A carbazole compound and an organic electroluminescence device thereof

Abstract

The application provides a carbazole compound and an organic electroluminescent device thereof, and belongs to the technical field of organic electroluminescence. The carbazole compound provided by the application has a strong molecular structure, so that the material has high thermal stability and good film-forming property. In addition, the triplet energy level of the carbazole compound is high, and the energy level can be well matched with that of an adjacent layer. When the carbazole compound is used as a host material in an organic electroluminescent device, the luminous efficiency of the device can be greatly improved, and the service life of the device can be prolonged. The carbazole compound and the organic electroluminescent device thereof have good application effect and industrialization prospect.

Description

Technical Field

[0001] This invention relates to the field of organic electroluminescence technology, and more particularly to a carbazole compound and its organic electroluminescent device. Background Technology

[0002] Organic light-emitting diodes (OLEDs) are a type of device with a sandwich-like structure, consisting of an anode, a cathode, and organic layers in or around them. Currently, this technology is widely used in display panels for new lighting fixtures, smartphones, and tablets, and is gradually transitioning to large-size display products such as televisions. It is a rapidly developing and technologically demanding new display technology. OLEDs possess a series of advantages, including self-illumination, low-voltage DC drive, all-solid-state operation, wide viewing angle, and rich colors. Compared to liquid crystal displays (LCDs), OLEDs do not require a backlight, have a wider viewing angle, and lower power consumption, offering broader application prospects.

[0003] Since the first report of OLEDs, many scholars have been dedicated to studying how to improve the efficiency and lifetime of devices. Forrest and Thompson's research team discovered that transition metal complexes can be applied to Ph OLEDs (phosphorescent OLEDs). Phosphorescent materials have strong spin-orbit coupling and can utilize both singlet and triplet excitons simultaneously, theoretically achieving a quantum efficiency of 100% in phosphorescent photoluminescent devices. However, phosphorescent materials have long excited-state lifetimes, and when the triplet exciton concentration is high, triplet-triplet annihilation and triplet-polaron annihilation are prone to occur. Therefore, in practical applications, phosphorescent materials are often used as guest dopants in the host material to reduce the self-concentration quenching process. Thus, selecting a suitable host material in phosphorescent organic photoluminescent devices is also very important. The host material needs to have the following characteristics: (1) a high triplet energy level; (2) good carrier mobility and the ability to match the energy levels of adjacent layers; (3) high thermal stability and film formation stability. Currently, with the widespread commercial application of OLED displays and lighting, customers are increasingly demanding higher efficiency and longer lifespans from OLED devices. To meet these demands, in addition to continuously improving panel manufacturing processes, it is crucial to develop OLED materials that can meet higher device specifications. In particular, developing stable and efficient host materials to improve device luminous efficiency and extend device lifespan has significant practical application value. Summary of the Invention

[0004] In order to improve the luminous efficiency and extend the lifespan of devices, this invention provides a carbazole compound and its organic electroluminescent device. The carbazole compound has a high triplet energy level, good carrier mobility, and can match the energy level of adjacent organic layers. It also has high thermal stability and good film-forming properties. When applied to organic electroluminescent devices, it can effectively improve the luminous efficiency and extend the lifespan of the devices.

[0005] This invention provides a carbazole compound having the structure shown in Formula 1.

[0006]

[0007] The x, z, and v that are the same or different are selected from CH or N;

[0008] The Ra is selected from any one of hydrogen, deuterium, halogen, cyano, trifluoromethyl, C1-C12 alkyl, C3-C12 alicyclic, and C6-C30 aryl;

[0009] The Ra can be substituted by one or more substituents, wherein the substituents are selected from any one of deuterium, halogen, cyano, trifluoromethyl, C1-C12 alkyl, C3-C12 alicyclic, and C6-C30 aryl;

[0010] The Ar1 and Ar2 are the same or different and are selected from any one of substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C3-C12 alicyclic groups, and substituted or unsubstituted C6-C30 aryl groups;

[0011] The same or different R1 is selected from any one of hydrogen, deuterium, halogen, cyano, trifluoromethyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic group, and substituted or unsubstituted C6-C30 aryl group;

[0012] The a is selected from 1, 2, 3, 4, 5, 6, 7 or 8; when there are two or more R1s, the two or more R1s are the same or different from each other, or adjacent R1s are connected to each other to form substituted or unsubstituted rings;

[0013] The same or different R2 and R3 are selected from any one of hydrogen, deuterium, halogen, cyano, trifluoromethyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic group, and substituted or unsubstituted C6-C30 aryl group;

[0014] The b is selected from 1, 2, 3, 4, 5 or 6; when there are two or more R2s, the two or more R2s are the same or different from each other, or adjacent R2s are connected to each other to form substituted or unsubstituted rings;

[0015] The c is selected from 1, 2, 3, 4, 5, 6 or 7; when there are two or more R3s, the two or more R3s are the same or different from each other, or adjacent R3s are connected to each other to form substituted or unsubstituted rings;

[0016] L0, L1, and L2 are selected from any one of single bonds, substituted or unsubstituted C3-C12 alicyclic groups, and substituted or unsubstituted C6-C30 aryl groups;

[0017] Formula 1 contains at least one deuterium atom.

