An organic electroluminescence element

Abstract

The present application provides a kind of organic electroluminescent element, including substrate, anode, organic layer, cathode, the organic material of triarylamine derivative represented by formula (I) used in the organic layer of the element, can effectively increase the combination probability of hole and electron, and the generated exciton is limited in the light-emitting layer, so as to improve the luminous efficiency and service life of organic electroluminescent element, and the combination of the triarylamine derivative represented by formula (I) and the fluorene-containing triarylamine compound represented by formula (II) can effectively improve the exciton utilization when used in organic light-emitting element, greatly improve the luminous efficiency and service life of element, with good application effect and industrialization prospect, can be widely used in panel display, lighting source, flexible OLED, electronic paper, organic solar cell, organic photoreceptor, sign, signal lamp and other fields.

Description

Technical Field

[0001] This invention relates to the field of organic electroluminescence technology, and more particularly to an organic electroluminescent element. Background Technology

[0002] Organic light-emitting diodes (OLEDs), as a novel display technology, possess unique advantages such as self-illumination, wide viewing angle, low energy consumption, high efficiency, thinness, rich colors, fast response speed, wide operating temperature range, low driving voltage, the ability to fabricate flexible, bendable, and transparent display panels, and environmental friendliness. OLED technology can be used to manufacture new display products as well as new lighting products, and is expected to replace existing liquid crystal displays and fluorescent lighting, with a very broad application prospect.

[0003] OLED optoelectronic functional materials used in OLED components can be broadly classified into three categories based on their applications: charge injection and transport materials, luminescent materials, and capping materials used to improve light extraction efficiency. Furthermore, charge injection and transport materials are further divided into electron injection materials, electron transport materials, hole injection materials, and hole transport materials. Luminescent materials can also be classified into host luminescent materials and doped materials.

[0004] The optoelectronic functional materials that make up OLED devices consist of at least two layers. Industrially applied OLED device structures include multiple layers such as hole injection layers, hole transport layers, light-emitting layers, and electron injection layers. In other words, the optoelectronic functional materials used in OLED devices include at least hole injection materials, hole transport materials, light-emitting materials, and electron injection materials, exhibiting richness and diversity in material types and combinations. Furthermore, the optoelectronic functional materials used are highly selective for different OLED device structures; the same material may exhibit completely different performance characteristics in different structural devices.

[0005] Research on improving the performance of OLED light-emitting elements includes reducing the driving voltage, increasing luminous efficiency, and extending lifespan. To continuously improve OLED performance, innovation in OLED element structure and manufacturing processes is needed, along with ongoing research and innovation in OLED optoelectronic functional materials to create higher-performance OLED functional materials.

[0006] To fabricate high-performance OLED light-emitting elements, various organic functional materials are required to have good photoelectric properties. For example, as charge transport materials, they are required to have good carrier mobility and high glass transition temperature. As light-emitting layer materials, they are required to have good fluorescence quantum efficiency, material evaporation stability, and appropriate HOMO / LUMO energy levels.

[0007] However, current OLED devices are limited in application due to low efficiency and short lifespan, so it is necessary to improve these limitations. Among these measures, reducing the energy barrier between the hole injection / transport material and the light-emitting material and improving the thermal stability of the hole transport material can help improve the efficiency and lifespan of OLED devices.

[0008] Overall, the future direction of OLED is to develop high-efficiency, long-life, and low-cost white light elements and full-color display elements. However, the industrialization process of this technology still faces many key issues. How to design better-performing organic electroluminescent elements for regulation has always been a problem that needs to be solved by those in the field. Summary of the Invention

[0009] The purpose of this invention is to provide an organic electroluminescent element, which aims to improve the element characteristics of the organic electroluminescent element, especially to significantly improve the luminous efficiency and lifespan of the element.

[0010] To achieve the above objectives, this invention provides an organic electroluminescent element and provides an in-depth evaluation of its characteristics, thus solving the aforementioned problems. The organic electroluminescent element provided by this invention includes a substrate, an anode, an organic layer, and a cathode. The organic layer includes a hole transport layer, and the hole transport layer contains a triarylamine derivative represented by formula (I).

[0011]

[0012] The r is selected from 1 or 2;

[0013] When r equals 1, R is selected from substituted or unsubstituted C7-C12 cycloalkyl groups;

[0014] When r equals 2, the two Rs are the same or different from each other and are selected from substituted or unsubstituted C7 to C12 cycloalkyl groups, or two adjacent Rs are connected to form a C3 to C12 aliphatic ring;

[0015] The Ar0 is selected from any one of deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl.

[0016] The R0 and R1 are independently selected from any one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C3-C30 cycloalkenyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl, or adjacent R0 can be bonded together to form a benzene ring or a naphthalene ring, and adjacent R1 can be bonded together to form a benzene ring or a naphthalene ring;

[0017] The m is selected from 0, 1, 2, 3 or 4; when m is greater than 1, two or more R0s are the same or different from each other, or two adjacent R0s are connected to form a benzene ring or a naphthalene ring;

[0018] The n is selected from 0, 1, 2 or 3; when n is greater than 1, two or more R1s are the same or different from each other, or two adjacent R1s are connected to form a benzene ring or a naphthalene ring;

[0019] The Ar1 and Ar2 may be the same as or different from each other, and are independently selected from one of the following substituents:

[0020]

[0021]

[0022] The R b It is selected from one of the following: substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C6-C25 aryl, and substituted or unsubstituted C2-C20 heteroaryl.

[0023] The R a Selected from one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C20 heteroaryl, or adjacent R a They can be linked together to form benzene rings or naphthalene rings;

[0024] Wherein R a It can also be R aa Replaced by, R aaIt is selected from one or more of hydrogen, deuterium, methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, adamantyl, norbornel, phenyl, pentadeuterated phenyl, deuterated naphthyl, tolyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, stilbenzyl, spirofluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-phenylcarbazolyl, dibenzothiophene, and dibenzofuranyl, wherein when substituted with multiple substituents, the multiple substituents are the same as or different from each other;

[0025] The at least one X is selected from N, and the remaining X are selected from CR. a ;

[0026] a' is 0, 1, or 2; a0 is 0, 1, 2, or 3; a1 is 0, 1, 2, 3, or 4; a2 is 0, 1, 2, 3, 4, or 5; a3 is 0, 1, 2, 3, 4, 5, 6, or 7; a4 is 0, 1, 2, 3, 4, 5, 6, 7, or 8; a5 is 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9.

[0027] The L0 to L3 are independently selected from any one of single-bonded, substituted or unsubstituted C6 to C30 aryl groups, and substituted or unsubstituted C2 to C30 heteroaryl groups, wherein the substituent is selected from one or more of deuterium, methyl, ethyl, isopropyl, tert-butyl, cyclobutyl, cyclopentyl, cyclohexyl, canyl, norbornel, adamantyl, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, naphthyl, deuterated naphthyl, anthracene, phenanthrene, benzo[a]phenanthrene, tolyl, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, carbazolyl, 9-phenylcarbazolyl, furanyl, thiophene, benzo[a]furanyl, benzo[a]thiophene, dibenzo[a]furanyl, and dibenzo[a]thiophene.

[0028] The beneficial effects of this invention are:

[0029] This invention provides an organic electroluminescent element. The organic material of the triarylamine derivative represented by formula (I) used in the hole transport layer of this element can effectively increase the probability of hole and electron binding and confine the generated excitons within the light-emitting layer, thereby improving the luminous efficiency and lifespan of the organic electroluminescent element. The combination of the triarylamine derivative represented by formula (I) and the fluorene-containing triarylamine compound represented by formula (II) makes the distribution of electrons and holes in the light-emitting layer more balanced. At the appropriate HOMO energy level, it improves the hole injection / transport performance; at the appropriate LUMO energy level, it improves the exciton recombination efficiency in the light-emitting layer. When used in organic light-emitting elements, it can effectively improve the exciton utilization rate, greatly improve the luminous efficiency and lifespan of the element, and has good application effects and industrialization prospects. Detailed Implementation

[0030] The technical solutions of the embodiments of the present invention will be clearly and completely described below. Obviously, the described embodiments are only some embodiments of the present invention, and not all embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without creative effort are within the protection scope of the present invention.

[0031] The alkyl group described in this invention refers to a hydrocarbon group formed by removing one hydrogen atom from an alkane molecule. It can be a straight-chain alkyl group or a branched-chain alkyl group, preferably having 1 to 15 carbon atoms, more preferably 1 to 12 carbon atoms, and particularly preferably 1 to 6 carbon atoms. The straight-chain alkyl group includes methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl, etc., but is not limited thereto. The branched-chain alkyl group includes isopropyl, isobutyl, sec-butyl, tert-butyl, isomeric groups of n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, etc., but is not limited thereto. The alkyl group is preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl.

[0032] The cycloalkyl group described in this invention refers to a hydrocarbon group formed by removing one hydrogen atom from a cycloalkane molecule, preferably having 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, and particularly preferably 3 to 6 carbon atoms. Examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, camphenyl, norbornyl, etc., but are not limited thereto. The alkyl group is preferably cyclopentyl, cyclohexyl, 1-adamantyl, 2-adamantyl, or norbornyl.

[0033] The aryl group described in this invention refers to the general term for a monovalent group remaining after removing a hydrogen atom from the aromatic carbon atom of an aromatic compound molecule. It can be a monocyclic aryl, polycyclic aryl, or fused-ring aryl, preferably having 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 14 carbon atoms. The monocyclic aryl refers to an aryl group with only one aromatic ring in the molecule, such as phenyl, but not limited thereto; the polycyclic aryl refers to an aryl group containing two or more independent aromatic rings in the molecule, such as biphenyl, terphenyl, etc., but not limited thereto; the fused-ring aryl refers to an aryl group containing two or more aromatic rings fused together by sharing two adjacent carbon atoms, such as naphthyl, anthracene, phenanthryl, pyrene, peryl, fluorenyl, benzo[a]fluorenyl, triphenylene, fluoranyl, spirodifluorenyl, etc., but not limited thereto. The aryl group is preferably phenyl, biphenyl, terphenyl, naphthyl (preferably 2-naphthyl), anthracene (preferably 2-anthrayl), phenanthryl, pyrene, peryl, fluorene, benzo[a]fluorene, triphenylene, or spirodifluorene.

[0034] The heteroaryl group described in this invention refers to the general term for groups obtained by replacing one or more aromatic carbon atoms in an aryl group with heteroatoms. The heteroatoms include, but are not limited to, oxygen, sulfur, nitrogen, or phosphorus atoms, preferably having 1 to 25 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 3 to 15 carbon atoms. The linking site of the heteroaryl group can be located on a cyclic carbon atom or on a cyclic nitrogen atom. The heteroaryl group can be a monocyclic heteroaryl, a polycyclic heteroaryl, or a fused-ring heteroaryl. The monocyclic heteroaryl groups include, but are not limited to, pyridinyl, pyrimidinyl, triazinyl, furanyl, thiopheneyl, pyrroleyl, imidazolyl, etc.; the polycyclic heteroaryl groups include, but are not limited to, bipyridinyl, bipyrimidinyl, phenylpyridinyl, etc.; the fused-ring heteroaryl groups include, but are not limited to, quinolinyl, isoquinolinyl, indolyl, benzothiopheneyl, benzofuranyl, benzoxazolyl, benzoimidazolyl, benzothiazolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothiopheneyl, benzodibenzothiapheneyl, carbazolyl, benzocarbazolyl, acridinel, 9,10-dihydroacridinyl, phenoxazinyl, phenthiazinyl, phenoxthiazyl, etc., but are not limited to. The aforementioned heteroaryl groups are preferably pyridyl, pyrimidinyl, thiophene, furanyl, benzothiophene, benzofuranyl, benzooxazolyl, benzoimidazolyl, benzothiazolyl, dibenzofuranyl, dibenzothiophene, benzodibenzothiophene, benzodibenzofuranyl, carbazolyl, acridinel, phenoxazinyl, phenthiazinyl, and phenoxthialyl.

[0035] The alkenyl group described in this invention refers to a monovalent group obtained by removing one hydrogen atom from an olefin molecule. The alkenyl group includes monoalkenyl, dienyl, polyalkenyl, etc. Preferably, it has 2 to 60 carbon atoms, more preferably 2 to 30 carbon atoms, particularly preferably 2 to 15 carbon atoms, and most preferably 2 to 6 carbon atoms. Examples of the alkenyl group include vinyl, butadieneyl, etc., but are not limited thereto. The aforementioned alkenyl group is preferably vinyl.

[0036] The cycloalkenyl group described in this invention refers to a monovalent group obtained by removing one hydrogen atom from a cycloalkene molecule. The cycloalkenyl group is a cyclic hydrocarbon group with an intracyclic carbon-carbon double bond, and includes cyclic monoalkenes, cyclic polyalkenes, etc. Preferably, it has 3 to 60 carbon atoms, more preferably 3 to 30 carbon atoms, particularly preferably 3 to 15 carbon atoms, and most preferably 3 to 6 carbon atoms. Examples of the alkenyl group include cyclopropene, cyclobutene, cyclopentene, cyclohexene, cyclobutadiene, cyclopentadiene, etc., but are not limited thereto.

[0037] The arylene group referred to in this invention refers to the general term for the divalent group remaining after removing two hydrogen atoms from the aromatic carbon atom of an aromatic compound molecule. It can be a monocyclic arylene, a polycyclic arylene, or a fused-ring arylene, preferably having 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 14 carbon atoms. The monocyclic arylene includes, but is not limited to, phenylene; the polycyclic arylene includes, but is not limited to, biphenylene, terphenylene; the fused-ring arylene includes, but is not limited to, naphthylene, anthracene, phenanthrene, fluorene, pyrene, trimethyleneene, fluorene, phenylfluorene, etc., but is not limited to. The aforementioned arylene groups are preferably phenylene, biphenylene, terphenylene, naphthyl, fluorene, or phenylfluorene.

[0038] The heteroaryl group described in this invention refers to the general term for groups obtained by replacing one or more aromatic carbon atoms in an aryl group with heteroatoms. These heteroatoms include, but are not limited to, oxygen, sulfur, nitrogen, or phosphorus atoms. Preferably, it has 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 15 carbon atoms. The linking site of the heteroaryl group can be located on a cyclic carbon atom or a cyclic nitrogen atom. The heteroaryl group can be a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a fused-ring heteroaryl group. The monocyclic heteroaryl group includes, but is not limited to, pyridinyl, pyrimidinyl, triazinyl, furanyl, and thiopheneyl; the polycyclic heteroaryl group includes, but is not limited to, bipyridinyl, bipyrimidinyl, and phenylpyridinyl; the fused-ring heteroaryl group includes, but is not limited to, quinolineyl, isoquinolineyl, indolyl, benzothiophene, benzofuranyl, benzoxazolyl, benzoimidazolyl, benzothiazolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothiaphene, benzodibenzothiaphene, carbazolyl, benzocarbazolyl, acridineyl, 9,10-dihydroacridinyl, phenoxazinyl, phenthiazinyl, and phenoxthiazolyl, but is not limited to. The aforementioned heteroaryl groups are preferably pyridinyl, pyrimidinyl, thiopheneyl, furanyl, benzothiopheneyl, benzofuranyl, benzoxazolyl, benzoimidazolyl, benzothiazolyl, dibenzofuranyl, dibenzothiopheneyl, benzodibenzothiopheneyl, benzodibenzofuranyl, carbazolyl, acridineyl, phenoxazinyl, phenoxazinyl, and phenoxthiazolyl.

