An organic light emitting device

Abstract

The application provides an organic light-emitting device, and relates to the technical field of organic electroluminescence.The hole transport region comprises a first hole transport layer and a second hole transport layer, a triarylamine derivative represented by formula I is applied to the first hole transport layer, and a triamine compound represented by formula II is applied to the second hole transport layer, the two materials are combined and simultaneously applied to the organic light-emitting device, the transmission efficiency of holes and electrons in the device is improved, the holes and the electrons are effectively blocked in the light-emitting layer, the maximum recombination of the carriers is realized, the light-emitting efficiency of the device is greatly improved, the service life of the device is prolonged, and the application effect and industrialization prospect are good.The application can be widely applied to the fields of panel display, illumination light source, organic solar cell, organic photoreceptor or organic thin film transistor and the like.

Description

Technical Field

[0001] This invention relates to the field of organic electroluminescence technology, and more particularly to an organic light-emitting device. Background Technology

[0002] Organic light-emitting diodes (OLEDs) are devices that emit light when organic photoelectric materials are exposed to an electric current or field, directly converting electrical energy into light energy. Due to their advantages such as full-spectrum color rendering, high brightness, high efficiency, flexible display capabilities, and fast response speed, OLEDs can be used to manufacture new display products and new lighting products, and are expected to replace existing liquid crystal displays and fluorescent lighting, with a very wide range of applications.

[0003] Organic light-emitting devices (OLEDs) typically consist of an anode, an organic layer, and a metal cathode. The organic layer is usually one or more organic films obtained through vacuum deposition or spin coating, and generally includes a hole injection layer (HIL), a hole transport layer (HTL), an emissive layer (EML), an electron transport layer (ETL), and an electron injection layer (EIL). The purpose of adding an organic layer in an OLED is to regulate the balance of charge carriers and effectively confine the recombination region within the emissive layer, preventing exciton quenching by the electrodes and improving recombination efficiency, thereby increasing luminous efficiency. The mechanism of OLED light emission is as follows: Under an applied bias voltage, holes and electrons overcome the interface barrier and are injected through the anode and cathode into the HOMO level of the hole transport material and the LUMO level of the electron transport material. Then, driven by an external electric field, the charge is transported to the emissive layer. Finally, electrons and holes recombine within the emissive layer to form excitons. These excitons are not in a stable state and subsequently release energy in the form of light, returning to a stable ground state, thus achieving light emission.

[0004] In OLED devices, carrier transport materials are classified into electron transport materials and hole transport materials based on their charge transport properties. Due to the mismatch in the mobilities of holes and electrons, the injection of holes and electrons becomes unbalanced, preventing effective recombination of holes and electrons within the light-emitting layer to generate excitons, thus reducing the luminous efficiency of the organic light-emitting device. Therefore, a first hole transport layer material and a second hole transport layer material are added to the hole transport layer. By adjusting the structure of these materials, suitable HOMO and LUMO orbital energy levels are achieved, thereby increasing the recombination probability of holes and electrons and ensuring effective injection and transport of holes and electrons between the anode and cathode. Therefore, providing an organic light-emitting device with a matched first and second hole transport layer to obtain an organic light-emitting device with high luminous efficiency and low driving voltage is an urgent problem to be solved. Summary of the Invention

[0005] The purpose of this invention is to provide an organic light-emitting device that improves the device characteristics, especially to significantly improve the luminous efficiency and extend the lifespan of the device.

[0006] To achieve the above objectives, this invention provides an organic light-emitting device and provides an in-depth evaluation of its characteristics, thus solving the aforementioned problems. The device includes a substrate, an anode, an organic layer, and a cathode. The organic layer includes a hole transport region, which comprises a first hole transport layer and a second hole transport layer. The first hole transport layer contains a triarylamine derivative represented by Formula I, and the second hole transport layer contains a triamine compound represented by Formula II.

[0007]

[0008] In Formula I, Ar is selected from substituted phenyl, substituted naphthyl, and the substituent is one or more of deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, or adjacent substituents can be connected to form a saturated or unsaturated aliphatic ring.

[0009] The R is selected from substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C3-C12 cycloalkyl groups, substituted or unsubstituted aryl groups, or two adjacent R groups can be bonded together to form a cyclic structure;

[0010] The R m R n R c R d It is independently selected from any one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, and substituted or unsubstituted C6-C30 aryl;

[0011] The value of m is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; when m is greater than 1, two or more R m They are the same or different from each other, or two adjacent R m The links between them form benzene rings or naphthalene rings;

[0012] The value of n is selected from 0, 1, 2, 3, 4, 5, 6, or 7; when n is greater than 1, two or more R n They are the same or different from each other, or two adjacent R n The links between them form benzene rings or naphthalene rings;

[0013] The value of c is selected from 0, 1, 2, or 3; when c is greater than 1, two or more R... c They are the same or different from each other, or two adjacent R cThe links between them form benzene rings or naphthalene rings;

[0014] The d is selected from 0, 1, 2, 3, or 4; when d is greater than 1, two or more R d They are the same or different from each other, or two adjacent R d The links between them form benzene rings or naphthalene rings;

[0015] The L a L b L c It is independently selected from one of the following: single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C3-C30 aliphatic ring, and fused and cycloalgyl groups of C6-C30 aromatic ring;

[0016] In Formula II, at least one of Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 is selected from the groups shown in Formula 1-1 or Formula 1-2, and the others are independently selected from the groups shown in Formula 1-3:

[0017]

[0018] R4~R 11 The alkyl group is independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, or substituted or unsubstituted C6-C25 aryl, or two adjacent substituents are bonded together to form a cyclic structure, wherein R8, R9, and R1 are ...3-C12 cycloalkyl, or substituted or unsubstituted C6-C25 aryl, or two adjacent substituents are bonded together to form a cyclic structure, wherein R8, R9, and R1 are selected from hydrogen, deuterium, substituted or unsubstituted C 10 R 11 There is one and only one carbon atom that serves as the connection site with L0;

[0019] The R0 groups are selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, canyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, or two adjacent R0 groups can be bonded together to form a cyclic structure.

[0020] The R z The same or different Rs are selected from one of hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, canyl, phenyl, naphthyl, biphenyl, deuterated phenyl, deuterated naphthyl, deuterated biphenyl, or any two adjacent Rs. z The groups can bond together to form saturated or unsaturated three-membered, four-membered, five-membered, six-membered, or seven-membered aliphatic ring groups; there is one and only one R. z The corresponding carbon atom is the site connected to bridging L1 to L6; wherein R z It can also be R zz Replaced by, Rzz 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, stilbene, spirofluorenyl, 9,9-dimethylfluorenyl, and 9,9-diphenylfluorenyl, wherein when substituted with multiple substituents, the multiple substituents may be the same as or different from each other;

[0021] R1, R2, and R3 are independently selected from one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, and substituted or unsubstituted C6-C25 aryl.

[0022] L1, L2, L3, L4, L5, and L6 are independently selected from one of the following: single bond, substituted or unsubstituted C6-C30 arylene group, substituted or unsubstituted C3-C30 aliphatic ring, and fused and cycloalgyl groups of C6-C30 aromatic ring.

[0023] The beneficial effects of this invention are:

[0024] This invention provides an organic light-emitting device, wherein the hole transport region includes a first hole transport layer and a second hole transport layer. A triarylamine derivative represented by Formula I is applied to the first hole transport layer, and a triamine compound represented by Formula II is applied to the second hole transport layer. The combination of these two materials and their simultaneous application in the organic light-emitting device improves the transport efficiency of holes and electrons in the device and effectively blocks holes and electrons within the light-emitting layer, achieving maximum recombination of charge carriers. This significantly improves the luminous efficiency and lifespan of the device, demonstrating good application effects and industrialization prospects. Detailed Implementation

[0025] 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.

[0026] In this specification, when the position of the substituent on the aromatic ring is not fixed, it means that it can be attached to any of the corresponding optional sites on the aromatic ring. For example, Can represent And so on.

[0027] 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.

[0028] 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.

[0029] 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.

[0030] 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.

[0031] The aliphatic ring described in this invention refers to a cyclic hydrocarbon with aliphatic properties, containing a closed carbon ring in the molecule, preferably with 3 to 60 carbon atoms, more preferably 3 to 30 carbon atoms, even more preferably 3 to 18 carbon atoms, more preferably 3 to 12 carbon atoms, and most preferably 3 to 7 carbon atoms. It can form monocyclic or polycyclic hydrocarbons, and can be fully saturated or partially saturated. Specific examples include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclobutene, cyclopentene, cyclohexene, cycloheptene, etc., but are not limited thereto. Multiple monocyclic hydrocarbons can also be connected in various ways: two rings in the molecule can share a carbon atom to form a spiro ring; two carbon atoms on the 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.

[0032] 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.

[0033] The fused aliphatic and aromatic rings and cycloalkanes mentioned in this invention refer to the general term for divalent groups remaining after removing two hydrogen atoms from the fused aliphatic and aromatic rings. Preferably, they have 7 to 30 carbon atoms, more preferably 7 to 18 carbon atoms, and most preferably 7 to 12 carbon atoms. Examples may include, but are not limited to, benzo[a]cyclopropyl, benzo[a]cyclobutyl, benzo[a]cyclopentyl, benzo[a]cyclohexyl, benzo[a]cycloheptyl, benzo[a]cyclopentenyl, benzo[a]cyclohexenyl, benzo[a]cycloheptenyl, naphtho[a]cyclopropyl, naphtho[a]cyclobutyl, naphtho[a]cyclopentyl, and naphtho[a]cyclohexyl, etc.

[0034] The term "substituted..." as used in this invention, such as substituted alkyl, substituted cycloalkyl, substituted aryl, substituted arylene, etc., refers to a group that is independently selected from, but not limited to, deuterium, 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., and is preferably selected from deuterium. The following groups are monosubstituted or polysubstituted: methyl, ethyl, isopropyl, tert-butyl, 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, carbazole, 9-phenylcarbazole, acridine, furanyl, thiophene, benzofuranyl, benzothiophene, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, dibenzothiophene, phenothiazinyl, phenothiazinyl, and indole. Furthermore, the above substituents may be replaced by one or more substituents selected from deuteryl, halogen, cyano, alkyl, cycloalkyl, and aryl.

