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] R is selected from hydrogen, deuterium, halogen, cyano, hydroxyl, nitro, substituted or unsubstituted C1-C60 alkyl, substituted or unsubstituted C2-C60 alkenyl, substituted or unsubstituted C3-C60 cycloalkyl, 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;

[0008] n is selected from integers from 0 to 7. When n is greater than 1, multiple R can exist independently or combine with each other to form substituted or unsubstituted C6-C30 aromatic rings.

[0009] X and Y are each independently selected from O and S;

[0010] L1 and L2 are each independently selected from single-bonded, substituted or unsubstituted C6-C60 aryl groups;

[0011] Ar1 and Ar2 are each independently selected from substituted or unsubstituted C6-C60 aryl groups and substituted or unsubstituted C1-C60 heteroaryl groups;

[0012] The substituted C1-C60 alkyl, substituted C2-C60 alkenyl, substituted C3-C60 cycloalkyl, substituted C2-C60 ynyl, substituted C3-C60 cycloalkyl, substituted C1-C60 heterocyclic alkyl, substituted C3-C60 cycloalkenyl, substituted C1-C60 heterocyclic alkenyl, substituted C6-C60 arylene, substituted C6-C60 aryl, substituted C1-C The 60 heteroaryl group and the substituents in the substituted C6-C30 aromatic ring are each independently selected from 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, and C6-C60 aryl.

[0013] halogen

[0014] In this application, the term "halogen" refers to an atom selected from fluorine, chlorine, bromine, and iodine.

[0015] Replaced or not replaced

[0016] 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 substituent Rc mentioned above can be, for example, one or a combination of at least two of the following: deuterium, halogen, cyano, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 arylamine, and C3-C60 heteroarylamine. 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 be fused with the functional group to which they are attached to form a ring.

[0017] alkyl

[0018] 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. "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 include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl.

[0019] alkenyl

[0020] 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. "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.

[0021] acetylin

[0022] 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. "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.

[0023] C3-C60 cycloalkyl

[0024] In this application, the term "C1-C60 heterocyclic alkyl" includes one or more of O, S, Se, N, and Si as heteroatoms, and is a monocyclic or polycyclic compound having 1 to 60 carbon atoms, preferably 1 to 40 carbon atoms, and even more preferably 1 to 20 carbon atoms. Here, the polycyclic compound 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.

[0025] C3-C60 cycloalkenyl

[0026] In this application, the term "C3-C60 cycloalkenyl" refers to a cycloalkenyl group consisting of at least 3 atoms, and more specifically, 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.

[0027] C1-C60 heterocyclic alkenyl

[0028] In this application, the term "C1-C60 heterocyclic alkenyl" includes one or more of O, S, Se, N and Si as heteroatoms, and is 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.

[0029] Aryl, aryl

[0030] 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.

[0031] heteroaryl, hypoaryl

[0032] In this application, the terms "heteroaryl" and "hybridoaryl" include 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, pyrroloyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetraazinyl, triazolyl, tetraazolyl, furazolidyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiophene, isobenzofuranyl, dibenzofuranyl, dibenzothiophene, 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.

[0033] hydrogen atom

[0034] In this application, unless otherwise stated, hydrogen atoms include protium, deuterium, and tritium.

[0035] number of carbon atoms

[0036] In this application, the definition of a group specifies the range of carbon atoms, and the number of carbon atoms is any integer within the defined range, such as C6-C60 aryl. The number of carbon atoms representing an aryl group can be any integer within the range of 6-60, such as 6, 8, 10, 13, 15, 17, 20, 22, 25 or 30, etc.

[0037] In this application, if the group is not specified as substituted or unsubstituted, it means that it has not been substituted.

[0038] Preferably, the organic electroluminescent compound is selected from one of the following structures:

[0039]

[0040] Preferably, L1 and L2 are each independently selected from substituted or unsubstituted C6-C60 arylene groups, wherein the substituted or unsubstituted C6-C60 arylene groups represent substituted or unsubstituted C6-C60 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, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, or 60 carbon atoms.

[0041] Preferably, L1 and L2 are each independently selected from substituted or unsubstituted C6-C50 arylene groups; wherein the substituents in the substituted C6-C50 arylene groups are each independently selected from deuterium, halogen, cyano, hydroxyl, nitro, amido, 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, and C6-C50 aryl.

[0042] Preferably, L1 and L2 are each independently selected from substituted or unsubstituted C6-C25 arylene groups;

[0043] The substituents in the substituted C6-C25 arylene groups are independently selected from 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, and C6-C25 aryl.

[0044] Preferably, L1 and L2 are each independently selected from substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted triphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted binatylene, substituted or unsubstituted phenylenenaphthylene, substituted or unsubstituted naphthylphenylene, substituted or unsubstituted fluorene, substituted or unsubstituted phenylenefluorene, substituted or unsubstituted benzo[a]fluorene, substituted or unsubstituted dibenzo[a]fluorene, substituted or unsubstituted phenanthrene, substituted or unsubstituted phenylenephenanthrene, substituted or unsubstituted anthracene;

[0045] The substituents in the substituted groups are each independently 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, fluorenyl, dibenzofuranyl, dibenzothiophene, or carbazole.

[0046] Preferably, L1 and L2 are the same or different, and each is independently selected from phenylene, naphthyl, and biphenylene.

[0047] Preferably, L1 and L2 are the same or different, and each is independently selected from phenylene.

[0048] Preferably, R is selected from hydrogen, deuterium, halogen, cyano, hydroxyl, nitro, substituted or unsubstituted C1-C50 alkyl, substituted or unsubstituted C2-C50 alkenyl, substituted or unsubstituted C3-C50 cycloalkyl, 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, and substituted or unsubstituted C1-C50 heteroaryl.

[0049] Preferably, the substituents in the substituted C1-C50 alkyl, substituted C2-C50 alkenyl, substituted C3-C50 cycloalkyl, 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 deuterium, halogen, cyano, hydroxyl, nitro, amido, 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, and C6-C50 aryl.

[0050] Preferably, R is selected from hydrogen, deuterium, halogen, cyano, hydroxyl, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C2-C25 alkenyl, substituted or unsubstituted C3-C25 cycloalkyl, 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;

[0051] Preferably, n is selected from 0-6 and when n is greater than 1, multiple R exist independently or combine with each other to form substituted or unsubstituted C6-C30 aromatic rings;

[0052] Wherein, the substituents in the substituted C1-C25 alkyl, substituted C2-C25 alkenyl, substituted C3-C25 cycloalkyl, 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, substituted C1-C25 heteroaryl, and substituted C6-C30 aromatic rings are selected from 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, and C6-C25 aryl;

[0053] Preferably, R is selected from one or more of hydrogen, deuterium, methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, vinyl, n-propenyl, isopropenyl, n-butenyl, and sec-butene;

[0054] Preferably, n is selected from 0-6, and when n is greater than 1, multiple Rs exist independently or combine with each other to form substituted or unsubstituted C6-C30 aromatic rings; wherein the substituents in the substituted aromatic rings are selected from 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, and C6-C25 aryl.

[0055] Preferably, the aromatic ring is a benzene ring or a naphthalene ring.

[0056] Preferably, Ar1 and Ar2 are each independently selected from substituted or unsubstituted C6-C50 aryl groups and substituted or unsubstituted C1-C50 heteroaryl groups;

[0057] The substituents in the substituted C6-C50 aryl and the substituted C1-C50 heteroaryl are the same or different, and are independently selected from deuterium, halogen, cyano, hydroxyl, nitro, amido, 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, and C6-C50 aryl.

[0058] Preferably, Ar1 and Ar2 are each independently selected from substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C1-C30 heteroaryl groups; wherein the substituents in the substituted C6-C30 aryl groups and the substituted C1-C30 heteroaryl groups are each independently selected from deuterium, halogen, cyano, hydroxyl, nitro, amidine, 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, and C6-C30 aryl groups;

[0059] Preferably, Ar1 and Ar2 are each independently selected from substituted or unsubstituted C6-C25 aryl groups and substituted or unsubstituted C1-C25 heteroaryl groups;

[0060] The substituents in the substituted C6-C25 aryl and the substituted C1-C25 heteroaryl are each independently selected from 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, and C6-C25 aryl.

[0061] 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 indyl, substituted or unsubstituted tetraphenyl, substituted or unsubstituted peryl. Substituted or unsubstituted trefoilyl, substituted or unsubstituted tetraphenyl, substituted or unsubstituted fluoranyl or 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, substituted or unsubstituted tetrazolyl Substituted or unsubstituted furazolidone, 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 benzimidazolyl, 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 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 phenanthidyl, substituted or unsubstituted dipyridyl, substituted or unsubstituted terpyridyl, substituted or unsubstituted phenylterpyridyl, substituted or unsubstituted diazafluorenyl, or substituted or unsubstituted naphthoxazolyl;

[0062] 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 anthranyl, substituted indyl, substituted tetraphenyl, substituted perylene, substituted tyl, substituted tetraphenyl, substituted fluoranyl or spirodifluorenyl, substituted furanyl, substituted... 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 pyrimidinyl, substituted pyridazinyl, substituted benzofuranyl, substituted benzothiopheneyl, substituted isobenzo[] Furanyl, substituted dibenzofuranyl, substituted dibenzothiophenyl, substituted benzimidazolyl, substituted benzothiazolyl, substituted benziisothiazolyl, substituted benziisooxazolyl, 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 phenanthidinyl, substituted dipyridyl, substituted terpyridyl, substituted phenyl terpyridyl, substituted diazafluorenyl, or substituted naphthooxazolyl are each independently 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, fluorenyl, dibenzofuranyl, dibenzothiophenyl, or carbazoleyl.

[0063] Preferably, Ar1 and Ar2 are each independently selected from the following groups:

[0064]

[0065]

[0066] Preferably, the organic electroluminescent compound is selected from one of the following structures:

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081] The present invention also provides an organic electroluminescent material comprising the organic electroluminescent compound described above.

[0082] The present invention also provides an organic electroluminescent device, comprising a first electrode, an organic layer, and a second electrode stacked sequentially.

[0083] The organic layer contains the organic electroluminescent compound or the organic electroluminescent material described above.

[0084] Preferably, the organic layer includes a first light-emitting layer, which contains an organic electroluminescent compound as described above or an organic electroluminescent compound as described above.

[0085] Preferably, the organic layer includes an organic functional layer and a second light-emitting layer;

[0086] The organic functional layer comprises the organic electroluminescent compound or the organic electroluminescent material described above, and a compound comprising the following formula (2):

[0087]

[0088] In the formula, X 1 -X 14 Each is independently selected from N or CR, and R is selected from hydrogen or deuterium;

[0089] Ar 4 Ar 5Each is independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C6-C60 aromatic amino, or substituted or unsubstituted C3-C60 heteroaryl;

[0090] The substituents in the substituted C6-C30 aryl, substituted C3-C30 heteroaryl, substituted C6-C60 aromatic amino, and substituted C3-C60 heteroaryl are selected from one or a combination of two of the following: deuterium, halogen, cyano, C1-C6 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 aromatic amino, and C3-C60 heteroarylamine.

