Organic electroluminescent compound and application thereof

Abstract

The invention relates to the technical field of display, in particular to an organic electroluminescent compound and application thereof. The organic electroluminescent compound provided by the invention has the structure as shown in the formula (1), so that the organic electroluminescent device containing the organic electroluminescent compound has relatively low driving voltage, relatively high current efficiency and relatively long service life.

Description

Technical Field

[0001] This invention belongs to the field of organic electroluminescence technology, specifically relating to an organic electroluminescent compound and its applications. Background Technology

[0002] Electroluminescent devices (EL devices) are self-emissive devices that offer advantages such as a wider viewing angle, higher contrast ratio, and faster response time. Organic EL devices (OLEDs) convert electrical energy into light by applying electricity to organic electroluminescent materials and generally have a structure comprising an anode, a cathode, and an organic layer between the anode and cathode. The organic layer of an organic EL device can consist of a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer (containing a host material and dopants), an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer, etc. The materials used in the organic layer are classified according to their function as hole injection materials, hole transport materials, electron blocking materials, light-emitting materials, electron buffer materials, hole blocking materials, electron transport materials, and electron injection materials, etc. In the organic EL device, due to the application of voltage, holes are injected from the anode into the light-emitting layer, and electrons are injected from the cathode into the light-emitting layer, and high-energy excitons are formed through the recombination of holes and electrons. With this energy, the organic light-emitting compound reaches an excited state, and light is emitted by the energy generated by the return of the organic light-emitting compound from the excited state to the ground state.

[0003] The most important factor determining the luminescent efficiency of organic EL devices is the luminescent material. The luminescent material must possess high quantum efficiency and high electron and hole mobility, and the resulting luminescent material layer must be uniform and stable. Specifically, considering the EL characteristic requirements of OLEDs for medium or large-sized panels, it is necessary to develop materials that can exhibit better characteristics than conventional materials. However, the HOMO and LUMO energy levels of existing organic electroluminescent materials have poor matching with adjacent energy levels, leading to low stability and unbalanced carrier mobility. This results in organic electroluminescent devices containing such materials having high driving voltage, low luminescent efficiency, and short lifetime, severely limiting the application of organic electroluminescent devices. Summary of the Invention

[0004] The purpose of this invention is to overcome the problems in related technologies where the HOMO and LUMO energy levels of organic electroluminescent materials have poor matching with adjacent energy levels, resulting in low stability and unbalanced carrier mobility of the organic electroluminescent materials. This leads to problems such as high driving voltage, low luminous efficiency, and short lifetime of organic electroluminescent devices containing such materials. In this way, an organic electroluminescent compound and its application are provided.

[0005] This invention provides an organic electroluminescent compound having the structure shown in formula (1):

[0006]

[0007] In the formula,

[0008] X1, X2, and X3 are each independently selected from O, S, or NR2;

[0009] L1, L2, and L3 are each independently selected from single-bonded or substituted or unsubstituted C6-C60 arylene groups;

[0010] Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted C6-C60 aryl or substituted or unsubstituted C1-C60 heteroaryl;

[0011] R1 and R2 may be the same or different, and each is independently selected from hydrogen, deuterium, halogen, hydroxyl, nitro, amidine, hydrazine, substituted or unsubstituted C1-C60 alkyl, substituted or unsubstituted C2-C60 alkenyl, substituted or unsubstituted C2-C60 alkynyl, substituted or unsubstituted C3-C60 cycloalkyl, substituted or unsubstituted C1-C60 heterocycloalkyl, substituted or unsubstituted C3-C60 cycloalkenyl, substituted or unsubstituted C1-C60 heterocycloalkenyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C1-C60 heteroaryl;

[0012] Ring A is selected from substituted or unsubstituted C6-C60 aromatic rings or substituted or unsubstituted C3-C60 heteroaromatic rings;

[0013] n is an integer selected from 0 to 3;

[0014] The substituted C1-C60 alkyl, substituted C2-C60 alkenyl, substituted C2-C60 ynyl, substituted C3-C60 cycloalkyl, substituted C1-C60 heterocycloalkyl, substituted C3-C60 cycloalkenyl, substituted C1-C60 heterocycloalkenyl, substituted C6-C60 aryl, substituted C6-C60 arylene, substituted C1-C60 heteroaryl, substituted C6-C60 aromatic ring, and The substituents in the substituted C3-C60 heteroaryl ring are selected from one or more of the following: deuterium, halogen, cyano, hydroxyl, nitro, amido, hydrazine, C1-C60 alkyl, C2-C60 alkenyl, C3-C60 cycloalkyl, C2-C60 alkynyl, C3-C60 cycloalkyl, C1-C60 heterocyclic alkyl, C3-C60 cycloalkenyl, C1-C60 heterocyclic alkenyl, C6-C60 aryl, and C1-C60 heteroaryl.

[0015] Substituents

[0016] In this application, the term "substituent" has its common meaning as known in the art, referring to a chemical moiety covalently attached to or, where appropriate, fused to a parent nucleus group.

[0017] Replaced or not replaced

[0018] In this application, the term "substituted or unsubstituted" means that the functional group described after the term may or may not have substituents (hereinafter, for ease of description, substituents are collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to an aryl group having a substituent Rc or an unsubstituted aryl group. The aforementioned substituent, i.e., Rc, can be, for example, deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, or C1-C60 heteroaryl. Optionally, it can be, for example, deuterium, a halogen group, cyano, alkyl, haloalkyl, trialkylsilyl, deuterated alkyl, aryl, heteroaryl, etc. Of course, the number of substituents Rc can be one or more. When two substituents Rc are attached to the same atom, the two substituents Rc can exist independently or be connected to each other to form a ring with the atom; when two adjacent substituents Rc exist on a functional group, the adjacent substituents Rc can exist independently or fuse with the functional group to which they are attached to form a ring.

[0019] alkyl

[0020] In this application, the term "alkyl" refers, whether as part of other terms or used alone, to a saturated hydrocarbon group, which may be straight-chain or branched. The term "C1-C60 alkyl" is derived from a monovalent substituent of a straight-chain or branched saturated hydrocarbon having 1 to 60 carbon atoms, preferably 1 to 40 carbon atoms, and more preferably 1 to 20 carbon atoms. Examples of such substituents include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl.

[0021] alkenyl

[0022] In this application, the term "alkenyl" refers, whether as part of other terms or used alone, to a saturated hydrocarbon group, which may be straight-chain or branched and has at least one carbon-carbon double bond. The term "C2-C60 alkenyl" refers to an alkenyl group having 2 to 60 carbon atoms, preferably 1 to 40 carbon atoms, and even more preferably 1 to 20 carbon atoms. Of course, the alkenyl group includes, but is not limited to, vinyl, n-propenyl, isopropenyl, n-butenyl, sec-butenyl, etc.

[0023] acetylin

[0024] In this application, the term "alkynyl" refers, whether as part of other terms or used alone, to a saturated alkynyl group, which may be straight-chain or branched and has at least one carbon-carbon triple bond. The term "C2-C60 alkynyl" refers to an alkynyl group having 2 to 60 carbon atoms, preferably 2 to 40 carbon atoms, and even more preferably 2 to 20 carbon atoms. Of course, the alkynyl group includes, but is not limited to, acetylene, propyne, etc.

[0025] cycloalkyl

[0026] In this application, the term "cycloalkyl" refers to a cyclic alkyl group consisting of at least 3 atoms. Further, C3-C60 refers to a monocyclic or polycyclic hydrocarbon derived from a main chain of 3 to 60 carbon atoms, preferably 3 to 40 carbon atoms, and even more preferably 3 to 20 carbon atoms. Of course, the cycloalkyl group includes, but is not limited to, cyclopropyl, cyclobutyl, adamantyl, etc.

[0027] Heterocyclic alkyl

[0028] In this application, the term "heterocyclic alkyl" includes one or more of O, S, Se, N, and Si as heteroatoms, and C1-C60 heterocyclic alkyl refers to a monocyclic or polycyclic ring having 1 to 60 carbon atoms, preferably 1 to 40 carbon atoms, and even more preferably 1 to 20 carbon atoms. Here, the polycyclic refers to a group in which a heterocyclic alkyl group is directly attached to or fused with another cyclic group. Here, the other cyclic group can also be a heterocyclic alkyl group, but it can also be another type of cyclic group, such as cycloalkyl, aryl, heteroaryl, etc.

[0029] Cycloalkenyl

[0030] In this application, the term "cycloalkenyl" refers to a cyclic alkenyl group consisting of at least 3 atoms. Further, C3-C60 cycloalkenyl refers to a monocyclic or polycyclic hydrocarbon derived from a main chain of 3 to 60 carbon atoms, preferably 3 to 40 carbon atoms, and even more preferably 3 to 20 carbon atoms.

[0031] Heterocyclic alkenyl

[0032] In this application, the term "heterocyclic alkenyl" includes one or more of O, S, Se, N and Si as heteroatoms, and C1-C60 heterocyclic alkenyl has a monocyclic or polycyclic structure with 1 to 60 carbon atoms, preferably 1 to 40 carbon atoms, and even more preferably 1 to 20 carbon atoms, here.

[0033] Aryl, aryl

[0034] In this application, the terms "aryl" and "arylene" include monocyclic, polycyclic, or fused-ring aryl groups, wherein the rings may be interrupted by short non-aromatic units and may contain a spirostructure. Aryl groups include, but are not limited to, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracene, fluorene, and spirodifluorene. Arylene groups include, but are not limited to, phenylene, biphenylene, terphenylene, naphthylene, phenanthrylene, anthracene, fluorene, and spirodifluorene. Arylene refers to a divalent or polyvalent group formed by the further loss of one or more hydrogen atoms from an aryl group.

[0035] Triphenyl

[0036] In this application, terphenyl includes

[0037] fluorescein

[0038] In this application, the fluorene group can be substituted by one or more substituents. When the fluorene group is substituted, the substituted fluorene group can be: And so on, but not limited to these.

[0039] heteroaryl

[0040] In this application, the term "heteroaryl" includes monocyclic, polycyclic, or fused-ring heteroaryl groups, wherein the rings may be interrupted by short non-aromatic units, and the heteroatoms include nitrogen, oxygen, and sulfur. Heteroaryl groups include, but are not limited to, furanyl, phenylthio, pyrroleyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetraazinyl, triazolyl, tetraazolyl, furazolidyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiopheneyl, isobenzofuranyl, dibenzofuranyl, dibenzothiopheneyl, benzimidazolyl, and benzyl. Benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazoleyl, benzothiadiazolyl, quinolinyl, isoquinolinyl, cenolinyl, quinazolinyl, quinoxalinyl, carbazoleyl, phenoxazinyl, phenthiazinyl, phenanthidyl, benzo[m]dioxacyclopentenyl, dihydroacridyl, and their derivatives; heteroaryl groups include, but are not limited to, furanyl, phenylthio, and pyrroleyl. Imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzimidazolyl Azolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, ininazole, benzothiadiazolyl, quinolinyl, isoquinolinyl, cenolinyl, quinazolinyl, quinoxolinyl, carbazolyl, phenoxazinyl, phenthiazinyl, phenanthridyl, phenanthridyl, benzo[m]dioxacyclopentenyl, dihydroacridyl, and their derivatives, etc. As used herein, the term "substituted" means that a hydrogen atom in the compound is replaced by another substituent. This position is not limited to a specific position, as long as the hydrogen at that position can be replaced by a substituent. When two or more substituents are present, the two or more substituents can be the same or different.

[0041] halogen

[0042] In this application, the term "halogen" refers to an atom selected from fluorine, chlorine, bromine, and iodine.

[0043] hydrogen

[0044] In this application, unless otherwise stated, hydrogen atoms include protium, deuterium, and tritium.

[0045] C1-C60, C3-C60, C6-C60

[0046] In this application, the limits of C1-C60, C3-C60, and C6-C60 define the range of carbon atoms, and the number of carbon atoms is any integer within the defined range. For example, C6-C60 aryl means that the number of carbon atoms representing the aryl group can be any integer within the range of 6-60, such as 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, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, and 60.

[0047] Preferably, the organic electroluminescent compound comprises at least one of the following structures:

[0048]

[0049]

[0050]

[0051]

[0052] In equations (1-1) to (1-25), X1 and X2 are selected from O, S or NR2, and X3 is selected from O or S.

[0053] Preferably, L1, L2, and L3 are each independently selected from single-bonded or substituted or unsubstituted C6-C50 arylene groups, wherein substituted or unsubstituted C6-C50 arylene groups represent substituted or unsubstituted arylene groups with 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, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, or 50 carbon atoms.

[0054] The substituents in the substituted C6-C50 arylene groups are each independently selected from one or more of the following: deuterium, halogen, cyano, hydroxyl, nitro, amido, hydrazine, C1-C50 alkyl, C2-C50 alkenyl, C3-C50 cycloalkyl, C2-C50 alkynyl, C3-C50 cycloalkyl, C1-C50 heterocycloalkyl, C3-C50 cycloalkenyl, C1-C50 heterocycloalkenyl, C6-C50 aryl, and C1-C50 heteroaryl.

