Organic compound and application thereof

Abstract

The invention relates to the technical field of display, in particular to an organic compound and application thereof. The organic compound provided by the invention has the structure as shown in the formula (1), so that the organic electroluminescent device containing the organic 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 compound and its applications. Background Technology

[0002] OLED (Organic Light Emitting Diode) is an optical device that integrates a cathode, an anode, and a complex organic layer system sandwiched between the two electrodes. Its organic system encompasses a multi-layered structure from hole injection to electron injection, including hole injection layers, transport layers, auxiliary layers, light-emitting layers (containing host and doped materials), electron buffer and blocking layers, etc. Under appropriate voltage conditions, OLED devices allow holes and electrons to be injected into the light-emitting layer and combine, thereby generating high-energy excited-state compounds. When the excited-state compounds return to the ground state, they release energy in the form of photons, producing a light-emitting effect.

[0003] However, the poor structural stability and poor matching of adjacent energy levels of organic electroluminescent materials in related technologies lead to common defects in OLED devices, such as high driving voltage, low luminous efficiency, and short luminous lifetime, severely hindering the application and development of OLED technology. Improving the performance of organic electroluminescent materials in OLEDs is an important way to overcome these defects. Therefore, developing organic electroluminescent materials with lower driving voltage, higher luminous efficiency, and longer luminous lifetime is an important direction for the development of OLED devices. Summary of the Invention

[0004] The purpose of this invention is to overcome the problems in related technologies, such as poor structural stability and poor matching degree between adjacent energy levels of organic electroluminescent materials, which lead to high driving voltage, low luminous efficiency and short luminous lifetime in organic electroluminescent devices containing such materials. This invention aims to provide an organic compound and its application.

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

[0006]

[0007] In the formula,

[0008] Ar is selected from substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, and substituted or unsubstituted C6-C60 aryloxy groups;

[0009] R 2 For L 2 Ar 2 Ar 2 The A group is selected from substituted or unsubstituted groups, and the A group has the following structure:

[0010]

[0011] L 2 Selected from linking bonds, substituted or unsubstituted C6-C60 arylene groups, and substituted or unsubstituted C3-C60 heteroarylene groups;

[0012] In equations A-1 to A-3, "-*" is a connecting key, and X is selected from S, O, NR, or CR. c1 R c2 ;

[0013] R”, ​​R, R 1 R c1 R c2 Each is independently selected from hydrogen, deuterium, halogen, cyano, hydroxyl, nitro, amido, hydrazine, substituted or unsubstituted C1-C60 alkyl, substituted or unsubstituted C2-C60 alkenyl, substituted or unsubstituted C2-C60 alkynyl, substituted or unsubstituted C3-C60 cycloalkyl, substituted or unsubstituted C1-C60 heterocycloalkyl, substituted or unsubstituted C3-C60 cycloalkenyl, substituted or unsubstituted C1-C60 heterocycloalkenyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C1-C60 heteroaryl;

[0014] n can be any integer from 0 to 7;

[0015] The substituted C1-C60 alkyl, substituted C2-C60 alkenyl, substituted C2-C60 alkynyl, substituted C3-C60 cycloalkyl, substituted C1-C60 heterocycloalkyl, substituted C3-C60 cycloalkenyl, substituted C1-C60 heterocycloalkenyl, substituted C6-C60 aryl, substituted C1-C60 heteroaryl, substituted C6-C60 aryloxy, substituted C6-C60 arylene, substituted C3-C60 heteroarylene, and the substituent of the substituted A group is selected from one or a combination of two of the following: deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 aromatic amino, and C3-C60 heteroarylamine.

[0016] Preferably, the organic compound has any one of the structures of Formula 1-1 to Formula 1-12:

[0017]

[0018] Preferably, Ar is selected from substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C3-C20 heteroaryl, and substituted or unsubstituted C6-C20 aryloxy; and / or,

[0019] L 2 Selected from linking bonds, substituted or unsubstituted C6-C20 arylene groups, substituted or unsubstituted C3-C20 heteroarylene groups; and / or,

[0020] R”, ​​R, R 1 R c1 R c2 Each is independently selected from hydrogen, deuterium, halogen, cyano, hydroxyl, nitro, amido, hydrazine, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 heterocycloalkyl, substituted or unsubstituted C3-C20 cycloalkenyl, substituted or unsubstituted C1-C20 heterocycloalkenyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C1-C20 heteroaryl;

[0021] The substituents in the substituted C1-C20 alkyl, substituted C2-C20 alkenyl, substituted C2-C20 alkynyl, substituted C3-C20 cycloalkyl, substituted C1-C20 heterocycloalkyl, substituted C3-C20 cycloalkenyl, substituted C1-C20 heterocycloalkenyl, substituted C6-C20 aryl, substituted C1-C20 heteroaryl, substituted C6-C20 aryloxy, substituted C6-C20 arylene, and substituted C3-C20 heteroarylene are selected from one or a combination of two of the following: deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 aromatic amino, and C3-C60 heteroarylamine.

[0022] Preferably, when the number of R” is greater than or equal to 2, R” can exist alone or two adjacent to form a substituted or unsubstituted C3-C60 alicyclic ring or a substituted or unsubstituted C6-C60 aromatic ring;

[0023] The substituents in the substituted C3-C60 alicyclic ring and the substituted C6-C60 aromatic ring are selected from one or a combination of two of the following: deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 aromatic amino, and C3-C60 heteroarylamine.

[0024] Preferably, when the number of R” is greater than or equal to 2, R” can exist alone or two adjacent to form a substituted or unsubstituted C6-C30 aromatic ring or a substituted or unsubstituted C3-C30 alicyclic ring;

[0025] The substituents in the substituted C3-C30 alicyclic ring and the substituted C6-C30 aromatic ring are selected from one or a combination of two of the following: deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 aromatic amino, and C3-C60 heteroaromatic amine.

[0026] Preferably, Ar is selected from substituted or unsubstituted B groups, and the B group is selected from the following groups: phenyl, naphthyl, biphenyl, terphenyl, phenanthrene, fluoranyl, triphenylene, phenylnaphthyl, naphthylphenyl, binaphthyl, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirodifluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirodifluorenyl, benzofuranyl, dibenzofuranyl, naphthobenzofuranyl, dinaphthofuranyl, benzothiophene, dibenzothiophene, naphthobenzothiophene, carbazoyl, phenylcarbazoyl, benzocarbazoyl, benzophenylcarbazoyl, dibenzocarbazoyl, biphenylcarbazoyl, phenanthrenebenzofuranyl, benzofuran-benzofuranyl, dibenzofuran-benzofuranyl, phenylcarbazo-benzofuranyl;

[0027] The substituent in the substituted B group is selected from one or a combination of two of the following: deuterium, halogen, cyano, C1-C30 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 arylamine, and C3-C60 heteroarylamine; and / or,

[0028] R”, ​​R, R 1 R c1 R c2 Each C group is independently selected from substituted or unsubstituted C groups, and the C groups are selected from: methyl, ethyl, n-propyl, isopropyl, n-butyl, n-hexyl, n-octyl, isobutyl, tert-butyl, vinyl, propenyl, butenyl, ethynyl, propynyl, butynyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, phenyl, naphthyl, biphenyl, terphenyl, phenanthrene, fluorene, phenylnaphthyl, naphthylphenyl, binaphthyl, fluorene, dimethylfluorene, diphenylfluorene. Spirodifluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirodifluorenyl, benzofuranyl, dibenzofuranyl, naphthobenzofuranyl, dinaphthofuranyl, benzothiopheneyl, dibenzothiopheneyl, naphthobenzothiopheneyl, carbazolyl, phenylcarbazolyl, benzocarbazolyl, benzophenylcarbazolyl, dibenzocarbazolyl, biphenylcarbazolyl, phenanthrenebenzofuranyl, dibenzofuranobenzofuranyl, benzofuranobenzofuranyl, phenylcarbazolyl-benzofuranyl;

[0029] The substituents in the substituted C group are selected from one or a combination of two of the following: deuterium, halogen, cyano, C1-C30 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 aromatic amino, and C3-C60 heteroarylamine.

[0030] Preferably, when the number of R” is greater than or equal to 2, R” can exist alone or two adjacent to each other to form a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted anthracene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted biphenyl ring, a substituted or unsubstituted fluorene ring, a substituted or unsubstituted spirobifluorene ring, a substituted or unsubstituted dimethylfluorene ring, or a substituted or unsubstituted pyrene ring;

[0031] The substituents in the substituted naphthalene ring, substituted benzene ring, substituted anthracene ring, substituted phenanthrene ring, substituted biphenyl ring, substituted fluorene ring, substituted spirofluorene ring, substituted dimethylfluorene ring, and substituted pyrene ring are selected from one or a combination of two of the following: deuterium, halogen, cyano, C1-C30 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 aromatic amino, and C3-C60 heteroarylamine.