[0039] The term "substituted..." as used in this invention refers to monosubstituted or polysubstituted groups, such as substituted alkyl, substituted cycloalkyl, substituted alkenyl, substituted cycloalkenyl, substituted aryl, substituted heteroaryl, substituted arylene, substituted heteroaryl, etc., independently selected from, but not limited to, deuteryl, halogen, cyano, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C3-C30 cycloalkenyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, substituted or unsubstituted amino, etc., preferably selected from, but not limited to, groups that are monosubstituted or polysubstituted. The following groups are monosubstituted or polysubstituted: deuteryl, methyl, ethyl, isopropyl, tert-butyl, cyclobutyl, cyclopentyl, cyclohexyl, canyl, norbornelyl, adamantyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, benzo[a]phenanthrene, perylene, pyrene, benzyl, tolyl, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, diphenylamino, dimethylamino, carbazolyl, 9-phenylcarbazolyl, acridineyl, furanyl, thiophene, benzofuranyl, benzothiophene, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, dibenzothiophene, phenothiazinyl, phenothiazinyl, and indole. In addition, the above-mentioned substituents may be replaced by one or more substituents selected from deuteryl, halogen atom, cyano, alkyl, cycloalkyl, and aryl.

[0040] The aliphatic hydrocarbons described in this invention refer to aliphatic hydrocarbons having 1 to 60 carbon atoms, which may be completely unsaturated or partially unsaturated. Preferably, the aliphatic hydrocarbons have 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, even more preferably 1 to 10 carbon atoms, and most preferably 1 to 6 carbon atoms.

[0041] The aliphatic rings described in this invention refer to cyclic hydrocarbons with aliphatic properties, containing closed carbon rings in the molecule. These rings can be monocyclic or polycyclic hydrocarbons formed by 3-18, preferably 3-12, and more preferably 3-7 carbon atoms. They can be completely unsaturated or partially unsaturated, such as cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, cycloheptene, etc., but are not limited thereto. Multiple monocyclic hydrocarbons can also be linked in various ways: two rings in the molecule can share a carbon atom to form a spirocyclic ring; two carbon atoms on a ring can be connected by a carbon bridge to form a bridged ring; several rings can also be interconnected to form a cage-like structure.

[0042] The cyclic structure formed by bonding as described in this invention refers to two groups being linked together by chemical bonds and optionally aromatized. Examples are shown below:

[0043]

[0044] In this invention, the ring formed by the connection can be a five-membered ring, a six-membered ring, or a fused ring, such as phenyl, naphthyl, cyclopentenyl, cyclopentyl, cyclohexanephenyl, quinolinyl, isoquinolinyl, dibenzothiophene, phenanthrene, or pyrene, but is not limited thereto.

[0045] This invention provides an organic electroluminescent element, comprising a substrate, an anode, an organic layer, and a cathode. The organic layer of this organic electroluminescent element can be formed as a single layer or as a multilayer structure with multiple organic layers stacked together. The organic layer may include one or more of the following: a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a capping layer. Some organic layers may be added or omitted. The organic layers contain one or more combinations of triarylamine derivatives represented by formula (I). Furthermore, each organic layer may contain one or more layers; for example, the electron transport layer may include a first electron transport layer and a second electron transport layer. Corresponding functional layers can be added or removed as needed.

[0046] The organic electroluminescent element of the present invention preferably has the following structure:

[0047] (1) Anode / hole injection layer / hole transport layer / light emission layer / electron transport layer / cathode; (2) Anode / hole injection layer / hole transport layer / light emission layer / hole blocking layer / electron transport layer / cathode; (3) Anode / hole injection layer / hole transport layer / electron blocking layer / light emission layer / hole blocking layer / electron transport layer / cathode; (4) Anode / hole injection layer / hole transport layer / light emission layer / electron transport layer / cathode / capping layer; (5) Anode / hole injection layer / hole transport layer / light emission layer / cathode; (6) Anode / hole injection layer / hole transport layer / light emission layer / electron transport layer / electron injection layer / cathode; (7) Anode / hole injection layer / hole transport layer / light emission layer / electron transport layer / cathode; (8) Anode / hole injection layer / hole transport layer / electron transport layer / electron injection layer / cathode / capping layer; (9) Anode / hole injection layer / first hole transport layer / second hole transport layer / light-emitting layer / electron transport layer / cathode; (10) Anode / hole injection layer / first hole transport layer / second hole transport layer / light-emitting layer / electron transport layer / cathode; (11) Anode / hole injection layer / first hole transport layer / second hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode; (12) Anode / hole injection layer / first hole transport layer / second hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode; Hole transport layer / second hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode / capping layer; (13) anode / hole injection layer / first hole transport layer / second hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / cathode / capping layer; (14) anode / hole injection layer / first hole transport layer / second hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / cathode; (15) anode / hole injection layer / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / cathode / capping layer; (16) anode / hole injection layer / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / electron injection layer / (17) Anode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / hole blocking layer / electron transport layer / cathode / capping layer; (18) Anode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode / capping layer; (19) Anode / hole injection layer / first hole transport layer / second hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode; (20) Anode / hole injection layer / first hole transport layer / second hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode / capping layer.

[0048] However, the structure of organic electroluminescent elements is not limited to this. The organic electroluminescent elements described in this invention can be selected and combined according to the element parameter requirements and material properties, and some organic layers can be added or omitted. For example, a hole buffer layer can be added between the hole transport layer and the hole injection layer, and an electron buffer layer can be added between the electron transport layer and the electron injection layer. Furthermore, organic layers with the same function can be fabricated into a stacked structure of two or more layers.

[0049] The organic electroluminescent element of the present invention is typically formed on a substrate. The substrate need not change during the formation of electrodes and organic layers; for example, substrates made of glass, plastic, polymer films, silicon, etc. When the substrate is opaque, the electrodes opposite it are preferably transparent or translucent.

[0050] In the organic electroluminescent element of this invention, the anode material can be selected from metals, such as copper, gold, silver, iron, chromium, nickel, manganese, palladium, platinum, and their alloys; metal oxides, such as indium oxide, zinc oxide, indium tin oxide (ITO), indium zinc oxide (IZO), and zinc aluminum oxide; and conductive polymers, such as polyaniline, polypyrrole, and poly(3-methylthiophene). Besides the above materials and combinations thereof, the anode material may also include other known materials suitable for use as anodes. Examples of manufacturing methods include vacuum evaporation, sputtering, ion plating, and deposition. Furthermore, organic transparent conductive films such as polyaniline or its derivatives, and polythiophene or its derivatives can be used as the anode.

[0051] In the organic electroluminescent element of the present invention, the hole injection material can be a metal oxide such as molybdenum oxide, silver oxide, vanadium oxide, tungsten oxide, ruthenium oxide, nickel oxide, copper oxide, titanium oxide, etc., or a low-molecular-weight organic compound such as phthalocyanine compounds or conjugated organic materials containing polycyano groups, but is not limited thereto.

[0052] In the organic electroluminescent element of the present invention, the hole transport layer may be selected from small molecule materials such as aromatic amine derivatives, carbazole derivatives, stilbene derivatives, triphenyldiamine derivatives, styrene compounds, and butadiene compounds, as well as polymer materials such as poly(p-phenylene) derivatives, polyaniline and its derivatives, polythiophene and its derivatives, polyvinylcarbazole and its derivatives, and polysilane and its derivatives, but is not limited thereto. The hole transport layer of the present invention may be formed by stacking single, double, or multiple organic layers. Preferably, the hole transport layer of the present invention contains one or more combinations of triaromatic amine derivatives represented by formula (Ⅰ).

[0053]

[0054] The r is selected from 1 or 2;

[0055] When r equals 1, R is selected from substituted or unsubstituted C7-C12 cycloalkyl groups;

[0056] When r equals 2, the two Rs are the same or different from each other and are selected from substituted or unsubstituted C7 to C12 cycloalkyl groups, or two adjacent Rs are connected to form a C3 to C12 aliphatic ring;

[0057] The Ar0 is selected from any one of deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl.

[0058] The R0 and R1 are independently selected from any one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C3-C30 cycloalkenyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl, or adjacent R0 can be bonded together to form a benzene ring or a naphthalene ring, and adjacent R1 can be bonded together to form a benzene ring or a naphthalene ring;

[0059] The m is selected from 0, 1, 2, 3 or 4; when m is greater than 1, two or more R0s are the same or different from each other, or two adjacent R0s are connected to form a benzene ring or a naphthalene ring;

[0060] The n is selected from 0, 1, 2 or 3; when n is greater than 1, two or more R1s are the same or different from each other, or two adjacent R1s are connected to form a benzene ring or a naphthalene ring;

[0061] The Ar1 and Ar2 may be the same as or different from each other, and are independently selected from one of the following substituents:

[0062]

[0063]

[0064] The R b It is selected from one of the following: substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C6-C25 aryl, and substituted or unsubstituted C2-C20 heteroaryl.

[0065] The R aSelected from one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C20 heteroaryl, or adjacent R a They can be linked together to form benzene rings or naphthalene rings;

[0066] Wherein R a It can also be R aa Replaced by, R aa It is selected from one or more of hydrogen, deuterium, methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, adamantyl, norbornel, phenyl, pentadeuterated phenyl, deuterated naphthyl, tolyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, stilbenzyl, spirofluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-phenylcarbazolyl, dibenzothiophene, and dibenzofuranyl, wherein when substituted with multiple substituents, the multiple substituents are the same as or different from each other;

[0067] The at least one X is selected from N, and the remaining X are selected from CR. a ;

[0068] a' is 0, 1, or 2; a0 is 0, 1, 2, or 3; a1 is 0, 1, 2, 3, or 4; a2 is 0, 1, 2, 3, 4, or 5; a3 is 0, 1, 2, 3, 4, 5, 6, or 7; a4 is 0, 1, 2, 3, 4, 5, 6, 7, or 8; a5 is 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9.

[0069] The L0 to L3 are independently selected from any one of single-bonded, substituted or unsubstituted C6 to C30 aryl groups, and substituted or unsubstituted C2 to C30 heteroaryl groups, wherein the substituent is selected from one or more of deuterium, methyl, ethyl, isopropyl, tert-butyl, cyclobutyl, cyclopentyl, cyclohexyl, canyl, norbornel, adamantyl, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, naphthyl, deuterated naphthyl, anthracene, phenanthrene, benzo[a]phenanthrene, tolyl, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, carbazolyl, 9-phenylcarbazolyl, furanyl, thiophene, benzo[a]furanyl, benzo[a]thiophene, dibenzo[a]furanyl, and dibenzo[a]thiophene.

[0070] Preferably, R is selected from one of the following cycloalkyl groups:

[0071]

[0072] The R pIt is selected from one of hydrogen, deuterium, halogen atom, cyano, C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C3-C30 cycloalkenyl, substituted or unsubstituted C6-C25 aryl, and substituted or unsubstituted C2-C25 heteroaryl.

[0073] p1 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; p2 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14 or 15.

[0074] Preferably, the R p It is selected from one of hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, canyl, phenyl, biphenyl, deuterated phenyl, deuterated naphthyl, deuterated biphenyl, and tolyl.

[0075] Preferably, the two adjacent Rs are connected to form a cycloalkyl group as shown below:

[0076]

[0077] The R q It is selected from one of hydrogen, deuterium, halogen atom, cyano, C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C3-C30 cycloalkenyl, substituted or unsubstituted C6-C25 aryl, and substituted or unsubstituted C2-C25 heteroaryl.

[0078] The q1 is selected from 0, 1, or 2; the q2 is selected from 0, 1, 2, 3, or 4; the q3 is selected from 0, 1, 2, 3, 4, 5, or 6; the q4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the q5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.

[0079] In this context, "*" represents a connection point.

[0080] Preferably, the R q It is selected from one of hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, canyl, phenyl, biphenyl, deuterated phenyl, deuterated naphthyl, deuterated biphenyl, and tolyl.

[0081] Preferably, the R bIt is selected from one of methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, canyl, phenyl, biphenyl, deuterated phenyl, deuterated naphthyl, deuterated biphenyl, tolyl, terphenyl, naphthyl, anthracene, phenanthrene, stilbene, spirofluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-phenylcarbazolyl, dibenzothiophene, and dibenzofuranyl.

[0082] Preferably, the R a Selected from one of hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, canyl, phenyl, naphthyl, biphenyl, deuterated phenyl, deuterated naphthyl, deuterated biphenyl, tolyl, anthracene, phenanthrene, and triphenylene, or adjacent R a They can be linked together to form benzene rings or naphthalene rings.

[0083] Preferably, R0 and R1 are independently selected from hydrogen, deuterium, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, canyl, or any one of the following groups:

[0084] The d' is 0, 1, or 2; the d0 is 0, 1, 2, or 3; the d1 is 0, 1, 2, 3, or 4; the d2 is 0, 1, 2, 3, 4, or 5; the d3 is 0, 1, 2, 3, 4, 5, 6, or 7; and the d5 is 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9.

[0085] More preferably, the R0s are selected from hydrogen, deuterium, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, canyl, or any of the following groups:

[0086]

[0087] More preferably, the R0s are selected from hydrogen, deuterium, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, canyl, or any of the following groups:

[0088]

[0089] More preferably, the R1s are selected from hydrogen, deuterium, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, canyl, or any of the following groups:

[0090]

[0091] Preferably, adjacent R0 and R1 can be bonded together to form a ring.

[0092] More preferably, adjacent R0s can be bonded together to form a benzene ring or a naphthalene ring, and adjacent R1s can be bonded together to form a benzene ring or a naphthalene ring.

[0093] Preferably, L0, L1, L2, and L3 are independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted 9,9-dimethylfluorene, substituted or unsubstituted 9,9-diphenylfluorene, substituted or unsubstituted spirofluorene, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthylene, substituted or unsubstituted trimethyleneene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted The 9-phenylcarbazolyl, substituted or unsubstituted benzoxadiazolyl, substituted or unsubstituted benzothiadiazolyl, substituted or unsubstituted phenyl-naphthylene, wherein the substituent is one or more of deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, canyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, tolyl, and biphenyl. When substituted by multiple substituents, the multiple substituents are the same or different from each other, or adjacent substituents can be linked to form a benzene ring or a naphthyl ring.