[0091] Preferably, the organic functional layer includes a first organic functional layer and a second organic functional layer;

[0092] The second organic functional layer contains the organic electroluminescent compound or the organic electroluminescent material described above, and the first organic functional layer contains the compound shown in formula (2).

[0093] Preferably, the first organic functional layer, the second organic functional layer, and the second light-emitting layer are stacked sequentially.

[0094] Preferred, X 1 -X 14 All are selected from CR, and R is selected from hydrogen or deuterium;

[0095] Preferred, X 1 -X 14 All are selected from CR, where R is selected from hydrogen;

[0096] Preferred, X 1 -X 6 One of them is selected from N, and the rest are CR;

[0097] Preferred, X 1 -X 6 One of them is selected from N, and the rest are CR, X 7 -X 14 One of them is selected from N, and the rest are CR;

[0098] In this context, each R exists independently and can be the same or different; R is defined as described above.

[0099] Preferred, Ar 4 -Ar 5 Each group is independently selected from either substituted or unsubstituted A groups;

[0100] The A group is selected from: phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, fluoranyl, triphenylene, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirodifluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirodifluorenyl, benzofuranyl, dibenzofuranyl, naphthobenzofuranyl, dinaphthofuranyl, benzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, carbazoyl, phenylcarbazoyl, benzomethylcarbazoyl, dibenzocarbazoyl, biphenylcarbazoyl, phenanthrenebenzofuranyl, dibenzofuranfuranyl or phenylcarbazobenzofuranyl;

[0101] The substituent of the substituted A group is selected from one or a combination of two of the following: deuterium, halogen, cyano, C1-C6 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 aromatic amino, and C3-C60 heteroarylamine.

[0102] Preferably, the Ar 4 -Ar 5 Each group is independently selected from phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, fluorenyl, triphenylene, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirodifluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirodifluorenyl, dibenzofuranyl, naphthobenzofuranyl, dibenzothiophenyl, naphthobenzothiophenyl, phenylcarbazoyl, benzophenylcarbazoyl, dibenzophenylcarbazoyl, or groups having the following structures:

[0103]

[0104]

[0105] Multiple Ar ’ When they exist independently, they can be the same or different;

[0106] Among them, Ar ’ Each C group is independently selected from substituted or unsubstituted C groups, wherein the C groups are selected from: phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, fluorenyl, triphenylene, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirodifluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirodifluorenyl, benzofuranyl, dibenzofuranyl, naphthobenzofuranyl, benzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, carbazoyl, phenylcarbazoyl, benzophenylcarbazoyl or dibenzophenylcarbazoyl;

[0107] The substituents of the substituted C group are selected from one or a combination of two of the following: deuterium, halogen, cyano, C1-C6 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 aromatic amino, and C3-C60 heteroarylamine.

[0108] Preferably, the structure of equation (2) is represented by any of the following structures:

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124] Preferably, the organic functional layer includes a light-emitting auxiliary layer and an electron-blocking layer stacked together, the electron-blocking layer containing an organic electroluminescent compound with the structure shown in formula (1) above, and the light-emitting auxiliary layer containing a compound with the structure shown in formula (2) above.

[0125] Preferably, the material of the second light-emitting layer comprises an organic electroluminescent host material composition, which comprises compounds having the structures of formulas (3) and (4) below:

[0126]

[0127] In the formula, ring A is a benzene ring;

[0128] Ar is selected from substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 aromatic amino, substituted or unsubstituted C3-C60 heteroaryl, and substituted or unsubstituted C3-C30 heteroaryl.

[0129] L 4 Selected from substituted or unsubstituted C6-C30 arylene groups and substituted or unsubstituted C3-C30 heteroarylene groups;

[0130] The substituents in the substituted C6-C60 aryl, substituted C6-C60 aromatic amino, substituted C3-C60 heteroaryl, substituted C3-C30 heteroaryl, substituted C6-C30 arylene, and substituted C3-C30 heteroarylene are each independently selected from one or a combination of at least two of the following: deuterium, halogen, cyano, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 aromatic amino, and C3-C60 heteroaryl.

[0131]

[0132] In the formula, X 1’ -X 14’ Each is independently selected from N or CR ’ R ’ Selected from hydrogen, deuterium, and C6-C30 aryl groups;

[0133] L 5 Independently selected from the linking bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C3-C30 heteroarylene; Ar 6 Ar 7 Each is independently selected from substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C3-C30 heteroaryl groups;

[0134] The substituents in the substituted C6-C30 arylene, substituted C3-C30 heteroarylene, substituted C6-C60 aryl, substituted C6-C60 aromatic amino, substituted C3-C60 heteroaryl, and substituted C3-C60 heteroaryl are selected from one or a combination of two of the following: deuterium, halogen, cyano, C1-C6 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, C3-C30 heteroarylene, C6-C60 aromatic amino, and C3-C60 heteroaryl.

[0135] Preferably, in the organic electroluminescent host material composition, the mass ratio of the compound having the structure of formula (3) to the compound having the structure of formula (4) is 1:9-9:1;

[0136] Preferably, in the organic electroluminescent host material composition, the mass ratio of the compound having the structure of formula (3) to the compound having the structure of formula (4) is 2:8-8:2;

[0137] Preferably, in the organic electroluminescent host material composition, the mass ratio of the compound having the structure of formula (3) to the compound having the structure of formula (4) is 3:7-7:3;

[0138] Preferably, in the organic electroluminescent host material composition, the mass ratio of the compound having the structure of formula (3) to the compound having the structure of formula (4) is 4:6-6:4.

[0139] Preferably, in the formula (3), Ar is selected from substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C6-C25 aromatic amino, substituted or unsubstituted C3-C25 heteroaryl, and substituted or unsubstituted C3-C20 heteroaryl.

[0140] The substituents in the substituted C6-C25 aryl, substituted C6-C25 aromatic amino, substituted C3-C25 heteroaryl, and substituted C3-C20 heteroaryl are each independently selected from one or a combination of at least two of the following: deuterium, halogen, cyano, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C30 aromatic amino, and C3-C30 heteroaryl.

[0141] Preferably, Ar is selected from substituted or unsubstituted D groups, and the D group is selected from the following groups: phenyl, naphthyl, biphenyl, phenanthryl, fluoranthyl, ... , terphenyl, triphenylene, finadeninyl, phenylnaphthyl, naphthylphenyl, dimethylfluorenyl, phenylmethylfluorenyl, diphenylfluorenyl, pyridyl, pyridylphenyl, phenylpyridyl, spirodifluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirodifluorenyl, dibenzofuranyl, benzonaphthiofuranyl, benzonaphthiopheneyl, spiro[fluoren-9,9'-oxazanthyl]yl, phenylmethylfluorenyl, dinaphthiofuranyl, dinaphthiopheneyl, dibenzothiopheneyl, N,N-diphenylaniline;

[0142] Wherein, the substituents of the substituted D group are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C30 aromatic amino, and C3-C30 heteroaryl.

[0143] Preferably, in formula (3), Ar is selected from phenyl, naphthyl, biphenyl, ... yl, phenanthrene, terphenyl, phenylnaphthyl, naphthylphenyl, dimethylfluorenyl, diphenylfluorenyl, spirodifluorenyl, finadenoyl, dibenzofuranyl, benzonaphthylfuranyl, N,N-diphenylaniline;

[0144] Preferably, in equation (3), L 5Selected from substituted or unsubstituted C6-C15 arylene groups; wherein each substituent in the substituted C6-C15 arylene group is independently selected from one or a combination of at least two of deuterium, halogen, and C1-C62 alkyl groups;

[0145] Preferably, L 5 Selected from phenylene, biphenylene, and naphthylene;

[0146] Preferably, L 5 Selected from phenylene and naphthylene.

[0147] Preferably, in equation (4), X 1’ -X 14’ All selected from CR ’ R ’ The definition is the same as described above;

[0148] Preferred, X 1’ -X 6’ One of them is selected from N, and the rest are CR. ’ R ’ The definition is the same as described above;

[0149] Preferred, X 1’ -X 6’ One of them is selected from N, and the rest are CR. ’ ;X 7’ -X 14’ One of them is selected from N, and the rest are CR. ’ R ’ The definition is the same as described above;

[0150] Preferably, R ’ Selected from hydrogen, deuterium, phenyl, and naphthyl;

[0151] Ar 6 Ar 7 Each is independently selected from substituted or unsubstituted C6-C18 aryl groups and substituted or unsubstituted C3-C18 heteroaryl groups;

[0152] The substituents in the substituted C6-C18 aryl and substituted C3-C18 heteroaryl are selected from one or a combination of two of the following: deuterium, halogen, cyano, C1-C6 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 aromatic amino, and C3-C60 heteroaromatic amino.

[0153] Preferred, Ar 6 Ar 7 Each group is independently selected from substituted or unsubstituted groups E;

[0154] The group E is selected from: phenyl, naphthyl, biphenyl, terphenyl, phenanthrene, fluorenyl, triphenylene, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirodifluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirodifluorenyl, benzofuranyl, dibenzofuranyl, naphthobenzofuranyl, dinaphthofuranyl, benzothiopheneyl, dibenzothiopheneyl, naphthobenzothiopheneyl, carbazolyl, phenylcarbazolyl, benzophenylcarbazolyl, dibenzophenylcarbazolyl, biphenylcarbazolyl, phenanthrenebenzofuranyl, dibenzofuranfuranyl, phenylcarbazobenzofuranyl;

[0155] Wherein, the substituent in the substituted group E is selected from one or a combination of two of the following: deuterium, halogen, cyano, C1-C6 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 aromatic amino, and C3-C60 heteroaryl.

[0156] Preferred, Ar 6 Ar 7 Each is independently selected from phenyl, naphthyl, biphenyl, terphenyl, phenanthrene, fluorenyl, triphenylene, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirodifluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirodifluorenyl, dibenzofuranyl, naphthobenzofuranyl, dibenzothiophenyl, naphthobenzothiophenyl, carbazoleyl, phenylcarbazoleyl, benzocarbazoleyl, and dibenzocarbazoleyl.

[0157] Preferably, L 5 Each is independently selected from the linking bond, substituted or unsubstituted C6-C18 arylene groups; wherein the substituents in the substituted C6-C18 arylene groups are selected from one or a combination of two of the following: deuterium, halogen, cyano, C1-C6 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 arylamine, and C3-C60 heteroarylamine.

[0158] Preferably, L 5 Selected from linking bonds and phenylene.

[0159] Preferably, formula (3) has any of the structures shown in E-1 to E-208:

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168] Preferably, in equation (4), X 1’ -X 14’ All selected from CR ’ R ’ The definitions described above;

[0169] Preferred, X 1’ -X 6’ One of them is selected from N, and the rest are CR. ’ R ’ The definitions described above;

[0170] Preferred, X 1’ -X 6’ One of them is selected from N, and the rest are CR. ’ ;X 7’ -X 14’ One of them is selected from N, and the rest are CR. ’ R ’ The definitions described above;

[0171] Preferred, R ’ Selected from hydrogen, deuterium, phenyl, and naphthyl;

[0172] Ar 6 Ar 7 Each is independently selected from substituted or unsubstituted C6-C18 aryl groups and substituted or unsubstituted C3-C18 heteroaryl groups;

[0173] The substituents in the substituted C6-C18 aryl and substituted C3-C18 heteroaryl are selected from one or a combination of two of the following: deuterium, halogen, cyano, C1-C6 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 aromatic amino, and C3-C60 heteroaromatic amino.