[0032] Preferably, when the number of R” is greater than or equal to 2, R” can exist alone or two adjacent to each other to form a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted anthracene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted biphenyl ring, a substituted or unsubstituted fluorene ring, a substituted or unsubstituted spirobifluorene ring, a substituted or unsubstituted dimethylfluorene ring, or a substituted or unsubstituted pyrene ring;

[0033] The substituents in the substituted naphthyl ring, substituted benzene ring, substituted anthracene ring, substituted phenanthrene ring, substituted biphenyl ring, substituted fluorene ring, substituted spirofluorene ring, substituted dimethylfluorene ring, and substituted pyrene ring are selected from deuterium, halogen, cyano, methyl, ethyl, propyl, adamantyl, cyclopropane, cyclohexyl, cyclopentyl, phenyl, naphthyl, biphenyl, anthracene, fluorene, pyrene, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, and carbazole.

[0034] Preferably, Ar is selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl; and / or,

[0035] R”, ​​R, R 1 R c1 R c2 Each is independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenylnaphthyl, substituted or unsubstituted naphthylphenyl;

[0036] The substituents in the substituted phenyl, substituted biphenyl, substituted naphthyl, substituted phenylnaphthyl, and substituted naphthylphenyl are selected from one or a combination of two of the following: deuterium, halogen, cyano, C1-C30 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 arylamine, and C3-C60 heteroarylamine.

[0037] Preferably, Ar is selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl; and / or,

[0038] R”, ​​R, R 1 R c1 R c2 Each is independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenylnaphthyl, substituted or unsubstituted naphthylphenyl;

[0039] The substituents in substituted phenyl, substituted biphenyl, substituted naphthyl, substituted phenylnaphthyl, and substituted naphthylphenyl are selected from deuterium, halogen, cyano, methyl, ethyl, propyl, adamantyl, cyclopropane, cyclohexyl, cyclopentyl, phenyl, naphthyl, biphenyl, anthracene, fluorenyl, pyrene, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, and carbazoyl.

[0040] Preferably, the organic compound is selected from one of the following structures:

[0041]

[0042]

[0043]

[0044]

[0045]

[0046]

[0047]

[0048]

[0049]

[0050]

[0051]

[0052]

[0053]

[0054]

[0055]

[0056]

[0057]

[0058]

[0059]

[0060]

[0061]

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071] The present invention provides an organic electroluminescent material comprising the organic compounds described above.

[0072] Preferably, the organic electroluminescent material further comprises an organic compound represented by formula (2).

[0073]

[0074] In equation (2),

[0075] Ar 3 Ar 4 Each is independently selected from substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C3-C30 heteroaryl groups;

[0076] The substituents of the substituted C6-C30 aryl and the substituted C3-C30 heteroaryl are each independently selected from one or a combination of two of the following: deuterium, halogen, cyano, C1-C30 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 aromatic amino, and C3-C60 heteroarylamine.

[0077] Preferred, Ar 3 Ar 4 Each is independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthryl;

[0078] The substituents in the substituted phenyl, substituted biphenyl, substituted naphthyl, substituted dibenzofuranyl, substituted dibenzothiophene, substituted terphenyl, and substituted phenanthrene are selected from one or a combination of two of the following: deuterium, halogen, cyano, C1-C30 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 aromatic amino, and C3-C60 heteroarylamine.

[0079] Preferred, Ar 3 Selected from dibenzofuranyl, phenyldibenzofuranyl, dibenzothiophenyl, phenyldibenzothiophenyl, benzonaphthofuranyl, and benzonaphthothiophenyl; Ar 4 Selected from phenyl, biphenyl, terphenyl, phenanthrene, naphthyl, phenylnaphthyl, and naphthylphenyl.

[0080] The preferred organic compound represented by formula (2) is selected from any compound from N-1 to N-15:

[0081]

[0082]

[0083] The preparation method of the organic compound represented by formula (2) of this invention is based on Chinese Patent CN116144347A (application number CN202111367059.0).

[0084] Preferably, in the organic electroluminescent material, the mass ratio of the compound shown in formula (1) to the compound shown in formula (2) is 1:9-9:1;

[0085] Preferably, in the organic electroluminescent material, the mass ratio of the compound shown in formula (1) to the compound shown in formula (2) is 2:8-8:2;

[0086] More preferably, in the organic electroluminescent material, the mass ratio of the compound shown in formula (1) to the compound shown in formula (2) is 3:7-7:3;

[0087] More preferably, in the organic electroluminescent material, the mass ratio of the compound shown in formula (1) to the compound shown in formula (2) is 4:6-6:4.

[0088] The present invention also provides an organic electroluminescent device, the organic electroluminescent device comprising an anode, a cathode and an organic layer located between the anode and the cathode, the organic layer comprising an organic compound as described above or an organic electroluminescent material as described above.

[0089] Preferably, the organic layer includes a light-emitting layer, which includes an organic compound as described above or an organic electroluminescent material as described above;

[0090] Preferably, the light-emitting layer comprises a host material and a guest material, wherein the host material comprises an organic compound as described above or an organic electroluminescent material as described above.

[0091] The present invention also provides an electronic device comprising the organic electroluminescent device as described above.

[0092] In the definition of substituent terms in this invention:

[0093] The term "organic electroluminescent material" in this disclosure 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 a host material and a dopant material), an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc.

[0094] The term "multiple organic electroluminescent materials" in this disclosure refers to one or more organic electroluminescent materials comprising a combination of at least two compounds, said materials being contained in any layer constituting an organic electroluminescent device. It can mean both materials contained before (e.g., before vapor deposition) and materials contained after (e.g., after vapor deposition) the organic electroluminescent device. For example, multiple organic electroluminescent materials can be a combination of at least two compounds, said materials being contained in at least one of: 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 at least two compounds can be contained in the same layer or different layers, and can be mixed-evaporated or co-evaporated, or can be evaporated individually.

[0095] In this application, the term "substituent" has its common meaning as known in the art, referring to a chemical moiety covalently attached to or, where appropriate, fused to a parent nucleus group.

[0096] In this application, the term "substituted or unsubstituted" means that the functional group described after the term may or may not have substituents (hereinafter, for ease of description, substituents are collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to an aryl group having a substituent Rc or an unsubstituted aryl group. The aforementioned substituent, i.e., Rc, can be, for example, deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, or C1-C60 heteroaryl. Optionally, it can be, for example, deuterium, a halogen group, cyano, alkyl, haloalkyl, trialkylsilyl, deuterated alkyl, aryl, heteroaryl, etc. Of course, the number of substituents Rc can be one or more. When two substituents Rc are attached to the same atom, the two substituents Rc can exist independently or be connected to each other to form a ring with the atom; when two adjacent substituents Rc exist on a functional group, the adjacent substituents Rc can exist independently or fuse with the functional group to which they are attached to form a ring.

[0097] In this application, the term "alkyl" refers, whether as part of other terms or used alone, to a saturated hydrocarbon group, which may be straight-chain or branched. The term "C1-C60 alkyl" is derived from a monovalent substituent of a straight-chain or branched saturated hydrocarbon having 1 to 60 carbon atoms, preferably 1 to 40 carbon atoms, and more preferably 1 to 20 carbon atoms. Examples of such substituents include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl.

[0098] In this application, the term "C3-C60 cycloalkyl" refers to a cycloalkyl group consisting of at least 3 atoms. More specifically, it refers to a monocyclic or polycyclic hydrocarbon derived from a main chain of 3 to 60 carbon atoms, preferably 3 to 40 carbon atoms, and even more preferably 3 to 20 carbon atoms. Of course, the cycloalkyl group includes, but is not limited to, cyclopropyl, cyclobutyl, adamantyl, etc.

[0099] 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, etc., and arylene groups include, but are not limited to, phenylene, biphenylene, terphenylene, naphthylene, phenanthrylene, anthracene, fluorene, and spirodifluorene, etc.

[0100] In this application, the term "heteroaryl" includes monocyclic, polycyclic, or fused-ring heteroaryl groups, wherein the rings may be interrupted by short non-aromatic units, and the heteroatoms include nitrogen, oxygen, and sulfur. Heteroaryl groups in this application include, but are not limited to, furanyl, phenylthio, pyrroleyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetraazinyl, triazolyl, tetraazolyl, furazolidyl, pyridinyl, pyrazinyl, and pyrimidineyl. Pyridyl, benzofuranyl, benzothiophene, isobenzofuranyl, dibenzofuranyl, dibenzothiophene, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisooxazolyl, benzooxazolyl, isoindolyl, indolyl, indazole, benzothiadiazolyl, quinolinyl, isoquinolinyl, cenolinyl, quinazolinyl, quinoxalolinyl, carbazole, phenoxazinyl, phenthiazinyl, phenanthidyl, benzo-m-dioxacyclopentenyl, dihydroacridyl And their derivatives, etc.; heteroaryl groups include, but are not limited to, pyrifos, pyrrolizyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridinyl, pyridazinyl, benzofuranyl, benzothiopheneyl, isobenzofuranyl, dibenzofuranyl Furanyl, dibenzothiophene, benzimidazolyl, benzithiazolyl, benzisisothiazolyl, benzisisooxazolyl, benzisoxazolyl, isoindolyl, indolyl, ininzolyl, benzisazolyl, benzothiadiazolyl, quinolinyl, isoquinolinyl, cenolinyl, quinazolinyl, quinoxolinyl, carbazolyl, phenoxazinyl, phenoxazinyl, phenanthridineyl, 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.