[0018] The present invention also provides an organic electroluminescent device comprising an anode, an organic layer, and a cathode, wherein the organic layer comprises one or a combination of at least two of the carbazole compounds.

[0019] The beneficial effects of this invention are:

[0020] The carbazole compounds provided by this invention have low vibrational coupling and strong molecular structural stability, thus exhibiting good thermal stability and film-forming properties. When used as the main material in organic electroluminescent devices, they can effectively extend the device's lifespan. Furthermore, the high triplet energy level of these carbazole compounds allows for better matching with adjacent organic layers, thereby significantly improving the device's luminous efficiency when applied to the device. Detailed Implementation

[0021] To make the objectives, technical solutions, and advantages of the embodiments of the present invention clearer, the technical solutions of the embodiments of the present invention will be clearly and completely described below in conjunction with the embodiments of the present invention. Obviously, the described embodiments are only some, not all, of the embodiments of the present invention. Furthermore, the embodiments and features in the embodiments of the present invention can be combined with each other without conflict. Based on the described embodiments of the present invention, all other embodiments obtained by those skilled in the art without creative effort are within the scope of protection of the present invention.

[0022] Unless otherwise defined, the technical or scientific terms used in this invention shall have the ordinary meaning as understood by one of ordinary skill in the art to which this invention pertains.

[0023] In the compounds of the present invention, any atom not specified as a particular isotope is included as any stable isotope of that atom, and includes atoms at both their natural and non-natural isotopic abundances.

[0024] In this specification, "*" indicates a portion connected to another substituent.

[0025] In this specification, when a substituent or linking site lies within a bond that extends through two or more rings, it indicates that the substituent or linking site can be linked to any one of the two or more rings, specifically to any one of the corresponding optional sites within the rings. For example, Can represent Can represent And so on.

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

[0027] For example, Can represent Can represent Can represent And so on.

[0028] In this specification, when a substituent or linking site is located on a bond that extends through two or more rings, it indicates that it can be linked to any one of the two or more rings, specifically to any one of the corresponding optional sites on the ring. For example Can represent And so on.

[0029] The halogens mentioned in this invention refer to fluorine, chlorine, bromine, and iodine;

[0030] The alkyl group described in this invention refers to a monovalent 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 25 carbon atoms, more preferably 1 to 12 carbon atoms, more preferably 1 to 10 carbon atoms, and particularly preferably 1 to 6 carbon atoms. Examples may include methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, etc., but are not limited thereto.

[0031] The alicyclic group mentioned in this invention refers to a monovalent group formed by removing one less hydrogen atom from an alicyclic hydrocarbon molecule. It can be cycloalkyl, cycloalkenyl, etc., preferably having 3 to 20 carbon atoms, more preferably 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, and most preferably 3 to 7 carbon atoms. Examples may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, etc., but are not limited thereto.

[0032] The aryl group described in this invention refers to a monovalent group formed by removing one hydrogen atom from the aromatic carbon atom of an aromatic hydrocarbon molecule. It can be a monocyclic aryl, polycyclic aryl, or fused-ring aryl, preferably having 6 to 30 carbon atoms, more preferably 6 to 18 carbon atoms, more preferably 6 to 14 carbon atoms, and most preferably 6 to 12 carbon atoms. Examples may include phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, indene, dihydroindene, dihydronaphthyl, tetrahydronaphthyl, anthracene, phenanthrene, pyrene, triphenylene, perylene, etc., but are not limited thereto.

[0033] The arylene group described in this invention refers to a divalent group formed by removing two hydrogen atoms from the aromatic carbon atom of an aromatic hydrocarbon molecule. Apart from being divalent groups, they are subject to the same description of aryl groups as described above.

[0034] The alicyclic group described in this invention refers to a divalent group formed by removing two hydrogen atoms from an alicyclic hydrocarbon molecule. Apart from being divalent groups, they are subject to the above description of alicyclic groups.

[0035] The term "substitution" as used in this invention refers to the replacement of hydrogen atoms in a compound group with other atoms or groups, and the substitution position is not limited.

