Aromatic amine compound, organic light emitting diode, and electronic device

Abstract

Provided are an organic compound, an organic light emitting diode, and an electronic device. A compound having a benzocarbazole structure and a phenylene-dibenzofuran structure has strong hole transport capability, and can quickly transfer holes to a light-emitting layer. In addition, it has a suitable energy level, and can confine carriers within the light-emitting layer and reduce a decrease in efficiency caused by carrier overflow. An organic light emitting element prepared from this compound has a lower driving voltage and higher current efficiency, and is suitable for preparing high-performance organic light emitting elements. The compound has the structure shown in formula (1), Ar3 having a structure as shown, A1 being selected from an aromatic ring, A2 being selected from an aromatic ring, L5 being selected from an arylene group, L4 being selected from a dibenzofuranylene group or a dibenzothiophenylene group, L1-L3 each being independently selected from a single bond, an arylene group and a heteroarylene group, and Ar1 and Ar2 each being independently selected from hydrogen, deuterium, a halogen, a cyano group, an alkyl group, a cycloalkyl group, an alkoxy group, an alkenyl group, an alkynyl group, an aryl group and a heteroaryl group.

Description

Aromatic amine compound, organic electroluminescent device and electronic device

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims priority to and the benefit of the following Chinese patent applications filed with the State Intellectual Property Office of China, the entire contents of which are incorporated herein by reference:

[0003] A Chinese patent application with application number CN202410047784.7 and application name “A kind of aromatic amine compound, organic electroluminescent device and electronic device” submitted on January 12, 2024.

[0004] The Chinese patent application with application number CN202410266679.2 and application name “A kind of aromatic amine compound, organic electroluminescent device and electronic device” was submitted on March 8, 2024.

[0005] A Chinese patent application with application number CN202410736219.1 and application name “A kind of aromatic amine compound, organic electroluminescent device and electronic device” was submitted on June 7, 2024.

[0006] A Chinese patent application with application number CN202510029022.9 and application name “A kind of aromatic amine compound, organic electroluminescent device and electronic device” submitted on January 8, 2025. Technical Field

[0007] The present invention relates to the technical field of organic electroluminescence, and more specifically, to an aromatic amine compound, an organic electroluminescent device and an electronic device. Background Art

[0008] An organic light emitting diode (OLED) is a self-luminous display device based on organic electroluminescent materials. It has the characteristics of not requiring a backlight source and being thin. It is a technology suitable for flexible light-emitting display devices.

[0009] Organic electroluminescent materials are polymers or small molecules that emit light under the influence of an electric field. To improve the stability and efficiency of organic electroluminescent materials in organic electroluminescent devices, a multilayer organic thin film is prepared between the anode and cathode. These organic thin film layers can be divided into a hole injection layer, a hole transport layer, a main luminescent layer, a luminescent layer dopant, an electron transport layer, and an electron injection layer.

[0010] When an electric field is applied between the anode and cathode of an organic electroluminescent device, holes are injected from the anode and move through the hole transport layer to the light-emitting layer. Simultaneously, electrons are injected from the cathode and move through the electron transport layer to the light-emitting layer. The holes and electrons that move to the light-emitting layer combine to form excitons. When the excitons transition from an excited state to a ground state, energy is released as light, causing the device to emit light.

[0011] To ensure the high performance of organic electroluminescent devices (longer life, higher current efficiency, lower driving voltage, higher color saturation, etc.), it is particularly important to improve the exciton generation efficiency of the light-emitting layer. To prevent the diffusion of excitons, hole transport materials need to have high triplet energy.

[0012] Although there are reports of high-performance organic electroluminescent devices, the performance of the hole transport region has not been fully developed, and existing hole transport region materials still cannot meet people's demand for high-performance organic electroluminescent devices. Summary of the Invention

[0013] In response to the above defects or improvement needs of the prior art, the present invention provides an aromatic amine derivative with a specific parent core, which exhibits excellent performance when used as an organic electroluminescent material, especially as a hole transport region material.

[0014] To achieve the above object, the present invention provides an aromatic amine compound having a structure shown in formula (1):

[0015] Wherein, Ar3 is the following structure:

[0016] Indicates the connection location;

[0017] A1 is selected from substituted or unsubstituted C6-C14 aromatic rings,

[0018] A2 is selected from substituted or unsubstituted C10-C14 aromatic rings,

[0019] L5 is selected from substituted or unsubstituted C6-C60 arylene groups,

[0020] L4 is selected from substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl,

[0021] L1-L3 are each independently selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, or a substituted or unsubstituted C3-C60 heteroarylene group.

[0022] Ar1 and Ar2 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;

[0023] The substituent in the "substituted or unsubstituted" is 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 carbocyclyl, C3-C60 heterocyclyl,

[0024] The heteroatom in the heterocyclic group and the heteroaryl group is selected from at least one of N, O, S, Si and P.

[0025] Furthermore, in an optional embodiment of the present invention, the compound has a structure shown in formula (2),

[0026] 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;

[0027] b is selected from an integer between 0 and 10, preferably an integer between 0 and 9, more preferably an integer between 0 and 8, more preferably an integer between 0 and 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, more preferably 0, 1, 2, 3, particularly preferably 0, 1, 2, particularly preferably 0, 1, and most preferably 0; when b is 2 or greater, multiple R2 are the same or different from each other;

[0028] The definitions of L1-L5, Ar1, and Ar2 are the same as those in the compound of formula (1);

[0029] The definition of the substituent in the "substituted or unsubstituted" is preferably the same as above;

[0030] Preferably, L3 is a single bond;

[0031] Preferably, L5 is selected from phenylene, naphthylene, biphenylene;

[0032] Preferably, L4 is selected from dibenzofuranyl and dibenzothiophenyl; more preferably, L4 is selected from dibenzofuranyl.

[0033] In an optional embodiment of the present invention, the aromatic amine compound is a structure represented by formula (2), wherein 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;

[0034] In the "substituted or unsubstituted" mentioned above, the definition of the substituent when substituted is preferably the same as above.

[0035] Furthermore, in an optional embodiment of the present invention, the aromatic amine compound has a structure represented by formula (2-1),

[0036] 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;

[0037] a is selected from an integer between 0 and 4, preferably 0, 1, 2, 3, more preferably 0, 1, 2, more preferably 0, 1, and most preferably 0; when a is 2 or greater, multiple R1s are the same or different from each other;

[0038] b is selected from an integer between 0 and 10, preferably an integer between 0 and 9, more preferably an integer between 0 and 8, more preferably an integer between 0 and 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, more preferably 0, 1, 2, 3, particularly preferably 0, 1, 2, particularly preferably 0, 1, and most preferably 0; when b is 2 or greater, multiple R2 are the same or different from each other;

[0039] c is selected from an integer between 0 and 6; preferably an integer between 0 and 5, more preferably an integer between 0 and 4, more preferably 0, 1, 2, 3, particularly preferably 0, 1, 2, particularly preferably 0, 1, and most preferably 0; when c is 2 or greater, multiple R3 are the same or different from each other;

[0040] X is selected from O or S;

[0041] L1, L2, Ar1, Ar2 are defined as the same as in the compound of formula (1);

[0042] In the "substituted or unsubstituted" mentioned above, the definition of the substituent when substituted is preferably the same as above.

[0043] Furthermore, in an optional embodiment of the present invention, the aromatic amine compound has a structure as shown in formula (3)-(8),

[0044] 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;

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

[0046] b is selected from an integer between 0 and 10, preferably an integer between 0 and 9, more preferably an integer between 0 and 8, more preferably an integer between 0 and 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, more preferably 0, 1, 2, 3, particularly preferably 0, 1, 2, particularly preferably 0, 1, and most preferably 0; when b is 2 or greater, multiple R2 are the same or different from each other;

[0047] c is selected from an integer between 0 and 6; preferably an integer between 0 and 5, more preferably an integer between 0 and 4, more preferably 0, 1, 2, 3, particularly preferably 0, 1, 2, particularly preferably 0, 1, and most preferably 0; when c is 2 or greater, multiple R3 are the same or different from each other;

[0048] X is selected from O or S;

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

[0050] In the "substituted or unsubstituted" mentioned above, the definition of the substituent when substituted is preferably the same as above.

[0051] In an optional embodiment of the present invention, the aromatic amine compound is a structure represented by formula (3)-(8), wherein 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] In the "substituted or unsubstituted" mentioned above, the definition of the substituent when substituted is preferably the same as above.

[0053] Furthermore, in an optional embodiment of the present invention, the aromatic amine compound has the following structure:

[0054] The definitions of R1-R3, X, a, b, c, L1, L2, Ar1, and Ar2 are the same as those in the compounds of formulas (3)-(8) above.

[0055] Furthermore, in an optional embodiment of the present invention, the aromatic amine compound has the following structure:

[0056] The definitions of R1-R3, X, a, b, c, L1, L2, Ar1, and Ar2 are the same as those in the compounds of formulas (3)-(8) above.

[0057] Furthermore, in an optional embodiment of the present invention, the aromatic amine compound is a structure shown in formula (9)-(26),

[0058] 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;

[0059] a is selected from an integer between 0 and 4, preferably 0, 1, 2, 3, more preferably 0, 1, 2, more preferably 0, 1, and most preferably 0; when a is 2 or greater, multiple R1s are the same or different from each other;

[0060] b is selected from an integer between 0 and 10, preferably an integer between 0 and 9, more preferably an integer between 0 and 8, more preferably an integer between 0 and 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, more preferably 0, 1, 2, 3, particularly preferably 0, 1, 2, particularly preferably 0, 1, and most preferably 0; when b is 2 or greater, multiple R2 are the same or different from each other;

[0061] c is selected from an integer between 0 and 6; preferably an integer between 0 and 5, more preferably an integer between 0 and 4, more preferably 0, 1, 2, 3, particularly preferably 0, 1, 2, particularly preferably 0, 1, and most preferably 0; when c is 2 or greater, multiple R3 are the same or different from each other;

[0062] X is selected from O or S;

[0063] L1, L2, Ar1, Ar2 are defined as the same as in the compound of formula (1);

[0064] In the "substituted or unsubstituted" mentioned above, the definition of the substituent when substituted is preferably the same as above.

