Nitrogen-containing heterocyclic compound as well as preparation method and application thereof

Abstract

The invention belongs to the technical field of organic electroluminescence, and particularly relates to a nitrogen-containing heterocyclic compound and a preparation method and application thereof. The nitrogen-containing heterocyclic compound has a structure as shown in a formula 1. According to the nitrogen-containing heterocyclic compound provided by the invention, through structural design and group limitation, the carrier mobility of the nitrogen-containing heterocyclic compound is relatively excellent, so that the organic electroluminescent device prepared from the nitrogen-containing heterocyclic compound has better device performance. Formula 1

Description

Technical Field

[0001] This invention belongs to the field of organic electroluminescence technology, specifically relating to a nitrogen-containing heterocyclic compound, its preparation method, and its application. Background Technology

[0002] Organic electroluminescent devices (OELDs) are a light-emitting technology based on organic semiconductor materials. Their core operating mechanism relies on a precise stacked structure consisting of an anode, multiple organic functional layers, and a cathode. Driven by an external electric field, charge carriers (holes and electrons) are injected into the device from the anode and cathode, respectively. They are then directionally transported through specific organic functional layers and finally converge at the emissive layer. Within the emissive layer, holes and electrons recombine to form excited excitons. When these excitons relax from the excited state to the ground state, they release energy in the form of light radiation, thus achieving efficient electroluminescence. Due to its advantages such as ultra-thin flexibility, high contrast, wide color gamut, low driving voltage, and scalability, as well as its potential for large-area film deposition, OELD technology is widely considered to have enormous application value and broad development prospects in cutting-edge fields such as flexible display devices, transparent display interfaces, and next-generation high-efficiency solid-state lighting solutions.

[0003] However, the poor performance of existing organic electroluminescent materials leads to an imbalance in carrier mobility, which in turn results in high driving voltage, low luminous efficiency, and short lifetime for organic electroluminescent devices containing these materials, severely limiting their application.

[0004] Therefore, developing a new organic electroluminescent material is of great significance. Summary of the Invention

[0005] The technical problem to be solved by the present invention is that the performance of organic electroluminescent materials in the prior art is poor, which leads to an imbalance in carrier mobility. As a result, organic electroluminescent devices containing such organic electroluminescent materials have problems such as high driving voltage, low luminous efficiency and short luminous lifetime. The present invention provides a nitrogen-containing heterocyclic compound, its preparation method and application.

[0006] In this invention, the term "substituent" has its usual meaning as known in the art, referring to a chemical moiety covalently attached to or, where appropriate, fused to a parent nucleus group.

[0007] In this invention, 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.

[0008] In this invention, " " indicates a link key.

[0009] In this invention, the term "halogen" refers to an atom selected from fluorine, chlorine, bromine, and iodine.

[0010] In this invention, 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 30 carbon atoms. Examples of such substituents include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl.

[0011] In this invention, the term "cycloalkyl" refers to a cyclic alkyl group consisting of at least 3 atoms, and more specifically, it refers to a monocyclic or polycyclic hydrocarbon derived from a main chain of 3 to 12 carbon atoms, preferably 3 to 6 carbon atoms. Of course, the cycloalkyl group includes, but is not limited to, cyclopropyl, cyclobutyl, adamantyl, etc.

[0012] In this invention, 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 spiro structures. Aryl groups include, but are not limited to, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracene, fluorenyl, spirodifluorenyl, etc., and arylene groups include, but are not limited to, etc., wherein arylene refers to a divalent or polyvalent group formed by the further loss of one or more hydrogen atoms from an aryl group.

[0013] In this invention, 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, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiopheneyl, isobenzofuranyl, dibenzofuranyl, dibenzothiopheneyl, benzimidazolyl, and benzo[[...]] Thiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazole, benzothiadiazolyl, quinolinyl, isoquinolinyl, cenolinyl, quinazolinyl, quinoxalinyl, carbazole, phenoxazinyl, phenthiazinyl, phenanthidyl, benzo[m]dioxacyclopentenyl, dihydroacridyl, and their derivatives; heteroaryl groups include, but are not limited to, furanyl, phenylthio, and pyridyl. Pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzimidazoleyl The following groups are included: benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, ininzolyl, benzothiadiazolyl, quinolinyl, isoquinolinyl, cenolinyl, quinazolinyl, quinoxolinyl, carbazolyl, phenoxazinyl, phenthiazinyl, phenanthridineyl, benzom-dioxacyclopentenyl, dihydroacridyl, and their derivatives. As used herein, the term "substituted" refers to a compound in which a hydrogen atom is substituted by another substituent. This position is not limited to a specific position, as long as the hydrogen at that position can be substituted by a substituent. When two or more substituents are present, the two or more substituents may be the same or different.

[0014] In this invention, "C1-C15, C3-C60, C6-C60" defines the range of carbon atoms, indicating that the number of carbon atoms is any integer within the defined range. For example, C6-C60 aryl means that the number of carbon atoms in the aryl group can be any integer within the range of 6-60, such as 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60.

[0015] In this invention, unless otherwise specified, the substituents do not fuse with the group to which they belong.

[0016] In this invention, if the group is not specified as substituted or unsubstituted, it means that it has not been substituted.

[0017] In this invention, the term "organic electroluminescent material" refers to a material that can be used in organic electroluminescent devices 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.

[0018] To solve the above-mentioned technical problems, the present invention adopts the following technical solution:

[0019] A first aspect of the present invention provides a nitrogen-containing heterocyclic compound having the structure shown in Formula 1:

[0020]

[0021] Formula 1

[0022] In Formula 1, L is selected from single bond, substituted or unsubstituted C6-C60 arylene, substituted or unsubstituted C3-C60 heteroarylene; Ar is selected from substituted or unsubstituted C3-C60 heteroarylene containing N atom.

[0023] In the substituted C6-C60 arylene, substituted C3-C60 heteroarylene, and substituted C3-C60 heteroarylene containing an N atom, the substituents are selected from one or a combination of at least two of deuterium, halogen, cyano, hydroxyl, carbonyl, nitro, C1-C15 alkyl, C6-C60 aryl, and C3-C60 heteroarylene.

[0024] Preferably, L is selected from single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C3-C30 heteroarylene; Ar is selected from substituted or unsubstituted C3-C30 heteroarylene containing N atom;

[0025] The substituents in the substituted C6-C30 arylene, substituted C3-C30 heteroarylene, and substituted C3-C30 heteroarylene containing an N atom are selected from one or a combination of at least two of deuterium, halogen, cyano, hydroxyl, carbonyl, nitro, C1-C15 alkyl, C6-C30 aryl, and C3-C30 heteroarylene.

[0026] Preferably, L is selected from single-bonded, substituted or unsubstituted C6-C25 arylene, substituted or unsubstituted C3-C25 heteroarylene; Ar is selected from substituted or unsubstituted C3-C25 heteroarylene containing N atoms;

[0027] The substituents in the substituted C6-C25 arylene, substituted C3-C25 heteroarylene, and substituted C3-C25 heteroarylene containing N atoms are selected from one or a combination of at least two of deuterium, halogen, cyano, hydroxyl, carbonyl, nitro, C1-C15 alkyl, C6-C25 aryl, and C3-C25 heteroarylene.

[0028] Preferably, L is selected from single-bonded, substituted or unsubstituted C6-C20 arylene, substituted or unsubstituted C3-C20 heteroarylene; Ar is selected from substituted or unsubstituted C3-C20 heteroarylene containing N atoms;

[0029] The substituents in the substituted C6-C20 arylene, substituted C3-C20 heteroarylene, and substituted C3-C20 heteroarylene containing an N atom are selected from one or a combination of at least two of deuterium, halogen, cyano, hydroxyl, carbonyl, nitro, C1-C15 alkyl, C6-C20 aryl, and C3-C20 heteroarylene.