[0055] Preferably, L1, L2 and L3 are each independently selected from single-bonded or substituted or unsubstituted C6-C30 aryl groups.

[0056] The substituents in the substituted C6-C30 arylene groups are each independently selected from one or more of the following: deuterium, halogen, cyano, hydroxyl, nitro, amido, hydrazine, C1-C30 alkyl, C2-C30 alkenyl, C3-C30 cycloalkyl, C2-C30 alkynyl, C3-C30 cycloalkyl, C1-C30 heterocyclic alkyl, C3-C30 cycloalkenyl, C1-C30 heterocyclic alkenyl, C6-C30 aryl, and C1-C30 heteroaryl.

[0057] Preferably, L1, L2 and L3 are each independently selected from single-bonded or substituted or unsubstituted C6-C25 arylene groups;

[0058] Preferably, the substituents in the substituted C6-C25 arylene groups are each independently selected from one or more of the following: deuterium, halogen, cyano, hydroxyl, nitro, amidine, hydrazine, C1-C25 alkyl, C2-C25 alkenyl, C3-C25 cycloalkyl, C2-C25 alkynyl, C3-C25 cycloalkyl, C1-C25 heterocyclic alkyl, C3-C25 cycloalkenyl, C1-C25 heterocyclic alkenyl, C6-C25 aryl, and C1-C25 heteroaryl.

[0059] Preferably, L1, L2, and L3 are each independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted triphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted anthraceneylene, substituted or unsubstituted phenanthylene, substituted or unsubstituted perylene, substituted or unsubstituted fluoranthylene, substituted or unsubstituted triphenylenylene, and substituted or unsubstituted phenanthroline. enyl), substituted or unsubstituted pyrene, substituted or unsubstituted tetraphenyl, substituted or unsubstituted pentaphenyl, substituted or unsubstituted fluorene, substituted or unsubstituted indene, substituted or unsubstituted acenaphthene, substituted or unsubstituted fluorene, substituted or unsubstituted benzofluorene, substituted or unsubstituted spirobisfluorene, substituted or unsubstituted pyridyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl.

[0060] Among them, substituted phenylene, substituted biphenylene, substituted triphenylene, substituted naphthylene, substituted anthraceneylene, substituted phenanthylene, substituted perylene, substituted fluoranthylene, substituted triphenylenylene, substituted phenalenylene, substituted pyrene, substituted tetraphenylene, substituted pentaphenylene, substituted fluorene, substituted indene, substituted The substituents in acenaphthene, substituted fluorene, substituted benzo[a]fluorene, substituted spirobisfluorene, substituted pyridinyl, substituted dibenzothiophene, substituted dibenzofuran, and substituted carbazolyl are each independently selected from one or more of deuterium, halogen, cyano, hydroxyl, nitro, amido, hydrazyl, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl, phenyl, biphenyl, naphthyl, binatyl, and bitriphenyl.

[0061] Preferably, L1, L2, and L3 are selected from the group consisting of single bonds or the following groups:

[0062]

[0063]

[0064] Understandably, D stands for deuterium. For specific functional groups, such as... This indicates that the substituted positions in the phenylene group are replaced by four deuterium groups, meaning the phenylene group is fully deuterated. Other deuterated groups are also fully deuterated. The explanations for (D) groups below are similar.

[0065] Preferably, Ar1 and Ar2 are each independently selected from substituted or unsubstituted C6-C50 aryl groups or substituted or unsubstituted C1-C50 heteroaryl groups;

[0066] The substituents in the substituted C6-C50 aryl and substituted C1-C50 heteroaryl are selected from one or more of the following: deuterium, halogen, cyano, hydroxyl, nitro, amido, hydrazine, C1-C50 alkyl, C2-C50 alkenyl, C3-C50 cycloalkyl, C2-C50 alkynyl, C3-C50 cycloalkyl, C1-C50 heterocycloalkyl, C3-C50 cycloalkenyl, C1-C50 heterocycloalkenyl, C6-C50 aryl, and C1-C50 heteroaryl.

[0067] Preferably, Ar1 and Ar2 are each independently selected from substituted or unsubstituted C6-C30 aryl groups or substituted or unsubstituted C1-C30 heteroaryl groups.

[0068] The substituents in the substituted C6-C30 aryl and substituted C1-C30 heteroaryl are selected from one or more of the following: deuterium, halogen, cyano, hydroxyl, nitro, amido, hydrazine, C1-C30 alkyl, C2-C30 alkenyl, C3-C30 cycloalkyl, C2-C30 alkynyl, C3-C30 cycloalkyl, C1-C30 heterocycloalkyl, C3-C30 cycloalkenyl, C1-C30 heterocycloalkenyl, C6-C30 aryl, and C1-C30 heteroaryl.

[0069] Preferably, Ar1 and Ar2 are each independently selected from substituted or unsubstituted C6-C25 aryl or substituted or unsubstituted C1-C25 heteroaryl;

[0070] The substituents in the substituted C6-C25 aryl and substituted C1-C25 heteroaryl are selected from one or more of the following: deuterium, halogen, cyano, hydroxyl, nitro, amido, hydrazine, C1-C25 alkyl, C2-C25 alkenyl, C3-C25 cycloalkyl, C2-C25 alkynyl, C3-C25 cycloalkyl, C1-C25 heterocycloalkyl, C3-C25 cycloalkenyl, C1-C25 heterocycloalkenyl, C6-C25 aryl, and C1-C25 heteroaryl.

[0071] Preferably, Ar1 and Ar2 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted binaphthyl, substituted or unsubstituted phenylnaphthyl, substituted or unsubstituted naphthylphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenylfluorenyl, substituted or unsubstituted benzo[a]fluorenyl, substituted or unsubstituted dibenzo[a]fluorenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted phenylphenanthyl, substituted or unsubstituted anthrayl, substituted or unsubstituted indene, substituted or unsubstituted tetraphenyl, substituted or unsubstituted perylene. Substituted or unsubstituted trefoilyl, substituted or unsubstituted tetraphenyl, substituted or unsubstituted fluoranyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted furanyl, substituted or unsubstituted phenylthio, substituted or unsubstituted pyrroleyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted pyrazolyl, substituted or unsubstituted thiazolyl, substituted or unsubstituted thiadiazolyl, substituted or unsubstituted isothiazolyl, substituted or unsubstituted isoxazolyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted oxadiazolyl, substituted or unsubstituted triazine, substituted or unsubstituted tetraazine, substituted or unsubstituted triazolyl, etc. Substituted or unsubstituted tetrazolyl, substituted or unsubstituted furazolidyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiopheneyl, substituted or unsubstituted isobenzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted benzoisothiazolyl, substituted or unsubstituted benzoisoxazoleyl, substituted or unsubstituted benzoxazoleyl, substituted or unsubstituted The following are substituted isoindolyl, substituted or unsubstituted indolyl, substituted or unsubstituted indazole, substituted or unsubstituted benzothiadiazolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted cyclolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted phenthiazinyl, substituted or unsubstituted phenanthinyl, substituted or unsubstituted dipyridyl, substituted or unsubstituted tripyridyl, substituted or unsubstituted phenyl tripyridyl, or substituted or unsubstituted diazafluorenyl or phenanthrolinel;

[0072] Among them, substituted phenyl, substituted biphenyl, substituted triphenyl, substituted naphthyl, substituted binaphthyl, substituted phenylnaphthyl, substituted naphthylphenyl, substituted fluorenyl, substituted phenylfluorenyl, substituted benzo[a]fluorenyl, substituted dibenzo[a]fluorenyl, substituted phenanthryl, substituted phenylphenanthryl, substituted anthraceneyl, substituted indyl, substituted tetraphenyl, substituted perylene, substituted tyl, substituted tetraphenyl, substituted fluoranyl, substituted spirodifluorenyl, substituted furanyl Substituted phenylthio, substituted pyrrole, substituted imidazolyl, substituted pyrazolyl, substituted thiazolyl, substituted thiadiazolyl, substituted isothiazolyl, substituted isoxazolyl, substituted oxazolyl, substituted oxadiazolyl, substituted triazinyl, substituted tetraazinyl, substituted triazolyl, substituted tetraazolyl, substituted furazolidone, substituted pyridinyl, substituted pyrazinyl, substituted pyrimidinyl, substituted pyridazinyl, substituted benzofuranyl, substituted benzothiopheneyl, substituted iso Benzofuranyl, substituted dibenzofuranyl, substituted dibenzothiophenyl, substituted benzimidazolyl, substituted benzothiazolyl, substituted benzoisothiazolyl, substituted benzoisooxazolyl, substituted benzooxazolyl, substituted isoindolyl, substituted indolyl, substituted indazole, substituted benzothiadiazolyl, substituted quinolinyl, substituted isoquinolinyl, substituted terpineyl, substituted quinazolinyl, substituted quinoxalinyl, substituted carbazole, substituted phenoxazinyl, substituted The substituents in phenanthiazinyl, substituted phenanthridine, substituted dipyridyl, substituted terpyridyl, substituted phenyl terpyridyl, or substituted diazafluorenyl or phenanthroline are selected from one or more of deuterium, halogen, cyano, hydroxy, nitro, amido, hydrazyl, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl, phenyl, naphthyl, biphenyl, naphthyl, bitriphenyl, fluorenyl, dibenzofuranyl, dibenzothiopheneyl, or carbazoyl.

[0073] Preferably, Ar1 and Ar2 are each independently selected from the group consisting of:

[0074]

[0075]

[0076]

[0077]

[0078]

[0079] Preferably, R1 and R2 are each independently selected from hydrogen, deuterium, halogen, hydroxyl, nitro, amidine, hydrazine, substituted or unsubstituted C1-C50 alkyl, substituted or unsubstituted C2-C50 alkenyl, substituted or unsubstituted C2-C50 alkynyl, substituted or unsubstituted C3-C50 cycloalkyl, substituted or unsubstituted C1-C50 heterocycloalkyl, substituted or unsubstituted C3-C50 cycloalkenyl, substituted or unsubstituted C1-C50 heterocycloalkenyl, substituted or unsubstituted C6-C50 aryl, substituted or unsubstituted C1-C50 heteroaryl;

[0080] The substituents in the substituted C1-C50 alkyl, substituted C2-C50 alkenyl, substituted C2-C50 alkynyl, substituted C3-C50 cycloalkyl, substituted C1-C50 heterocyclic alkyl, substituted C3-C50 cycloalkenyl, substituted C1-C50 heterocyclic alkenyl, substituted C6-C50 aryl, and substituted C1-C50 heteroaryl are selected from one or more of the following: deuterium, halogen, cyano, hydroxyl, nitro, amidine, hydrazine, C1-C50 alkyl, C2-C50 alkenyl, C3-C50 cycloalkyl, C2-C50 alkynyl, C3-C50 cycloalkyl, C1-C50 heterocyclic alkyl, C3-C50 cycloalkenyl, C1-C50 heterocyclic alkenyl, C6-C50 aryl, and C1-C50 heteroaryl.

[0081] Preferably, R1 and R2 are each selected from hydrogen, deuterium, halogen, hydroxyl, nitro, amido, hydrazine, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C2-C30 alkynyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C1-C30 heterocycloalkyl, substituted or unsubstituted C3-C30 cycloalkenyl, substituted or unsubstituted C1-C30 heterocycloalkenyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C1-C30 heteroaryl.

[0082] The substituents in the substituted C1-C30 alkyl, substituted C2-C30 alkenyl, substituted C2-C30 alkynyl, substituted C3-C30 cycloalkyl, substituted C1-C30 heterocyclic alkyl, substituted C3-C30 cycloalkenyl, substituted C1-C30 heterocyclic alkenyl, substituted C6-C30 aryl, and substituted C1-C30 heteroaryl are selected from one or more of deuterium, halogen, cyano, hydroxyl, nitro, amido, hydrazine, C1-C30 alkyl, C2-C30 alkenyl, C3-C30 cycloalkyl, C2-C30 alkynyl, C3-C30 cycloalkyl, C1-C30 heterocyclic alkyl, C3-C30 cycloalkenyl, C1-C30 heterocyclic alkenyl, C6-C30 aryl, and C1-C30 heteroaryl.

[0083] Preferably, R1 and R2 are each independently selected from hydrogen, deuterium, halogen, hydroxyl, nitro, amidine, hydrazine, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C2-C25 alkenyl, substituted or unsubstituted C2-C25 alkynyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C3-C25 cycloalkenyl, substituted or unsubstituted C1-C25 heterocycloalkenyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C1-C25 heteroaryl;

[0084] The substituents in the substituted C1-C25 alkyl, substituted C2-C25 alkenyl, substituted C2-C25 alkynyl, substituted C3-C25 cycloalkyl, substituted C1-C25 heterocyclic alkyl, substituted C3-C25 cycloalkenyl, substituted C1-C25 heterocyclic alkenyl, substituted C6-C25 aryl, and substituted C1-C25 heteroaryl are selected from one or more of the following: deuterium, halogen, cyano, hydroxyl, nitro, amido, hydrazine, C1-C25 alkyl, C2-C25 alkenyl, C3-C25 cycloalkyl, C2-C25 alkynyl, C3-C25 cycloalkyl, C1-C25 heterocyclic alkyl, C3-C25 cycloalkenyl, C1-C25 heterocyclic alkenyl, C6-C25 aryl, and C1-C25 heteroaryl.

