tritium, and the substituted case may also include the case of deuterium or tritium substitution.

[0268] When there are two or more substituents, the two or more substituents may be the same or different.

[0269] As used in the present invention, the term "terphenyl" includes

[0270] As used in the present invention, hydrogen atoms include protium, deuterium, and tritium. The compounds described in the present invention may contain deuterium atoms of natural origin, or deuterium atoms may be introduced by deuterating a part or all of the starting compounds. When deuterium atoms are introduced from the starting materials, the deuteration rate may be 100%, or less than 100%, or less than 95%, or less than 90%, or less than 80%. The deuteration rate may also be 1% or more, or 5% or more, or 10% or more. When the deuteration rate is not 100%, it means a mixture of deuterated compounds and non-deuterated compounds, or a mixture of fully deuterated compounds and partially deuterated compounds, or a mixture of fully deuterated compounds, non-deuterated compounds, and partially deuterated compounds.

[0271] As used in the present invention, terms such as the first, the second, A, B, etc. are used. The above terms are only used to distinguish the components and do not limit the essence or order of the components corresponding to the terms.

[0272] Organic electroluminescent element

[0273] The structure of the organic electroluminescent element of the present invention is a publicly known structure, which includes an anode, a cathode, and an organic layer located between the anode and the cathode. The organic layer includes a light-emitting layer, and at least one layer of the organic layer contains the compound of the present invention.

[0274] The organic layer may further include one or more of a hole injection layer, a hole transport layer, a second hole transport layer, a hole blocking layer, an electron transport layer, and an electron injection layer, but is not limited thereto.

[0275] The light-emitting element of the present invention may be fluorescent light-emitting, phosphorescent light-emitting, or a combination thereof. The light-emitting element may be a single light-emitting element or a tandem type of multiple light-emitting units.

[0276] As simple light-emitting elements, the following can be cited, but are not limited thereto.

[0277] (1) Hole transport layer / fluorescent light-emitting layer / electron transport layer;

[0278] (2) Hole transport layer / phosphorescent light-emitting layer / electron transport layer;

[0279] (3) Hole transport layer / first fluorescent light-emitting layer / second fluorescent light-emitting layer / electron transport layer;

[0280] (4) Hole transport layer / first phosphorescent light-emitting layer / second phosphorescent light-emitting layer / electron transport layer;

[0281] (5) Hole transport layer / fluorescent light-emitting layer / spacer layer / phosphorescent light-emitting layer / electron transport layer;

[0282] (6) Hole transport layer / second hole transport layer / fluorescent light-emitting layer / electron transport layer;

[0283] (7) Hole transport layer / Second hole transport layer / Fluorescent emission layer / Hole blocking layer / Electron transport layer;

[0284] (8) Hole transport layer / Second hole transport layer / Phosphorescent emission layer / Electron transport layer;

[0285] (9) Hole transport layer / Second hole transport layer / Phosphorescent emission layer / Hole blocking layer / Electron transport layer;

[0286] (10) Hole injection layer / Hole transport layer / Phosphorescent emission layer / Electron transport layer / Electron injection layer;

[0287] (11) Hole injection layer / Hole transport layer / Fluorescent emission layer / Electron transport layer / Electron injection layer;

[0288] (12) Hole injection layer / Hole transport layer / Second hole transport layer / Phosphorescent emission layer / Electron transport layer / Electron injection layer;

[0289] (13) Hole injection layer / Hole transport layer / Second hole transport layer / Fluorescent emission layer / Electron transport layer / Electron injection layer;

[0290] The above-mentioned phosphorescent / fluorescent emission layers can each emit light of different colors.

[0291] As a tandem organic electroluminescent device, it can be an anode / First light-emitting unit / Intermediate layer / Second light-emitting unit / Cathode. The intermediate layer can generally also be referred to as a charge generation layer, an electron extraction layer, a connection layer, etc. For example, when stacking a fluorescent emission layer and a phosphorescent emission layer, in order to prevent the excitons generated in the phosphorescent emission layer from diffusing to the fluorescent emission layer, or to adjust the carrier balance, an intermediate layer is placed between the fluorescent emission layer and the phosphorescent emission layer.

[0292] When the organic light-emitting device includes a plurality of organic material layers, the organic material layers can be formed of the same material or different materials.

[0293] The organic electroluminescent device of the present specification can be manufactured by materials and methods known in the art, except that one or more of the organic material layers are formed by using the compounds described in the present invention.

[0294] As the anode material, a material with a relatively large work function can be used, and transparent conductive oxides, metals, conductive polymers, etc. can be used. Specific examples of the anode material include: metals such as vanadium, chromium, copper, zinc, and gold, or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, etc., but not limited thereto.

[0295] As the cathode material, a material with a low work function is usually used to facilitate electron injection into the organic layer, and metals, metal oxides, conductive polymers, etc. can be used. Specific examples of the cathode material include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or their alloys; multi-layered structure materials such as LiF / Al or LiO2 / Al, etc., but not limited thereto.

[0296] The hole injection layer is a layer that injects holes from the electrode and has the ability to transport holes. In order to reduce the energy level difference between the electrodes, the hole injection layer is mainly prepared based on aromatic amine compounds, and can also be prepared with the following materials. For example, copper phthalocyanine is selected from metal complexes, and HATCN (2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene) with a phenylene structure is selected from materials with the lowest unoccupied molecular orbital energy level. When used as a light-emitting host and a dopant, F4-TCNQ (2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanoquinodimethane) derivatives with the lowest unoccupied molecular orbital energy level can be doped in the aromatic amine compounds.

[0297] The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer, and the hole transport material can appropriately be a material with a high hole mobility that can receive holes from the anode or the hole injection layer and transfer the holes to the light-emitting layer. Arylamine-based derivatives, triphenyl diamine derivatives, etc. can be used, and low-molecular or high-molecular materials can also be used.

[0298] The second hole transport layer can adjust the energy level difference between the hole transport region and the light-emitting layer, facilitating the entry of holes into the light-emitting layer, and at the same time reducing the probability of electrons entering the hole transport region from the light-emitting layer. Commonly used ones are aromatic amine-based derivatives.

[0299] A luminescent material is a material that can receive holes and electrons from a hole transport layer and an electron transport layer respectively, and combine the holes and electrons to emit light in the visible light region. The luminescent layer material includes a host material and a dopant material. Red, green, or blue luminescent materials can be used, and if necessary, two or more luminescent materials can be mixed. As the luminescent material, a fluorescent material can be used, or a phosphorescent material can also be used. As the luminescent material, a single-component material can be adopted, or a multi-component material can also be adopted.

[0300] An electron transport layer is a layer that receives electrons from an electron injection layer and transports the electrons to the luminescent layer, and the electron transport material is a material with high electron mobility that can receive electrons from the cathode and transfer the electrons to the luminescent layer. Metal complexes such as triazine derivatives, oxadiazole derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, fluorenone derivatives, diphenyl dicyanoethylene and its derivatives, 8-hydroxyquinoline and its derivatives, etc. can be used, and polymer materials and small molecule materials can also be used.

[0301] An electron injection layer is a layer that injects electrons from an electrode.

[0302] According to the materials used, the organic light-emitting device of the present specification can be a top-emitting device, a bottom-emitting device, or a double-emission device.

[0303] A charge generation layer refers to an intermediate layer located between the anode and the cathode in a tandem structure device, and is a layer that generates holes and electrons by charge separation. The charge generation layer is usually formed by a P-type layer on the cathode side and an N-type layer on the anode side, and can effectively separate charges and efficiently transport carriers.

[0304] In one embodiment of the present invention, the formation method of each layer is not particularly limited. Formation methods based on vacuum evaporation, spin coating, etc., which are well-known in the past, can be used. Each layer such as the luminescent layer can be formed by a well-known method such as vacuum evaporation, molecular beam epitaxy (MBE method), or coating methods such as dipping, spin coating, casting, bar coating, roll coating, etc. of a solution dissolved in a solvent.

[0305] In one embodiment of the present invention, the film thickness of each layer is not particularly limited, and generally several nanometers to several hundred nanometers can be adopted. In order to suppress defects such as pinholes, reduce the driving voltage, and improve the luminous efficiency, a range of several nm to 1 μm is usually preferred.

[0306] Those skilled in the art can synthesize the compounds of the present invention by referring to the synthesis of the following compounds and well-known synthesis methods. There are various synthesis methods for the compounds of the present invention, and the following methods are only for illustration.

[0307] LC-MS brand: Waters, model: SQ Detector 2

[0308] Nuclear magnetic resonance brand: Bruker, model: AVANCE NEO 400

[0309] Those skilled in the art can synthesize the compounds of the present invention with reference to the synthesis of the following compounds and well-known synthesis methods. An exemplary synthesis general formula of the present invention is as follows:

[0310] Synthesis general formula 1:

[0311]

[0312] Synthesis general formula 2:

[0313]

[0314] Among them, X and Y are each independently a halogen (including F, Cl, Br, I), and those skilled in the art can select according to the selectivity of the reaction;

[0315] A1, A2, L1-L5, Ar1, Ar2 refer to the definitions in the above embodiments;

[0316] Bpin is Indicates the connection position.