[0065] In an optional embodiment of the present invention, the aromatic amine compound is a structure represented by formula (9)-(26), wherein 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;

[0066] In the "substituted or unsubstituted" mentioned above, the definition of the substituent when substituted is preferably the same as above.

[0067] Preferably, R1-R3 are each independently selected from deuterium, halogen, phenyl, biphenyl, naphthyl, anthracenyl, phenanthrenyl, fluoranthenyl, pyrenyl, peryl, triphenylene, pyrrolyl, furanyl, thienyl, indenyl, indolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, carbazolyl, carbolinyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirobifluorenyl;

[0068] a is selected from an integer between 0 and 4; b is selected from an integer between 0 and 10; c is selected from an integer between 0 and 6;

[0069] Preferably, X is selected from O or S; more preferably, X is selected from O;

[0070] Preferably, L1 and L2 are each independently selected from a single bond, a phenylene group, a biphenylene group, a naphthylene group, an anthrylene group, a phenanthrylene group, a fluoranthenylene group, a pyrenylene group, a perylene group, a triphenylene group, a pyrrolylene group, a furylene group, a thienylene group, an indenylene group, an indolylene group, a benzofuranylene group, a benzothienylene group, a dibenzofuranylene group, a dibenzothienylene group, a carbazolyl group, a carbolylene group, a 9,9-dimethylfluorenyl group, a 9,9-diphenylfluorenyl group, and a spirobifluorenyl group;

[0071] Preferably, Ar1 and Ar2 are each independently selected from hydrogen, deuterium, halogen, phenyl, biphenyl, naphthyl, anthracenyl, phenanthrenyl, fluoranthenyl, pyrenyl, peryl, triphenylene, pyrrolyl, furyl, thienyl, indenyl, indolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, carbazolyl, carbolyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirobifluorenyl, benzonaphthofuranyl, benzonaphthothienyl, phenyl-substituted carbazole, naphthyl-substituted carbazolyl, and biphenyl-substituted carbazolyl;

[0072] Preferably, the structure is unsubstituted or substituted with one or more deuteriums, most preferably the structure is unsubstituted.

[0073] Furthermore, in an optional embodiment of the present invention, L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted group as follows:

[0074] In the "substituted or unsubstituted" mentioned above, the definition of the substituent when substituted is preferably the same as above.

[0075] Furthermore, in an optional embodiment of the present invention, Ar1 and Ar2 are each independently selected from hydrogen, and substituted or unsubstituted groups as follows:

[0076] In the "substituted or unsubstituted" mentioned above, the definition of the substituent when substituted is preferably the same as above.

[0077] Further, in an optional embodiment of the present invention, the definition of the substituent in the above-mentioned "substituted or unsubstituted" is preferably independently selected from deuterium, fluoro, cyano, methyl, ethyl, tert-butyl, cyclohexyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, fluoranthenyl, triphenylene, A combination of one or more of 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32,

[0078] Further, in an optional embodiment of the present invention, the Ar3-L5-L4-L3- is selected from the following structures: Xmn is the substituent number represented by Ar3-L5-L4-L3-, Xmn represents all substituents represented by X-1-1 to X-1-24, X-2-1 to X-2-24, and X-3-1 to X-3-24,

[0079] Further, in an optional embodiment of the present invention, the -L1-Ar1 and -L2-Ar2 are each independently selected from the following structures:

[0080] Wherein, the structure is unsubstituted or substituted with one or more deuteriums, and most preferably the structure is unsubstituted.

[0081] Preferably, the -L1-Ar1 and -L2-Ar2 are each independently selected from the structures of Formula Y1 to Formula Y85, wherein the structures are unsubstituted or substituted with one or more deuteriums, and most preferably the structures are unsubstituted.

[0082] Furthermore, in an optional embodiment of the present invention, the aromatic amine compound is selected from the following structures:

[0083] Among them, Ar3-L5-L4-L3-, -L1-Ar1, and -L2-Ar2 are connected to N respectively;

[0084] When Ar3-L5-L4-L3- is selected from X-3-1, the compound numbers are X-3-1-1 to X-3-1-3655,

[0085] When Ar3-L5-L4-L3- is replaced by X-1-1 in place of X-3-1, the compound numbers are X-1-1-1 to X-1-1-3655.

[0086] When Ar3-L5-L4-L3- is replaced by X-1-2 in place of X-3-1, the compound numbers are X-1-2-1 to X-1-2-3655.

[0087] When Ar3-L5-L4-L3- is replaced by X-1-3 in place of X-3-1, the compound numbers are X-1-3-1 to X-1-3-3655.

[0088] When Ar3-L5-L4-L3- is replaced by X-1-4 in place of X-3-1, the compound numbers are X-1-4-1 to X-1-4-3655.

[0089] When Ar3-L5-L4-L3- is replaced by X-1-5 in place of X-3-1, the compound numbers are X-1-5-1 to X-1-5-3655.

[0090] When Ar3-L5-L4-L3- is replaced by X-1-6 in place of X-3-1, the compound numbers are X-1-6-1 to X-1-6-3655.

[0091] When Ar3-L5-L4-L3- is replaced by X-1-7 in place of X-3-1, the compound numbers are X-1-7-1 to X-1-7-3655.

[0092] When Ar3-L5-L4-L3- is replaced by X-1-8 in place of X-3-1, the compound numbers are X-1-8-1 to X-1-8-3655.

[0093] When Ar3-L5-L4-L3- is replaced by X-1-9 in place of X-3-1, the compound numbers are X-1-9-1 to X-1-9-3655.

[0094] When Ar3-L5-L4-L3- is replaced by X-1-10 in place of X-3-1, the compound numbers are X-1-10-1 to X-1-10-3655.

[0095] When Ar3-L5-L4-L3- is replaced by X-1-11 in place of X-3-1, the compound numbers are X-1-11-1 to X-1-11-3655.

[0096] When Ar3-L5-L4-L3- is replaced by X-1-12 in place of X-3-1, the compound numbers are X-1-12-1 to X-1-12-3655.

[0097] When Ar3-L5-L4-L3- is replaced by X-1-13 in place of X-3-1, the compound numbers are X-1-13-1 to X-1-13-3655.

[0098] When Ar3-L5-L4-L3- is replaced by X-1-14 in place of X-3-1, the compound numbers are X-1-14-1 to X-1-14-3655.

[0099] When Ar3-L5-L4-L3- is replaced by X-1-15 in place of X-3-1, the compound numbers are X-1-15-1 to X-1-15-3655.

[0100] When Ar3-L5-L4-L3- is replaced by X-1-16 in place of X-3-1, the compound numbers are X-1-16-1 to X-1-16-3655.

[0101] When Ar3-L5-L4-L3- is replaced by X-1-17 in place of X-3-1, the compound numbers are X-1-17-1 to X-1-17-3655.

[0102] When Ar3-L5-L4-L3- is replaced by X-1-18 in place of X-3-1, the compound numbers are X-1-18-1 to X-1-18-3655.

[0103] When Ar3-L5-L4-L3- is replaced by X-1-19 in place of X-3-1, the compound numbers are X-1-19-1 to X-1-19-3655.

[0104] When Ar3-L5-L4-L3- is replaced by X-1-20 in place of X-3-1, the compound numbers are X-1-20-1 to X-1-20-3655.

[0105] When Ar3-L5-L4-L3- is replaced by X-1-21 in place of X-3-1, the compound numbers are X-1-21-1 to X-1-21-3655.

[0106] When Ar3-L5-L4-L3- is replaced by X-1-22 in place of X-3-1, the compound numbers are X-1-22-1 to X-1-22-3655.

[0107] When Ar3-L5-L4-L3- is replaced by X-1-23 in place of X-3-1, the compound numbers are X-1-23-1 to X-1-23-3655.

[0108] When Ar3-L5-L4-L3- is replaced by X-1-24 in place of X-3-1, the compound numbers are X-1-24-1 to X-1-24-3655.

[0109] When Ar3-L5-L4-L3- is replaced by X-2-1 in place of X-3-1, the compound numbers are X-2-1-1 to X-2-1-3655.

[0110] When Ar3-L5-L4-L3- is replaced by X-2-2 in place of X-3-1, the compound numbers are X-2-2-1 to X-2-2-3655.

[0111] When Ar3-L5-L4-L3- is replaced by X-2-3 in place of X-3-1, the compound numbers are X-2-3-1 to X-2-3-3655.

[0112] When Ar3-L5-L4-L3- is replaced by X-2-4 in place of X-3-1, the compound numbers are X-2-4-1 to X-2-4-3655.

[0113] When Ar3-L5-L4-L3- is replaced by X-2-5 in place of X-3-1, the compound numbers are X-2-5-1 to X-2-5-3655.

[0114] When Ar3-L5-L4-L3- is replaced by X-2-6 in place of X-3-1, the compound numbers are X-2-6-1 to X-2-6-3655.

[0115] When Ar3-L5-L4-L3- is replaced by X-2-7 in place of X-3-1, the compound numbers are X-2-7-1 to X-2-7-3655.