[0085] Preferably, R1 and R2 are each independently selected from deuterium, halogen, cyano, hydroxyl, nitro, amidine, hydrazine, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted binaphthyl, substituted or unsubstituted phenylnaphthyl, substituted or unsubstituted naphthylphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenylfluorenyl, substituted or unsubstituted benzo[a]fluorenyl, substituted or unsubstituted dibenzo[a]fluorenyl, substituted or unsubstituted phenanthrene, substituted or unsubstituted phenylphenanthrene, substituted or unsubstituted anthracene, substituted or unsubstituted indene, substituted or unsubstituted Tetraphenyl, substituted or unsubstituted perylyl, substituted or unsubstituted trefyl, substituted or unsubstituted tetraphenyl, substituted or unsubstituted fluoranyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted furanyl, substituted or unsubstituted phenylthio, substituted or unsubstituted pyrroleyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted pyrazolyl, substituted or unsubstituted thiazolyl, substituted or unsubstituted thiadiazolyl, substituted or unsubstituted isothiazolyl, substituted or unsubstituted isoxazolyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted oxadiazolyl, substituted or unsubstituted triazinyl, substituted or unsubstituted tetraazinyl, substituted or Unsubstituted triazolyl, substituted or unsubstituted tetrazolyl, substituted or unsubstituted furazolidone, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiopheneyl, substituted or unsubstituted isobenzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted benzoisothiazolyl, substituted or unsubstituted benzoisooxazolyl, substituted or unsubstituted benzooxazolyl, etc. Substituted or unsubstituted isoindolyl, substituted or unsubstituted indolyl, substituted or unsubstituted indazole, substituted or unsubstituted benzothiadiazolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted cyclolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted phenthiazinyl, substituted or unsubstituted phenanthinyl, substituted or unsubstituted dipyridyl, substituted or unsubstituted tripyridyl, substituted or unsubstituted phenyl tripyridyl, or substituted or unsubstituted diazafluorenyl or phenanthrolinel;

[0086] Among them, substituted phenyl, substituted biphenyl, substituted triphenyl, substituted naphthyl, substituted binaphthyl, substituted phenylnaphthyl, substituted naphthylphenyl, substituted fluorenyl, substituted phenylfluorenyl, substituted benzo[a]fluorenyl, substituted dibenzo[a]fluorenyl, substituted phenanthryl, substituted phenylphenanthryl, substituted anthraceneyl, substituted indyl, substituted tetraphenyl, substituted perylene, substituted tyl, substituted tetraphenyl, substituted fluoranyl, substituted spirodifluorenyl, substituted furanyl Substituted phenylthio, substituted pyrrole, substituted imidazolyl, substituted pyrazolyl, substituted thiazolyl, substituted thiadiazolyl, substituted isothiazolyl, substituted isoxazolyl, substituted oxazolyl, substituted oxadiazolyl, substituted triazinyl, substituted tetraazinyl, substituted triazolyl, substituted tetraazolyl, substituted furazolidone, substituted pyridinyl, substituted pyrazinyl, substituted pyrimidinyl, substituted pyridazinyl, substituted benzofuranyl, substituted benzothiopheneyl, substituted iso Benzofuranyl, substituted dibenzofuranyl, substituted dibenzothiophenyl, substituted benzimidazolyl, substituted benzothiazolyl, substituted benzoisothiazolyl, substituted benzoisooxazolyl, substituted benzooxazolyl, substituted isoindolyl, substituted indolyl, substituted indazole, substituted benzothiadiazolyl, substituted quinolinyl, substituted isoquinolinyl, substituted terpineyl, substituted quinazolinyl, substituted quinoxalinyl, substituted carbazole, substituted phenoxazinyl, substituted The substituents in phenanthiazinyl, substituted phenanthridine, substituted dipyridyl, substituted terpyridyl, substituted phenyl terpyridyl, or substituted diazafluorenyl or phenanthroline are selected from one or more of deuterium, halogen, cyano, hydroxy, nitro, amido, hydrazyl, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl, phenyl, naphthyl, biphenyl, naphthyl, bitriphenyl, fluorenyl, dibenzofuranyl, dibenzothiopheneyl, or carbazoyl.

[0087] Preferably, R1 and R2 are each independently selected from the group consisting of hydrogen, deuterium, or the following groups:

[0088]

[0089] Preferably, ring A is selected from substituted or unsubstituted C6-C50 aromatic rings or substituted or unsubstituted C3-C50 heteroaromatic rings;

[0090] The substituents in the substituted C6-C50 aromatic ring and the substituted C3-C50 heteroaromatic ring are selected from one or more of the following: deuterium, halogen, cyano, hydroxyl, nitro, amido, hydrazine, C1-C60 alkyl, C2-C60 alkenyl, C3-C60 cycloalkyl, C2-C60 alkynyl, C3-C60 cycloalkyl, C1-C60 heterocycloalkyl, C3-C60 cycloalkenyl, C1-C60 heterocycloalkenyl, C6-C60 aryl, and C1-C60 heteroaryl.

[0091] Preferably, ring A is selected from substituted or unsubstituted C6-C25 aromatic rings or substituted or unsubstituted C3-C25 heteroaromatic rings;

[0092] The substituents in the substituted C6-C25 aromatic ring and the substituted C3-C25 heteroaromatic ring are selected from one or more of the following: deuterium, halogen, cyano, hydroxyl, nitro, amido, hydrazine, C1-C60 alkyl, C2-C60 alkenyl, C3-C60 cycloalkyl, C2-C60 alkynyl, C3-C60 cycloalkyl, C1-C60 heterocycloalkyl, C3-C60 cycloalkenyl, C1-C60 heterocycloalkenyl, C6-C60 aryl, and C1-C60 heteroaryl.

[0093] Preferably, ring A is selected from substituted or unsubstituted benzene, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthalene, substituted or unsubstituted binaphthalene, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzofluorene, substituted or unsubstituted phenanthrene, substituted or unsubstituted furan, substituted or unsubstituted benzenesulfonium, substituted or unsubstituted pyrrole, substituted or unsubstituted imidazole, substituted or unsubstituted benzofuran, substituted or unsubstituted benzothiophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene;

[0094] The substituents in the substituted ring are selected from one or more of the following: deuterium, halogen, cyano, hydroxyl, nitro, amido, hydrazine, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl, phenyl, naphthyl, biphenyl, binatyl, bitriphenyl, fluorenyl, dibenzofuranyl, dibenzothiophene, or carbazole.

[0095] Preferably, ring A is selected from benzene ring or naphthalene ring.

[0096] Preferably, n is selected from 0 or 3.

[0097] Preferably, the organic electroluminescent compound is selected from one of the following structures:

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113] This invention also provides a method for synthesizing the above-mentioned organic electroluminescent compound having the structure of formula (1), the specific synthetic route of which is shown below:

[0114] (1) Synthesis of the intermediate sub-gn:

[0115] 1) When ring A of intermediate sub-gn is linked to a triarylamine, the general synthetic formula is as follows:

[0116]

[0117] 2) When another part of the intermediate sub-gn is linked to a triarylamine, the general synthetic formula is as follows:

[0118]

[0119] (2) Synthesis of the intermediate sub-hn:

[0120]

[0121] (3) The synthetic route of the organic electroluminescent compound is shown below:

[0122]

[0123] Or for

[0124]

[0125] The present invention also provides an organic electroluminescent material comprising the organic electroluminescent compound as described above.

[0126] The present invention also provides an organic electroluminescent device, the organic electroluminescent device comprising a first electrode, a second electrode disposed opposite to the first electrode, and at least one organic layer between the first electrode and the second electrode, the organic layer comprising an organic electroluminescent compound or an organic electroluminescent material as described above.

[0127] Preferably, the organic electroluminescent device includes a first electrode, a second electrode disposed opposite to the first electrode, and at least one organic layer between the first electrode and the second electrode, wherein the organic layer comprises the aforementioned organic electroluminescent compound or the aforementioned organic electroluminescent material.

[0128] Preferably, the organic layer can be composed of a single-layer structure or a multi-layer structure with two or more layers stacked on top of each other. For example, the organic electroluminescent device may include one or more of the following sequentially arranged layers: a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer. It should be noted that if an electron blocking layer and a hole blocking layer are present, the nitrogen-containing compound or the organic electroluminescent material is located between the electron blocking layer and the hole blocking layer, i.e., it belongs to the light-emitting layer material.

[0129] Preferably, the organic electroluminescent device of this application can be, for example, an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a cathode that are sequentially stacked on a substrate.

[0130] Preferably, the anode comprises an anode material, preferably a material with a large work function that facilitates hole injection into the first hole transport layer. For example, the anode material may include: metals such as nickel, platinum, 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; or conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, and polyaniline, but is not limited thereto.

[0131] Preferably, the hole injection layer is used to enhance the ability to inject holes into the hole transport layer. The hole injection layer can be selected from benzidine derivatives, starburst-like aryl amine compounds, phthalocyanine derivatives, or other materials; this application does not impose any special limitations on this. The material of the hole injection layer can, for example, be selected from the following compounds or any combination thereof:

[0132]

[0133]

[0134] Preferably, the hole transport layer may include one or more hole transport materials. The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer. The material of the hole transport layer may be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds. This application does not impose any special limitations on this. The material of the hole transport layer may, for example, be selected from the following compounds or any combination thereof:

[0135]

[0136] Preferably, the material of the electron blocking layer is selected from conventional materials used in the art. An electron blocking layer is a layer disposed between the light-emitting auxiliary layer and the light-emitting layer to prevent electrons injected from the cathode from transferring to the light-emitting auxiliary layer and recombinating in the light-emitting layer; it can also be called an electron blocking layer or an electron suppression layer. The electron blocking layer is preferably made of a material with a lower electron affinity than the electron transport layer. This application does not impose any special limitations in this regard.

[0137] Preferably, the light-emitting layer is a material capable of receiving holes and electrons from the hole transport layer and the electron transport layer respectively, and combining them to emit light in the visible light region.

[0138] Preferably, the light-emitting layer can be composed of a single light-emitting material, or it can include a host material and a guest material. For example, the light-emitting layer includes a host material and a guest material. Holes injected into the light-emitting layer and then electrons injected into the light-emitting layer can recombine in the light-emitting layer to form excitons. The excitons transfer energy to the host material, and the host material transfers energy to the guest material, thereby causing the guest material to emit light.

[0139] Preferably, the host material of the light-emitting layer may include metal chelating compounds, bis(phenylacetyl) derivatives, aromatic amine derivatives, dibenzofuran derivatives, and other types of materials. For example, the host material may include the above-mentioned nitrogen-containing compounds or the above-mentioned organic electroluminescent materials.

[0140] Preferably, the guest material of the luminescent layer may comprise a compound having a condensed aryl ring or a derivative thereof, a compound having a heteroaryl ring or a derivative thereof, an aromatic amine derivative, or other types of materials, which are not limited herein by this application. The guest material is also referred to as a dopant or dopant, and can be classified into fluorescent dopant and phosphorescent dopant according to the type of luminescence.

[0141] Preferably, the material of the hole blocking layer is selected from conventional materials in the art. The hole blocking layer is a layer disposed between the electron transport layer and the light-emitting layer to prevent holes injected by the anode from being transferred to the electron transport layer and recombination in the light-emitting layer; it can also be referred to as a hole suppression layer or a hole blocking layer. The hole blocking layer is preferably made of a material with high ionization energy. This application does not impose any special limitations in this regard.

[0142] Preferably, the electron transport layer can be a single-layer structure or a multi-layer structure, and may include one or more electron transport materials. The electron transport layer is a layer that receives electrons from the cathode or an electron injection layer formed on the cathode, transports electrons to the light-emitting layer, and suppresses hole transfer from the light-emitting layer. The electron transport material is suitably one that can effectively receive electron injection from the cathode and transfer electrons to the light-emitting layer, and has a high electron mobility. The electron transport layer may be selected from, but is not limited to, Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, hydroxyflavonoid-metal complexes, etc., but is not limited to these.

[0143] Preferably, the electron transport layer includes, but is not limited to, the following structures:

[0144]

[0145] Preferably, the electron injection layer is used to enhance the ability to inject electrons into the electron transport layer. The electron injection layer may include fluorenone, anthraquinone dimethane, biphenylquinone, thiamethane dioxide, azole, diazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenemethane, anthrone, and their derivatives; inorganic materials such as alkali metal sulfides and alkali metal halides; or may include complexes of alkali metals and organic compounds.

[0146] Preferably, the cathode is a material with a small work function that facilitates electron injection into the functional layers. 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; or multilayer materials such as LiF / Al, Liq / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca.