[0036] In this invention, "substituted or unsubstituted" means either unsubstituted or substituted by one or more substituents selected from the group consisting of: protium, deuterium, tritium, cyano, halogen atom, amino, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C30 alicyclic group, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl group, substituted or unsubstituted C1-C25 heterocyclic alkanes and C6-C30 aromatic ring fused cycloyl group, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl group. The group may contain substituted or unsubstituted C6-C30 arylamine groups, substituted or unsubstituted C6-C30 aryloxy groups, preferably protium, deuterium, tritium, halogen atoms, cyano, C1-C12 alkyl, C3-C18 alicyclic, C6-C25 aryl, or C2-C25 heteroaryl. Specific examples may include protium, deuterium, tritium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, and n-propyl. alkyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, cyclopentenyl, cyclohexenyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocyclopentenyl, benzocyclohexenyl, phenyl, tolyl, mesitylene, pentadeuterated phenyl, biphenyl, naphthyl, anthracene, phenanthrene, benzophenanthrene, pyrene, triphenylene alkyl, peryl, fluoranyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, carbazole, 9-phenylcarbazole, spirodifluorenyl, carbazole-indole, pyrrole, furanyl, thiophene, indole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, oxadiazinyl The substituents include, but are not limited to, azole, thiazolyl, imidazole, benzoxazolyl, benzothiazolyl, benzotriazolyl, benzoimidazolyl, pyridinozolyl, pyridinozothiazolyl, pyridinozothiazolyl, pyrimidinozolyl, pyrimidinozothiazolyl, pyrimidinozolyl, quinolinyl, isoquinolinyl, quinolinozolyl, quinolinozothiazolyl, quinolinozolyl, phenothiazinyl, phenothiazinyl, acridineyl, etc. Alternatively, when there are two or more substituents, adjacent substituents may bond to form a ring; when there are two or more substituents, the two or more substituents may be the same as or different from each other.

[0037] The linking to form a substituted or unsubstituted ring, as described in this invention, refers to two groups linked together by chemical bonds and optionally aromatized. Examples are shown below:

[0038]

[0039] In this invention, the ring formed by the connection can be a five-membered ring, a six-membered ring, or a fused ring. Examples may include benzene, pyridine, pyrimidine, naphthalene, fluorene, cyclopentene, cyclohexene, cyclopentane, cyclohexane, cyclohexane, benzobenzene, quinoline, isoquinoline, dibenzothiophene, phenanthrene, or pyrene, but are not limited thereto.

[0040] The following description refers to embodiments of the organic electroluminescent device of the present invention. However, the embodiments of the present invention can be modified into other forms, and the scope of the present invention is not limited to the embodiments described below.

[0041] In this invention, "containing at least one deuterium" means containing one, two, three, four, five, six, seven, eight, nine, ten or more deuteriums.

[0042] In this invention, "at least one is deuterium" means one, two, three, four, five, six, seven, eight, nine, ten or more are deuterium.

[0043] In describing the structural elements of this invention, the terms "comprising" or "including" as used herein mean that the device or object preceding the term covers the device or object listed after the term and its equivalents, without excluding other devices or objects. Terms such as "connected" or "linked" are not limited to physical or mechanical connections, but can include electrical connections, whether direct or indirect. Terms such as "inner," "outer," "upper," and "lower" are used only to indicate relative positional relationships; when the absolute position of the described structural element changes, the relative positional relationship may also change accordingly. Furthermore, when a structural element such as a layer, membrane, region, or plate is located "on" other structural elements, it can be understood not only as being "directly above" other structural elements, but also as having other structural elements in between. Conversely, when a structural element is located "directly above" other structural elements, it should be understood as having no other structural elements in between.

[0044] This invention provides a carbazole compound having the structure shown in Formula 1.

[0045]

[0046] The x, z, and v that are the same or different are selected from CH or N;

[0047] The Ra is selected from any one of hydrogen, deuterium, halogen, cyano, trifluoromethyl, C1-C12 alkyl, C3-C12 alicyclic, and C6-C30 aryl;

[0048] The Ra can be substituted by one or more substituents, wherein the substituents are selected from any one of deuterium, halogen, cyano, trifluoromethyl, C1-C12 alkyl, C3-C12 alicyclic, and C6-C30 aryl;

[0049] The Ar1 and Ar2 are the same or different and are selected from any one of substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C3-C12 alicyclic groups, and substituted or unsubstituted C6-C30 aryl groups;

[0050] The same or different R1 is selected from any one of hydrogen, deuterium, halogen, cyano, trifluoromethyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic group, and substituted or unsubstituted C6-C30 aryl group;

[0051] The a is selected from 1, 2, 3, 4, 5, 6, 7 or 8; when there are two or more R1s, the two or more R1s are the same or different from each other, or adjacent R1s are connected to each other to form substituted or unsubstituted rings;

[0052] The same or different R2 and R3 are selected from any one of hydrogen, deuterium, halogen, cyano, trifluoromethyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic group, and substituted or unsubstituted C6-C30 aryl group;

[0053] The b is selected from 1, 2, 3, 4, 5 or 6; when there are two or more R2s, the two or more R2s are the same or different from each other, or adjacent R2s are connected to each other to form substituted or unsubstituted rings;

[0054] The c is selected from 1, 2, 3, 4, 5, 6 or 7; when there are two or more R3s, the two or more R3s are the same or different from each other, or adjacent R3s are connected to each other to form substituted or unsubstituted rings;

[0055] L0, L1, and L2 are selected from any one of single bonds, substituted or unsubstituted C3-C12 alicyclic groups, and substituted or unsubstituted C6-C30 aryl groups;

[0056] Formula 1 contains at least one deuterium atom.