[0035] 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:

[0036]

[0037] 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 benzene, naphthalene, fluorene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, cyclohexane-benzene, quinoline, isoquinoline, dibenzothiophene, phenanthrene, or pyrene, but is not limited thereto.

[0038] This invention provides an organic light-emitting device, comprising a substrate, an anode, an organic layer, and a cathode. The organic layer can be divided into multiple regions. For example, the organic layer may include a hole transport region, a light-emitting layer, and an electron transport region, with the hole transport region located between the anode and the light-emitting layer. The hole transport region can be a single-layer hole transport layer (HTL), including a single-layer hole transport layer containing only one compound and a single-layer hole transport layer containing multiple compounds. The hole transport region can also be a multilayer structure including at least one of a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL). The electron transport region is located between the light-emitting layer and the cathode, and can be a single-layer electron transport layer (ETL), including a single-layer electron transport layer containing only one compound and a single-layer electron transport layer containing multiple compounds. The electron transport region can also be a multilayer structure including at least one of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL). The organic layers of the organic light-emitting device of the present invention can be formed as a single layer or as a multilayer structure with multiple organic layers stacked together. Furthermore, each organic layer may contain one or more layers; for example, the hole transport layer may contain a first hole transport layer and a second hole transport layer, and the electron transport layer may contain a first electron transport layer and a second electron transport layer. Corresponding functional layers can be added or removed as needed; for example, a capping layer may be included on the outer side of the cathode of the organic light-emitting device. For example, an electron buffer layer may be added between the electron transport layer and the electron injection layer, and organic layers with the same function can be made into a stacked structure of two or more layers.

[0039] The organic light-emitting device of the present invention is typically formed on a substrate. The substrate can be used below the anode or above the cathode. The substrate is typically made of glass or polymer material with excellent mechanical strength, thermal stability, water resistance, and transparency. The substrate need not change during the formation of the electrodes or the organic layer; for example, substrates made of glass, plastic, polymer films, silicon, etc. When the substrate is opaque, the electrode opposite it is preferably transparent or translucent.

[0040] In the organic light-emitting device of the present invention, the anode material can be selected from metals, such as aluminum, 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), tin dioxide (SnO2), and zinc aluminum oxide; and conductive polymers, such as polyaniline, polypyrrole, and poly(3-methylthiophene). In addition to 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.

[0041] In the organic light-emitting device described in this 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., an aromatic amine compound, a phthalocyanine compound, a conjugated organic material containing a polycyano group, etc., but is not limited to these.

[0042] In the organic light-emitting device of the present invention, the hole transport layer material can 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 includes a first hole transport layer and a second hole transport layer. The first hole transport layer is located between the hole injection layer and the second hole transport layer, and the second hole transport layer is located between the first hole transport layer and the light-emitting layer. Preferably, the material of the first hole transport layer of the present invention is selected from triarylamine derivatives represented by Formula I.

[0043]

[0044] In Formula I, Ar is selected from substituted phenyl, substituted naphthyl, and the substituent is one or more of deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, or adjacent substituents can be connected to form a saturated or unsaturated aliphatic ring.

[0045] The R is selected from substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C3-C12 cycloalkyl groups, substituted or unsubstituted aryl groups, or two adjacent R groups can be bonded together to form a cyclic structure;

[0046] The R m R n R c R d It is independently selected from any one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, and substituted or unsubstituted C6-C30 aryl;

[0047] The value of m is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; when m is greater than 1, two or more R m They are the same or different from each other, or two adjacent R m The links between them form benzene rings or naphthalene rings;

[0048] The value of n is selected from 0, 1, 2, 3, 4, 5, 6, or 7; when n is greater than 1, two or more Rn They are the same or different from each other, or two adjacent R n The links between them form benzene rings or naphthalene rings;

[0049] The value of c is selected from 0, 1, 2, or 3; when c is greater than 1, two or more R... c They are the same or different from each other, or two adjacent R c The links between them form benzene rings or naphthalene rings;

[0050] The d is selected from 0, 1, 2, 3, or 4; when d is greater than 1, two or more R d They are the same or different from each other, or two adjacent R d The links between them form benzene rings or naphthalene rings;

[0051] The L a L b L c It is independently selected from one of the following: single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C3-C30 aliphatic ring, and fused and cycloalkanes of C6-C30 aromatic ring.

[0052] Preferably, in formula I, Selected from one of the following groups:

[0053]

[0054] Preferably, the R c R d Independently selected from hydrogen, deuterium, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, adamantyl, norbornel, phenyl, tolyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, phenylenetriene, pyrene, phenyl-naphthyl, spirodifluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl. One of the following: deuterated adamantyl, deuterated norbornel, deuterated phenyl, deuterated naphthyl, deuterated biphenyl, deuterated terphenyl, deuterated anthracene, deuterated phenanthryl, deuterated triphenylene, deuterated phenyl-naphthyl, deuterated phenyl-deuterated naphthyl, phenyl-deuterated naphthyl, deuterated 9,9-dimethylfluorenyl, deuterated 9,9-diphenylfluorenyl, deuterated spirodifluorenyl, or adjacent R. c Adjacent R d They can be linked together to form benzene rings or naphthalene rings.

[0055] More preferably, the R c R d Independently selected from hydrogen, deuterium, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, adamantyl, norbornel, or one of the following substituents, or adjacent Rc Adjacent R d They can be linked together to form benzene rings or naphthalene rings.

[0056]

[0057] More preferably, the R c R d Independently selected from hydrogen, deuterium, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, adamantyl, norbornel, or one of the following substituents, or adjacent R c Adjacent R d They can be linked together to form benzene rings or naphthalene rings.

[0058]

[0059] Preferably, the Ar contains at least one deuterium.

[0060] Preferably, the Ar contains at least one deuterium, while L c It contains at least one deuterium.

[0061] Preferably, when Ar is selected from substituted phenyl groups, at least one substituent is selected from deuterium.

[0062] More preferably, when Ar is selected from substituted phenyl groups, the five substituents are selected from deuterium.

[0063] Preferably, the phrase "containing at least one deuterium" includes one deuterium, two deuteriums, three deuteriums, four deuteriums, and five deuteriums.

[0064] Preferably, "containing at least one deuterium" includes at least one deuterium, at least two deuteriums, or at least three deuteriums.

[0065] Preferably, the phrase "containing at least one deuterium" includes at most four or at most five deuteriums.

[0066] Preferably, the "at least one substituent" includes one, two, three, four, or five.

[0067] Preferably, the "at least one substituent" includes at least one substituent, at least two substituents, or at least three substituents.

[0068] Preferably, the "at least one substituent" includes at most four or at most five substituents.

[0069] Preferably, when Ar is selected from substituted naphthyl groups, at least one substituent is selected from deuterium.

[0070] More preferably, when Ar is selected from substituted naphthyl groups, the seven substituents are selected from deuterium.

[0071] Preferably, the phrase "containing at least one deuterium" includes one deuterium, two deuteriums, three deuteriums, four deuteriums, five deuteriums, six deuteriums, and seven deuteriums.

[0072] Preferably, "containing at least one deuterium" includes at least one deuterium, at least two deuteriums, or at least three deuteriums.

[0073] Preferably, the phrase "containing at least one deuterium" includes at most six or at most seven deuterium.

[0074] Preferably, the "at least one substituent" includes one, two, three, four, five, six, or seven.

[0075] Preferably, the "at least one substituent" includes at least one substituent, at least two substituents, or at least three substituents.

[0076] Preferably, the "at least one substituent" includes at most four substituents, at most five substituents, at most six substituents, or at most seven substituents.

[0077] Preferably, when Ar is selected from substituted phenyl groups, at least one substituent is selected from alkyl, cycloalkyl, or adjacent substituents connected to form a saturated or unsaturated aliphatic ring.

[0078] Preferably, when Ar is selected from substituted phenyl groups, at least one substituent is selected from alkyl groups.

[0079] More preferably, when Ar is selected from substituted phenyl groups, at least one substituent is selected from methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, tert-butyl.

[0080] Preferably, when Ar is selected from substituted phenyl groups, at least one substituent is selected from cycloalkyl groups.

[0081] More preferably, when Ar is selected from substituted phenyl groups, at least one substituent is selected from cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel.

[0082] Preferably, adjacent substituents in Ar can be linked to form a saturated or unsaturated aliphatic ring, and more preferably, adjacent substituents in Ar can be linked to form a 3- to 7-membered saturated or unsaturated aliphatic ring.

[0083] Preferably, when Ar is selected from substituted phenyl groups and adjacent substituents are linked to form saturated or unsaturated aliphatic rings, the adjacent substituents can be linked to form 3- to 7-membered saturated or unsaturated aliphatic rings.

[0084] More preferably, adjacent substituents can be linked to form a 5- or 6-membered saturated or unsaturated aliphatic ring. See the example below:

[0085] The asterisk (*) represents the site where the benzene ring is fused.

[0086] Preferably, when Ar is selected from substituted naphthyl, at least one substituent is selected from alkyl, cycloalkyl, or adjacent substituents connected to form a saturated or unsaturated aliphatic ring.

[0087] Preferably, when Ar is selected from substituted naphthyl groups, at least one substituent is selected from alkyl groups.

[0088] More preferably, when Ar is selected from substituted naphthyl, at least one substituent is selected from methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, tert-butyl.

[0089] Preferably, when Ar is selected from substituted naphthyl groups, at least one substituent is selected from cycloalkyl groups.

[0090] More preferably, when Ar is selected from substituted naphthyl, at least one substituent is selected from cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel.

[0091] Preferably, the Ar is selected from one of the following groups:

[0092]

[0093] The R a The ingredient is selected from one or more of deuterium, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, adamantyl, and norbornel, wherein, when substituted with multiple substituents, the multiple substituents may be the same or different from each other, or adjacent substituents may be linked to form a ring; 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, and adamantyl, and when substituted by multiple substituents, the multiple substituents may be the same or different from each other;

[0094] The a1 is 1, 2, 3, 4, 5, 6, or 7; the a2 is 1, 2, 3, 4, or 5; the a3 is 0, 1, 2, 3, 4, 5, 6, or 7; the a4 is 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; the a5 is 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; the a6 is 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; and the a7 is 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, or 13.