[0094] Preferably, L0, L1, L2, and L3 are independently selected from single bonds or any one of the following groups:

[0095]

[0096]

[0097] More preferably, L0 and L1 are independently selected from single bonds or one of the following groups:

[0098]

[0099] More preferably, L2 and L3 are independently selected from single bonds or one of the following groups:

[0100]

[0101] Most preferably, L0 and L1 are independently selected from single bonds or one of the following groups:

[0102]

[0103] Most preferably, L2 and L3 are independently selected from single bonds or one of the following groups:

[0104]

[0105]

[0106] Preferably, Ar0 is selected from deuterium, methyl, ethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, or any one of the following groups:

[0107]

[0108] More preferably, Ar0 is selected from deuterium, methyl, ethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, or any one of the following groups:

[0109]

[0110] Preferably, the triarylamine derivative is selected from any one of the following chemical structures:

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134] In the organic electroluminescent element of the present invention, the hole transport layer includes a first hole transport layer and a second hole transport layer. The first hole transport layer is located between the anode and the second hole transport layer, and the second hole transport layer is located between the first hole transport layer and the cathode. Preferably, the first hole transport layer of the present invention contains any one or a combination of at least two of the triarylamine derivatives represented by formula (I), and the second hole transport layer contains any one or a combination of at least two of the fluorene-containing triarylamine compounds represented by formula (II).

[0135]

[0136] The A is selected from one of formulas A-1, A-2, and A-3; wherein R... 11 R 12 Independently selected from any one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C3-C30 cycloalkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or adjacent R 11 They can bond together to form benzene rings or naphthalene rings, adjacent R 12 They can bond together to form benzene rings or naphthalene rings;

[0137] The value of 'a' is selected from 0, 1, 2, 3, or 4; the value of 'b' is selected from 0, 1, 2, or 3.

[0138] The R 22 Selected from any one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or R 22 With R 22 They connect to form fatty rings;

[0139] The Ar is selected from one of the following groups:

[0140]

[0141] Wherein, the R c It is selected from one of hydrogen, deuterium, halogen atom, cyano, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, and substituted or unsubstituted C2-C20 heteroaryl.

[0142] k is selected from 0, 1, or 2; i is selected from 0, 1, 2, or 3; j is selected from 0, 1, 2, 3, 4, 5, 6, or 7; d is selected from 0, 1, 2, 3, or 4; h is selected from 0, 1, 2, 3, 4, or 5; e is selected from 0, 1, 2, 3, 4, 5, or 6; f is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; g is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.

[0143] The Ar a It is selected from any one of deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl;

[0144] The L a ~L c It is independently selected from any one of the following: single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted C6-C30 arylene-substituted or unsubstituted C2-C30 heteroarylene, or adjacent substituents can be bonded together to form a cyclic structure.

[0145] Preferably, the R cIt is selected from one of the following: hydrogen, deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, canyl, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, naphthyl, deuterated naphthyl, anthracene, phenanthrene, triphenylene, perylene, pyrene, tolyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-phenylcarbazolyl, acridine, dibenzofuranyl, dibenzothiophene, deuterated 9,9-dimethylfluorenyl, deuterated 9,9-diphenylfluorenyl, deuterated 9-phenylcarbazolyl, deuterated dibenzofuranyl, deuterated dibenzothiophene, phenothiazinyl, phenotoxazinyl, and indole.

[0146] More preferably, the Ar is selected from one of the following groups:

[0147]

[0148] Preferably, the Ar a Selected from one of the following groups:

[0149]

[0150] The R t It is selected from one of the following: substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, and substituted or unsubstituted C2-C20 heteroaryl;

[0151] The R s Selected from one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C20 heteroaryl, or adjacent R s They can be connected to form a ring structure;

[0152] Wherein, the R s It can also be R ss Replaced by, R ss It is selected from one or more of hydrogen, deuterium, methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornel, canyl, phenyl, pentadeuterated phenyl, deuterated naphthyl, tolyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, stilbene, spirofluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-phenylcarbazolyl, dibenzothiophene, and dibenzofuranyl, wherein when substituted with multiple substituents, the multiple substituents are the same or different from each other;

[0153] The s' is 0, 1, or 2; the s0 is 0, 1, 2, or 3; the s1 is 0, 1, 2, 3, or 4; the s2 is 0, 1, 2, 3, 4, or 5; the s3 is 0, 1, 2, 3, 4, 5, 6, or 7; and the s4 is 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9.

[0154] More preferably, the R t It is selected from one of methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornel, canyl, phenyl, pentadeuterated phenyl, deuterated naphthyl, deuterated biphenyl, tolyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, spirofluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-phenylcarbazolyl, dibenzothiophene, dibenzofuranyl, deuterated anthracene, deuterated phenanthrene, deuterated triphenylene, deuterated spirofluorenyl, deuterated 9,9-dimethylfluorenyl, deuterated 9,9-diphenylfluorenyl, deuterated 9-phenylcarbazolyl, deuterated dibenzothiophene, and deuterated dibenzofuranyl.

[0155] More preferably, the R s Selected from hydrogen, deuterium, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornel, canyl, phenyl, pentadeuterated phenyl, deuterated naphthyl, deuterated biphenyl, tolyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, stilbene, spirofluorene, 9,9-dimethyl One of the following: fluorenyl, 9,9-diphenylfluorenyl, 9-phenylcarbazolyl, dibenzothiophene, dibenzofuranyl, deuterated anthracene, deuterated phenanthrene, deuterated triphenylene, deuterated spirofluorenyl, deuterated 9,9-dimethylfluorenyl, deuterated 9,9-diphenylfluorenyl, deuterated 9-phenylcarbazolyl, deuterated dibenzothiophene, deuterated dibenzofuranyl, or adjacent R s They can be connected to form a ring structure.

[0156] More preferably, the Ar a Selected from one of the following groups:

[0157]

[0158]

[0159] Preferably, the R 11 R 12Independently selected from hydrogen, deuterium, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornel, canyl, vinyl, propenyl, butadienyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, phenyl, pentadeuterated phenyl, deuterated naphthyl, deuterated biphenyl, tolyl, biphenyl, terphenyl, naphthyl, anthraceneyl, One of phenanthrene, phenylene, spirofluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-phenylcarbazolyl, dibenzothiophene, dibenzofuranyl, deuterated anthracene, deuterated phenanthrene, deuterated phenylene, deuterated spirofluorenyl, deuterated 9,9-dimethylfluorenyl, deuterated 9,9-diphenylfluorenyl, deuterated 9-phenylcarbazolyl, deuterated dibenzothiophene, and deuterated dibenzofuranyl.

[0160] More preferably, the R 11 R 12 Independently selected from hydrogen, deuterium, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornel, canyl, or one of the following groups:

[0161]

[0162] Preferably, the R 22 It is selected from one of hydrogen, deuterium, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornel, canyl, phenyl, pentadeuterated phenyl, deuterated naphthyl, deuterated biphenyl, tolyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, stilbene, spirofluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-phenylcarbazolyl, dibenzothiophene, dibenzofuranyl, deuterated spirofluorenyl, deuterated 9,9-dimethylfluorenyl, deuterated 9,9-diphenylfluorenyl, deuterated 9-phenylcarbazolyl, deuterated dibenzothiophene, and deuterated dibenzofuranyl.

[0163] More preferably, the R 22 Selected from hydrogen, deuterium, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornyl, canyl, or one of the following groups:

[0164]

[0165] Preferably, the R 22 With R 22 They connect to form one of the following adipose rings:

[0166]

[0167] Preferably, the L a ~L c Independently selected from a single bond or one of the following groups:

[0168]

[0169] More preferably, the L a ~L c Independently selected from a single bond or one of the following groups:

[0170]

[0171]

[0172] Preferably, the fluorene-containing triarylamine compound is selected from any one of the following chemical structures:

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187] In the organic electroluminescent element of this invention, the light-emitting layer material includes a host material and a guest material. The host material can be selected from tris(8-hydroxyquinoline)aluminum (Alq3), 4,4'-N,N'-dicarbazole-biphenyl (CBP), 4,4-bis(9-carbazolyl)biphenyl (CPB), 9,10-bis(2-naphthyl)anthracene (ADN), 9,9'-(1,3-phenyl)bis-9H-carbazole (mCP), 1,3,5-tris(9-carbazolyl)benzene (TCP), poly(N-vinylcarbazole) (PVK), 9,10-bis(naphthyl-2-yl)anthracene (ADN), 4,4' ... Tris(N-carbazole)triphenylamine (TCTA), 1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene (TPBI), 3-tert-butyl-9,10-di(naphthyl-2-yl)anthracene (TBADN), stilbene aromatics (DSA), 4,4'-bis(9-carbazole)-2,2'-dimethyl-biphenyl (dmCBP), N,N'-di-(1-naphthyl)-N,N'-diphenyl-[1,1':4',1”:4”,1”'-tetraphenyl]-4,4”'-diamino (4PNPB), etc. In addition to the above materials and combinations thereof, any suitable host material can be used as an organic... The main material of the light-emitting element. The doping material of the blue light-emitting layer may, without limitation, include perylene and its derivatives, iridium (Ir) complexes, etc. Examples include (6-(4-(diphenylamino(phenyl)-N,N-diphenylpyrene-1-amine) (abbreviated as: DPAP-DPPA), 2,5,8,11-tetra-tert-butylperylene (abbreviated as: TBPe), 4,4'-bis[4-(diphenylamino)styryl]biphenyl (abbreviated as: BDAVBi), 4,4'-bis[4-(di-p-tolylamino)styryl]biphenyl (abbreviated as: DPAVBi), and bis(2-hydroxyphenylpyridine)beryllium (abbreviated as: Bepp2). The blue emitting layer doping material may include, in addition to the above materials and combinations thereof, other known materials suitable for serving as the emitting layer. The green emitting layer doping material may, without limitation, include coumarins and their derivatives, iridium complexes, etc. Examples include tris(2-phenylpyridine)iridium (Ir(ppy)3) and bis(2-phenylpyridine)iridium acetylacetonate (Ir(ppy)2(acac)). In addition to the above materials and combinations thereof, the green emitting layer doping material may also include other known materials suitable for serving as the emitting layer.Non-limiting examples of the red luminescent layer doping material may include rubrene and its derivatives, iridium complexes, osmium complexes, platinum complexes, etc., with examples selected from 9,10-bis[N-(p-tolyl)anilino]anthracene (TPA), 4-(dicyanomethylene)-2-methyl-6-(4-dimethylaminostyryl)-4H-pyran (DCM), tris[1-phenylisoquinoline-C2,N]iridium(III) (Ir(piq)3), bis(1-phenylisoquinoline)(acetylacetone)iridium (Ir(piq)2(acac)), etc. In addition to the above materials, the red luminescent layer doping material may also include other known materials suitable for use as the luminescent layer.

[0188] The optimal doping ratio of the host material and guest material of the light-emitting layer can vary depending on the material used. Typically, the doping ratio of the guest material of the light-emitting layer is 0.01% to 20%, preferably 0.1% to 15%, and more preferably 1% to 10%.

[0189] In the organic electroluminescent element of this invention, the hole-blocking material has good hole-blocking ability and can block holes within the light-emitting layer. Specific examples of the hole-blocking material include, but are not limited to, the following materials: conjugated aromatic compounds with electron-withdrawing properties, such as imidazole derivatives, phenanthroline derivatives, rare earth complexes, oxazole derivatives, triazole derivatives, and triazine derivatives, for example, 4,7-diphenyl-1,10-phenanthroline (Bphen), 1,3,5-tris(N-phenyl-2-benzimidazole)benzene (TPBi), and bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxyaluminum) (BAlq).

[0190] In the organic electroluminescent element of the present invention, the electron transport material can be selected from 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 1,3,5-tris(N-phenyl-2-benzimidazole)benzene (TPBi), tris(8-hydroxyquinoline)aluminum(III) (Alq3), 8-hydroxyquinoline-lithium (Liq), di(2-methyl-8-hydroxyquinoline)(4-phenylphenol)aluminum(III) (BAlq), 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), 4,7-diphenyl-1,10-phenanthroline (Bphen), etc. In addition to the above materials and combinations thereof, the electron transport material may also include other known materials suitable for electron transport layers.

[0191] In the organic electroluminescent element of this invention, the electron injection material can be selected from Li, Na, K, Rb, Cs, Be, Mg, Ca, lithium fluoride (LiF), sodium fluoride, potassium fluoride, rubidium fluoride, cesium fluoride, magnesium fluoride, calcium fluoride, lithium oxide, cesium carbonate, potassium silicate, lithium acetate, sodium acetate, potassium acetate, lithium tetra(8-hydroxyquinoline)boron, lithium 8-hydroxyquinoline (Liq), etc. Besides the above materials and combinations thereof, the electron injection material may also include other known materials suitable for serving as the electron injection layer. Preferably, the electron injection layer of this invention is selected from lithium fluoride (LiF), lithium 8-hydroxyquinoline (Liq), etc.

[0192] For cathode materials, metals with low work functions are generally preferred for injecting electrons into the electron injection / transport layer or the light-emitting layer. Examples of suitable materials include, for instance, metals such as lithium, sodium, potassium, rubidium, cesium, beryllium, magnesium, calcium, strontium, barium, aluminum, scandium, vanadium, zinc, yttrium, indium, cerium, samarium, europium, terbium, ytterbium, and alloys formed from two or more of these metals, or alloys formed from one or more of these metals with one or more of gold, silver, platinum, copper, manganese, titanium, cobalt, nickel, tungsten, and tin, as well as graphite or graphite interlayer compounds. Examples of alloys include magnesium-silver alloys, magnesium-indium alloys, magnesium-aluminum alloys, indium-silver alloys, lithium-aluminum alloys, lithium-magnesium alloys, lithium-indium alloys, and calcium-aluminum alloys. It should be noted that the cathode can be formed into a multilayer structure with two or more layers. This cathode can be prepared by forming a thin film from these electrode materials using methods such as vapor deposition or sputtering. In addition to the above materials and combinations thereof, other known materials suitable for cathodes may also be used. Preferably, the cathode of the present invention is selected from a semi-transparent cathode, such as thin Ag or Mg-Ag alloy or thin Al.

[0193] When the light-emitting layer is extracted from the cathode, the light transmittance of the cathode is preferably greater than 10%. It is also preferred that the resistivity of the cathode sheet is less than several hundred Ω / □, and the film thickness is typically 10 nm to 500 nm, preferably 10 nm to 100 nm.

[0194] The coating material of the present invention can be any one or a combination of at least two of Alq3, TPBi or other known suitable coating materials.