[0147] The present invention also provides an application of the organic electroluminescent device as described above in optical fiber equipment, lighting equipment, electrophotographic photosensitive equipment, photoelectric converters, organic solar cells, switching element equipment, organic light-emitting field-effect transistors, image sensors, or dye lasers.

[0148] The beneficial effects of this invention are:

[0149] The organic electroluminescent compound provided by the present invention is based on the core in the structure of formula (1). By combining different substituents, the HOMO and LUMO energy levels of the organic electroluminescent compound can have a high degree of matching with the adjacent energy levels, so that the carrier mobility of the organic electroluminescent compound is more balanced, thereby enabling the organic electroluminescent device containing the organic electroluminescent compound to have a lower driving voltage, higher luminous efficiency and longer lifetime. Attached Figure Description

[0150] To more clearly illustrate the specific embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the specific embodiments or the prior art will be briefly introduced below. Obviously, the drawings described below are some embodiments of the present invention. For those skilled in the art, other drawings can be obtained from these drawings without creative effort.

[0151] Figure 1 This is a structural diagram of the organic electroluminescent device in the device embodiment of the present invention;

[0152] 1-Substrate; 2-Anode; 3-Hole injection layer; 4-Hole transport layer; 5-Light emission layer; 6-Electron transport layer; 7-Electron injection layer; 8-Cathode. Detailed Implementation

[0153] For experiments not specifically described in the examples, the procedures or conditions should be followed according to the conventional experimental procedures described in the literature in this field. Reagents or instruments whose manufacturers are not specified are all commercially available conventional reagent products.

[0154] Those skilled in the art will recognize that the chemical reactions described herein can be suitably used to prepare many of the heterocyclic compounds of this application, and other methods for preparing the compounds of this application are considered to be within the scope of this application. For example, the synthesis of those non-illustrative compounds according to this application can be successfully accomplished by those skilled in the art through modification methods, such as appropriately protecting interfering groups, utilizing other known reagents besides those described herein, or making some conventional modifications to the reaction conditions. Compounds for which synthetic methods are not mentioned in this application are commercially available starting materials.

[0155] Synthesis of intermediate sub-g1:

[0156]

[0157] 100 g sub-a1 (370 mmol), 84.4 g sub-b1 (555 mmol), 8.6 g Pd(PPh3)4 (7.4 mmol), 102 g K2CO3 (741 mmol), 800 mL tetrahydrofuran, and 200 mL water were added. The mixture was heated under nitrogen protection to an internal temperature of 50 ± 2 °C for 8 h. After the reaction, the product was extracted with ethyl acetate and water. The resulting organic layer was dried over magnesium sulfate (MgSO4) and concentrated. The resulting compound was then subjected to silica gel column chromatography and recrystallized to give 70 g of product sub-c1, in 63% yield.

[0158] 50 g of sub-c1 (168 mmol), 37.4 g of sub-d1 (201 mmol), 3.9 g of Pd(PPh3)4 (3.4 mmol), 46.3 g of K2CO3 (335 mmol), 400 mL of 1,4-dioxane, and 100 mL of water were heated to an internal temperature of 90 ± 2 °C and reacted for 5 h. After the reaction was complete, the mixture was extracted with ethyl acetate and water, and the resulting organic layer was dried over magnesium sulfate (MgSO4) and concentrated. The resulting compound was then subjected to silica gel column chromatography and recrystallized to give 42 g of product sub-e1, in 70% yield.

[0159] 40 g of sub-e1 (111 mmol) and 400 mL of dichloromethane were added to a 1000 mL three-necked flask. The mixture was stirred at -10 °C for 20 min, and then 200 mL of BBr3 (2 mol / L, 400 mmol) was slowly added dropwise while maintaining the internal temperature at -10–0 °C. After the addition was complete, stirring was continued for 30 min. After the reaction was complete, the reaction solution was poured into ice water and extracted with dichloromethane and water. The resulting organic layer was dried over magnesium sulfate (MgSO4) and concentrated. The resulting compound was then crystallized with n-hexane to give 29 g of product sub-f1, with a yield of 79%.

[0160] In a three-necked flask, 29 g of sub-f1 (87 mmol), 57 g of cesium carbonate (175 mmol), and 300 mL of NMP were added. The mixture was heated to 140 °C and reacted for 6 h. After the reaction was complete, the mixture was quenched with water, sodium chloride was added, and the mixture was extracted with ethyl acetate and water. The resulting organic layer was dried over magnesium sulfate (MgSO4) and concentrated to give 19 g of the product sub-g1, with a yield of 75%.

[0161] Synthesis of intermediate sub-g2:

[0162]

[0163] The synthesis method of intermediate sub-g2 is the same as that of intermediate sub-g1, except that the raw material sub-a1 is replaced with sub-a2 (1,3-dibromo-2,4-difluorobenzene), and the rest of the operations are consistent with the above synthesis method.

[0164] Synthesis of intermediate sub-g3:

[0165]

[0166] The synthesis method of intermediate sub-g3 is the same as that of intermediate sub-g1, except that the raw material sub-a1 is replaced with sub-a3 (2,3-dibromo-1,4-difluorobenzene), and the rest of the operations are consistent with the above synthesis method.

[0167] Synthesis of intermediate sub-g4:

[0168]

[0169] The synthesis method of intermediate sub-g4 is the same as that of intermediate sub-g1, except that the raw material sub-a1 is replaced with sub-a4 (1,5-dibromo-2,4-difluorobenzene) and sub-d1 is replaced with sub-d4 (5-chloro-2-methoxyphenylboronic acid). All other operations are the same as the synthesis method described above.

[0170] Synthesis of intermediate sub-g5:

[0171]

[0172] The synthesis method of intermediate sub-g5 is the same as that of intermediate sub-g1, except that the raw material sub-a1 is replaced with sub-a5 (1,4-dibromo-2,3-difluorobenzene), and the rest of the operations are consistent with the above synthesis method.

[0173] Synthesis of intermediate sub-g6:

[0174]

[0175] The synthesis method of intermediate sub-g6 is the same as that of intermediate sub-g1, except that the raw material sub-d1 is replaced with sub-d6, and the rest of the operations are the same as the above synthesis method.

[0176] The specific synthesis process of sub-d6 is as follows:

[0177]

[0178] 10 g of 1-chloro-3-methoxynaphthalene (51.9 mmol) and 11.1 g of NBS (62.2 mmol) were dissolved in 100 mL of dichloroethane under nitrogen protection and heated to an internal temperature of 70 ± 2 °C for 6 h. After the reaction was complete, the mixture was extracted with dichloromethane and water, and the resulting organic layer was dried over magnesium sulfate (MgSO4) and concentrated. The resulting compound was then subjected to silica gel column chromatography and recrystallized to give 10.6 g of product sub-d6-1, in 75% yield.

[0179] 10 g of sub-d6-1 (38.9 mmol) was dissolved in 100 mL of tetrahydrofuran solvent under nitrogen protection. The mixture was cooled to an internal temperature of -78 ± 2 °C and maintained for 30 min. Then, 2.5 mol / L (42 mmol) of n-butyllithium was slowly added dropwise until the reaction was complete. Next, 50 mmol of trimethyl borate was slowly added dropwise. After the addition was complete, the mixture was stirred at room temperature for 30 min until the reaction was complete. The solution was acidified with concentrated hydrochloric acid, extracted with dichloromethane and water, and the resulting organic layer was dried over magnesium sulfate (MgSO4) and concentrated. The solid was collected by filtration to give 7.6 g of the product sub-d6, with a yield of 87%.

[0180] Synthesis of intermediate sub-g7:

[0181]

[0182] The synthesis method of intermediate sub-g7 is the same as that of intermediate sub-g1, except that the raw material sub-b1 is replaced with sub-b7 (1-methoxy-2-naphthoic acid), and the rest of the operations are consistent with the above synthesis method.

[0183] Synthesis of intermediate sub-g8:

[0184]

[0185] The synthesis method of intermediate sub-g8 is the same as that of intermediate sub-g1, except that the raw material sub-d1 is replaced with sub-d8, and the rest of the operations are the same as the above synthesis method.

[0186] The specific synthesis process of sub-d8 is as follows:

[0187]

[0188] 10 g of 2-bromo-1-methoxynaphthalene (42.2 mmol) and 8.4 g of NCS (63.2 mmol) were dissolved in 100 mL of DMF. The mixture was heated under nitrogen protection to an internal temperature of 90 ± 2 °C for 6 h. After the reaction, the mixture was extracted with dichloromethane and water. The resulting organic layer was dried over magnesium sulfate (MgSO4) and concentrated. The resulting compound was then subjected to silica gel column chromatography and recrystallized to give 9.4 g of the product sub-d8-1, in 82% yield.

[0189] 10 g of sub-d8-1 (38.9 mmol) was dissolved in 100 mL of tetrahydrofuran solvent under nitrogen protection. The mixture was cooled to an internal temperature of -78 ± 2 °C and maintained for 30 min. Then, 2.5 mol / L (42 mmol) of n-butyllithium was slowly added dropwise until the reaction was complete. Next, 50 mmol of trimethyl borate was slowly added dropwise. After the addition was complete, the mixture was stirred at room temperature for 30 min until the reaction was complete. The mixture was then acidified with concentrated hydrochloric acid and extracted with dichloromethane and water. The resulting organic layer was dried over magnesium sulfate (MgSO4) and concentrated. The solid was collected by filtration to give 7.6 g of the product sub-d8, with a yield of 87%.

[0190] Synthesis of intermediate sub-g9:

[0191]

[0192] The synthesis method of intermediate sub-g9 is the same as that of intermediate sub-g1, except that the raw material sub-b1 is replaced with sub-b9 (1-methoxy-2-naphthoboronic acid) and sub-d1 is replaced with sub-d9 (5-chloro-2-methoxyphenylboronic acid). All other operations are the same as the synthesis method described above.

[0193] Synthesis of intermediate sub-g10:

[0194]

[0195] The synthesis method of intermediate sub-g10 is the same as that of intermediate sub-g1, except that the raw material sub-b1 is replaced with sub-b10 (2-methoxy-1-naphthoboronic acid) and sub-d1 is replaced with sub-d10 (5-chloro-2-methoxyphenylboronic acid). All other operations are the same as the above synthesis method.

[0196] Synthesis of intermediate sub-g11:

[0197]

[0198] The synthesis method of intermediate sub-g11 is the same as that of intermediate sub-g1, except that the raw material sub-d1 is replaced with sub-d11 (5-chloro-2-methoxyphenylboronic acid), and the rest of the operation is the same as the above synthesis method.

[0199] Synthesis Example 1

[0200] This synthetic example provides a nitrogen-containing compound S-33, the synthetic steps of which are shown below:

[0201]

[0202] 100 g of 2-amino-3-bromophenol (0.53 mol), 90 g of benzoyl chloride (0.64 mol), and 1 L of ultra-dry 1,4-dioxane were added to a flask under nitrogen protection. The system was placed in a -10°C cryogenic bath, and 90 g of trifluoromethanesulfonic acid was added dropwise to the system at -5 to -10°C over 0.5 to 1 hour. After the addition was complete, the mixture was heated and stirred at 100°C for 2 to 3 hours. The reaction was quenched with water, and the organic phase was extracted with dichloromethane. The organic phase was evaporated to dryness, dissolved in toluene, and passed through a rapid column chromatography column. The column chromatography solution was evaporated until a small amount of solvent remained, and 500 mL of ethanol was added to slurry the mixture. The solution was filtered to obtain a pink target product, sub-h174 g (99.4%), with a yield of 51%.

[0203] 50 g of sub-h1 (0.18 mol), 37 g of 4-chlorophenylboronic acid (0.24 mol), 50 g of K2CO3 (0.36 mol), 4.2 g of Pd(PPh3)4 (3.6 mmol), 350 mL of toluene, 150 mL of ethanol, and 150 mL of water were added. The mixture was heated to 80 °C under a nitrogen atmosphere, with an internal temperature of 72 °C, and stirred for 2 h. After the reaction was complete, the mixture was quenched with water, and the organic phase was extracted. The resulting organic layer was dried over magnesium sulfate (MgSO4) and concentrated to give 40 g (99%) of sub-h2, with a yield of 73%.

[0204] 40 g sub-h2 (0.13 mol), 15.8 g aniline (0.17 mol), 25 g t-BuONa (0.26 mol), 2.1 g S-Phos (5.2 mmol), 2.4 g Pd2(dba)3 (2.6 mmol), and 400 mL toluene were added. The mixture was heated to 110 °C under a nitrogen atmosphere and stirred for 2 h. After the reaction was complete, the heating was turned off, the temperature was lowered to 80 °C, and the reaction was quenched with water. The organic phase was extracted, and the sample was stirred and column chromatography to obtain 32 g sub-h3 (99%), with a yield of 67%.