[0317] Synthesis of intermediates

[0318] 1. Synthesis of intermediate 1:

[0319] Step 1: Synthesis of intermediate 1-1

[0320]

[0321] Under a nitrogen atmosphere, 7H-benzo[c]carbazole (15.0 g, 69.04 mmol), 1-bromo-2-fluorobenzene (48.3 g, 276.15 mmol), and cesium carbonate (22.5 g, 207.12 mmol) were added to a 500 mL four-necked flask, 200 mL of N,N-dimethylformamide was added, and the mixture was stirred at 140 °C for 6 h. After the reaction was completed, heating was stopped. The mixture was extracted and separated with dichloromethane and water, the organic phase was dried by evaporation and stirred for sampling, and the sample was purified by column chromatography (volume ratio of n-hexane:dichloromethane = 30:1) to obtain 10.0 g of intermediate 1-1 with a yield of 40%.

[0322] LC-MS (APCI): 372.11 [M+H] +

[0323] Step 2: Synthesis of intermediate 1

[0324]

[0325] Under a nitrogen atmosphere, intermediate 1-1 (5.0 g, 13.43 mmol), 2-(1-chlorodibenzo[b,d]furan-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (4.4 g, 13.43 mmol), tetrakis(triphenylphosphine)palladium (310 mg, 0.27 mmol), and potassium carbonate (5.6 g, 40.29 mmol) were added to a 250 mL four-necked flask. 90 mL of tetrahydrofuran (THF) and 30 mL of deionized water were added, and the reaction system was heated to reflux, followed by stirring at a constant temperature for 6 h. The mixture was extracted and separated with ethyl acetate and water. The organic phase was evaporated to dryness and stirred, and the sample was purified by column chromatography (volume ratio of n-hexane:dichloromethane = 10:1) to obtain 4.2 g of intermediate 1, with a yield of 63%.

[0326] LC-MS (APCI): 494.26 [M+H] +

[0327] 2. Synthesis of intermediate 2

[0328] Step 1: Synthesis of intermediate 2-1

[0329]

[0330] Under a nitrogen atmosphere, 2,3-benzo[c]carbazole (15.0 g, 69.038 mmol), 1-bromo-2-fluorobenzene (48.3 g, 276.154 mmol), and cesium carbonate (22.5 g, 207.115 mmol) were added to a 500 mL four-necked flask. 200 mL of N,N-dimethylformamide was added, and the mixture was stirred at 140 °C for 6 h. Heating was stopped after the reaction was completed. The mixture was extracted and separated with dichloromethane and water. The organic phase was evaporated to dryness and stirred, and the sample was purified by column chromatography (n-hexane:dichloromethane = 30:1) to obtain 12 g of intermediate 2-1, with a yield of 46%.

[0331] LC-MS (APCI): 372.11 [M+H] +

[0332] Step 2: Synthesis of intermediate 2

[0333]

[0334] Under a nitrogen atmosphere, the intermediate 2-1 (5.0 g, 13.431 mmol), 2-(1-chlorodibenzo[b,d]furan-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (4.4 g, 13.431 mmol), tetrakis(triphenylphosphine)palladium (310 mg, 0.268 mmol), and potassium carbonate (5.6 g, 40.293 mmol) were added to a 250 mL four-necked flask. 90 mL of tetrahydrofuran (THF) and 30 mL of deionized water were added, and the reaction system was heated to reflux, followed by stirring at a constant temperature for 6 h. After the reaction was completed, extraction and liquid separation were carried out with ethyl acetate and water. The organic phase was rotary evaporated and mixed with samples, and the sample was purified by column chromatography (volume ratio of n-hexane:dichloromethane = 10:1) to obtain 4.4 g of intermediate 2, with a yield of 66%.

[0335] LC-MS(APCI): 494.26[M+H] +

[0336] Synthesis Examples:

[0337] Synthesis Example 1: Synthesis of Compound X-2-1-56

[0338]

[0339] Under a nitrogen atmosphere, the intermediate 2 (5 g, 10.1 mmol), 4-(4-dibenzofuranyl)-N-phenylaniline (3.4 g, 10.1 mmol), t-BuONa (1.9 g, 20.2 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (0.25 g, 0.6 mmol), and tris(dibenzylideneacetone)dipalladium (0.27 g, 0.3 mmol) were added to a four-necked reaction flask. Then 50 mL of toluene was added, and the reaction system was heated to reflux. After the reaction was completed in 2 h, the reaction solution was cooled to room temperature, 100 mL of water was added, and extraction was carried out with dichloromethane. The organic phase was concentrated and rotary evaporated, and then purified by refluxing and slurrying with 60 mL of ethanol to obtain Compound X-2-1-56 (4.8 g, yield 60%) as the final product.

[0340] LC-MS(APCI): 793.43[M+H] +

[0341] 11H NMR (400 MHz, CD2Cl2) δ 8.29 (s, 1H), 7.95 (ddd, 3H), 7.91–7.87 (m, 1H), 7.84 (dd, 1H), 7.82–7.78 (m, 1H), 7.74–7.66 (m, 2H), 7.59–6.94 (m, 19H), 6.87–6.78 (m, 2H), 6.72 (d, 1H), 6.64–6.52 (m, 5H).

[0342] Synthesis Example 2: Synthesis of Compound X-2-5-56

[0343] 1. Synthesis of Intermediate T2-1

[0344]

[0345] Under a nitrogen atmosphere, 2,3-benzo[c]carbazole (15.0 g, 69.038 mmol), 1-bromo-3-fluorobenzene (48.3 g, 276.154 mmol), and cesium carbonate (22.5 g, 207.115 mmol) were added to a 500 mL four-necked flask. 200 mL of N,N-dimethylformamide was added, and the mixture was stirred at 140 °C for 6 h. After the reaction was completed, heating was stopped. The mixture was extracted and separated with dichloromethane and water. The organic phase was dried by rotary evaporation and mixed with a sample, and the sample was purified by column chromatography (volume ratio: n-hexane:dichloromethane = 30:1) to obtain 14 g of Intermediate T2-1 with a yield of 54%.

[0346] LC-MS (APCI): 372.11 [M+H] +

[0347] 2. Synthesis of Intermediate T2-2

[0348]

[0349] Under a nitrogen atmosphere, Intermediate T2-1 (5.0 g, 13.431 mmol), 2-(1-chlorodibenzo[b,d]furan-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (4.4 g, 13.431 mmol), tetrakis(triphenylphosphine)palladium (310 mg, 0.268 mmol), and potassium carbonate (5.6 g, 40.293 mmol) were added to a 250 mL four-necked flask. 90 mL of THF and 30 mL of deionized water were added, and the reaction system was heated to reflux and then stirred at a constant temperature for 6 h. The mixture was extracted and separated with ethyl acetate and water. The organic phase was dried by rotary evaporation and mixed with a sample, and the sample was purified by column chromatography (volume ratio: n-hexane:dichloromethane = 10:1) to obtain 5.3 g of Intermediate T2-2 with a yield of 80%.

[0350] LC-MS (APCI): 494.26 [M+H]+

[0351] 3. Synthesis of Compound X-2-5-56

[0352]

[0353] Under a nitrogen atmosphere, intermediate T2-2 (5 g, 10.1 mmol), intermediate T2-a (3.4 g, 10.1 mmol), t-BuONa (1.9 g, 20.2 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (0.25 g, 0.6 mmol) and tris(dibenzylideneacetone)dipalladium(0) (0.27 g, 0.3 mmol) were added into a four-necked reaction flask. Then 50 mL of toluene was added, and the temperature was raised to reflux. After the reaction was completed in 2 h, the reaction solution was cooled to room temperature, 100 mL of water was added, and the mixture was extracted with dichloromethane. The organic phase was concentrated and dried by rotary evaporation, and then purified by refluxing and pulping with 60 mL of ethanol to obtain compound X-2-5-56 (5.6 g, yield 70%) as the final product.

[0354] LC-MS (APCI): 793.43 [M+H] +

[0355] 1 H NMR (400 MHz, Methylene Chloride-d2) δ8.58 (s, 1H), 8.30–8.20 (m, 2H), 8.04–7.96 (m, 2H), 7.94–7.89 (m, 2H), 7.88–7.82 (m, 2H), 7.81–7.75 (m, 3H), 7.68 (dd, 2H), 7.59 (d, 1H), 7.55–7.44 (m, 4H), 7.43–7.32 (m, 5H), 7.31–7.23 (m, 3H), 7.23–7.14 (m, 7H), 7.06–6.94 (m, 2H).