[0116] When Ar3-L5-L4-L3- is replaced by X-2-8 in place of X-3-1, the compound numbers are X-2-8-1 to X-2-8-3655.

[0117] When Ar3-L5-L4-L3- is replaced by X-2-9 in place of X-3-1, the compound numbers are X-2-9-1 to X-2-9-3655.

[0118] When Ar3-L5-L4-L3- is replaced by X-2-10 in place of X-3-1, the compound numbers are X-2-10-1 to X-2-10-3655.

[0119] When Ar3-L5-L4-L3- is replaced by X-2-11 in place of X-3-1, the compound numbers are X-2-11-1 to X-2-11-3655.

[0120] When Ar3-L5-L4-L3- is replaced by X-2-12 in place of X-3-1, the compound numbers are X-2-12-1 to X-2-12-3655.

[0121] When Ar3-L5-L4-L3- is replaced by X-2-13 in place of X-3-1, the compound numbers are X-2-13-1 to X-2-13-3655.

[0122] When Ar3-L5-L4-L3- is replaced by X-2-14 in place of X-3-1, the compound numbers are X-2-14-1 to X-2-14-3655.

[0123] When Ar3-L5-L4-L3- is replaced by X-2-15 in place of X-3-1, the compound numbers are X-2-15-1 to X-2-15-3655.

[0124] When Ar3-L5-L4-L3- is replaced by X-2-16 in place of X-3-1, the compound numbers are X-2-16-1 to X-2-16-3655.

[0125] When Ar3-L5-L4-L3- is replaced by X-2-17 in place of X-3-1, the compound numbers are X-2-17-1 to X-2-17-3655.

[0126] When Ar3-L5-L4-L3- is replaced by X-2-18 in place of X-3-1, the compound numbers are X-2-18-1 to X-2-18-3655.

[0127] When Ar3-L5-L4-L3- is replaced by X-2-19 in place of X-3-1, the compound numbers are X-2-19-1 to X-2-19-3655.

[0128] When Ar3-L5-L4-L3- is replaced by X-2-20 in place of X-3-1, the compound numbers are X-2-20-1 to X-2-20-3655.

[0129] When Ar3-L5-L4-L3- is replaced by X-2-21 in place of X-3-1, the compound numbers are X-2-21-1 to X-2-21-3655.

[0130] When Ar3-L5-L4-L3- is replaced by X-2-22 in place of X-3-1, the compound numbers are X-2-22-1 to X-2-22-3655.

[0131] When Ar3-L5-L4-L3- is replaced by X-2-23 in place of X-3-1, the compound numbers are X-2-23-1 to X-2-23-3655.

[0132] When Ar3-L5-L4-L3- is replaced by X-2-24 in place of X-3-1, the compound numbers are X-2-24-1 to X-2-24-3655.

[0133] When Ar3-L5-L4-L3- is replaced by X-3-2 in place of X-3-1, the compound numbers are X-3-2-1 to X-3-2-3655.

[0134] When Ar3-L5-L4-L3- is replaced by X-3-3 in place of X-3-1, the compound numbers are X-3-3-1 to X-3-3-3655.

[0135] When Ar3-L5-L4-L3- is replaced by X-3-4 in place of X-3-1, the compound numbers are X-3-4-1 to X-3-4-3655.

[0136] When Ar3-L5-L4-L3- is replaced by X-3-5 in place of X-3-1, the compound numbers are X-3-5-1 to X-3-5-3655.

[0137] When Ar3-L5-L4-L3- is replaced by X-3-6 in place of X-3-1, the compound numbers are X-3-6-1 to X-3-6-3655.

[0138] When Ar3-L5-L4-L3- is replaced by X-3-7 in place of X-3-1, the compound numbers are X-3-7-1 to X-3-7-3655.

[0139] When Ar3-L5-L4-L3- is replaced by X-3-8 in place of X-3-1, the compound numbers are X-3-8-1 to X-3-8-3655.

[0140] When Ar3-L5-L4-L3- is replaced by X-3-9 in place of X-3-1, the compound numbers are X-3-9-1 to X-3-9-3655.

[0141] When Ar3-L5-L4-L3- is replaced by X-3-10 in place of X-3-1, the compound numbers are X-3-10-1 to X-3-10-3655.

[0142] When Ar3-L5-L4-L3- is replaced by X-3-11 in place of X-3-1, the compound numbers are X-3-11-1 to X-3-11-3655.

[0143] When Ar3-L5-L4-L3- is replaced by X-3-12 in place of X-3-1, the compound numbers are X-3-12-1 to X-3-12-3655.

[0144] When Ar3-L5-L4-L3- is replaced by X-3-13, the compound numbers are X-3-13-1 to X-3-13-3655.

[0145] When Ar3-L5-L4-L3- is replaced by X-3-14 in place of X-3-1, the compound numbers are X-3-14-1 to X-3-14-3655.

[0146] When Ar3-L5-L4-L3- is replaced by X-3-15 in place of X-3-1, the compound numbers are X-3-15-1 to X-3-15-3655.

[0147] When Ar3-L5-L4-L3- is replaced by X-3-16 in place of X-3-1, the compound numbers are X-3-16-1 to X-3-16-3655.

[0148] When Ar3-L5-L4-L3- is replaced by X-3-17 in place of X-3-1, the compound numbers are X-3-17-1 to X-3-17-3655.

[0149] When Ar3-L5-L4-L3- is replaced by X-3-18 in place of X-3-1, the compound numbers are X-3-18-1 to X-3-18-3655.

[0150] When Ar3-L5-L4-L3- is replaced by X-3-19 in place of X-3-1, the compound numbers are X-3-19-1 to X-3-19-3655.

[0151] When Ar3-L5-L4-L3- is replaced by X-3-20 in place of X-3-1, the compound numbers are X-3-20-1 to X-3-20-3655.

[0152] When Ar3-L5-L4-L3- is replaced by X-3-21 in place of X-3-1, the compound numbers are X-3-21-1 to X-3-21-3655.

[0153] When Ar3-L5-L4-L3- is replaced by X-3-22 in place of X-3-1, the compound numbers are X-3-22-1 to X-3-22-3655.

[0154] When Ar3-L5-L4-L3- is replaced by X-3-23 in place of X-3-1, the compound numbers are X-3-23-1 to X-3-23-3655.

[0155] When Ar3-L5-L4-L3- is replaced by X-3-24 in place of X-3-1, the compound numbers are X-3-24-1 to X-3-24-3655.

[0156] Furthermore, in an optional embodiment of the present invention, the aromatic amine compound is selected from the following structures:

[0157] According to another aspect of the present invention, the present invention provides a use of the compound as an organic electroluminescent material.

[0158] An organic electroluminescent element comprises 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 comprises the aromatic amine compound described in the present invention.

[0159] 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 aromatic amine compound described in the present invention.

[0160] An electronic device comprises: one or more of a display, a monitor, and a lighting device, including the organic electroluminescent element of the present invention; and a control unit for driving the display device.

[0161] In general, the above technical solutions conceived by the present invention can achieve the following beneficial effects compared with the prior art:

[0162] 1. The aromatic amine compound of the present invention, the compound with a specific core structure of the present invention, when used as an organic electroluminescent material, especially as a hole transport region material, exhibits excellent performance. BRIEF DESCRIPTION OF THE DRAWINGS

[0163] Figure 1 is a schematic structural diagram of the organic electroluminescent element described in Application Example 1; wherein: the numbers in Figure 1 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.

[0164] FIG2 is a mass spectrum (LC-MS) of compound X-3-1-10 prepared in Synthesis Example 12 in Compound Preparation Example. DETAILED DESCRIPTION

[0165] Exemplary embodiments will now be described in detail, examples of which are illustrated in the accompanying drawings, wherein the same reference numerals refer to the same elements throughout. In this regard, the present exemplary embodiments may have different forms and should not be construed as being limited to the description set forth herein. Therefore, exemplary embodiments are described below only with reference to the accompanying drawings to illustrate aspects. As used herein, the term "and / or" includes any and all combinations of one or more of the relevant enumerated items. Expressions such as "at least one (kind)" modify the entire list of elements when before or after a list of elements and do not modify the individual elements of the list.

[0166] 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 intervening elements may be present therebetween. In contrast, when an element is referred to as being “directly on” another element, there are no intervening elements.

[0167] It will be further understood that the terms “comprise” or “comprising” when used in this specification indicate the presence of stated features, regions, integers, steps, operations, elements, and / or components, but do not preclude the presence or addition of one or more additional features, regions, integers, steps, operations, elements, components, and / or combinations thereof.

[0168] 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 context of the relevant art and the present disclosure, and will not be interpreted in an idealized or overly formal sense unless clearly so defined herein.

[0169] The present invention will be further described below in conjunction with specific examples. It should be understood that these examples are intended only to illustrate the present invention and are not intended to limit the scope of protection of the present invention. In addition, it should be understood that after reading the disclosure of the present invention, those skilled in the art may make various changes or modifications to the present invention, and these equivalent forms also fall within the scope of protection defined by the present invention.

[0170] Unless otherwise specified, the experimental methods used in the following examples are conventional methods; the reagents, materials, reaction starting materials, etc. used in the following examples are all commercially available unless otherwise specified.

[0171] The room temperature in the following examples is 25°C.

[0172] Explanation of terms

[0173] As used in the present invention, "Xmn", "Y1...Y85", and "Y1...Y85" are the substituent numbers corresponding to Ar3-L5-L4-L3-, -L1-Ar1, and -L2-Ar2, respectively. The compounds of the present invention can be identified based on the substituents corresponding to these numbers. For example, when m=1 and n=1, Ar3-L5-L4-L3- is selected from the substituents numbered "X-1-1". If -L1-Ar1 is selected from the substituent numbered "Y1" -L2-Ar2 is selected from the substituents numbered "Y1" At this time, the corresponding compound number is X-1-1-1, and the compound structure is

[0174] As used in the present invention, Indicates a replacement position.