[0195] The optimal thickness of the hole transport layer and electron transport layer varies depending on the material used. It should be selected based on conditions that allow for appropriate driving voltage and luminous efficiency, but it must be at least thick enough to avoid pinholes. Excessive thickness increases the driving voltage of the device, which is undesirable. Therefore, the thickness of the hole transport layer and electron transport layer is, for example, 1 nm to 1 μm, preferably 2 nm to 500 nm, and more preferably 5 nm to 200 nm. The order and number of layers, as well as the thickness of each layer, of the organic electroluminescent element can be appropriately selected considering luminous efficiency and device lifetime.

[0196] There are no particular limitations on the preparation and formation methods of each layer in the organic electroluminescent element. Any one of the following methods can be used: vacuum evaporation, spin coating, vapor deposition, blade coating, laser thermal transfer, electrospray coating, slot coating, and dip coating. In this invention, vacuum evaporation is preferred.

[0197] The organic electroluminescent element described in this invention can be widely used in panel displays, lighting sources, flexible OLEDs, electronic paper, organic solar cells, organic photosensitive materials or organic thin-film transistors, signs, signal lights and other fields.

[0198] This invention also provides a method for synthesizing the triarylamine derivative represented by formula (Ⅰ), the specific synthetic route of which is shown below:

[0199] 1. When R is a fused ring formed with phenylene, the preparation method is shown in Route 1:

[0200]

[0201] Under a nitrogen atmosphere, amine compound a reacts with halogen compound b via a Buchwald reaction to obtain intermediate A, and boric acid compound c reacts with halogen compound d via a Suzuki reaction to obtain intermediate B. Subsequently, intermediate A and intermediate B react with appropriate catalysts, organic bases, ligands, solutions, and at appropriate temperatures to obtain the corresponding compounds of formula (Ⅰ), wherein halogen compounds X0, X1, and X2 are compounds containing Cl, Br, or I.

[0202] 2. When R is selected from cycloalkyl groups, the preparation method is shown in Route 2:

[0203] [Route 2](i) When both L0 and L1 are single-key bridges:

[0204]

[0205] Under a nitrogen atmosphere, amine compound a reacts with halogen compound b via a Buchwald reaction to give intermediate A. Alcohol compound e-1 reacts with halogen-containing phenol compound f-1 under the conditions of concentrated sulfuric acid and dichloromethane to generate intermediate C-1, which then reacts with boric acid compound c to give intermediate D-1. Intermediate D-1 reacts with dichloromethane, pyridine, and trifluoromethanesulfonic anhydride to generate intermediate F-1. Subsequently, intermediate A and intermediate F-1 react under the appropriate catalyst, organic base, ligand, solution, and temperature to obtain the corresponding compound of formula (Ⅰ), wherein halogen compound X3 is a compound containing Cl, Br, or I.

[0206] (ii) When the bridge L0 is a single bond and L1 is not a single bond, or L0 is not a single bond and L1 is a single bond, or neither L0 nor L1 is a single bond:

[0207]

[0208] Under a nitrogen atmosphere, amine compound a reacts with halogen compound b via a Buchwald reaction to give intermediate A. Alcohol compound e-1 reacts with halogen-containing phenol compound f'-1 under the conditions of concentrated sulfuric acid and dichloromethane to generate intermediate C'-1, which then reacts with boric acid compound c'-1 to give intermediate D'-1. Intermediate D'-1 reacts with dichloromethane, pyridine, and trifluoromethanesulfonic anhydride to generate intermediate F'-1. Subsequently, intermediate A and intermediate F'-1 react under the appropriate catalyst, organic base, ligand, solution, and temperature to obtain the corresponding compound of formula (Ⅰ), wherein halogen compound X3 is a compound containing Cl, Br, or I.

[0209] This invention also provides a method for synthesizing the fluorene-containing triarylamine compound represented by formula (II), the specific synthetic route of which is shown below:

[0210]

[0211] Under a nitrogen atmosphere, boric acid compound c-2 reacts with halogen compound d-2 via the Suzuki reaction to give intermediate B-2. Amine compound b-2 reacts with halogen compound a-2 via the Buchwald reaction to give intermediate A-2. Subsequently, intermediate A-2 reacts with intermediate B-2 under appropriate catalysts, organic bases, ligands, solutions, and temperatures to obtain the corresponding compound of formula (II), wherein halogen compound X... a X b X c Such as compounds containing Cl, Br or I.

[0212] This invention does not impose any particular restrictions on the source of the raw materials used in the above-described reactions; commercially available raw materials or preparation methods well known to those skilled in the art can be used. This invention also does not impose any particular restrictions on the above reactions; conventional reactions well known to those skilled in the art can be used.

[0213] The invention is explained in more detail through the following examples, but is not intended to limit the invention. Based on this description, those skilled in the art will be able to practice the invention and prepare other compounds and elements according to the invention within the entire scope disclosed without inventive effort.

[0214] Description of raw materials, reagents, and characterization equipment:

[0215] The present invention does not impose any particular restrictions on the source of raw materials used in the following embodiments, which can be commercially available products or prepared using preparation methods well known to those skilled in the art.

[0216] Mass spectrometry was performed using a Waters G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer, with chloroform as the solvent.

[0217] Elemental analysis was performed using a Vario EL cube organic elemental analyzer from Elementar GmbH, Germany, with sample masses ranging from 5 to 10 mg.

[0218] [Synthesis Example 1] Synthesis of Compound 1

[0219]

[0220] Synthetic intermediate A-1

[0221] Under nitrogen protection, starting materials a-1 (8.46 g, 50.00 mmol), b-1 (15.46 g, 50.00 mmol), palladium acetate (0.18 g, 0.80 mmol), sodium tert-butoxide (8.46 g, 88.00 mmol), tri-tert-butylphosphine (3.5 mL of 1.0 M toluene solution), and toluene (550 mL) were added to a reaction flask and reacted under reflux for 3 h. After the reaction was complete, the mixture was cooled to room temperature, filtered with diatomaceous earth, the filtrate was concentrated, and then recrystallized from toluene. The recrystallized solid was obtained by vacuum filtration, which was intermediate A-1 (15.50 g, yield 78%). HPLC analysis showed that the solid purity was ≥99.35%. Mass spectrometry m / z: 397.1841 (theoretical value: 397.1830).

[0222] Synthetic intermediate B-1

[0223] Under nitrogen protection, starting materials c-1 (11.49 g, 40.00 mmol), d-1 (9.26 g, 40.00 mmol), Pd(PPh3)4 (0.92 g, 0.80 mmol), K2CO3 (10.78 g, 78.00 mmol), 225 mL toluene, 75 mL ethanol, and 75 mL water were added sequentially to a reaction flask. The mixture was stirred and refluxed for 3.5 h. After the reaction was completed, the mixture was cooled to room temperature, filtered to obtain a filter cake, and washed with ethanol. Finally, the filter cake was recrystallized from toluene / ethanol at a ratio of 4:1 to obtain intermediate B-1 (12.76 g, yield 81%). HPLC analysis showed that the solid purity was ≥99.67%. Mass spectrometry m / z: 393.1296 (theoretical value: 393.1284).

[0224] Synthetic compound 1

[0225] Under nitrogen protection, toluene solvent (500 mL), intermediates B-1 (11.82 g, 30.00 mmol), A-1 (11.93 g, 30.00 mmol), Pd(dba)2 (5.75 g, 10.00 mmol), sodium tert-butoxide (5.09 g, 53.00 mmol), and BINAP (0.56 g, 0.90 mmol) were added sequentially to a 1 L reaction flask, and the reaction was heated for 6 h. After the reaction was completed, the mixture was cooled to room temperature, ice water was added to precipitate the solid product, and the product was filtered. The product was then purified by silica gel column chromatography (petroleum ether / ethyl acetate = 8:1) to give compound 1 (16.31 g, yield 72%). HPLC analysis showed that the solid purity was ≥99.94%. Mass spectrometry m / z: 754.3339 (theoretical value: 754.3348). Theoretical elemental content (%) C 57 H 42 N2: C, 90.68; H, 5.61; N, 3.71. Measured elemental content (%): C, 90.65; H, 5.63; N, 3.69.

[0226] [Synthesis Example 2] Synthesis of Compound 18

[0227]

[0228] Compound 1 was synthesized using the same method as in Example 1, except that a-1 was replaced with an equimolar amount of a-18 and b-1 was replaced with an equimolar amount of b-18. Compound 18 (15.39 g) was synthesized, and the solid purity was ≥99.98% as determined by HPLC. Mass spectrometry m / z: 683.3358 (theoretical value: 683.3349). Theoretical elemental content (%) C 51 H 33 D5N2: C, 89.57; H, 6.34; N, 4.10. Measured elemental content (%): C, 89.60; H, 6.33; N, 4.12.

[0229] [Synthesis Example 3] Synthesis of Compound 46

[0230]

[0231] Compound 1 was synthesized using the same method as in Example 1, except that a-1 was replaced with an equimolar amount of a-46 and b-1 was replaced with an equimolar amount of b-46. Compound 46 (16.03 g) was synthesized, and the solid purity was ≥99.95% as determined by HPLC. Mass spectrometry m / z: 741.4145 (theoretical value: 741.4131). Theoretical elemental content (%) C 55 H 43D5N2: C, 89.03; H, 7.20; N, 3.78. Measured elemental content (%): C, 89.04; H, 7.23; N, 3.76.

[0232] [Synthesis Example 4] Synthesis of Compound 58

[0233]

[0234] Compound 1 was synthesized using the same method as in Example 1, except that b-1 was replaced with an equimolar amount of b-58, resulting in compound 58 (16.61 g). HPLC analysis showed a solid purity ≥ 99.91%. Mass spectrometry m / z: 790.4278 (theoretical value: 790.4287). Theoretical elemental content (%) C 59 H 54 N2: C, 89.58; H, 6.88; N, 3.54. Measured elemental content (%): C, 89.55; H, 6.90; N, 3.53.

[0235] [Synthesis Example 5] Synthesis of Compound 81

[0236]

[0237] Compound 1 was synthesized using the same method as in Example 1, except that a-1 was replaced with an equimolar amount of a-81 and b-1 was replaced with an equimolar amount of b-81. Compound 81 (16.59 g) was synthesized, and the solid purity was ≥99.93% as determined by HPLC. Mass spectrometry m / z: 778.3356 (theoretical value: 778.3348). Theoretical elemental content (%) C 59 H 42 N2: C, 90.97; H, 5.43; N, 3.60. Measured elemental content (%): C, 90.99; H, 5.46; N, 3.57.

[0238] [Synthesis Example 6] Synthesis of Compound 84

[0239]

[0240] Compound 1 was synthesized using the same method as in Example 1, except that a-1 was replaced with an equimolar amount of a-84, b-1 with an equimolar amount of b-84, and c-1 with an equimolar amount of c-84. Compound 84 (16.12 g) was synthesized, and the solid purity was ≥99.95% as determined by HPLC. Mass spectrometry m / z: 735.3644 (theoretical value: 735.3631). Theoretical elemental content (%) C 55 H 33D7N2: C, 89.76; H, 6.44; N, 3.81. Measured elemental content (%): C, 89.78; H, 6.43; N, 3.83.

[0241] [Synthesis Example 7] Synthesis of Compound 97

[0242]

[0243] Compound 1 was synthesized using the same method as in Example 1, except that a-1 was replaced with an equimolar amount of a-97 and b-1 was replaced with an equimolar amount of b-97. Compound 97 (18.50 g) was synthesized, and the solid purity was ≥99.84% as determined by HPLC. Mass spectrometry m / z: 933.4123 (theoretical value: 933.4131). Theoretical elemental content (%) C 71 H 43 D5N2: C, 91.28; H, 5.72; N, 3.00. Measured elemental content (%): C, 91.29; H, 5.75; N, 2.98.

[0244] [Synthesis Example 8] Synthesis of Compound 138

[0245]

[0246] Synthetic C-138

[0247] Under an argon atmosphere, 400 mL of dehydrated tetrahydrofuran was added to the starting material e-138 (37.23 g, 100.00 mmol), and the reaction solution was cooled to -40 °C. 63 mL (100.00 mmol) of a 1.6 M n-butyllithium solution in hexane was slowly added. The reaction solution was heated to 0 °C and stirred for 1 h, then cooled again to -78 °C. 50 mL of a dehydrated tetrahydrofuran solution of trimethyl borate (25.98 g, 250.00 mmol) was added dropwise, and the reaction solution was stirred at room temperature for 5 h. 200 mL of 1 M hydrochloric acid was added, and after stirring for 1 h, the aqueous layer was removed. The organic layer was dried with MgSO4, and the solvent was removed by vacuum distillation. The resulting solid was washed with toluene to obtain c-138 (27.31 g, yield 81%), with a solid purity ≥99.57% as determined by HPLC. Mass spectrometry m / z: 337.1283 (theoretical value: 337.1274).

[0248] Synthetic compound 138

[0249] Compound 1 was synthesized using the same method as in Example 1, except that a-1 was replaced with an equimolar amount of a-138, b-1 with an equimolar amount of b-138, and c-1 with an equimolar amount of c-138, resulting in compound 138 (17.20 g). HPLC analysis showed a solid purity ≥ 99.91%. Mass spectrometry m / z: 818.3670 (theoretical value: 818.3661). Theoretical elemental content (%) C 62 H 46 N2: C, 90.92; H, 5.66; N, 3.42. Measured element content (%): C, 90.94; H, 5.67; N, 3.41.

[0250] [Synthesis Example 9] Synthesis of Compound 141

[0251]

[0252]

[0253] The same synthesis method as that used for c-138 in Synthesis Example 8 was employed, except that e-138 was replaced with an equimolar amount of e-141 to synthesize c-141 (24.25 g). The purity of the solid was determined by HPLC to be ≥99.62%. Mass spectrometry m / z: 292.1440 (theoretical value: 292.1431).

[0254] Compound 1 was synthesized using the same method as in Example 1, except that a-1 was replaced with an equimolar amount of a-141, b-1 with an equimolar amount of b-141, and c-1 with an equimolar amount of c-141. Compound 141 (15.51 g) was synthesized, and the solid purity was ≥99.96% as determined by HPLC. Mass spectrometry m / z: 707.4238 (theoretical value: 707.4226). Theoretical elemental content (%) C 52 H 37 D9N2: C, 88.22; H, 7.83; N, 3.96. Measured elemental content (%): C, 88.24; H, 7.85; N, 3.95.

[0255] [Synthesis Example 10] Synthesis of Compound 147

[0256]

[0257] Compound 141 (17.45 g) was synthesized using the same method as in Synthesis Example 1, except that b-1 was replaced with an equimolar amount of b-147. HPLC analysis showed a solid purity ≥ 99.88%. Mass spectrometry m / z: 842.3672 (theoretical value: 842.3661). Theoretical elemental content (%) C 64 H 46N2: C, 91.18; H, 5.50; N, 3.32. Measured element content (%): C, 91.20; H, 5.49; N, 3.34.