[0356] Synthesis Example 3: Synthesis of Compound X-3-1-28

[0357]

[0358] Under a nitrogen atmosphere, N-[4-(1-naphthyl)phenyl]-phenyl-4-amine (4 g, 13.5 mmol), Intermediate 1 (7 g, 14.2 mmol), Pd2dba3 (0.25 g, 0.27 mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (0.26 g, 0.54 mmol), and sodium tert-butoxide (2.6 g, 27.1 mmol) were added to a four-necked reaction flask. Then, 50 ml of toluene was added, and the temperature was raised to 110 °C for reaction. After the reaction was completed, the reaction solution was cooled to room temperature, extracted with dichloromethane, and dried over anhydrous sodium sulfate, followed by removal of the solvent. Purification was carried out by column chromatography (development solvent volume ratio: n-hexane:dichloromethane = 3:1). Thus, Compound X-3-1-28 (9 g, yield 88%) was obtained as the final product.

[0359] LC-MS(APCI): 753.41[M+H] +

[0360] 1 H NMR(400MHz,Methylene Chloride-d2)δ8.52(d,1H),8.36–8.24(m,1H),8.00–7.89(m,1H),7.88–7.64(m,7H),7.55–7.16(m,11H),7.12–6.76(m,10H),6.70–6.56(m,4H),6.50(d,1H).

[0361] Synthesis Example 4: Synthesis of Compound X-3-1-277

[0362]

[0363] Under a nitrogen atmosphere, N-(4-(naphthalen-1-yl)phenyl)-[1,1'-biphenyl]-4-amine (7 g, 18.8 mmol), Intermediate 1 (8.2 g, 16.6 mmol), Pd2(dba)3 (0.5 g, 0.54 mmol), sodium tert-butoxide (3.6 g, 37 mmol), Xphos (0.46 g, 1.1 mmol), and 140 ml of toluene were added to a reaction flask, and the reaction was carried out at 90 °C for 4 h. After the reaction was completed, the reaction solution was extracted with dichloromethane, dried over anhydrous sodium sulfate, and the solvent was removed. Crystallization with ethyl acetate (purification) was carried out. Thus, Compound X-3-1-277 (12 g, yield: 77%) was obtained as the final product.

[0364] LC-MS(APCI): 830.50[M+H] +

[0365] 1H NMR(400MHz,Methylene Chloride-d2)δ8.54(d,1H),8.36–8.27(m,1H),8.01–7.92(m,1H),7.85–7.65(m,7H),7.53–7. 17(m,16H),7.16–7.00(m,6H),6.91(d,1H),6.88–6.81(m,2H),6.75–6.62(m,4H),6.55(d,1H).

[0366] Synthesis Example 5: Synthesis of Compound X-3-2-26

[0367] 1. Synthesis of intermediate T5-1

[0368]

[0369] In a 500ml four-necked bottle, 4-bromo-1-chlorodibenzo[b,d]furan (10.0g, 35.52mmol), 3-(naphthalene-2-yl)-N-phenylaniline (10.5g, 35.52mmol), sodium tert-butoxide (6.8g, 71.04mmol), Pd2(dba)3 (650mg, 0.71mmol), tri-tert-butylphosphine (570mg, 2.84mmol), toluene (200ml) were added in sequence, and refluxed for 3 hours under nitrogen protection. After the reaction was completed, column chromatography (n-hexane: dichloromethane = 10:1) was performed to obtain intermediate T5-1 (14.7g, yield 83.7%).

[0370] LC-MS:496.30[M+H] +

[0371] 2. Synthesis of compound X-3-2-26

[0372]

[0373] Into a 500ml four-necked flask, add intermediate T5-1 (14.7g, 29.75mmol), (2-(7H-benzo[c]carbazole-7-yl)phenyl)boric acid (10.0g, 29.75mmol), Pd(dppf)Cl2 (435mg, 0.595mmol), potassium carbonate (8.2g, 59.5mmol), toluene (150ml), ethanol (50ml), water (50ml), and reflux for 6 hours under nitrogen protection. After the reaction is completed, column chromatography (n-hexane: dichloromethane = volume ratio 5:1) is performed to obtain compound X-3-2-26 (18.7g, yield: 83.4%) as the final product.

[0374] LC-MS: 753.41[M+H]+

[0375] 1 H NMR(400 MHz, Methylene Chloride-d2) δ 8.73 (d, 1H), 8.55 (d, 1H), 8.01 (qt, 3H), 7.92–7.73 (m, 15H), 7.34–7.20 (m, 7H), 7.08–6.90 (m, 5H), 6.55–6.38 (m, 4H).

[0376] Synthesis Example 6: Synthesis of Compound X-3-1-88

[0377]

[0378] Under a nitrogen atmosphere, N-(4-biphenylyl)-2-biphenylamine (6 g, 18.6 mmol), Intermediate 1 (9.2 g, 18.6 mmol), Pd2(dba)3 (0.5 g, 0.54 mmol), sodium tert-butoxide (3.6 g, 37 mmol), Xphos (0.46 g, 1.1 mmol), and 140 ml of toluene were added to a reaction flask, and the reaction was carried out at 90 °C for 4 h. After the reaction was completed, the reaction solution was extracted with dichloromethane, dried over anhydrous sodium sulfate, and the solvent was removed. Crystallization (purification) was carried out with ethyl acetate. Thus, Compound X-3-1-88 as the final product (12 g, yield: 82%) was obtained.

[0379] LC-MS(APCI): 779.98 [M+H] +

[0380] 1 H NMR(400 MHz, Methylene Chloride-d2) δ 8.56 (s, 1H), 8.31 (s, 1H), 7.82 (d, 2H), 7.69 (s, 3H), 7.57 (s, 2H), 7.39 (s, 15H), 6.95 (s, 1H), 6.83 (s, 4H), 6.65 (s, 3H), 6.52 (s, 1H), 6.43 (s, 3H), 6.27 (s, 1H), 5.71 (s, 1H).

[0381] Synthesis Example 7: Synthesis of Compound X-3-1-283

[0382] 1. Synthesis of Intermediate T7-1

[0383]

[0384] Under nitrogen environment, 9-(3-chlorophenyl)phenanthrene (15g, 51.9mmol), 4-aminobiphenyl (9.7g, 57.3mmol), sodium tert-butoxide (9.9g, 103mmol), tris(dibenzylideneacetone)dipalladium (0.95g, 1mmol) and 2-dicyclohexylphosphine-2′,6′-dimethoxy-biphenyl (0.85g, 2mmol) were added to a four-necked reaction bottle, and then anhydrous toluene (125ml) solvent was added, and the mixture was heated to 110°C. When the reaction was completed, the mixture was cooled to room temperature, and 100ml of water was added to quench the reaction. The reaction liquid was extracted with 100ml of dichloromethane, and the organic phase was washed with water three times, dried and filtered with anhydrous sodium sulfate, and the organic phase was spin-dried to obtain 21.3g of a viscous solid. The mixture was separated by column chromatography, and the eluent was n-hexane:ethyl acetate = volume ratio 20:1. 15 g of crude product T7-1 was obtained, and then refluxed with ethanol:ethyl acetate = 5:1 to obtain intermediate T7-1 (14 g, yield 63.9%).

[0385] LC-MS (APCI): 422.44 [M+H] +

[0386] 2. Synthesis of compound X-3-1-283

[0387]

[0388] Under nitrogen environment, intermediate T7-1 (6g, 12.1mmol), intermediate 1 (4.7g, 11.1mmol), sodium tert-butoxide (1.95g, 20.2mmol), tris(dibenzylideneacetone)dipalladium (0.95g, 0.2mmol) and tri-tert-butylphosphine (0.85g, 2mmol) were added to a four-mouth reaction bottle, and then anhydrous toluene (125ml) solvent was added, heated to 110°C, and the heating was stopped after the reaction was completed, and the temperature was cooled to room temperature, 100ml of water was added to quench the reaction, and 100ml of dichloromethane was used to extract the reaction liquid. The organic phase was washed with water three times, dried and filtered with anhydrous sodium sulfate, and the organic phase was spin-dried to obtain 15g of black solid. Column chromatography separation, eluent n-hexane: dichloromethane = volume ratio 10:1, obtained as the final product Compound X-3-1-283 (8.3g, yield 78.3%).

[0389] LC-MS (APCI): 880.65 [M+H] +

[0390] 11H NMR (400 MHz, Methylene Chloride-d2) δ 8.63 (ddd, 2H), 8.14 (s, 1H), 7.94–7.87 (m, 1H), 7.84–7.62 (m, 6H), 7.61–7.38 (m, 9H), 7.34–7.28 (m, 2H), 7.27–7.17 (m, 6H), 7.15–7.06 (m, 3H), 7.06–6.74 (m, 8H), 6.68–6.51 (m, 4H).