[0030] Preferably, L is selected from single bond, substituted or unsubstituted C6-C15 arylene, substituted or unsubstituted C3-C15 heteroarylene; Ar is selected from substituted or unsubstituted C3-C15 heteroarylene containing N atom;

[0031] The substituents in the substituted C6-C15 arylene, substituted C3-C15 heteroarylene, and substituted C3-C15 heteroarylene containing an N atom are selected from one or a combination of at least two of deuterium, halogen, cyano, hydroxyl, carbonyl, nitro, C1-C15 alkyl, C6-C15 aryl, and C3-C15 heteroarylene.

[0032] Preferably, L is selected from single bond, substituted or unsubstituted C6-C12 arylene, substituted or unsubstituted C3-C12 heteroarylene; Ar is selected from substituted or unsubstituted C3-C12 heteroarylene containing N atom;

[0033] The substituents in the substituted C6-C12 arylene, substituted C3-C12 heteroarylene, and substituted C3-C12 heteroarylene containing an N atom are selected from one or a combination of at least two of deuterium, halogen, cyano, hydroxyl, carbonyl, nitro, C1-C15 alkyl, C6-C12 aryl, and C3-C12 heteroarylene.

[0034] Preferably, L is selected from a single bond, a substituted or unsubstituted A group; the A group is selected from phenylene, naphthylene, pyridinylene, pyrimidinylene, quinolinylene, isoquinolinylene, quinazolinylene, quinoxalinylene, naphthidylene, pyridopyrimidinylene, and pyrimidopyrimidinylene.

[0035] Wherein, the substituents in the substituted A group are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, hydroxyl, carbonyl, nitro, methyl, ethyl, n-propyl, isopropyl, tert-butyl, sec-butyl, tert-butyl, phenyl, naphthyl, phenanthryl, biphenyl, binatyl, phenylnaphthyl, naphthylphenyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl, naphthidyl, pyridopyrimidinyl, pyrimidopyrimidinyl, dibenzofuranyl, and dibenzothiopheneyl.

[0036] In some embodiments of the present invention, L is selected from any one of single bond, phenylene, naphthylene, pyridylene, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthylene, pyridopyrimidinyl, and pyrimidopyrimidinyl.

[0037] In some embodiments of the present invention, L is selected from any one of single bond, phenylene, naphthylene, and pyridylene.

[0038] Preferably, Ar is selected from the structure shown in Formula 2 below:

[0039]

[0040] Formula 2

[0041] In Equation 2, " " indicates a link key with L; X1 represents N or CR1, X2 represents N or CR2, X3 represents N or CR3, X4 represents N or CR4, X5 represents N or CR5, and at least one of X1-X5 is selected from N;

[0042] Optionally, one of X1-X5 is selected from N;

[0043] Optionally, both X1-X5 are selected from N;

[0044] Optionally, three of X1-X5 are selected from N;

[0045] Optionally, four of X1-X5 are selected from N;

[0046] Optionally, all of X1-X5 are selected from N.

[0047] R1-R5 are each independently selected from substituted or unsubstituted C6-C60 aryl groups, substituted or unsubstituted C3-C60 heteroaryl groups, or adjacent R1-R5 groups are bonded together to form substituted or unsubstituted C6-C60 aromatic rings or substituted or unsubstituted C3-C60 heteroaryl rings.

[0048] The substituents in the substituted C6-C60 aryl, substituted C3-C60 heteroaryl, substituted C6-C60 aromatic ring, and substituted C3-C60 heteroaryl ring are selected from one or a combination of at least two of deuterium, halogen, cyano, hydroxyl, carbonyl, nitro, C1-C15 alkyl, C6-C60 aryl, and C3-C60 heteroaryl.

[0049] Preferably, the substituents in the substituted C6-C60 aryl, substituted C3-C60 heteroaryl, substituted C6-C60 aromatic ring, and substituted C3-C60 heteroaryl ring are selected from deuterium, halogen, cyano, hydroxyl, carbonyl, nitro, methyl, ethyl, n-propyl, isopropyl, tert-butyl, sec-butyl, tert-butyl, phenyl, naphthyl, phenanthryl, biphenyl, binatyl, phenylnaphthyl, naphthylphenyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, pyridopyrimidinyl, pyrimidopyrimidinyl, dibenzofuranyl, and dibenzothiopheneyl are selected from one or a combination of at least two of these groups.

[0050] Preferably, Ar is selected from any one of the structures shown in formulas 2-1 to 2-12 below:

[0051]

[0052] In Equations 2-1 to 2-12, " " indicates a linking bond with L; R' indicates a hydrogen, deuterium, substituted or unsubstituted B group;

[0053] Wherein, group B is selected from phenyl, naphthyl, phenanthryl, biphenyl, binatyl, phenylnaphthyl, naphthylphenyl, triphenylene, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, pyridopyrimidinyl, pyrimidopyrimidinyl, dibenzofuranyl, dibenzothiopheneyl, N-phenylcarbazoyl, carbazoyl, phenylpyrimidinyl, phenylpyridinyl, pyrimidinylphenyl, pyridinylphenyl; the substituents in the substituted group B are selected from one or a combination of at least two of deuterium, halogen, cyano, hydroxyl, carbonyl, nitro, C1-C15 alkyl, C6-C60 aryl, and C3-C60 heteroaryl.

[0054] Preferably, the substituents in the substituted B group are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, hydroxyl, carbonyl, nitro, methyl, ethyl, n-propyl, isopropyl, tert-butyl, sec-butyl, tert-butyl, phenyl, naphthyl, phenanthryl, biphenyl, binatyl, phenylnaphthyl, naphthylphenyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, pyridopyrimidinyl, pyrimidopyrimidinyl, dibenzofuranyl, and dibenzothiopheneyl.

[0055] Preferably, Ar is selected from any one of the structures shown in formulas 3-1 to 3-20 below:

[0056]

[0057] In equations 3-1 to 3-20, " " indicates a linking bond with L; R' indicates a hydrogen, deuterium, substituted or unsubstituted B group;

[0058] Wherein, the B group is selected from phenyl, naphthyl, phenanthryl, biphenyl, binaphthyl, phenylnaphthyl, naphthylphenyl, triphenylene, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, pyridopyrimidinyl, pyrimidopyrimidinyl, dibenzofuranyl, dibenzothiophenyl, N-phenylcarbazoyl, carbazoyl, phenylpyrimidinyl, phenylpyridinyl, pyrimidinylphenyl, pyridinylphenyl;

[0059] The substituents in the substituted B group are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, hydroxyl, carbonyl, nitro, C1-C15 alkyl, C6-C60 aryl, and C3-C60 heteroaryl.

[0060] Preferably, the substituents in the substituted B group are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, hydroxyl, carbonyl, nitro, methyl, ethyl, n-propyl, isopropyl, tert-butyl, sec-butyl, tert-butyl, phenyl, naphthyl, phenanthryl, biphenyl, binatyl, phenylnaphthyl, naphthylphenyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, pyridopyrimidinyl, pyrimidopyrimidinyl, dibenzofuranyl, and dibenzothiopheneyl.

[0061] In some embodiments of the present invention, in formulas 3-1 to 3-20, " " indicates a linking bond with L; R' indicates one or a combination of at least two of the following: hydrogen, deuterium, phenyl, naphthyl, phenanthrene, biphenyl, binatyl, phenylnaphthyl, naphthylphenyl, triphenylene, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, pyridinylpyrimidinyl, pyrimidinylpyrimidinyl, dibenzofuranyl, dibenzothiopheneyl, N-phenylcarbazoyl, carbazoyl, phenylpyrimidinyl, phenylpyridinyl, pyrimidinylphenyl, and pyridinylphenyl.