[0057] Preferably, the carbazole compound has a structure as shown in Formula 1-1 or Formula 1-2.

[0058]

[0059] Preferably, in the structures shown in Formula I, Formula 1-1 and Formula 1-2, at most four of the eight x are selected from N, more preferably at most two are selected from N; at most two of the four x in each ring are selected from N, more preferably at most one is selected from N.

[0060] Preferably, in the structures shown in Formula I, Formula 1-1 and Formula 1-2, at most four of the eight z are selected from N, more preferably at most two are selected from N; at most two of the four z in each ring are selected from N, more preferably at most one is selected from N.

[0061] Preferably, in the structures shown in Formula I, Formula 1-1 and Formula 1-2, at most four of the eight v are selected from N, more preferably at most two are selected from N; at most two of the four v in each ring are selected from N, more preferably at most one is selected from N.

[0062] Preferably, R2 and R3, whether identical or different, are selected from any one of hydrogen, deuterium, halogen, cyano, methyl, deuterated methyl, ethyl, deuterated ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, cyclobutyl, deuterated cyclobutyl, cyclopentyl, deuterated cyclopentyl, cyclohexyl, deuterated cyclohexyl, adamantyl, deuterated adamantyl, norbornyl, deuterated norbornyl, cyclopentenyl, deuterated cyclopentenyl, cyclohexenyl, deuterated cyclohexenyl, phenyl, deuterated phenyl, cyanophenyl, pentafluorophenyl, pentamethylphenyl, biphenyl, deuterated biphenyl, terphenyl, naphthyl, and deuterated naphthyl.

[0063] The b is selected from 1, 2, 3, 4, 5 or 6; when there are two or more R2s, the two or more R2s are the same or different from each other, or adjacent R2s are connected to each other to form substituted or unsubstituted rings;

[0064] The c is selected from 1, 2, 3, 4, 5, 6 or 7; when there are two or more R3s, the two or more R3s are the same or different from each other, or adjacent R3s are connected to each other to form substituted or unsubstituted rings.

[0065] Preferably, the Choose any one of the structures shown below.

[0066]

[0067]

[0068] The Ra is selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted cyclopentenyl, substituted or unsubstituted cyclohexenyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinyl, substituted or unsubstituted phenanthrene, substituted or unsubstituted triphenylene, and substituted or unsubstituted fluorenyl.

[0069] The Ra can be substituted with one or more substituents selected from deuterium, halogen, cyano, methyl, ethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, fluorenyl, deuterated methyl, deuterated isopropyl, deuterated tert-butyl, deuterated phenyl, deuterated biphenyl, deuterated naphthyl, trifluoromethyl, and trifluorotolyl. When two or more substituents are present, the two or more substituents may be the same as or different from each other.

[0070] Preferred, Selected from those structures containing deuterium as shown above.

[0071] Preferably, Ar1 and Ar2, whether identical or different, are selected from any of the structures shown below.

[0072] *-CH3 *-CD3

[0073] The Rb and Rc that are the same or different are selected from any one of hydrogen, deuterium, halogen, cyano, trifluoromethyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic group, and substituted or unsubstituted C6-C30 aryl.

[0074] The same or different R4 is selected from any one of hydrogen, deuterium, halogen, cyano, trifluoromethyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C25 silyl.

[0075] The m1 is selected from 1, 2, 3, 4, 5, 6 or 7; the m2 is selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9; the m3 is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; the m4 is selected from 1, 2, 3, 4 or 5; the m5 is selected from 1, 2, 3 or 4; the m6 is selected from 1, 2, 3, 4, 5, 6, 7 or 8; when there are two or more R4s, the two or more R4s are the same or different from each other, or two adjacent R4s are connected to each other to form a substituted or unsubstituted ring.

[0076] Preferably, Ar1 and Ar2, whether identical or different, are selected from any of the structures shown below.

[0077] *-CH3 *-CD3

[0078]

[0079]

[0080] The Rb and Rc that are the same or different are selected from any one of hydrogen, deuterium, halogen, cyano, trifluoromethyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted cyclopentenyl, substituted or unsubstituted cyclohexenyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, and substituted or unsubstituted naphthyl.