[0391] Synthesis Example 8: Synthesis of Compound X-3-1-11

[0392]

[0393] Under a nitrogen atmosphere, N-phenyl[1,1′:3′,1′-terphenyl]-3-amine (4.95 g, 0.015 mol), Intermediate 1 (7.61 g, 0.015 mol), palladium acetate (0.093 g, 0.42 mmol), XPhos (0.40 g, 0.83 mmol), and sodium tert-butoxide (2.96 g, 0.031 mol) were added to a four-necked reaction flask. 120 ml of toluene was added, and the mixture was refluxed for 2 hours. The reaction solution was cooled to room temperature, quenched with water, extracted with dichloromethane, and the organic phase was concentrated and passed through a chromatography column. The eluent was n-hexane:dichloromethane = 3:1 (v / v). Compound X-3-1-11 (5.1 g, yield 43%) was obtained as a white solid.

[0394] LC-MS (APCI): 779.61 [M+H] +

[0395] 1 1H NMR (400 MHz, DMSO-d6) δ 8.61 (d, 1H), 8.51–8.37 (m, 1H), 8.08–7.90 (m, 3H), 7.89–7.78 (m, 3H), 7.72–6.80 (m, 26H), 6.73–6.61 (m, 1H), 6.56–6.26 (m, 3H).

[0396] Synthesis Example 9: Synthesis of Compound X-3-1-59

[0397]

[0398] Under a nitrogen atmosphere, 4-(dibenzo[b,d]thiophen-4-yl)-N-phenylaniline (5.6 g, 15.95 mmol), Intermediate 1 (15.19 g, 15.19 mmol), tetrakis(triphenylphosphine)palladium (346 mg, 0.30 mmol), and sodium tert-butoxide (2.9 g, 30.4 mmol) were added to a four-necked reaction flask. Then, 150 ml of toluene was added, and the temperature was raised to reflux for 4 hours. After the reaction was completed, filtration was carried out. The filter cake was washed with water and then refluxed and slurried with 100 ml of ethyl acetate for 30 minutes. After filtration, Compound X-3-1-59 as the final product was obtained (9.6 g, yield 77%).

[0399] LC-MS(APCI): 811.59[M+H] +

[0400] 1 H NMR(400MHz, Methylene Chloride-d2)δ8.37(s,1H),8.26–8.19(m,1H),8.15(dd,1H),8.07–8.01(m,2H),8.00–7.94(m,1H),7.89(dt,2H),7.78(qd,2H),7.60–7.38(m,8H),7.35–6.99(m,10H),6.97–6.87(m,2H),6.82(d,1H),6.75–6.70(m,2H),6.64(t,3H).

[0401] Synthesis Example 10: Synthesis of Compound X-2-5-28

[0402]

[0403] Under a nitrogen atmosphere, Intermediate T2-2 (5.0 g, 10.1 mmol), N-[4-(1-naphthyl)phenyl]-phenyl-4-amine (3.2 g, 11.4 mmol), t-BuONa (3 g, 21 mmol), Pd2(dba)3 (0.37 g, 0.4 mmol), and 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (0.8 g, 2.0 mmol) were added to a four-necked reaction flask. Then, 50 mL of toluene was added, and the temperature was raised to reflux by heating. After the reaction was completed in 2 h, the reaction solution was cooled to room temperature and passed through a flash column with toluene to obtain Compound X-2-5-28 as the final product (5 g, yield 68%).

[0404] LC-MS(APCI): 753.48[M+H] +

[0405] 11H NMR (400 MHz, Methylene Chloride-d2) δ 8.56 (s, 1H), 8.25–8.20 (m, 2H), 8.01–7.93 (m, 2H), 7.88 (s, 1H), 7.83 (ddd, 2H), 7.81–7.76 (m, 1H), 7.75–7.71 (m, 2H), 7.67–7.62 (m, 2H), 7.56 (dt, 1H), 7.50–7.12 (m, 20H), 7.03 (td, 1H), 6.96 (tt, 1H).

[0406] Synthesis Example 11: Synthesis of Compound X-3-1-78

[0407]

[0408] Under a nitrogen atmosphere, intermediate 1 (5.0 g, 10.1 mmol), intermediate T11-1 (3.4 g, 10.1 mmol), t-BuONa (1.9 g, 20.2 mmol), 2-bis(cyclohexylphosphino)-2',6'-dimethoxybiphenyl (0.4 g, 1.0 mmol) and tris(dibenzylideneacetone) dipalladium (0.18 g, 0.2 mmol) were added to a four-necked reaction flask. Then 50 mL of toluene was added and the mixture was heated to reflux. After the reaction was completed in 3 h, the reaction solution was cooled to room temperature, 100 mL of water was added, and the mixture was extracted with dichloromethane. The organic phase was concentrated and dried by rotary evaporation, and then purified by refluxing and pulping with a mixed solvent of 30 mL of ethyl acetate and 30 mL of ethanol to obtain compound X-3-1-78 (4.3 g, yield 53%) as the final product.

[0409] LC-MS (APCI): 793.50 [M+H] + .

[0410] 1 1H NMR (400 MHz, Methylene Chloride-d2) δ 8.33 (d, 1H), 8.26–8.18 (m, 1H), 8.02–7.91 (m, 1H), 7.83–7.67 (m, 4H), 7.54–7.30 (m, 6H), 7.28–7.18 (m, 4H), 7.16–6.86 (m, 11H), 6.85–6.69 (m, 5H), 6.56 (d, 1H), 6.47 (d, 2H).

[0411] Synthesis Example 12: Synthesis of Compound X-3-1-10

[0412] 1. Synthesis of Intermediate T12-1

[0413]

[0414] 4-Bromo-N-phenylaniline (12.00 g, 0.0483 mol) and 3-biphenylboronic acid (11.49 g, 0.0582 mol) were successively added into a 2 L four-necked flask, followed by potassium carbonate (6.68 g, 0.0725 mol), bis(triphenylphosphine)palladium(II) dichloride (0.68 g, 0.967 mmol). Then, tetrahydrofuran (120 ml) and water (30 ml) were added. The reaction was carried out at 75 °C for 15 h under nitrogen protection. After the reaction was completed, the temperature was lowered to 25 °C, and the reaction was quenched with water. The organic phase was separated by liquid separation, and the organic phase was dried by rotary evaporation. The intermediate T12-1 (9.5 g, yield 61.1%) was obtained by recrystallization from ethyl acetate.

[0415] LC-MS (APCI): 322.57 [M+H] + .

[0416] 2. Synthesis of compound X-3-1-10

[0417]

[0418] The intermediate T12-1 (4.5 g, 0.014 mol), intermediate 1 (8.3 g, 0.017 mol), potassium carbonate (2.69 g, 0.028 mol), tris(dibenzylideneacetone)dipalladium(0) (0.13 g, 0.14 mmol) and 2-(dicyclohexylphosphino)-2′,6′-dimethoxybiphenyl (0.23 g, 0.556 mmol) were successively added into a 250 ml four-necked flask, and then toluene (100 ml) was added. The reaction was carried out at 95 °C for 16 h under nitrogen protection. After the reaction was completed, the temperature was lowered to 25 °C, and the reaction was quenched with water. The organic phase was separated by liquid separation, and the organic phase was dried by rotary evaporation. The compound X-3-1-10 (3.5 g, yield 32.0%) as the final product was obtained by trituration with ethyl acetate.

[0419] LC-MS (APCI): 779.58 [M+H] + ; The corresponding mass spectrum is shown in the attached Figure 2 .

[0420] 11H NMR (400 MHz, Methylene Chloride-d2) δ 8.54 (dd, 1H), 8.35–8.26 (m, 1H), 7.96–7.87 (m, 1H), 7.81 (dd, 1H), 7.73–7.64 (m, 3H), 7.63–7.54 (m, 3H), 7.52–7.33 (m, 9H), 7.32–7.18 (m, 6H), 7.12–7.02 (m, 3H), 7.01–6.89 (m, 3H), 6.85 (d, 1H), 6.82–6.75 (m, 3H), 6.68–6.60 (m, 2H), 6.53–6.47 (m, 2H), 6.44 (d, 1H).

[0421] Synthesis Example 13: Synthesis of Compound X-3-1-9

[0422] 1. Synthesis of Intermediate T13-2

[0423]

[0424] Under nitrogen protection, Intermediate T13-1 (6 g, 12.3 mmol), aniline (2.2 g, 12.6 mmol), t-BuONa (2.5 g, 24.9 mmol), 2-bis(cyclohexylphosphino)-2',6'-dimethoxybiphenyl (0.4 g, 1.0 mmol) and tris(dibenzylideneacetone) dipalladium (0.18 g, 0.2 mmol) were added into a four-necked reaction flask. 60 mL of toluene was added and the temperature was raised to reflux. After the reaction was completed in 2 h, the reaction solution was cooled to room temperature, and the organic phase was extracted with dichloromethane. The organic phase was dried by rotary evaporation and purified by column chromatography (n-hexane:dichloromethane = 5:1) to obtain Intermediate T13-2 (6.2 g, yield 88%).