[0062] Preferably, the nitrogen-containing heterocyclic compound is selected from any one of the structures M1 to M84:

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083] .

[0084] A second aspect of this invention provides a method for synthesizing nitrogen-containing heterocyclic compounds, comprising the following synthetic route:

[0085] Wherein, X is Cl-L-Ar; L and Ar are completely consistent with the definitions of L and Ar disclosed in the nitrogen-containing heterocyclic compounds provided in Part I of this invention.

[0086] A third aspect of the present invention provides an organic electroluminescent material, wherein the organic electroluminescent material includes the nitrogen-containing heterocyclic compound provided in the first aspect of the present invention.

[0087] A fourth aspect of the present invention 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 containing a nitrogen-containing heterocyclic compound provided in the first aspect of the present invention and / or an organic electroluminescent material provided in the third aspect of the present invention.

[0088] The organic layer includes any one or a combination of at least two of the following: a light-emitting layer, a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a hole blocking layer, an electron transport layer, and an electron injection layer.

[0089] Optionally, the organic layer includes a light-emitting layer, which includes a nitrogen-containing heterocyclic compound provided in the first aspect of the present invention and / or an organic electroluminescent material provided in the third aspect of the present invention.

[0090] Preferably, the luminescent layer comprises a host material and a guest material. The host material includes nitrogen-containing heterocyclic compounds and their derivatives, triazine compounds and their derivatives, or other materials as described above. The guest material can be a compound with a condensed aryl ring or its derivative, a compound with a heteroaryl ring or its derivative, an aromatic amine derivative, or other materials. This application does not impose any special limitations on this. The guest material is also called a dopant or dopant. According to the luminescence type, it can be divided into fluorescent dopant and phosphorescent dopant.

[0091] Optionally, the organic layer includes a hole injection layer to enhance the ability to inject holes into the hole transport layer; the hole injection layer may be selected from benzidine derivatives, arylamine compounds, phthalocyanine derivatives or other materials, and this application does not impose any special restrictions on this.

[0092] Optionally, the organic layer includes a hole transport layer, which may include one or more hole transport materials. The hole transport materials may be selected from carbazole polymers, carbazole-linked tri-nitrogen heterocyclic compounds, or other types of compounds. This application does not impose any special restrictions on this.

[0093] Optionally, the organic layer includes a light-emitting auxiliary layer, which can be a single-layer or multi-layer structure, and the light-emitting auxiliary layer includes nitrogen-containing heterocyclic compounds, carbazole compounds and their derivatives, or other materials.

[0094] Optionally, the organic layer includes a hole-blocking layer, which can be a single-layer or multi-layer structure.

[0095] Optionally, the organic layer includes an electron transport layer, which can be a single-layer structure or a multi-layer structure. It can include one or more electron transport materials, which can be selected from, but are not limited to, LiQ, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives or other electron transport materials. This application does not make any special limitation in this regard.

[0096] Optionally, an electron injection layer is provided between the cathode and the electron transport layer to enhance the ability to inject electrons into the electron transport layer. The electron injection layer may include inorganic materials such as alkali metal sulfides and alkali metal halides, or it may include complexes of alkali metals and organic compounds.

[0097] Optionally, the organic electroluminescent device is fabricated by inkjet printing;

[0098] Optionally, the organic electroluminescent device is fabricated by vapor deposition.

[0099] Optionally, the organic electroluminescent device includes a white light organic electroluminescent device;

[0100] Optionally, the organic electroluminescent device includes a red-light organic electroluminescent device;

[0101] Optionally, the organic electroluminescent device includes a blue organic electroluminescent device;

[0102] Optionally, the organic electroluminescent device includes a green organic electroluminescent device;

[0103] Optionally, the organic electroluminescent device includes a yellow light organic electroluminescent device.

[0104] The fifth aspect of the present invention provides an electronic device comprising any one or a combination of at least two of the nitrogen-containing heterocyclic compound provided in the first aspect of the present invention, the organic electroluminescent material provided in the third aspect of the present invention, and the organic electroluminescent device provided in the fourth aspect of the present invention.

[0105] The electronic device is applied to, but is not limited to, any of the following fields:

[0106] The field includes fiber optic devices, lighting devices, electrophotographic photosensitive devices, photoelectric converters, organic solar cells, switching devices, organic light-emitting field-effect transistors, image sensors, and dye lasers.

[0107] Beneficial effects:

[0108] The organic compound provided by this invention, based on the structure of Formula 1, introduces specific groups at specific sites, which is beneficial for regulating the exciton recombination energy level in the molecular aggregated state, while effectively controlling the triplet energy level. This results in a high degree of matching between the HOMO and LUMO energy levels of the organic compound and adjacent energy levels, thus facilitating the regulation of the exciton recombination energy level in the molecular aggregated state and effectively controlling the triplet energy level. This also results in a high degree of matching between the HOMO and LUMO energy levels of the organic compound and adjacent energy levels, leading to a more balanced carrier mobility in the organic compound. Consequently, the organic electroluminescent device containing this organic compound exhibits a lower driving voltage, higher luminous efficiency, and longer lifetime. Attached Figure Description

[0109] The present invention will be further described in detail below with reference to the accompanying drawings, and the advantages of the present invention in the above and / or other aspects will become clearer.

[0110] Figure 1 The image shows the 1H NMR spectrum of compound M1 prepared in Example 1 of this invention.

[0111] Figure 2 This is the ultraviolet absorption spectrum of compound M1 in toluene solution in Example 1 of the present invention.

[0112] Figure 3 This is the fluorescence emission spectrum of compound M1 in toluene solution in Example 1 of the present invention.

[0113] Figure 4 This is a schematic diagram of the structure of an OLED light-emitting device in an application example of the present invention. Detailed Implementation

[0114] The present invention will be further described in detail below with reference to specific embodiments, and the advantages of the present invention in the above and / or other aspects will become clearer.

[0115] Unless otherwise specified, the experimental methods described in the following examples are conventional methods; unless otherwise specified, the reagents and materials are commercially available.

[0116] Example 1:

[0117] This embodiment provides a nitrogen-containing heterocyclic compound M1, with the following specific chemical formula:

[0118]

[0119] M1

[0120] The synthesis route for M1 is shown below:

[0121]

[0122] The specific preparation steps are as follows:

[0123] (1) Preparation of intermediate M1-1

[0124] Under nitrogen protection, in a 2L four-necked flask, the starting material M1-a (250mmol) was dissolved in 500mL of tetrahydrofuran. The solution was stirred and cooled to 0°C. NBS (300mmol) was added in portions and stirred overnight at room temperature to quench the reaction. After extraction, the intermediate M1-1 was obtained by column chromatography (yield 80%).

[0125] (2) Preparation of intermediate M1-2

[0126] Under nitrogen protection, in a 2L four-necked flask, compound M1-1 (217 mmol), starting material M1-b (240 mmol), Pd132 (6.5 mmol), and potassium carbonate (434 mmol) were dissolved in 600 mL of toluene at room temperature. The reaction was quenched by reflux and stirring at 120 °C for 3 hours. After extraction with dichloromethane, the intermediate M1-2 was obtained by column chromatography (yield 80%).