[0175] As used in the present invention, It means that the benzene ring in the group is fused to a phenyl group on carbazole on either side. The fused group includes but is not limited to

[0176] As used in the present invention, the above-mentioned A1 is selected from a substituted or unsubstituted C6-C14 aromatic ring, which is derived from a single ring or a combination of two or more aromatic hydrocarbon rings, wherein the number of carbon atoms is the number of ring atoms, excluding the number of carbon atoms in the substituent, wherein the number of ring atoms is Contains the number of carbon atoms C1 and C2;

[0177] The above A2 is selected from substituted or unsubstituted C10-C14 aromatic rings, which are derived from a single ring or a combination of two or more aromatic hydrocarbon rings, and the number of carbon atoms is the number of ring atoms, excluding the number of carbon atoms in the substituents, of which the number of ring atoms is Contains the number of carbon atoms C3 and C4.

[0178] As used herein, the term "halogen group" may include fluorine, chlorine, bromine or iodine.

[0179] As used herein, the abbreviation Bpin represents the group in Indicates the connection location.

[0180] As used herein, the abbreviation Pd2(dba)3 represents the compound trisdibenzylideneacetonedipalladium.

[0181] As used herein, the abbreviation Xphos represents the compound 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl.

[0182] As used herein, the abbreviation Pd(dppf)Cl2 represents the compound (1,1′-bis(diphenylphosphino)ferrocene)palladium dichloride.

[0183] As used herein, the abbreviation t-BuONa refers to the compound sodium tert-butoxide.

[0184] As used herein, the abbreviation SPhos represents the compound 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl.

[0185] As used herein, the term "C6-C14 aromatic ring" refers to an aromatic hydrocarbon ring having 6 to 14 carbon atoms, derived from a single ring or a combination of two or more rings, which may be fused with an adjacent ring, with the carbon atoms shared by the fused ring also being included in the 6 to 14 carbon atoms. The term "C10-C14 aromatic ring" should also be understood in the same manner.

[0186] As used herein, the term "C1-C10 alkyl" refers to a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 10 carbon atoms, examples of which include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl.

[0187] As used herein, 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 cycloalkyl groups include, but are not limited to, cyclopropane, cyclobutane, cyclopentane, cyclohexane, norbornyl, adamantane, and the like.

[0188] As used herein, the term "C2-C10 heterocyclic group" refers to a monovalent substituent derived from a monocyclic or polycyclic ring having 2 to 10 carbon atoms, and the ring contains at least one heteroatom selected from O, S, N, P, and Si.

[0189] As used herein, the term "alkoxy" refers to a straight chain, branched chain, or cyclic chain. The number of carbon atoms in the alkoxy group is not particularly limited, but the alkoxy group preferably has 1 to 10 carbon atoms. Specific examples include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexyloxy, and benzyloxy.

[0190] As used herein, the term "cycloalkenyl" refers to an unsaturated carbon ring, and does not have aromatic character.

[0191] As used herein, the term "heterocycloalkenyl" refers to an unsaturated heterocyclic ring that is not aromatic.

[0192] As used in the present invention, the term "C6-C60 aryl" refers to a monovalent substituent derived from an aromatic hydrocarbon having a monocyclic ring or a combination of two or more rings and having 6 to 60 carbon atoms. Further, such an aryl group may have a form in which two or more rings are simply lateral to each other or fused to each other. Examples of such aryl groups include, but are not limited to, phenyl, biphenyl, naphthyl, phenanthrenyl, anthracenyl, pyrenyl, triphenylene, fluoranthenyl, dimethyl 9,9-dimethylfluorene, 9,9-diphenylfluorene, spirobifluorenyl, etc.

[0193] As used herein, the term "arylene" refers to a divalent aromatic group derived from an "aryl" group by removing a hydrogen atom. For example, a phenyl group can be converted to a phenylene group by removing a hydrogen atom, and a naphthyl group can be converted to a naphthylene group by removing a hydrogen atom.

[0194] As used herein, the term "C3-C60 heteroaryl" 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, preferably 1-3 carbons, in the ring are substituted with a heteroatom, such as N, O, S, P, B or Si. In addition, such heteroaryl groups may have a form in which two or more rings are simply lateral to each other or fused to each other or to an aromatic group. Examples of such heteroaryl groups include, for example, pyrrolyl, furyl, thienyl, benzofuranyl, benzothienyl, carbazolyl, dibenzofuranyl, dibenzothienyl, and the like, but the present invention is not limited thereto.

[0195] As used herein, the term "heteroarylene" refers to a divalent heteroaryl group derived from a "heteroaryl" by removing a hydrogen atom. For example, a pyridyl group can be converted into a pyridylene group by removing a hydrogen atom from a pyridyl group.

[0196] As used herein, "arylamine" includes arylamine, heteroarylamine, and arylheteroarylamine.

[0197] As used in the present invention, the "carbon number is MN" in the expression "a K group having a carbon number of MN" or "a K group of C(MN)" means the carbon number of the K group when it is unsubstituted, and does not include the carbon number of the substituent when it is substituted. For example, a C6-C60 aryl group means that when it is unsubstituted, the number of carbon atoms in the aryl group is any integer between 6 and 60, that is, the carbon number when unsubstituted can be 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20...60.

[0198] 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 the substitution occurs can be the position where the hydrogen atom is replaced. That is, the position is not limited to a specific position, as long as the hydrogen at the position can be replaced by a substituent. For example, carbazolyl includes any of the following groups, but is not limited thereto, unless otherwise specified in this specification:

[0199] "Unsubstituted" means that hydrogen atoms are retained. In this case, hydrogen atoms include protium, deuterium, and tritium. Substitutions may also include substitutions with deuterium and tritium.

[0200] When two or more substituents are present, the two or more substituents may be the same or different.

[0201] As used herein, the term "terphenyl" includes

[0202] As used in the present invention, hydrogen atoms include protium, deuterium, and tritium. The compounds of the present invention may contain deuterium atoms from natural sources, or deuterium atoms may be introduced by deuterating a portion or all of the raw material compounds. If deuterium atoms are introduced from the raw 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 greater than 1%, or greater than 5%, or greater than 10%. If the deuteration rate is not 100%, it represents a mixture of deuterated and undeuterated compounds, or a mixture of a fully deuterated and incompletely deuterated compound, or a mixture of a fully deuterated and undeuterated compound and an incompletely deuterated compound.

[0203] As used in the present invention, terms such as first, second, A, and B are used. The above terms are only used to distinguish components and do not limit the nature or order of the components to which the terms correspond.

[0204] organic electroluminescent elements

[0205] The structure of the organic electroluminescent element of the present invention is a disclosed structure, comprising an anode, a cathode and an organic layer located between the anode and the cathode. The organic layer comprises a light-emitting layer, and at least one layer of the organic layer comprises the compound of the present invention.

[0206] The organic layer further includes 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.

[0207] The light-emitting element of the present invention may emit fluorescence, phosphorescence, or a combination thereof. The light-emitting element may emit light alone or in the form of a series connection of multiple light-emitting units.

[0208] As simple light emitting elements, the following may be mentioned, but are not limited thereto:

[0209] (1) hole transport layer / fluorescent light emitting layer / electron transport layer;

[0210] (2) hole transport layer / phosphorescent light emitting layer / electron transport layer;

[0211] (3) hole transport layer / first fluorescent light-emitting layer / second fluorescent light-emitting layer / electron transport layer;

[0212] (4) hole transport layer / first phosphorescent light-emitting layer / second phosphorescent light-emitting layer / electron transport layer;

[0213] (5) hole transport layer / fluorescent emitting layer / spacer layer / phosphorescent emitting layer / electron transport layer;

[0214] (6) hole transport layer / second hole transport layer / fluorescent light emitting layer / electron transport layer;

[0215] (7) hole transport layer / second hole transport layer / fluorescent light emitting layer / hole blocking layer / electron transport layer;

[0216] (8) hole transport layer / second hole transport layer / phosphorescent light emitting layer / electron transport layer;

[0217] (9) hole transport layer / second hole transport layer / phosphorescent light emitting layer / hole blocking layer / electron transport layer;

[0218] (10) hole injection layer / hole transport layer / phosphorescent light emitting layer / electron transport layer / electron injection layer;

[0219] (11) hole injection layer / hole transport layer / fluorescent light emitting layer / electron transport layer / electron injection layer;

[0220] (12) hole injection layer / hole transport layer / second hole transport layer / phosphorescent light emitting layer / electron transport layer / electron injection layer;

[0221] (13) hole injection layer / hole transport layer / second hole transport layer / fluorescent light emitting layer / electron transport layer / electron injection layer;

[0222] The phosphorescent / fluorescent light-emitting layers may each emit light of a different color.

[0223] As a tandem organic electroluminescent element, it can be an anode / first light-emitting unit / intermediate layer / second light-emitting unit / cathode. The intermediate layer can also generally be called a charge generation layer, an electron extraction layer, a connecting layer, etc. For example, when stacking a fluorescent light-emitting layer and a phosphorescent light-emitting layer, an intermediate layer is placed between the fluorescent light-emitting layer and the phosphorescent light-emitting layer in order to prevent the excitons generated by the phosphorescent light-emitting layer from diffusing to the fluorescent light-emitting layer or to adjust the balance of carriers.

[0224] When the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.