[0258] [Synthesis Example 11] Synthesis of Compound 163

[0259]

[0260] The same synthesis method as that used for c-138 in Synthesis Example 8 was employed, except that e-138 was replaced with an equimolar amount of e-163 to synthesize c-163 (27.80 g). The purity of the solid was determined by HPLC to be ≥99.55%. Mass spectrometry m / z: 343.1752 (theoretical value: 343.1744).

[0261] Compound 1 was synthesized using the same method as in Example 1, except that b-1 was replaced with an equimolar amount of b-163 and c-1 was replaced with an equimolar amount of c-163, resulting in compound 163 (17.69 g). HPLC analysis showed a solid purity ≥ 99.86%. Mass spectrometry m / z: 866.4612 (theoretical value: 866.4600). Theoretical elemental content (%) C 65 H 58 N2: C, 90.03; H, 6.74; N, 3.23. Measured elemental content (%): C, 90.04; H, 6.71; N, 3.24.

[0262] [Synthesis Example 12] Synthesis of Compound 164

[0263]

[0264] The same synthesis method as that used for c-138 in Synthesis Example 8 was employed, except that e-138 was replaced with an equimolar amount of e-164 to synthesize c-164 (27.65 g). The purity of the solid was determined by HPLC to be ≥99.53%. Mass spectrometry m / z: 337.1285 (theoretical value: 337.1274).

[0265] Compound 1 was synthesized using the same method as in Example 1, except that b-1 was replaced with an equimolar amount of b-164 and c-1 was replaced with an equimolar amount of c-164, resulting in compound 164 (18.15 g). HPLC analysis showed a solid purity ≥ 99.85%. Mass spectrometry m / z: 902.4616 (theoretical value: 902.4600). Theoretical elemental content (%) C 68 H 58 N2: C, 90.43; H, 6.47; N, 3.10. Measured elemental content (%): C, 90.45; H, 6.48; N, 3.08.

[0266] [Synthesis Example 13] Synthesis of Compound 167

[0267]

[0268] The same synthesis method as that used for c-138 in Synthesis Example 8 was employed, except that e-138 was replaced with an equimolar amount of e-167 to synthesize c-167 (29.06 g). The purity of the solid was determined by HPLC to be ≥99.52%. Mass spectrometry m / z: 363.1442 (theoretical value: 363.1431).

[0269] Compound 1 was synthesized using the same method as in Example 1, except that b-1 was replaced with an equimolar amount of b-167, c-1 with an equimolar amount of c-167, and d-1 with an equimolar amount of d-167. Compound 167 (18.68 g) was synthesized, and the solid purity was ≥99.83% as determined by HPLC. Mass spectrometry m / z: 942.4764 (theoretical value: 942.4758). Theoretical elemental content (%) C 71 H 42 D 10 N2: C, 90.41; H, 6.62; N, 2.97. Measured elemental content (%): C, 90.43; H, 6.63; N, 2.95.

[0270] [Synthesis Example 14] Synthesis of Compound 175

[0271]

[0272] Compound 1 was synthesized using the same method as in Example 1, except that a-1 was replaced with an equimolar amount of a-175, b-1 with an equimolar amount of b-175, and c-1 with an equimolar amount of c-175. Compound 175 (18.07 g) was synthesized, and the solid purity was ≥99.84% as determined by HPLC. Mass spectrometry m / z: 898.4276 (theoretical value: 898.4287). Theoretical elemental content (%) C 68 H 54 N2: C, 90.83; H, 6.05; N, 3.12. Measured elemental content (%): C, 90.82; H, 6.06; N, 3.14.

[0273] [Synthesis Example 15] Synthesis of Compound 200

[0274]

[0275] Compound 1 was synthesized using the same method as in Example 1, except that a-1 was replaced with an equimolar amount of a-200 and b-1 was replaced with an equimolar amount of b-200, resulting in compound 200 (19.67 g). HPLC analysis showed a solid purity ≥ 99.82%. Mass spectrometry m / z: 992.5082 (theoretical value: 992.5070). Theoretical elemental content (%) C 75 H 64 N2: C, 90.69; H, 6.49; N, 2.82. Measured element content (%): C, 90.72; H, 6.48; N, 2.84.

[0276] [Synthesis Example 16] Synthesis of Compound 210

[0277]

[0278] The same synthesis method as that used for c-138 in Synthesis Example 8 was employed, except that e-138 was replaced with an equimolar amount of e-210 to synthesize c-210 (30.15 g). The purity of the solid was determined by HPLC to be ≥99.51%. Mass spectrometry m / z: 363.1445 (theoretical value: 363.1431).

[0279] Compound 1 was synthesized using the same method as in Example 1, except that b-1 was replaced with an equimolar amount of b-210 and c-1 was replaced with an equimolar amount of c-210, resulting in compound 210 (19.37 g). HPLC analysis showed a solid purity ≥ 99.81%. Mass spectrometry m / z: 992.4119 (theoretical value: 992.4130). Theoretical elemental content (%) C 76 H 52 N2: C, 91.90; H, 5.28; N, 2.82. Measured elemental content (%): C, 91.95; H, 5.24; N, 2.84.

[0280] [Synthesis Example 17] Synthesis of Compound 215

[0281]

[0282] Compound 1 was synthesized using the same method as in Synthesis Example 1, except that a-1 was replaced with an equimolar amount of a-215 and b-1 was replaced with an equimolar amount of b-215, resulting in compound 215 (16.70 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 772.3463 (theoretical value: 772.3454). Theoretical elemental content (%) C 57 H 44 N₂O: C, 88.57; H, 5.74; N, 3.62. Measured elemental content (%): C, 88.54; H, 5.79; N, 3.61.

[0283] [Synthesis Example 18] Synthesis of Compound 220

[0284]

[0285] Compound 220 (16.84 g) was synthesized using the same method as in Synthesis Example 1, except that b-1 was replaced with an equimolar amount of b-220. The solid purity was determined by HPLC to be ≥99.95%. Mass spectrometry m / z: 768.3153 (theoretical value: 768.3141). Theoretical elemental content (%) C 57 H 40 N₂O: C, 89.03; H, 5.24; N, 3.64. Measured elemental content (%): C, 89.02; H, 5.28; N, 3.65.

[0286] [Synthesis Example 19] Synthesis of Compound 241

[0287]

[0288] Compound 241 (16.49 g) was synthesized using the same method as in Synthesis Example 1, except that b-1 was replaced with an equimolar amount of b-241. The solid purity was determined by HPLC to be ≥99.96%. Mass spectrometry m / z: 742.2971 (theoretical value: 742.2984). Theoretical elemental content (%) C 55 H 38 N₂O: C, 88.92; H, 5.16; N, 3.77. Measured elemental content (%): C, 88.94; H, 5.17; N, 3.75.

[0289] [Synthesis Example 20] Synthesis of Compound 254

[0290]

[0291] The same synthesis method as that used for c-138 in Synthesis Example 8 was employed, except that e-138 was replaced with an equimolar amount of e-254 to synthesize c-254 (29.42 g). The purity of the solid was determined by HPLC to be ≥99.60%. Mass spectrometry m / z: 363.1422 (theoretical value: 363.1431).

[0292] Compound 1 was synthesized using the same method as in Example 1, except that a-1 was replaced with an equimolar amount of a-254, b-1 with an equimolar amount of b-254, and c-1 with an equimolar amount of c-254, to synthesize compound 254 (17.00 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 786.3198 (theoretical value: 786.3184). Theoretical elemental content (%) C 57 H 34 D4N2O2: C, 87.00; H, 5.38; N, 3.56. Measured elemental content (%): C, 87.04; H, 5.36; N, 3.57.

[0293] [Synthesis Example 21] Synthesis of Compound 260

[0294]

[0295] Compound 260 (16.72 g) was synthesized using the same method as in Synthesis Example 1, except that b-1 was replaced with an equimolar amount of b-260. The solid purity was determined by HPLC to be ≥99.92%. Mass spectrometry m / z: 784.2922 (theoretical value: 784.2912). Theoretical elemental content (%) C 57 H 40 N₂S: C, 87.21; H, 5.14; N, 3.57. Measured elemental content (%): C, 87.24; H, 5.16; N, 3.53.

[0296] [Synthesis Example 22] Synthesis of Compound 328

[0297]

[0298] The same synthesis method as that used for c-138 in Synthesis Example 8 was employed, except that e-138 was replaced with an equimolar amount of e-328 to synthesize c-328 (26.83 g). The purity of the solid was determined by HPLC to be ≥99.63%. Mass spectrometry m / z: 327.1419 (theoretical value: 327.1431).

[0299] Compound 1 was synthesized using the same method as in Example 1, except that b-1 was replaced with an equimolar amount of b-328 and c-1 was replaced with an equimolar amount of c-328, resulting in compound 328 (16.62 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 758.3675 (theoretical value: 758.3661). Theoretical elemental content (%) C 57 H 46 N2: C, 90.20; H, 6.11; N, 3.69. Measured elemental content (%): C, 90.23; H, 6.09; N, 3.67.

[0300] [Synthesis Example 23] Synthesis of Compound 379

[0301]

[0302] Compound 1 was synthesized using the same method as in Example 1, except that b-1 was replaced with an equimolar amount of b-379, resulting in compound 379 (17.22 g). HPLC analysis showed a solid purity ≥ 99.87%. Mass spectrometry m / z: 843.3627 (theoretical value: 843.3613). Theoretical elemental content (%) C 63 H 45 N3: C, 89.65; H, 5.37; N, 4.98. Measured elemental content (%): C, 89.62; H, 5.38; N, 4.96.

[0303] [Synthesis Example 24] Synthesis of Compound 416

[0304]

[0305] Compound 1 was synthesized using the same method as in Example 1, except that b-1 was replaced with an equimolar amount of b-416, resulting in compound 416 (17.23 g). HPLC analysis showed a solid purity ≥ 99.86%. Mass spectrometry m / z: 856.3436 (theoretical value: 856.3454). Theoretical elemental content (%) C 64 H 44 N₂O: C, 89.69; H, 5.17; N, 3.27. Measured elemental content (%): C, 89.67; H, 5.20; N, 3.23.

[0306] [Synthesis Example 25] Synthesis of Compound 452

[0307]

[0308] The same synthesis method as that used for c-138 in Synthesis Example 8 was employed, except that e-138 was replaced with an equimolar amount of e-452 to synthesize c-452 (23.58 g). The purity of the solid was determined by HPLC to be ≥99.58%. Mass spectrometry m / z: 291.1358 (theoretical value: 291.1369).

[0309] Compound 1 was synthesized using the same method as in Example 1, except that b-1 was replaced with an equimolar amount of b-452 and c-1 was replaced with an equimolar amount of c-452. Compound 452 (15.42 g) was synthesized, and the solid purity was ≥99.93% as determined by HPLC. Mass spectrometry m / z: 723.3176 (theoretical value: 723.3188). Theoretical elemental content (%) C 52 H33 D4N3O: C, 86.28; H, 5.71; N, 5.80. Measured elemental content (%): C, 86.29; H, 5.75; N, 5.78.

[0310] [Synthesis Example 26] Synthesis of Compound 461

[0311]

[0312] Compound 1 was synthesized using the same method as in Example 1, except that b-1 was replaced with an equimolar amount of b-461 and d-1 was replaced with an equimolar amount of d-167, resulting in compound 461 (17.49 g). HPLC analysis showed a solid purity ≥ 99.86%. Mass spectrometry m / z: 856.3826 (theoretical value: 856.3817). Theoretical elemental content (%) C 65 H 48 N2: C, 91.09; H, 5.64; N, 3.27. Measured elemental content (%): C, 91.07; H, 5.63; N, 3.28.

[0313] [Synthesis Example 27] Synthesis of Compound 489

[0314]

[0315] Compound 1 was synthesized using the same method as in Synthesis Example 1, except that a-1 was replaced with an equimolar amount of a-489 and b-1 was replaced with an equimolar amount of b-489, resulting in compound 489 (18.22 g). HPLC analysis showed a solid purity ≥ 99.83%. Mass spectrometry m / z: 919.4865 (theoretical value: 919.4852). Theoretical elemental content (%) C 69 H 45 D9N2: C, 90.06; H, 6.90; N, 3.04. Measured elemental content (%): C, 90.04; H, 6.91; N, 3.07.

[0316] [Synthesis Example 28] Synthesis of Compound 518

[0317]

[0318] Compound 1 was synthesized using the same method as in Example 1, except that b-1 was replaced with an equimolar amount of b-518, resulting in compound 518 (17.78 g). HPLC analysis showed a solid purity ≥ 99.89%. Mass spectrometry m / z: 858.3233 (theoretical value: 858.3246). Theoretical elemental content (%) C 63 H 42N2O2: C, 88.09; H, 4.93; N, 3.26. Measured elemental content (%): C, 88.05; H, 4.91; N, 3.28.

[0319] Synthetic intermediate F-1-1

[0320]

[0321] Synthetic intermediate C-1-1:

[0322] Under nitrogen protection, g-1-1 (13.70 g, 90.00 mmol), f-1-1 (15.57 g, 90.00 mmol), and 150 mL of dichloromethane were added to a reaction flask and stirred at room temperature until dissolved. The mixture was then cooled to 15 °C, kept at this temperature, and concentrated sulfuric acid was added dropwise. After the addition was complete, the reaction was maintained at this temperature for 2 hours. After the reaction was completed, the mixture was quenched with water, separated, extracted, washed with water, dried, filtered, and concentrated. Recrystallization with a mixed solvent of dichloromethane and n-heptane, followed by drying, yielded intermediate C-1-1 (22.12 g, 80% yield). HPLC analysis showed a solid purity ≥ 95.76%. Mass spectrometry m / z: 306.0602 (theoretical value: 306.0619).

[0323] Synthetic intermediate D-1-1:

[0324] Under nitrogen protection, intermediates C-1-1 (18.43 g, 60.00 mmol), c-1 (17.23 g, 60.00 mmol), 110 mL toluene, 37 mL ethanol, 37 mL water, and potassium carbonate (16.59 g, 120.00 mmol) were added to a reaction flask and stirred thoroughly. The mixture was heated to 50 °C, and tetrakis(triphenylphosphine)palladium (0.35 g, 0.30 mmol) was quickly added. The mixture was then refluxed at 70 °C for 3 h. After the reaction was complete, the mixture was cooled to room temperature, extracted with dichloromethane, washed with water, dried, filtered, and concentrated. Recrystallization with a mixed solvent of dichloromethane and n-heptane, followed by drying, yielded intermediate D-1-1 (21.41 g, 76% yield). HPLC analysis showed a solid purity ≥97.85%. Mass spectrometry m / z: 469.2419 (theoretical value 469.2406).