[0127] (3) Preparation of intermediate M1-3

[0128] Under nitrogen protection, in a 2L four-necked flask, compound M1-2 (160 mmol), starting material M1-c (180 mmol), Pd2(dba)3 (4.8 mmol), X-Phos (8 mmol), and sodium tert-butoxide (320 mmol) were dissolved in 500 mL of toluene at room temperature. The reaction was quenched by reflux and stirring at 120 °C for 6 hours. After extraction with dichloromethane, compound M1-3 was obtained by column chromatography (70% yield).

[0129] (4) Preparation of intermediate M1-4

[0130] Under nitrogen protection, in a 1L four-necked flask, compound M1-3 (110 mmol) and boron tribromide (180 mmol) were dissolved in 500 mL toluene at room temperature. The reaction was quenched by stirring under reflux at 120 °C for 2 hours. After extraction with dichloromethane, compound M1-4 was obtained by column chromatography (yield 80%).

[0131] (5) Preparation of intermediate M1-5

[0132] Under nitrogen protection, compound M1-4 (90 mmol) was dissolved in 500 mL of dichloromethane in a 1 L four-necked flask at -20 °C. Triethylamine (180 mmol) was added dropwise, followed by the addition of trifluoromethanesulfonic anhydride (110 mmol). The reaction was quenched after stirring at room temperature for 1 hour. After extraction with dichloromethane, compound M1-5 was obtained by column chromatography (75% yield).

[0133] (6) Preparation of intermediate M1-6

[0134] Under nitrogen protection, in a 1L four-necked flask, compound M1-5 (60 mmol), starting material M1-d (70 mmol), Pd2(dba)3 (1.8 mmol), and potassium carbonate (120 mmol) were dissolved in 400 mL of toluene at room temperature. The reaction was quenched by reflux and stirring at 120 °C for 3 hours. After extraction with dichloromethane, compound M1-6 was obtained by column chromatography (yield 80%).

[0135] (7) Preparation of intermediate M1-7

[0136] Under nitrogen protection, in a 1L four-necked flask, compound M1-6 (44 mmol), palladium acetate (1.3 mmol), BrettPhos (2.2 mmol), and sodium tert-butoxide (88 mmol) were dissolved in 300 mL xylene at room temperature. The reaction was quenched by reflux and stirring at 150 °C for 3 hours. After extraction with dichloromethane, the solution was purified by column chromatography to obtain compound M1-7 (60% yield).

[0137] (8) Preparation of intermediate M1-8

[0138] Under nitrogen protection, in a 500 mL four-necked flask, compound M1-7 (25 mmol), starting material M1-d (30 mmol), and cesium carbonate (50 mmol) were dissolved in 200 mL DMF at room temperature. The reaction was quenched by stirring under reflux at 150 °C for 6 hours. After extraction with dichloromethane, the mixture was subjected to column chromatography to obtain compound M1-8 (90% yield).

[0139] (9) Preparation of compound M1

[0140] Under nitrogen protection, in a 500 mL four-necked flask, compound M1-8 (18 mmol), palladium acetate (0.54 mmol), triphenylphosphine (0.1 mmol), and cesium carbonate (36 mmol) were dissolved in 150 mL DMF at room temperature. The reaction was quenched by stirring under reflux at 150 °C overnight. After extraction with dichloromethane, compound M1 was obtained by column chromatography (60% yield).

[0141] The structure of compound M1 was characterized. Figure 1 The 1H NMR spectrum of compound M1 is shown below. The NMR data are as follows: 1H NMR(500 MHz, Chloroform-d) δ 8.28 (s, 1H), 8.24 (d, J = 7.3 Hz, 1H), 8.20 – 8.17(m, 3H), 8.08 (dd, J = 6.0, 3.5 Hz, 2H), 7.72 – 7.68 (m, 5H), 7.65 – 7.62 (m,4H), 7.59 (s, 1H), 7.56 – 7.52 (m, 2H), 7.47 – 7.28 (m, 11H). Depend on Figure 1 As can be seen from the NMR data, the hydrogen NMR spectrum data corresponds highly with and is reasonable to the basic characteristics of the M1 structure.

[0142] Example 2:

[0143] This embodiment provides a nitrogen-containing heterocyclic compound M2, with the following specific chemical formula:

[0144]

[0145] M2

[0146] The synthesis steps of compound M2 are similar to those of compound M1 in Example 1. The main difference lies in the differences between intermediates M2-2 and M2-3. The synthetic route of intermediate M2-3 is as follows:

[0147]

[0148] The specific steps for synthesizing intermediate M2-3 are as follows: Under nitrogen protection, in a 2L four-necked flask, compound M2-2 (120mmol), starting material M2-c (140mmol), Pd132 (3mmol), X-Phos (7mmol), and sodium tert-butoxide (240mmol) were dissolved in 400mL toluene at room temperature. The reaction was quenched after reflux and stirring at 120℃ for 8 hours. After extraction with dichloromethane, compound M2-3 was obtained by column chromatography (yield 60%).

[0149] Other preparation steps remain unchanged, and compound M2 is obtained accordingly. The structure of compound M2 is characterized, and the NMR data are as follows: 1H NMR (500 MHz, Chloroform-d) δ 8.40 (t, J = 1.8 Hz, 1H), 8.34 (s, 1H), 8.31 – 8.23 ​​(m, 1H), 8.22 – 8.16 (m, 2H), 8.12 – 8.06 (m, 1H), 8.06 – 8.01(m, 3H), 7.94 – 7.85 (m, 2H), 7.74 – 7.67 (m, 2H), 7.66 – 7.48 (m, 9H), 7.45(ddd, J = 7.4, 6.2, 1.2 Hz, 1H), 7.39 – 7.28 (m, 5H). The NMR data show that the hydrogen NMR spectrum data corresponds highly with and is reasonable to the basic characteristics of the M2 structure.

[0150] Example 3:

[0151] This embodiment provides a nitrogen-containing heterocyclic compound M3, with the following specific chemical formula:

[0152]

[0153] M3

[0154] The synthesis steps of compound M3 are similar to those of compound M1 in Example 1. The main difference lies in the differences between intermediates M3-2 and M3-3. The synthetic route of intermediate M3-3 is as follows:

[0155]

[0156] The specific steps for synthesizing intermediate M3-3 are as follows: Under nitrogen protection, in a 2L four-necked flask, compound M3-2 (130mmol), starting material M3-c (160mmol), Pd2(dba)3 (4mmol), S-Phos (8mmol), and sodium tert-butoxide (260mmol) were dissolved in 400mL toluene at room temperature. The reaction was quenched after reflux and stirring at 120℃ for 5 hours. After extraction with dichloromethane, compound M3-3 was obtained by column chromatography (yield 80%).

[0157] Other preparation steps remained unchanged, and compound M3 was obtained. The structure of compound M3 was characterized, and the NMR data are as follows: 1H NMR (500 MHz, Chloroform-d) δ 8.27 (s, 1H), 8.22 – 8.14 (m, 3H), 8.08 (dd, J = 6.2, 3.4 Hz, 2H), 7.97 – 7.91 (m, 2H), 7.79 – 7.74 (m, 2H), 7.74 –7.67 (m, 4H), 7.67 – 7.61 (m, 5H), 7.61 – 7.51 (m, 2H), 7.45 (ddd, J = 7.4,6.3, 1.2 Hz, 1H), 7.43 – 7.37 (m, 3H), 7.37 – 7.31 (m, 3H), 7.31 – 7.27 (m, 2H). The NMR data show that the hydrogen NMR spectrum data corresponds highly with and is consistent with the basic characteristics of the M3 structure.