[0225] The organic electroluminescent element of the present specification can be manufactured by using materials and methods known in the art, except that one or more of the organic material layers comprises the compound of the present invention.

[0226] Anode materials may include materials with relatively large work functions, such as transparent conductive oxides, metals, and conductive polymers. Specific examples of anode materials include, but are not limited to, metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; 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; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline.

[0227] Cathode materials typically use materials with a low work function to facilitate electron injection into the organic layer. Examples of cathode materials include metals, metal oxides, and conductive polymers. Specific examples of cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; and multilayer structures such as LiF / Al or LiO2 / Al.

[0228] The hole injection layer (HIL) injects holes from the electrodes and has the ability to transport them. To reduce the energy level difference between the electrodes, the HIL is primarily based on aromatic amine compounds. Other materials include copper phthalocyanine for metal complexes and HATCN (2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene) with a phenylene structure for the lowest unoccupied molecular orbital (LUMO) energy level. When used as a luminescent host and dopant, the aromatic amine compound can be doped with an F4-TCNQ (2,2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanodimethyl-p-benzoquinone) derivative, which has the lowest unoccupied molecular orbital (LUMO) energy level.

[0229] 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 receive holes from the anode or the hole injection layer and transfer the holes to the light-emitting layer. Aromatic amine derivatives, triphenyldiamine derivatives, etc. can be used, and low molecular weight or high molecular weight materials can also be used.

[0230] The second hole transport layer can adjust the energy difference between the hole transport region and the light-emitting layer, which is beneficial for holes to enter the light-emitting layer, while reducing the probability of electrons entering the hole transport region from the light-emitting layer. Aromatic amine derivatives are commonly used.

[0231] A luminescent material is a material that receives holes and electrons from the hole transport layer and electron transport layer, respectively, and combines 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 two or more luminescent materials can be mixed as needed. Both fluorescent and phosphorescent materials can be used as luminescent materials. The luminescent material can be a single-component material or a multi-component material.

[0232] The electron transport layer receives electrons from the electron injection layer and transports the electrons to the light-emitting layer, and the electron transport material can receive electrons from the cathode and transfer the electrons to the light-emitting layer. It is a material with high electron mobility. 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. Metal complexes, and polymer materials and small molecule materials can also be used.

[0233] The electron injection layer is a layer that injects electrons from the electrode.

[0234] Depending on the materials used, the organic light-emitting device of the present specification can be a top-emitting device, a bottom-emitting device, or a dual-emission device.

[0235] The charge generation layer (CGL) is the intermediate layer between the anode and cathode in a tandem-structured device. It generates holes and electrons through charge separation. The CGL typically consists of a P-type layer on the cathode side and an N-type layer on the anode side, enabling efficient charge separation and carrier transport.

[0236] In one embodiment of the present invention, the method for forming each layer is not particularly limited. Conventionally known methods such as vacuum evaporation and spin coating can be used. Each layer, such as the light-emitting layer, can be formed by vacuum evaporation, molecular beam evaporation (MBE), or by a known coating method such as dipping, spin coating, casting, rod coating, or roller coating of a solution dissolved in a solvent.

[0237] In one embodiment of the present invention, the film thickness of each layer is not particularly limited and can generally be several nanometers to several hundred nanometers. In order to suppress defects such as pinholes, reduce driving voltage, and improve luminous efficiency, it is usually preferably in the range of several nm to 1 μm.

[0238] Those skilled in the art can synthesize the compounds of the present invention by referring to the synthesis of the following compounds and known synthesis methods. There are many methods for synthesizing the compounds of the present invention, and the following methods are only illustrative.

[0239] LC-MS brand: Waters, model: SQ Detector 2

[0240] NMR brand: Bruker, model: AVANCE NEO 400

[0241] Those skilled in the art can synthesize the compounds of the present invention by referring to the synthesis of the following compounds and known synthetic methods. An exemplary synthetic formula of the present invention is as follows:

[0242] Synthetic formula 1:

[0243] Synthetic formula 2:

[0244] Wherein, X and Y are each independently a halogen (including F, Cl, Br, I), and those skilled in the art can select them according to the selectivity of the reaction;

[0245] A1, A2, L1-L5, Ar1, Ar2 refer to the definitions in the above embodiments;

[0246] Bpin is Indicates the connection location.

[0247] Synthesis of intermediates

[0248] 1. Synthesis of intermediate 1:

[0249] Step 1: Synthesis of intermediate 1-1

[0250] 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 stirred at 140°C for 6 h. Upon completion of the reaction, heating was discontinued. The liquids were extracted with dichloromethane and water, and the organic phase was dried by spin drying. The sample was then 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%.

[0251] LC-MS (APCI): 372.11 [M+H] +

[0252] Step 2: Synthesis of Intermediate 1

[0253] Under nitrogen, 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-dioxaborane (4.4 g, 13.43 mmol), tetrakis(triphenylphosphine)palladium (310 mg, 0.27 mmol), and potassium carbonate (5.6 g, 40.29 mmol) were placed in a 250 mL four-necked flask. 90 mL of tetrahydrofuran (THF) and 30 mL of deionized water were added. The reaction system was heated to reflux and then stirred for 6 h. The organic phase was extracted with ethyl acetate and water, and the sample was dried by rotary evaporation. The sample was purified by column chromatography (n-hexane:dichloromethane = 10:1 by volume) to obtain 4.2 g of intermediate 1, with a yield of 63%.

[0254] LC-MS (APCI): 494.26 [M+H] +

[0255] 2. Synthesis of Intermediate 2

[0256] Step 1: Synthesis of intermediate 2-1

[0257] Under nitrogen, 2,3-benzocarbazole (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 placed in a 500 mL four-necked flask. 200 mL of N,N-dimethylformamide was added and stirred at 140°C for 6 h. Upon completion of the reaction, heating was discontinued. The liquids were extracted with dichloromethane and water, and the organic phase was dried by rotary evaporation. The sample was then purified by column chromatography (n-hexane:dichloromethane = 30:1) to afford 12 g of intermediate 2-1 in a 46% yield.

[0258] LC-MS (APCI): 372.11 [M+H] +

[0259] Step 2: Synthesis of Intermediate 2

[0260] Under a nitrogen atmosphere, 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-dioxaborane (4.4 g, 13.431 mmol), tetrakis(triphenylphosphine)palladium (310 mg, 0.268 mmol), and potassium carbonate (5.6 g, 40.293 mmol) were placed in a 250 mL four-necked flask. 90 mL of tetrahydrofuran (THF) and 30 mL of deionized water were added. The reaction system was heated to reflux and then stirred for 6 h. After the reaction was completed, the liquid was extracted with ethyl acetate and water. The organic phase was dried by rotary evaporation and 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%.

[0261] LC-MS (APCI): 494.26 [M+H] +

[0262] Synthesis Example:

[0263] Synthesis Example 1: Synthesis of Compound X-2-1-56

[0264] Under a nitrogen atmosphere, 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-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.25 g, 0.6 mmol) and tris(dibenzylideneacetone)dipalladium (0.27 g, 0.3 mmol) were placed in a four-necked reaction flask, 50 mL of toluene was added, and the mixture was heated to reflux. After 2 h of reaction, 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, and then purified by reflux with 60 mL of ethanol to obtain compound X-2-1-56 (4.8 g, 60% yield) as the final product.

[0265] LC-MS (APCI): 793.43 [M+H] +

[0266] 1 H NMR(400MHz,CD2Cl2)δ8.29(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).

[0267] Synthesis Example 2: Synthesis of Compound X-2-5-56

[0268] 1. Synthesis of intermediate T2-1

[0269] Under a nitrogen atmosphere, 2,3-benzocarbazole (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 stirred at 140°C for 6 h. Upon completion of the reaction, heating was discontinued. The organic phase was extracted with dichloromethane and water, and the sample was dried by spin drying. The sample was then purified by column chromatography (volume ratio: n-hexane:dichloromethane = 30:1) to obtain 14 g of intermediate T2-1 in a 54% yield.

[0270] LC-MS (APCI): 372.11 [M+H] +

[0271] 2. Synthesis of intermediate T2-2

[0272] Under nitrogen, 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-dioxaborane (4.4 g, 13.431 mmol), tetrakis(triphenylphosphine)palladium (310 mg, 0.268 mmol), and potassium carbonate (5.6 g, 40.293 mmol) were placed in a 250 mL four-necked flask. 90 mL of THF and 30 mL of deionized water were added. The reaction system was heated to reflux and then stirred for 6 h. The mixture was extracted with ethyl acetate and water. The organic phase was dried and 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%.

[0273] LC-MS (APCI): 494.26 [M+H] +

[0274] 3. Synthesis of compound X-2-5-56

[0275] 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-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.25 g, 0.6 mmol) and tris(dibenzylideneacetone)dipalladium (0.27 g, 0.3 mmol) were placed in a four-necked reaction flask, 50 mL of toluene was added, and the mixture was heated to reflux. After 2 h of reaction, 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, and then purified by reflux with 60 mL of ethanol to obtain compound X-2-5-56 (5.6 g, 70% yield) as the final product.

[0276] LC-MS (APCI): 793.43 [M+H] +

[0277] 1 H NMR(400MHz,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).

[0278] Synthesis Example 3: Synthesis of Compound X-3-1-28

[0279] 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 placed in a four-necked reaction flask. 50 ml of toluene was added, and the mixture was heated to 110°C for reaction. After completion of the reaction, the reaction solution was cooled to room temperature, extracted with dichloromethane, dried over anhydrous sodium sulfate, and the solvent was removed. The solution was purified by column chromatography (developing solvent volume ratio: n-hexane:dichloromethane = 3:1). This yielded compound X-3-1-28 (9 g, 88% yield) as the final product.