[0101] In this application, the term "halogen" refers to an atom selected from fluorine, chlorine, bromine, and iodine.

[0102] In this application, unless otherwise stated, hydrogen atoms include protium, deuterium, and tritium.

[0103] 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.

[0104] In this application, if the group is not specified as substituted or unsubstituted, it means that it has not been substituted.

[0105] In this application, the alicyclic ring is monocyclic or polycyclic; the aromatic ring is monocyclic or polycyclic.

[0106] The beneficial effects of this invention are:

[0107] The organic compound provided by this invention is based on the core in the structure of formula (1), and the combination of Ar with specific group substitution and limiting R2 to a specific structure can improve molecular rigidity, thereby increasing the stability of the material; and the HOMO and LUMO energy levels of the organic compound have a high degree of matching with adjacent energy levels, so that the carrier mobility of the organic compound is more balanced, thereby enabling the organic electroluminescent device containing the organic compound to have a lower driving voltage, higher luminous efficiency and longer lifetime;

[0108] Furthermore, by selecting dibenzofuran and similar structures with 1 / 2 / 3 substitution positions as substituents for the triazine group, the invention can avoid complexation between the compound and the metal ions of the doped material, thereby effectively improving the luminous efficiency and extending the luminous lifetime of the device. At the same time, dibenzofuran and similar structures with 1 / 2 / 3 substitution positions are farther away from the triazine group, thereby improving the flexibility of the molecule, further improving the electronic conductivity, and further improving the device efficiency. Attached Figure Description

[0109] 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.

[0110] Figure 1 This is a structural diagram of the organic electroluminescent device in the device embodiment of the present invention;

[0111] 1-Substrate; 2-Anode; 3-Hole injection layer; 4-Hole transport layer; 5-Light emission layer; 6-Electron transport layer; 7-Electron injection layer; 8-Cathode. Detailed Implementation

[0112] 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.

[0113] 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.

[0114] In this invention, the compound represented by formula (1) is prepared via the following synthetic route:

[0115]

[0116] The starting material SA and the raw materials R1-B, R2-C, and R3-D can be purchased directly or synthesized by referring to existing literature reports through conventional reaction routes and conditions.

[0117] The specific structures of the starting material SA and materials R1-B, R2-C, and R3-D used in the embodiments of the present invention are as follows:

[0118] The specific structure of the starting material SA is as follows:

[0119]

[0120]

[0121] The specific structure of the first type of raw material R1-B is as follows:

[0122]

[0123] The specific structure of the second type of raw material R2-C is as follows:

[0124]

[0125] The specific structure of the third-category raw material R3-D is as follows:

[0126]

[0127] Example 1:

[0128] This invention provides a method for preparing compound M-67, the specific steps of which are as follows:

[0129]

[0130] Synthesis of intermediate M67-1: A 100 mL three-necked round-bottom flask with a stir bar was placed in it. Under nitrogen protection, starting material S1, triethylamine (2 mmol), and DCM (10 mL) were added sequentially. The mixture was cooled to 0°C, and then trifluoromethanesulfonic anhydride (1.2 mmol) was slowly added dropwise. After the addition was complete, the mixture was slowly heated to room temperature and reacted for 4 hours. After the reaction was completed, the mixture was quenched with saturated ammonium chloride aqueous solution, extracted with dichloromethane, washed with saturated sodium chloride, and the organic phase was dried over anhydrous magnesium sulfate. The solvent was removed using a rotary evaporator, and the crude product was separated by column chromatography (ethyl acetate: n-hexane = 1:50) to obtain intermediate M67-1 (yield 73%).

[0131] Synthesis of intermediate M67-2: A 100 mL three-necked round-bottom flask was placed with a stir bar and a reflux tube attached. Under nitrogen protection, intermediate M67-1 (1 mmol), starting material R1-1 (1.1 mmol), Pd(dppf)Cl2 (0.03 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL) were added sequentially. The mixture was heated to 90 °C and reacted for 5 hours. After the reaction was completed, the mixture was cooled to room temperature and quenched with saturated ammonium chloride aqueous solution. The mixture was extracted with ethyl acetate, washed with saturated sodium chloride, and dried over anhydrous magnesium sulfate. The solvent was removed using a rotary evaporator. The crude product was separated by column chromatography (ethyl acetate: n-hexane = 1:50) to obtain intermediate M67-2 (yield 79%).

[0132] Synthesis of intermediate M67-3: A 100 mL three-necked round-bottom flask was placed with a stir bar and a reflux tube attached. Under nitrogen protection, intermediate M67-2 (1 mmol), starting material R2-1 (1.1 mmol), Pd(dppf)Cl2 (0.03 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL) were added sequentially. The mixture was heated to 90 °C and reacted for 5 hours. After the reaction was completed, the mixture was cooled to room temperature and quenched with saturated ammonium chloride aqueous solution. The mixture was extracted with ethyl acetate, washed with saturated sodium chloride, and dried over anhydrous magnesium sulfate. The solvent was removed using a rotary evaporator. The crude product was separated by column chromatography (ethyl acetate: n-hexane = 1:50) to obtain intermediate M67-3 (yield 78%).

[0133] Synthesis of intermediate M67-4: A 100 mL three-necked round-bottom flask was fitted with a stir bar and a reflux tube. Under nitrogen protection, intermediate M67-3 (1 mmol), cuprous bromide (1 mmol), and acetonitrile (10 mL) were added sequentially. The temperature was slowly raised to 60 °C, and an acetonitrile solution of isoamyl nitrite (0.1 mmol) was slowly added dropwise. The reaction was carried out at 60 °C for 3 hours. After the reaction was completed, the mixture was cooled to room temperature, quenched with saturated ammonium chloride aqueous solution, extracted with ethyl acetate, washed with saturated sodium chloride, and the organic phase was dried over anhydrous magnesium sulfate. The solvent was removed using a rotary evaporator. The crude product was separated by column chromatography (ethyl acetate: n-hexane = 1:50) to obtain intermediate M67-4 (yield 58%).

[0134] Synthesis of intermediate M67-5: A 100 mL three-necked round-bottom flask was placed with a stir bar and a reflux tube attached. Under nitrogen protection, intermediate M67-4 (1 mmol), diboronate (1.1 mmol), 1,4-dioxane (10 mL), Pd(dppf)Cl2 (0.03 mmol), and potassium acetate (2.5 mmol) were added sequentially. The mixture was heated to 100 °C and reacted for 5 hours. After the reaction was completed, the mixture was cooled to room temperature and extracted with ethyl acetate. The organic phase was dried over anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator. The crude product was separated by column chromatography (ethyl acetate: n-hexane = 1:50) to obtain intermediate M67-5 (yield 81%).

[0135] Synthesis of compound M-67: A 100 mL three-necked round-bottom flask was placed with a stir bar and a reflux tube attached. Under nitrogen protection, intermediate M67-5 (1 mmol), starting material R3-2 (1.1 mmol), Pd(dppf)Cl2 (0.03 mmol), potassium carbonate (2.5 mmol), and 1,4-dioxane / water (10 mL / 2 mL) were added sequentially. The mixture was heated to 90 °C and reacted for 5 hours. After the reaction was completed, 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 o-dichlorobenzene to obtain compound M-67 (yield 57%).

[0136] Elemental analysis: C 47 H 29 N3O; Theoretical values: C, 88.61; H, 4.49; N, 6.45; O, 2.45; Measured values: C, 88.60; H, 4.54; N, 6.41; HRMS(ESI) m / z [M+H]+: Theoretical value: 651.2311; Measured value: 652.2341.

[0137] Example 2:

[0138] This invention provides a method for preparing compound M-138, the specific steps of which are as follows:

[0139]

[0140] Synthesis of intermediate M138-1: The synthesis steps of intermediate M138-1 are the same as those of M67-1, except that raw material S1 is replaced with raw material S2, thus obtaining intermediate M138-1 (yield 72%).

[0141] Synthesis of intermediate M138-2: The synthesis steps of intermediate M138-2 are the same as those of M67-2, except that intermediate M67-1 is replaced with intermediate M138-1, thus obtaining intermediate M138-2 (yield 78%).

[0142] Synthesis of intermediate M138-3: The synthesis steps of intermediate M138-3 are the same as those of M67-3, except that intermediate M67-2 is replaced with intermediate M138-2, and raw material R2-1 is replaced with raw material R2-3, thus obtaining intermediate M138-3 (yield 72%).

[0143] Synthesis of intermediate M138-4: The synthesis steps of intermediate M138-4 are the same as those of M67-4, except that intermediate M67-3 is replaced with intermediate M138-3 to obtain intermediate M138-4 (yield 60%).