[0158] Example 4:

[0159] This embodiment provides a nitrogen-containing heterocyclic compound M4, with the following specific chemical formula:

[0160]

[0161] M4

[0162] The synthesis steps of compound M4 are similar to those of compound M1 in Example 1. The main difference lies in the differences between intermediates M4-2 and M4-3. The synthetic route of intermediate M4-3 is as follows:

[0163]

[0164] The specific steps for synthesizing intermediate M4-3 are as follows: Under nitrogen protection, in a 2L four-necked flask, compound M4-2 (140mmol), starting material M4-c (160mmol), Pd2(dba)3 (4.2mmol), S-Phos (8mmol), and sodium tert-butoxide (280mmol) were dissolved in 400mL toluene at room temperature. The reaction was quenched after reflux and stirring at 120℃ for 5 hours. After extraction with dichloromethane, compound M4-3 was obtained by column chromatography (yield 76%).

[0165] Other preparation steps remained unchanged, and compound M4 was obtained. The structure of compound M4 was characterized, and the NMR data are as follows: 11H NMR (500 MHz, Chloroform-d) δ 8.18 (dddd, J = 10.2, 6.6, 2.9, 1.8 Hz, 3H), 8.12 – 8.08 (m, 2H), 8.04 – 7.89 (m, 5H), 7.79 – 7.42 (m, 15H), 7.37 – 7.28 (m, 5H). The NMR data show that this 1H NMR spectrum corresponds highly with and is reasonable for the basic characteristics of the M4 structure.

[0166] Example 5:

[0167] This embodiment provides a nitrogen-containing heterocyclic compound M7, with the following specific chemical formula:

[0168]

[0169] M7

[0170] The synthesis steps of compound M7 are similar to those of compound M1 in Example 1. The main difference lies in the differences between intermediates M7-2 and M7-3. The synthetic route of intermediate M7-3 is as follows:

[0171]

[0172] The specific steps for synthesizing intermediate M7-3 are as follows: Under nitrogen protection, in a 2L four-necked flask, compound M7-2 (120mmol), starting material M7-c (140mmol), Pd132 (4.2mmol), Xant-Phos (6mmol), and sodium tert-butoxide (280mmol) were dissolved in 400mL toluene at room temperature. The reaction was quenched after reflux and stirring at 120℃ for 5 hours. After extraction with dichloromethane, compound M7-3 was obtained by column chromatography (yield 76%).

[0173] Other preparation steps remained unchanged, and compound M7 was obtained. The structure of compound M7 was characterized, and the NMR data are as follows: 11H NMR (500 MHz, Chloroform-d) δ 8.76 (dd, J = 4.6, 1.8 Hz, 1H), 8.32 – 8.25 (m, 2H), 8.22 – 8.16 (m, 2H), 7.96 (dd, J = 7.4, 1.9 Hz, 1H), 7.77 (dd, J = 6.4, 1.6 Hz, 1H), 7.74 – 7.67 (m, 2H), 7.66 – 7.57 (m, 5H), 7.54 (t, J = 7.0 Hz, 1H), 7.49 (s, 1H), 7.48 – 7.28 (m, 9H). The NMR data show that this 1H NMR spectrum highly corresponds to and is reasonable with the basic characteristics of the M7 structure.

[0174] Example 6:

[0175] This embodiment provides a nitrogen-containing heterocyclic compound M8, with the following specific chemical formula:

[0176]

[0177] M8

[0178] The synthesis steps of compound M8 are similar to those of compound M1 in Example 1. The main difference lies in the differences between intermediates M8-2 and M8-3. The synthetic route of intermediate M8-3 is as follows:

[0179]

[0180] The specific steps for synthesizing intermediate M8-3 are as follows: Under nitrogen protection, in a 2L four-necked flask, compound M8-2 (110mmol), starting material M8-c (130mmol), Pd132 (3.5mmol), Xant-Phos (5.5mmol), and sodium tert-butoxide (220mmol) were dissolved in 350mL toluene at room temperature. The reaction was quenched after reflux and stirring at 120℃ for 5 hours. After extraction with dichloromethane, compound M8-3 was obtained by column chromatography (yield 72%).

[0181] Other preparation steps remained unchanged, and compound M8 was obtained. The structure of compound M8 was characterized, and the NMR data are as follows: 11H NMR (500 MHz, Chloroform-d) δ 8.84 (dd, J = 4.9, 2.2 Hz, 1H), 8.35 (dd, J = 9.3, 2.2 Hz, 1H), 8.32 – 8.25 (m, 2H), 8.22 – 8.16 (m, 2H), 7.77 (dd, J = 6.4, 1.6 Hz, 1H), 7.74 – 7.68 (m, 2H), 7.68 – 7.60 (m, 4H), 7.54 (t, J = 7.0 Hz, 1H), 7.51 – 7.28 (m, 11H). The 1H NMR data show a high degree of correspondence and reasonable consistency with the basic characteristics of the M8 structure.

[0182] Example 7:

[0183] This embodiment provides a nitrogen-containing heterocyclic compound M11, with the following specific chemical formula:

[0184]

[0185] M11

[0186] The synthesis steps of compound M11 are similar to those of compound M1 in Example 1. The main difference lies in the differences between intermediates M11-2 and M11-3. The synthetic route of intermediate M11-3 is as follows:

[0187]

[0188] The specific steps for synthesizing intermediate M11-3 are as follows: Under nitrogen protection, in a 2L four-necked flask, compound M11-2 (120mmol), starting material M11-c (140mmol), Pd132 (3.6mmol), S-Phos (5mmol), and sodium tert-butoxide (240mmol) were dissolved in 360mL toluene at room temperature. The reaction was quenched after reflux and stirring at 120℃ for 5 hours. After extraction with dichloromethane, compound M11-3 was obtained by column chromatography (yield 68%).

[0189] Other preparation steps remained unchanged, and compound M11 was obtained. The structure of compound M11 was characterized, and the NMR data are as follows: 11H NMR (500 MHz, Chloroform-d) δ 8.83 – 8.74 (m, 2H), 8.32 – 8.25 (m, 2H), 8.22 – 8.16 (m, 2H), 7.80 – 7.66 (m, 3H), 7.66 – 7.51 (m, 5H), 7.51 – 7.28 (m, 10H). The 1H NMR data show a high degree of correspondence and reasonableness with the basic characteristics of the M11 structure.

[0190] Example 8:

[0191] This embodiment provides a nitrogen-containing heterocyclic compound M25, with the following specific chemical formula:

[0192]

[0193] M25

[0194] The synthesis steps of compound M25 are similar to those of compound M1 in Example 1. The main difference lies in the differences between intermediates M25-2 and M25-3. The synthetic route of intermediate M25-3 is as follows:

[0195]

[0196] The specific steps for synthesizing intermediate M25-3 are as follows: Under nitrogen protection, in a 2L four-necked flask, compound M25-2 (130mmol), starting material M25-c (160mmol), Pd132 (4mmol), X-Phos (7mmol), and sodium tert-butoxide (260mmol) were dissolved in 400mL of toluene at room temperature. The reaction was quenched after reflux and stirring at 120℃ for 5 hours. After extraction with dichloromethane, compound M25-3 was obtained by column chromatography (yield 62%).

[0197] Other preparation steps remained unchanged, and compound M25 was obtained. The structure of compound M25 was characterized, and the NMR data are as follows: 1 1H NMR (500 MHz, Chloroform-d) δ 8.32 – 8.25 (m, 2H), 8.22 – 8.15 (m, 3H), 7.74 – 7.66 (m, 3H), 7.66 – 7.60 (m, 4H), 7.58 – 7.28 (m, 14H). The NMR data show that this 1H NMR spectrum is highly consistent with and reasonable for the basic characteristics of the M25 structure.