[0174] Preferred, Ar 6 Ar 7 Each group is independently selected from substituted or unsubstituted groups E;

[0175] The group E is selected from: phenyl, naphthyl, biphenyl, terphenyl, phenanthrene, fluorenyl, triphenylene, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirodifluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirodifluorenyl, benzofuranyl, dibenzofuranyl, naphthobenzofuranyl, dinaphthofuranyl, benzothiopheneyl, dibenzothiopheneyl, naphthobenzothiopheneyl, carbazolyl, phenylcarbazolyl, benzophenylcarbazolyl, dibenzophenylcarbazolyl, biphenylcarbazolyl, phenanthrenebenzofuranyl, dibenzofuranfuranyl, phenylcarbazobenzofuranyl;

[0176] Wherein, the substituent in the substituted group E is selected from one or a combination of two of the following: deuterium, halogen, cyano, C1-C6 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 aromatic amino, and C3-C60 heteroaryl.

[0177] Preferred, Ar 6 Ar 7 Each is independently selected from phenyl, naphthyl, biphenyl, terphenyl, phenanthrene, fluorenyl, triphenylene, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirodifluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirodifluorenyl, dibenzofuranyl, naphthobenzofuranyl, dibenzothiophenyl, naphthobenzothiophenyl, carbazoleyl, phenylcarbazoleyl, benzocarbazoleyl, and dibenzocarbazoleyl.

[0178] Preferably, L 5 Each is independently selected from the linking bond, substituted or unsubstituted C6-C18 arylene groups; wherein the substituents in the substituted C6-C18 arylene groups are selected from one or a combination of two of the following: deuterium, halogen, cyano, C1-C6 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 arylamine, and C3-C60 heteroarylamine.

[0179] Preferably, L 5 Selected from linking bonds and phenylene.

[0180] Preferably, formula (4) has any of the following structures shown in M-1 to M-723:

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196] Preferably, the organic electroluminescent device further includes:

[0197] Hole injection layer located between the first electrode and the light-emitting auxiliary layer;

[0198] A hole transport layer located between the hole injection layer and the light-emitting auxiliary layer;

[0199] An electron transport layer located between the second light-emitting layer and the second electrode;

[0200] And an electron injection layer between the electron transport layer and the second electrode.

[0201] Preferably, the first electrode is an anode.

[0202] Preferably, the second electrode is a cathode.

[0203] The present invention also provides an organic electroluminescent device, including the organic electroluminescent device described above.

[0204] In this application, the term "organic electroluminescent material" refers to a material that can be used in an organic electroluminescent device and may contain at least one compound. If desired, the organic electroluminescent material may be contained in any layer constituting the organic electroluminescent device. For example, the organic electroluminescent material may be a hole injection material, a hole transport material, a hole assist material, a light-emitting assist material, an electron blocking material, a light-emitting material (containing an organic electroluminescent host material and a dopant material), an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc.

[0205] In this application, the organic electroluminescent material disclosed herein may comprise one organic electroluminescent material or multiple organic electroluminescent materials, wherein multiple organic electroluminescent materials refer to a material comprising a combination of at least two organic electroluminescent materials, said material may be contained in any layer constituting the organic electroluminescent device. It may refer to both materials contained before the organic electroluminescent device (e.g., before vapor deposition) and materials contained after the organic electroluminescent device (e.g., after vapor deposition). For example, the material may be a combination of at least two compositions, said composition may include at least one of the following: a hole injection layer, a hole transport layer, a hole assist layer, a light-emitting assist layer, an electron blocking layer, a light-emitting layer, an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer. The two compositions in the multiple organic electroluminescent materials may be contained in the same layer or different layers, and may be mixed-evaporated or co-evaporated, or may be evaporated individually.

[0206] In this application, the term "organic electroluminescent host material composition" refers to an organic electroluminescent material comprising a combination of at least two host materials. It can refer to both materials included before (e.g., before vapor deposition) and materials included after (e.g., after vapor deposition) the organic electroluminescent device. The compositions disclosed herein can be included in any light-emitting layer constituting an organic electroluminescent device. Two or more compounds of the various host materials included in the compositions disclosed herein can be included in one light-emitting layer, or they can be included separately in different light-emitting layers. For example, when a layer contains two or more host materials, the layer can be formed by co-evaporation, or it can be formed simultaneously by individual co-evaporation.

[0207] In the material composition, the mass ratio of the first compound to the second compound is 1:9-9:1;

[0208] Preferably, in the material composition, the mass ratio of the first compound to the second compound is 2:8-8:2;

[0209] More preferably, in the material composition, the mass ratio of the first compound to the second compound is 3:7-7:3;

[0210] More preferably, in the material composition, the mass ratio of the first compound to the second compound is 4:6 to 6:4.

[0211] As used in this disclosure, anode and cathode refer to electrodes used in organic light-emitting devices.

[0212] Preferably, the first electrode is the anode. As the anode material, a material with a large work function is generally preferred, allowing holes to be smoothly injected into the organic material layer. Specific examples of anode materials include: metals, such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides, such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides, such as ZnO:Al or SnO2:Sb; conductive polymers, such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxo)thiophene] (PEDOT), polypyrrole, and polyaniline; and so on, but are not limited thereto.

[0213] Preferably, the second electrode is a cathode. As the cathode material, a material with a small work function is generally preferred, allowing electrons to be easily injected into the organic material layer. Specific examples of cathode materials include: metals, such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer materials, such as LiF / Al or LiO2 / Al; and so on, but are not limited thereto.

[0214] Preferably, the hole injection layer is a layer that injects holes from the electrode, and the hole injection material is preferably a compound that has the ability to transport holes, has the effect of injecting holes into the anode, and has an excellent hole injection effect on the light-emitting layer or light-emitting material, prevents excitons generated in the light-emitting layer from moving to the electron injection layer or electron injection material, and is excellent in terms of thin film formation ability. Furthermore, it is preferred that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include, but are not limited to, metalloporphyrins, oligothiophenes, arylamine-based organic materials, hexanitrile hexaazabenzophenanthrene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinones, polyaniline, and polythiophene-based conductive polymers. The material of the hole injection layer may, for example, be selected from the following compounds or any combination thereof:

[0215]

[0216] Preferably, 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 hole transport material is suitably a material with a high hole mobility that can receive hole injections from the anode or hole injection layer and transfer the holes to the light-emitting layer. Specific examples of hole transport materials include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers containing both conjugated and non-conjugated portions. The material of the hole transport layer 4 can be selected, for example, from the following compounds or any combination thereof:

[0217]

[0218] Preferably, the light-emitting auxiliary layer increases the recombination probability of holes and electrons by enhancing the hole injection and electron blocking characteristics that block electrons injected from the cathode, and improves the luminous efficiency by confining the excitons generated within the light-emitting layer.

[0219] Preferably, the electron blocking layer refers to 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.

[0220] Preferably, the light-emitting layer is a layer that emits light in the visible light region by combining holes and electrons transported from the anode and cathode. Typically, the light-emitting layer comprises a host material and a dopant material, and in this disclosure, it comprises one or more compounds represented by Chemical Formula 3 and one or more compounds represented by Chemical Formula 4 as the host material. The type of dopant material can be either a fluorescent material or a phosphorescent material. The amount of dopant material used is preferably 0.1–70% by mass, more preferably 0.1–30% by mass, further preferably 1–30% by mass, even more preferably 1–20% by mass, and particularly preferably 1–10% by mass.

[0221] Preferably, the fluorescent dopant material used in the luminescent layer of this application may include, but is not limited to, fused polycyclic aromatic derivatives, styrene-based amine derivatives, fused cyclic amine derivatives, boron-containing compounds, pyrrole derivatives, indole derivatives, carbazole derivatives, etc.

[0222] Preferably, the phosphorescent doping material used in this application may include, but is not limited to, heavy metal complexes, phosphorescent rare earth metal complexes, etc. Examples of heavy metal complexes include iridium complexes, platinum complexes, osmium complexes, etc.; examples of rare earth metal complexes include terbium complexes, europium complexes, etc., but are not limited to these.

[0223] Preferably, the hole blocking layer is 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 recombine in the light-emitting layer; it can also be called a hole suppression layer or a hole blocking layer. The hole blocking layer is preferably made of a material with high ionization energy.

[0224] Preferably, the electron transport layer is a layer that receives electrons from the cathode or an electron injection layer formed on the cathode and transports the electrons to the light-emitting layer and suppresses the transfer of holes from the light-emitting layer, and the electron transport material is suitably a material that can well receive the injection of electrons from the cathode and transfer the electrons to the light-emitting layer, and has a large electron mobility.

[0225] Specific examples of electron transport materials include, but are not limited to, Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic radical compounds, hydroxyflavonoid-metal complexes, etc. The electron transport layer can be used with any desired cathode material, as used according to conventional techniques. In particular, suitable examples of cathode materials are typically materials with a small work function, followed by an aluminum or silver layer. Specific examples include cesium, barium, calcium, ytterbium, and samarium, each followed by an aluminum or silver layer.

[0226] Preferably, the electron injection layer is a layer that injects electrons from the electrode, and preferably is a compound that has the ability to transport electrons, has the effect of injecting electrons from the cathode and has an excellent effect of injecting electrons into the light-emitting layer or light-emitting material, prevents excitons generated by the light-emitting layer from moving to the hole injection layer, and is also excellent in terms of the ability to form a thin film.

[0227] Specific examples of electron-injected layers include fluorenones, anthraquinone dimethanes, biphenylquinones, thiamethane dioxides, azoles, diazoles, triazoles, imidazoles, perylenetetracarboxylic acids, fluorenemethane, anthrones, and their derivatives; metal complex compounds; nitrogen-containing 5-membered ring derivatives; and so on, but are not limited to these.

[0228] Examples of metal complex compounds include, but are not limited to, lithium 8-hydroxyquinoline, bis(8-hydroxyquinoline)zinc, bis(8-hydroxyquinoline)copper, bis(8-hydroxyquinoline)manganese, tris(8-hydroxyquinoline)aluminum, tris(2-methyl-8-hydroxyquinoline)aluminum, tris(8-hydroxyquinoline)gallium, bis(10-hydroxybenzo[h]quinoline)beryllium, bis(10-hydroxybenzo[h]quinoline)zinc, bis(2-methyl-8-quinoline)chlorogallium, bis(2-methyl-8-quinoline)(o-cresol)gallium, bis(2-methyl-8-quinoline)(1-naphthol)aluminum, and bis(2-methyl-8-quinoline)(2-naphthol)gallium.

[0229] On the other hand, in this disclosure, the “electron injection and transport layer” is a layer that serves as both an electron injection layer and an electron transport layer, and the materials that serve the functions of each layer can be used individually or stacked and combined, but are not limited thereto.