[0280] LC-MS (APCI): 753.41 [M+H] +

[0281] 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).

[0282] Synthesis Example 4: Synthesis of Compound X-3-1-277

[0283] 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 reacted at 90°C for 4 h. After completion of the reaction, the reaction solution was extracted with dichloromethane, dried over anhydrous sodium sulfate, and the solvent was removed. Crystallization was performed using ethyl acetate (for purification). This gave compound X-3-1-277 (12 g, yield: 77%) as the final product.

[0284] LC-MS (APCI): 830.50 [M+H] +

[0285] 1 H 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).

[0286] Synthesis Example 5: Synthesis of Compound X-3-2-26

[0287] 1. Synthesis of intermediate T5-1

[0288] To a 500ml four-necked flask, 4-bromo-1-chlorodibenzo[b,d]furan (10.0g, 35.52mmol), 3-(naphthalen-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), and toluene (200ml) were added sequentially. The mixture was refluxed under nitrogen for 3 hours. After completion of the reaction, the mixture was purified by column chromatography (n-hexane:dichloromethane = 10:1) to obtain intermediate T5-1 (14.7g, 83.7% yield).

[0289] LC-MS:496.30[M+H] +

[0290] 2. Synthesis of compound X-3-2-26

[0291] To a 500ml four-necked flask, intermediate T5-1 (14.7g, 29.75mmol), (2-(7H-benzo[c]carbazol-7-yl)phenyl)boronic acid (10.0g, 29.75mmol), Pd(dppf)Cl2 (435mg, 0.595mmol), potassium carbonate (8.2g, 59.5mmol), toluene (150ml), ethanol (50ml), and water (50ml) were added in sequence. The mixture was refluxed under nitrogen for 6 hours. After completion of the reaction, the mixture was purified by column chromatography (n-hexane:dichloromethane = volume ratio 5:1) to obtain the final product, compound X-3-2-26 (18.7g, yield: 83.4%).

[0292] LC-MS:753.41[M+H] +

[0293] 1 H NMR(400MHz,Methylene Chloride-d2)δ8.73(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).

[0294] Synthesis Example 6: Synthesis of Compound X-3-1-88

[0295] Under a nitrogen atmosphere, N-(4-biphenyl)-2-benzidine (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 reacted at 90°C for 4 h. After completion of the reaction, the reaction solution was extracted with dichloromethane, dried over anhydrous sodium sulfate, and the solvent was removed. Crystallization was performed using ethyl acetate (for purification). This gave the final product, compound X-3-1-88 (12 g, yield: 82%).

[0296] LC-MS (APCI): 779.98 [M+H] +

[0297] 1 H NMR(400MHz,Methylene Chloride-d2)δ8.56(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).

[0298] Synthesis Example 7: Synthesis of Compound X-3-1-283

[0299] 1. Synthesis of intermediate T7-1

[0300] Under nitrogen, 9-(3-chlorophenyl)phenanthrene (15 g, 51.9 mmol), 4-aminobiphenyl (9.7 g, 57.3 mmol), sodium tert-butoxide (9.9 g, 103 mmol), tris(dibenzylideneacetone)dipalladium (0.95 g, 1 mmol), and 2-dicyclohexylphosphine-2′,6′-dimethoxy-biphenyl (0.85 g, 2 mmol) were added to a four-necked reaction flask. Anhydrous toluene (125 ml) was then added and the reaction was heated to 110°C. Upon completion of the reaction, heating was stopped, the reaction mixture was cooled to room temperature, and quenched with 100 ml of water. The reaction mixture was extracted with 100 ml of dichloromethane. The organic phase was separated, washed three times with water, dried over anhydrous sodium sulfate, filtered, and spin-dried to obtain 21.3 g of a viscous solid. The solid was separated by column chromatography using a 20:1 volume ratio of n-hexane to ethyl acetate as the eluent. 15 g of crude product T7-1 was obtained, which was then refluxed with ethanol:ethyl acetate = 5:1 to obtain intermediate T7-1 (14 g, yield 63.9%).

[0301] LC-MS (APCI): 422.44 [M+H] +

[0302] 2. Synthesis of compound X-3-1-283

[0303] Under nitrogen, intermediate T7-1 (6 g, 12.1 mmol), intermediate 1 (4.7 g, 11.1 mmol), sodium tert-butoxide (1.95 g, 20.2 mmol), tris(dibenzylideneacetone)dipalladium (0.95 g, 0.2 mmol), and tri-tert-butylphosphine (0.85 g, 2 mmol) were added to a four-necked reaction flask. Anhydrous toluene (125 ml) was then added and the mixture was heated to 110°C. Upon completion of the reaction, heating was discontinued, the mixture was cooled to room temperature, and quenched with 100 ml of water. The reaction mixture was extracted with 100 ml of dichloromethane. The organic phase was separated, washed three times with water, dried over anhydrous sodium sulfate, filtered, and the organic phase was spin-dried to afford 15 g of a black solid. The product was separated by column chromatography using a 10:1 volume ratio of hexane to dichloromethane to afford compound X-3-1-283 (8.3 g, 78.3% yield).

[0304] LC-MS (APCI): 880.65 [M+H] +

[0305] 1H NMR(400MHz,Methylene Chloride-d2)δ8.63(ddd,2H),8.14(s,1H),7.94–7.87(m,1H),7.84–7.62(m,6H),7.61–7.38(m,9 H),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).

[0306] Synthesis Example 8: Synthesis of Compound X-3-1-11

[0307] Under a nitrogen atmosphere, N-phenyl[1,1′:3′,1′-triphenyl]-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 with a developing solvent of n-hexane:dichloromethane (volume ratio: 3:1). Compound X-3-1-11 (5.1 g, 43% yield) was obtained as a white solid.

[0308] LC-MS (APCI): 779.61 [M+H] +

[0309] 1 H NMR(400MHz,DMSO-d6)δ8.61(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).

[0310] Synthesis Example 9: Synthesis of Compound X-3-1-59

[0311] 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), tetrakistriphenylphosphine palladium (346 mg, 0.30 mmol), and sodium tert-butoxide (2.9 g, 30.4 mmol) were placed in a four-necked reaction flask. 150 ml of toluene was then added, and the temperature was raised to reflux for 4 hours. After completion of the reaction, the mixture was filtered, the filter cake washed with water, and then refluxed with 100 ml of ethyl acetate for 30 minutes before filtration to obtain the final product, compound X-3-1-59 (9.6 g, 77% yield).

[0312] LC-MS (APCI): 811.59 [M+H] +

[0313] 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).

[0314] Synthesis Example 10: Synthesis of Compound X-2-5-28

[0315] 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 placed in a four-necked reaction flask. 50 mL of toluene was then added, and the mixture was heated to reflux. After 2 h of reaction, the reaction solution was cooled to room temperature and flash column purified with toluene to obtain compound X-2-5-28 (5 g, 68% yield) as the final product.

[0316] LC-MS (APCI): 753.48 [M+H] +

[0317] 1H NMR(400MHz,Methylene Chloride-d2)δ8.56(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).

[0318] Synthesis Example 11: Synthesis of Compound X-3-1-78

[0319] 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-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.4 g, 1.0 mmol) and tris(dibenzylideneacetone)dipalladium (0.18 g, 0.2 mmol) were placed in a four-necked reaction flask, 50 mL of toluene was added, and the mixture was heated to reflux. After 3 h of reaction, 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, and then purified by reflux 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, 53% yield) as the final product.

[0320] LC-MS (APCI): 793.50 [M+H] + .

[0321] 1 H NMR(400MHz,Methylene Chloride-d2)δ8.33(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).

[0322] Synthesis Example 12: Synthesis of Compound X-3-1-10

[0323] 1. Synthesis of intermediate T12-1

[0324] To a 2L four-necked flask, 4-bromo-N-phenylaniline (12.00 g, 0.0483 mol) and 3-biphenylboronic acid (11.49 g, 0.0582 mol) were added sequentially. Potassium carbonate (6.68 g, 0.0725 mol) and bistriphenylphosphine palladium dichloride (0.68 g, 0.967 mmol) were then added. Tetrahydrofuran (120 ml) and water (30 ml) were then added. The reaction was incubated at 75°C under nitrogen for 15 h. After completion of the reaction, the temperature was lowered to 25°C, the mixture was quenched with water, and the organic phase was separated. The organic phase was spin-dried and recrystallized from ethyl acetate to afford Intermediate T12-1 (9.5 g, 61.1% yield).

[0325] LC-MS (APCI): 322.57 [M+H] + .

[0326] 2. Synthesis of compound X-3-1-10

[0327] To a 250ml four-necked flask, intermediate T12-1 (4.5g, 0.014mol), intermediate 1 (8.3g, 0.017mol), potassium carbonate (2.69g, 0.028mol), tris(dibenzylideneacetone)dipalladium (0.13g, 0.14mmol), and 2-dicyclohexylphosphine-2',6'-dimethoxy-biphenyl (0.23g, 0.556mmol) were added in sequence, followed by toluene (100ml). The reaction was carried out at 95°C under nitrogen for 16h. After completion of the reaction, the temperature was lowered to 25°C, the reaction was quenched with water, and the organic phase was separated. The organic phase was spin-dried and slurried with ethyl acetate to obtain the final product, compound X-3-1-10 (3.5g, 32.0% yield).

[0328] LC-MS (APCI): 779.58 [M+H] + ; For the corresponding mass spectrum, see Figure 2 of the specification.

[0329] 1 H NMR(400MHz,Methylene Chloride-d2)δ8.54(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).