[0198] Example 9:

[0199] This embodiment provides a nitrogen-containing heterocyclic compound M32, with the following specific chemical formula:

[0200]

[0201] M32

[0202] The synthesis steps of compound M32 are similar to those of compound M1 in Example 1. The main difference lies in the differences between intermediates M32-2 and M32-3. The synthetic route of intermediate M32-3 is as follows:

[0203]

[0204] The specific steps for synthesizing intermediate M32-3 are as follows: Under nitrogen protection, in a 2L four-necked flask, compound M32-2 (120mmol), starting material M32-c (140mmol), Pd132 (3.6mmol), X-Phos (5mmol), and sodium tert-butoxide (240mmol) were dissolved in 350mL of toluene at room temperature. The reaction was quenched after reflux and stirring at 120℃ for 8 hours. After extraction with dichloromethane, compound M32-3 was obtained by column chromatography (yield 45%).

[0205] Other preparation steps remained unchanged, and compound M32 was obtained. The structure of compound M32 was characterized, and the NMR data are as follows: 1 1H NMR (500 MHz, Chloroform-d) δ 8.32 – 8.25 (m, 2H), 8.22 – 8.16 (m, 2H), 8.05 (dd, J = 8.2, 1.3 Hz, 1H), 7.88 (dd, J = 6.6, 1.3 Hz, 1H), 7.77 (dd, J = 6.4, 1.6 Hz, 1H), 7.74 – 7.51 (m, 11H), 7.51 – 7.27 (m, 12H). The 1H NMR data show a high degree of correspondence and reasonableness with the basic characteristics of the M32 structural formula.

[0206] Example 10:

[0207] This embodiment provides a nitrogen-containing heterocyclic compound M51, with the following specific chemical formula:

[0208]

[0209] M51

[0210] The synthesis steps of compound M51 are similar to those of compound M1 in Example 1. The main difference lies in the differences between intermediates M51-2 and M51-3. The synthetic route of intermediate M51-3 is as follows:

[0211]

[0212] The specific steps for synthesizing intermediate M51-3 are as follows: Under nitrogen protection, in a 2L four-necked flask, compound M51-2 (100mmol), starting material M51-c (120mmol), Pd132 (3mmol), X-Phos (5mmol), and sodium tert-butoxide (200mmol) were dissolved in 300mL of toluene at room temperature. The reaction was quenched after reflux and stirring at 120℃ for 5 hours. After extraction with dichloromethane, compound M51-3 was obtained by column chromatography (yield 56%).

[0213] Other preparation steps remained unchanged, and compound M51 was obtained. The structure of compound M51 was characterized, and the NMR data are as follows: 1 1H NMR (500 MHz, Chloroform-d) δ 8.32 – 8.25 (m, 2H), 8.22 – 8.16 (m, 2H), 8.02 (dt, J = 8.3, 1.8 Hz, 1H), 7.97 (dd, J = 7.6, 1.6 Hz, 2H), 7.86 (d, J = 8.6 Hz, 1H), 7.80 – 7.66 (m, 4H), 7.66 – 7.28 (m, 16H). The 1H NMR data show a high degree of correspondence and reasonableness with the basic characteristics of the M51 structure.

[0214] Example 11:

[0215] This embodiment provides a nitrogen-containing heterocyclic compound M56, with the following specific chemical formula:

[0216]

[0217] M56

[0218] The synthesis steps of compound M56 are similar to those of compound M1 in Example 1. The main difference lies in the differences between intermediates M56-2 and M56-3. The synthetic route of intermediate M56-3 is as follows:

[0219]

[0220] The specific steps for synthesizing intermediate M56-3 are as follows: Under nitrogen protection, in a 2L four-necked flask, compound M56-2 (120mmol), starting material M56-c (140mmol), palladium acetate (4mmol), Xant-Phos (6mmol), and sodium tert-butoxide (240mmol) were dissolved in 350mL of toluene at room temperature. The reaction was quenched after reflux and stirring at 120℃ for 6 hours. After extraction with dichloromethane, compound M56-3 was obtained by column chromatography (yield 40%).

[0221] Other preparation steps remained unchanged, and compound M56 was obtained. The structure of compound M56 was characterized, and the NMR data are as follows: 1 1H NMR (500 MHz, Chloroform-d) δ 8.67 (dd, J = 4.0, 1.6 Hz, 1H), 8.32– 8.25 (m, 3H), 8.25 – 8.20 (m, 1H), 8.20 – 8.16 (m, 2H), 8.12 (dd, J = 8.3, 1.5 Hz, 1H), 8.01 (d, J = 8.9 Hz, 1H), 7.95 (dd, J = 7.7, 1.3 Hz, 1H), 7.80 –7.66 (m, 4H), 7.66 – 7.25 (m, 13H). The 1H NMR data show a high degree of correspondence and reasonableness with the basic characteristics of the M56 structure.

[0222] Example 12:

[0223] This embodiment provides a nitrogen-containing heterocyclic compound M69, with the following specific chemical formula:

[0224]

[0225] M69

[0226] The synthesis steps of compound M69 are similar to those of compound M1 in Example 1. The main difference lies in the differences between intermediates M69-2 and M69-3. The synthetic route of intermediate M69-3 is as follows:

[0227]

[0228] The specific steps for synthesizing intermediate M69-3 are as follows: Under nitrogen protection, in a 2L four-necked flask, compound M69-2 (100mmol), starting material M69-c (120mmol), Pd132 (3mmol), X-Phos (5mmol), and sodium tert-butoxide (200mmol) were dissolved in 300mL of toluene at room temperature. The reaction was quenched after reflux and stirring at 120℃ for 4 hours. After extraction with dichloromethane, compound M69-3 was obtained by column chromatography (yield 43%).

[0229] Other preparation steps remained unchanged, and compound M69 was obtained. The structure of compound M69 was characterized, and the NMR data are as follows: 1 H NMR (500 MHz, Chloroform-d) δ 8.86 – 8.81 (m, 2H), 8.37 (dd, J =9.3, 2.2 Hz, 1H), 8.32 – 8.25 (m, 2H), 8.22 – 8.15 (m, 3H), 8.05 (dd, J =7.1, 2.4 Hz, 1H), 7.82 (d, J = 7.2 Hz, 1H), 7.77 (dd, J = 6.4, 1.6 Hz, 1H), 7.74 – 7.67 (m, 2H), 7.67 – 7.60 (m, 3H), 7.58 – 7.28 (m, 16H). The NMR data show that the hydrogen NMR spectrum data is highly consistent with and reasonable in relation to the basic characteristics of the M69 structure.

[0230] Example 13:

[0231] This embodiment provides a nitrogen-containing heterocyclic compound M72, with the following specific chemical formula:

[0232]

[0233] M72

[0234] The synthesis steps of compound M72 are similar to those of compound M1 in Example 1. The main difference lies in the differences between intermediates M72-2 and M72-3. The synthetic route of intermediate M72-3 is as follows:

[0235]

[0236] The specific steps for synthesizing intermediate M72-3 are as follows: Under nitrogen protection, in a 2L four-necked flask, compound M72-2 (110 mmol), starting material M72-c (130 mmol), palladium acetate (3.3 mmol), X-Phos (5.5 mmol), and sodium tert-butoxide (220 mmol) were dissolved in 350 mL of toluene at room temperature. The reaction was quenched after reflux and stirring at 120 °C for 6 hours. After extraction with dichloromethane, compound M72-3 was obtained by column chromatography (yield 48%).