[0144] Synthesis of intermediate M138-5: The synthesis steps of intermediate M138-5 are the same as those of M67-5, except that intermediate M67-4 is replaced with intermediate M138-4 to obtain intermediate M138-5 (yield 81%).

[0145] Synthesis of compound M-138: The synthesis steps of compound M-138 are the same as those of M-67, except that intermediate M67-5 is replaced with intermediate M138-5 to obtain compound M-138 (yield 58%).

[0146] Elemental analysis: C 47 H 29 N3O; Theoretical values: C, 87.28; H, 4.45; N, 5.99; O, 2.28; Measured values: C, 87.27; H, 4.44; N, 6.00; HRMS(ESI) m / z [M+H]+: Theoretical value: 701.2467; Measured value: 702.2454.

[0147] Example 3:

[0148] This invention provides a method for preparing compound M-176, the specific steps of which are as follows:

[0149]

[0150] Synthesis of intermediate M176-1: The synthesis steps of intermediate M176-1 are the same as those of M67-1, except that raw material S1 is replaced with raw material S3 to obtain intermediate M176-1 (yield 73%).

[0151] Synthesis of intermediate M176-2: The synthesis steps of intermediate M176-2 are the same as those of M67-2, except that intermediate M67-1 is replaced with intermediate M176-1, and raw material R1-1 is replaced with raw material R1-2, thus obtaining intermediate M176-2 (yield 79%).

[0152] Synthesis of intermediate M176-3: The synthesis steps of intermediate M176-3 are the same as those of M67-3, except that intermediate M67-2 is replaced with intermediate M176-2, and raw material R2-1 is replaced with raw material R2-4, thus obtaining intermediate M176-3 (yield 71%).

[0153] Synthesis of intermediate M176-4: The synthesis steps of intermediate M176-4 are the same as those of M67-4, except that intermediate M67-3 is replaced with intermediate M176-3 to obtain intermediate M176-4 (yield 58%).

[0154] Synthesis of intermediate M176-5: The synthesis steps of intermediate M176-5 are the same as those of M67-5, except that intermediate M67-4 is replaced with intermediate M176-4 to obtain intermediate M176-5 (yield 80%).

[0155] Synthesis of compound M-176: The synthesis steps of compound M-176 are the same as those of M-67, except that intermediate M67-5 is replaced with intermediate M138-5 to obtain compound M-176 (yield 59%).

[0156] Elemental analysis: C 47 H 29 N3O; Theoretical values: C, 87.46; H, 4.57; N, 5.77; O, 2.20; Measured values: C, 87.47; H, 4.52; N, 5.74; HRMS(ESI) m / z [M+H]+: Theoretical value: 727.2624; Measured value: 728.2653.

[0157] Example 4:

[0158] This invention provides a method for preparing compound M-200, the specific steps of which are as follows:

[0159]

[0160] Synthesis of intermediate M200-1: The synthesis steps of intermediate M200-1 are the same as those of M67-1, except that raw material S1 is replaced with raw material S4 to obtain intermediate M200-1 (yield 72%).

[0161] Synthesis of intermediate M200-2: The synthesis steps of intermediate M200-2 are the same as those of M67-2, except that intermediate M67-1 is replaced with intermediate M200-1 to obtain intermediate M200-2 (yield 80%).

[0162] Synthesis of intermediate M200-3: The synthesis steps of intermediate M200-3 are the same as those of M67-3, except that intermediate M67-2 is replaced with intermediate M200-2 to obtain intermediate M200-3 (yield 70%).

[0163] Synthesis of intermediate M200-4: The synthesis steps of intermediate M200-4 are the same as those of M67-4, except that intermediate M67-3 is replaced with intermediate M200-3 to obtain intermediate M200-4 (yield 59%).

[0164] Synthesis of intermediate M200-5: The synthesis steps of intermediate M200-5 are the same as those of M67-5, except that intermediate M67-4 is replaced with intermediate M200-4 to obtain intermediate M200-5 (yield 80%).

[0165] Synthesis of compound M-200: The synthesis steps of compound M-200 are the same as those of M-67, except that intermediate M67-5 is replaced with intermediate M200-5 to obtain compound M-200 (yield 60%).

[0166] Elemental analysis: C 47 H 29 N3O; Theoretical values: C, 86.61; H, 4.49; N, 6.45; O, 2.45; Measured values: C, 86.59; H, 4.49; N, 6.47; HRMS(ESI) m / z [M+H]+: Theoretical value: 651.2311; Measured value: 652.3221.

[0167] Example 5:

[0168] This invention provides a method for preparing compound M-454, the specific steps of which are as follows:

[0169]

[0170] Synthesis of intermediate M454-1: The synthesis steps of intermediate M454-1 are the same as those of M67-1, except that raw material S1 is replaced with raw material S5 to obtain intermediate M454-1 (yield 71%).

[0171] Synthesis of intermediate M454-2: The synthesis steps of intermediate M454-2 are the same as those of M67-2, except that intermediate M67-1 is replaced with intermediate M454-1, and raw material R1-1 is replaced with raw material R1-2, thus obtaining intermediate M454-2 (yield 79%).

[0172] Synthesis of intermediate M454-3: The synthesis steps of intermediate M454-3 are the same as those of M67-3, except that intermediate M67-2 is replaced with intermediate M454-2, and raw material R2-1 is replaced with raw material R2-3, thus obtaining intermediate M454-3 (yield 71%).

[0173] Synthesis of intermediate M454-4: The synthesis steps of intermediate M454-4 are the same as those of M67-4, except that intermediate M67-3 is replaced with intermediate M454-3 to obtain intermediate M454-4 (yield 60%).

[0174] Synthesis of intermediate M454-5: The synthesis steps of intermediate M454-5 are the same as those of M67-5, except that intermediate M67-4 is replaced with intermediate M454-4 to obtain intermediate M454-5 (yield 81%).

[0175] Synthesis of compound M-454: The synthesis steps of compound M-454 are the same as those of M-67, except that intermediate M67-5 is replaced with intermediate M454-5, and starting material R3-2 is replaced with starting material R3-1, thus obtaining compound M-454 (yield 58%).

[0176] Elemental analysis: C 47 H 29 N3O; Theoretical values: C, 87.28; H, 4.45; N, 5.99; O, 2.28; Measured values: C, 87.27; H, 4.45; N, 5.98; HRMS(ESI) m / z [M+H]+: Theoretical value: 701.2467; Measured value: 702.2359.

[0177] Example 6:

[0178] This invention provides a method for preparing compound M-530, the specific steps of which are as follows:

[0179]

[0180] Synthesis of intermediate M530-1: The synthesis steps of intermediate M530-1 are the same as those of M67-1, except that raw material S1 is replaced with raw material S6 to obtain intermediate M530-1 (yield 71%).

[0181] Synthesis of intermediate M530-2: The synthesis steps of intermediate M530-2 are the same as those of M67-2, except that intermediate M67-1 is replaced with intermediate M530-1, and raw material R1-1 is replaced with raw material R1-2, thus obtaining intermediate M530-2 (yield 79%).

[0182] Synthesis of intermediate M530-3: The synthesis steps of intermediate M530-3 are the same as those of M67-3, except that intermediate M67-2 is replaced with intermediate M530-2, and raw material R2-1 is replaced with raw material R2-2, thus obtaining intermediate M530-3 (yield 71%).

[0183] Synthesis of intermediate M530-4: The synthesis steps of intermediate M530-4 are the same as those of M67-4, except that intermediate M67-3 is replaced with intermediate M530-3 to obtain intermediate M530-4 (yield 60%).

[0184] Synthesis of intermediate M530-5: The synthesis steps of intermediate M530-5 are the same as those of M67-5, except that intermediate M67-4 is replaced with intermediate M530-4 to obtain intermediate M530-5 (yield 81%).

[0185] Synthesis of compound M-530: The synthesis steps of compound M-530 are the same as those of M-67, except that intermediate M67-5 is replaced with intermediate M530-5, and starting material R3-2 is replaced with starting material R3-3, thus obtaining compound M-530 (yield 58%).

[0186] Elemental analysis: C 47 H 29 N3O; Theoretical values: C, 87.28; H, 4.45; N, 5.99; O, 2.28; Measured values: C, 87.26; H, 4.44; N, 5.98; HRMS(ESI) m / z [M+H]+: Theoretical value: 701.2467; Measured value: 702.2615.

[0187] Example 7:

[0188] This invention provides a method for preparing compound M-584, the specific steps of which are as follows:

[0189]

[0190] Synthesis of intermediate M584-1: The synthesis steps of intermediate M584-1 are the same as those of M67-1, except that raw material S1 is replaced with raw material S7 to obtain intermediate M584-1 (yield 70%).

[0191] Synthesis of intermediate M584-2: The synthesis steps of intermediate M584-2 are the same as those of M67-2. Using intermediate M584-1, and replacing raw material R1-1 with raw material R1-2, intermediate M584-2 can be obtained (yield 79%).