[0095] More preferably, the Ar is selected from any one of the following groups:

[0096]

[0097] Most preferably, the Ar is selected from any one of the following groups:

[0098]

[0099] Preferably, the L a L b L c Independently selected from single bonds or one of the following groups:

[0100]

[0101] The most preferred option is the L a L b L c Independently selected from single bonds or one of the following groups:

[0102]

[0103]

[0104] Preferably, the R m R n Independently selected from hydrogen, deuterium, methyl, ethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, or any one of the following groups, or adjacent R m Adjacent R n They can be linked together to form benzene rings or naphthalene rings.

[0105]

[0106] Most preferably, the triarylamine derivative represented by Formula I is selected from any one of the following compounds:

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114] The organic light-emitting device of the present invention further includes a second hole transport layer in the hole transport layer, wherein the second hole transport layer contains a triamine compound represented by Formula II.

[0115]

[0116] In Formula II, at least one of Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 is selected from the groups shown in Formula 1-1 or Formula 1-2, and the others are independently selected from the groups shown in Formula 1-3:

[0117]

[0118] R4~R 11 The alkyl group is independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, or substituted or unsubstituted C6-C25 aryl, or two adjacent substituents are bonded together to form a cyclic structure, wherein R8, R9, and R1 are ...3-C12 cycloalkyl, or substituted or unsubstituted C6-C25 aryl, or two adjacent substituents are bonded together to form a cyclic structure, wherein R8, R9, and R1 are selected from hydrogen, deuterium, substituted or unsubstituted C 10 R 11 There is one and only one carbon atom that serves as the connection site with L0;

[0119] The R0 groups are selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, canyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, or two adjacent R0 groups can be bonded together to form a cyclic structure.

[0120] The R z The same or different Rs are selected from one of hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, canyl, phenyl, naphthyl, biphenyl, deuterated phenyl, deuterated naphthyl, deuterated biphenyl, or any two adjacent Rs. z The groups can bond together to form saturated or unsaturated three-membered, four-membered, five-membered, six-membered, or seven-membered aliphatic ring groups; there is one and only one R. z The corresponding carbon atom is the site connected to bridging L1 to L6; wherein R z It can also be R zz Replaced by, R zzIt 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, stilbene, spirofluorenyl, 9,9-dimethylfluorenyl, and 9,9-diphenylfluorenyl, wherein when substituted with multiple substituents, the multiple substituents may be the same as or different from each other;

[0121] R1, R2, and R3 are independently selected from one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, and substituted or unsubstituted C6-C25 aryl.

[0122] L1, L2, L3, L4, L5, and L6 are independently selected from one of the following: single bond, substituted or unsubstituted C6-C30 arylene group, substituted or unsubstituted C3-C30 aliphatic ring, and fused and cycloalgyl groups of C6-C30 aromatic ring.

[0123] Preferably, Formula II is selected from one of the groups shown in a to c below:

[0124]

[0125] Preferably, in Formula II, Ar1, Ar2, Ar3, Ar4, Ar5 or Ar6 are selected from the groups shown in Formula 1-1 or Formula 1-2, and the rest are independently selected from the groups shown in Formula 1-3.

[0126] Preferably, in Formula II, Ar1 and Ar2, Ar1 and Ar3, Ar1 and Ar5, Ar3 and Ar4, Ar3 and Ar5, or Ar5 and Ar6 are selected from the groups shown in Formula 1-1 or Formula 1-2, and the rest are independently selected from the groups shown in Formula 1-3.

[0127] Preferably, in Formula II, Ar1, Ar2 and Ar3, Ar1, Ar2 and Ar5, Ar1, Ar3 and Ar5, Ar3, Ar4 and Ar5, or Ar3, Ar5 and Ar6 are selected from the groups shown in Formula 1-1 or Formula 1-2, and the rest are independently selected from the groups shown in Formula 1-3.

[0128] Preferably, in Formula II, Ar1, Ar2, Ar3 and Ar4, Ar1, Ar2, Ar3 and Ar5, Ar1, Ar2, Ar5 and Ar6, Ar1, Ar3, Ar4 and Ar5, Ar1, Ar3, Ar5 and Ar6, or Ar3, Ar4, Ar5 and Ar6 are selected from the groups shown in Formula 1-1 or Formula 1-2, and the rest are independently selected from the groups shown in Formula 1-3.

[0129] Preferably, in Formula II, Ar1, Ar2, Ar3, Ar4 and Ar5, Ar1, Ar2, Ar4, Ar5 and Ar6, or Ar1, Ar3, Ar4, Ar5 and Ar6 are selected from the groups shown in Formula 1-1 or Formula 1-2, and the rest are independently selected from the groups shown in Formula 1-3.

[0130] Preferably, in Formula II, Ar1, Ar2, Ar3, Ar4, Ar5 and Ar6 are selected from the groups shown in Formula 1-1 or Formula 1-2.

[0131] Preferably, in formula 1-1 or formula 1-2, R4~R 11 The substituent is independently selected from one of hydrogen, deuterium, methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, adamantyl, norbornyl, canyl, tetrahydronaphthyl, indanyl, benzocyclobutyl, benzocycloheptyl, anthracene, phenanthrene, phenylene, spirofluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, wherein the substituent is selected from one or more substituents in the group consisting of deuterium, methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, adamantyl, norbornyl, canyl, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, naphthyl, deuterated naphthyl terphenyl, or two adjacent substituents bonded together to form a cyclic structure; wherein, in Formula 1-1, R8, R9, R 10 R 11 There is one and only one carbon atom that serves as the connection site with L0.

[0132] Preferably, in Formula 1-1, R0 is selected from one of methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, phenyl, naphthyl, biphenyl, deuterated phenyl, deuterated naphthyl, deuterated biphenyl, or two adjacent R0 can be bonded together to form the following cyclic structure:

[0133] Wherein R 12 ~R 19 Independently selected from one of hydrogen, deuterium, methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, adamantyl, norbornel, canyl, tetrahydronaphthyl, indanyl, benzocyclobutyl, benzocycloheptyl, phenyl, deuterated phenyl, tolyl, naphthyl, deuterated naphthyl, biphenyl, terphenyl, deuterated biphenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, or R 12 ~R 19 Two adjacent substituents are linked to form a benzene ring or naphthalene ring; * indicates the linking site.

[0134] More preferably, formula 1-1 is selected from one of the following groups:

[0135]

[0136]

[0137] Wherein, the R0 groups are selected from one of the following groups, either identically or differently: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, canyl, phenyl, naphthyl, biphenyl, deuterated phenyl, deuterated naphthyl, deuterated biphenyl, or two adjacent R0 groups can be bonded together to form the following cyclic structure: * indicates a connection point.

[0138] Preferably, formulas 1-2 are selected from one of the following groups:

[0139]

[0140] Preferably, formulas 1-3 are selected from one of the following groups:

[0141]

[0142] Preferably, L1, L2, L3, L4, L5, and L6 are independently selected from single bonds or one of the following groups:

[0143]

[0144]

[0145] Preferably, L1, L2, L3, L4, L5, and L6 are independently selected from single bonds or one of the following groups:

[0146]

[0147] More preferably, L1, L2, L3, L4, L5, and L6 are independently selected from single bonds or one of the following groups:

[0148]

[0149] Preferably, R1, R2, and R3 are independently selected from one of hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, canyl, phenyl, naphthyl, and biphenyl, or independently selected from the above groups substituted with one or more deuterium groups.

[0150] Most preferably, the triamine compound represented by Formula II is selected from any one of the following compounds:

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160] In the organic light-emitting device of the present invention, the light-emitting layer material includes a host material and a guest material. The host material can be selected from 4,4'-bis(9-carbazole)biphenyl (CBP), 9,10-bis(2-naphthyl)anthracene (ADN), 4,4-bis(9-carbazole)biphenyl (CPB), 9,9'-(1,3-phenyl)bis-9H-carbazole (mCP), and 4,4',4”-tris(carbazole-9-yl)triphenylamine. Materials such as TCTA, 9,10-bis(1-naphthyl)anthracene (α-AND), N,N'-bis-(1-naphthyl)-N,N'-diphenyl-[1,1':4',1”:4”,1”'-tetraphenyl]-4,4”'-diamino (4PNPB), and 1,3,5-tris(9-carbazolyl)benzene (TCP) are also mentioned. In addition to the above materials and combinations thereof, the host material for the luminescent layer may also include other known materials suitable for use as the luminescent layer.

[0161] The luminescent layer guest material can be 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)), bis(phenylisoquinoline)(2,2,6,6-tetramethylheptane-3,5-diacid)iridium(III)Ir(dpm)(piq)2, etc. In addition to the above materials, the luminescent layer guest material can also include other known materials suitable for use as the luminescent layer.

[0162] 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 mass percentage 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%.

[0163] In the organic light-emitting device 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), and 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), 4,7-diphenyl-1,10-phenanthroline (Bphen), etc. Besides the above materials and combinations thereof, the electron transport material may also include other known materials suitable for serving as the electron transport layer. The electron transport material can be a single material or a mixture of other suitable materials.

[0164] In the organic light-emitting device of the present 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, 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 the present invention is selected from lithium fluoride (LiF), lithium 8-hydroxyquinoline (Liq), etc.

[0165] 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 thin films from these electrode materials using methods such as vapor deposition or sputtering. In addition to the above materials and combinations thereof, cathode materials may also include other known materials suitable for use as cathodes.

[0166] 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.

[0167] The organic layer thickness of the organic light-emitting device of the present invention is selected from 0.5 nm to 500 nm, preferably 1 nm to 300 nm, and more preferably 1 nm to 120 nm. The thickness of the organic layer is appropriately changed according to the type of material used in the organic light-emitting device and the thickness of other layers.

[0168] 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. If the thickness is too large, the driving voltage of the device increases, which is undesirable. Therefore, the thickness of the 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.

[0169] Regarding the order, number, and thickness of layers in organic light-emitting devices, the appropriate selection can be made by considering luminous efficiency and device lifespan.

[0170] There are no particular restrictions on the preparation and formation methods of each layer in the organic light-emitting device. 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.