[0237] Other preparation steps remained unchanged, and compound M72 was obtained. The structure of compound M72 was characterized, and the NMR data are as follows: 1 H NMR (500 MHz, Chloroform-d) δ 8.81 (dd, J = 5.1, 2.2 Hz, 1H), 8.47 (dd, J = 8.6, 2.2 Hz, 1H), 8.32 – 8.25 (m, 2H), 8.22 – 8.15 (m, 4H), 7.76(dd, J = 6.3, 1.6 Hz, 1H), 7.74 – 7.65 (m, 4H), 7.63 (ddd, J = 6.3, 3.5, 1.0Hz, 2H), 7.54 (t, J = 7.0 Hz, 1H), 7.51 (s, 1H), 7.45 (ddd, J = 7.4, 6.3, 1.2Hz, 1H), 7.42 – 7.28 (m, 10H). The NMR data show that this 1H NMR spectrum is highly consistent with and reasonable in relation to the basic characteristics of the M72 structural formula.

[0238] Example 14:

[0239] This embodiment provides a nitrogen-containing heterocyclic compound M84, with the following specific chemical formula:

[0240]

[0241] M84

[0242] The synthesis steps of compound M84 are similar to those of compound M1 in Example 1. The main difference lies in the differences between intermediates M84-2 and M84-3. The synthetic route of intermediate M84-3 is as follows:

[0243]

[0244] The specific steps for synthesizing intermediate M84-3 are as follows: Under nitrogen protection, in a 2L four-necked flask, compound M84-2 (100mmol), starting material M84-c (120mmol), Pd2(dba)3 (3mmol), S-Phos (5mmol), and sodium tert-butoxide (200mmol) were dissolved in 320mL of toluene at room temperature. The reaction was quenched after reflux and stirring at 120℃ for 5 hours. After extraction with dichloromethane, compound M84-3 was obtained by column chromatography (yield 65%).

[0245] Other preparation steps remained unchanged, and compound M84 was obtained. The structure of compound M84 was characterized, and the NMR data are as follows: 1 H NMR (500 MHz, Chloroform-d) δ 9.15 (d, J = 1.9 Hz, 1H), 8.87 (t, J= 2.1 Hz, 1H), 8.35 (dd, J = 9.9, 2.2 Hz, 1H), 8.30 (d, J = 8.2 Hz, 2H), 8.22– 8.16 (m, 3H), 8.10 – 8.02 (m, 3H), 8.02 – 7.97 (m, 2H), 7.93 – 7.86 (m,1H), 7.83 (td, J = 7.0, 1.3 Hz, 1H), 7.74 – 7.57 (m, 7H), 7.57 – 7.47 (m,3H), 7.45 (ddd, J = 7.4, 6.2, 1.2 Hz, 1H), 7.39 – 7.27 (m, 5H). The NMR data show that this 1H NMR spectrum is highly consistent with and reasonable in relation to the basic characteristics of the M84 structure.

[0246] Performance characterization:

[0247] The nitrogen-containing heterocyclic compounds prepared in Examples 1 to 14 were dissolved in toluene to prepare a solution with a concentration of 10. -5 10 -6 The UV-Vis and PL of the nitrogen-containing heterocyclic compound in toluene solution were measured using a UV-Vis spectrophotometer and a fluorescence spectrophotometer, respectively.

[0248] Figure 2 This is the UV absorption spectrum of compound M1 in toluene solution from Example 1. Figure 3 The image shows the fluorescence emission spectrum of compound M1 in Example 1 in toluene solution. Table 1 shows the wavelengths of the maximum absorption peak and the maximum emission peak of compounds M1 to M84 in Examples 1 to 14 in toluene solution.

[0249] Table 1. Wavelengths of maximum absorption and emission peaks for compounds M1–M84 in toluene solution.

[0250]

[0251] Depend on Figure 2 , Figure 3 As shown in Table 1, the nitrogen-containing heterocyclic compounds prepared in the embodiments of this invention exhibit distinct ultraviolet absorption and fluorescence emission characteristics in toluene solution. Specifically, the maximum absorption peak wavelengths of these compounds are distributed between 465 nm and 492 nm, and the maximum emission peak wavelengths are distributed between 532 nm and 566 nm. These photophysical properties clearly demonstrate that by introducing different substituent groups or altering the aromatic ring structure at specific sites on the nitrogen-containing heterocyclic core framework, the conjugated system of the molecule can be effectively controlled, thereby achieving fine adjustment of the absorption and emission wavelengths. This tunable spectral characteristic not only indicates that this series of compounds has good luminescence capabilities but also confirms that a more suitable energy level distribution can be achieved through structural design. When these nitrogen-containing heterocyclic compounds are used as materials such as organic electroluminescent layers, they can maintain a high degree of matching with adjacent energy levels, which is beneficial for controlling the exciton recombination energy level in the molecular aggregate state and effectively controlling the triplet energy level, resulting in a more balanced carrier mobility. This also lays a solid material foundation for the final organic electroluminescent devices to achieve low driving voltage, high luminous efficiency, and long luminescence lifetime.

[0252] Application example:

[0253] Based on the materials prepared in the above embodiments, OLED light-emitting devices were further prepared in Application Examples 1-8 and Comparative Application Examples, and their structural schematic diagrams are shown below. Figure 4 As shown, Figure 4 In the diagram, 1 is the substrate (glass substrate), 2 is the anode (indium tin oxide coating ITO), 3 is the hole injection layer (HIL), 4 is the hole transport layer (HTL), 5 is the light-emitting layer (EML), 6 is the electron transport layer (ETL), 7 is the electron injection layer (EIL), and 8 is the cathode.

[0254] The fabrication steps of the above-mentioned OLED light-emitting device are as follows:

[0255] (1) Substrate cleaning: The glass substrate coated with transparent ITO is ultrasonically treated in an aqueous cleaning agent (the composition and concentration of the aqueous cleaning agent are: ethylene glycol solvent ≤10wt%, triethanolamine ≤1wt%), rinsed in deionized water, ultrasonically degreased in a mixed solvent of acetone and ethanol (volume ratio 1:1), baked in a clean environment until all moisture is removed, and then cleaned with ultraviolet light and ozone.

[0256] (2) Evaporation of organic light-emitting functional layer: The pretreated ITO glass substrate is placed in a vacuum chamber and evacuated to 1×10⁻⁶. -6 Up to 2×10 -4 Pa, a hole injection layer is vacuum-deposited on the above-mentioned anode layer film, with a deposition thickness of 10 nm;

[0257] A hole transport layer is deposited on the hole injection layer, and the deposited film thickness is 80 nm.

[0258] The light-emitting layer is deposited on the hole transport layer by vacuum evaporation. The specific preparation method is as follows: a mixture of the light-emitting host material and the dopant material is vacuum evaporated by co-evaporation. The host material is a PN bicomponent. The P component material is shown in Table 2, and the N component material is M1, M2, M25, M32, M51, M69, M72, M84 prepared in Examples 1 to 14. The total film thickness is 35 nm.

[0259] An electron transport layer is deposited on the light-emitting layer. The specific preparation method is as follows: the corresponding material is vacuum-deposited by co-evaporation, and the total film thickness is 30nm.

[0260] An electron injection layer is vacuum-deposited on the electron transport layer, with a total film thickness of 1 nm.

[0261] Al is deposited on the electron injection layer as a cathode, with a total film thickness of 90 nm, thus obtaining a complete OLED device.

[0262] The materials of each layer in Application Examples 1-8 and Comparative Application Examples are shown in Table 2.

[0263] Table 2. Materials of each layer in application examples 1-8 and comparative application examples.

[0264]

[0265] In Table 2, the specific materials are as follows:

[0266]

[0267] The OLED devices prepared according to cases 1-8 and comparative application examples were subjected to performance testing. The specific testing steps are as follows:

[0268] Instrumentation: The current, voltage, brightness, and emission spectrum characteristics of the device were simultaneously tested using a PR 650 spectral scanning luminance meter and a Keithley K 2400 digital source meter system; photoelectric characteristic test conditions: current density of 10 mA / cm². 2 .