[0205] 8 g of intermediate sub-g1 (27 mmol), 10 g of sub-h3 (27 mmol), 5.2 g of t-BuONa (55 mol), 0.45 g of S-Phos (1.1 mmol), 0.5 g of Pd2(dba)3 (0.5 mmol), and 100 mL of toluene were added. The mixture was heated to 110 °C under a nitrogen atmosphere and stirred for 3 h. After the reaction was completed, the temperature was lowered to 80 °C, and the reaction was quenched with water. The organic phase was extracted and purified by column chromatography, pulping, and recrystallization to give 11.7 g of compound S-33 (99.95%), with a yield of 69%.

[0206] Elemental analysis: C43H26N2O3 Theoretical values: C, 83.48; H, 4.24; N, 4.53; O, 7.76; Measured values: C, 83.55; H, 4.22; N, 4.15; HRMS(ESI) m / z [M+H]+: Theoretical value: 618.19; Measured value: 619.2.

[0207] Synthesis Example 2

[0208] This synthetic example provides a nitrogen-containing compound S-126, the synthetic steps of which are shown below:

[0209]

[0210] Sub-h2 (10 g, 32.7 mmol), 3-aminobiphenyl (6.1 g, 36.0 mmol), Pd2(dba)3 (0.60 g, 0.65 mmol), Sphos (0.41 g, 1.3 mmol), t-BuONa (6.3 g, 65.4 mmol), and toluene (100 mL) were synthesized by sub-h2 (10 g, 32.7 mmol), 3-aminobiphenyl (6.1 g, 36.0 mmol), Pd2(dba)3 (0.60 g, 0.65 mmol), Sphos (0.41 g, 1.3 mmol), t-BuONa (6.3 g, 65.4 mmol), and toluene (100 mL) were replaced with the corresponding starting materials. The rest of the synthesis method was the same as that of sub-h3 described above, to obtain 10 g of product sub-h4, with a yield of 70%.

[0211] Sub-h4 (10 g, 22.8 mmol), sub-g7 (6.7 g, 22.8 mmol), Pd2(dba)3 (0.42 g, 0.46 mmol), Sphos (0.37 g, 0.91 mmol), t-BuONa (4.38 g, 45.6 mmol), and toluene (100 mL) were replaced with the corresponding starting materials, while the rest were synthesized in the same manner as S-33 in Example 1, yielding 9.2 g of S-126 (99.95%), with a yield of 58%.

[0212] Elemental analysis: C49H30N2O3 Theoretical values: C, 84.71; H, 4.35; N, 4.03; O, 6.91; Measured values: C, 84.75; H, 4.32; N, 4.08; HRMS(ESI) m / z [M+H]+: Theoretical value: 694.23; Measured value: 695.21.

[0213] Synthesis Example 3

[0214] This synthetic example provides a nitrogen-containing compound S-18, the synthetic steps of which are shown below:

[0215]

[0216] The synthesis method of intermediate sub-h5 is the same as that of intermediate sub-h3, except that the raw materials are replaced with sub-h1 and aniline, and the rest of the operation is the same as the above synthesis method.

[0217] Sub-g6 (5 g, 14.6 mmol), sub-h5 (4.18 g, 14.6 mmol), Pd2(dba)3 (0.27 g, 0.29 mmol), Sphos (0.24 g, 0.58 mmol), t-BuONa (4.02 g, 29.2 mmol), and toluene (100 mL) were synthesized using the same method as S-33 in Example 1, yielding 5.4 g of S-18 (99.95%), with a yield of 63%.

[0218] Elemental analysis: C41H24N2O3 Theoretical values: C, 83.09; H, 4.08; N, 4.73; O, 8.10; Measured values: C, 83.11; H, 4.06; N, 4.79; HRMS(ESI) m / z [M+H]+: Theoretical value: 592.18; Measured value: 593.21.

[0219] Synthesis Example 4

[0220] This synthetic example provides a nitrogen-containing compound S-40, the synthetic steps of which are shown below:

[0221]

[0222] Sub-g7 (5 g, 14.6 mmol), sub-h3 (5.29 g, 14.6 mmol), Pd2(dba)3 (0.27 g, 0.29 mmol), Sphos (0.24 g, 0.58 mmol), t-BuONa (4.02 g, 29.2 mmol), and toluene (100 mL) were synthesized in the same manner as S-33 in Example 1 to obtain 5.6 g of S-40 (99.95%), with a yield of 57%.

[0223] Elemental analysis: C47H28N2O3 Theoretical values: C, 84.41; H, 4.22; N, 4.19; O, 7.18; Measured values: C, 84.46; H, 4.20; N, 4.26; HRMS(ESI) m / z [M+H]+: Theoretical value: 668.21; Measured value: 669.20.

[0224] Synthesis Example 5

[0225] This synthetic example provides a nitrogen-containing compound S-42, the synthetic steps of which are shown below:

[0226]

[0227] In a 1L four-necked flask, 50g of sub-h1 (0.18mol), 27.5g of 4-aminophenylboronic acid (0.20mol), 50g of potassium carbonate (0.36mol), 4.2g of Pd(PPh3)4 (3.6mmol), 350mL of toluene, 150mL of ethanol, and 150mL of water were added sequentially. The mixture was heated to 80℃ under a nitrogen atmosphere, with an internal temperature of 72℃, and stirred for 2 hours. After the reaction was complete, the mixture was quenched with water, and the organic phase was extracted. The resulting organic layer was dried over magnesium sulfate (MgSO4) and concentrated to give 629.8 g (99%) of sub-h, with a yield of 57%.

[0228] Sub-g1 (10.2 g, 34.9 mmol), sub-h6 (10 g, 34.9 mmol), Pd2(dba)3 (0.64 g, 0.7 mmol), Sphos (0.57 g, 1.4 mmol), t-BuONa (6.7 g, 69.8 mmol), and toluene (100 mL) were synthesized using the same method as S-33 in Example 1 to obtain 14 g of sub-h7, with a yield of 74%.

[0229] Sub-h7 (5 g, 9.2 mmol), 2-bromo-9,9-diphenylfluorene (3.7 g, 9.2 mmol), Pd2(dba)3 (0.17 g, 0.18 mmol), Sphos (0.15 g, 0.37 mmol), t-BuONa (1.8 g, 18.4 mmol), and toluene (50 mL) were synthesized in the same manner as S-33 in Example 1 to yield 4.7 g of S-42 (99.95%), with a yield of 59%.

[0230] Elemental analysis: C62H38N2O3 Theoretical values: C, 86.69; H, 4.46; N, 3.26; O, 5.59; Measured values: C, 86.71; H, 4.44; N, 3.30; HRMS(ESI) m / z [M+H]+: Theoretical value: 858.29; Measured value: 859.28.

[0231] Synthesis Example 6

[0232] This synthetic example provides a nitrogen-containing compound S-61, the synthetic steps of which are shown below:

[0233]

[0234] 100 g of 2-amino-5-bromophenol (0.53 mol), 90 g of benzoyl chloride (0.64 mol), and 1 L of ultra-dry 1,4-dioxane were added to a flask under nitrogen protection. The system was placed in a -10°C cryogenic bath, and 90 g of trifluoromethanesulfonic acid was added dropwise to the system at -5 to -10°C over 0.5 to 1 hour. After the addition was complete, the mixture was heated and stirred at 100°C for 2 to 3 hours. The reaction was quenched with water, and the organic phase was extracted with dichloromethane. The organic phase was evaporated to dryness, dissolved in toluene, and passed through a rapid column chromatography column. The column chromatography solution was evaporated until a small amount of solvent remained, and 500 mL of ethanol was added to slurry the mixture. The slurry was filtered to obtain a pink target product, sub-h874 g (99.1%), with a yield of 54%.

[0235] 50 g of sub-h8 (0.18 mol), 37 g of 4-chlorophenylboronic acid (0.24 mol), 50 g of potassium carbonate (0.36 mol), 4.2 g of Pd(PPh3)4 (3.6 mmol), 350 mL of toluene, 150 mL of ethanol, and 150 mL of water were added. The mixture was heated to 80 °C under a nitrogen atmosphere, with an internal temperature of 72 °C, and stirred for 2 h. After the reaction was complete, the mixture was quenched with water, and the organic phase was extracted. The resulting organic layer was dried over magnesium sulfate (MgSO4) and concentrated to give 937.9 g (99%) of sub-h8, with a yield of 68%.

[0236] Sub-h9 (10 g, 32.7 mmol), aniline (3.4 g, 36.0 mmol), Pd2(dba)3 (0.6 g, 0.7 mmol), Sphos (0.54 g, 1.3 mmol), t-BuONa (6.3 g, 65.6 mmol), and toluene (100 mL) were synthesized using the same method as S-33 in Example 1 to obtain 9.8 g of sub-h10, with a yield of 83%.

[0237] Sub-h10 (5.0 g, 13.8 mmol), sub-g11 (4.0 g, 13.8 mmol), Pd2(dba)3 (0.25 g, 0.28 mmol), Sphos (0.23 g, 0.55 mmol), t-BuONa (2.6 g, 27.6 mmol), and toluene (100 mL) were synthesized in the same manner as S-33 in Example 1 to obtain 5.2 g of S-61 (99.95%), with a yield of 61%.

[0238] Elemental analysis: C43H26N2O3 Theoretical values: C, 83.48; H, 4.24; N, 4.53; O, 7.76; Measured values: C, 83.52; H, 4.20; N, 4.63; HRMS(ESI) m / z [M+H]+: Theoretical value: 618.19; Measured value: 619.20.

[0239] Synthesis Example 7

[0240] This synthetic example provides a nitrogen-containing compound S-71, the synthetic steps of which are shown below:

[0241]

[0242] Sub-g9 (5.0 g, 14.6 mmol), sub-h10 (5.3 g, 14.6 mmol), Pd2(dba)3 (0.27 g, 0.29 mmol), Sphos (0.24 g, 0.58 mmol), t-BuONa (2.8 g, 29.2 mmol), and toluene (100 mL) were synthesized in the same manner as S-33 in Example 1 to obtain 6.6 g of S-71 (99.95%), with a yield of 68%.

[0243] Elemental analysis: C47H28N2O3 Theoretical values: C, 84.41; H, 4.22; N, 4.19; O, 7.18; Measured values: C, 84.46; H, 4.19; N, 4.26; HRMS(ESI) m / z [M+H]+: Theoretical value: 668.21; Measured value: 669.20.

[0244] Synthesis Example 8

[0245] This synthetic example provides a nitrogen-containing compound S-103, the synthetic steps of which are shown below:

[0246]

[0247] Sub-g2 (4.0 g, 13.8 mmol), sub-h3 (5.0 g, 13.8 mmol), Pd2(dba)3 (0.25 g, 0.28 mmol), Sphos (0.23 g, 0.55 mmol), t-BuONa (2.6 g, 27.6 mmol), and toluene (100 mL) were synthesized in the same manner as S-33 in Example 1 to obtain 5.2 g of S-103 (99.95%), with a yield of 61%.

[0248] Elemental analysis: C43H26N2O3 Theoretical values: C, 83.48; H, 4.24; N, 4.53; O, 7.76; Measured values: C, 83.51; H, 4.22; N, 4.59; HRMS(ESI) m / z [M+H]+: Theoretical value: 618.19; Measured value: 619.19.

[0249] Synthesis Example 9

[0250] This synthetic example provides a nitrogen-containing compound S-137, the synthetic steps of which are shown below:

[0251]

[0252] Sub-h9 (10 g, 32.7 mmol), 4-aminobiphenyl (6.1 g, 36.0 mmol), Pd2(dba)3 (0.60 g, 0.65 mmol), Sphos (0.41 g, 1.3 mmol), t-BuONa (6.3 g, 65.4 mmol), and toluene (100 mL) were synthesized using the same method as sub-h10 described above, yielding 10.2 g of product sub-h11 in 71% yield.

[0253] Sub-h11 (10 g, 22.8 mmol), sub-g1 (6.7 g, 22.8 mmol), Pd2(dba)3 (0.42 g, 0.46 mmol), Sphos (0.37 g, 0.91 mmol), t-BuONa (4.38 g, 45.6 mmol), and toluene (100 mL) were synthesized in the same manner as S-33 in Example 1 to obtain 9.2 g of S-137 (99.95%), with a yield of 58%.

[0254] Elemental analysis: C49H30N2O3 Theoretical values: C, 84.71; H, 4.35; N, 4.03; O, 6.91; Measured values: C, 84.78; H, 4.31; N, 4.10; HRMS(ESI) m / z [M+H]+: Theoretical value: 694.23; Measured value: 695.23.

[0255] Synthesis Example 10

[0256] This synthetic example provides a nitrogen-containing compound S-139, the synthetic steps of which are shown below:

[0257]

[0258] Sub-h9 (10 g, 32.7 mmol), 2-aminobiphenyl (6.1 g, 36.0 mmol), Pd2(dba)3 (0.60 g, 0.65 mmol), Sphos (0.41 g, 1.3 mmol), t-BuONa (6.3 g, 65.4 mmol), and toluene (100 mL) were synthesized using the same method as sub-g10 described above to obtain 10 g of product sub-h12 in 70% yield.