[0171] The organic light-emitting device 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.

[0172] The triarylamine derivatives represented by Formula I and the triamine compounds represented by Formula II can be obtained by the following methods:

[0173] Formula I reaction formula:

[0174]

[0175] The preparation method of the triarylamine derivative of Formula I of the present invention can be obtained by the conventional Buchwald-Hartwig coupling reaction in the art. That is, under a nitrogen atmosphere, amine compound x and halogen compound y undergo a Buchwald-Hartwig coupling reaction to obtain intermediate X, which then undergoes a Buchwald-Hartwig coupling reaction with halogen compound z. The reaction is carried out under appropriate catalysts, organic bases, ligands, solutions, and appropriate temperatures to obtain the corresponding compound of Formula I, wherein X... a X b Such as compounds containing Cl, Br or I.

[0176] Formula II reaction formula:

[0177]

[0178] The triamine compound undergoes a Buchwald-Hartwig coupling reaction to yield intermediates A, B, and C; the starting material g and intermediate A undergo a Buchwald-Hartwig coupling reaction to yield intermediate I; intermediate I and intermediate B undergo a Buchwald-Hartwig coupling reaction to yield intermediate II; intermediate II and intermediate C undergo a Buchwald-Hartwig coupling reaction to finally yield the compound of formula I, wherein halogen compounds X1, X2, X3, X4, X5, and X6 are compounds containing Cl, Br, or I.

[0179] The present invention does not impose any particular restrictions on the source of the raw materials used in the above-mentioned reactions. Commercially available raw materials or preparation methods known to those skilled in the art can be used to obtain the triarylamine derivatives represented by Formula I and the triamine compounds represented by Formula II of the present invention.

[0180] The present invention does not impose any special limitations on the above-mentioned reactions; conventional reactions known to those skilled in the art can be used.

[0181] 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 devices according to the invention within the entire scope disclosed without inventive effort.

[0182] Description of raw materials, reagents, and characterization equipment:

[0183] 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.

[0184] Mass spectrometry was performed using a Waters G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer, with chloroform as the solvent.

[0185] 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.

[0186] Synthesis Example 1: Preparation of Compound 6

[0187]

[0188] Synthetic intermediate X-6

[0189] Under nitrogen protection, toluene (300 mL), x-6 (8.91 g, 50.00 mmol), y-6 (19.76 g, 50.00 mmol), palladium acetate (0.17 g, 0.75 mmol), sodium tert-butoxide (9.61 g, 100.00 mmol), and tri-tert-butylphosphine (3 mL of 0.50 M toluene solution) were added sequentially to a reaction flask. The mixture was stirred and heated under reflux for 3 hours. After the reaction was complete, the reaction solution was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic phase was collected, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation. Recrystallization was performed using toluene:ethanol (10:1) to obtain intermediate X-6 (20.94 g, 85%). The purity of the solid was ≥99.83% as determined by HPLC. Mass spectrometry m / z: 492.2565 (theoretical value: 492.2552).

[0190] Synthetic compound 6

[0191] Under nitrogen protection, toluene (200 ml), intermediate X-6 (12.32 g, 25.00 mmol), z-6 (6.83 g, 25.00 mmol), Pd2(dba)3 (0.23 g, 0.25 mmol), sodium tert-butoxide (4.81 g, 50.00 mmol), and BINAP (0.25 g, 0.40 mmol) were added sequentially to a reaction flask. The mixture was stirred and heated under reflux for 4 hours. After the reaction was complete, the reaction solution was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic phase was collected, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation. The mixture was recrystallized from toluene to give compound 6 (9.86 g, 72%). The purity of the solid was ≥99.99% as determined by HPLC. Mass spectrometry m / z: 684.3476 (theoretical value: 684.3491). Theoretical elemental content (%) C 52 H 28 D9N: C, 91.19; H, 6.77; N, 2.05. Measured elemental content (%): C, 91.21; H, 6.76; N, 2.08.

[0192] Synthesis Example 2: Preparation of Compound 11

[0193]

[0194] Following the method of Example 1, x-6 was replaced with an equimolar amount of x-11, and z-6 was replaced with an equimolar amount of z-11, yielding compound 11 (10.45 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 756.3571 (theoretical value: 756.3553). Theoretical elemental content (%) C 58 H 36 D5N: C, 92.03; H, 6.12; N, 1.85. Measured elemental content (%): C, 92.06; H, 6.11; N, 1.87.

[0195] Synthesis Example 3: Preparation of Compound 14

[0196]

[0197] Following the method of Example 1, x-6 was replaced with an equimolar amount of x-14 to obtain compound 14 (10.11 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 711.3854 (theoretical value: 711.3865). Theoretical elemental content (%) C 54 H 49 N: C, 91.10; H, 6.94; N, 1.97. Measured element content (%): C, 91.08; H, 6.95; N, 1.95.

[0198] Synthesis Example 4: Preparation of Compound 26

[0199]

[0200] Following the method of Example 1, x-6 was replaced with an equimolar amount of x-26 to obtain compound 26 (11.82 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 656.3218 (theoretical value: 656.3209). Theoretical elemental content (%) C 50 H 28 D7N: C, 91.42; H, 6.44; N, 2.13. Measured elemental content (%): C, 91.45; H, 6.42; N, 2.12.

[0201] Synthesis Example 5: Preparation of Compound 36

[0202]

[0203] Following the method of Example 1, x-6 was replaced with an equimolar amount of x-36 to obtain compound 36 (10.13 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 733.3722 (theoretical value: 733.3709). Theoretical elemental content (%) C 56 H 47 N: C, 91.64; H, 6.45; N, 1.91. Measured element content (%): C, 91.61; H, 6.47; N, 1.89.

[0204] Synthesis Example 6: Preparation of Compound 41

[0205]

[0206] Following the method of Example 1, x-6 was replaced with an equimolar amount of x-41, y-6 with an equimolar amount of y-41, and z-6 with an equimolar amount of z-41, yielding compound 41 (10.08 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 709.3726 (theoretical value: 709.3709). Theoretical elemental content (%) C 54 H 47 N: C, 91.35; H, 6.67; N, 1.97. Measured elemental content (%): C, 91.36; H, 6.65; N, 1.95.

[0207] Synthesis Example 7: Preparation of Compound 49

[0208]

[0209] Following the method of Example 1, x-6 was replaced with an equimolar amount of x-49, and z-6 was replaced with an equimolar amount of z-49, yielding compound 49 (10.60 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 756.3541 (theoretical value: 756.3553). Theoretical elemental content (%) C 58 H 36 D5N: C, 92.03; H, 6.12; N, 1.85. Measured elemental content (%): C, 92.04; H, 6.15; N, 1.83.

[0210] Synthesis Example 8: Preparation of Compound 52

[0211]

[0212] Following the method of Example 1, intermediate X-6 was replaced with an equimolar amount of intermediate X-49, and z-6 was replaced with an equimolar amount of z-52, yielding compound 52 (10.98 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 806.3725 (theoretical value: 806.3709). Theoretical elemental content (%) C 62 H 38 D5N: C, 92.27; H, 5.99; N, 1.74. Measured elemental content (%): C, 92.25; H, 5.97; N, 1.75.

[0213] Synthesis Example 9: Preparation of Compound 85

[0214]

[0215] Following the method of Example 1, x-6 was replaced with an equimolar amount of x-85, and z-6 was replaced with an equimolar amount of z-41, yielding compound 85 (10.22 g). HPLC analysis showed a solid purity ≥99.99%. Mass spectrometry m / z: 719.3477 (theoretical value: 719.3490). Theoretical elemental content (%) C 55 H 37 D4N: C, 91.76; H, 6.30; N, 1.95. Measured elemental content (%): C, 91.73; H, 6.28; N, 1.97.

[0216] Synthesis Example 10: Preparation of Compound 102

[0217]

[0218] Following the method of Example 1, x-6 was replaced with an equimolar amount of x-102 to obtain compound 102 (10.33 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 667.3251 (theoretical value: 667.3239). Theoretical elemental content (%) C 51 H 41 N: C, 91.72; H, 6.19; N, 2.10. Measured elemental content (%): C, 91.78; H, 6.13; N, 2.10.

[0219] Synthetic Example 11: Preparation of Compound 133

[0220]

[0221] Following the method of Example 1, x-6 was replaced with an equimolar amount of x-36, and z-6 was replaced with an equimolar amount of z-133, yielding compound 133 (10.18 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 737.3972 (theoretical value: 737.3960). Theoretical elemental content (%) C 56 H 43 D4N: C, 91.14; H, 6.96; N, 1.90. Measured elemental content (%): C, 91.16; H, 6.95; N, 1.93.

[0222] Synthesis Example 12: Preparation of Compound 134

[0223]

[0224] Following the method of Example 1, x-6 was replaced with an equimolar amount of x-134, and y-6 was replaced with an equimolar amount of y-134, yielding compound 134 (10.03 g). HPLC analysis showed a solid purity ≥99.99%. Mass spectrometry m / z: 795.4625 (theoretical value: 795.4618). Theoretical elemental content (%) C 60 H 37 D 12 N: C, 90.52; H, 7.72; N, 1.76. Measured elemental content (%): C, 90.56; H, 7.70; N, 1.74.

[0225] Synthesis Example 13: Preparation of Compound 201

[0226]

[0227] Following the method of Example 1, x-6 was replaced with an equimolar amount of x-201, and z-6 was replaced with an equimolar amount of z-201, yielding compound 201 (11.37 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 835.4161 (theoretical value: 835.4178). Theoretical elemental content (%) C 64 H 53 N: C, 91.94; H, 6.39; N, 1.68. Measured elemental content (%): C, 91.96; H, 6.36; N, 1.67.

[0228] Synthesis Example 14: Preparation of Compound 235

[0229]

[0230] Following the method of Example 1, x-6 was replaced with an equimolar amount of x-235, and z-6 was replaced with an equimolar amount of z-235, yielding compound 235 (10.72 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 776.4131 (theoretical value: 776.4117). Theoretical elemental content (%) C 59 H 36 D9N: C, 91.19; H, 7.00; N, 1.80. Measured elemental content (%): C, 91.21; H, 7.03; N, 1.78.