[0425] LC-MS (APCI): 322.30 [M+H] + .

[0426] 2. Synthesis of Compound X-3-1-9

[0427]

[0428] Under nitrogen protection, intermediate T13-2 (5.0 g, 13.2 mmol), intermediate 1 (3.6 g, 13.6 mmol), t-BuONa (2 g, 26 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (0.4 g, 1.0 mmol) and tris(dibenzylideneacetone)dipalladium(0) (0.18 g, 0.2 mmol) were added to a four-necked reaction flask, 50 mL of toluene was added, and the temperature was heated up to reflux. After the reaction was completed in 2 h, the reaction solution was cooled to room temperature, and the reaction solution was passed through a flash chromatography column with toluene to obtain compound X-3-1-9 (6.2 g, yield 72%) as the final product.

[0429] LC-MS(APCI): 779.58[M+H] +

[0430] 1 H NMR(400 MHz, Methylene Chloride-d2) δ8.55(dd, 1H), 8.31–8.26(m, 1H), 7.98–7.92(m, 1H), 7.83–7.78(m, 1H), 7.75–7.66(m, 3H), 7.57–7.48(m, 2H), 7.36–7.24(m, 3H), 7.20–7.15(m, 2H), 7.11–7.00(m, 8H), 6.96–6.74(m, 12H), 6.59–6.54(m, 2H), 6.49(d, 1H), 6.38(dd, 1H).

[0431] Synthesis Example 14: Synthesis of Compound T14

[0432]

[0433] Under a nitrogen atmosphere, intermediate 1 (5.0 g, 10.1 mmol), intermediate T14-1 (3.0 g, 10.1 mmol), t-BuONa (1.9 g, 20.2 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (0.4 g, 1.0 mmol) and tris(dibenzylideneacetone)dipalladium(0) (0.18 g, 0.2 mmol) were added to a four-necked reaction flask, then 50 mL of toluene was added, and the temperature was heated up to reflux. After the reaction was completed in 2 h, the reaction solution was cooled to room temperature, 100 mL of water was added, and the mixture was extracted with dichloromethane. The organic phase was concentrated and evaporated to dryness, and then purified by refluxing and slurrying with 50 mL of ethyl acetate to obtain compound T14 (4.2 g, yield 55%) as the final product.

[0434] LC-MS(APCI): 758.49[M+H] +

[0435] 1 H NMR (400 MHz, Methylene Chloride - d2) δ 8.52 (dd, 1H), 8.39–8.26 (m, 1H), 8.02–7.92 (m, 1H), 7.86–7.65 (m, 7H), 7.55–7.39 (m, 4H), 7.38–7.16 (m, 7H), 7.08 (ddd, 1H), 7.03–6.95 (m, 3H), 6.92–6.78 (m, 3H), 6.69–6.56 (m, 2H), 6.50 (d, 1H).

[0436] Synthesis Example 15: Synthesis of Compound X - 3 - 1 - 170

[0437]

[0438] Under a nitrogen atmosphere, intermediate T15 - 1 (5.0 g, 15.5 mmol), intermediate 1 (7.6 g, 15.4 mmol), t - BuONa (3 g, 31 mmol), Pd2(dba)3 (0.34 g, 0.4 mmol), and Sphos (0.33 g, 0.8 mmol) were added into a four - necked reaction flask. Then 50 mL of toluene was added, and the temperature was raised to reflux. After the reaction was completed in 2 h, the reaction solution was cooled to room temperature and purified by column chromatography (n - hexane:dichloromethane = 5:1) to obtain compound X - 3 - 1 - 170 (5.0 g, yield 41.7%) as the final product.

[0439] LC - MS (APCI): 779.42 [M + H] + .

[0440] 1 H NMR (400 MHz, Methylene Chloride - d2) δ 8.56 (d, J = 8.3 Hz, 1H), 8.34–8.28 (m, 1H), 7.98–7.92 (m, 1H), 7.86–7.80 (m, 1H), 7.76–7.68 (m, 3H), 7.57 (ddd, J = 8.2, 6.7, 1.3 Hz, 1H), 7.50 (d, J = 8.9 Hz, 1H), 7.42–7.29 (m, 8H), 7.28–7.16 (m, 8H), 7.09–7.00 (m, 5H), 6.96 (t, J = 7.9 Hz, 1H), 6.90–6.76 (m, 3H), 6.53–6.43 (m, 4H).

[0441] Synthesis Example 16: Synthesis of Compound X - 3 - 1 - 17

[0442]

[0443] Under a nitrogen atmosphere, into a 250 ml four-necked flask were successively added intermediate T16-1 (4.5 g, 14.0 mmol), intermediate 1 (8.3 g, 16.8 mmol), potassium carbonate (4.92 g, 28 mmol), tris(dibenzylideneacetone)dipalladium (0.13 g, 0.14 mmol), and 2-dicyclohexylphosphino-2′,6′-dimethoxy-biphenyl (0.23 g, 0.556 mmol). Then 100 ml of toluene was added, and the reaction was carried out at 95 °C for 16 h. The reaction solution was cooled to room temperature, purified by passing through a chromatography column (n-hexane:dichloromethane = 4:1), and slurried to obtain the final product, compound X-3-1-17 (3.85 g, yield 35.2%).

[0444] LC-MS: 779.39 [M+H] + .

[0445] 1 H NMR (400 MHz, Methylene Chloride-d2) δ 8.66 (d, J = 8.3 Hz, 1H), 8.42 (dd, J = 6.1, 3.1 Hz, 1H), 8.07–7.99 (m, 1H), 7.93 (dd, J = 8.2, 1.3 Hz, 1H), 7.86–7.74 (m, 3H), 7.71–7.63 (m, 5H), 7.61–7.54 (m, 3H), 7.47 (t, J = 7.7 Hz, 4H), 7.40–7.30 (m, 4H), 7.22–7.12 (m, 3H), 7.12–6.99 (m, 3H), 6.98–6.84 (m, 4H), 6.73 (dd, J = 7.6, 1.7 Hz, 2H), 6.65–6.51 (m, 3H).

[0446] Synthesis Example 17: Synthesis of Compound X-3-1-35

[0447]

[0448] Under a nitrogen atmosphere, the intermediate T17-1 (4.7 g, 13.54 mmol), intermediate 1 (6.4 g, 12.89 mmol), tris(dibenzylideneacetone)dipalladium(0) (354 mg, 0.386 mmol), 2-(dicyclohexylphosphino)-2',6'-dimethoxybiphenyl (530 mg, 1.20 mmol) and sodium tert-butoxide (2.5 g, 25.78 mmol) were added into a 250 mL four-necked flask. Then 100 mL of toluene was added, and the reaction system was heated to reflux, followed by stirring at a constant temperature for 5 h. After the reaction was completed, the reaction solution was cooled to room temperature. It was extracted and separated with dichloromethane + water, and the organic phases were combined. The mixture was dried by rotary evaporation with silica gel and then purified by passing through a chromatography column (n-hexane:dichloromethane = 5:1) to obtain X-3-1-35 (6.8 g, yield 65.7%) as the final product.

[0449] LC-MS(APCI):803.56[M+H] + .

[0450] 1 1H NMR(400MHz,Methylene Chloride-d2)δ8.74–8.61(m,2H),8.52(d,J=8.3Hz,1H),8.34–8.27(m,1H),7.99–7.93(m,1H),7.86–7.66(m,6H),7.58(dddd,J=16.3,10.5,7.3,1.4Hz,3H),7.52–7.40(m,4H),7.36–7.30(m,1H),7.29–7.19(m,4H),7.10(ddd,J=8.4,7.2,1.4Hz,1H),7.06–7.01(m,3H),6.99–6.93(m,2H),6.91–6.79(m,4H),6.72–6.67(m,2H),6.66–6.60(m,2H),6.52(d,J=8.2Hz,1H).

[0451] Synthesis Example 18: Synthesis of Compound X-3-1-56

[0452]

[0453] Under a nitrogen atmosphere, intermediate 1 (6 g, 12.2 mmol), 4-(4-dibenzofuranyl)-N-phenylaniline (4.0 g, 12.2 mmol), t-BuONa (2.3 g, 24.4 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (0.3 g, 0.7 mmol) and tris(dibenzylideneacetone) dipalladium (0.33 g, 0.37 mmol) were added into a four-necked reaction flask, and then 60 mL of toluene was added. The temperature was raised to reflux. After the reaction was completed in 2 h, the reaction solution was cooled to room temperature, 100 mL of water was added, and the mixture was extracted with dichloromethane. The organic phase was concentrated and dried by rotary evaporation, and then purified by refluxing and slurrying with 60 mL of ethanol to obtain compound X-3-1-56 (7.1 g, yield 74%) as the final product.