[0325] Synthetic intermediate F-1-1:

[0326] Under nitrogen protection, intermediate D-1-1 (21.13 g, 45.00 mmol), 135 mL of dichloromethane, and pyridine (10.68 g, 135.00 mmol) were added to a reaction flask and stirred at room temperature until dissolved and clear. The mixture was then cooled to -5 °C, and trifluoromethanesulfonic anhydride (19.06 g, 67.55 mmol) was added dropwise while maintaining the temperature. After the addition was complete, the reaction was maintained at this temperature for 2 h. After the reaction was completed, the mixture was quenched with water, extracted with dichloromethane, washed with water, dried, filtered, and concentrated. Recrystallization with a mixed solvent of dichloromethane and n-heptane and drying yielded intermediate F-1-1 (19.22 g, yield 71%). HPLC analysis showed a solid purity ≥ 98.62%. Mass spectrometry m / z: 601.1913 (theoretical value: 601.1898).

[0327] Intermediate F-1-2 was synthesized using the intermediate F-1-1 synthesis method.

[0328]

[0329] The following intermediate F-1-3 was synthesized using the intermediate F-1-1 synthesis method.

[0330]

[0331] Intermediate F-1-4 was synthesized using the intermediate F-1-1 synthesis method.

[0332]

[0333] Intermediate F-1-5 was synthesized using the intermediate F-1-1 synthesis method.

[0334]

[0335] Intermediate F-1-6 was synthesized using the intermediate F-1-1 synthesis method.

[0336]

[0337] [Synthesis Example 29] Synthesis of Compound 1-1

[0338]

[0339] Synthetic intermediate A-1-1

[0340] Under nitrogen protection, a-1 (7.62 g, 45 mmol), b-46 (13.11 g, 45 mmol), palladium acetate (0.16 mg, 0.70 mmol), sodium tert-butoxide (7.69 g, 80 mmol), tri-tert-butylphosphine (5 mL of 1.0 M toluene solution), and toluene (500 mL) were added to a reaction flask and reacted under reflux for 2 h. After the reaction was complete, the mixture was cooled to room temperature, filtered with diatomaceous earth, the filtrate was concentrated, and then recrystallized from toluene. The recrystallized solid was obtained by vacuum filtration, which was intermediate A-1-1 (13.15 g, yield 77%). The purity of the solid was ≥99.79% as determined by HPLC. Mass spectrometry m / z: 379.2317 (theoretical value: 379.2300).

[0341] Synthetic compound 1-1

[0342] Under nitrogen protection, toluene solvent (500 mL), intermediate A-1-1 (11.39 g, 30.00 mmol), intermediate F-1-1 (18.05 g, 30.00 mmol), Pd(dba)2 (5.75 g, 10.00 mmol), sodium tert-butoxide (5.09 g, 53.00 mmol), and x-phos (0.38 g, 0.90 mmol) were added to a reaction flask, and the reaction was heated for 6 h. After the reaction was completed, the mixture was cooled to room temperature, ice water was added to precipitate the solid product, and the product was filtered. The product was then purified by silica gel column chromatography (petroleum ether / ethyl acetate = 7:1) to give compound 1-1 (16.96 g, yield 68%). HPLC analysis showed that the solid purity was ≥99.92%. Mass spectrometry m / z: 830.4613 (theoretical value: 830.4600). Theoretical elemental content (%) C 62 H 58 N2: C, 89.60; H, 7.03; N, 3.37. Measured elemental content (%): C, 89.57; H, 6.99; N, 3.42.

[0343] [Synthesis Example 30] Synthesis of compounds 1-26

[0344]

[0345] Compound 1-1 was synthesized using the same method as in Synthesis Example 29, except that b-46 was replaced with an equimolar amount of b-1-26. Compound 1-26 (16.57 g) was synthesized, and the solid purity was ≥99.94% as determined by HPLC. Mass spectrometry m / z: 777.4141 (theoretical value: 777.4131). Theoretical elemental content (%) C 58 H 43 D5N2: C, 89.53; H, 6.87; N, 3.60. Measured elemental content (%): C, 89.49; H, 6.91; N, 3.57.

[0346] [Synthesis Example 31] Synthesis of compounds 1-34

[0347]

[0348] Compound 1-1 was synthesized using the same method as in Synthesis Example 29, except that b-46 was replaced with an equimolar amount of b-1-34. Compound 1-34 (16.22 g) was synthesized, and the solid purity was ≥99.95% as determined by HPLC. Mass spectrometry m / z: 750.3962 (theoretical value: 750.3974). Theoretical elemental content (%) C 56 H 50 N2: C, 89.56; H, 6.71; N, 3.73. Measured elemental content (%): C, 89.61; H, 6.68; N, 3.69.

[0349] [Synthesis Example 32] Synthesis of compounds 1-66

[0350]

[0351] The same method as used in Synthesis Example 29 was used to synthesize compound 1-1, except that a-1 was replaced with an equimolar amount of a-81 and b-46 was replaced with an equimolar amount of b-1-66. Compound 1-66 (17.55 g) was synthesized, and the solid purity was ≥99.90% as determined by HPLC. Mass spectrometry m / z: 872.4112 (theoretical value: 872.4130). Theoretical elemental content (%) C 66 H 52 N2: C, 90.79; H, 6.00; N, 3.21. Measured elemental content (%): C, 90.82; H, 5.97; N, 3.18.

[0352] [Synthesis Example 33] Synthesis of Compounds 1-71

[0353]

[0354] Compound 1-1 was synthesized using the same method as in Synthesis Example 29, except that b-46 was replaced with an equimolar amount of b-1-71. Compound 1-71 (17.29 g) was synthesized, and the solid purity was ≥99.89% as determined by HPLC. Mass spectrometry m / z: 872.4115 (theoretical value: 872.4130). Theoretical elemental content (%) C 66 H 52 N2: C, 90.79; H, 6.00; N, 3.21. Measured elemental content (%): C, 90.83; H, 5.98; N, 3.17.

[0355] [Synthesis Example 34] Synthesis of Compounds 1-104

[0356]

[0357] Compound 1-104 (16.83 g) was synthesized using the same method as in Synthesis Example 29, except that intermediate A-1-1 was replaced with an equimolar amount of intermediate A-328. HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 812.4144 (theoretical value: 812.4130). Theoretical elemental content (%) C 61 H 52 N2: C, 90.11; H, 6.45; N, 3.45. Measured elemental content (%): C, 90.09; H, 6.50; N, 3.39.

[0358] [Synthesis Example 35] Synthesis of Compounds 1-126

[0359]

[0360] The same method as in Synthesis Example 29 was used to synthesize compound 1-1, except that b-46 was replaced with an equimolar amount of b-1-126. Compound 1-126 (17.33 g) was synthesized, and the solid purity was ≥99.89% as determined by HPLC. Mass spectrometry m / z: 874.4299 (theoretical value: 874.4287). Theoretical elemental content (%) C 66 H 54 N2: C, 90.58; H, 6.22; N, 3.20. Measured elemental content (%): C, 90.62; H, 6.17; N, 3.18.

[0361] [Synthesis Example 36] Synthesis of Compounds 1-146

[0362]

[0363] The same method as in Example 29 was used to synthesize compound 1-1, except that b-46 was replaced with an equimolar amount of b-1-146. Compound 1-146 (18.85 g) was synthesized, and the solid purity was ≥99.87% as determined by HPLC. Mass spectrometry m / z: 1012.4739 (theoretical value: 1012.4756). Theoretical elemental content (%) C 77 H 60 N2: C, 91.27; H, 5.97; N, 2.76. Measured elemental content (%): C, 91.32; H, 6.01; N, 2.71.

[0364] [Synthesis Example 37] Synthesis of Compounds 1-164

[0365]

[0366] The same method as in Example 29 was used to synthesize compound 1-1, except that b-46 was replaced with an equimolar amount of b-1-164. Compound 1-164 (18.77 g) was synthesized, and the solid purity was ≥99.85% as determined by HPLC. Mass spectrometry m / z: 992.5061 (theoretical value: 992.5070). Theoretical elemental content (%) C 75 H 64 N2: C, 90.69; H, 6.49; N, 2.82. Measured element content (%): C, 90.73; H, 6.51; N, 2.79.

[0367] [Synthesis Example 38] Synthesis of Compounds 1-181

[0368]

[0369] The same method as in Synthesis Example 29 was used to synthesize compound 1-1, except that b-46 was replaced with an equimolar amount of b-1-181. Compound 1-181 (19.25 g) was synthesized, and the solid purity was ≥99.83% as determined by HPLC. Mass spectrometry m / z: 1068.5393 (theoretical value: 1068.5383). Theoretical elemental content (%) C 81 H 68 N2: C, 90.97; H, 6.41; N, 2.62. Measured elemental content (%): C, 91.02; H, 6.39; N, 2.57.

[0370] [Synthesis Example 39] Synthesis of Compounds 1-258

[0371]

[0372] Compound 1-1 was synthesized using the same method as in Synthesis Example 29, except that b-46 was replaced with an equimolar amount of b-215, resulting in compound 1-258 (16.76 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 786.3629 (theoretical value: 786.3610). Theoretical elemental content (%) C 58 H 46 N₂O: C, 88.52; H, 5.89; N, 3.56. Measured elemental content (%): C, 88.47; H, 5.92; N, 3.54.

[0373] [Synthesis Example 40] Synthesis of Compound 1-273

[0374]

[0375] The same method as in Synthesis Example 29 was used to synthesize compound 1-1, except that b-46 was replaced with an equimolar amount of b-1-273. Compound 1-273 (18.03 g) was synthesized, and the solid purity was determined by HPLC to be ≥99.87%. Mass spectrometry m / z: 938.4222 (theoretical value: 938.4236). Theoretical elemental content (%) C 70 H 54 N₂O: C, 89.52; H, 5.80; N, 2.98. Measured elemental content (%): C, 89.47; H, 5.79; N, 3.02.

[0376] [Synthesis Example 41] Synthesis of Compound 1-302

[0377]

[0378] The same method as in Synthesis Example 29 was used to synthesize compound 1-1, except that b-46 was replaced with an equimolar amount of b-1-302. Compound 1-302 (17.57 g) was synthesized, and the solid purity was determined by HPLC to be ≥99.89%. Mass spectrometry m / z: 886.3910 (theoretical value: 886.3923). Theoretical elemental content (%) C 66 H 50 N₂O: C, 89.36; H, 5.68; N, 3.16. Measured elemental content (%): C, 89.32; H, 5.71; N, 3.10.

[0379] [Synthesis Example 42] Synthesis of Compound 1-317

[0380]

[0381] Compound 1-1 was synthesized using the same method as in Synthesis Example 29, except that b-46 was replaced with an equimolar amount of b-1-317. Compound 1-317 (17.15 g) was synthesized, and the solid purity was ≥99.90% as determined by HPLC. Mass spectrometry m / z: 852.3546 (theoretical value: 852.3538). Theoretical elemental content (%) C 62 H 48 N₂S: C, 87.29; H, 5.67; N, 3.28. Measured elemental content (%): C, 87.33; H, 5.62; N, 3.35.

[0382] [Synthesis Example 43] Synthesis of Compounds 1-338

[0383]

[0384] Compound 1-1 was synthesized using the same method as in Synthesis Example 29, except that b-46 was replaced with an equimolar amount of b-1-338, and intermediate F-1-1 was replaced with an equimolar amount of intermediate F-1-2. Compound 1-338 (18.03 g) was synthesized, and the solid purity was ≥99.87% as determined by HPLC. Mass spectrometry m / z: 938.4617 (theoretical value: 938.4600). Theoretical elemental content (%) C 71 H 58 N2: C, 90.79; H, 6.22; N, 2.98. Measured elemental content (%): C, 90.83; H, 6.19; N, 3.02.

[0385] [Synthesis Example 44] Synthesis of Compound 1-363

[0386]

[0387] Compound 1-1 was synthesized using the same method as in Synthesis Example 29, except that intermediate A-1-1 was replaced with an equimolar amount of intermediate A-611, and intermediate F-1-1 was replaced with an equimolar amount of intermediate F-1-4. Compound 1-363 (17.04 g) was synthesized, and the solid purity was ≥99.92% as determined by HPLC. Mass spectrometry m / z: 822.3958 (theoretical value: 822.3974). Theoretical elemental content (%) C 62 H 50 N2: C, 90.47; H, 6.12; N, 3.40. Measured element content (%): C, 90.51; H, 6.09; N, 3.36.

[0388] [Synthesis Example 45] Synthesis of Compound 1-382

[0389]

[0390] Compound 1-1 was synthesized using the same method as in Synthesis Example 29, except that intermediate A-1-1 was replaced with an equimolar amount of intermediate A-328, and intermediate F-1-1 was replaced with an equimolar amount of intermediate F-1-5. Compound 1-382 (17.35 g) was synthesized, and the solid purity was ≥99.90% as determined by HPLC. Mass spectrometry m / z: 862.4269 (theoretical value: 862.4287). Theoretical elemental content (%) C 65 H 54 N2: C, 90.45; H, 6.31; N, 3.25. Measured elemental content (%): C, 90.51; H, 6.25; N, 3.30.

[0391] [Synthesis Example 46] Synthesis of Compound 1-391

[0392]

[0393] Compound 1-1 was synthesized using the same method as in Synthesis Example 29, except that a-1 was replaced with an equimolar amount of a-1-391, b-46 was replaced with an equimolar amount of b-461, and intermediate F-1-1 was replaced with an equimolar amount of intermediate F-1-6. Compound 1-391 (18.18 g) was synthesized, and the solid purity was ≥99.85% as determined by HPLC. Mass spectrometry m / z: 976.4767 (theoretical value: 976.4756). Theoretical elemental content (%) C 74 H 60 N2: C, 90.95; H, 6.19; N, 2.87. Measured elemental content (%): C, 91.01; H, 6.22; N, 2.83.

[0394] [Synthesis Example 47] Synthesis of Compounds 1-413

[0395]

[0396] Compound 1-1 was synthesized using the same method as in Synthesis Example 29, except that b-46 was replaced with an equimolar amount of b-1-413. Compound 1-413 (18.01 g) was synthesized, and the solid purity was ≥99.87% as determined by HPLC. Mass spectrometry m / z: 937.4382 (theoretical value: 937.4396). Theoretical elemental content (%) C 70 H 55 N3: C, 89.61; H, 5.91; N, 4.48. Measured elemental content (%): C, 89.56; H, 5.89; N, 4.52.

[0397] [Synthesis Example 48] Synthesis of Compounds 1-453

[0398]

[0399] Compound 1-1 was synthesized using the same method as in Synthesis Example 29, except that b-46 was replaced with an equimolar amount of b-1-453. Compound 1-453 (17.98 g) was synthesized, and the solid purity was ≥99.86% as determined by HPLC. Mass spectrometry m / z: 950.4247 (theoretical value: 950.4236). Theoretical elemental content (%) C 71 H 54 N₂O: C, 89.65; H, 5.72; N, 2.95. Measured elemental content (%): C, 89.70; H, 5.69; N, 2.97.