[0230] It should be noted that, in this application, the compound shown in formula (1) is prepared via the following synthetic route, including the following steps:

[0231] 1. General formula for the synthesis of intermediate M

[0232]

[0233] 2. Compound Formula (1) General Synthetic Formula

[0234]

[0235] The compound shown in formula (3) can be prepared by the following synthetic route, including the following steps:

[0236] 1. Synthesis of intermediate En-A: The reactants En-1 and En-2 undergo a Suzuki cross-coupling reaction, as shown in the following equation:

[0237]

[0238] 2. Synthesis of compound En: Intermediate En-A and En-B undergo a Buchwald-Hartwig cross-coupling reaction, as shown in the following equation:

[0239]

[0240] The above implementation methods can be freely combined.

[0241] The beneficial effects of this invention are:

[0242] The organic electroluminescent compound provided by the present invention is based on the core in the structure of formula (1). By limiting the selectable 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

[0243] 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.

[0244] Figure 1 This is a structural diagram of the organic electroluminescent device in the device embodiment of the present invention;

[0245] Wherein: 1-substrate, 2-anode, 3-hole injection layer, 4-hole transport layer, 5-light-emitting auxiliary layer, 6-electron blocking layer, 7-light-emitting layer, 8-electron transport layer, 9-electron injection layer, 10-cathode. Detailed Implementation

[0246] In the following sections, embodiments of the present disclosure will be described in more detail to facilitate an understanding of the invention.

[0247] The above implementation methods can be freely combined, and detailed descriptions are provided below with reference to specific embodiments.

[0248] Synthesis Examples

[0249] 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.

[0250] 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.

[0251] Preparation of intermediates

[0252] Synthesis of intermediate M1

[0253]

[0254] Take a 100 mL three-necked round-bottom flask, add a stir bar and a reflux tube, and under nitrogen protection, add the following ingredients in sequence: sub-a1 (1.2 mmol), 4-bromoaniline (1.0 mmol), Pd(dppf)Cl2 (0.03 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL). Heat to 90 °C and react for 5 h. After the reaction is complete, cool to room temperature, quench with saturated ammonium chloride aqueous solution, extract with ethyl acetate, dry the organic phase with anhydrous magnesium sulfate, remove the solvent using a rotary evaporator, and separate the crude product by column chromatography (ethyl acetate: n-hexane = 1:50) to obtain intermediate A1 (yield 88%).

[0255] Take a 100 mL three-necked round-bottom flask, add a stir bar and a reflux tube, and under nitrogen protection, add the following ingredients sequentially: sub-Cl (1.0 mmol), 4-bromophenylboronic acid (1.2 mmol), Pd(dppf)Cl2 (0.03 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL). Heat to 90 °C and react for 5 h. After the reaction is complete, cool to room temperature, quench with saturated ammonium chloride aqueous solution, extract with ethyl acetate, dry the organic phase with anhydrous magnesium sulfate, remove the solvent using a rotary evaporator, and separate the crude product by column chromatography (ethyl acetate: n-hexane = 1:50) to obtain intermediate B1 (yield 84%).

[0256] Take a 100 mL three-necked round-bottom flask, add a stir bar and a reflux tube, and under nitrogen protection, add intermediate A1 (1 mmol), B1 (1.05 mmol), tris(dibenzylacetone)palladium (0.03 mmol), Xphos (0.05 mmol), potassium tert-butoxide (2.5 mmol), and toluene (10 mL) in sequence. Heat to 110 °C and react for 5 h. After the reaction is completed, cool to room temperature, quench with saturated ammonium chloride aqueous solution, extract with ethyl acetate, dry the organic phase with anhydrous magnesium sulfate, remove the solvent using a rotary evaporator, and separate the crude product by column chromatography (ethyl acetate: n-hexane = 3:50) to obtain intermediate M1 (yield 82%).

[0257] Following the synthesis method above, a series of intermediates M can be synthesized by simply changing the corresponding starting materials, as shown in Table 1 below.

[0258] Table 1

[0259]

[0260]

[0261] Synthesis Example 1

[0262] This synthetic example provides an organic electroluminescent compound B-1, the synthetic steps of which are shown below:

[0263]

[0264] A 100 mL three-necked round-bottom flask was fitted with a stir bar and a reflux tube. Under nitrogen protection, intermediate M1 (1 mmol), bromobenzene (1.1 mmol), tris(dibenzylacetone)palladium (0.03 mmol), Sphos (0.05 mmol), potassium tert-butoxide (2.5 mmol), and toluene (10 mL) were added sequentially. The mixture was heated to 110 °C and reacted for 5 h. After the reaction was complete, the mixture was cooled to room temperature, filtered, and the filter cake was washed twice with deionized water and twice with ethanol. The crude product was then purified twice by recrystallization from toluene and tetrahydrofuran, respectively, to give compound B-1 (65% yield). Elemental analysis: C 43 H 28 N₂O₂; Theoretical values: C, 85.41; H, 4.67; N, 4.63; O, 5.29; Measured values: C, 85.44; H, 4.65; N, 4.62; HRMS(ESI) m / z [M+H] + Theoretical value: 604.22; Measured value: 605.20.

[0265] Synthesis Example 2

[0266] This synthetic example provides an organic electroluminescent compound B-39, the synthetic steps of which are shown below:

[0267]

[0268] Take a 100 mL three-necked round-bottom flask and place a stir bar and a reflux tube on top. Under nitrogen protection, add intermediate M1 (1 mmol), 3-bromo-9,9'-spirodifluorene (1.1 mmol), tris(dibenzylacetone)palladium (0.03 mmol), Sphos (0.05 mmol), potassium tert-butoxide (2.5 mmol), and toluene (10 mL) in sequence. Heat to 110 °C and react for 5 h. After the reaction is completed, cool to room temperature, filter, wash the filter cake twice with deionized water, wash twice with ethanol, and then recrystallize the crude product twice with toluene and tetrahydrofuran, respectively, to obtain compound B-39 (yield 61%).

[0269] Elemental analysis: C 62 H 38 N₂O₂; Theoretical values: C, 88.34; H, 4.54; N, 3.32; O, 3.80; Measured values: C, 88.31; H, 4.55; N, 3.34; HRMS(ESI) m / z [M+H] + Theoretical value: 842.29; Measured value: 843.27.

[0270] Synthesis Example 3

[0271] This synthetic example provides an organic electroluminescent compound B-45, the synthetic steps of which are shown below:

[0272]

[0273] Take a 100 mL three-necked round-bottom flask and place a stir bar and a reflux tube on top. Under nitrogen protection, add intermediate M1 (1 mmol), 2'-bromospiro[cyclohexane-1,9'-fluorene] (1.1 mmol), tris(dibenzylacetone)palladium (0.03 mmol), Sphos (0.05 mmol), potassium tert-butoxide (2.5 mmol), and toluene (10 mL) in sequence. Heat to 110 °C and react for 5 h. After the reaction is complete, cool to room temperature, filter, wash the filter cake twice with deionized water, wash twice with ethanol, and then recrystallize the crude product twice with toluene and tetrahydrofuran, respectively, to obtain compound B-45 (yield 70%).

[0274] Elemental analysis: C 55 H 40 N₂O₂; Theoretical values: C, 86.81; H, 5.30; N, 3.68; O, 4.21; Measured values: C, 86.78; H, 5.31; N, 3.70; HRMS(ESI) m / z [M+H] + Theoretical value: 760.31; Measured value: 761.35.

[0275] Synthesis Example 4

[0276] This synthetic example provides an organic electroluminescent compound B-53, the synthesis steps of which are shown below:

[0277]

[0278] Take a 100 mL three-necked round-bottom flask and place a stir bar and a reflux tube on top. Under nitrogen protection, add intermediate M1 (1 mmol), 5-bromo-2-phenylnaphtho[2,3-d]oxazole (1.1 mmol), tris(dibenzylacetone)palladium (0.03 mmol), Sphos (0.05 mmol), potassium tert-butoxide (2.5 mmol), and toluene (10 mL) in sequence. Heat to 110 °C and react for 5 h. After the reaction is completed, cool to room temperature, filter, wash the filter cake twice with deionized water, wash twice with ethanol, and then recrystallize the crude product twice with toluene and tetrahydrofuran, respectively, to obtain compound B-53 (yield 68%).

[0279] Elemental analysis: C 54 H 33 N₃O₃; Theoretical values: C, 84.03; H, 4.31; N, 5.44; O, 6.22; Measured values: C, 84.06; H, 4.30; N, 5.42; HRMS(ESI) m / z [M+H] + Theoretical value: 771.25; Measured value: 772.28.

[0280] Synthesis Example 5

[0281] This synthetic example provides an organic electroluminescent compound B-54, the synthetic steps of which are shown below:

[0282]

[0283] Take a 100 mL three-necked round-bottom flask and place a stir bar and a reflux tube on top. Under nitrogen protection, add intermediate M54 (1 mmol), 1-chloro-terphenyl (1.1 mmol), tris(dibenzylacetone)palladium (0.03 mmol), Sphos (0.05 mmol), potassium tert-butoxide (2.5 mmol), and toluene (10 mL) in sequence. Heat to 110 °C and react for 5 h. After the reaction is completed, cool to room temperature, filter, wash the filter cake twice with deionized water, wash twice with ethanol, and then recrystallize the crude product twice with toluene and tetrahydrofuran, respectively, to obtain compound B-54 (yield 65%).

[0284] Elemental analysis: C 55 H 36 N₂O₂; Theoretical values: C, 87.28; H, 4.79; N, 3.70; O, 4.23; Measured values: C, 87.25; H, 4.80; N, 3.72; HRMS(ESI) m / z [M+H] + Theoretical value: 756.28; Measured value: 757.25.

[0285] Synthesis Example 6

[0286] This synthetic example provides an organic electroluminescent compound B-59, the synthetic steps of which are shown below:

[0287]

[0288] Take a 100 mL three-necked round-bottom flask, add a stir bar and a reflux tube, and under nitrogen protection, add intermediate M59 (1 mmol), 2-(4-chlorophenyl)naphthalene (1.1 mmol), tris(dibenzylacetone)palladium (0.03 mmol), Sphos (0.05 mmol), potassium tert-butoxide (2.5 mmol), and toluene (10 mL) in sequence. Heat to 110 °C and react for 5 h. After the reaction is complete, cool to room temperature, filter, wash the filter cake twice with deionized water, wash twice with ethanol, and then recrystallize the crude product twice with toluene and tetrahydrofuran, respectively, to obtain compound B-59 (yield 67%).

[0289] Elemental analysis: C 53 H 34N₂O₂; Theoretical values: C, 87.10; H, 4.69; N, 3.83; O, 4.38; Measured values: C, 87.13; H, 4.68; N, 3.81; HRMS(ESI) m / z [M+H] + Theoretical value: 730.26; Measured value: 731.28.

[0290] Synthesis Example 7

[0291] This synthetic example provides an organic electroluminescent compound B-64, the synthetic steps of which are shown below:

[0292]

[0293] Take a 100 mL three-necked round-bottom flask and place a stir bar and a reflux tube on top. Under nitrogen protection, add intermediate M54 (1 mmol), 2-(4-chlorophenyl)naphthalene (1.1 mmol), tris(dibenzylacetone)palladium (0.03 mmol), Sphos (0.05 mmol), potassium tert-butoxide (2.5 mmol), and toluene (10 mL) in sequence. Heat to 110 °C and react for 5 h. After the reaction is completed, cool to room temperature, filter, wash the filter cake twice with deionized water, wash twice with ethanol, and then recrystallize the crude product twice with toluene and tetrahydrofuran, respectively, to obtain compound B-64 (yield 67%).