[0454] LC-MS (APCI): 793.43 [M+H] +

[0455] 1 1H NMR (400 MHz, CD2Cl2) δ 8.56 (d, 1H), 8.37–8.30 (m, 1H), 8.00–7.92 (m, 2H), 7.84 (dd, 2H), 7.77–7.68 (m, 3H), 7.57–7.49 (m, 3H), 7.48–7.39 (m, 4H), 7.35–7.19 (m, 7H), 7.11–7.01 (m, 2H), 6.98–6.91 (m, 2H), 6.90–6.79 (m, 4H), 6.69–6.60 (m, 4H), 6.51 (d, 1H).

[0456] Synthesis Example 19: Synthesis of Compound X-3-1-30

[0457]

[0458] Under a nitrogen atmosphere, intermediate T19-1 (6.0 g, 12.14 mmol), intermediate 1 (3.6 g, 12.14 mmol), Pd2(dab)3 (334 mg, 0.36 mmol), Sphos (500 mg, 1.21 mmol) and sodium tert-butoxide (2.3 g, 24.29 mmol) were added into a 250 mL four-necked flask, 100 mL of toluene was added, and the temperature was raised to reflux in the reaction system. After the reaction was completed in 5 h, heating was stopped and the reaction solution was cooled to room temperature. The reaction solution was extracted with dichloromethane, dried over anhydrous sodium sulfate and the solvent was removed. Purification was carried out by column chromatography (development solvent volume ratio: n-hexane:dichloromethane = 3:1) to obtain compound X-3-1-30 (5.4 g, yield 59.1%) as a white solid.

[0459] LC-MS(APCI): 753.37 [M+H] +

[0460] 1 H NMR (400 MHz, Methylene Chloride-d2) δ 8.70 (d, J = 8.3 Hz, 1H), 8.49–8.42 (m, 1H), 8.10–8.05 (m, 1H), 7.99–7.92 (m, 4H), 7.91–7.80 (m, 4H), 7.74–7.67 (m, 2H), 7.62 (d, J = 8.9 Hz, 1H), 7.57–7.48 (m, 4H), 7.40–7.32 (m, 3H), 7.31–7.26 (m, 2H), 7.22–7.06 (m, 4H), 7.01–6.90 (m, 4H), 6.82–6.76 (m, 2H), 6.68–6.57 (m, 3H).

[0461] The following application examples further illustrate the application of the arylamine compound described in the present invention in the preparation of organic electroluminescent devices.

[0462] Application Example 1:

[0463] This embodiment provides an organic electroluminescent device, as Figure 1 shown, including a substrate 1, an anode 2, a hole injection layer 3, a first hole transport layer 4, a second hole transport layer 5, a light-emitting layer 6, a hole blocking layer 7, an electron transport layer 8, and a cathode 9 stacked from bottom to top. The hole injection layer 3, the first hole transport layer 4, and the second hole transport layer 5 are hole transport regions, and the hole blocking layer 7 and the electron transport layer 8 are electron transport regions.

[0464] The specific device structure is:

[0465] ITO / HT1-PD3% (10 nm) / HT1 (60 nm) / HT2 (5 nm) / BH-BD3% (20 nm) / HB (5 nm) / ET-LiQ50% (30 nm) / Mg:Ag 1:9 (100 nm)

[0466] Device preparation process:

[0467] The bottom-emitting glass substrate 1 used in this embodiment is purchased from Guangdong Trulyst Optoelectronics Co., Ltd., and ITO is used as the anode 2. First, the bottom-emitting glass substrate is sequentially cleaned with ITO cleaning agent, deionized water, and isopropyl alcohol, and then baked at 180 degrees Celsius for 30 minutes to dry it.

[0468] Then the bottom-emitting glass substrate is placed in the evaporation chamber, and the vacuum degree is about 10 -8In the case of the support, each organic layer was sequentially deposited on the ITO anode by thermal vacuum evaporation at a rate of 0.2 - 2 Å / second. Among them, 3% of PD was doped in HT1 to form a thickness of 10 nm as the hole injection layer 3, HT1 was formed with a thickness of 60 nm as the first hole transport layer 4, HT2 with a thickness of 5 nm was evaporated on HT1 as the second hole transport layer 5, 3% of BD was doped in the anthracene host BH to form a blue light-emitting layer 6 with a thickness of 20 nm, HB was formed with a thickness of 5 nm as the hole blocking layer 7, ET doped with 50% Liq was formed into an electron transport layer 8 with a thickness of 30 nm, and Mg:Ag (1:9) was formed with a thickness of 100 nm as the cathode 9. Finally, the device was transferred back to the glove box and encapsulated with a glass cover and a moisture absorbent to complete the device, denoted as the organic electronic component 1. In the same layer of this device embodiment, different materials were co-evaporated and existed in the layer in a certain volume ratio. For example, 50% of Liq was in the volume ratio of 50% ET and 50% Liq. The compound of the present invention was used after sublimation purification, HPLC: 99.9%.

[0469] The specific structure of the compound involved is as follows. The synthesis of HT2 can refer to the synthesis methods of Intermediate 2 and Synthesis Example 1. Only the initial raw material 2,3-benzocarbazole needs to be replaced with carbazole in the steps of Intermediate 2, LC-MS (APCI): 744.59 (M + H + )

[0470]

[0471] Examples and Comparative Examples

[0472] The compound X-2-1-56 prepared in Synthesis Example 1 of the present invention was used to replace HT2 to prepare the second hole transport layer, and the organic electronic component 2 was fabricated in the same method.

[0473] The compound X-2-5-56 prepared in Synthesis Example 2 of the present invention was used to replace HT2 to prepare the second hole transport layer, and the organic electronic component 3 was fabricated in the same method.

[0474] The compound X-3-1-28 prepared in Synthesis Example 3 of the present invention was used to replace HT2 to prepare the second hole transport layer, and the organic electronic component 4 was fabricated in the same method.

[0475] The compound X-3-1-277 prepared in Synthesis Example 4 of the present invention was used to replace HT2 to prepare the second hole transport layer, and the organic electronic component 5 was fabricated in the same method.

[0476] The compound X-3-2-26 prepared in Synthesis Example 5 of the present invention was used to replace HT2 to prepare the second hole transport layer, and the organic electronic component 6 was fabricated in the same method.

[0477] Use the compound X-3-1-88 prepared in Synthesis Example 6 of the present invention to replace HT2 to prepare the second hole transport layer, and fabricate the organic electronic device 7 in the same manner.

[0478] Use the compound X-3-1-283 prepared in Synthesis Example 7 of the present invention to replace HT2 to prepare the second hole transport layer, and fabricate the organic electronic device 8 in the same manner.

[0479] Use the compound X-3-1-11 prepared in Synthesis Example 8 of the present invention to replace HT2 to prepare the second hole transport layer, and fabricate the organic electronic device 9 in the same manner.

[0480] Use the compound X-3-1-59 prepared in Synthesis Example 9 of the present invention to replace HT2 to prepare the second hole transport layer, and fabricate the organic electronic device 10 in the same manner.

[0481] Use the compound X-2-5-28 prepared in Synthesis Example 10 of the present invention to replace HT2 to prepare the second hole transport layer, and fabricate the organic electronic device 11 in the same manner.

[0482] Use the compound X-3-1-78 prepared in Synthesis Example 11 of the present invention to replace HT2 to prepare the second hole transport layer, and fabricate the organic electronic device 12 in the same manner.

[0483] Use the compound X-3-1-10 prepared in Synthesis Example 12 of the present invention to replace HT2 to prepare the second hole transport layer, and fabricate the organic electronic device 13 in the same manner.

[0484] Use the compound X-3-1-9 prepared in Synthesis Example 13 of the present invention to replace HT2 to prepare the second hole transport layer, and fabricate the organic electronic device 14 in the same manner.

[0485] Use the compound T14 (partially deuterated X-3-1-28) prepared in Synthesis Example 14 of the present invention to replace HT2 to prepare the second hole transport layer, and fabricate the organic electronic device 15 in the same manner.

[0486] Use the compound X-3-1-170 prepared in Synthesis Example 15 of the present invention to replace HT2 to prepare the second hole transport layer, and fabricate the organic electronic device 16 in the same manner.

[0487] Use the compound X-3-1-17 prepared in Synthesis Example 16 of the present invention to replace HT2 to prepare the second hole transport layer, and fabricate the organic electronic device 17 in the same manner.

[0488] Use the compound X-3-1-35 prepared in Synthesis Example 17 of the present invention to replace HT2 to prepare the second hole transport layer, and fabricate the organic electronic device 18 in the same manner.

[0489] The compound X-3-1-56 prepared in Synthesis Example 18 of the present invention was used to replace HT2 to prepare the second hole transport layer, and the organic electronic device 19 was fabricated in the same manner.

[0490] The compound X-3-1-30 prepared in Synthesis Example 19 of the present invention was used to replace HT2 to prepare the second hole transport layer, and the organic electronic device 20 was fabricated in the same manner.