[0231] Synthesis Example 15: Preparation of Compound 242

[0232]

[0233] Following the method of Example 1, x-6 was replaced with an equimolar amount of x-242, and z-6 was replaced with an equimolar amount of y-6, yielding compound 242 (10.32 g). HPLC analysis showed a solid purity ≥99.99%. Mass spectrometry m / z: 726.3072 (theoretical value: 726.3083). Theoretical elemental content (%) C 56 H 30 D5N: C, 92.53; H, 5.55; N, 1.93. Measured elemental content (%): C, 92.55; H, 5.52; N, 1.91.

[0234] Synthesis Example 16: Preparation of Compound 258

[0235]

[0236] Following the method of Example 1, x-6 was replaced with an equimolar amount of x-258, y-6 with an equimolar amount of y-258, and z-6 with an equimolar amount of z-258, yielding compound 258 (12.23 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 979.4184 (theoretical value: 979.4178). Theoretical elemental content (%) C 76 H 53 N: C, 93.12; H, 5.45; N, 1.43. Measured element content (%): C, 93.15; H, 5.43; N, 1.42.

[0237] Synthesis Example 17: Preparation of Compound 275

[0238]

[0239] Following the method of Example 1, x-6 was replaced with an equimolar amount of x-275, y-6 with an equimolar amount of y-275, and z-6 with an equimolar amount of z-275, yielding compound 275 (9.96 g). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 691.3225 (theoretical value: 691.3239). Theoretical elemental content (%) C 53 H 41 N: C, 92.00; H, 5.97; N, 2.02. Measured elemental content (%): C, 92.02; H, 5.95; N, 2.03.

[0240] Synthesis Example 18: Preparation of Compound 280

[0241]

[0242] Following the method of Example 1, x-6 was replaced with an equimolar amount of x-134, y-6 with an equimolar amount of y-280, and z-6 with an equimolar amount of z-280, yielding compound 280 (11.26 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 957.4341 (theoretical value: 957.4335). Theoretical elemental content (%) C 74 H 55 N: C, 92.75; H, 5.79; N, 1.46. Measured element content (%): C, 92.78; H, 5.75; N, 1.47.

[0243] Synthetic Example 19: Preparation of Compound 295

[0244]

[0245] Following the method of Example 1, x-6 was replaced with an equimolar amount of x-295, y-6 with an equimolar amount of y-295, and z-6 with an equimolar amount of z-295, yielding compound 295 (12.04 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 977.5910 (theoretical value: 977.5900). Theoretical elemental content (%) C 74 H 75 N: C, 90.84; H, 7.73; N, 1.43. Measured element content (%): C, 90.82; H, 7.72; N, 1.46.

[0246] Synthesis Example 20: Preparation of Compound 299

[0247]

[0248] Following the method of Example 1, x-6 was replaced with an equimolar amount of x-299, y-6 with an equimolar amount of y-41, and z-6 with an equimolar amount of z-299, yielding compound 299 (11.91 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 901.4632 (theoretical value: 901.4648). Theoretical elemental content (%) C 69 H 59 N: C, 91.86; H, 6.59; N, 1.55. Measured element content (%): C, 91.85; H, 6.61; N, 1.57.

[0249] Synthesis Example 21: Preparation of Compound 302

[0250]

[0251] Following the method of Example 1, x-6 was replaced with an equimolar amount of x-302, y-6 with an equimolar amount of y-302, and z-6 with an equimolar amount of z-41, yielding compound 302 (10.34 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 779.3557 (theoretical value: 779.3552). Theoretical elemental content (%) C 60 H 45 N: C, 92.39; H, 5.82; N, 1.80. Measured element content (%): C, 92.42; H, 5.80; N, 1.79.

[0252] Synthesis Example 22: Preparation of Compound 309

[0253]

[0254] Following the method of Example 1, x-6 was replaced with an equimolar amount of x-309, and y-6 was replaced with an equimolar amount of y-258, yielding compound 309 (10.61 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 757.3724 (theoretical value: 757.3709). Theoretical elemental content (%) C 58 H 47 N: C, 91.90; H, 6.25; N, 1.85. Measured element content (%): C, 91.88; H, 6.26; N, 1.83.

[0255] Synthesis Example 23: Preparation of Compound 1-1

[0256]

[0257] Synthetic intermediate A-1-1

[0258] Under nitrogen protection, a-1-1 (8.38 g, 90.00 mmol), z-6 (24.59 g, 90.00 mmol), and sodium tert-butoxide (12.49 g, 130.00 mmol) were dissolved in 300 mL of toluene. Pd(dppf)Cl2 (0.69 g, 0.95 mmol) and P(t-Bu)3 (0.19 g, 0.95 mmol) were added with stirring. The mixture of the above reactants was heated under reflux for 4 h. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. The mixture was recrystallized from ethyl acetate to give intermediate A-1-1 (22.09 g, yield 86%). HPLC analysis showed a solid purity ≥99.82%. Mass spectrometry m / z: 285.1503 (theoretical value: 285.1517).

[0259] Synthetic compound 1-1

[0260] Under nitrogen protection, g-1-1 (6.30 g, 20 mmol), intermediate A-1-1 (17.12 g, 60 mmol), and sodium tert-butoxide (3.84 g, 40 mmol) were dissolved in 150 mL of toluene. Pd2(dba)3 (0.23 g, 0.25 mmol) and P(t-Bu)3 (0.06 g, 0.30 mmol) were added with stirring. The mixture of the above reactants was heated under reflux for 5 h. After the reaction was complete, the reaction mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. The mixture was recrystallized from toluene to give compound 1-1 (12.25 g, 66%). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 927.4568 (theoretical value: 927.4552). Theoretical elemental content (%) C 69 H 57 N3: C, 89.28; H, 6.19; N, 4.53. Measured elemental content (%): C, 89.25; H, 6.18; N, 4.55.

[0261] Synthesis Example 24: Preparation of Compounds 1-3

[0262]

[0263] Synthetic intermediate A-1-3

[0264] Under nitrogen protection, x-134 (15.23 g, 90.00 mmol), z-6 (24.59 g, 90.00 mmol), and sodium tert-butoxide (12.49 g, 130 mmol) dissolved in 300 mL toluene were added to a reaction flask. Pd(dppf)Cl2 (0.79 g, 1.08 mmol) was added with stirring, and the mixture was heated to reflux for 3 h. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallization from ethyl acetate yielded intermediate A-1-3 (27.98 g, 86%), with a solid purity ≥99.71% as determined by HPLC. Mass spectrometry m / z: 361.1847 (theoretical value: 361.1830).

[0265] Synthetic intermediate B-1-3

[0266] Under nitrogen protection, x-134 (11.85 g, 70.00 mmol), z-133 (19.40 g, 70.00 mmol), and sodium tert-butoxide (10.57 g, 110 mmol) were dissolved in 270 mL of toluene. Palladium acetate (0.19 g, 0.84 mmol) and P(t-Bu)3 (0.17 g, 0.84 mmol) were added with stirring. The mixture of the above reactants was heated under reflux for 3.5 h. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallization from toluene / methanol (v / v 10:1) yielded intermediate B-1-3 (21.49 g, 84%), with a solid purity ≥99.75% as determined by HPLC. Mass spectrometry m / z: 365.2069 (theoretical value: 365.2082).

[0267] Synthetic intermediate I-1-3

[0268] Under nitrogen protection, g-1-3 (13.55 g, 60.00 mmol), intermediate A-1-3 (21.69 g, 60.00 mmol), and sodium tert-butoxide (9.61 g, 100 mmol) were dissolved in 210 mL of toluene. Palladium acetate (0.15 g, 0.69 mmol) and P(t-Bu)3 (0.14 g, 0.69 mmol) were added with stirring. The mixture of the above reactants was heated under reflux for 4.5 h. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. The mixture was purified by silica gel column chromatography with n-hexane / dichloromethane (9:1 v / v) to obtain intermediate I-1-3 (22.49 g, 74%), with a solid purity ≥99.83% as determined by HPLC. Mass spectrometry m / z: 505.1378 (theoretical value: 505.1364).

[0269] Synthetic compounds 1-3

[0270] Under nitrogen protection, intermediates I-1-3 (10.13 g, 20.00 mmol), B-1-3 (14.62 g, 40.00 mmol), and sodium tert-butoxide (5.77 g, 60 mmol) were dissolved in 150 mL of toluene. Pd₂(dba)₃ (0.23 g, 0.25 mmol) and X-Phos (0.14 g, 0.30 mmol) were added with stirring. The mixture of the above reactants was heated under reflux for 5 h. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallization from toluene yielded compound 1-3 (14.67 g, 63%), with a solid purity ≥ 99.94% as determined by HPLC. Mass spectrometry m / z: 1163.5978 (theoretical value: 1163.5994). Theoretical elemental content (%) C 87 H 61 D8N3: C, 89.73; H, 6.66; N, 3.61. Measured elemental content (%): C, 89.75; H, 6.65; N, 3.63.

[0271] Synthetic Example 25: Preparation of Compounds 1-15

[0272]

[0273] Following the method of Example 23, a-1-1 was replaced with an equimolar amount of a-1-15 to obtain compound 1-15 (13.80 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 1077.5039 (theoretical value: 1077.5022). Theoretical elemental content (%) C 81 H 63 N3: C, 90.21; H, 5.89; N, 3.90. Measured elemental content (%): C, 90.19; H, 5.86; N, 3.92.

[0274] Synthetic Example 26: Preparation of Compounds 1-44

[0275]

[0276] According to the method of Example 24, z-6 in synthetic intermediate A-1-3 was replaced with an equimolar amount of b-1-44, x-134 in synthetic intermediate B-1-3 was replaced with an equimolar amount of a-1-1, and z-133 in synthetic intermediate B-1-3 was replaced with an equimolar amount of b-1-44, yielding compound 1-44 (12.86 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 1003.4849 (theoretical value: 1003.4865). Theoretical elemental content (%) C 75 H 61 N3: C, 89.69; H, 6.12; N, 4.18. Measured elemental content (%): C, 89.72; H, 6.11; N, 4.17.