[0294] Elemental analysis: C 53 H 34 N₂O₂; Theoretical values: C, 87.10; H, 4.69; N, 3.83; O, 4.38; Measured values: C, 87.13; H, 4.68; N, 3.81; HRMS(ESI) m / z [M+H] + Theoretical value: 730.26; Measured value: 731.28.

[0295] Synthesis Example 8

[0296] This synthetic example provides an organic electroluminescent compound B-117, the synthetic steps of which are shown below:

[0297]

[0298] Take a 100 mL three-necked round-bottom flask and place a stir bar and a reflux tube on top. Under nitrogen protection, add intermediate M117 (1 mmol), 5-bromo-9,9-dimethyl-2-phenyl-9H-fluorene (1.1 mmol), tris(dibenzylideneacetone)palladium (0.03 mmol), Sphos (0.05 mmol), potassium tert-butoxide (2.5 mmol), and toluene (10 mL) in sequence. Heat to 110 °C and react for 5 h. After the reaction is completed, cool to room temperature, filter, wash the filter cake twice with deionized water, and wash twice with ethanol. The crude product is then purified twice by recrystallization from toluene and tetrahydrofuran, respectively, to obtain compound B-117 (yield 63%).

[0299] Elemental analysis: C 58 H 40 N₂O₂; Theoretical values: C, 87.41; H, 5.06; N, 3.52; O, 4.01; Measured values: C, 87.44; H, 5.05; N, 3.50; HRMS(ESI) m / z [M+H] + Theoretical value: 796.31; Measured value: 797.35.

[0300] Synthesis Example 9

[0301] This synthetic example provides an organic electroluminescent compound B-140, the synthetic steps of which are shown below:

[0302]

[0303] Take a 100 mL three-necked round-bottom flask and place a stir bar and a reflux tube on top. Under nitrogen protection, add intermediate M141 (1 mmol), bromobenzene (1.1 mmol), tris(dibenzylacetone)palladium (0.03 mmol), Sphos (0.05 mmol), potassium tert-butoxide (2.5 mmol), and toluene (10 mL) in sequence. Heat to 110 °C and react for 5 h. After the reaction is completed, cool to room temperature, filter, wash the filter cake twice with deionized water, and wash twice with ethanol. The crude product is then purified twice by recrystallization from toluene and tetrahydrofuran, respectively, to obtain compound B-140 (yield 67%).

[0304] Elemental analysis: C 43 H 28 N₂O₂; Theoretical values: C, 85.41; H, 4.67; N, 4.63; O, 5.29; Measured values: C, 85.44; H, 4.65; N, 4.62; HRMS(ESI) m / z [M+H] + Theoretical value: 604.22; Measured value: 605.20.

[0305] Synthesis Example 10

[0306] This synthetic example provides an organic electroluminescent compound B-152, the synthetic steps of which are shown below:

[0307]

[0308] Take a 100 mL three-necked round-bottom flask, add a stir bar and a reflux tube, and under nitrogen protection, add intermediate M152 (1 mmol), 2-chloro-6-phenylnaphthalene (1.1 mmol), tris(dibenzylacetone)palladium (0.03 mmol), Sphos (0.05 mmol), potassium tert-butoxide (2.5 mmol), and toluene (10 mL) in sequence. Heat to 110 °C and react for 5 h. After the reaction is complete, cool to room temperature, filter, wash the filter cake twice with deionized water, wash twice with ethanol, and then recrystallize the crude product twice with toluene and tetrahydrofuran, respectively, to obtain compound B-152 (yield 61%).

[0309] Elemental analysis: C 53 H 34 N₂O₂; Theoretical values: C, 87.10; H, 4.69; N, 3.83; O, 4.38; Measured values: C, 87.13; H, 4.68; N, 3.81; HRMS(ESI) m / z [M+H] + Theoretical value: 730.26; Measured value: 731.28.

[0310] Synthesis Example 11

[0311] This synthetic example provides an organic electroluminescent compound B-158, the synthesis steps of which are shown below:

[0312]

[0313] Take a 100 mL three-necked round-bottom flask and place a stir bar and a reflux tube on top. Under nitrogen protection, add intermediate M152 (1 mmol), 1-chloro-4-phenylnaphthalene (1.1 mmol), tris(dibenzylacetone)palladium (0.03 mmol), Sphos (0.05 mmol), potassium tert-butoxide (2.5 mmol), and toluene (10 mL) in sequence. Heat to 110 °C and react for 5 h. After the reaction is completed, cool to room temperature, filter, wash the filter cake twice with deionized water, wash twice with ethanol, and then recrystallize the crude product twice with toluene and tetrahydrofuran, respectively, to obtain compound B-158 (yield 66%).

[0314] Elemental analysis: C 53 H 34 N₂O₂; Theoretical values: C, 87.10; H, 4.69; N, 3.83; O, 4.38; Measured values: C, 87.13; H, 4.68; N, 3.81; HRMS(ESI) m / z [M+H]+ Theoretical value: 730.26; Measured value: 731.28.

[0315] Synthesis Example 12

[0316] This synthetic example provides an organic electroluminescent compound B-208, the synthesis steps of which are shown below:

[0317]

[0318] Take a 100 mL three-necked round-bottom flask, add a stir bar and a reflux tube, and under nitrogen protection, add intermediate M208 (1 mmol), 2-chloro-7-phenylnaphthalene (1.1 mmol), tris(dibenzylacetone)palladium (0.03 mmol), Sphos (0.05 mmol), potassium tert-butoxide (2.5 mmol), and toluene (10 mL) in sequence. Heat to 110 °C and react for 5 h. After the reaction is complete, cool to room temperature, filter, wash the filter cake twice with deionized water, wash twice with ethanol, and then recrystallize the crude product twice with toluene and tetrahydrofuran, respectively, to obtain compound B-208 (yield 72%).

[0319] Elemental analysis: C 53 H 34 N₂O₂; Theoretical values: C, 87.10; H, 4.69; N, 3.83; O, 4.38; Measured values: C, 87.13; H, 4.68; N, 3.81; HRMS(ESI) m / z [M+H] + Theoretical value: 730.26; Measured value: 731.28.

[0320] Synthesis Example 13

[0321] This synthetic example provides an organic electroluminescent compound B-211, the synthesis steps of which are shown below:

[0322]

[0323] Take a 100 mL three-necked round-bottom flask, add a stir bar and a reflux tube, and under nitrogen protection, add intermediate M211 (1 mmol), 1-chloro-4-phenylnaphthalene (1.1 mmol), tris(dibenzylacetone)palladium (0.03 mmol), Sphos (0.05 mmol), potassium tert-butoxide (2.5 mmol), and toluene (10 mL) in sequence. Heat to 110 °C and react for 5 h. After the reaction is complete, cool to room temperature, filter, wash the filter cake twice with deionized water, wash twice with ethanol, and then recrystallize the crude product twice with toluene and tetrahydrofuran, respectively, to obtain compound B-211 (yield 69%).

[0324] Elemental analysis: C 53 H34 N₂O₂; Theoretical values: C, 87.10; H, 4.69; N, 3.83; O, 4.38; Measured values: C, 87.13; H, 4.68; N, 3.81; HRMS(ESI) m / z [M+H] + Theoretical value: 730.26; Measured value: 731.28.

[0325] Synthesis Example 14

[0326] This synthetic example provides an organic electroluminescent compound B-243, the synthesis steps of which are shown below:

[0327]

[0328] Take a 100 mL three-necked round-bottom flask, add a stir bar and a reflux tube, and under nitrogen protection, add intermediate M243 (1 mmol), 8-bromo-2-phenylnaphtho[2,3-d]oxazole (1.1 mmol), tris(dibenzylacetone)palladium (0.03 mmol), Sphos (0.05 mmol), potassium tert-butoxide (2.5 mmol), and toluene (10 mL) in sequence. Heat to 110 °C and react for 5 h. After the reaction is complete, cool to room temperature, filter, wash the filter cake twice with deionized water, wash twice with ethanol, and then recrystallize the crude product twice with toluene and tetrahydrofuran, respectively, to obtain compound B-243 (yield 74%).

[0329] Elemental analysis: C 54 H 33 N₃O₃; Theoretical values: C, 84.03; H, 4.31; N, 5.44; O, 6.22; Measured values: C, 84.06; H, 4.30; N, 5.42; HRMS(ESI) m / z [M+H] + Theoretical value: 771.25; Measured value: 772.28.

[0330] Synthesis Examples 15-18

[0331] Synthesis Examples 15-18 provide synthesis examples of compounds B-249, B-265, and B-297.

[0332] The synthesis steps are largely the same as those in Synthesis Example 1, except that the corresponding intermediates are replaced, as shown in Table 1. The general synthesis formulas are as follows:

[0333]

[0334] Compound B-249 was obtained in 78% yield. Elemental analysis: C47H30N2O2; Theoretical values: C, 86.22; H, 4.62; N, 4.28; O, 4.89; Found values: C, 86.25; H, 4.61; N, 4.26; HRMS (ESI) m / z [M+H] + Theoretical value: 654.23; Measured value: 655.26.

[0335]

[0336] Compound B-265 was obtained in 74% yield. Elemental analysis: C61H38N2O2; Theoretical values: C, 88.17; H, 4.61; N, 3.37; O, 3.85; Found values: C, 88.19; H, 4.60; N, 3.35; HRMS (ESI) m / z [M+H] + Theoretical value: 831.30; Measured value: 832.35.

[0337]

[0338] Compound B-297 was obtained in 80% yield. Elemental analysis: C59H38N2O2; Theoretical values: C, 87.82; H, 4.75; N, 3.47; O, 3.97; Found values: C, 87.85; H, 4.73; N, 3.46; HRMS (ESI) m / z [M+H] + Theoretical value: 806.29; Measured value: 807.34.

[0339] Synthesis Example 16

[0340] This embodiment provides a method for preparing compound N-531, including the following steps:

[0341]

[0342] After purging the three-necked reaction flask with a mechanical stirrer, thermometer, and condenser with nitrogen, intermediate N531-B (10 mmol), intermediate N531-A (11 mmol), and 100 ml of toluene were added sequentially. The mixture was heated under reflux to remove water for 0.5 h, cooled to 70–80 °C, and sodium tert-butoxide (15 mmol), Pd2(dba)3 (0.05 mmol), and s-phos (0.1 mmol) were slowly added. After the system stabilized, the mixture was heated to 100–110 °C and reacted for 3 h. Cool to 25–30°C, add 100 ml of water and 100 ml of toluene, stir and separate. Extract the aqueous phase once with 100 ml of toluene, separate the phases, combine the organic phases, add 7 g of anhydrous sodium sulfate to the organic phase, stir and dry, filter, concentrate the organic phase (-0.08–0.09 MPa, 55–60°C) until no liquid flows out, stir and add 20 ml of petroleum ether, cool to 0–5°C, filter, to obtain compound N-531, yield 78%.