[0269] Lifetime test: current density 30mA / cm 2The time (in hours) when the device brightness drops to 95% of its original brightness is recorded. Table 3 shows the test results of the OLED devices prepared in Application Examples 1-8 and Comparative Application Examples.

[0270] Table 3 Test results of OLED devices prepared in Application Examples 1-8 and Comparative Application Examples

[0271]

[0272] As shown in Table 3, the lowest driving voltage in Application Examples 1-8 is as low as 3.32V. Compared to the comparative application examples, this means less power is consumed during use, effectively reducing energy consumption and saving costs. It also reduces heat generation and other issues, contributing to long-term stable operation of the device. The highest current efficiency reaches 77.81Cd / A, with many application examples exceeding 75Cd / A. This indicates that under the same current input, the device emits brighter light with higher luminous efficiency, achieving better luminous effect with less power and improving energy utilization efficiency. The longest lifespan reaches 261 hours, with most application examples exceeding 200 hours, a significant improvement compared to the comparative examples. This demonstrates the device's durability, reducing the need for frequent replacements, lowering maintenance costs, and improving ease of use and stability, resulting in high reliability in practical applications.

[0273] This invention provides a nitrogen-containing heterocyclic compound, its preparation method, and its application. Many methods and approaches exist for implementing this technical solution; the above description is merely a preferred embodiment. It should be noted that those skilled in the art can make various improvements and modifications without departing from the principles of this invention, and these improvements and modifications should also be considered within the scope of protection of this invention. All components not explicitly stated in this embodiment can be implemented using existing technologies.

Claims

1. A nitrogen-containing heterocyclic compound, characterized in that, The nitrogen-containing heterocyclic compound has the structure shown in Formula 1: ； Formula 1 In Formula 1, L is selected from single bond, substituted or unsubstituted C6-C60 arylene, substituted or unsubstituted C3-C60 heteroarylene; Ar is selected from substituted or unsubstituted C3-C60 heteroarylene containing N atom. In the substituted C6-C60 arylene, substituted C3-C60 heteroarylene, and substituted C3-C60 heteroarylene containing an N atom, the substituents are selected from one or a combination of at least two of deuterium, halogen, cyano, hydroxyl, carbonyl, nitro, C1-C15 alkyl, C6-C60 aryl, and C3-C60 heteroarylene.

2. The nitrogen-containing heterocyclic compound according to claim 1, characterized in that, L is selected from a single bond, a substituted or unsubstituted A group; wherein the A group is selected from any one of phenylene, naphthylene, pyridylene, pyrimidinylene, quinolinylene, isoquinolinylene, quinazolinylene, quinoxalinylene, naphthylene, pyridopyrimidinylene, and pyrimidopyrimidinylene; Wherein, the substituents in the substituted A group are selected from one or a combination of at least two of the following: deuterium, halogen, cyano, hydroxyl, carbonyl, nitro, methyl, ethyl, n-propyl, isopropyl, tert-butyl, sec-butyl, tert-butyl, phenyl, naphthyl, phenanthryl, biphenyl, binatyl, phenylnaphthyl, naphthylphenyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl, naphthidyl, pyridopyrimidinyl, pyrimidopyrimidinyl, dibenzofuranyl, and dibenzothiopheneyl.

3. The nitrogen-containing heterocyclic compound according to claim 1, characterized in that, Ar is selected from the structure shown in Equation 2 below: ； Formula 2 In Equation 2, " " indicates a link key with L; X1 represents N or CR1, X2 represents N or CR2, X3 represents N or CR3, X4 represents N or CR4, X5 represents N or CR5, and at least one of X1-X5 is selected from N; R1-R5 are each independently selected from substituted or unsubstituted C6-C60 aryl groups, substituted or unsubstituted C3-C60 heteroaryl groups, or adjacent R1-R5 groups are bonded together to form substituted or unsubstituted C6-C60 aromatic rings or substituted or unsubstituted C3-C60 heteroaryl rings. The substituents in the substituted C6-C60 aryl, substituted C3-C60 heteroaryl, substituted C6-C60 aromatic ring, and substituted C3-C60 heteroaryl ring are selected from one or a combination of at least two of deuterium, halogen, cyano, hydroxyl, carbonyl, nitro, C1-C15 alkyl, C6-C60 aryl, and C3-C60 heteroaryl.

4. The nitrogen-containing heterocyclic compound according to claim 3, characterized in that, Ar is selected from any one of the structures shown in equations 2-1 to 2-12 below: ； In equations 2-1 to 2-12, " " indicates a linking bond with L; R' indicates a hydrogen, deuterium, substituted or unsubstituted B group; Wherein, group B is selected from phenyl, naphthyl, phenanthryl, biphenyl, binatyl, phenylnaphthyl, naphthylphenyl, triphenylene, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, pyridopyrimidinyl, pyrimidopyrimidinyl, dibenzofuranyl, dibenzothiopheneyl, N-phenylcarbazoyl, carbazoyl, phenylpyrimidinyl, phenylpyridinyl, pyrimidinylphenyl, pyridinylphenyl; the substituents in the substituted group B are selected from one or a combination of at least two of deuterium, halogen, cyano, hydroxyl, carbonyl, nitro, C1-C15 alkyl, C6-C60 aryl, and C3-C60 heteroaryl.

5. The nitrogen-containing heterocyclic compound according to claim 4, characterized in that, Ar is selected from any one of the structures shown in equations 3-1 to 3-20 below: ； In equations 3-1 to 3-20, " " indicates a linking bond with L; R' indicates a hydrogen, deuterium, substituted or unsubstituted B group; Wherein, group B is selected from phenyl, naphthyl, phenanthryl, biphenyl, binatyl, phenylnaphthyl, naphthylphenyl, triphenylene, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, pyridopyrimidinyl, pyrimidopyrimidinyl, dibenzofuranyl, dibenzothiopheneyl, N-phenylcarbazoyl, carbazoyl, phenylpyrimidinyl, phenylpyridinyl, pyrimidinylphenyl, pyridinylphenyl; the substituents in the substituted group B are selected from one or a combination of at least two of deuterium, halogen, cyano, hydroxyl, carbonyl, nitro, C1-C15 alkyl, C6-C60 aryl, and C3-C60 heteroaryl.

6. The nitrogen-containing heterocyclic compound according to any one of claims 1 to 5, characterized in that, The nitrogen-containing heterocyclic compound is selected from any one of the structures M1 to M84: ； ； ； ； ； ； ； ； ； ； ； ； ； ； ； ； ； ； ； ； 。 7. The method for preparing the nitrogen-containing heterocyclic compound according to any one of claims 1 to 6, characterized in that, The synthetic route of the preparation method is shown below: Where X is Cl-L-Ar.

8. An organic electroluminescent material, characterized in that, The organic electroluminescent material includes nitrogen-containing heterocyclic compounds as described in any one of claims 1 to 6.

9. An organic electroluminescent device, characterized in that, The organic electroluminescent device includes an anode, a cathode, and an organic layer located between the anode and the cathode, wherein the organic layer contains a nitrogen-containing heterocyclic compound as described in any one of claims 1 to 6 and / or an organic electroluminescent material as described in claim 8.

10. An electronic device, characterized in that, The electronic device includes any one or a combination of at least two of the nitrogen-containing heterocyclic compound as described in any one of claims 1 to 6, the organic electroluminescent material as described in claim 8, and the organic electroluminescent device as described in claim 9.

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