[0259] Sub-h12 (10 g, 22.8 mmol), sub-g1 (6.7 g, 22.8 mmol), Pd2(dba)3 (0.42 g, 0.46 mmol), Sphos (0.37 g, 0.91 mmol), t-BuONa (4.38 g, 45.6 mmol), and toluene (100 mL) were synthesized in the same manner as S-33 in Example 1 to obtain 9.2 g of S-139 (99.95%), with a yield of 58%.

[0260] Elemental analysis: C49H30N2O3 Theoretical values: C, 84.71; H, 4.35; N, 4.03; O, 6.91; Measured values: C, 84.78; H, 4.30; N, 4.11; HRMS(ESI) m / z [M+H]+: Theoretical value: 694.23; Measured value: 695.21.

[0261] Synthesis Example 11

[0262] This synthetic example provides a nitrogen-containing compound S-147, the synthetic steps of which are shown below:

[0263]

[0264] Sub-g7 (5.0 g, 14.6 mmol), sub-h12 (6.4 g, 14.6 mmol), Pd2(dba)3 (0.27 g, 0.29 mmol), Sphos (0.24 g, 0.58 mmol), t-BuONa (2.8 g, 29.2 mmol), and toluene (100 mL) were synthesized in the same manner as S-33 in Example 1 to obtain 7.1 g of S-147 (99.95%), with a yield of 65%.

[0265] Elemental analysis: C53H32N2O3 Theoretical values: C, 85.46; H, 4.33; N, 3.76; O, 6.44; Measured values: C, 85.48; H, 4.30; N, 3.83; HRMS(ESI) m / z [M+H]+: Theoretical value: 744.24; Measured value: 745.23.

[0266] Synthesis Example 12

[0267] This synthetic example provides a nitrogen-containing compound S-152, the synthetic steps of which are shown below:

[0268]

[0269] Sub-h2 (10 g, 32.7 mmol), 4-(1-naphthyl)aniline (7.9 g, 36.0 mmol), Pd2(dba)3 (0.60 g, 0.65 mmol), Sphos (0.41 g, 1.3 mmol), t-BuONa (6.3 g, 65.4 mmol), and toluene (100 mL) were synthesized using the same method as sub-h3 described above, yielding 11.3 g of product sub-h13 in 71% yield.

[0270] Sub-g8 (5.0 g, 14.6 mmol), sub-h13 (7.1 g, 14.6 mmol), Pd2(dba)3 (0.27 g, 0.29 mmol), Sphos (0.24 g, 0.58 mmol), t-BuONa (2.8 g, 29.2 mmol), and toluene (100 mL) were synthesized in the same manner as S-33 in Example 1 to obtain 7.3 g of S-152 (99.95%), with a yield of 63%.

[0271] Elemental analysis: C57H34N2O3 Theoretical values: C, 86.13; H, 4.31; N, 3.52; O, 6.04; Measured values: C, 86.18; H, 4.27; N, 3.59; HRMS(ESI) m / z [M+H]+: Theoretical value: 794.26; Measured value: 795.22.

[0272] Synthesis Example 13

[0273] This synthetic example provides a nitrogen-containing compound S-156, the synthetic steps of which are shown below:

[0274]

[0275] Sub-h2 (10 g, 32.7 mmol), 4-(1-naphthyl)aniline (7.9 g, 36.0 mmol), Pd2(dba)3 (0.60 g, 0.65 mmol), Sphos (0.41 g, 1.3 mmol), t-BuONa (6.3 g, 65.4 mmol), and toluene (100 mL) were synthesized using the same method as sub-h3 described above, yielding 11.3 g of product sub-h13 in 71% yield.

[0276] Sub-g8 (5.0 g, 14.6 mmol), sub-h13 (7.1 g, 14.6 mmol), Pd2(dba)3 (0.27 g, 0.29 mmol), Sphos (0.24 g, 0.58 mmol), t-BuONa (2.8 g, 29.2 mmol), and toluene (100 mL) were synthesized in the same manner as S-33 in Example 1 to obtain 7.3 g of S-156 (99.95%), with a yield of 63%.

[0277] Elemental analysis: C57H34N2O3 Theoretical values: C, 86.13; H, 4.31; N, 3.52; O, 6.04; Measured values: C, 86.18; H, 4.27; N, 3.59; HRMS(ESI) m / z [M+H]+: Theoretical value: 794.26; Measured value: 795.22.

[0278] Synthesis Example 14

[0279] This synthetic example provides a nitrogen-containing compound S-171, the synthetic steps of which are shown below.

[0280]

[0281] 1-Bromodibenzofuran (10 g, 40.5 mmol), p-chlorophenylboronic acid (7.0 g, 44.5 mmol), Pd(PPh3)4 (0.93 g, 0.81 mmol), K2CO3 (11.2 g, 80.9 mmol), and toluene (100 mL) were synthesized using the same method as for sub-b1 described above, yielding 9.7 g of product sub-h14 in 86% yield.

[0282] Sub-h14 (10 g, 35.9 mmol), sub-h6 (10.3 g, 36.0 mmol), Pd2(dba)3 (0.66 g, 0.72 mmol), Sphos (0.59 g, 1.4 mmol), t-BuONa (6.9 g, 71.8 mmol), and toluene (100 mL) were synthesized using the same method as sub-h7 described above, yielding 16.1 g of product sub-h15 in 85% yield.

[0283] Sub-h15 (10 g, 18.9 mmol), sub-g5 (5.5 g, 18.9 mmol), Pd2(dba)3 (0.35 g, 0.38 mmol), Sphos (0.31 g, 0.76 mmol), t-BuONa (3.6 g, 37.8 mmol), and toluene (100 mL) were synthesized in the same manner as S-33 in Example 1 to obtain 10.1 g of S-171 (99.95%), with a yield of 68%.

[0284] Elemental analysis: Theoretical values ​​for C55H32N2O4: C, 84.17; H, 4.11; N, 3.57; O, 8.15; Measured values: C, 84.20; H, 4.07; N, 3.61; HRMS(ESI) m / z [M+H]+: Theoretical value: 784.24; Measured value: 785.24.

[0285] Synthesis Example 15

[0286] This synthetic example provides a nitrogen-containing compound S-182, the synthetic steps of which are shown below:

[0287]

[0288] 2-Bromobiphenyl (10 g, 42.9 mmol), 3-aminophenylboronic acid (5.9 g, 45 mmol), Pd(PPh3)4 (0.99 g, 0.86 mmol), K2CO3 (11.8 g, 85.8 mmol), toluene (100 mL), and water (70 mL) were synthesized using the same method as for sub-h2 described above, yielding 8.7 g of product sub-h16 in 83% yield.

[0289] Sub-h16 (9 g, 36.7 mmol), sub-h9 (11.2 g, 36.7 mmol), Pd2(dba)3 (0.67 g, 0.73 mmol), Sphos (0.60 g, 1.5 mmol), t-BuONa (6.5 g, 73 mmol), and toluene (100 mL) were synthesized using the same method as sub-h10 described above, yielding 14.5 g of product sub-h17 in 77% yield.

[0290] Sub-h17 (10 g, 19.4 mmol), sub-g (25.7 g, 19.4 mmol), Pd2(dba)3 (0.36 g, 0.39 mmol), Sphos (0.32 g, 0.78 mmol), t-BuONa (3.7 g, 38.9 mmol), and toluene (100 mL) were synthesized in the same manner as S-33 in Example 1 to obtain 10.2 g of S-182 (99.95%), with a yield of 68%.

[0291] Elemental analysis: C55H34N2O3 Theoretical values: C, 85.69; H, 4.45; N, 3.63; O, 6.23; Measured values: C, 85.72; H, 4.41; N, 3.71; HRMS(ESI) m / z [M+H]+: Theoretical value: 770.26; Measured value: 771.25.

[0292] Synthesis Example 16

[0293] This synthetic example provides a nitrogen-containing compound S-277, the synthetic steps of which are shown below:

[0294]

[0295] The product sub-h18 was obtained by the same method as that used for sub-h9 above (yield: 83%).

[0296] The product sub-h19 was obtained using the same method as described above for the synthesis of sub-h9 (yield: 81%).

[0297] The product sub-h20 was obtained by the same method as that used for sub-h16 above (yield: 86%).

[0298] Sub-h19 (10 g, 32.7 mmol), sub-h20 (8.0 g, 32.7 mmol), Pd2(dba)3 (0.60 g, 0.65 mmol), Sphos (0.54 g, 1.3 mmol), t-BuONa (6.3 g, 65.4 mmol), and toluene (100 mL) were synthesized using the same method as sub-h10 described above, yielding 11.4 g of product sub-h21 in 68% yield.

[0299] Sub-h21 (10 g, 19.4 mmol), K (5.7 g, 19.4 mmol), Pd2(dba)3 (0.36 g, 0.39 mmol), Sphos (0.32 g, 0.78 mmol), t-BuONa (3.7 g, 38.9 mmol), and toluene (100 mL) were synthesized in the same manner as S-33 in Example 1 to obtain 8.2 g of S-277 (99.95%), with a yield of 55%.

[0300] Elemental analysis: C55H34N2O3 Theoretical values: C, 85.69; H, 4.45; N, 3.63; O, 6.23; Measured values: C, 85.72; H, 4.41; N, 3.71; HRMS(ESI) m / z [M+H]+: Theoretical value: 770.26; Measured value: 771.25.

[0301] Synthesis Example 17

[0302] Compound S-86 was prepared using the same method as in Example 3, except that sub-g4 was used instead of sub-g6, and (CAS: 3048379-23-0) sub-h5 was used instead of sub-h5. The specific synthetic route is shown below:

[0303]

[0304] Compound S-86 was obtained in 71% yield. Elemental analysis: theoretical values ​​C, 83.48; H, 4.24; N, 4.53; O, 7.76; measured values ​​C, 83.49; H, 4.27; N, 4.49. HRMS (ESI) m / z [M+H]+: theoretical value: 618.19; measured value: 619.11.

[0305] Synthesis Example 18

[0306] Compound S-305 was prepared using the method described in Example 6, except that sub305-A was used instead of 2-amino-5-bromophenol and sub-g4 was used instead of sub-g11. The specific synthetic route is shown below:

[0307]

[0308] Compound S-305 was obtained in 72% yield. Elemental analysis: theoretical values: C, 83.48; H, 4.24; N, 4.53; O, 7.76; measured values: C, 83.51; H, 4.28; N, 4.46. HRMS (ESI) m / z [M+H]+: theoretical value: 618.19; measured value: 619.32.

[0309] Synthesis Example 19

[0310] Compound S-306 was prepared in accordance with the method described in Example 6, except that the starting material sub306-A was used instead of 2-amino-5-bromophenol and sub-g4 was used instead of sub-g11. The specific synthetic route is shown below:

[0311]

[0312] Compound S-306 was obtained in 74% yield. Elemental analysis: theoretical values: C, 83.48; H, 4.24; N, 4.53; O, 7.76; measured values: C, 83.50; H, 4.27; N, 4.48. HRMS (ESI) m / z [M+H]+: theoretical value: 618.19; measured value: 619.29.

[0313] Synthesis Example 20

[0314] Compound S-307 was prepared using the method described in Example 6, except that sub307-A was used instead of 2-amino-5-bromophenol and sub-g4 was used instead of sub-g11. The specific synthetic route is shown below:

[0315]

[0316] Compound S-307 was obtained in 69% yield. Elemental analysis: theoretical values: C, 83.48; H, 4.24; N, 4.53; O, 7.76; measured values: C, 83.52; H, 4.28; N, 4.45. HRMS (ESI) m / z [M+H]+: theoretical value: 618.19; measured value: 619.19.

[0317] Device Examples

[0318] The materials used to prepare the following device embodiments or device comparative examples are shown in Table 1 below.

[0319] Table 1

[0320]

[0321]

[0322] Device Example 1

[0323] This embodiment provides an organic electroluminescent device, such as... Figure 1As shown, the device includes an anode 2, a hole injection layer 3, a hole transport layer 4, a light-emitting layer 5, an electron transport layer 6, an electron injection layer 7, and a cathode 8, which are sequentially stacked on a substrate 1. The device structure is as follows: anode (indium tin oxide (ITO) coated glass substrate) / hole injection layer (HIL) / hole transport layer (HTL) / electron blocking layer (EBL) / light-emitting layer (EML) / hole blocking layer (HBL) / electron transport layer (ETL) / electron injection layer (EIL) / cathode (Al).

[0324] The specific preparation process is as follows:

[0325] 1) Substrate cleaning:

[0326] The glass substrate coated with transparent ITO was ultrasonically treated in an aqueous cleaning agent (the composition and concentration of the aqueous cleaning agent: ethylene glycol solvent ≤10wt%, triethanolamine ≤1wt%), then rinsed in deionized water, ultrasonically degreased in a mixed solvent of acetone and ethanol (volume ratio of acetone and ethanol 1:1), baked in a clean environment until all moisture was removed, and then cleaned with ultraviolet light and ozone.