[0343] Elemental analysis: C 44 H 31 Theoretical N values: C, 92.11; H, 5.45; N, 2.44; Measured values: C, 92.10; H, 5.45; N, 2.42 HRMS(ESI) m / z(M+): Theoretical value 573.25, measured value 574.16.

[0344] Synthesis Example 17

[0345] This embodiment provides a method for preparing compound N-532, including the following steps:

[0346]

[0347] After purging the three-necked reaction flask with a mechanical stirrer, thermometer, and condenser with nitrogen, intermediate 532-B (10 mmol), intermediate 532-A (11 mmol), and 100 ml of toluene were added sequentially. The mixture was heated under reflux to remove water for 0.5 h, cooled to 70–80 °C, and sodium tert-butoxide (15 mmol), Pd2(dba)3 (0.05 mmol), and s-phos (0.1 mmol) were slowly added. After the system stabilized, the mixture was heated to 100–110 °C and reacted for 3 h. Cool to 25–30°C, add 100 ml of water and 100 ml of toluene, stir and separate. Extract the aqueous phase once with 100 ml of toluene, separate the layers, combine the organic phases, add 7 g of anhydrous sodium sulfate to the organic phase, stir and dry, filter, concentrate the organic phase (-0.08–0.09 MPa, 55–60°C) until no liquid flows out, stir and add 40 ml of n-hexane, incubate at room temperature (20–25°C), filter, to give compound N-532, yield 71%. m / z = 587.1 [M+H] + .

[0348] Elemental analysis: C44 H 30 Theoretical N2 values: C, 90.07; H, 5.15; N, 4.77; Measured values: C, 90.10; H, 5.12; N, 4.75 HRMS(ESI) m / z(M+): Theoretical value 586.24, measured value 587.10.

[0349] Synthesis Example 18

[0350] This embodiment provides a method for preparing compound N-533, including the following steps:

[0351]

[0352] After purging the three-necked reaction flask with a mechanical stirrer, thermometer, and condenser with nitrogen, intermediate N533-B (10 mmol), intermediate N533-A (11 mmol), and 100 ml of toluene were added sequentially. The mixture was heated under reflux to remove water for 0.5 h, cooled to 70–80 °C, and sodium tert-butoxide (15 mmol), Pd2(dba)3 (0.05 mmol), and s-phos (0.1 mmol) were slowly added. After the system stabilized, the mixture was heated to 100–110 °C and reacted for 3 h. Cool to 25–30°C, add 100 ml of water and 100 ml of toluene, stir and separate the liquid. Extract the aqueous phase once with 100 ml of toluene, separate the liquid and combine the organic phases. Add 7 g of anhydrous sodium sulfate to the organic phase, stir and dry, filter, concentrate the organic phase (-0.08–0.09 MPa, 55–60°C) until no liquid flows out, stir and add 40 ml of n-hexane, incubate at room temperature (20–25°C), filter, and obtain compound N-533, yield 73%.

[0353] Elemental analysis: C 42 H 29 Theoretical values ​​for N: C, 92.11; H, 5.34; N, 2.56; Measured values: C, 92.10; H, 5.35; N, 2.55. HRMS (ESI) m / z (M+): Theoretical value 547.23, Measured value 548.21.

[0354] Synthesis Example 19

[0355] This embodiment provides a method for preparing compound N-534, including the following steps:

[0356]

[0357] After purging the three-necked reaction flask with nitrogen, which is equipped with a mechanical stirrer, thermometer, and condenser, intermediate N534-B (10 mmol), intermediate N534-A (11 mmol), and 100 ml of toluene were added sequentially. The mixture was heated under reflux to remove water for 0.5 h, cooled to 70–80 °C, and sodium tert-butoxide (15 mmol), Pd2(dba)3 (0.05 mmol), and s-phos (0.1 mmol) were slowly added. After the system stabilized, the mixture was heated to 100–110 °C and reacted for 3 h. Cool to 25–30°C, add 100 ml of water and 100 ml of toluene, stir and separate the liquid. Extract the aqueous phase once with 100 ml of toluene, separate the liquid and combine the organic phases. Add 7 g of anhydrous sodium sulfate to the organic phase, stir and dry, filter, concentrate the organic phase (-0.08–0.09 MPa, 55–60°C) until no liquid flows out, stir and add 40 ml of n-hexane, incubate at room temperature (20–25°C), filter, and obtain compound N-534, yield 58%.

[0358] Elemental analysis: C 42 H 29 Theoretical NO values: C, 89.49; H, 5.19; N, 2.48; O, 2.84; Measured values: C, 89.47; H, 5.18; N, 2.51; HRMS(ESI) m / z(M+): Theoretical value 563.22, measured value 564.21.

[0359] The synthesis conditions of the compounds in the following examples are the same as those of N-531 or N-532, except that the starting materials N-nA and N-nB, as well as the structure and yield of the products, are different, as shown in Table 2 below; the elemental analysis results of the prepared compounds are shown in Table 3.

[0360] Table 2

[0361]

[0362]

[0363]

[0364] Table 3

[0365]

[0366] Synthesis Example 32

[0367] This embodiment provides a method for preparing compound E-1, including the following steps:

[0368] Synthesis of intermediate E1-A

[0369] After purging the three-necked reaction flask with nitrogen, which was equipped with a mechanical stirrer, thermometer, and condenser, 10 g of raw material E1-1 (36.63 mmol), 5.72 g of E1-2 (36.63 mmol), 0.85 g of tetraphenylphosphine palladium (0.73 mmol), 10.11 g of potassium carbonate (73.27 mmol), 70 mL of toluene, 30 mL of ethanol, and 30 mL of water were added sequentially. The mixture was stirred at 65 °C for 2 h. After the reaction was complete, the organic layer was extracted with ethyl acetate (EA), and residual water was removed by using anhydrous sodium sulfate. The residue was dried and purified by column chromatography to obtain 10.06 g of compound E1-A (90% yield).

[0370] Synthesis of intermediate E1-B

[0371] After purging the three-necked reaction flask with nitrogen, which was equipped with a mechanical stirrer, thermometer, and condenser, 10 g of intermediate E1-A (32.78 mmol), 3.1 g of E1-3 (32.78 mmol), 0.6 g of tris(dibenzylacetone)dipalladium (0.66 mmol), 0.67 g of 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (1.64 mmol), 6.3 g of sodium tert-butoxide (65.56 mmol), and 100 mL of toluene were added sequentially. The mixture was then refluxed and stirred at 110 °C for 3 h. After the reaction was complete, the organic layer was extracted with ethyl acetate (EA), and residual water was removed by using anhydrous sodium sulfate. The residue was dried and purified by column chromatography to obtain 8.31 g of compound E1-B (yield 82%).

[0372] Synthesis of compound E-1

[0373] After purging the three-necked reaction flask with nitrogen, which was equipped with a mechanical stirrer, thermometer, and condenser, the following intermediates were added sequentially: 8.30 g E1-B (26.85 mmol), 7.95 g E1-4 (26.85 mmol), 0.49 g tris(dibenzylacetone)dipalladium (0.54 mmol), 0.55 g 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (1.34 mmol), 5.16 g sodium tert-butoxide (53.70 mmol), and 100 mL toluene. The mixture was then refluxed and stirred at 110 °C for 3 h. After the reaction was complete, the organic layer was extracted with ethyl acetate (EA), and residual water was removed by using anhydrous sodium sulfate. The residue was dried and purified by column chromatography to obtain 11.80 g of oxazole organic compound E-1 containing benzonaphthofuran (76% yield).

[0374] Elemental analysis: C 41 H 26N2O2; Theoretical values: C, 85.10; H, 4.53; N, 4.84; O, 5.53; Measured values: C, 85.12; H, 4.52; N, 4.83; HRMS(ESI) m / z [M+H]+: Theoretical value: 578.20; Measured value: 579.21.

[0375] Synthesis Example 33

[0376] This embodiment provides a method for preparing compound M-17, including the following steps:

[0377]

[0378] A 50 mL double-necked round-bottom flask was placed with a stir bar and a reflux tube attached. After drying, nitrogen gas was introduced. Compounds M17-A (19.8 mmol, CAS: 1884145-03-2), M17-B (20.75 mmol, CAS: 1883265-32-4), tetraphenylphosphine palladium (0.396 mmol), potassium carbonate (39.6 mmol), 35 mL of toluene, 15 mL of ethanol, and 15 mL of distilled water were added. The mixture was stirred at 90 °C for 8 h. After the reaction was complete, the mixture was added dropwise to methanol, and the resulting solid was filtered. The solid was purified by column chromatography to give compound M-17 (8.5 g, yield: 75%).

[0379] Elemental analysis: C 41 H 25 N3O; Theoretical values: C, 85.54; H, 4.38; N, 7.30; O, 2.78; Measured values: C, 85.52; H, 4.38; N, 7.32; HRMS(ESI) m / z(M+): Theoretical value: 575.20; Measured value: 576.34.

[0380] Synthesis Example 34

[0381] Synthesis Example 34 provides a method for preparing compound M-480, the specific preparation method is as follows:

[0382] Raw materials Mn-B, Mn-A, potassium carbonate, and tetraphenylphosphine palladium were added to toluene, ethanol, and water under nitrogen protection and the mixture was heated to react. After the reaction was completed, the product was purified to obtain the final product. The amounts of the substances and the experimental parameters were the same as in synthesis example 33.

[0383] The structures and yields of the raw materials Mn-B and Mn-A, as well as the products, are shown in Table 4. The elemental analysis results of the prepared compounds are shown in Table 5; the amounts of substances and process parameters are the same as in Synthesis Example 32.

[0384] Table 4

[0385]

[0386] Product characterization data are shown in Table 5:

[0387] Table 5

[0388]

[0389] Device Examples

[0390] The materials used to manufacture the organic electroluminescent device are as follows:

[0391]

[0392] Device Example 1

[0393] This embodiment provides an organic electroluminescent device, such as... Figure 1 As shown, the device includes an anode 2, a hole injection layer 3, a hole transport layer 4, a light-emitting auxiliary layer 5, an electron blocking layer 6, a light-emitting layer 7, an electron transport layer 8, an electron injection layer 9, and a cathode 10, which are sequentially stacked on a substrate 1. The device structure is: anode (indium tin oxide (ITO) coated glass substrate) / hole injection layer (HIL) / hole transport layer (HTL) / light-emitting auxiliary layer (Prime) / electron blocking layer (EBL) / light-emitting layer (EML) / electron transport layer (ETL) / electron injection layer (EIL) / cathode (Al).

[0394] The fabrication of the above-mentioned organic electroluminescent device includes the following steps:

[0395] 1) Substrate cleaning:

[0396] 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.

[0397] 2) Preparation of organic layer:

[0398] 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-emitting auxiliary layer (Prime) (second organic layer) / electron blocking layer (EBL) (first organic layer) / light-emitting layer (EML) / electron transport layer (ETL) / electron injection layer (EIL) / thick cathode (Al) are sequentially deposited on the anode film;

[0399] in:

[0400] The hole injection layer (HIL) is a mixture of NDP-9 and HT, and the specific mass is shown in Table 6.