[0192] Synthesis of intermediate M584-3: The synthesis steps of intermediate M584-3 are the same as those of M67-3, except that intermediate M67-2 is replaced with intermediate M530-2, and raw material R2-1 is replaced with raw material R2-3, thus obtaining intermediate M584-3 (yield 72%).

[0193] Synthesis of intermediate M584-4: The synthesis steps of intermediate M584-4 are the same as those of M67-4, except that intermediate M67-3 is replaced with intermediate M530-3 to obtain intermediate M584-4 (yield 61%).

[0194] Synthesis of intermediate M584-5: The synthesis steps of intermediate M584-5 are the same as those of M67-5, except that intermediate M67-4 is replaced with intermediate M530-4 to obtain intermediate M584-5 (yield 80%).

[0195] Synthesis of compound M-584: The synthesis steps of compound M-584 are the same as those of M-67, except that intermediate M67-5 is replaced with intermediate M530-5, and starting material R3-2 is replaced with starting material R3-1, thus obtaining compound M-584 (yield 57%).

[0196] Elemental analysis: C 47 H 29 N3O; Theoretical values: C, 87.28; H, 4.45; N, 5.99; O, 2.28; Measured values: C, 87.25; H, 4.44; N, 5.99; HRMS(ESI) m / z [M+H]+: Theoretical value: 701.2467; Measured value: 702.1124.

[0197] Example 8:

[0198] This invention provides a method for preparing compound M-660, the specific steps of which are as follows:

[0199]

[0200] Synthesis of intermediate M660-1: The synthesis steps of intermediate M660-1 are the same as those of M67-1, except that raw material S1 is replaced with raw material S8 to obtain intermediate M660-1 (yield 70%).

[0201] Synthesis of intermediate M660-2: The synthesis steps of intermediate M660-2 are the same as those of M67-2, except that intermediate M67-1 is replaced with intermediate M660-1, and raw material R1-1 is replaced with raw material R1-2, thus obtaining intermediate M660-2 (yield 79%).

[0202] Synthesis of intermediate M660-3: The synthesis steps of intermediate M660-3 are the same as those of M67-3, except that intermediate M67-2 is replaced with intermediate M660-2, and raw material R2-1 is replaced with raw material R2-3, thus obtaining intermediate M660-3 (yield 72%).

[0203] Synthesis of intermediate M660-4: The synthesis steps of intermediate M660-4 are the same as those of M67-4, except that intermediate M67-3 is replaced with intermediate M660-3 to obtain intermediate M660-4 (yield 61%).

[0204] Synthesis of intermediate M660-5: The synthesis steps of intermediate M660-5 are the same as those of M67-5, except that intermediate M67-4 is replaced with intermediate M660-4 to obtain intermediate M660-5 (yield 80%).

[0205] Synthesis of compound M-660: The synthesis steps of compound M-660 are the same as those of M-67, except that intermediate M67-5 is replaced with intermediate M660-5, and starting material R3-2 is replaced with starting material R3-3, thus obtaining compound M-660 (yield 57%).

[0206] Elemental analysis: C 47 H 29 N3O; Theoretical values: C, 87.28; H, 4.45; N, 5.99; O, 2.28; Measured values: C, 87.26; H, 4.47; N, 5.97; HRMS(ESI) m / z [M+H]+: Theoretical value: 701.2467; Measured value: 702.2138.

[0207] Example 9:

[0208] This invention provides a method for preparing compound M-704, the specific steps of which are as follows:

[0209]

[0210] Synthesis of intermediate M704-1: The synthesis steps of intermediate M704-1 are the same as those of M67-1, except that raw material S1 is replaced with raw material S9 to obtain intermediate M704-1 (yield 73%).

[0211] Synthesis of intermediate M704-2: The synthesis steps of intermediate M704-2 are the same as those of M67-2, except that intermediate M67-1 is replaced with intermediate M704-1, and raw material R1-1 is replaced with raw material R1-2, thus obtaining intermediate M704-2 (yield 78%).

[0212] Synthesis of intermediate M704-3: The synthesis steps of intermediate M704-3 are the same as those of M67-3, except that intermediate M67-2 is replaced with intermediate M704-2 to obtain intermediate M704-3 (yield 70%).

[0213] Synthesis of intermediate M704-4: The synthesis steps of intermediate M704-4 are the same as those of M67-4, except that intermediate M67-3 is replaced with intermediate M704-3 to obtain intermediate M704-4 (yield 58%).

[0214] Synthesis of intermediate M704-5: The synthesis steps of intermediate M704-5 are the same as those of M67-5, except that intermediate M67-4 is replaced with intermediate M704-4 to obtain intermediate M704-5 (yield 81%).

[0215] Synthesis of compound M-704: The synthesis steps of compound M-704 are the same as those of M-67, except that intermediate M67-5 is replaced with intermediate M704-5 to obtain compound M-704 (yield 57%).

[0216] Elemental analysis: C 47 H 29 N3O; Theoretical values: C, 86.61; H, 4.49; N, 6.45; O, 2.45; Measured values: C, 86.58; H, 4.48; N, 6.46; HRMS(ESI) m / z [M+H]+: Theoretical value: 651.2311; Measured value: 652.3221.

[0217] Example 10:

[0218] This invention provides a method for preparing compound M-813, the specific steps of which are as follows:

[0219]

[0220] Synthesis of intermediate M813-1: The synthesis steps of intermediate M813-1 are the same as those of M67-1, except that raw material S1 is replaced with raw material S10 to obtain intermediate M813-1 (yield 72%).

[0221] Synthesis of intermediate M813-2: The synthesis steps of intermediate M813-2 are the same as those of M67-2, except that intermediate M67-1 is replaced with intermediate M813-1 to obtain intermediate M813-2 (yield 79%).

[0222] Synthesis of intermediate M813-3: The synthesis steps of intermediate M813-3 are the same as those of M67-3, except that intermediate M67-2 is replaced with intermediate M813-2, and raw material R2-1 is replaced with raw material R2-3, thus obtaining intermediate M813-3 (yield 71%).

[0223] Synthesis of intermediate M813-4: The synthesis steps of intermediate M813-4 are the same as those of M67-4, except that intermediate M67-3 is replaced with intermediate M813-3 to obtain intermediate M813-4 (yield 61%).

[0224] Synthesis of intermediate M813-5: The synthesis steps of intermediate M813-5 are the same as those of M67-5, except that intermediate M67-4 is replaced with intermediate M813-4 to obtain intermediate M813-5 (yield 80%).

[0225] Synthesis of compound M-813: The synthesis steps of compound M-813 are the same as those of M-67, except that intermediate M67-5 is replaced with intermediate M813-5, and starting material R3-2 is replaced with starting material R3-1, thus obtaining compound M-813 (yield 57%).

[0226] Elemental analysis: C 47 H 29 N3O; Theoretical values: C, 87.28; H, 4.45; N, 5.99; O, 2.28; Measured values: C, 87.27; H, 4.45; N, 5.98; HRMS(ESI) m / z [M+H]+: Theoretical value: 701.2467; Measured value: 702.2371.

[0227] Example 11:

[0228] This invention provides a method for preparing compound M-857, the specific steps of which are as follows:

[0229]

[0230] Synthesis of intermediate M857-2: The synthesis steps of intermediate M857-2 are the same as those of M67-2, except that intermediate M67-1 is replaced with intermediate M813-1, and raw material R1-1 is replaced with raw material R1-2, thus obtaining intermediate M857-2 (yield 75%).

[0231] Synthesis of intermediate M857-3: The synthesis steps of intermediate M857-3 are the same as those of M67-3, except that intermediate M67-2 is replaced with intermediate M857-2 to obtain intermediate M857-3 (yield 70%).

[0232] Synthesis of intermediate M857-4: The synthesis steps of intermediate M857-4 are the same as those of M67-4, except that intermediate M67-3 is replaced with intermediate M857-3 to obtain intermediate M857-4 (yield 60%).

[0233] Synthesis of intermediate M857-5: The synthesis steps of intermediate M857-5 are the same as those of M67-5, except that intermediate M67-4 is replaced with intermediate M857-4 to obtain intermediate M857-5 (yield 78%).

[0234] Synthesis of compound M-857: The synthesis steps of compound M-857 are the same as those of M-67, except that intermediate M67-5 is replaced with intermediate M857-5, and starting material R3-2 is replaced with starting material R3-3, thus obtaining compound M-857 (yield 55%).

[0235] Elemental analysis: C 47 H 29 N3O; Theoretical values: C, 86.61; H, 4.49; N, 6.45; O, 2.45; Measured values: C, 86.57; H, 4.49; N, 6.44; HRMS(ESI) m / z [M+H]+: Theoretical value: 651.2311; Measured value: 652.2127.

[0236] Example 12:

[0237] This invention provides a method for preparing compound M-900, the specific steps of which are as follows:

[0238]

[0239] Synthesis of intermediate M900-1: The synthesis steps of intermediate M900-1 are the same as those of M67-1, except that raw material S1 is replaced with raw material S11 to obtain intermediate M900-1 (yield 73%).