[0491] Evaluation of organic electroluminescent device

[0492] IVL test instrument: F STAR Optical Measurement Systems, model: FS-2000GA4; ambient atmosphere, room temperature.

[0493] The current efficiency was tested at a current density of 15 mA / cm 2 .

[0494] The driving voltage was tested at a current density of 15 mA / cm 2 .

[0495] Driving voltage, V Current efficiency, cd / A Organic electronic component 1 3.76 5.7 Organic electronic component 2 3.66 5.8 Organic electronic component 3 3.64 5.9 Organic electronic component 4 3.72 5.9 Organic electronic component 5 3.70 5.9 Organic electronic component 6 3.69 6.0 Organic electronic component 7 3.67 5.8 Organic electronic component 8 3.70 5.9 Organic electronic component 9 3.72 6.1 Organic electronic component 10 3.69 5.8 Organic electronic component 11 3.65 6.2 Organic electronic component 12 3.67 6.2 Organic electronic component 13 3.71 5.9 Organic electronic component 14 3.72 5.8 Organic electronic component 15 3.70 5.9 Organic electronic component 16 3.69 5.9 Organic electronic component 17 3.67 6.1 Organic electronic component 18 3.65 6.3 Organic electronic component 19 3.74 5.9 Organic electronic component 20 3.67 6.1

[0496] For the organic electroluminescent device 2-20 prepared from the compound of the present application and the organic electronic device 1, the compounds with a benzocarbazole structure and a phenylene-dibenzofuran structure have strong hole transport ability, can quickly transfer holes to the light-emitting layer, and at the same time have appropriate energy levels, can confine carriers in the light-emitting layer, and reduce the efficiency decline caused by carrier spillage. The organic electroluminescent device prepared from the compound of the present application has a lower driving voltage and a higher current efficiency. Therefore, the compounds of the present invention are suitable for preparing high-performance organic electroluminescent devices.

[0497] It is easy for those skilled in the art to understand that the above are only preferred embodiments of the present invention and are not used to limit the present invention. Any modifications, equivalent replacements, and improvements made within the spirit and principle of the present invention shall be included in the protection scope of the present invention.

Claims

1. An aromatic amine compound, characterized in that, The compound has the structure shown in formula (1), wherein, Ar3 has the following structure: "----" represents the connection position; A1 is selected from a substituted or unsubstituted C6-C14 aromatic ring, A2 is selected from a substituted or unsubstituted C10-C14 aromatic ring, L5 is selected from a substituted or unsubstituted C6-C60 arylene group, L4 is selected from a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, L1-L3 are each independently selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C3-C60 heteroarylene group, Ar1 and Ar2 are each independently selected from hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C2-C10 alkenyl group, a substituted or unsubstituted C2-C10 alkynyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C3-C60 heteroaryl group; In the "substituted or unsubstituted", the substituents in the case of substitution are independently selected from deuterium, halogen, cyano, a C1-C10 alkyl group, a C3-C10 cycloalkyl group, a C1-C10 alkoxy group, a C2-C10 alkenyl group, a C2-C10 alkynyl group, a C6-C60 aryl group, a C3-C60 heteroaryl group, a C6-C60 carbocyclic group, a C3-C60 heterocyclic group, The heteroatoms in the heterocyclic group and heteroaryl group are selected from at least one of N, O, S, Si, P.

2. The aromatic amine compound according to claim 1, wherein The compound has the structure shown in formula (2), R2 is selected from hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C2-C10 alkenyl group, a substituted or unsubstituted C2-C10 alkynyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C3-C60 heteroaryl group; b is an integer between 0 and 10; when b is 2 or greater, multiple R2s are the same or different from each other; The definitions of L1-L5, Ar1, and Ar2 are the same as those defined in claim 1; The definition of the substituents in the "substituted or unsubstituted" is the same as that defined in claim 1.

3. The aromatic amine compound according to claim 1, wherein L5 is selected from a phenylene group, a naphthylene group, a biphenylene group.

4. The aromatic amine compound according to claim 1, wherein The aromatic amine compound has the structures shown in formula (3)-(8), wherein, R1-R3 are each independently selected from hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C2-C10 alkenyl group, a substituted or unsubstituted C2-C10 alkynyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C3-C60 heteroaryl group; a is an integer between 0 and 4; when a is 2 or greater, multiple R1s are the same or different from each other; b is an integer between 0 and 10; when b is 2 or greater, multiple R2s are the same or different from each other; c is selected from integers between 0 and 6; when c is 2 or greater, the multiple R3s are the same as or different from each other; X is selected from O or S; The definitions of L1, L2, Ar1, and Ar2 are the same as those defined in claim 1; The definition of the substituent when "substituted or unsubstituted" is substituted is the same as that defined in claim 1.

5. The aromatic amine compound according to claim 1, wherein The arylamine compound has the structure shown in formula (9)-(26), wherein, R1-R3 are each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C2-C10 alkynyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; a is selected from integers between 0 and 4; when a is 2 or greater, the multiple R1s are the same as or different from each other; b is selected from integers between 0 and 10; when b is 2 or greater, the multiple R2s are the same as or different from each other; c is selected from integers between 0 and 6; when c is 2 or greater, the multiple R3s are the same as or different from each other; X is selected from O or S; The definitions of L1, L2, Ar1, and Ar2 are the same as those defined in claim 1; The definition of the substituent when "substituted or unsubstituted" is substituted is the same as that defined in claim 1.

6. The arylamine compound according to any one of claims 1-5, characterized in that, L1 and L2 are each independently selected from a single bond, substituted or unsubstituted groups as follows: The definition of the substituent when "substituted or unsubstituted" is substituted is the same as that defined in claim 1.

7. The aromatic amine compound according to any one of claims 1-5, characterized in that, Ar1 and Ar2 are each independently selected from hydrogen, substituted or unsubstituted groups as follows: The definition of the substituent when "substituted or unsubstituted" is substituted is the same as that defined in claim 1.

8. The aromatic amine compound according to claim 1, wherein Ar3-L5-L4-L3- is selected from the following structures: X-m-n is the substituent number represented by Ar3-L5-L4-L3-, and X-m-n represents all substituents represented by X-1-1 to X-1-24, X-2-1 to X-2-24, X-3-1 to X-3-24; 9. The aromatic amine compound according to claim 8, wherein -L1-Ar1 and -L2-Ar2 are each independently selected from the following structures: wherein, the structure is unsubstituted or substituted with one or more deuteriums, and preferably the structure is unsubstituted.