[0277] Synthetic Example 27: Preparation of Compounds 1-73

[0278]

[0279] Following the method of Example 23, a-1-1 was replaced with an equimolar amount of x-36 to obtain compound 1-73 (16.24 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 1329.7821 (theoretical value: 1329.7839). Theoretical elemental content (%) C 99 H 99 N3: C, 89.34; H, 7.50; N, 3.16. Measured elemental content (%): C, 89.36; H, 7.47; N, 3.15.

[0280] Synthetic Example 28: Preparation of Compounds 1-83

[0281]

[0282] Following the method of Example 23, a-1-1 was replaced with an equimolar amount of x-242 to obtain compound 1-83 (12.45 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 942.5477 (theoretical value: 942.5494). Theoretical elemental content (%) C 69 H 42 D 15 N3: C, 87.85; H, 7.69; N, 4.45. Measured element content (%): C, 87.83; H, 7.71; N, 4.48.

[0283] Synthetic Example 29: Preparation of Compounds 1-147

[0284]

[0285] According to the method of Example 24, x-134 in synthetic intermediate A-1-3 was replaced with an equimolar amount of x-6, x-134 in synthetic intermediate B-1-3 was replaced with an equimolar amount of a-1-1, and z-133 in synthetic intermediate B-1-3 was replaced with an equimolar amount of d-1-147, yielding compound 1-147 (12.32 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 932.4816 (theoretical value: 932.4804). Theoretical elemental content (%) C 69 H 44 D9N3: C, 88.80; H, 6.69; N, 4.50. Measured elemental content (%): C, 88.77; H, 6.71; N, 4.48.

[0286] Synthetic Example 30: Preparation of Compounds 1-161

[0287]

[0288] Following the method of Example 23, z-6 was replaced with an equimolar amount of b-1-161 to obtain compound 1-161 (13.80 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 1077.5035 (theoretical value: 1077.5022). Theoretical elemental content (%) C 81 H 63 N3: C, 90.21; H, 5.89; N, 3.90. Measured elemental content (%): C, 90.23; H, 5.91; N, 3.88.

[0289] Synthetic Example 31: Preparation of Compound 1-205

[0290]

[0291] Following the method of Example 23, z-6 was replaced with an equimolar amount of z-258 to obtain compound 1-205 (15.87 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 1299.5475 (theoretical value: 1299.5491). Theoretical elemental content (%) C 99 H 69 N3: C, 91.42; H, 5.35; N, 3.23. Measured elemental content (%): C, 91.44; H, 5.33; N, 3.21.

[0292] Synthetic Example 32: Preparation of Compounds 1-257

[0293]

[0294] According to the method of Example 24, x-134 in synthetic intermediate A-1-3 was replaced with an equimolar amount of a-1-1, z-6 in synthetic intermediate A-1-3 was replaced with an equimolar amount of b-1-257, x-134 in synthetic intermediate B-1-3 was replaced with an equimolar amount of a-1-1, and z-133 in synthetic intermediate B-1-3 was replaced with an equimolar amount of d-1-257, yielding compound 1-257 (13.32 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 1039.5761 (theoretical value: 1039.5743). Theoretical elemental content (%) C 77 H 65 D4N3: C, 88.89; H, 7.07; N, 4.04. Measured elemental content (%): C, 88.92; H, 7.05; N, 4.06.

[0295] Synthesis Example 33: Preparation of Compounds 1-263

[0296]

[0297] According to the method of Example 24, x-134 in synthetic intermediate A-1-3 was replaced with an equimolar amount of a-1-1, z-6 in synthetic intermediate A-1-3 was replaced with an equimolar amount of b-1-263, x-134 in synthetic intermediate B-1-3 was replaced with an equimolar amount of a-1-1, and z-133 in synthetic intermediate B-1-3 was replaced with an equimolar amount of d-1-263, yielding compound 1-263 (12.56 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 965.5479 (theoretical value: 965.5493). Theoretical elemental content (%) C 71 H 51 D 10 N3: C, 88.25; H, 7.40; N, 4.35. Measured elemental content (%): C, 88.27; H, 7.39; N, 4.36.

[0298] Synthesis Example 34: Preparation of Compounds 1-273

[0299]

[0300] According to the method of Example 24, x-134 in synthetic intermediate A-1-3 was replaced with an equimolar amount of a-1-1, z-6 in synthetic intermediate A-1-3 was replaced with an equimolar amount of z-280, x-134 in synthetic intermediate B-1-3 was replaced with an equimolar amount of a-1-1, and z-133 in synthetic intermediate B-1-3 was replaced with an equimolar amount of d-1-273, yielding compound 1-273 (10.65 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 771.3627 (theoretical value: 771.3613). Theoretical elemental content (%) C 57 H 45 N3: C, 88.68; H, 5.88; N, 5.44. Measured elemental content (%): C, 88.66; H, 5.85; N, 5.46.

[0301] Synthetic Example 35: Preparation of Compounds 1-277

[0302]

[0303] According to the method of Example 24, x-134 in synthetic intermediate A-1-3 was replaced with an equimolar amount of a-1-277, x-134 in synthetic intermediate B-1-3 was replaced with an equimolar amount of c-1-277, and z-133 in synthetic intermediate B-1-3 was replaced with an equimolar amount of z-6, yielding compound 1-277 (13.42 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 1047.5478 (theoretical value: 1047.5491). Theoretical elemental content (%) C 78 H 69 N3: C, 89.36; H, 6.63; N, 4.01. Measured elemental content (%): C, 89.35; H, 6.65; N, 4.04.

[0304] Synthetic Example 36: Preparation of Compounds 1-299

[0305]

[0306] Synthetic intermediate C-1-299

[0307] Under nitrogen protection, x-49 (6.97 g, 40.00 mmol), f-1-299 (11.49 g, 40.00 mmol), and sodium tert-butoxide (7.69 g, 80 mmol) were dissolved in 300 mL of toluene. Palladium acetate (0.11 g, 0.47 mmol) and P(t-Bu)3 (0.10 g, 0.47 mmol) were added with stirring. The mixture of the above reactants was heated under reflux for 4 h. After the reaction was complete, the reaction solution was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallization from ethyl acetate yielded intermediate C-1-299 (12.94 g, 85%), with a solid purity ≥99.72% as determined by HPLC. Mass spectrometry m / z: 380.2314 (theoretical value: 380.2301).

[0308] Synthetic intermediate I-1-299

[0309] Under nitrogen protection, g-1-299 (25.39 g, 80.00 mmol), intermediate A-1-1 (22.83 g, 80.00 mmol), and sodium tert-butoxide (12.49 g, 130 mmol) were dissolved in 300 mL of toluene. Pd(dppf)Cl2 (0.65 g, 0.89 mmol) was added with stirring, and the mixture was heated to reflux for 4 h. Water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. The mixture was purified by silica gel column chromatography with n-hexane / dichloromethane (v / v 10:1) to obtain intermediate I-1-299 (29.63 g, 78%), with a solid purity ≥99.76% as determined by HPLC. Mass spectrometry m / z: 473.0535 (theoretical value: 473.0546).

[0310] Synthetic intermediate II-1-299

[0311] Under nitrogen protection, intermediates I-1-299 (23.74 g, 50.00 mmol), B-1-147 (12.27 g, 50.00 mmol), and sodium tert-butoxide (8.65 g, 90 mmol) were dissolved in 200 mL of toluene. Pd₂(dba)₃ (0.52 g, 0.57 mmol) and P(t-Bu)₃ (0.12 g, 0.57 mmol) were added with stirring. The mixture of the above reactants was heated under reflux for 4.5 h. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. The mixture was purified by silica gel column chromatography with n-hexane / dichloromethane (5:1 v / v) to obtain intermediate II-1-299 (23.97 g, 75%), with a solid purity ≥99.83% as determined by HPLC. Mass spectrometry m / z: 638.2476 (theoretical value: 638.2489).

[0312] Synthetic compound 1-299

[0313] Under nitrogen protection, intermediates II-1-299 (12.78 g, 20 mmol), C-1-299 (7.61 g, 20 mmol), and sodium tert-butoxide (1.92 g, 20 mmol) were dissolved in 125 mL of toluene. Pd₂(dba)₃ (0.11 g, 0.12 mmol) and X-Phos (0.07 g, 0.15 mmol) were added with stirring. The mixture of the above reactants was heated under reflux for 5 h. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallization from toluene yielded compound 1-299 (12.78 g, 65%), with a solid purity ≥ 99.96% as determined by HPLC. Mass spectrometry m / z: 982.5035 (theoretical value: 982.5023). Theoretical elemental content (%) C 73 H 54 D5N3: C, 89.17; H, 6.56; N, 4.27. Measured elemental content (%): C, 89.15; H, 6.53; N, 4.29.

[0314] Synthesis Example 37: Preparation of Compound 1-308

[0315]

[0316] According to the method of Example 24, x-134 in synthetic intermediate A-1-3 was replaced with an equimolar amount of a-1-1, z-6 in synthetic intermediate A-1-3 was replaced with an equimolar amount of z-201, x-134 in synthetic intermediate B-1-3 was replaced with an equimolar amount of x-102, and z-133 in synthetic intermediate B-1-3 was replaced with an equimolar amount of d-1-273, yielding compound 1-308 (12.57 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 981.5036 (theoretical value: 981.5022). Theoretical elemental content (%) C 73 H 63 N3: C, 89.26; H, 6.46; N, 4.28. Measured elemental content (%): C, 89.28; H, 6.45; N, 4.25.

[0317] Synthetic Example 38: Preparation of Compounds 1-310

[0318]

[0319] Following the method of Example 24, x-134 in synthetic intermediate A-1-3 was replaced with an equimolar amount of a-1-1, z-6 in synthetic intermediate A-1-3 was replaced with an equimolar amount of z-235, and intermediate B-1-3 was replaced with an equimolar amount of intermediate B-1-147, yielding compound 1-310 (12.41 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 939.4571 (theoretical value: 939.4552). Theoretical elemental content (%) C 70 H 57 N3: C, 89.42; H, 6.11; N, 4.47. Measured elemental content (%): C, 89.44; H, 6.12; N, 4.45.