[0081] The Rb and Rc may be substituted by one or more substituents, wherein the substituents are selected from any one or a combination of at least two of the following: deuterium, halogen, cyano, methyl, ethyl, isopropyl, tert-butyl, adamantyl, norbornel, phenyl, biphenyl, naphthyl, deuterated methyl, deuterated isopropyl, deuterated tert-butyl, deuterated phenyl, deuterated biphenyl, deuterated naphthyl, trifluoromethyl, and trifluorotolyl. When two or more substituents are present, the two or more substituents may be the same as or different from each other.

[0082] Preferably, Ar1 and Ar2, whether identical or different, are selected from any of the structures shown below.

[0083] *-CD3

[0084]

[0085]

[0086] The Rb and Rc that are the same or different are selected from any one of hydrogen, deuterium, halogen, cyano, trifluoromethyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, and substituted or unsubstituted naphthyl.

[0087] The Rb and Rc may be substituted by one or more substituents, wherein the substituents are selected from any one or a combination of at least two of the following: deuterium, halogen, cyano, methyl, ethyl, isopropyl, tert-butyl, adamantyl, norbornel, phenyl, biphenyl, naphthyl, deuterated methyl, deuterated isopropyl, deuterated tert-butyl, deuterated phenyl, deuterated biphenyl, deuterated naphthyl, trifluoromethyl, and trifluorotolyl. When two or more substituents are present, the two or more substituents may be the same as or different from each other.

[0088] Preferably, the Ar1 and Ar2, whether identical or different, are selected from those containing deuterium in the structures shown above.

[0089] Preferably, L0, L1, and L2, whether identical or different, are selected from single bonds or any of the structures shown below.

[0090]

[0091] The same or different Re, Rf, and Rg are selected from any one of hydrogen, deuterium, halogen, cyano, trifluoromethyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic group, and substituted or unsubstituted C6-C30 aryl group;

[0092] The R5 is any one of the following: hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic group, or substituted or unsubstituted C6-C18 aryl group, which may be the same as or different from the R5.

[0093] The n1 that is the same or different is selected from 1, 2, 3 or 4; the n2 that is the same or different is selected from 1, 2, 3, 4, 5 or 6; the n3 that is the same or different is selected from 1, 2, 3, 4, 5, 6, 7 or 8; the n4 that is the same or different is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; the n5 that is the same or different is selected from 1, 2, 3, 4, 5, 6 or 7; when there are two or more R5s, the two or more R5s are the same or different from each other, or adjacent R5s are connected to each other to form substituted or unsubstituted rings.

[0094] Preferably, L0, L1, and L2, whether identical or different, are selected from single bonds or any of the structures shown below.

[0095]

[0096] The same or different Re, Rf, and Rg are selected from any one of hydrogen, deuterium, halogen, cyano, trifluoromethyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted cyclopentenyl, substituted or unsubstituted cyclohexenyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, and substituted or unsubstituted naphthyl.

[0097] The Re, Rf, and Rg may be substituted by one or more substituents, wherein the substituents are selected from any one or a combination of at least two of the following: deuterium, halogen, cyano, methyl, ethyl, isopropyl, tert-butyl, adamantyl, norbornel, phenyl, biphenyl, naphthyl, deuterated methyl, deuterated isopropyl, deuterated tert-butyl, deuterated phenyl, deuterated biphenyl, deuterated naphthyl, trifluoromethyl, and trifluorotolyl. When two or more substituents are present, the two or more substituents may be the same as or different from each other.

[0098] Preferably, L0, L1, and L2, whether the same or different, are selected from single bonds or those containing deuterium in the structures shown above.

[0099] Preferably, L1 contains at least one deuterium.

[0100] Preferably, L2 contains at least one deuterium.

[0101] Preferably, the Ar1 contains at least one deuterium.

[0102] Preferably, the Ar2 contains at least one deuterium.

[0103] Preferably, the “*-L1-Ar1” contains at least one deuterium.

[0104] Preferably, the “*-L2-Ar2” contains at least one deuterium.

[0105] Preferably, at least one of “*-L1-Ar1” and “*-L2-Ar2” contains deuterium.

[0106] Preferably, R1 contains at least one deuterium. More preferably, at least one of R1 is deuterium.

[0107] Preferably, R2 contains at least one deuterium. More preferably, at least one of R2 is deuterium.

[0108] Preferably, R3 contains at least one deuterium. More preferably, at least one of R3 is deuterium.

[0109] Preferably, at least one of R2 and R3 contains deuterium. More preferably, at least one of R2 and R3 is deuterium. Preferably, the carbazole compound of the present invention is selected from any one of the structures shown below.

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133] This invention also provides a method for preparing carbazole compounds.

[0134]

[0135]

[0136] The Xa that is the same or different is selected from any one of I, Br, and Cl;

[0137] The above-mentioned substituents can be bonded by methods known in the art, and the type and position or number of substituents can be changed according to techniques known in the art.

[0138] The present invention provides an organic electroluminescent device, comprising an anode, an organic layer, and a cathode, wherein the organic layer comprises one or a combination of at least two of the carbazole compounds described in the present invention.