[0401] The materials of the hole transport layer (HTL) are shown in Table 6;

[0402] The materials of the light-emitting auxiliary layer (Prime) are shown in Table 6;

[0403] The materials of the electron blocking layer (EBL) are shown in Table 6;

[0404] 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 (piq)2Ir(acac). The specific materials of the host material and the ratio of the host material to the guest material are shown in Table 5.

[0405] The materials for the electron transport layer (ETL) are shown in Table 6;

[0406] The material of the electron injection layer (EIL) is LiQ;

[0407] The cathode is made of aluminum.

[0408] The materials used in Device Examples 2-17 and Device Comparative Examples 1-3 are largely the same as those in Device Example 1, with the main difference being the material selection. Specific differences are detailed in Table 6. Table 6 shows some layers of the organic electroluminescent device, along with their materials and thicknesses.

[0409] Table 6

[0410]

[0411]

[0412]

[0413] The examples in the table represent device examples, and the comparative examples in the table are device comparative examples.

[0414] Test Example 1

[0415] The organic electroluminescent devices obtained in Device Examples 1-17 and Comparative Examples 1-3 were tested.

[0416] Instruments: The current, voltage, brightness and other characteristics of the device were tested simultaneously using a PR 650 spectral scanning luminance meter and a Keithley K2400 digital source meter system;

[0417] Test conditions: Photoelectric properties test conditions: current density is 10mA / cm2.

[0418] Lifetime test: The time (in hours) is recorded when the device brightness drops to 95% of its original brightness at a current density of 50mA / cm2.

[0419] The device performance test results are shown in Table 7:

[0420] Table 7

[0421] project Drive voltage (V) Current efficiency (Cd / A) Lifespan T95 (hrs) Device Example 1 3.01 40.76 380.2 Device Example 2 3.01 40.38 375.9 Device Example 3 2.98 40.42 376.5 Device Example 4 2.96 40.37 371.7 Device Example 5 2.99 40.50 378.9 Device Example 6 3.01 40.47 378.1 Device Example 7 3.03 40.26 374.5 Device Example 8 3.02 40.48 377.1 Device Example 9 2.98 40.69 379.8 Device Example 10 3.00 40.54 373.8 Device Example 11 2.97 40.21 374.7 Device Example 12 3.00 40.44 373.5 Device Example 13 3.00 40.28 374.3 Device Example 14 3.00 40.19 370.8 Device Example 15 3.01 40.42 377.7 Device Example 16 3.02 40.18 370.9 Device Example 17 3.00 40.39 377.4 Device Comparison Example 1 3.14 37.27 355.7 Device Comparison Example 2 2.86 38.42 368.9 Device Comparison Example 3 3.27 32.18 360.8

[0422] Device Example 18

[0423] This embodiment provides an organic electroluminescent device, comprising an anode, a hole injection layer, a hole transport layer, an emitting layer, an electron transport layer, an electron injection layer, and a cathode, which are sequentially stacked on a substrate. The device structure is: anode (indium tin oxide (ITO) coated glass substrate) / hole injection layer (HIL) / hole transport layer (HTL) / emitting layer (EML) / electron transport layer (ETL) / electron injection layer (EIL) / cathode (Al).

[0424] The specific preparation process is as follows:

[0425] 1) Substrate cleaning:

[0426] 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.

[0427] 2) Preparation of organic layer:

[0428] 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.

[0429] in:

[0430] 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.

[0431] 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.

[0432] 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 compounds B-1 and M-9 from Synthesis Example 1. The specific ratio of the host material and the guest material is shown in Table 2 below. The thickness is 38 nm and the total evaporation rate is 0.1 nm / s.

[0433] 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.

[0434] 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.

[0435] The cathode is made of aluminum with a thickness of 90 nm and a deposition rate of 1 nm / s.

[0436] The materials used in Device Examples 19-34 are mostly the same as those in Device Example 18, except that the light-emitting layer material is different, as detailed in Table 8.

[0437] Table 8

[0438] Serial Number EML / Thickness Device Example 18 B-1:M-9:RD (mass ratio 47.5:47:5.5) / 35nm Device Example 19 B-39:M-9:RD (mass ratio 47.5:47:5.5) / 35nm Device Example 20 B-45:M-9:RD (mass ratio 47.5:47:5.5) / 35nm Device Example 21 B-53:M-9:RD (mass ratio 47.5:47:5.5) / 35nm Device Example 22 B-54:M-9:RD (mass ratio 47.5:47:5.5) / 35nm Device Example 23 B-59:M-9:RD (mass ratio 47.5:47:5.5) / 35nm Device Example 24 B-64:M-9:RD (mass ratio 47.5:47:5.5) / 35nm Device Example 25 B-117:M-9:RD (mass ratio 47.5:47:5.5) / 35nm Device Example 26 B-140:M-9:RD (mass ratio 47.5:47:5.5) / 35nm Device Example 27 B-152:M-9:RD (mass ratio 47.5:47:5.5) / 35nm Device Example 28 B-158:M-9:RD (mass ratio 47.5:47:5.5) / 35nm Device Example 29 B-208:M-9:RD (mass ratio 47.5:47:5.5) / 35nm Device Example 30 B-211:M-9:RD (mass ratio 47.5:47:5.5) / 35nm Device Example 31 B-243:M-9:RD (mass ratio 47.5:47:5.5) / 35nm Device Example 32 B-249:M-9:RD (mass ratio 47.5:47:5.5) / 35nm Device Example 33 B-265:M-9:RD (mass ratio 47.5:47:5.5) / 35nm Device Example 34 B-297:M-9:RD (mass ratio 47.5:47:5.5) / 35nm Device Comparison Example 4 REF-1:M-9:RD (mass ratio 47.5:47:5.5) / 35nm

[0439] Device Testing Example 2

[0440] The organic electroluminescent devices obtained in Device Examples 18-34 and Device Comparative Example 4 were tested.

[0441] 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;

[0442] Test conditions: Photoelectric property test conditions: current density 10 mA / cm² 2 .

[0443] Lifetime test: current density 50mA / cm 2 The recording time (in hours) was recorded when the device brightness dropped to 95% of its original brightness. The lifetime T95 of device comparative example 4 was set to 100, and the lifetimes of other devices were relative to the lifetime of device comparative example 4. The device performance test results are shown in Table 9.

[0444] Table 9

[0445] Serial Number Drive voltage (V) Current efficiency (Cd / A) Relative lifespan T95 Device Example 18 3.28 39.12 198 Device Example 19 3.31 36.42 151 Device Example 20 3.29 36.32 152 Device Example 21 3.20 36.12 168 Device Example 22 3.29 38.76 195 Device Example 23 3.32 37.87 191 Device Example 24 3.28 37.56 186 Device Example 25 3.29 36.54 153 Device Example 26 3.20 37.98 188 Device Example 27 3.21 37.51 182 Device Example 28 3.22 37.21 156 Device Example 29 3.21 37.28 180 Device Example 30 3.20 37.34 159 Device Example 31 3.29 32.64 131 Device Example 32 3.28 33.78 136 Device Example 33 3.31 30.98 126 Device Example 34 3.29 32.91 133 Device Comparison Example 4 3.42 23.91 100

[0446] 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 in that, It has the structure shown in equation (1): R is selected from hydrogen, deuterium, halogen, cyano, hydroxyl, nitro, substituted or unsubstituted C1-C60 alkyl, substituted or unsubstituted C2-C60 alkenyl, substituted or unsubstituted C3-C60 cycloalkyl, 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; n is selected from integers from 0 to 7. When n is greater than 1, multiple R can exist independently or combine with each other to form substituted or unsubstituted C6-C30 aromatic rings. X and Y are each independently selected from O and S; L1 and L2 are each independently selected from single-bonded, substituted or unsubstituted C6-C60 aryl groups; Ar1 and Ar2 are each independently selected from substituted or unsubstituted C6-C60 aryl groups and substituted or unsubstituted C1-C60 heteroaryl groups; The substituted C1-C60 alkyl, substituted C2-C60 alkenyl, substituted C3-C60 cycloalkyl, substituted C2-C60 ynyl, substituted C3-C60 cycloalkyl, substituted C1-C60 heterocyclic alkyl, substituted C3-C60 cycloalkenyl, substituted C1-C60 heterocyclic alkenyl, substituted C6-C60 arylene, substituted C6-C60 aryl, substituted C1-C The 60 heteroaryl group and the substituents in the substituted C6-C30 aromatic ring are each independently selected from 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, and C6-C60 aryl.

2. The organic electroluminescent compound according to claim 1, characterized in that, The organic electroluminescent compound is selected from one of the following structures:

3. The organic electroluminescent compound according to claim 1 or 2, characterized in that, L1 and L2 are each independently selected from substituted or unsubstituted C6-C25 arylene groups; The substituents in the substituted C6-C25 arylene groups are independently selected from 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, and C6-C25 aryl. Preferably, L1 and L2 are each independently selected from substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted triphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted binatylene, substituted or unsubstituted phenylenenaphthylene, substituted or unsubstituted naphthylphenylene, substituted or unsubstituted fluorene, substituted or unsubstituted phenylenefluorene, substituted or unsubstituted benzo[a]fluorene, substituted or unsubstituted dibenzo[a]fluorene, substituted or unsubstituted phenanthrene, substituted or unsubstituted phenylenephenanthrene, substituted or unsubstituted anthracene; The substituents in the substituted groups are each independently 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, fluorenyl, dibenzofuranyl, dibenzothiophene, or carbazole.

4. The organic electroluminescent compound according to any one of claims 1-3, characterized in that, R is selected from hydrogen, deuterium, halogen, cyano, hydroxyl, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C2-C25 alkenyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C2-C25 alkynyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C3-C25 cycloalkenyl, substituted or unsubstituted C1-C25 heterocyclic alkenyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C1-C25 heteroaryl; Preferably, n is selected from 0-6 and when n is greater than 1, multiple R exist independently or combine with each other to form substituted or unsubstituted C6-C30 aromatic rings; Wherein, the substituents in the substituted C1-C25 alkyl, substituted C2-C25 alkenyl, substituted C3-C25 cycloalkyl, 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, substituted C1-C25 heteroaryl, and substituted C6-C30 aromatic rings are selected from 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, and C6-C25 aryl; Preferably, R is selected from one or more of hydrogen, deuterium, methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, vinyl, n-propenyl, isopropenyl, n-butenyl, and sec-butene; n is selected from 0 to 6, and when n is greater than 1, multiple Rs exist independently or combine with each other to form C6-C30 aromatic rings.