[0320] Synthetic Example 39: Preparation of Compounds 1-312

[0321]

[0322]

[0323] According to the method of Example 24, x-134 in synthetic intermediate A-1-3 was replaced with an equimolar amount of a-1-1, z-6 in synthetic intermediate A-1-3 was replaced with an equimolar amount of z-133, x-134 in synthetic intermediate B-1-3 was replaced with an equimolar amount of x-309, and z-133 in synthetic intermediate B-1-3 was replaced with an equimolar amount of d-1-147, yielding compound 1-312 (13.01 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 1015.5758 (theoretical value: 1015.5743). Theoretical elemental content (%) C 75 H 65 D4N3: C, 88.63; H, 7.24; N, 4.13. Measured elemental content (%): C, 88.65; H, 7.23; N, 4.16.

[0324] Synthetic Example 40: Preparation of Compounds 1-324

[0325]

[0326] According to the method of Example 36, a-1-1 in synthetic intermediate B-1-147 was replaced with an equimolar amount of x-134, d-1-147 in synthetic intermediate B-1-147 was replaced with an equimolar amount of d-1-324, x-49 in synthetic intermediate C-1-299 was replaced with an equimolar amount of e-1-324, and f-1-299 in synthetic intermediate C-1-299 was replaced with an equimolar amount of d-1-273, yielding compound 1-324 (13.11 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 1023.4564 (theoretical value: 1023.4552). Theoretical elemental content (%) C 77 H 57 N3: C, 90.29; H, 5.61; N, 4.10. Measured element content (%): C, 90.31; H, 5.58; N, 4.09.

[0327] Synthetic Example 41: Preparation of Compounds 1-338

[0328]

[0329] According to the method of Example 24, x-134 in synthetic intermediate A-1-3 was replaced with an equimolar amount of a-1-1, z-6 in synthetic intermediate A-1-3 was replaced with an equimolar amount of y-295, x-134 in synthetic intermediate B-1-3 was replaced with an equimolar amount of a-1-1, and z-133 in synthetic intermediate B-1-3 was replaced with an equimolar amount of b-1-338, yielding compound 1-338 (14.60 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 1157.5634 (theoretical value: 1157.5648). Theoretical elemental content (%) C 87 H 71 N3: C, 90.20; H, 6.18; N, 3.63. Measured elemental content (%): C, 90.17; H, 6.17; N, 3.65.

[0330] Synthetic Example 42: Preparation of Compounds 1-344

[0331]

[0332] According to the method of Example 24, x-134 in synthetic intermediate A-1-3 was replaced with an equimolar amount of a-1-1, z-6 in synthetic intermediate A-1-3 was replaced with an equimolar amount of b-1-344, and intermediate B-1-3 was replaced with an equimolar amount of intermediate B-1-147, yielding compound 1-344 (12.64 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 971.4225 (theoretical value: 971.4239). Theoretical elemental content (%) C 73 H 53 N3: C, 90.18; H, 5.49; N, 4.32. Measured elemental content (%): C, 90.16; H, 5.52; N, 4.34.

[0333] Synthetic Example 43: Preparation of Compounds 1-347

[0334]

[0335] According to the method of Example 24, x-134 in synthetic intermediate A-1-3 was replaced with an equimolar amount of a-1-1, z-6 in synthetic intermediate A-1-3 was replaced with an equimolar amount of z-295, x-134 in synthetic intermediate B-1-3 was replaced with an equimolar amount of x-295, and z-133 in synthetic intermediate B-1-3 was replaced with an equimolar amount of d-1-273, yielding compound 1-347 (12.68 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 989.5506 (theoretical value: 989.5524). Theoretical elemental content (%) C 73 H55 D8N3: C, 88.53; H, 7.22; N, 4.24. Measured elemental content (%): C, 88.52; H, 7.24; N, 4.25.

[0336] Synthetic Example 44: Preparation of Compounds 1-349

[0337]

[0338] According to the method of Example 24, x-134 in synthetic intermediate A-1-3 was replaced with an equimolar amount of x-242, z-6 in synthetic intermediate A-1-3 was replaced with an equimolar amount of z-235, x-134 in synthetic intermediate B-1-3 was replaced with an equimolar amount of x-242, z-133 in synthetic intermediate B-1-3 was replaced with an equimolar amount of d-1-349, and g-1-3 was replaced with an equimolar amount of g-1-349, yielding compound 1-349 (15.21 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 1225.7888 (theoretical value: 1225.7873). Theoretical elemental content (%) C 90 H 67 D 18 N3: C, 88.11; H, 8.46; N, 3.43. Measured element content (%): C, 88.14; H, 8.45; N, 3.42.

[0339] Synthetic Example 45: Preparation of Compounds 1-352

[0340]

[0341] According to the method of Example 24, x-134 in synthetic intermediate A-1-3 was replaced with an equimolar amount of a-1-1, z-6 in synthetic intermediate A-1-3 was replaced with an equimolar amount of b-1-352, x-134 in synthetic intermediate B-1-3 was replaced with an equimolar amount of a-1-1, and z-133 in synthetic intermediate B-1-3 was replaced with an equimolar amount of d-1-352, yielding compound 1-352 (15.03 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 1191.5478 (theoretical value: 1191.5491). Theoretical elemental content (%) C 90 H 69 N3: C, 90.64; H, 5.83; N, 3.52. Measured elemental content (%): C, 90.65; H, 5.81; N, 3.54.

[0342] Synthetic Example 46: Preparation of Compound 1-355

[0343]

[0344] According to the method of Example 36, a-1-1 in synthetic intermediate B-1-147 was replaced with an equimolar amount of x-26, d-1-147 in synthetic intermediate B-1-147 was replaced with an equimolar amount of d-1-273, x-49 in synthetic intermediate C-1-299 was replaced with an equimolar amount of e-1-355, and f-1-299 in synthetic intermediate C-1-299 was replaced with an equimolar amount of d-1-273, yielding compound 1-355 (11.78 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 878.4378 (theoretical value: 878.4366). Theoretical elemental content (%) C 65 H 42 D7N3: C, 88.80; H, 6.42; N, 4.78. Measured elemental content (%): C, 88.79; H, 6.44; N, 4.81.

[0345] Synthetic Example 47: Preparation of Compounds 1-359

[0346]

[0347] According to the method of Example 24, x-134 in synthetic intermediate A-1-3 was replaced with an equimolar amount of x-14, z-6 in synthetic intermediate A-1-3 was replaced with an equimolar amount of d-1-273, x-134 in synthetic intermediate B-1-3 was replaced with an equimolar amount of x-242, and z-133 in synthetic intermediate B-1-3 was replaced with an equimolar amount of d-1-359, yielding compound 1-359 (15.91 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 1281.6759 (theoretical value: 1281.6745). Theoretical elemental content (%) C 96 H 67 D 10 N3: C, 89.89; H, 6.84; N, 3.28. Measured elemental content (%): C, 89.92; H, 6.82; N, 3.29.

[0348] Synthetic Example 48: Preparation of Compounds 1-361

[0349]

[0350] According to the method of Example 24, x-134 in synthetic intermediate A-1-3 was replaced with an equimolar amount of a-1-1, z-6 in synthetic intermediate A-1-3 was replaced with an equimolar amount of b-1-361, x-134 in synthetic intermediate B-1-3 was replaced with an equimolar amount of x-302, z-133 in synthetic intermediate B-1-3 was replaced with an equimolar amount of d-1-273, and g-1-3 was replaced with an equimolar amount of g-1-361, yielding compound 1-361 (13.60 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 1061.4726 (theoretical value: 1061.4709). Theoretical elemental content (%) C 80 H 59 N3: C, 90.45; H, 5.60; N, 3.96. Measured elemental content (%): C, 90.46; H, 5.58; N, 3.95.

[0351] Synthesis Example 49: Preparation of Compounds 1-362

[0352]

[0353] According to the method of Example 24, x-134 in synthetic intermediate A-1-3 was replaced with an equimolar amount of x-242, z-6 in synthetic intermediate A-1-3 was replaced with an equimolar amount of b-1-362, x-134 in synthetic intermediate B-1-3 was replaced with an equimolar amount of x-242, and z-133 in synthetic intermediate B-1-3 was replaced with an equimolar amount of d-1-362, yielding compound 1-362 (11.51 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 845.6073 (theoretical value: 845.6061). Theoretical elemental content (%) C 60 H 15 D 34 N3: C, 85.16; H, 9.88; N, 4.97. Measured elemental content (%): C, 85.15; H, 9.91; N, 4.98.

[0354] Synthetic Example 50: Preparation of Compound 1-366

[0355]

[0356] According to the method of Example 24, x-134 in synthetic intermediate A-1-3 was replaced with an equimolar amount of a-1-1, z-6 in synthetic intermediate A-1-3 was replaced with an equimolar amount of z-299, x-134 in synthetic intermediate B-1-3 was replaced with an equimolar amount of x-299, and z-133 in synthetic intermediate B-1-3 was replaced with an equimolar amount of d-1-273, yielding compound 1-366 (13.27 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 1035.5474 (theoretical value: 1035.5491). Theoretical elemental content (%) C 77 H 69 N3: C, 89.23; H, 6.71; N, 4.05. Measured elemental content (%): C, 89.24; H, 6.69; N, 4.03.

[0357] Synthetic Example 51: Preparation of Compound 1-367

[0358]

[0359] According to the method of Example 24, x-134 in synthetic intermediate A-1-3 was replaced with an equimolar amount of a-1-1, z-6 in synthetic intermediate A-1-3 was replaced with an equimolar amount of b-1-367, x-134 in synthetic intermediate B-1-3 was replaced with an equimolar amount of a-1-1, and z-133 in synthetic intermediate B-1-3 was replaced with an equimolar amount of z-52, yielding compound 1-367 (15.48 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 1247.6132 (theoretical value: 1247.6117). Theoretical elemental content (%) C 94 H 77 N3: C, 90.42; H, 6.22; N, 3.37. Measured elemental content (%): C, 90.43; H, 6.24; N, 3.35.