[0400] [Synthesis Example 49] Synthesis of Compounds 1-463

[0401]

[0402] The same method as in Example 29 was used to synthesize compound 1-1, except that b-46 was replaced with an equimolar amount of b-1-463, to synthesize compound 1-463 (17.99 g). HPLC analysis showed a solid purity ≥ 99.85%. Mass spectrometry m / z: 966.4017 (theoretical value: 966.4008). Theoretical elemental content (%) C 71 H 54 N2S: C, 88.16; H, 5.63; N, 2.90. Measured elemental content (%): C, 88.20; H, 5.58; N, 2.88.

[0403] [Synthesis Example 50] Synthesis of Compound 1-477

[0404]

[0405] The same method as in Synthesis Example 29 was used to synthesize compound 1-1, except that b-46 was replaced with an equimolar amount of b-1-477. Compound 1-477 (18.02 g) was synthesized, and the solid purity was determined by HPLC to be ≥99.86%. Mass spectrometry m / z: 952.4404 (theoretical value: 952.4393). Theoretical elemental content (%) C 71 H 56 N₂O: C, 89.46; H, 5.92; N, 2.94. Measured elemental content (%): C, 89.49; H, 5.88; N, 2.96.

[0406] [Synthesis Example 51] Synthesis of Compound 1-480

[0407]

[0408] The same method as in Synthesis Example 29 was used to synthesize compound 1-1, except that b-46 was replaced with an equimolar amount of b-1-480. Compound 1-480 (17.18 g) was synthesized, and the solid purity was determined by HPLC to be ≥99.92%. Mass spectrometry m / z: 829.3507 (theoretical value: 829.3491). Theoretical elemental content (%) C 59 H 47 N3S: C, 85.37; H, 5.71; N, 5.06. Measured elemental content (%): C, 85.42; H, 5.67; N, 5.10.

[0409] [Synthesis Example 52] Synthesis of Compound 1-508

[0410]

[0411] Compound 1-1 was synthesized using the same method as in Synthesis Example 29, except that b-46 was replaced with an equimolar amount of b-1-508, and intermediate F-1-1 was replaced with an equimolar amount of intermediate F-1-3. Compound 1-508 (18.33 g) was synthesized, and the solid purity was ≥99.85% as determined by HPLC. Mass spectrometry m / z: 984.3560 (theoretical value: 984.3572). Theoretical elemental content (%) C 70 H 52 N2S2: C, 85.33; H, 5.32; N, 2.84. Measured elemental content (%): C, 85.29; H, 5.35; N, 2.78.

[0412] [Synthesis Example 53] Synthesis of Compounds 1-540

[0413]

[0414] The same method as in Synthesis Example 29 was used to synthesize compound 1-1, except that b-46 was replaced with an equimolar amount of b-1-540. Compound 1-540 (16.74 g) was synthesized, and the solid purity was ≥99.93% as determined by HPLC. Mass spectrometry m / z: 796.3831 (theoretical value: 796.3817). Theoretical elemental content (%) C 60 H 48 N2: C, 90.42; H, 6.07; N, 3.51. Measured element content (%): C, 90.37; H, 6.11; N, 3.49.

[0415] [Synthetic Example 54] Synthesis of Compound 2-2

[0416]

[0417] Synthetic intermediate B-2-2

[0418] Under nitrogen protection, compounds c-2-2 (12.96 g, 80 mmol), d-2-2 (28.53 g, 80 mmol), K₂CO₃ (20.73 g, 150 mmol), and Pd(PPh₃)₄ (1.85 g, 1.60 mmol) were added sequentially to a three-necked flask. A 3:1:1 toluene / ethanol / water mixture was added, and the mixture was stirred. The reaction system was heated under reflux for 8 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with deionized water and toluene to obtain an organic layer. The organic layer was washed three times with 550 mL of deionized water, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from toluene to obtain intermediate B-2-2 (23.63 g, 75% yield). HPLC analysis showed a solid purity ≥ 99.5%.

[0419] Synthetic intermediate A-2-2

[0420] Under nitrogen protection, toluene (600 mL), a-2-2 (16.39 g, 60 mmol), b-2-2 (10.15 g, 60 mmol), palladium acetate (0.22 g, 1.0 mmol), sodium tert-butoxide (12.49 g, 130 mmol), and tri-tert-butylphosphine (8 mL of toluene solution) were added sequentially to a 1 L reaction flask, and the mixture was reacted under reflux for 2 hours. After the reaction was stopped, the mixture was cooled to room temperature, filtered with diatomaceous earth, the filtrate was concentrated, recrystallized from toluene, filtered under vacuum, and washed with toluene to obtain the recrystallized solid, yielding intermediate A-2-2 (15.83 g, yield 73%). HPLC analysis showed that the solid purity was ≥99.7%.

[0421] Synthetic compound 2-2

[0422] Under nitrogen protection, toluene solvent (650 mL), intermediate A-2-2 (14.46 g, 40 mmol), intermediate B-2-2 (15.76 g, 40 mmol), Pd2(dba)3 (0.37 g, 0.40 mmol), BINAP (0.75 g, 1.20 mmol), and sodium tert-butoxide (7.69 g, 80 mmol) were added sequentially to a 1 L reaction flask. The mixture was stirred until dissolved, and then refluxed under nitrogen protection for 24 hours. After the reaction was complete, the reaction solution was washed with dichloromethane and distilled water, and extracted by separation. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed. The solution was then purified by column chromatography using cyclohexane:ethyl acetate (20:3) as the eluent, yielding compound 2-2 (19.56 g, 68% yield). HPLC analysis showed a solid purity ≥ 99.8%.

[0423] Mass spectrometry m / z: 718.3360 (theoretical value: 718.3348). Theoretical elemental content (%) C 54 H 42 N2: C, 90.21; H, 5.89; N, 3.90. Measured elemental content (%): C, 90.18; H, 5.93; N, 3.86.

[0424] [Synthetic Example 55] Synthesis of Compound 2-116

[0425]

[0426] Using the same method as in Synthesis Example 54, compound 2-116 (22.86 g) was synthesized by replacing a-2-2 with an equimolar amount of a-2-116. The solid purity was determined by HPLC to be ≥99.6%. Mass spectrometry m / z: 852.4431 (theoretical value: 852.4443). Theoretical elemental content (%) C 64 H 56N2: C, 90.10; H, 6.62; N, 3.28. Measured elemental content (%): C, 90.07; H, 6.58; N, 3.32.

[0427] [Synthetic Example 56] Synthesis of Compound 2-167

[0428]

[0429] Using the same method as in Synthesis Example 54, a-2-2, b-2-2, and c-2-2 were synthesized by replacing a-2-2, b-2-2, and c-2-2 with equimolar amounts of a-2-167, b-2-167, and c-2-167, respectively. The solid purity was determined by HPLC to be ≥99.5%. Mass spectrometry m / z: 902.4460 (theoretical value: 902.4445). Theoretical elemental content (%) C 68 H 38 D 10 N2: C, 90.43; H, 6.47; N, 3.10. Measured elemental content (%): C, 90.39; H, 6.52; N, 3.07.

[0430] [Synthetic Example 57] Synthesis of Compound 2-212

[0431]

[0432] Using the same method as in Synthesis Example 54, a-2-2, b-2-2, c-2-2, and d-2-2 were synthesized by replacing a-2-2, b-2-2, c-2-2, and d-2-2 with equimolar amounts of a-2-212, b-2-212, c-2-167, and d-2-212, respectively. The solid purity was determined by HPLC to be ≥99.2%. Mass spectrometry m / z: 844.3740 (theoretical value: 844.3756). Theoretical elemental content (%) C 64 H 40 D4N2: C, 90.96; H, 5.72; N, 3.31. Measured elemental content (%): C, 90.92; H, 5.68; N, 3.27.

[0433] [Synthetic Example 58] Synthesis of Compound 2-269

[0434]

[0435] Using the same method as in Synthesis Example 54, a-2-2, b-2-2, and d-2-2 were synthesized by replacing a-2-2, b-2-2, and d-2-2 with equimolar amounts of a-2-269, b-2-269, and d-2-269, respectively. The solid purity was determined by HPLC to be ≥99.6%. Mass spectrometry m / z: 793.3728 (theoretical value: 793.3709). Theoretical elemental content (%) C 61 H 47 N: C, 92.27; H, 5.97; N, 1.76. Measured element content (%): C, 92.31; H, 5.94; N, 1.80.

[0436] [Synthetic Example 59] Synthesis of Compound 2-374

[0437]

[0438] Using the same method as in Synthesis Example 54, a-2-2, b-2-2, and B-2-2 were synthesized by replacing a-2-2, b-2-2, and B-2-2 with equimolar amounts of a-2-374, b-2-374, and B-2-269, respectively. The solid purity was determined by HPLC to be ≥99.8%. Mass spectrometry m / z: 893.4039 (theoretical value: 893.4055). Theoretical elemental content (%) C 66 H 55 NS: C, 88.65; H, 6.20; N, 1.57. Measured elemental content (%): C, 88.70; H, 6.17; N, 1.62.

[0439] [Synthetic Example 60] Synthesis of Compound 2-393

[0440]

[0441] Using the same method as in Synthesis Example 54, a-2-2, b-2-2, and d-2-2 were synthesized by replacing a-2-2, b-2-2, and d-2-2 with equimolar amounts of a-2-393, b-2-393, and d-2-393, respectively. The solid purity was determined by HPLC to be ≥99.6%. Mass spectrometry m / z: 958.4272 (theoretical value: 958.4287). Theoretical elemental content (%) C 73 H 54 N2: C, 91.41; H, 5.67; N, 2.92. Measured element content (%): C, 91.37; H, 5.71; N, 2.88.

[0442] [Synthetic Example 61] Synthesis of Compound 2-413

[0443]

[0444] Using the same method as in Synthesis Example 54, b-2-2, c-2-2, and d-2-2 were synthesized by replacing b-2-2, c-2-2, and d-2-2 with equimolar amounts of b-2-413, c-2-413, and d-2-413, respectively. The solid purity was determined by HPLC to be ≥99.4%. Mass spectrometry m / z: 755.4478 (theoretical value: 755.4491). Theoretical elemental content (%) C 57 H 57 N: C, 90.55; H, 7.60; N, 1.85. Measured element content (%): C, 90.60; H, 7.57; N, 1.90.

[0445] [Synthetic Example 62] Synthesis of Compound 2-429

[0446]

[0447] Using the same method as in Synthesis Example 54, a-2-2, b-2-2, c-2-2, and d-2-2 were synthesized by replacing a-2-2, b-2-2, c-2-2, and d-2-2 with equimolar amounts of a-2-393, b-2-429, c-2-429, and d-2-269, respectively. Compound 2-429 (18.85 g) was synthesized, and the solid purity was determined by HPLC to be ≥99.5%. Mass spectrometry m / z: 747.3852 (theoretical value: 747.3865). Theoretical elemental content (%) C 57 H 49 N: C, 91.52; H, 6.60; N, 1.87. Measured element content (%): C, 91.48; H, 6.56; N, 1.91.

[0448] [Synthetic Example 63] Synthesis of Compound 2-448

[0449]

[0450] Using the same method as in Synthesis Example 54, a-2-2 and B-2-2 were synthesized by replacing a-2-2 and B-2-2 with equimolar amounts of a-2-448 and B-2-269, respectively. Compound 2-448 (17.05 g) was obtained, and the solid purity was ≥99.3% as determined by HPLC. Mass spectrometry m / z: 645.3378 (theoretical value: 645.3396). Theoretical elemental content (%) C 49 H 43 N: C, 91.12; H, 6.71; N, 2.17. Measured element content (%): C, 91.08; H, 6.67; N, 2.21.

[0451] [Synthetic Example 64] Synthesis of Compound 2-503

[0452]

[0453] Using the same method as in Synthesis Example 54, a-2-2 and d-2-2 were synthesized by replacing a-2-2 and d-2-2 with equimolar amounts of a-2-503 and d-2-503, respectively. The solid purity was determined by HPLC to be ≥99.2%. Mass spectrometry m / z: 843.3518 (theoretical value: 843.3501). Theoretical elemental content (%) C 64 H 45 NO: C, 91.07; H, 5.37; N, 1.66. Measured elemental content (%): C, 91.12; H, 5.40; N, 1.71.

[0454] [Synthetic Example 65] Synthesis of Compound 2-558

[0455]

[0456] Using the same method as in Synthesis Example 54, a-2-2 and d-2-2 were synthesized by replacing a-2-2 and d-2-2 with equimolar amounts of a-2-558 and d-2-558, respectively. The solid purity was determined by HPLC to be ≥99.7%. Mass spectrometry m / z: 735.2978 (theoretical value: 735.2960). Theoretical elemental content (%) C 54 H 41 NS: C, 88.13; H, 5.62; N, 1.90. Measured elemental content (%): C, 88.09; H, 5.58; N, 1.87.

[0457] [Synthetic Example 66] Synthesis of Compound 2-606

[0458]

[0459] Using the same method as in Synthesis Example 54, a-2-2, b-2-2, c-2-2, and d-2-2 were synthesized by replacing a-2-2, b-2-2, c-2-2, and d-2-2 with equimolar amounts of a-2-606, b-2-606, c-2-167, and d-2-606, respectively. Compound 2-606 (20.38 g) was obtained, and the solid purity was ≥99.2% as determined by HPLC. Mass spectrometry m / z: 848.4192 (theoretical value: 848.4179). Theoretical elemental content (%) C 65 H 44 D5N: C, 91.94; H, 6.41; N, 1.65. Measured elemental content (%): C, 91.89; H, 6.37; N, 1.70.

[0460] [Synthetic Example 67] Synthesis of Compound 2-718

[0461]

[0462] Using the same method as in Synthesis Example 54, a-2-2 and c-2-2 were synthesized by replacing a-2-2 and c-2-2 with equimolar amounts of a-2-718 and c-2-718, respectively. Compound 2-718 (18.23 g) was obtained, and the solid purity was ≥99.6% as determined by HPLC. Mass spectrometry m / z: 734.3580 (theoretical value: 734.3599). Theoretical elemental content (%) C 55 H 38 D4N2: C, 89.88; H, 6.31; N, 3.81. Measured elemental content (%): C, 89.92; H, 6.27; N, 3.78.

[0463] [Comparative Examples 1-3] Component Fabrication Examples:

[0464] Comparative Example 1: The ITO substrate was washed three times in distilled water and ultrasonically cleaned for 15 minutes. After the distilled water cleaning was completed, it was ultrasonically cleaned in sequence with solvents such as isopropanol, acetone, and methanol. Then it was dried at 120°C and sent to the vapor deposition machine.