[0240] Synthesis of intermediate M900-2: The synthesis steps of intermediate M900-2 are the same as those of M67-2, except that intermediate M67-1 is replaced with intermediate M900-1, and raw material R1-1 is replaced with raw material R1-2, thus obtaining intermediate M900-2 (yield 80%).

[0241] Synthesis of intermediate M900-3: The synthesis steps of intermediate M900-3 are the same as those of M67-3, except that intermediate M67-2 is replaced with intermediate M900-2 to obtain intermediate M900-3 (yield 71%).

[0242] Synthesis of intermediate M900-4: The synthesis steps of intermediate M900-4 are the same as those of M67-4, except that intermediate M67-3 is replaced with intermediate M900-3 to obtain intermediate M900-4 (yield 60%).

[0243] Synthesis of intermediate M900-5: The synthesis steps of intermediate M900-5 are the same as those of M67-5, except that intermediate M67-4 is replaced with intermediate M900-4 to obtain intermediate M900-5 (yield 79%).

[0244] Synthesis of compound M-900: The synthesis steps of compound M-900 are the same as those of M-67, except that intermediate M67-5 is replaced with intermediate M900-5 to obtain compound M-900 (yield 56%).

[0245] Elemental analysis: C 47 H 29 N3O; Theoretical values: C, 86.61; H, 4.49; N, 6.45; O, 2.45; Measured values: C, 86.60; H, 4.49; N, 6.45; HRMS(ESI) m / z [M+H]+: Theoretical value: 651.2311; Measured value: 652.2209.

[0246] Example 13:

[0247] This invention provides a method for preparing compound M-930, the specific steps of which are as follows:

[0248]

[0249] Synthesis of intermediate M930-1: The synthesis steps of intermediate M930-1 are the same as those of M67-1, except that raw material S1 is replaced with raw material S12 to obtain intermediate M930-1 (yield 72%).

[0250] Synthesis of intermediate M930-2: The synthesis steps of intermediate M930-2 are the same as those of M67-2, except that intermediate M67-1 is replaced with intermediate M930-1, and raw material R1-1 is replaced with raw material R1-2, thus obtaining intermediate M930-2 (yield 81%).

[0251] Synthesis of intermediate M930-3: The synthesis steps of intermediate M930-3 are the same as those of M67-3, except that intermediate M67-2 is replaced with intermediate M930-2, and raw material R2-1 is replaced with raw material R2-4, thus obtaining intermediate M930-3 (yield 69%).

[0252] Synthesis of intermediate M930-4: The synthesis steps of intermediate M930-4 are the same as those of M67-4, except that intermediate M67-3 is replaced with intermediate M930-3 to obtain intermediate M930-4 (yield 62%).

[0253] Synthesis of intermediate M930-5: The synthesis steps of intermediate M930-5 are the same as those of M67-5, except that intermediate M67-4 is replaced with intermediate M930-4 to obtain intermediate M930-5 (yield 79%).

[0254] Synthesis of compound M-930: The synthesis steps of compound M-930 are the same as those of M-67, except that intermediate M67-5 is replaced with intermediate M930-5, and starting material R3-2 is replaced with starting material R3-3, thus obtaining compound M-930 (yield 57%).

[0255] Elemental analysis: C 47 H 29 N3O; Theoretical values: C, 87.46; H, 4.57; N, 5.77; O, 2.20; Measured values: C, 87.47; H, 4.55; N, 5.75; HRMS(ESI) m / z [M+H]+: Theoretical value: 727.2624; Measured value: 728.1455.

[0256] Example 14:

[0257] This invention provides a method for preparing compound M-991, the specific steps of which are as follows:

[0258]

[0259] Synthesis of intermediate M991-3: The synthesis steps of intermediate M991-3 are the same as those of M67-3, except that intermediate M67-2 is replaced with intermediate M930-2 to obtain intermediate M991-3 (yield 71%).

[0260] Synthesis of intermediate M991-4: The synthesis steps of intermediate M991-4 are the same as those of M67-4, except that intermediate M67-3 is replaced with intermediate M930-3 to obtain intermediate M991-4 (yield 59%).

[0261] Synthesis of intermediate M991-5: The synthesis steps of intermediate M991-5 are the same as those of M67-5, except that intermediate M67-4 is replaced with intermediate M930-4 to obtain intermediate M991-5 (yield 79%).

[0262] Synthesis of compound M-991: The synthesis steps of compound M-991 are the same as those of M-67, except that intermediate M67-5 is replaced with intermediate M930-5, and starting material R3-2 is replaced with starting material R3-3, thus obtaining compound M-991 (yield 55%).

[0263] Elemental analysis: C 47 H 29 N3O; Theoretical values: C, 86.61; H, 4.49; N, 6.45; O, 2.45; Measured values: C, 86.57; H, 4.48; N, 6.45; HRMS(ESI) m / z [M+H]+: Theoretical value: 651.2311; Measured value: 652.2057.

[0264] Example 15:

[0265] This invention provides a method for preparing compound M-1154, the specific steps of which are as follows:

[0266]

[0267] Synthesis of compound M-1154: The synthesis steps of compound M-1154 are the same as those of compound M-67, except that the starting material R3-2 is replaced with starting material R3-4, which yields compound M-1154 (yield 52%).

[0268] Elemental analysis: C 47 H 29 N3O; Theoretical values: C, 88.01; H, 4.54; N, 5.40; O, 2.06; Measured values: C, 88.00; H, 4.52; N, 5.41; HRMS(ESI) m / z [M+H]+: Theoretical value: 777.2780; Measured value: 778.1004.

[0269] Example 16:

[0270] This invention provides a method for preparing compound M-1155, the specific steps of which are as follows:

[0271]

[0272] Synthesis of compound M-1155: The synthesis steps of compound M-1155 are the same as those of compound M-67, except that the starting material R3-2 is replaced with starting material R3-5, which yields compound M-1155 (yield 51%).

[0273] Elemental analysis: C 47 H 29 N3O; Theoretical value: C, 88.01; H, 4.54; N, 5.40; O, 2.06; Measured value: C, 88.01; H, 4.53; N, 5.40; HRMS(ESI) m / z [M+H]+: Theoretical value: 777.2780; Measured value: 778.2449.

[0274] Example 17:

[0275] This invention provides a method for preparing compound M-1159, the specific steps of which are as follows:

[0276]

[0277] Synthesis of compound M-1159: The synthesis steps of compound M-1159 are the same as those of compound M-67, except that the starting material R3-2 is replaced with starting material R3-6, which yields compound M-1159 (yield 50%).

[0278] Elemental analysis: C 47 H 29 N3O; Theoretical values: C, 87.28; H, 4.45; N, 5.99; O, 2.28; Measured values: C, 87.28; H, 4.44; N, 6.00; HRMS(ESI) m / z [M+H]+: Theoretical value: 701.2467; Measured value: 702.1490.

[0279] Example 18:

[0280] This invention provides a method for preparing compound M-1160, the specific steps of which are as follows:

[0281]

[0282] Synthesis of compound M-1160: The synthesis steps of compound M-1160 are the same as those of compound M-67, except that the starting material R3-2 is replaced with starting material R3-7, which yields compound M-1160 (yield 52%).

[0283] Elemental analysis: C 47 H 29N3O; Theoretical values: C, 87.46; H, 4.57; N, 5.77; O, 2.20; Measured values: C, 87.43; H, 4.58; N, 5.77; HRMS(ESI) m / z [M+H]+: Theoretical value: 727.2624; Measured value: 728.2144.

[0284] Example 19:

[0285] This invention provides a method for preparing compound M-1169, the specific steps of which are as follows:

[0286]

[0287] Synthesis of compound M-1169: The synthesis steps of compound M-1169 are the same as those of compound M-67, except that the starting material R3-2 is replaced with the starting material R3-8, which yields compound M-1169 (yield 51%).

[0288] Elemental analysis: C 47 H 29 N3O; Theoretical values: C, 85.33; H, 4.35; N, 5.85; S, 4.47; Measured values: C, 85.33; H, 4.38; N, 5.86; S, 4.43; HRMS(ESI) m / z [M+H]+: Theoretical value: 717.2239; Measured value: 718.3145.

[0289] Example 20:

[0290] This invention provides a method for preparing compound M-1171, the specific steps of which are as follows:

[0291]

[0292] Synthesis of compound M-1171: The synthesis steps of compound M-1171 are the same as those of compound M-67, except that the starting material R3-2 is replaced with starting material R3-9, which yields compound M-1171 (yield 51%).

[0293] Elemental analysis: C 47 H 29 N3O; Theoretical value: C, 87.58; H, 4.71; N, 7.71; Measured value: C, 87.57; H, 4.70; N, 7.73; HRMS(ESI) m / z [M+H]+: Theoretical value: 726.2783; Measured value: 727.3148.

[0294] Example 21:

[0295] This invention provides a method for preparing compound M-1176, the specific steps of which are as follows:

[0296]

[0297] Synthesis of compound M-1176: The synthesis steps of compound M-1176 are the same as those of compound M-67, except that the starting material R3-2 is replaced with starting material R3-10, which yields compound M-1176 (yield 52%).