[0139] Preferably, the organic layer of the present invention includes a light-emitting layer, which contains one or a combination of at least two of the carbazole compounds of the present invention.

[0140] The organic layer described in this invention may further include a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, an electron injection layer, an electron transport layer, a hole blocking layer, a capping layer, an encapsulation layer, etc. However, the structure of the organic electroluminescent device of this invention is not limited to the above structure. If necessary, multiple organic layers can be omitted or simultaneously included, and organic layers with the same function can be made into a stacked structure of two or more layers.

[0141] The organic electroluminescent device of the present invention preferably has the following structure:

[0142] Substrate / Anode / Hole injection layer / Hole transport layer / Light-emitting layer / Electron transport layer / Electron injection layer / Cathode;

[0143] Substrate / Anode / Hole injection layer / Hole transport layer / Light emission layer / Electron transport layer / Electron injection layer / Cathode / Capping layer;

[0144] Substrate / Anode / Hole injection layer / Hole transport layer / Light emission layer / Hole blocking layer / Electron transport layer / Electron injection layer / Cathode;

[0145] Substrate / Anode / Hole injection layer / Hole transport layer / Light emission layer / Hole blocking layer / Electron transport layer / Electron injection layer / Cathode / Capping layer;

[0146] Substrate / Anode / Hole injection layer / Hole transport layer / Electron blocking layer / Light emitting layer / Hole blocking layer / Electron transport layer / Electron injection layer / Cathode;

[0147] Substrate / Anode / Hole injection layer / Hole transport layer / Electron blocking layer / Light emitting layer / Hole blocking layer / Electron transport layer / Electron injection layer / Cathode / Capping layer;

[0148] Substrate / Anode / Hole injection layer / Hole transport layer / Light emission auxiliary layer / Light emission layer / Hole blocking layer / Electron transport layer / Electron injection layer / Cathode;

[0149] Substrate / Anode / Hole injection layer / Hole transport layer / Light emission auxiliary layer / Light emission layer / Hole blocking layer / Electron transport layer / Electron injection layer / Cathode / Capping layer;

[0150] However, the structure of organic electroluminescent devices is not limited to this. The organic electroluminescent devices described in this invention can be selected and combined according to device parameter requirements and material properties. Some organic layers can be added or omitted, and organic layers with the same function can be made into a stacked structure of two or more layers.

[0151] The organic electroluminescent device of the present invention is typically formed on a substrate. The substrate can be any material that remains unchanged when forming electrodes or organic layers, such as glass, plastic, polymer films, silicon, etc.

[0152] In the organic electroluminescent device of the present invention, the anode material is preferably a high work function material that can promote hole injection into the organic layer. Specific examples of anode materials that can be used in the present invention may include: metals, such as vanadium, chromium, copper, zinc and gold, or alloys thereof; metal oxides, such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); combinations of metals and oxides, such as ITO-Ag-ITO; conductive polymers, such as poly(3-methylthiophene), polypyrrole, polyaniline, poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), etc., but are not limited thereto.

[0153] In the organic electroluminescent device of the present invention, the hole injection material is preferably a material with good hole-accepting ability. Specific examples of hole injection materials that can be used in the present invention may include: metal oxides such as silver oxide, vanadium oxide, tungsten oxide, copper oxide, and titanium oxide; phthalocyanine compounds; benzidine compounds; phenazine compounds; etc., such as copper phthalocyanine (CuPc), titanium phthalocyanine, N,N'-diphenyl-N,N'-di-[4-(N,N-diphenylamine)phenyl]benzidine (NPNPB), N,N,N',N'-tetra(4-methoxyphenyl)benzidine... Aniline (MeO-TPD), diquinoxolino[2,3-a:2',3'-c]phenazine (HATNA), 4,4',4”-tris[2-naphthylphenylamino]triphenylamine (2T-NATA), 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazabenzophenanthrene (HAT-CN), 4,4',4”-tris(N,N-diphenylamino)triphenylamine (TDATA), etc., but not limited to these.

[0154] In the organic electroluminescent device of the present invention, the hole transport material is preferably a material with excellent hole transport performance and a HOMO energy level that matches the corresponding anode material. Specific examples of hole transport materials that can be used in this invention may include diphenylamine compounds, triphenylamine compounds, fluorene compounds, and carbazole compounds, such as N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), N,N'-di(naphthyl-1-yl)-N,N'-di(phenyl)-2,2'-dimethylbenzidine (α-NPD), N,N'-diphenyl-N,N'-di(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), 4-[1-[4-[di(4-methylphenyl)amino]phenyl]cyclohexyl]-N-(3-methylphenyl)-N-(4-methylphenyl)aniline (TAPC), etc., but are not limited thereto.