[0360] Synthetic Example 52: Preparation of Compound 1-370

[0361]

[0362] According to the method of Example 24, x-134 in synthetic intermediate A-1-3 was replaced with an equimolar amount of a-1-1, z-6 in synthetic intermediate A-1-3 was replaced with an equimolar amount of b-1-370, x-134 in synthetic intermediate B-1-3 was replaced with an equimolar amount of x-11, and z-133 in synthetic intermediate B-1-3 was replaced with an equimolar amount of d-1-273, yielding compound 1-273 (14.90 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 1181.5475 (theoretical value: 1181.5493). Theoretical elemental content (%) C 89 H 51 D 10 N3: C, 90.40; H, 6.05; N, 3.55. Measured elemental content (%): C, 90.39; H, 6.07; N, 3.58.

[0363] [Comparative Examples 1-17] Device Fabrication Examples:

[0364] Comparative Example 1: Fabrication of organic light-emitting devices using vacuum thermal evaporation. The experimental steps were as follows: ITO-Ag-ITO substrate was washed three times in distilled water, ultrasonically washed for 15 minutes, and after distilled water washing, it was ultrasonically washed in sequence with solvents such as isopropanol, acetone, and methanol, then dried at 120°C and sent to the evaporation machine.

[0365] On a prepared ITO-Ag-ITO substrate, a hole injection layer compound DNTPD / 40nm, a hole transport layer compound 235 / 100nm, a light-emitting layer (CBP:Ir(dpm)(piq)2 (98%:2% by mass)) / 25nm were deposited by vacuum evaporation layer by layer. Then, an electron transport layer compound Alq3 / 30nm, an electron injection layer LiF / 0.5nm, a cathode Mg-Ag (Mg:Ag doping ratio of 1:9 by mass) / 18nm were deposited, and then a capping layer material CP / 72nm was deposited on the cathode layer.

[0366]

[0367] Comparative Examples 2-16: In Comparative Example 1, the hole transport layer compound 235 was replaced with compounds 6, 49, 85, 133, 295, 14, 309, 1-362, 1-83, 1-73, 1-277, 1-338, 1-257, 1-366, and 1-1, while the other steps remained the same, resulting in Comparative Examples 2-16.

[0368] Comparative Example 17: The hole transport layer compound 235 in Comparative Example 1 was replaced with compound HT-1, and the other steps were the same, to obtain Comparative Example 17.

[0369] [Application Examples 1-32]

[0370] Application Example 1: Fabrication of organic light-emitting devices using vacuum thermal evaporation. The experimental steps were as follows: ITO-Ag-ITO substrate was washed three times in distilled water, ultrasonically washed for 15 minutes, and after distilled water washing, it was ultrasonically washed in sequence with solvents such as isopropanol, acetone, and methanol, then dried at 120°C and sent to the evaporation machine.

[0371] On a prepared ITO-Ag-ITO substrate, a hole injection layer compound DNTPD / 40nm, a first hole transport layer compound 6 / 60nm, a second hole transport layer compound 1-1 / 40nm, a light-emitting layer (CBP:Ir(dpm)(piq)2 (98%:2% mass ratio)) / 25nm, an electron transport layer compound Alq3 / 30nm, an electron injection layer LiF / 0.5nm, a cathode Mg-Ag (Mg:Ag doping ratio of 1:9 mass ratio) / 18nm, and then a capping layer material CP / 72nm are deposited on the cathode layer by vacuum evaporation.

[0372] Application Examples 2-32: Compounds 201, 49, 258, 242, 6, 295, 41, 280, 299, 36, 302, 85, 52, 134, 26, 14, 280, 133, 41, 49, 11, 275, 102, 133, 102, 235, 309, 242, 52, 6, and 36 of the present invention were used to replace compound 14 in Application Example 1, and compounds 1-3, 1-15, 1-44, 1-73, 1-83, and 1- of the present invention were used respectively. Compounds 147, 1-161, 1-205, 1-257, 1-263, 1-273, 1-277, 1-299, 1-308, 1-310, 1-312, 1-324, 1-338, 1-344, 1-347, 1-349, 1-352, 1-355, 1-359, 1-361, 1-362, 1-366, 1-367, 1-370, 1-362, and 1-83 were used to replace compound 1-1 in Application Example 1, and organic light-emitting devices were prepared according to the same preparation method as in Application Example 1. Application Examples 2-32.

[0373] 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 the McScience M6000 OLED lifetime testing system. The testing environment was atmospheric, at room temperature.

[0374] The luminescence characteristics of the obtained organic light-emitting devices are shown in Table 1. Table 1 shows the luminescence characteristics of the light-emitting devices prepared by the compounds prepared in the synthesis examples of this invention and the comparative substances.

[0375] [Table 1] Testing of the luminescent properties of light-emitting devices

[0376]

[0377]

[0378] Note: T95 refers to a current density of 10 mA / cm².2 Under certain conditions, the time it takes for the device brightness to decay to 95%.

[0379] As can be seen from the results in Table 1, the organic light-emitting device of the present invention exhibits advantages of high luminous efficiency and long lifespan compared with comparative examples 1-17, making it a high-performance organic light-emitting device. This is due to the specific combination of the first hole transport layer material and the specific second hole transport layer material of the present invention. The combined effect of these two materials enables the performance of the organic light-emitting device of the present invention to break through the limitations of conventional organic light-emitting devices, exhibiting advantages of high luminous efficiency and long lifespan.

[0380] 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 light-emitting device, comprising a substrate, an anode, an organic layer, and a cathode, characterized in that, The organic layer includes a hole transport region, which comprises a first hole transport layer and a second hole transport layer. The first hole transport layer contains a triarylamine derivative represented by Formula I, and the second hole transport layer contains a triamine compound represented by Formula II. In Formula I, the Ar is selected from one of the following groups: The R a The compound is selected from one or more of hydrogen, deuterium, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, adamantyl, and norbornel, wherein, when substituted with multiple substituents, the multiple substituents may be the same or different from each other; 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; 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, 8, or 9; a6 is 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; a7 is 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, or 13. Selected from one of the following groups: The R m R n R c R d It is independently selected from any one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted phenyl, and substituted or unsubstituted biphenyl; The value of m is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; when m is greater than 1, two or more R m They are the same or different from each other, or two adjacent R m The two rings are connected to form a benzene ring; The value of n is selected from 0, 1, 2, 3, 4, 5, 6, or 7; when n is greater than 1, two or more R n They are the same or different from each other, or two adjacent R n The two rings are connected to form a benzene ring; The value of c is selected from 0, 1, 2, or 3; when c is greater than 1, two or more R... c They are the same or different from each other, or two adjacent R c The two rings are connected to form a benzene ring; The d is selected from 0, 1, 2, 3, or 4; when d is greater than 1, two or more R d They are the same or different from each other, or two adjacent R d The two rings are connected to form a benzene ring; The L a L b L c Independently selected from single bonds or one of the following groups: In Formula II, at least one of Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 is selected from the groups shown in Formula 1-1 or Formula 1-2, and the others are independently selected from the groups shown in Formula 1-3: R4~R 11 The benzene ring is independently selected from one of hydrogen, deuterium, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted phenyl, or substituted or unsubstituted biphenyl, or two adjacent substituents bonded together to form a benzene ring, wherein R8, R9, and R1 in Formula 1-1 are... 10 R 11 There is one and only one carbon atom that serves as the connection site with L0; R0 may be selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, canyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, or two adjacent R0 may be bonded together to form the following cyclic structure: Wherein R 12 ~R 19 Independently selected from one of hydrogen, deuterium, methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, adamantyl, norbornel, canyl, phenyl, deuterated phenyl, tolyl, or R 12 ~R 19 A benzene ring is formed by the connection between two adjacent substituents; * indicates the connection site. Formulas 1-3 are selected from the following groups: R1, R2, and R3 are independently selected from one of hydrogen, deuterium, substituted or unsubstituted C1 to C6 alkyl groups; The L1, L2, L3, L4, L5, and L6 are independently selected from single bonds or one of the following groups: The term "substituted..." refers to mono- or poly-substituted groups independently selected from deuteryl, methyl, ethyl, isopropyl, and tert-butyl.

2. The organic light-emitting device according to claim 1, characterized in that, In formula I, Selected from one of the following groups:

3. The organic light-emitting device according to claim 1, characterized in that, The Ar is selected from one of the following groups: The R a The ingredient is selected from one or more of hydrogen, deuterium, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, adamantyl, and norbornel, wherein, when substituted with multiple substituents, the multiple substituents may be the same or different from each other, or adjacent substituents may be linked to form a ring; wherein R a It can also be R aa Replaced by, R aa It is selected from one or more of hydrogen, deuterium, and methyl, and when it is substituted by multiple substituents, the multiple substituents may be the same or different from each other.

4. The organic light-emitting device according to claim 1, characterized in that, The L a L b L c Independently selected from single bonds or one of the following groups:

5. The organic light-emitting device according to claim 1, characterized in that, In Equation 1-2 or Equation 1-2, R4~R 11 The phenyl group is independently selected from hydrogen, deuterium, methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, adamantyl, norbornel, cannyl, substituted or unsubstituted phenyl groups, wherein the substituents are selected from one or more substituents in the group consisting of deuterium, methyl, ethyl, isopropyl, and tert-butyl; wherein, in formulas 1-2, R8, R9, R 10 R 11 There is one and only one carbon atom that serves as the connection site with L0.

6. The organic light-emitting device according to claim 1, characterized in that, In Formulas 1-2, R0 is selected from one of methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, phenyl, naphthyl, biphenyl, deuterated phenyl, deuterated naphthyl, and deuterated biphenyl, or two adjacent R0 can be bonded together to form the following cyclic structure: Wherein R 12 ~R 19 It is independently selected from one of hydrogen, deuterium, methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butylphenyl, deuterated phenyl, and tolyl; * indicates a linking site.

7. The organic light-emitting device according to claim 1, characterized in that, Formulas 1-3 are selected from the following groups:

8. The organic light-emitting device according to claim 1, characterized in that, The L1, L2, L3, L4, L5, and L6 are independently selected from single bonds or one of the following groups:

9. The organic light-emitting device according to claim 1, characterized in that, R1, R2, and R3 are independently selected from one of hydrogen, deuterium, methyl, ethyl, isopropyl, and tert-butyl, or independently selected from the above groups substituted by one or more deuterium groups.

10. The organic light-emitting device according to claim 1, characterized in that, The triamine compound represented by Formula II is selected from any of the following chemical structures:

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