[0298] Elemental analysis: C 47 H 29 N3O; Theoretical value: C, 88.60; H, 5.20; N, 6.20; Measured value: C, 88.59; H, 5.21; N, 6.20; HRMS(ESI) m / z [M+H]+: Theoretical value: 677.2831; Measured value: 678.1065.

[0299] Device Examples:

[0300] This invention provides an OLED device composed of different organic electroluminescent materials, the specific structural distribution of which is as follows: Figure 1 As shown, the OLED device has the following layer structure: substrate 1 (coated glass substrate with indium tin oxide (ITO) as anode 2) / hole injection layer 3 (HIL) / hole transport layer 4 (HTL) / light emission layer 5 (EML) / electron transport layer 6 (ETL) / electron injection layer (EIL) 7 / cathode 8.

[0301] The materials used in the OLED device are as follows:

[0302]

[0303] The fabrication of devices in Examples 1-24 and Comparative Examples 1-14 includes the following steps:

[0304] (1) Substrate cleaning:

[0305] 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%), rinsed in deionized water, ultrasonically degreased in an acetone:ethanol mixed solvent (volume ratio 1:1), baked in a clean environment until all moisture was removed, and then cleaned with ultraviolet light and ozone.

[0306] (2) Evaporation of organic light-emitting functional layer:

[0307] The glass substrate with the anode layer was placed in a vacuum chamber and evacuated to a vacuum level of 1×10⁻⁶. -6 Up to 2×10 -4Pa, a mixture of HATCN and HT is vacuum-deposited on the above-mentioned anodic layer film, wherein the mass ratio of HATCN to HT is 3:97, as a hole injection layer, and the deposition thickness is 10 nm.

[0308] A hole transport layer (material HT) is deposited on the hole injection layer, with a film thickness of 80 nm.

[0309] The light-emitting layer is deposited on the hole transport layer. The specific preparation method is as follows: the light-emitting host material (the materials are shown in Table 1) and the guest material (piq)2Ir(acac) are vacuum deposited by co-evaporation, and the total film thickness is 35nm.

[0310] An electron transport layer is deposited on the light-emitting layer. The specific preparation method is as follows: ET and LiQ are vacuum deposited by co-evaporation, and the total film thickness is 30nm.

[0311] An electron injection layer (LiQ material) was vacuum-deposited on the electron transport layer, with a total film thickness of 1 nm.

[0312] Al was deposited on the electron injection layer, with a total film thickness of 90 nm.

[0313] The parameters of each layer, its material, and its thickness in the device are shown in Table 1 below:

[0314] Table 1

[0315]

[0316]

[0317]

[0318]

[0319] In Table 1, the examples refer to device examples, and the comparative examples refer to device comparative examples.

[0320] The organic electroluminescent devices obtained in Device Examples 1-24 and Comparative Examples 1-14 were tested.

[0321] Instruments: The current, voltage, brightness, emission spectrum and other characteristics of the device were tested simultaneously using a PR650 spectral scanning luminance meter and a Keithley K2400 digital source meter system;

[0322] Test conditions: Photoelectric properties test conditions: current density is 10mA / cm2.

[0323] 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.

[0324] The device performance test results are shown in Table 5:

[0325] Table 5

[0326] project Drive voltage (V) Current efficiency (Cd / A) Lifespan T95 (hrs) Example 1 3.31 34.2 349 Example 2 3.28 34.5 358 Example 3 3.33 34.9 363 Example 4 3.23 35.3 365 Example 5 3.19 34.8 372 Example 6 3.23 34.0 362 Example 7 3.20 34.7 365 Example 8 3.25 35.1 362 Example 9 3.17 34.3 359 Example 10 3.23 35.0 365 Example 11 3.16 35.3 356 Example 12 3.22 34.1 358 Example 13 3.28 34.3 367 Example 14 3.12 34.5 355 Example 15 3.20 34.4 362 Example 16 3.27 33.6 355 Example 17 3.13 34.0 357 Example 18 3.24 34.6 361 Example 19 3.27 34.7 356 Example 20 3.23 34.2 366 Example 21 3.24 34.6 351 Example 22 3.30 33.8 367 Example 23 3.25 33.4 363 Example 24 3.22 34.8 349 Comparative Example 1 3.60 25.1 151 Comparative Example 2 3.51 25.6 147 Comparative Example 3 3.58 24.9 152 Comparative Example 4 3.55 26.4 146 Comparative Example 5 3.49 29.3 287 Comparative Example 6 3.48 31.4 291 Comparative Example 7 3.87 22.3 143 Comparative Example 8 3.72 23.6 147 Comparative Example 9 3.53 25.5 150 Comparative Example 10 3.59 24.8 148 Comparative Example 11 4.21 17.1 62 Comparative Example 12 4.24 16.6 58 Comparative Example 13 4.27 16.5 60 Comparative Example 14 4.21 17.1 66

[0327] This invention selects dibenzofuran and similar structures with 1 / 2 / 3 substitution positions as substituents for the triazine group. Compared with the prior art structure using dibenzofuran and similar structures with 4-position substituents for the triazine group, this avoids the complexation of the compound with metal ions of the dopant material, thereby effectively improving the luminous efficiency and extending the luminous lifetime of the device. Simultaneously, the greater distance between the 1 / 2 / 3 substitution positions of dibenzofuran and similar structures and the triazine group also improves the flexibility of the molecule, which is more conducive to electron conduction, further enhancing the device efficiency.

[0328] 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 compound characterized in that, having the structure of formula (1) as follows: wherein, Ar is selected from substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, substituted or unsubstituted C6-C60 aryloxy; R 2 is L 2 Ar 2 wherein Ar 2 is selected from substituted or unsubstituted A groups having the following structure: L 2 is selected from a direct bond, substituted or unsubstituted C6-C60 arylene, substituted or unsubstituted C3-C60 heteroarylene; In formulae A-1 to A-3, "-*" is a connecting bond, X is selected from S, O, NR or CR c1 R c2 ; R", R, R 1 , R c1 , R c2 each independently is selected from hydrogen, deuterium, halogen, cyano, hydroxyl, nitro, amidino, hydrazino, substituted or unsubstituted C1-C60alkyl, substituted or unsubstituted C2-C60alkenyl, substituted or unsubstituted C2-C60alkynyl, substituted or unsubstituted C3-C60cycloalkyl, substituted or unsubstituted C1-C60heterocycloalkyl, substituted or unsubstituted C3-C60cycloalkenyl, substituted or unsubstituted C1-C60heterocycloalkenyl, substituted or unsubstituted C6-C60aryl, substituted or unsubstituted C1-C60heteroaryl; n is an arbitrary integer from 0 to 7; the substituents of the substituted C1-C60 alkyl, substituted C2-C60 alkenyl, substituted C2-C60 alkynyl, substituted C3-C60 cycloalkyl, substituted C1-C60 heterocycloalkyl, substituted C3-C60 cycloalkenyl, substituted C1-C60 heterocycloalkenyl, substituted C6-C60 aryl, substituted C1-C60 heteroaryl, substituted C6-C60 aryloxy, substituted C6-C60 arylene, substituted C3-C60 heteroarylene are selected from one or a combination of the following: deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 arylamine, C3-C60 heteroarylamine.

2. The organic compound according to claim 1, characterized by The organic compound has any one of the structures of formula 1-1 to formula 1-12:

3. The organic compound according to claim 1 or 2, characterized by Ar is selected from substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C3-C20 heteroaryl, substituted or unsubstituted C6-C20 aryloxy; and / or, L 2 is selected from a bond, substituted or unsubstituted C6-C20 arylene, substituted or unsubstituted C3-C20 heteroarylene; and / or, R", R, R 1 , R c1 , R c2 each independently is selected from hydrogen, deuterium, halogen, cyano, hydroxyl, nitro, amidino, hydrazino, substituted or unsubstituted C1-C20alkyl, substituted or unsubstituted C2-C20alkenyl, substituted or unsubstituted C2-C20alkynyl, substituted or unsubstituted C3-C20cycloalkyl, substituted or unsubstituted C1-C20heterocycloalkyl, substituted or unsubstituted C3-C20cycloalkenyl, substituted or unsubstituted C1-C20heterocycloalkenyl, substituted or unsubstituted C6-C20aryl, substituted or unsubstituted C1-C20heteroaryl; wherein, the substituents of the substituted C1-C20 alkyl, substituted C2-C20 alkenyl, substituted C2-C20 alkynyl, substituted C3-C20 cycloalkyl, substituted C1-C20 heterocycloalkyl, substituted C3-C20 cycloalkenyl, substituted C1-C20 heterocycloalkenyl, substituted C6-C20 aryl, substituted C1-C20 heteroaryl, substituted C6-C20 aryloxy, substituted C6-C20 arylene, substituted C3-C20 heteroarylene are selected from one or a combination of the following: deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 arylamine, C3-C60 heteroarylamine; Preferably, when the number of R" is greater than or equal to 2, R" can exist individually or adjacent two form a substituted or unsubstituted C3-C60 alicyclic ring, a substituted or unsubstituted C6-C60 aromatic ring; wherein, the substituents of the substituted C3-C60 alicyclic ring, substituted C6-C60 aromatic ring are selected from one or a combination of the following: deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 arylamine, C3-C60 heteroarylamine; Preferably, when the number of R" is greater than or equal to 2, R" can exist individually or adjacent two form a substituted or unsubstituted C3-C30 alicyclic ring, a substituted or unsubstituted C6-C30 aromatic ring; wherein the substituents in the substituted C3-C30 alicyclic ring, the substituted C6-C30 aromatic ring are selected from one or a combination of deuterium, halogen, cyano, C1-C60 alkyl, C3-C60 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 arylamine, C3-C60 heteroarylamine.