[0155] In the organic electroluminescent device of the present invention, the light-emitting auxiliary layer is preferably made of a material with good hole transport performance and electron blocking performance. Specific examples of luminescent auxiliary materials that can be used in this invention may include materials such as triarylamine derivatives, spirofluorene derivatives, and furan derivatives, such as TPD, NPB, N4,N4-bis([1,1'-biphenyl]-4-yl)-N4'-phenylN4'-[1,1':4',1”-terphenyl]-4-yl-[1,1'-biphenyl]-4,4'-diamine, N-([1,1'-diphenyl]-4-yl)-N-(9,9-dimethyl-9H-furan-2-yl)-9,9'-spirodifluorene-2-amine, N,N-bis([1,1'-biphenyl]-4-yl)-3'-(dibenzo[b,d]furan-4-yl)-[1,1'-biphenyl]-4-amine, etc., but are not limited thereto.

[0156] In the organic electroluminescent device of the present invention, the light-emitting layer material includes a host material and a dopant 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), 4,4',4”-tris(carbazole-9-yl)triphenylamine (TCTA), 9,10-bis(1-naphthyl)anthracene (α-ADN), N,N'-bis-(1-naphthyl)-N,N '-Diphenyl-[1,1':4',1”:4”,1”'-tetraphenyl]-4,4”'-diamino (4PNPB), 1,3,5-tris(9-carbazole)benzene (TCP), etc., but not limited thereto. Preferably, the main material of the light-emitting layer of the present invention is selected from 9,10-bis(2-naphthyl)anthracene (ADN), 9,9'-(1,3-phenyl)bis-9H-carbazole (mCP), 4,4',4”-tris(carbazole-9-yl)triphenylamine (TCTA), 9,10-bis(1-naphthyl)anthracene (α-AND), carbazole compounds of the present invention, etc. The doping material of the light-emitting layer can be selected from (6-(4-(diphenylamino(phenyl)-N,N-diphenylpyrene-1-amine)(DPAP-DPPA), 2,5,8,11-tetra-tert-butylperylene (TBPe), 4,4'-bis[4-(diphenylamino)styryl]biphenyl (BDAVBi), 4,4'-bis[4-(di-p-tolylamino)styryl]biphenyl (DPAVBi), bis(2-hydroxyphenylpyridine)beryllium (Bepp2), bis(4,6-difluorophenylpyridine-C2,N)pyridinecarboxyiridium (FIrpic), tris(2-phenylpyridine)iridium (Ir(ppy)3), bis(2-phenylpyridine)iridium acetylacetonate (Ir(ppy)2(acac)), 9,10-bis[N-(p-tolyl)aniline] Anthracene (TPA), 4-(dicyanomethylene)-2-methyl-6-(4-dimethylaminostyryl)-4H-pyran (DCM), tris[1-phenylisoquinoline-C2,N]iridium(III)(Ir(piq)3), bis(1-phenylisoquinoline)(acetylacetone)iridium (Ir(piq)2(acac)), etc., but not limited thereto. Preferably, the luminescent layer guest of the present invention is selected from 4,4'-bis[4-(di-p-tolylamino)styryl]biphenyl (DPAVBi), 2,5,8,11-tetra-tert-butylperylene (TBPe), 9,10-bis[N-(p-tolyl)aniline]anthracene (TPA), 4-(dicyanomethylene)-2-methyl-6-(4-dimethylaminostyryl)-4H-pyran (DCM), etc.

[0157] The optimal doping ratio of the light-emitting layer host material and the light-emitting layer dopant material varies depending on the material used. Typically, the doping ratio of the light-emitting layer dopant material is 0.01% to 20%, preferably 0.1% to 15%, and more preferably 1% to 10%.

[0158] In the organic electroluminescent device of the present invention, the hole blocking material has strong hole blocking ability and suitable HOMO and LUMO energy levels. Specific examples of hole blocking materials that can be used in the present invention may include imidazole, triazole, phenanthroline derivatives, etc., such as 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene (TPBi), 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), bis(2-methyl-8-hydroxyquinoline)(4-phenylphenol)aluminum(III) (BAlq), etc., but are not limited thereto.

[0159] In the organic electroluminescent device of the present invention, the electron transport material is preferably a material with strong electron-withdrawing ability and low HOMO and LUMO energy levels. Specific examples of electron transport materials that can be used in the present invention may include imidazole, triazole, phenanthroline derivatives, quinoline, etc., such as 2,9-(dimethyl)-4,7-biphenyl-1,10-o-phenanthroline (BCP), 1,3,5-tris[(3-pyridyl)-phenyl]benzene (TmPyPB), 4,4'-diphenyl... (4,6-Diphenyl-1,3,5-triazinyl)biphenyl (BTB), 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene (TPBi), 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), 2-(naphthyl-2-yl)-4,7-(diphenyl)-1,10-o-phenanthroline (HNBphen), 8-hydroxyquinoline-lithium, etc. (LiQ), etc., but not limited to these.