[0465] On a prepared ITO transparent electrode, a hole injection layer (HAT-CN / 16nm), a hole transport layer (HT1-1 / 78nm), a light-emitting layer (a mixture of CBP and Ir(ppy)3 (93%:7% by mass) / 27nm) was deposited layer by layer using vacuum evaporation. Then, an electron transport layer (TMPYPB and Liq, doped at a mass ratio of 1:1) / 35nm, an electron injection layer (LiF / 1nm), and a cathode (Al / 100nm) were deposited. The device was then sealed in a glove box, thus fabricating an organic electroluminescent device. After completing the fabrication of the organic electroluminescent device according to the above steps, the photoelectric properties of the device were measured. The molecular structures of the relevant materials are shown below:

[0466]

[0467] Comparative Example 2: Compound HT1-1 in Comparative Example 1 was replaced with compound HT1-2, and the other steps were the same to obtain the comparative organic electroluminescent element 2. Comparative Example 3: Compound HT1-1 in Comparative Example 1 was replaced with compound HT1-3, and the other steps were the same to obtain the comparative organic electroluminescent element 3.

[0468] [Application Examples 1-53]

[0469] Using compounds 1, 18, 46, 58, 81, 84, 97, 138, 141, 147, 163, 164, 167, 175, 200, 210, 215, 220, 241, 254, 260, 328, 379, 416, 452, 461, 489, 518, 1-1, 1-26, 1-34, 1-66, 1-71, etc. of the present invention Compounds 1-104, 1-126, 1-146, 1-164, 1-181, 1-258, 1-273, 1-302, 1-317, 1-338, 1-363, 1-382, 1-391, 1-413, 1-453, 1-463, 1-477, 1-480, 1-508, and 1-540 were used to replace compound HT1-1 in Comparative Example 1. Otherwise, organic electroluminescent elements were prepared using the same preparation method as in Comparative Example 1.

[0470] A combined IVL testing system was used to test the luminous efficiency of organic light-emitting elements (OLEDs), comprising testing software, a computer, a Keithley K2400 digital source meter, and a PhotoResearch PR788 spectral scanning luminance meter. Lifetime testing was performed using a McScience M6000 OLED lifetime testing system. The testing environment was atmospheric, and the temperature was room temperature. The luminous characteristic test results of the obtained organic electroluminescent elements are shown in Table 1. Table 1 presents the luminous characteristic test results of the OLEDs prepared by the compounds in the embodiments of this invention and the comparative materials.

[0471] [Table 1] Test of light-emitting characteristics of light-emitting elements

[0472]

[0473]

[0474]

[0475] Note: T95 refers to a current density of 10 mA / cm². 2 Under certain conditions, the time it takes for the brightness of a component to decay to 95%;

[0476] As can be seen from the results in Table 1, the triarylamine derivative of the present invention, when applied to organic electroluminescent elements as a hole transport layer material, exhibits advantages such as high luminous efficiency and long service life compared with comparative examples 1-3, and is a high-performance hole transport material.

[0477] [Comparative Examples 4-5] Component Fabrication Examples:

[0478] Comparative Example 4: The ITO transparent substrate was washed three times in distilled water and ultrasonically washed for 15 minutes. After the distilled water washing was completed, it was ultrasonically washed in sequence with solvents such as isopropanol, acetone, and methanol, and then dried at 120°C and sent to the vapor deposition machine.

[0479] On a prepared ITO transparent substrate electrode, a hole injection layer HAT-CN / 15nm, a first hole transport layer HT1-1 / 80nm, a second hole transport layer 2-2 / 50nm, a light-emitting layer (body CBP:Ir(piq)3 (98%:2% mass ratio)) / 25nm, an electron transport layer TAZ / 25nm, an electron injection layer LiF / 0.5nm, and a cathode Al / 110nm were deposited by vacuum evaporation. The device was then sealed in a glove box to fabricate an organic electroluminescent device. After completing the fabrication of the organic electroluminescent device according to the above steps, the photoelectric performance of the device was measured. The molecular structure formulas of the relevant materials are shown below:

[0480]

[0481] Comparative Example 5: The first hole transport layer compound HT1-1 in Comparative Example 4 was replaced with compound HT1-3, and the other steps were the same, to obtain the comparative organic electroluminescent element 5.

[0482] Comparative Example 6: The ITO transparent substrate was washed three times in distilled water and ultrasonically cleaned for 15 minutes. After the distilled water cleaning, it was ultrasonically cleaned in sequence with solvents such as isopropanol, acetone, and methanol, and then dried at 120°C before being sent to a vapor deposition machine. A hole injection layer (HAT-CN / 15nm), a hole transport layer (compound 2-2 / 130nm), a light-emitting layer (body CBP:Ir(piq)3 (98%:2% by mass) / 25nm), an electron transport layer (TAZ / 25nm), an electron injection layer (LiF / 0.5nm), and a cathode (Al / 110nm) were then deposited on the prepared ITO transparent substrate electrode using a layer-by-layer vacuum vapor deposition method. The device was then sealed in a glove box, thus fabricating an organic electroluminescent device.

[0483] Comparative Example 7: The hole transport layer compound 2-2 in Comparative Example 4 was replaced with compound 2-374, and the other steps were the same.

[0484] Application Example 54: An ITO transparent substrate was washed three times in distilled water and ultrasonically cleaned for 15 minutes. After distilled water cleaning, it was ultrasonically cleaned in sequence with solvents such as isopropanol, acetone, and methanol, and then dried at 120°C before being sent to a vapor deposition machine. A hole injection layer (HAT-CN / 15nm), a hole transport layer (1 / 130nm), a light-emitting layer (body CBP:Ir(piq)3 (98%:2% by mass) / 25nm), an electron transport layer (TAZ / 25nm), an electron injection layer (LiF / 0.5nm), and a cathode (Al / 110nm) were deposited on the prepared ITO transparent substrate electrode using a layer-by-layer vacuum vapor deposition method. The device was then sealed in a glove box, thus fabricating an organic electroluminescent device.

[0485] Application Examples 55-66: The hole transport layer compound 1 in Application Example 54 is replaced sequentially with compounds 46, 147, 163, 164, 215, 328, 1-1, 1-26, 1-34, 1-146, 1-181, and 1-413 of the present invention, while the other steps are the same, to obtain the organic electroluminescent element Application Examples 55-66.

[0486] [Application Examples 67-93]

[0487] In Comparative Example 4, the first hole transport layer material compound HT1-1 was sequentially replaced with compounds 1, 18, 46, 58, 84, 147, 163, 164, 167, 175, 200, 210, 215, 328, 461, 1-1, 1-26, 1-34, 1-66, 1-104, 1-146, 1-164, 1-181, 1-258, 1-273, 1-363, and 1-382 of the present invention. Simultaneously, the second hole transport layer material compound 2 of the organic electroluminescent element was sequentially replaced. -2 is replaced sequentially with compounds 2-2, 2-116, 2-167, 2-212, 2-269, 2-374, 2-393, 2-413, 2-429, 2-448, 2-503, 2-558, 2-606, 2-718, 2-751, 2-2, 2-116, 2-167, 2-212, 2-269, 2-374, 2-393, 2-413, 2-448, 2-503, 2-558, and 2-606 of the present invention, and all other steps are the same as in Comparative Example 4.

[0488] Table 2 shows the test results of the luminescence characteristics of the light-emitting elements prepared by the compounds prepared in the embodiments of the present invention and the comparative substances.

[0489] [Table 2] Test of light-emitting characteristics of light-emitting elements

[0490]

[0491]

[0492]

[0493] Note: T95 refers to a current density of 10 mA / cm². 2 Under certain conditions, the time it takes for the brightness of a component to decay to 95%;

[0494] As can be seen from the results in Table 2, the organic electroluminescent element of the present invention exhibits advantages of high luminous efficiency and long lifespan compared to comparative embodiments 3-4. Furthermore, these luminous efficiency and lifespan are exceptionally good in the art, thus making it a high-performance organic electroluminescent element. This is due to the specific combination of the first and second hole transport layer materials of the present invention. Their combined effect enables the efficiency of the organic electroluminescent element of the present invention to break through the limitations of conventional organic electroluminescent elements, resulting in superior performance.

[0495] It should be noted that the present invention has been specifically described with reference to individual embodiments, but those skilled in the art can make various forms or details of improvements to the present invention without departing from the principles of the present invention, and these improvements also fall within the protection scope of the present invention.

Claims

1. An organic electroluminescent element, comprising a substrate, an anode, an organic layer, and a cathode, characterized in that, The organic layer contains a triarylamine derivative represented by formula (Ⅰ). The r is selected from 1 or 2; When r equals 1, R is selected from one of the following cycloalkyl groups: The R p Selected from hydrogen, deuterium, and C1-C6 alkyl groups; p2 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14 or 15; When r equals 2, the connection between the two Rs forms a fatty ring as shown below: The R q Selected from hydrogen, deuterium, and C1-C6 alkyl groups; The q3 is selected from 0, 1, 2, 3, 4, 5 or 6; the q4 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the q5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; The Ar0 is selected from deuterium, or any of the following groups: R0 and R1 are independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted phenyl; "substituted..." means monosubstituted or polysubstituted by a group independently selected from deuterium, methyl, ethyl, isopropyl, tert-butyl. The m is selected from 0, 1, 2, 3 or 4; when m is greater than 1, two or more R0s are the same or different from each other, or two adjacent R0s are connected to form a benzene ring; The n is selected from 0, 1, 2 or 3; when n is greater than 1, two or more R1s are the same or different from each other, or two adjacent R1s are connected to form a benzene ring; The Ar1 and Ar2 may be the same as or different from each other, and are independently selected from one of the following substituents: The R b It is selected from one of phenyl, biphenyl, deuterated phenyl, deuterated naphthyl, deuterated biphenyl, tolyl, terphenyl, and naphthyl; The R a It is selected from one of hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, and phenyl; Wherein R a It can also be R aa Replaced by, R aa It is selected from one or more of hydrogen, deuterium, methyl, ethyl, n-propyl, n-butyl, isopropyl, and tert-butyl, and when substituted by multiple substituents, the multiple substituents may be the same or different from each other; The a ， The a0 is 0, 1, or 2; the a1 is 0, 1, 2, or 3; the a2 is 0, 1, 2, 3, or 4; the a3 is 0, 1, 2, 3, 4, 5, 6, or 7; the a5 is 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9. The L0 is selected from single-bonded, substituted or unsubstituted phenylene, wherein the substituent is one or more of deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, and when substituted by multiple substituents, the multiple substituents may be the same or different from each other; L1 is selected from single bonds; The L2 to L3 are independently selected from one of the following: single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted 9,9-dimethylfluorene, substituted or unsubstituted 9,9-diphenylfluorene, substituted or unsubstituted dibenzofuranyl, and substituted or unsubstituted dibenzothiopheneyl. The substituent is one or more of deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, and tert-butyl. When substituted by multiple substituents, the multiple substituents may be the same as or different from each other.

2. The organic electroluminescent element according to claim 1, characterized in that, The R p It is selected from hydrogen and deuterium.

3. The organic electroluminescent element according to claim 1, characterized in that, The R q It is selected from hydrogen and deuterium.

4. The organic electroluminescent element according to claim 1, characterized in that, The Ar0 is selected from any one of the following groups: 。 5. The organic electroluminescent element according to claim 1, characterized in that, The L2 and L3 are independently selected from one of a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, or a substituted or unsubstituted biphenylene, wherein the substituent is one or more of deuterium and methyl, and in the case of being substituted by multiple substituents, the multiple substituents are the same as or different from each other.

6. The organic electroluminescent element according to claim 1, characterized in that, The triarylamine derivative is selected from any one of the following chemical structures: 。 7. The organic electroluminescent element according to claim 1, characterized in that, The organic layer includes a hole transport layer containing any one or a combination of at least two of the triarylamine derivatives represented by formula (I).

8. The organic electroluminescent element according to claim 7, characterized in that, The hole transport layer includes a first hole transport layer and a second hole transport layer. The first hole transport layer is located between the anode and the second hole transport layer, and the second hole transport layer is located between the first hole transport layer and the cathode. The first hole transport layer contains any one or a combination of at least two of the triarylamine derivatives represented by formula (I), and the second hole transport layer contains any one or a combination of at least two of the fluorene-containing triarylamine compounds represented by formula (II). The A is selected from one of formulas A-1, A-2, and A-3; wherein R... 11 R 12 Independently selected from any one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C3-C30 cycloalkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or adjacent R 11 They can bond together to form benzene rings or naphthalene rings, adjacent R 12 They can bond together to form benzene rings or naphthalene rings; The value of 'a' is selected from 0, 1, 2, 3, or 4; the value of 'b' is selected from 0, 1, 2, or 3. The R 22 Selected from any one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or R 22 With R 22 They connect to form fatty rings; The Ar is selected from one of the following groups: Wherein, the R c It is selected from one of hydrogen, deuterium, halogen atom, cyano, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, and substituted or unsubstituted C2-C20 heteroaryl. k is selected from 0, 1, or 2; i is selected from 0, 1, 2, or 3; j is selected from 0, 1, 2, 3, 4, 5, 6, or 7; d is selected from 0, 1, 2, 3, or 4; h is selected from 0, 1, 2, 3, 4, or 5; e is selected from 0, 1, 2, 3, 4, 5, or 6; f is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; g is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. The Ar a It is selected from any one of deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl; The L a ~L c It is independently selected from any one of the following: single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted C6-C30 arylene-substituted or unsubstituted C2-C30 heteroarylene, or adjacent substituents can be bonded together to form a cyclic structure.

9. The organic electroluminescent element according to claim 8, characterized in that, The R c It is selected from one of the following: hydrogen, deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, canyl, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, naphthyl, deuterated naphthyl, anthracene, phenanthrene, triphenylene, perylene, pyrene, tolyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-phenylcarbazolyl, acridine, dibenzofuranyl, dibenzothiophene, deuterated 9,9-dimethylfluorenyl, deuterated 9,9-diphenylfluorenyl, deuterated 9-phenylcarbazolyl, deuterated dibenzofuranyl, deuterated dibenzothiophene, phenothiazinyl, phenotoxazinyl, and indole.

10. The organic electroluminescent element according to claim 8, characterized in that, The Ar a Selected from one of the following groups: The R t It is selected from one of the following: substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, and substituted or unsubstituted C2-C20 heteroaryl; The R s Selected from one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C20 heteroaryl, or adjacent R s They can be connected to form a ring structure; Wherein, the R s It can also be R ss Replaced by, R ss It is selected from one or more of hydrogen, deuterium, methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornel, canyl, phenyl, pentadeuterated phenyl, deuterated naphthyl, tolyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, stilbene, spirofluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-phenylcarbazolyl, dibenzothiophene, and dibenzofuranyl, wherein when substituted with multiple substituents, the multiple substituents are the same or different from each other; The s ， The s0 is 0, 1, or 2; the s1 is 0, 1, 2, or 3; the s2 is 0, 1, 2, 3, or 4; the s3 is 0, 1, 2, 3, 4, 5, 6, or 7; and the s4 is 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9.

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