[0327] 2) Preparation of organic layer:

[0328] The ITO transparent substrate was transferred to an evaporation equipment and vacuumed to 1×10⁻⁶. -6 Up to 2×10 -4 Pa, hole injection layer (HIL) / hole transport layer (HTL) / light emission layer (EML) / electron transport layer (ETL) / electron injection layer (EIL) / thick cathode (Al) are sequentially deposited on the anode film.

[0329] in:

[0330] The hole injection layer (HIL) is a mixture of HAT-CN and HT, with a mass ratio of HAT-CN to HT of 3:97, a thickness of 10 nm, and a total evaporation rate of 0.1 nm / s.

[0331] The hole transport layer (HTL) is made of HT material, has a thickness of 80 nm, and a total evaporation rate of 0.1 nm / s.

[0332] The light-emitting layer (EML) is vacuum-deposited by co-evaporation. The material of the light-emitting layer includes a host material and a guest material, wherein the guest material is RD, and the host material is composed of the compounds of Synthesis Example 1 and R-1. The specific ratio of the host material and the guest material is shown in Table 2 below. The thickness is 35 nm, and the total evaporation rate is 0.1 nm / s.

[0333] The electron transport layer (ETL) is a binary mixture of ET and LiQ in a mass ratio of 1:1, with a thickness of 30 nm and a total evaporation rate of 0.1 nm / s.

[0334] The electron injection layer (EIL) is made of LiQ with a thickness of 1 nm and a total evaporation rate of 0.1 nm / s.

[0335] The cathode is made of aluminum with a thickness of 90 nm and a deposition rate of 1 nm / s.

[0336] Device Example 2

[0337] Compared with Device Example 1, it is almost identical, except that material S-33 in Device Example 1 is replaced with S-126 in Synthesis Example 2. The specific ratios of the host material and the guest material are shown in Table 2 below.

[0338] Device Example 3

[0339] Compared with Device Example 1, it is almost identical, except that material S-33 in Device Example 1 is replaced by S-18 in Synthesis Example 3. The specific ratios of the host material and the guest material are shown in Table 2 below.

[0340] Device Example 4

[0341] Compared with Device Example 1, it is almost identical, except that material S-33 in Device Example 1 is replaced with S-40 in Synthesis Example 4. The specific ratios of the host material and the guest material are shown in Table 2 below.

[0342] Device Example 5

[0343] Compared with Device Example 1, it is largely the same, except that material S-33 in Device Example 1 is replaced by S-42 in Synthesis Example 5. The specific ratios of the host material and the guest material are shown in Table 2 below.

[0344] Device Example 6

[0345] Compared with Device Example 1, it is almost identical, except that material S-33 in Device Example 1 is replaced with S-61 in Synthesis Example 6. The specific ratios of the host material and the guest material are shown in Table 2 below.

[0346] Device Example 7

[0347] Compared with Device Example 1, it is almost identical, except that material S-33 in Device Example 1 is replaced by S-71 in Synthesis Example 7. The specific ratios of the host material and the guest material are shown in Table 2 below.

[0348] Device Example 8

[0349] Compared with Device Example 1, it is almost identical, except that material S-33 in Device Example 1 is replaced by S-103 in Synthesis Example 8. The specific ratio of the host material and the guest material is shown in Table 2 below.

[0350] Device Example 9

[0351] Compared with Device Example 1, it is almost identical, except that material S-33 in Device Example 1 is replaced by S-137 in Synthesis Example 9. The specific ratios of the host material and the guest material are shown in Table 2 below.

[0352] Device Example 10

[0353] Compared with Device Example 1, it is almost identical, except that material S-33 in Device Example 1 is replaced by S-139 in Synthesis Example 10. The specific ratio of the host material and the guest material is shown in Table 2 below.

[0354] Device Example 11

[0355] Compared with Device Example 1, it is almost identical, except that material S-33 in Device Example 1 is replaced by S-147 in Synthesis Example 11. The specific ratio of the host material and the guest material is shown in Table 2 below.

[0356] Device Example 12

[0357] Compared with Device Example 1, it is almost identical, except that material S-33 in Device Example 1 is replaced by S-152 in Synthesis Example 12. The specific ratios of the host material and the guest material are shown in Table 2 below.

[0358] Device Example 13

[0359] Compared with Device Example 1, it is almost identical, except that material S-33 in Device Example 1 is replaced by S-156 in Synthesis Example 13. The specific ratio of the host material and the guest material is shown in Table 2 below.

[0360] Device Example 14

[0361] Compared with Device Example 1, it is almost identical, except that material S-33 in Device Example 1 is replaced by S-171 in Synthesis Example 14. The specific ratio of the host material and the guest material is shown in Table 2 below.

[0362] Device Example 15

[0363] Compared with Device Example 1, it is almost identical, except that material S-33 in Device Example 1 is replaced by S-182 in Synthesis Example 15. The specific ratio of the host material and the guest material is shown in Table 2 below.

[0364] Device Example 16

[0365] Compared with Device Example 1, it is almost identical, except that material S-33 in Device Example 1 is replaced by S-277 in Synthesis Example 16. The specific ratios of the host material and the guest material are shown in Table 2 below.

[0366] Device Example 17

[0367] Compared with Device Example 1, it is almost identical, except that material S-33 in Device Example 1 is replaced by S-86 in Synthesis Example 17. The specific ratios of the host material and the guest material are shown in Table 2 below.

[0368] Device Example 18

[0369] Compared with Device Example 1, it is almost identical, except that material S-33 in Device Example 1 is replaced with S-305 in Synthesis Example 18. The specific ratio of the host material and the guest material is shown in Table 2 below.

[0370] Device Example 19

[0371] Compared with Device Example 1, it is almost identical, except that material S-33 in Device Example 1 is replaced with S-306 in Synthesis Example 19. The specific ratio of the host material and the guest material is shown in Table 2 below.

[0372] Device Example 20

[0373] Compared with Device Example 1, it is almost identical, except that material S-33 in Device Example 1 is replaced with S-307 in Synthesis Example 20. The specific ratio of the host material and the guest material is shown in Table 2 below.

[0374] Device Comparison Example 1

[0375] Compared with Device Example 1, it is almost identical, except that material S-33 in Device Example 1 is changed to the following structure REF-1. The specific ratio of the host material and the guest material is shown in Table 2 below.

[0376]

[0377] Device Comparison Example 2

[0378] Compared with Device Example 1, it is largely the same, except that material S-33 in Device Example 1 is changed to the following structure REF-2. The specific ratio of the host material and the guest material is shown in Table 2 below.

[0379]

[0380] Device Comparison Example 3

[0381] Compared with Device Example 1, it is almost identical, except that material S-33 in Device Example 1 is changed to the following structure REF-3. The specific ratio of the host material and the guest material is shown in Table 2 below.

[0382]

[0383] Compound REF-3 was prepared using the same method as in Example 3, except that sub-g1 was used instead of sub-g6, and (CAS: 1643848-13-8) was used instead of sub-h5. The specific synthetic route is shown below:

[0384]

[0385] Compound REF-3 was obtained in 66% yield. Elemental analysis: theoretical values ​​C, 81.90; H, 4.09; N, 5.16; O, 8.85; measured values ​​C, 81.92; H, 4.11; N, 5.12. HRMS (ESI) m / z [M+H]+: theoretical value: 543.17; measured value: 544.19.

[0386] Table 3 shows the light-emitting layer, its material, and thickness in organic electroluminescent devices:

[0387] Table 2

[0388] Serial Number EML / Thickness Device Example 1 S-33:R-1:RD (mass ratio 47.5:47:5.5) / 35nm Device Example 2 S-126:R-1:RD (mass ratio 47.5:47:5.5) / 35nm Device Example 3 S-18:R-1:RD (mass ratio 47.5:47:5.5) / 35nm Device Example 4 S-40:R-1:RD (mass ratio 47.5:47:5.5) / 35nm Device Example 5 S-42:R-1:RD (mass ratio 47.5:47:5.5) / 35nm Device Example 6 S-61:R-1:RD (mass ratio 47.5:47:5.5) / 35nm Device Example 7 S-71:R-1:RD (mass ratio 47.5:47:5.5) / 35nm Device Example 8 S-103:R-1:RD (mass ratio 47.5:47:5.5) / 35nm Device Example 9 S-137:R-1:RD (mass ratio 47.5:47:5.5) / 35nm Device Example 10 S-139:R-1:RD (mass ratio 47.5:47:5.5) / 35nm Device Example 11 S-147:R-1:RD (mass ratio 47.5:47:5.5) / 35nm Device Example 12 S-152:R-1:RD (mass ratio 47.5:47:5.5) / 35nm Device Example 13 S-156:R-1:RD (mass ratio 47.5:47:5.5) / 35nm Device Example 14 S-171:R-1:RD (mass ratio 47.5:47:5.5) / 35nm Device Example 15 S-182:R-1:RD (mass ratio 47.5:47:5.5) / 35nm Device Example 16 S-277:R-1:RD (mass ratio 47.5:47:5.5) / 35nm Device Example 17 S-86:R-1:RD (mass ratio 47.5:47:5.5) / 35nm Device Example 18 S-305:R-1:RD (mass ratio 47.5:47:5.5) / 35nm Device Example 19 S-306:R-1:RD (mass ratio 47.5:47:5.5) / 35nm Device Example 20 S-307:R-1:RD (mass ratio 47.5:47:5.5) / 35nm Device Comparison Example 1 REF-1:R-1:RD (mass ratio 47.5:47:5.5) / 35nm Device Comparison Example 2 REF-2:R-1:RD (mass ratio 47.5:47:5.5) / 35nm Device Comparison Example 3 REF-3:R-1:RD (mass ratio 47.5:47:5.5) / 35nm

[0389] Device Test Examples

[0390] The organic electroluminescent devices obtained in Device Examples 1-16 and Device Comparative Examples 1-2 in the device examples were tested.

[0391] Instruments: The current, voltage, brightness, emission spectrum and other characteristics of the device were tested simultaneously using a PR 650 spectral scanning luminance meter and a Keithley K 2400 digital source meter system;

[0392] Test conditions: Photoelectric property test conditions: current density 10 mA / cm² 2 .

[0393] Lifetime test: Current density 10mA / cm 2 The time (in hours) when the device brightness drops to 95% of its original brightness is recorded. The lifetime T95 of device comparative example 1 is set to 100, and the lifetimes of other devices are relative values ​​to the lifetimes of device comparative example 1.

[0394] The device performance test results are shown in Table 3:

[0395] Table 3

[0396] Serial Number Drive voltage (V) Current efficiency (Cd / A) Relative lifespan T95 Device Example 1 2.99 39.54 231 Device Example 2 3.01 37.45 215 Device Example 3 3.01 35.32 181 Device Example 4 2.98 35.71 191 Device Example 5 3.00 36.12 198 Device Example 6 3.01 38.76 227 Device Example 7 3.02 35.79 194 Device Example 8 2.99 38.13 219 Device Example 9 2.98 37.64 217 Device Example 10 3.02 37.11 211 Device Example 11 3.03 35.68 188 Device Example 12 3.00 35.46 183 Device Example 13 2.99 35.64 185 Device Example 14 3.01 35.98 187 Device Example 15 2.98 36.89 207 Device Example 16 3.02 36.68 204 Device Example 17 3.01 38.57 225 Device Example 18 3.00 37.79 220 Device Example 19 2.99 37.88 221 Device Example 20 2.98 38.45 224 Device Comparison Example 1 3.13 22.34 100 Device Comparison Example 2 3.27 20.91 89 Device Comparison Example 3 3.15 21.78 97

[0397] Obviously, the above embodiments are merely illustrative examples for clear explanation and are not intended to limit the implementation. Those skilled in the art will recognize that other variations or modifications can be made based on the above description. It is neither necessary nor possible to exhaustively list all possible implementations here. However, obvious variations or modifications derived therefrom are still within the scope of protection of this invention.

Claims

1. An organic electroluminescent compound, characterized by having a structure represented by the following formula (1): In the formula, X1, X2, X3are each independently selected from O, S or NR2; L1, L2, L3are each independently selected from a single bond or substituted or unsubstituted C6-C60arylene; Ar1and Ar2are the same or different, and each is independently selected from substituted or unsubstituted C6-C60aryl or substituted or unsubstituted C1-C60heteroaryl; R1and R2are the same or different, and each is independently selected from hydrogen, deuterium, halogen, hydroxyl, nitro, amidino, hydrazine, substituted or unsubstituted C1-C60alkyl, substituted or unsubstituted C2-C60alkenyl, substituted or unsubstituted C2-C60alkynyl, substituted or unsubstituted C3-C60cycloalkyl, substituted or unsubstituted C1-C60heterocycloalkyl, substituted or unsubstituted C3-C60cycloalkenyl, substituted or unsubstituted C1-C60heterocycloalkenyl, substituted or unsubstituted C6-C60aryl, substituted or unsubstituted C1-C60heteroaryl; Ring A is selected from substituted or unsubstituted C6-C60aromatic ring or substituted or unsubstituted C3-C60heteroaromatic ring; n is selected from an integer from 0 to 3; the substituents in the substituted C1-C60alkyl, substituted C2-C60alkenyl, substituted C2-C60alkynyl, substituted C3-C60cycloalkyl, substituted C1-C60heterocycloalkyl, substituted C3-C60cycloalkenyl, substituted C1-C60heterocycloalkenyl, substituted C6-C60aryl, substituted C6-C60arylene, substituted C1-C60heteroaryl, substituted C6-C60aromatic ring, and substituted C3-C60heteroaromatic ring are selected from one or more of deuterium, halogen, cyano, hydroxyl, nitro, amidino, hydrazine, C1-C60alkyl, C2-C60alkenyl, C3-C60cycloalkyl, C2-C60alkynyl, C3-C60cycloalkyl, C1-C60heterocycloalkyl, C3-C60cycloalkenyl, C1-C60heterocycloalkenyl, C6-C60aryl, C1-C60heteroaryl.