[0330] Synthesis Example 13: Synthesis of Compound X-3-1-9

[0331] 1. Synthesis of intermediate T13-2

[0332] Under nitrogen, intermediate T13-1 (6 g, 12.3 mmol), aniline (2.2 g, 12.6 mmol), t-BuONa (2.5 g, 24.9 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.4 g, 1.0 mmol), and tris(dibenzylideneacetone)dipalladium (0.18 g, 0.2 mmol) were placed in a four-necked reaction flask. 60 mL of toluene was added and the mixture was heated to reflux. After 2 h of reaction, the reaction solution was cooled to room temperature and the organic phase was extracted with dichloromethane. The organic phase was then dried and purified by chromatography (n-hexane:dichloromethane = 5:1) to obtain intermediate T13-2 (6.2 g, 88% yield).

[0333] LC-MS (APCI): 322.30 [M+H] + .

[0334] 2. Synthesis of compound X-3-1-9

[0335] Under nitrogen, intermediate T13-2 (5.0 g, 13.2 mmol), intermediate 1 (3.6 g, 13.6 mmol), t-BuONa (2 g, 26 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.4 g, 1.0 mmol), and tris(dibenzylideneacetone)dipalladium (0.18 g, 0.2 mmol) were placed in a four-necked reaction flask. 50 mL of toluene was added, and the mixture was heated to reflux. After 2 h of reaction, the reaction solution was cooled to room temperature and passed through a flash chromatography column with toluene to obtain compound X-3-1-9 (6.2 g, 72% yield) as the final product.

[0336] LC-MS (APCI): 779.58 [M+H] +

[0337] 1H NMR(400MHz,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).

[0338] Synthesis Example 14: Synthesis of Compound T14

[0339] 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-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.4 g, 1.0 mmol), and tris(dibenzylideneacetone)dipalladium (0.18 g, 0.2 mmol) were placed in a four-necked reaction flask. 50 mL of toluene was added, and the mixture was heated to reflux. After 2 h of reaction, 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 spin-drying, and then purified by reflux with 50 mL of ethyl acetate to obtain the final product, compound T14 (4.2 g, 55% yield).

[0340] LC-MS (APCI): 758.49 [M+H] +

[0341] 1 H NMR(400MHz,Methylene Chloride-d2)δ8.52(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).

[0342] Synthesis Example 15: Synthesis of Compound X-3-1-170

[0343] 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 placed in a four-necked reaction flask. 50 mL of toluene was added, and the mixture was heated to reflux. After 2 h of reaction, the reaction solution was cooled to room temperature and purified by chromatography (n-hexane:dichloromethane = 5:1) to obtain compound X-3-1-170 (5.0 g, 41.7% yield) as the final product.

[0344] LC-MS (APCI): 779.42 [M+H] + .

[0345] 1 H NMR(400MHz,Methylene Chloride-d2)δ8.56(d,J=8.3Hz,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=8.2,6.7,1.3Hz, 1H),7.50(d,J=8.9Hz,1H),7.42–7.29(m,8H),7.28–7.16(m,8H),7.09–7 .00(m,5H),6.96(t,J=7.9Hz,1H),6.90–6.76(m,3H),6.53–6.43(m,4H).

[0346] Synthesis Example 16: Synthesis of Compound X-3-1-17

[0347] Under a nitrogen atmosphere, to a 250 ml four-necked flask were added intermediate T16-1 (4.5 g, 14.0 mol), intermediate 1 (8.3 g, 16.8 mol), potassium carbonate (4.92 g, 28 mol), tris(dibenzylideneacetone)dipalladium (0.13 g, 0.14 mmol), and 2-dicyclohexylphosphine-2′,6′-dimethoxy-biphenyl (0.23 g, 0.556 mmol), followed by 100 ml of toluene. The mixture was reacted at 95°C for 16 h. The reaction solution was cooled to room temperature and purified by chromatography (n-hexane:dichloromethane = 4:1). The final product, compound X-3-1-17 (3.85 g, 35.2% yield), was obtained by slurrying.

[0348] LC-MS:779.39[M+H] + .

[0349] 1 H NMR (400 MHz, Methylene Chloride-d2)δ8.66(d,J=8.3Hz,1H),8.42(dd,J=6.1,3.1Hz,1H),8.07–7.99( m,1H),7.93(dd,J=8.2,1.3Hz,1H),7.86–7.74(m,3H),7.71–7.63(m,5H),7.61– 7.54(m,3H),7.47(t,J=7.7Hz,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=7.6,1.7Hz,2H),6.65–6.51(m,3H).

[0350] Synthesis Example 17: Synthesis of Compound X-3-1-35

[0351] Under a nitrogen atmosphere, Intermediate T17-1 (4.7 g, 13.54 mmol), Intermediate 1 (6.4 g, 12.89 mmol), trisdibenzylideneacetone dipalladium (354 mg, 0.386 mmol), 2-dicyclohexylphosphine-2,6-dimethoxybiphenyl (530 mg, 1.20 mmol), and sodium tert-butoxide (2.5 g, 25.78 mmol) were placed in a 250 mL four-necked flask. 100 mL of toluene was added, and the reaction system was heated to reflux and then stirred for 5 hours. After the reaction was completed, the reaction solution was cooled to room temperature. The organic phases were extracted with dichloromethane and water, and the combined organic phases were dried over silica gel and purified by column chromatography (hexane:dichloromethane = 5:1) to obtain the final product, X-3-1-35 (6.8 g, 65.7% yield).

[0352] LC-MS (APCI): 803.56 [M+H] + .

[0353] 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,1 H),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).

[0354] Synthesis Example 18: Synthesis of Compound X-3-1-56

[0355] 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-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.3 g, 0.7 mmol) and tris(dibenzylideneacetone)dipalladium (0.33 g, 0.37 mmol) were placed in a four-necked reaction flask, 60 mL of toluene was added, and the mixture was heated to reflux. After 2 h of reaction, 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, and then purified by reflux with 60 mL of ethanol to obtain compound X-3-1-56 (7.1 g, 74% yield) as the final product.

[0356] LC-MS (APCI): 793.43 [M+H] +

[0357] 1 H NMR(400MHz, CD2Cl2)δ8.56(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).

[0358] Synthesis Example 19: Synthesis of Compound X-3-1-30

[0359] 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 placed in a 250 mL four-necked flask. 100 mL of toluene was added and the reaction system was heated to reflux. After 5 h of reaction, 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 by column chromatography (developing solvent volume ratio: n-hexane:dichloromethane = 3:1) afforded compound X-3-1-30 (5.4 g, 59.1% yield) as a white solid.

[0360] LC-MS (APCI): 753.37 [M+H] +

[0361] 1 H NMR(400MHz,Methylene Chloride-d2)δ8.70(d,J=8.3Hz,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= 8.9Hz,1H),7.57–7.48(m,4H),7.40–7.32(m,3H),7.31–7.26(m,2H),7.2 2–7.06(m,4H),7.01–6.90(m,4H),6.82–6.76(m,2H),6.68–6.57(m,3H).

[0362] The following application examples further illustrate the application of the aromatic amine compound of the present invention in the preparation of organic electroluminescent devices.

[0363] Application Example 1:

[0364] This embodiment provides an organic electroluminescent element, as shown in FIG1 , comprising 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 constitute the hole transport region, while the hole blocking layer 7 and the electron transport layer 8 constitute the electron transport region.

[0365] The specific device structure is:

[0366] ITO / HT1-PD3%(10nm) / HT1(60nm) / HT2(5nm) / BH-BD3%(20nm) / HB(5nm) / ET-LiQ50%(30nm) / Mg:Ag 1:9(100nm)

[0367] Device preparation process:

[0368] The bottom-emitting glass substrate 1 used in this embodiment was purchased from Guangdong Xinli Display Technology Co., Ltd., and ITO was used as the anode 2. First, the bottom-emitting glass substrate was cleaned using an ITO cleaner, deionized water, and isopropyl alcohol in that order, and then baked at 180 degrees Celsius for 30 minutes to dry it.

[0369] Then put the bottom luminescent glass substrate into the evaporation chamber and -8 The organic layers were sequentially deposited on the ITO anode by thermal vacuum evaporation at a rate of 0.2-2 angstroms / second under the conditions of 100 nm. HT1 was doped with 3% PD to form a 10nm thick hole injection layer 3, HT1 was formed to a 60nm thickness as the first hole transport layer 4, HT2 was evaporated on HT1 to a 5nm thickness as the second hole transport layer 5, the anthracene host BH was doped with 3% BD to form a 20nm thick blue light-emitting layer 6, HB was formed to a 5nm thickness as the hole blocking layer 7, ET was doped with 50% Liq to form a 30nm thick electron transport layer 8, and Mg:Ag (1:9) was formed to a 100nm thickness 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, which is recorded as organic electronic component 1. In the embodiment of the device, different materials are co-evaporated in the same layer and exist in a certain volume ratio in the layer, for example, 50% Liq is ET50% and Liq50% by volume. The compound of the present invention is used after purification by sublimation, HPLC: 99.9%.

[0370] The specific structures of the compounds involved are as follows. The synthesis of HT2 can refer to the synthesis method of intermediate 2 and synthesis example 1, except that the starting material 2,3-benzocarbazole is replaced with carbazole in the intermediate 2 step. LC-MS (APCI): 744.59 (M+H + ).

[0371] Examples and Comparative Examples

[0372] The compound X-2-1-56 prepared in Synthesis Example 1 of the present invention was used instead of HT2 to prepare the second hole transport layer, and the organic electronic component 2 was prepared using the same method.