4. The organic compound according to any one of claims 1 to 3, characterized by Ar is selected from a substituted or unsubstituted B group, the B group is selected from the following groups: phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, fluoranthene, triphenylene, phenylnaphthyl, naphthylphenyl, binaphthyl, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, benzo dimethylfluorenyl, benzo diphenylfluorenyl, benzo spirobifluorenyl, benzofuranyl, dibenzofuranyl, naphthobenzofuranyl, dinaphthofuranyl, benzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, carbazolyl, phenylcarbazolyl, benzo carbazolyl, benzo phenylcarbazolyl, dibenzo carbazolyl, biphenylcarbazolyl, phenanthrobenzofuranyl, benzofurobenzofuranyl, dibenzofurobenzofuranyl, phenylcarbazolobenzofuranyl; the substituents in the substituted B group are selected from one or a combination of deuterium, halogen, cyano, C1-C30 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 arylamine, C3-C60 heteroarylamine; and / or, R", R, R 1 , R c1 , R c2 each independently selected from a substituted or unsubstituted C group selected from the group consisting of: methyl, ethyl, n-propyl, i-propyl, n-butyl, n-hexyl, n-octyl, i-butyl, t-butyl, ethenyl, propenyl, butenyl, ethynyl, propynyl, butynyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, fluoranthenyl, triphenylenyl, phenylnaphthyl, naphthylphenyl, binaphthyl, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, benzo dimethylfluorenyl, benzo diphenylfluorenyl, benzo spirobifluorenyl, benzofuranyl, dibenzofuranyl, naphthobenzofuranyl, dinaphthofuranyl, benzothienyl, dibenzothienyl, naphthobenzothienyl, carbazolyl, phenylcarbazolyl, benzocarbazolyl, benzo phenylcarbazolyl, dibenzocarbazolyl, biphenylcarbazolyl, phenanthrobenzofuranyl, dibenzofuranobenzofuranyl, benzofuranobenzofuranyl, phenylcarbazolobenzofuranyl; the substituents in the substituted C group are selected from one or a combination of deuterium, halogen, cyano, C1-C30 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 arylamine, C3-C60 heteroarylamine; Preferably, when the number of R” is greater than or equal to 2, R” can exist individually or two adjacent R” form a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted anthracene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted biphenyl ring, a substituted or unsubstituted fluorene ring, a substituted or unsubstituted spirobifluorene ring, a substituted or unsubstituted dimethylfluorene ring, a substituted or unsubstituted pyrene ring; wherein the substituents in the substituted naphthalene ring, the substituted benzene ring, the substituted anthracene ring, the substituted phenanthrene ring, the substituted biphenyl ring, the substituted fluorene ring, the substituted spirofluorene ring, the substituted dimethylfluorene ring, the substituted pyrene ring are selected from one or a combination of deuterium, halogen, cyano, C1-C30 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 arylamine, C3-C60 heteroarylamine; Preferably, when the number of R” is greater than or equal to 2, R” can exist individually or two adjacent R” form a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted anthracene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted biphenyl ring, a substituted or unsubstituted fluorene ring, a substituted or unsubstituted spirobifluorene ring, a substituted or unsubstituted dimethylfluorene ring, a substituted or unsubstituted pyrene ring; Preferably, when the number of R” is greater than or equal to 2, R” can exist individually or two adjacent R” form a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted anthracene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted biphenyl ring, a substituted or unsubstituted fluorene ring, a substituted or unsubstituted spirobifluorene ring, a substituted or unsubstituted dimethylfluorene ring, a substituted or unsubstituted pyrene ring; The substituents in the substituted naphthalene ring, the substituted benzene ring, the substituted anthracene ring, the substituted phenanthrene ring, the substituted biphenyl ring, the substituted fluorene ring, the substituted spirofluorene ring, the substituted dimethylfluorene ring, and the substituted pyrene ring are selected from deuterium, halogen, cyano, methyl, ethyl, propyl, adamantyl, cyclopropane, cyclohexane, cyclopentane, phenyl, naphthyl, biphenyl, anthracene, fluorene, pyrene, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, carbazole.

5. The organic compound according to any one of claims 1 to 4, characterized by Ar is selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, and substituted or unsubstituted naphthyl; and / or, R", R, R 1 , R c1 , R c2 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenyl naphthyl, substituted or unsubstituted naphthyl phenyl; The substituents in the substituted phenyl, the substituted biphenyl, the substituted naphthyl, the substituted phenyl naphthyl, and the substituted naphthyl phenyl are selected from deuterium, halogen, cyano, C1-C30 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 arylamine, and C3-C60 heteroarylamine, or a combination of one or two thereof; Preferably, Ar is selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, and substituted or unsubstituted naphthyl; and / or, R", R, R 1 , R c1 , R c2 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenyl naphthyl, substituted or unsubstituted naphthyl phenyl; The substituents in the substituted phenyl, the substituted biphenyl, the substituted naphthyl, the substituted phenyl naphthyl, and the substituted naphthyl phenyl are selected from deuterium, halogen, cyano, methyl, ethyl, propyl, adamantyl, cyclopropane, cyclohexane, cyclopentane, phenyl, naphthyl, biphenyl, anthracene, fluorene, pyrene, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, and carbazole.

6. The organic compound according to any one of claims 1 to 5, characterized by The organic compound is selected from one of the following structures:

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

8. The organic electroluminescent material according to claim 7, characterized in that The organic electroluminescent material further comprises an organic compound represented by formula (2), In formula (2), Ar 3 , Ar 4 each independently is selected from substituted or unsubstituted C6-C30aryl, substituted or unsubstituted C3-C30heteroaryl; wherein the substituents in the substituted C6-C30 aryl and the substituted C3-C30 heteroaryl are each independently selected from deuterium, halogen, cyano, C1-C30 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 arylamine, and C3-C60 heteroarylamine, or a combination of one or two thereof; Preferably, Ar 3 , Ar 4 each independently is selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthryl; wherein the substituents in the substituted phenyl, the substituted biphenyl, the substituted naphthyl, the substituted dibenzofuran, the substituted dibenzothiophene, the substituted terphenyl, and the substituted phenanthryl are selected from deuterium, halogen, cyano, C1-C30 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 arylamine, and C3-C60 heteroarylamine, or a combination of one or two thereof; Preferably, Ar 3 is selected from the group consisting of dibenzofuranyl, phenyldibenzofuranyl, dibenzothiophenyl, phenyldibenzothiophenyl, benzonaphtofuranyl, benzonaphtothiophenyl; Ar 4 is selected from the group consisting of phenyl, biphenyl, terphenyl, phenanthryl, naphthyl, phenylnaphthyl, naphthylphenyl.

9. The organic electroluminescent material according to claim 7 or 8, characterized in that The organic compound represented by formula (2) is selected from any one of N-1 to N-15:

10. The organic electroluminescent material according to any one of claims 7 to 9, characterized in that In the organic electroluminescent material, the mass ratio of the compound represented by formula (1) to the compound represented by formula (2) is 1:9-9:1; Preferably, in the organic electroluminescent material, the mass ratio of the compound represented by formula (1) to the compound represented by formula (2) is 2:8-8:2; More preferably, in the organic electroluminescent material, the mass ratio of the compound represented by formula (1) to the compound represented by formula (2) is 3:7-7:3; Further preferably, in the organic electroluminescent material, the mass ratio of the compound represented by formula (1) to the compound represented by formula (2) is 4:6-6:

4.

11. An organic electroluminescent device, characterized by comprising The organic electroluminescent device comprises an anode, a cathode, and an organic layer between the anode and the cathode, and the organic layer comprises the organic compound according to any one of claims 1-6 or the organic electroluminescent material according to any one of claims 7-10.

12. The organic electroluminescent device according to claim 11, characterized in that, The organic layer comprises a light-emitting layer, and the light-emitting layer comprises the organic compound according to any one of claims 1-6 or the organic electroluminescent material according to any one of claims 7-10. Preferably, the light-emitting layer comprises a host material and a guest material, and the host material comprises the organic compound according to any one of claims 1-6 or the organic electroluminescent material according to any one of claims 7-10.

13. An electronic device, comprising: The electronic device comprises the organic electroluminescent device according to claim 11 or 12.

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