10. The aromatic amine compound according to claim 9, characterized in that, The arylamine compound is selected from the following structures: wherein, Ar3-L5-L4-L3-, -L1-Ar1, and -L2-Ar2 are respectively connected to N; When Ar3-L5-L4-L3- is selected from X-3-1, the compound numbers are X-3-1-1 to X-3-1-3655, When Ar3-L5-L4-L3- is replaced with X-1-1 for X-3-1, the compound numbers are X-1-1-1 to X-1-1-3655, When Ar3-L5-L4-L3- is replaced with X-1-2 for X-3-1, the compound numbers are X-1-2-1 to X-1-2-3655, When Ar3-L5-L4-L3- is replaced with X-1-3 for X-3-1, the compound numbers are X-1-3-1 to X-1-3-3655, When X-3-1 is replaced with X-1-4 in Ar3-L5-L4-L3, the compound numbers are X-1-4-1 to X-1-4-3655, When X-3-1 is replaced with X-1-5 in Ar3-L5-L4-L3, the compound numbers are X-1-5-1 to X-1-5-3655, When X-3-1 is replaced with X-1-6 in Ar3-L5-L4-L3, the compound numbers are X-1-6-1 to X-1-6-3655, When X-3-1 is replaced with X-1-7 in Ar3-L5-L4-L3, the compound numbers are X-1-7-1 to X-1-7-3655, When X-3-1 is replaced with X-1-8 in Ar3-L5-L4-L3, the compound numbers are X-1-8-1 to X-1-8-3655, When X-3-1 is replaced with X-1-9 in Ar3-L5-L4-L3, the compound numbers are X-1-9-1 to X-1-9-3655, When X-3-1 is replaced with X-1-10 in Ar3-L5-L4-L3, the compound numbers are X-1-10-1 to X-1-10-3655, When X-3-1 is replaced with X-1-11 in Ar3-L5-L4-L3, the compound numbers are X-1-11-1 to X-1-11-3655, When X-3-1 is replaced with X-1-12 in Ar3-L5-L4-L3, the compound numbers are X-1-12-1 to X-1-12-3655, When X-3-1 is replaced with X-1-13 in Ar3-L5-L4-L3, the compound numbers are X-1-13-1 to X-1-13-3655, When X-3-1 is replaced with X-1-14 in Ar3-L5-L4-L3, the compound numbers are X-1-14-1 to X-1-14-3655, When X-3-1 is replaced with X-1-15 in Ar3-L5-L4-L3, the compound numbers are X-1-15-1 to X-1-15-3655, When X-3-1 is replaced with X-1-16 in Ar3-L5-L4-L3, the compound numbers are X-1-16-1 to X-1-16-3655, When X-3-1 is replaced with X-1-17 in Ar3-L5-L4-L3, the compound numbers are X-1-17-1 to X-1-17-3655, When X-3-1 is replaced with X-1-18 in Ar3-L5-L4-L3, the compound numbers are X-1-18-1 to X-1-18-3655, When X-3-1 is replaced with X-1-19 in Ar3-L5-L4-L3, the compound numbers are X-1-19-1 to X-1-19-3655, When X-3-1 is replaced with X-1-20 in Ar3-L5-L4-L3, the compound numbers are X-1-20-1 to X-1-20-3655, When X-3-1 is replaced with X-1-21 in Ar3-L5-L4-L3, the compound numbers are X-1-21-1 to X-1-21-3655, When X-3-1 is replaced by X-1-22 in Ar3-L5-L4-L3, the compound numbers are X-1-22-1 to X-1-22-3655, When X-3-1 is replaced by X-1-23 in Ar3-L5-L4-L3, the compound numbers are X-1-23-1 to X-1-23-3655, When X-3-1 is replaced by X-1-24 in Ar3-L5-L4-L3, the compound numbers are X-1-24-1 to X-1-24-3655, When X-3-1 is replaced by X-2-1 in Ar3-L5-L4-L3, the compound numbers are X-2-1-1 to X-2-1-3655, When X-3-1 is replaced by X-2-2 in Ar3-L5-L4-L3, the compound numbers are X-2-2-1 to X-2-2-3655, When X-3-1 is replaced by X-2-3 in Ar3-L5-L4-L3, the compound numbers are X-2-3-1 to X-2-3-3655, When X-3-1 is replaced by X-2-4 in Ar3-L5-L4-L3, the compound numbers are X-2-4-1 to X-2-4-3655, When X-3-1 is replaced by X-2-5 in Ar3-L5-L4-L3, the compound numbers are X-2-5-1 to X-2-5-3655, When X-3-1 is replaced by X-2-6 in Ar3-L5-L4-L3, the compound numbers are X-2-6-1 to X-2-6-3655, When X-3-1 is replaced by X-2-7 in Ar3-L5-L4-L3, the compound numbers are X-2-7-1 to X-2-7-3655, When X-3-1 is replaced by X-2-8 in Ar3-L5-L4-L3, the compound numbers are X-2-8-1 to X-2-8-3655, When X-3-1 is replaced by X-2-9 in Ar3-L5-L4-L3, the compound numbers are X-2-9-1 to X-2-9-3655, When X-3-1 is replaced by X-2-10 in Ar3-L5-L4-L3, the compound numbers are X-2-10-1 to X-2-10-3655, When X-3-1 is replaced by X-2-11 in Ar3-L5-L4-L3, the compound numbers are X-2-11-1 to X-2-11-3655, When X-3-1 is replaced by X-2-12 in Ar3-L5-L4-L3, the compound numbers are X-2-12-1 to X-2-12-3655, When X-3-1 is replaced by X-2-13 in Ar3-L5-L4-L3, the compound numbers are X-2-13-1 to X-2-13-3655, When X-3-1 is replaced by X-2-14 in Ar3-L5-L4-L3, the compound numbers are X-2-14-1 to X-2-14-3655, When X-3-1 is replaced by X-2-15 in Ar3-L5-L4-L3, the compound numbers are X-2-15-1 to X-2-15-3655, When X-3-1 is replaced with X-2-16 in Ar3-L5-L4-L3, the compound numbers are X-2-16-1 to X-2-16-3655, When X-3-1 is replaced with X-2-17 in Ar3-L5-L4-L3, the compound numbers are X-2-17-1 to X-2-17-3655, When X-3-1 is replaced with X-2-18 in Ar3-L5-L4-L3, the compound numbers are X-2-18-1 to X-2-18-3655, When X-3-1 is replaced with X-2-19 in Ar3-L5-L4-L3, the compound numbers are X-2-19-1 to X-2-19-3655, When X-3-1 is replaced with X-2-20 in Ar3-L5-L4-L3, the compound numbers are X-2-20-1 to X-2-20-3655, When X-3-1 is replaced with X-2-21 in Ar3-L5-L4-L3, the compound numbers are X-2-21-1 to X-2-21-3655, When X-3-1 is replaced with X-2-22 in Ar3-L5-L4-L3, the compound numbers are X-2-22-1 to X-2-22-3655, When X-3-1 is replaced with X-2-23 in Ar3-L5-L4-L3, the compound numbers are X-2-23-1 to X-2-23-3655, When X-3-1 is replaced with X-2-24 in Ar3-L5-L4-L3, the compound numbers are X-2-24-1 to X-2-24-3655, When X-3-1 is replaced with X-3-2 in Ar3-L5-L4-L3, the compound numbers are X-3-2-1 to X-3-2-3655, When X-3-1 is replaced with X-3-3 in Ar3-L5-L4-L3, the compound numbers are X-3-3-1 to X-3-3-3655, When X-3-1 is replaced with X-3-4 in Ar3-L5-L4-L3, the compound numbers are X-3-4-1 to X-3-4-3655, When X-3-1 is replaced with X-3-5 in Ar3-L5-L4-L3, the compound numbers are X-3-5-1 to X-3-5-3655, When X-3-1 is replaced with X-3-6 in Ar3-L5-L4-L3, the compound numbers are X-3-6-1 to X-3-6-3655, When X-3-1 is replaced with X-3-7 in Ar3-L5-L4-L3, the compound numbers are X-3-7-1 to X-3-7-3655, When X-3-1 is replaced with X-3-8 in Ar3-L5-L4-L3, the compound numbers are X-3-8-1 to X-3-8-3655, When X-3-1 is replaced with X-3-9 in Ar3-L5-L4-L3, the compound numbers are X-3-9-1 to X-3-9-3655, When X-3-1 is replaced with X-3-10 in Ar3-L5-L4-L3, the compound numbers are X-3-10-1 to X-3-10-3655, When X-3-1 is replaced by X-3-11 in Ar3-L5-L4-L3, the compound numbers are X-3-11-1 to X-3-11-3655, When X-3-1 is replaced by X-3-12 in Ar3-L5-L4-L3, the compound numbers are X-3-12-1 to X-3-12-3655, When X-3-1 is replaced by X-3-13 in Ar3-L5-L4-L3, the compound numbers are X-3-13-1 to X-3-13-3655, When X-3-1 is replaced by X-3-14 in Ar3-L5-L4-L3, the compound numbers are X-3-14-1 to X-3-14-3655, When X-3-1 is replaced by X-3-15 in Ar3-L5-L4-L3, the compound numbers are X-3-15-1 to X-3-15-3655, When X-3-1 is replaced by X-3-16 in Ar3-L5-L4-L3, the compound numbers are X-3-16-1 to X-3-16-3655, When X-3-1 is replaced by X-3-17 in Ar3-L5-L4-L3, the compound numbers are X-3-17-1 to X-3-17-3655, When X-3-1 is replaced by X-3-18 in Ar3-L5-L4-L3, the compound numbers are X-3-18-1 to X-3-18-3655, When X-3-1 is replaced by X-3-19 in Ar3-L5-L4-L3, the compound numbers are X-3-19-1 to X-3-19-3655, When X-3-1 is replaced by X-3-20 in Ar3-L5-L4-L3, the compound numbers are X-3-20-1 to X-3-20-3655, When X-3-1 is replaced by X-3-21 in Ar3-L5-L4-L3, the compound numbers are X-3-21-1 to X-3-21-3655, When X-3-1 is replaced by X-3-22 in Ar3-L5-L4-L3, the compound numbers are X-3-22-1 to X-3-22-3655, When X-3-1 is replaced by X-3-23 in Ar3-L5-L4-L3, the compound numbers are X-3-23-1 to X-3-23-3655, When X-3-1 is replaced by X-3-24 in Ar3-L5-L4-L3, the compound numbers are X-3-24-1 to X-3-24-3655.

11. The aromatic amine compound according to claim 9, characterized in that, The aromatic amine compound is selected from the following structures:

12. An organic electroluminescent element, comprising a substrate, an anode, a hole transport region, a light-emitting layer, an electron transport region, and a cathode, wherein the light-emitting layer is located between the anode and the cathode, the hole transport region is located between the anode and the light-emitting layer, the electron transport region is located between the light-emitting layer and the cathode, and the hole transport region contains the compound according to any one of claims 1-11; Preferably, the hole transport region includes a first hole transport layer and a second hole transport layer. The second hole transport layer is located between the first hole transport layer and the light-emitting layer, and the second hole transport layer contains the compound according to any one of claims 1-11.

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