[0373] The compound X-2-5-56 prepared in Synthesis Example 2 of the present invention was used instead of HT2 to prepare the second hole transport layer, and the organic electronic component 3 was prepared using the same method.

[0374] The compound X-3-1-28 prepared in Synthesis Example 3 of the present invention was used instead of HT2 to prepare the second hole transport layer, and the organic electronic component 4 was prepared using the same method.

[0375] The compound X-3-1-277 prepared in Synthesis Example 4 of the present invention was used instead of HT2 to prepare the second hole transport layer, and the organic electronic component 5 was prepared using the same method.

[0376] The compound X-3-2-26 prepared in Synthesis Example 5 of the present invention was used instead of HT2 to prepare the second hole transport layer, and the organic electronic component 6 was prepared using the same method.

[0377] The second hole transport layer was prepared using the compound X-3-1-88 prepared in Synthesis Example 6 of the present invention instead of HT2, and the organic electronic component 7 was prepared using the same method.

[0378] The compound X-3-1-283 prepared in Synthesis Example 7 of the present invention was used instead of HT2 to prepare the second hole transport layer, and the organic electronic component 8 was prepared using the same method.

[0379] The second hole transport layer was prepared using the compound X-3-1-11 obtained in Synthesis Example 8 of the present invention instead of HT2, and the organic electronic component 9 was prepared using the same method.

[0380] The second hole transport layer was prepared using the compound X-3-1-59 obtained in Synthesis Example 9 of the present invention instead of HT2, and the organic electronic component 10 was prepared using the same method.

[0381] The second hole transport layer was prepared using the compound X-2-5-28 prepared in Synthesis Example 10 of the present invention instead of HT2, and the organic electronic component 11 was prepared using the same method.

[0382] The second hole transport layer was prepared using the compound X-3-1-78 obtained in Synthesis Example 11 of the present invention instead of HT2, and the organic electronic component 12 was prepared using the same method.

[0383] The second hole transport layer was prepared using the compound X-3-1-10 obtained in Synthesis Example 12 of the present invention instead of HT2, and the organic electronic component 13 was prepared using the same method.

[0384] The second hole transport layer was prepared using the compound X-3-1-9 obtained in Synthesis Example 13 of the present invention instead of HT2, and the organic electronic component 14 was prepared using the same method.

[0385] The second hole transport layer was prepared using compound T14 (partially deuterated X-3-1-28) obtained in Synthesis Example 14 of the present invention instead of HT2, and the organic electronic component 15 was prepared using the same method.

[0386] The second hole transport layer was prepared using the compound X-3-1-170 obtained in Synthesis Example 15 of the present invention instead of HT2, and the organic electronic component 16 was prepared using the same method.

[0387] The second hole transport layer was prepared using compound X-3-1-17 obtained in Synthesis Example 16 of the present invention instead of HT2, and the organic electronic component 17 was prepared using the same method.

[0388] The second hole transport layer was prepared using the compound X-3-1-35 obtained in Synthesis Example 17 of the present invention instead of HT2, and the organic electronic component 18 was prepared using the same method.

[0389] The second hole transport layer was prepared using compound X-3-1-56 obtained in Synthesis Example 18 of the present invention instead of HT2, and the organic electronic component 19 was prepared using the same method.

[0390] The second hole transport layer was prepared using the compound X-3-1-30 prepared in Synthesis Example 19 of the present invention instead of HT2, and the organic electronic component 20 was prepared using the same method.

[0391] Organic electroluminescent element evaluation

[0392] IVL test instrument: F STAR Optical Measurement Systems, model: FS-2000GA4; atmospheric environment, room temperature.

[0393] Current efficiency at current density 15mA / cm 2 Next test.

[0394] The driving voltage is at a current density of 15 mA / cm 2 Next test.

[0395] The organic electroluminescent elements 2-20 and organic electronic element 1 prepared by the compounds of the present application, the compounds with benzocarbazole structure and phenylene-dibenzofuran structure have strong hole transport capabilities, can quickly transfer holes to the light-emitting layer, and at the same time have suitable energy levels, can confine carriers within the light-emitting layer, and reduce the efficiency drop caused by carrier overflow. The organic electroluminescent elements prepared by the compounds of the present application have lower driving voltage and higher current efficiency. Therefore, the compounds of the present invention are suitable for preparing high-performance organic electroluminescent elements.

[0396] It will be easily understood by those skilled in the art that the above description is only a preferred embodiment of the present invention and is not intended to limit the present invention. Any modifications, equivalent substitutions and improvements made within the spirit and principles of the present invention should be included in the scope of protection of the present invention.

Claims

1. An aromatic amine compound, characterized in that, The compound has the structure shown in formula (1), Among them, Ar3 has the following structure: Indicates 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", when substituted, the substituents 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 arylamine 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 when substituted in the "substituted or unsubstituted" is the same as that defined in claim 1.

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

4. The arylamine compound according to claim 1, wherein The aromatic amine compound has the structures shown in formulas (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 an integer between 0 and 6; when c is 2 or greater, multiple R3s are the same 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 arylamine compound according to claim 1, wherein The aromatic amine compound has the structure shown in formulas (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 an integer selected from 0 to 4; when a is 2 or greater, the multiple R1s are the same as or different from each other; b is an integer selected from 0 to 10; when b is 2 or greater, the multiple R2s are the same as or different from each other; c is an integer selected from 0 to 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, Each of L1 and L2 is independently selected from a single bond, a substituted or unsubstituted group as follows: The definition of the substituent when "substituted or unsubstituted" is substituted is the same as that defined in claim 1.

7. The arylamine compound according to any one of claims 1-5, characterized in that, Ar1 and Ar2 are each independently selected from hydrogen and the following substituted or unsubstituted groups: 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, characterized in that The 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 referred to by X-1-1 to X-1-24, X-2-1 to X-2-24, and X-3-1 to X-3-24.

9. The arylamine compound according to claim 8, wherein The -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 arylamine compound according to claim 9, wherein The aromatic amine compound is selected from the following structures: Among them, 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 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, 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, When Ar3-L5-L4-L3- is replaced with X-1-6 for X-3-1, the compound numbers are X-1-6-1 to X-1-6-3655, When Ar3-L5-L4-L3- is replaced with X-1-7 for X-3-1, the compound numbers are X-1-7-1 to X-1-7-3655, When Ar3-L5-L4-L3- is replaced with X-1-8 for X-3-1, 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 with 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 with 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 with 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 with 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 with X-2-2 in Ar3-L5-L4-L3, the compound numbers are X-2-2-1 to X-2-2-3655, When replacing X-3-1 with X-2-3 in Ar3-L5-L4-L3, the compound numbers are X-2-3-1 to X-2-3-3655, When replacing X-3-1 with X-2-4 in Ar3-L5-L4-L3, the compound numbers are X-2-4-1 to X-2-4-3655, When replacing X-3-1 with X-2-5 in Ar3-L5-L4-L3, the compound numbers are X-2-5-1 to X-2-5-3655, When replacing X-3-1 with X-2-6 in Ar3-L5-L4-L3, the compound numbers are X-2-6-1 to X-2-6-3655, When replacing X-3-1 with X-2-7 in Ar3-L5-L4-L3, the compound numbers are X-2-7-1 to X-2-7-3655, When replacing X-3-1 with X-2-8 in Ar3-L5-L4-L3, the compound numbers are X-2-8-1 to X-2-8-3655, When replacing X-3-1 with X-2-9 in Ar3-L5-L4-L3, the compound numbers are X-2-9-1 to X-2-9-3655, When replacing X-3-1 with X-2-10 in Ar3-L5-L4-L3, the compound numbers are X-2-10-1 to X-2-10-3655, When replacing X-3-1 with X-2-11 in Ar3-L5-L4-L3, the compound numbers are X-2-11-1 to X-2-11-3655, When replacing X-3-1 with X-2-12 in Ar3-L5-L4-L3, the compound numbers are X-2-12-1 to X-2-12-3655, When replacing X-3-1 with X-2-13 in Ar3-L5-L4-L3, the compound numbers are X-2-13-1 to X-2-13-3655, When replacing X-3-1 with X-2-14 in Ar3-L5-L4-L3, the compound numbers are X-2-14-1 to X-2-14-3655, When replacing X-3-1 with X-2-15 in Ar3-L5-L4-L3, the compound numbers are X-2-15-1 to X-2-15-3655, When replacing X-3-1 with X-2-16 in Ar3-L5-L4-L3, the compound numbers are X-2-16-1 to X-2-16-3655, When replacing X-3-1 with X-2-17 in Ar3-L5-L4-L3, the compound numbers are X-2-17-1 to X-2-17-3655, When replacing X-3-1 with X-2-18 in Ar3-L5-L4-L3, the compound numbers are X-2-18-1 to X-2-18-3655, When replacing X-3-1 with X-2-19 in Ar3-L5-L4-L3, the compound numbers are X-2-19-1 to X-2-19-3655, When replacing X-3-1 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 with 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 with 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 with 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 with 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 with X-3-15 in Ar3-L5-L4-L3, the compound numbers are X-3-15-1 to X-3-15-3655, When replacing X-3-1 with X-3-16 in Ar3-L5-L4-L3, the compound numbers are X-3-16-1 to X-3-16-3655, When replacing X-3-1 with X-3-17 in Ar3-L5-L4-L3, the compound numbers are X-3-17-1 to X-3-17-3655, When replacing X-3-1 with X-3-18 in Ar3-L5-L4-L3, the compound numbers are X-3-18-1 to X-3-18-3655, 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, 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, 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, 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, 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, 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.

11. The arylamine compound according to claim 9, wherein The arylamine 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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