5. The organic electroluminescent compound according to any one of claims 1-4, characterized in that, Ar1 and Ar2 are each independently selected from substituted or unsubstituted C6-C25 aryl groups and substituted or unsubstituted C1-C25 heteroaryl groups; The substituents in the substituted C6-C25 aryl and the substituted C1-C25 heteroaryl are each independently selected from 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, and C6-C25 aryl. 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 indyl, substituted or unsubstituted tetraphenyl, substituted or unsubstituted peryl. Substituted or unsubstituted trefoilyl, substituted or unsubstituted tetraphenyl, substituted or unsubstituted fluoranyl or 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, substituted or unsubstituted tetrazolyl Substituted or unsubstituted furazolidone, 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 benzimidazolyl, 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 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 phenanthidyl, substituted or unsubstituted dipyridyl, substituted or unsubstituted terpyridyl, substituted or unsubstituted phenylterpyridyl, substituted or unsubstituted diazafluorenyl, or substituted or unsubstituted naphthoxazolyl; Wherein, each of the substituents in the above-mentioned substituted groups is independently 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, fluorenyl, dibenzofuranyl, dibenzothiophenyl, or carbazoleyl; Preferably, Ar1 and Ar2 are each independently selected from the following groups:

6. An organic electroluminescent compound according to any one of claims 1-5, characterized in that, The organic electroluminescent compound is selected from one of the following structures:

7. An organic electroluminescent material, characterized in that, The organic electroluminescent material comprises the organic electroluminescent compound according to any one of claims 1-6.

8. An organic electroluminescent device, characterized in that, It includes a first electrode, an organic layer, and a second electrode stacked sequentially. The organic layer comprises an organic electroluminescent compound as described in any one of claims 1-6 or an organic electroluminescent material as described in claim 7.

9. An organic electroluminescent device according to claim 8, characterized in that, The organic layer includes a first light-emitting layer, which contains an organic electroluminescent compound as described in any one of claims 1-6 or an organic electroluminescent compound as described in claim 7.

10. The organic electroluminescent device according to claim 8, characterized in that, The organic layer includes an organic functional layer and a second light-emitting layer; The organic functional layer comprises an organic electroluminescent compound as described in any one of claims 1-6 or an organic electroluminescent material as described in claim 7, and comprises a compound as shown in formula (2): In the formula, X 1 -X 14 Each is independently selected from N or CR, and R is selected from hydrogen or deuterium; Ar 4 Ar 5 Each is independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C6-C60 aromatic amino, or substituted or unsubstituted C3-C60 heteroaryl; The substituents in the substituted C6-C30 aryl, substituted C3-C30 heteroaryl, substituted C6-C60 aromatic amino, and substituted C3-C60 heteroaryl are selected from one or a combination of two of the following: deuterium, halogen, cyano, C1-C6 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 aromatic amino, and C3-C60 heteroarylamine.

11. The organic electroluminescent device according to claim 10, characterized in that, X 1 -X 14 All are selected from CR, and R is selected from hydrogen or deuterium; Preferred, X 1 -X 14 All are selected from CR, where R is selected from hydrogen; Preferred, X 1 -X 6 One of them is selected from N, and the rest are CR; Preferred, X 1 -X 6 One of them is selected from N, and the rest are CR, X 7 -X 14 One of them is selected from N, and the rest are CR; In this context, each R exists independently and may be the same or different; the definition of R is the same as in claim 10. Preferred, Ar 4 -Ar 5 Each group is independently selected from either substituted or unsubstituted A groups; The A group is selected from: phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, fluoranyl, triphenylene, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirodifluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirodifluorenyl, benzofuranyl, dibenzofuranyl, naphthobenzofuranyl, dinaphthofuranyl, benzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, carbazoyl, phenylcarbazoyl, benzomethylcarbazoyl, dibenzocarbazoyl, biphenylcarbazoyl, phenanthrenebenzofuranyl, dibenzofuranfuranyl or phenylcarbazobenzofuranyl; The substituent of the substituted A group is selected from one or a combination of two of the following: deuterium, halogen, cyano, C1-C6 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 aromatic amino, and C3-C60 heteroarylamine.

12. The organic electroluminescent device according to claim 10 or 11, characterized in that, The Ar 4 -Ar 5 Each group is independently selected from phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, fluorenyl, triphenylene, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirodifluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirodifluorenyl, dibenzofuranyl, naphthobenzofuranyl, dibenzothiophenyl, naphthobenzothiophenyl, phenylcarbazoyl, benzophenylcarbazoyl, dibenzophenylcarbazoyl, or groups having the following structures: Multiple Ar ’ When they exist independently, they can be the same or different; Among them, Ar ’ Each C group is independently selected from substituted or unsubstituted C groups, wherein the C groups are selected from: phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, fluorenyl, triphenylene, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirodifluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirodifluorenyl, benzofuranyl, dibenzofuranyl, naphthobenzofuranyl, benzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, carbazoyl, phenylcarbazoyl, benzophenylcarbazoyl or dibenzophenylcarbazoyl; The substituents of the substituted C group are selected from one or a combination of two of the following: deuterium, halogen, cyano, C1-C6 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 aromatic amino, and C3-C60 heteroarylamine.

13. The organic electroluminescent device according to any one of claims 10-12, characterized in that, The material of the second light-emitting layer includes an organic electroluminescent host material composition, which comprises compounds having the structures of formulas (3) and (4) below: In the formula, ring A is a benzene ring; Ar is selected from substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 aromatic amino, substituted or unsubstituted C3-C60 heteroaryl, and substituted or unsubstituted C3-C30 heteroaryl. L 4 Selected from substituted or unsubstituted C6-C30 arylene groups and substituted or unsubstituted C3-C30 heteroarylene groups; The substituents in the substituted C6-C60 aryl, substituted C6-C60 aromatic amino, substituted C3-C60 heteroaryl, substituted C3-C30 heteroaryl, substituted C6-C30 arylene, and substituted C3-C30 heteroarylene are each independently selected from one or a combination of at least two of the following: deuterium, halogen, cyano, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 aromatic amino, and C3-C60 heteroaryl. In the formula, X 1’ -X 14’ Each is independently selected from N or CR ’ R ’ Selected from hydrogen, deuterium, and C6-C30 aryl groups; L 5 Independently selected from the linking bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C3-C30 heteroarylene; Ar 6 Ar 7 Each is independently selected from substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C3-C30 heteroaryl groups; The substituents in the substituted C6-C30 arylene, substituted C3-C30 heteroarylene, substituted C6-C60 aryl, substituted C6-C60 aromatic amino, substituted C3-C60 heteroaryl, and substituted C3-C60 heteroaryl are selected from one or a combination of two of the following: deuterium, halogen, cyano, C1-C6 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, C3-C30 heteroarylene, C6-C60 aromatic amino, and C3-C60 heteroaryl.

14. The organic electroluminescent device according to any one of claims 10-13, characterized in that, In the formula (3), Ar is selected from substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C6-C25 aromatic amino, substituted or unsubstituted C3-C25 heteroaryl, and substituted or unsubstituted C3-C20 heteroaryl. The substituents in the substituted C6-C25 aryl, substituted C6-C25 aromatic amino, substituted C3-C25 heteroaryl, and substituted C3-C20 heteroaryl are each independently selected from one or a combination of at least two of the following: deuterium, halogen, cyano, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C30 aromatic amino, and C3-C30 heteroaryl. Preferably, Ar is selected from substituted or unsubstituted D groups, and the D group is selected from the following groups: phenyl, naphthyl, biphenyl, phenanthryl, fluoranthyl, ... , terphenyl, triphenylene, finadeninyl, phenylnaphthyl, naphthylphenyl, dimethylfluorenyl, phenylmethylfluorenyl, diphenylfluorenyl, pyridyl, pyridylphenyl, phenylpyridyl, spirodifluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirodifluorenyl, dibenzofuranyl, benzonaphthiofuranyl, benzonaphthiopheneyl, spiro[fluoren-9,9'-oxazanthyl]yl, phenylmethylfluorenyl, dinaphthiofuranyl, dinaphthiopheneyl, dibenzothiopheneyl, N,N-diphenylaniline; Wherein, the substituents of the substituted D group are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C30 aromatic amino, and C3-C30 heteroaryl. Preferably, in formula (3), Ar is selected from phenyl, naphthyl, biphenyl, ... yl, phenanthrene, terphenyl, phenylnaphthyl, naphthylphenyl, dimethylfluorenyl, diphenylfluorenyl, spirodifluorenyl, finadenoyl, dibenzofuranyl, benzonaphthylfuranyl, N,N-diphenylaniline; Preferably, in equation (3), L 5 Selected from substituted or unsubstituted C6-C15 arylene groups; wherein each substituent in the substituted C6-C15 arylene group is independently selected from one or a combination of at least two of deuterium, halogen, and C1-C62 alkyl groups; Preferred, L 5 Selected from phenylene, biphenylene, and naphthylene; Preferred, L 5 Selected from phenylene and naphthylene.

15. The organic electroluminescent device according to any one of claims 10-14, characterized in that, In equation (4), X 1’ -X 14’ All selected from CR ’ R ’ The definition is the same as in claim 9; Preferred, X 1’ -X 6’ One of them is selected from N, and the rest are CR. ’ R ’ The definition is the same as in claim 13; Preferred, X 1’ -X 6’ One of them is selected from N, and the rest are CR. ’ ;X 7’ -X 14’ One of them is selected from N, and the rest are CR. ’ R ’ The definition is the same as in claim 13; Preferably, R ’ Selected from hydrogen, deuterium, phenyl, and naphthyl; Ar 6 Ar 7 Each is independently selected from substituted or unsubstituted C6-C18 aryl groups and substituted or unsubstituted C3-C18 heteroaryl groups; The substituents in the substituted C6-C18 aryl and substituted C3-C18 heteroaryl are selected from one or a combination of two of the following: deuterium, halogen, cyano, C1-C6 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 aromatic amino, and C3-C60 heteroaromatic amino. Preferred, Ar 6 Ar 7 Each group is independently selected from substituted or unsubstituted groups E; The group E is selected from: phenyl, naphthyl, biphenyl, terphenyl, phenanthrene, fluorenyl, triphenylene, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirodifluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirodifluorenyl, benzofuranyl, dibenzofuranyl, naphthobenzofuranyl, dinaphthofuranyl, benzothiopheneyl, dibenzothiopheneyl, naphthobenzothiopheneyl, carbazolyl, phenylcarbazolyl, benzophenylcarbazolyl, dibenzophenylcarbazolyl, biphenylcarbazolyl, phenanthrenebenzofuranyl, dibenzofuranfuranyl, phenylcarbazobenzofuranyl; Wherein, the substituent in the substituted group E is selected from one or a combination of two of the following: deuterium, halogen, cyano, C1-C6 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 aromatic amino, and C3-C60 heteroaryl. Preferred, Ar 6 Ar 7 Each is independently selected from phenyl, naphthyl, biphenyl, terphenyl, phenanthrene, fluorenyl, triphenylene, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirodifluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirodifluorenyl, dibenzofuranyl, naphthobenzofuranyl, dibenzothiophenyl, naphthobenzothiophenyl, carbazoleyl, phenylcarbazoleyl, benzocarbazoleyl, and dibenzocarbazoleyl. Preferred, L 5 Each is independently selected from the linking bond, substituted or unsubstituted C6-C18 arylene groups; wherein the substituents in the substituted C6-C18 arylene groups are selected from one or a combination of two of the following: deuterium, halogen, cyano, C1-C6 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 arylamine, and C3-C60 heteroarylamine. Preferred, L 5 Selected from linking bonds and phenylene.

16. An organic electroluminescent device, characterized in that, Includes the organic electroluminescent device according to any one of claims 8-15.

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