2. The organic electroluminescence compound according to claim 1, wherein The organic electroluminescent compound at least comprises one of the following structures: In formula (1-1) to formula (1-25), X1, X2are selected from O, S or NR2, and X3is selected from O or S.

3. The organic electroluminescence compound according to claim 1 or 2, characterized by L1, L2and L3are each independently selected from a single bond or substituted or unsubstituted C6-C50arylene; wherein the substituents in the substituted C6-C50arylene are each independently selected from one or more of deuterium, halogen, cyano, hydroxyl, nitro, amidino, hydrazine, C1-C50alkyl, C2-C50alkenyl, C3-C50cycloalkyl, C2-C50alkynyl, C3-C50cycloalkyl, C1-C50heterocycloalkyl, C3-C50cycloalkenyl, C1-C50heterocycloalkenyl, C6-C50aryl, C1-C50heteroaryl; Preferably, L1, L2and L3are each independently selected from a single bond or substituted or unsubstituted C6-C25arylene; Preferably, L1, L2and L3are each independently selected from a single bond or substituted or unsubstituted C6-C25arylene; Preferably, the substituents in the substituted C6-C25arylene group are each independently selected from one or more of deuterium, halogen, cyano, hydroxyl, nitro, amidino, hydrazino, C1-C25alkyl, C2-C25alkenyl, C3-C25cycloalkyl, C2-C25alkynyl, C3-C25cycloalkyl, C1-C25heterocycloalkyl, C3-C25cycloalkenyl, C1-C25heterocycloalkenyl, C6-C25aryl, C1-C25heteroaryl; Preferably, L1, L2and L3are selected from the group consisting of a single bond or:

4. The organic electroluminescence compound according to any one of claims 1 to 3, characterized by Ar1and Ar2are each independently selected from substituted or unsubstituted C6-C50aryl or substituted or unsubstituted C1-C50heteroaryl; wherein the substituents in the substituted C6-C50aryl, substituted C1-C50heteroaryl are selected from one or more of deuterium, halogen, cyano, hydroxyl, nitro, amidino, hydrazino, C1-C50alkyl, C2-C50alkenyl, C3-C50cycloalkyl, C2-C50alkynyl, C3-C50cycloalkyl, C1-C50heterocycloalkyl, C3-C50cycloalkenyl, C1-C50heterocycloalkenyl, C6-C50aryl, C1-C50heteroaryl; Preferably, Ar1and Ar2are each independently selected from substituted or unsubstituted C6-C25aryl or substituted or unsubstituted C1-C25heteroaryl; wherein the substituents in the substituted C6-C25aryl, substituted C1-C25heteroaryl are selected from one or more of deuterium, halogen, cyano, hydroxyl, nitro, amidino, hydrazino, C1-C25alkyl, C2-C25alkenyl, C3-C25cycloalkyl, C2-C25alkynyl, C3-C25cycloalkyl, C1-C25heterocycloalkyl, C3-C25cycloalkenyl, C1-C25heterocycloalkenyl, C6-C25aryl, C1-C25heteroaryl; Preferably, Ar1and Ar2are each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted binaphthyl, substituted or unsubstituted phenylnaphthyl, substituted or unsubstituted naphthylphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenylfluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted dibenzofluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted phenylphenanthryl, substituted or unsubstituted anthryl, substituted or unsubstituted indenyl, substituted or unsubstituted naphthacenyl, substituted or unsubstituted perylenyl, substituted or unsubstituted tetracenyl, substituted or unsubstituted chrysenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted furanyl, substituted or unsubstituted thiophenyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted pyrazolyl, substituted or unsubstituted thiazolyl, substituted or unsubstituted thiadiazolyl, substituted or unsubstituted isothiazolyl, substituted or unsubstituted isoxazolyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted oxadiazolyl, substituted or unsubstituted triazinyl, substituted or unsubstituted tetrazinyl, substituted or unsubstituted triazolyl, substituted or unsubstituted tetrazolyl, substituted or unsubstituted furazanyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted isobenzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzoimidazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted benzoisothiazolyl, substituted or unsubstituted benzoisoxazolyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted isoindolyl, substituted or unsubstituted indolyl, substituted or unsubstituted indazolyl, substituted or unsubstituted benzothiadiazolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted cinnolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted phenanthridinyl, substituted or unsubstituted bispyridinyl, substituted or unsubstituted terpyridinyl, substituted or unsubstituted phenylterpyridinyl, or substituted or unsubstituted diazastilbene, or phenoxazinyl; wherein the substituents in the substituted groups are selected from one or more of deuterium, halogen, cyano, hydroxyl, nitro, amidine, hydrazine, methyl, ethyl, iso-propyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, phenyl, naphthyl, biphenyl, binaphthyl, terphenyl, fluorenyl, dibenzofuranyl, dibenzothiophenyl, or carbazolyl; Preferably, Ar1and Ar2are each independently selected from the group consisting of:

5. The organic electroluminescence compound according to any one of claims 1 to 4, characterized by R1and R2are each independently selected from the group consisting of hydrogen, deuterium, halogen, hydroxyl, nitro, amidino, hydrazino, substituted or unsubstituted C1-C50alkyl, substituted or unsubstituted C2-C50alkenyl, substituted or unsubstituted C2-C50alkynyl, substituted or unsubstituted C3-C50cycloalkyl, substituted or unsubstituted C1-C50heterocycloalkyl, substituted or unsubstituted C3-C50cycloalkenyl, substituted or unsubstituted C1-C50heterocycloalkenyl, substituted or unsubstituted C6-C50aryl, substituted or unsubstituted C1-C50heteroaryl; wherein the substituents in the substituted C1-C50alkyl, substituted C2-C50alkenyl, substituted C2-C50alkynyl, substituted C3-C50cycloalkyl, substituted C1-C50heterocycloalkyl, substituted C3-C50cycloalkenyl, substituted C1-C50heterocycloalkenyl, substituted C6-C50aryl, substituted C1-C50heteroaryl are selected from one or more of deuterium, halogen, cyano, hydroxyl, nitro, amidino, hydrazino, C1-C50alkyl, C2-C50alkenyl, C3-C50cycloalkyl, C2-C50alkynyl, C3-C50cycloalkyl, C1-C50heterocycloalkyl, C3-C50cycloalkenyl, C1-C50heterocycloalkenyl, C6-C50aryl, C1-C50heteroaryl; Preferably, R1and R2are each independently selected from the group consisting of hydrogen, deuterium, halogen, hydroxyl, nitro, amidino, hydrazino, substituted or unsubstituted C1-C25alkyl, substituted or unsubstituted C2-C25alkenyl, substituted or unsubstituted C2-C25alkynyl, substituted or unsubstituted C3-C25cycloalkyl, substituted or unsubstituted C1-C25heterocycloalkyl, substituted or unsubstituted C3-C25cycloalkenyl, substituted or unsubstituted C1-C25heterocycloalkenyl, substituted or unsubstituted C6-C25aryl, substituted or unsubstituted C1-C25heteroaryl; wherein the substituents in the substituted C1-C25alkyl, substituted C2-C25alkenyl, substituted C2-C25alkynyl, substituted C3-C25cycloalkyl, substituted C1-C25heterocycloalkyl, substituted C3-C25cycloalkenyl, substituted C1-C25heterocycloalkenyl, substituted C6-C25aryl, substituted C1-C25heteroaryl are selected from one or more of deuterium, halogen, cyano, hydroxyl, nitro, amidino, hydrazino, C1-C25alkyl, C2-C25alkenyl, C3-C25cycloalkyl, C2-C25alkynyl, C3-C25cycloalkyl, C1-C25heterocycloalkyl, C3-C25cycloalkenyl, C1-C25heterocycloalkenyl, C6-C25aryl, C1-C25heteroaryl; Preferably, R1and R2are each independently selected from deuterium, halogen, cyano, hydroxyl, nitro, amidino, hydrazino, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted binaphthyl, substituted or unsubstituted phenylnaphthyl, substituted or unsubstituted naphthylphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenylfluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted dibenzofluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted phenylphenanthryl, substituted or unsubstituted anthryl, substituted or unsubstituted indenyl, substituted or unsubstituted naphthacenyl, substituted or unsubstituted perylenyl, substituted or unsubstituted tetracenyl, substituted or unsubstituted chrysenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted furanyl, substituted or unsubstituted thiophenyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted pyrazolyl, substituted or unsubstituted thiazolyl, substituted or unsubstituted thiadiazolyl, substituted or unsubstituted isothiazolyl, substituted or unsubstituted isoxazolyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted oxadiazolyl, substituted or unsubstituted triazinyl, substituted or unsubstituted tetrazinyl, substituted or unsubstituted triazolyl, substituted or unsubstituted tetrazolyl, substituted or unsubstituted furazanyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted isobenzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzoimidazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted benzoisothiazolyl, substituted or unsubstituted benzoisoxazolyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted isoindolyl, substituted or unsubstituted indolyl, substituted or unsubstituted indazolyl, substituted or unsubstituted benzothiadiazolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted cinnolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted phenanthridinyl, substituted or unsubstituted bipyridinyl, substituted or unsubstituted terpyridinyl, substituted or unsubstituted phenylterpyridinyl, or substituted or unsubstituted diazaindacene, or phenoxazine; wherein the substituents in the substituted groups are selected from one or more of deuterium, halogen, cyano, hydroxyl, nitro, amidino, hydrazino, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, phenyl, naphthyl, biphenyl, binaphthyl, terphenyl, fluorenyl, dibenzofuranyl, dibenzothiophenyl, or carbazolyl; Preferably, R1and R2are each independently selected from hydrogen, deuterium, or the group consisting of:

6. The organic electroluminescence compound according to any one of claims 1 to 5, characterized by Ring A is selected from a substituted or unsubstituted C6-C50 aryl ring or a substituted or unsubstituted C3-C50 heteroaryl ring; wherein the substituents in the substituted C6-C50 aryl ring or the substituted C3-C50 heteroaryl ring are selected from one or more of deuterium, halogen, cyano, hydroxyl, nitro, amidine, hydrazine, C1-C60 alkyl, C2-C60 alkenyl, C3-C60 cycloalkyl, C2-C60 alkynyl, C3-C60 cycloalkyl, C1-C60 heterocycloalkyl, C3-C60 cycloalkenyl, C1-C60 heterocycloalkenyl, C6-C60 aryl, C1-C60 heteroaryl; Preferably, Ring A is selected from a substituted or unsubstituted benzene, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthalene, a substituted or unsubstituted binaphthalene, a substituted or unsubstituted fluorene, a substituted or unsubstituted dibenzofluorene, a substituted or unsubstituted phenanthrene, a substituted or unsubstituted furan, a substituted or unsubstituted benzene sulfide, a substituted or unsubstituted pyrrole, a substituted or unsubstituted imidazole, a substituted or unsubstituted benzofuran, a substituted or unsubstituted benzothiophene, a substituted or unsubstituted dibenzofuran, a substituted or unsubstituted dibenzothiophene; wherein the substituents in the substituted ring are selected from one or more of deuterium, halogen, cyano, hydroxyl, nitro, amidine, hydrazine, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, phenyl, naphthyl, biphenyl, binaphthyl, terphenyl, fluorenyl, dibenzofuranyl, dibenzothiophenyl, or carbazoyl.

7. The organic electroluminescence compound according to any one of claims 1 to 6, characterized by The organic electroluminescent compound is selected from one of the following structures:

8. An organic electroluminescent material, characterized in that, The organic electroluminescent material comprises the organic electroluminescent compound according to any one of claims 1-7.

9. An organic electroluminescent device, characterized by The organic electroluminescent device comprises a first electrode, a second electrode disposed opposite to the first electrode, and at least one organic layer interposed between the first electrode and the second electrode, wherein the organic layer comprises the organic electroluminescent compound according to any one of claims 1-7 or the organic electroluminescent material according to claim 8.

10. Use of the organic electroluminescent device according to claim 9 in an optical fiber device, a lighting device, an electrophotographic photoreceptor device, a photoelectric converter, an organic solar cell, a switching element device, an organic light emitting field effect transistor, an image sensor, or a dye laser.

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