[0160] In the organic electroluminescent device of the present invention, the electron injection material is preferably a material with a small potential barrier difference between itself and the adjacent organic transport material or host material, and simultaneously has the effect of injecting electrons from the cathode. Examples of electron injection materials that can be used in the present invention include, but are not limited to, alkali metal salts (such as LiF, CsF), alkaline earth metal salts (such as MgF2), and metal oxides (such as Al2O3, MoO3).

[0161] In the organic electroluminescent device of the present invention, the cathode material is preferably a low work function material that can promote electron injection into the organic layer. Specific examples of cathode materials that can be used in the present invention may include: metals such as aluminum, magnesium, silver, indium, tin, titanium, and their alloys; multilayer metal materials such as LiF / Al, Mg / Ag, Li / Al, LiO2 / Al, BaF2 / Al, etc., but are not limited thereto.

[0162] In the organic electroluminescent device of the present invention, the capping layer material is preferably a material that improves optical coupling. Specific examples of capping layer materials that can be used in the present invention may include arylamine derivatives, carbazole derivatives, benzimidazole derivatives, triazole derivatives, lithium fluoride, etc., but are not limited thereto. The capping layer can be formed simultaneously on the outside of the anode and the outside of the cathode, or it can be disposed on the outside of the anode or the outside of the cathode. Preferably, the capping layer of the present invention is disposed on the outside of the cathode.

[0163] The present invention does not impose any special restrictions on the thickness of each organic layer of the organic electroluminescent device; thicknesses commonly used in the field can be adopted.

[0164] The organic electroluminescent device of the present invention can be made using any one of the following methods: vacuum evaporation, spin coating, vapor deposition, blade coating, laser thermal transfer, electrospray coating, slot coating, and dip coating. In the present invention, vacuum evaporation is preferred.

[0165] The organic electroluminescent 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.

[0166] 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.

[0167] Preparation and characterization of compounds

[0168] Description of raw materials, reagents, and characterization equipment:

[0169] The present invention does not impose any particular restrictions on the source of raw materials and reagents used in the following embodiments, which can be commercially available products or prepared by methods known to those skilled in the art.

[0170] Mass spectrometry was performed using a Waters G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer, with chloroform as the solvent.

[0171] 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.

[0172] Synthesis Examples

[0173] [Synthetic Example 1] Synthesis of Intermediate 6-d

[0174]

[0175] 6-A (10.55 g, 50.00 mmol) was dissolved in NMP (500 ml), and 6-B (8.43 g, 52.00 mmol), sodium sulfate (7.10 g, 50 mmol), potassium carbonate (6.91 g, 50 mmol), and copper (0.96 g, 15 mmol) were added. The mixture was heated to 200 °C and reacted for 18 hours. After the reaction was completed, the solvent was removed by vacuum distillation, and the mixture was extracted with dichloromethane and water. The organic phase was dried over anhydrous magnesium sulfate and then purified by vacuum distillation, column chromatography, and recrystallization to obtain intermediate 6-d (12.12 g, yield 83%) with HPLC purity ≥99.85% and mass spectrometry m / z: 292.1458 (theoretical value: 292.1431).

[0176] [Synthetic Example 2] Synthesis of Intermediate 9-d

[0177]

[0178] Following the preparation method of Synthesis Example 1, 6-A and 6-B were replaced with equimolar amounts of 9-A and 9-B, respectively, to obtain intermediate 9-d (12.19 g), with an HPLC purity ≥99.76%. Mass spectrometry m / z: 290.1318 (theoretical value: 290.1306).

[0179] [Synthetic Example 3] Synthesis of Intermediate 14-d

[0180]

[0181] Following the preparation method of Synthesis Example 1, 6-A was replaced with an equimolar amount of 14-A to obtain intermediate 14-d (12.92 g), with an HPLC purity ≥99.58%. Mass spectrometry m / z: 315.2197 (theoretical value: 315.2184).

[0182] [Synthetic Example 4] Synthesis of Intermediate 33-d

[0183]

[0184] Following the preparation method of Synthesis Example 1, 6-A was replaced with an equimolar amount of 33-A to obtain intermediate 33-d (13.08 g), with an HPLC purity ≥99.81%. Mass spectrometry m / z: 315.2168 (theoretical value: 315.2184).

[0185] [Synthetic Example 5] Synthesis of Intermediate 45-d

[0186]

[0187] Following the preparation method of Synthesis Example 1, 6-A and 6-B were replaced with equimolar amounts of 33-A and 9-B, respectively, to obtain intermediate 45-d (12.36 g), with an HPLC purity ≥99.75%. Mass spectrometry m / z: 294.1569 (theoretical value: 294.1557).

[0188] [Synthetic Example 6] Synthesis of Intermediate 51-d

[0189]

[0190] Following the preparation method of Synthesis Example 1, 6-A and 6-B were replaced with equimolar amounts of 51-A and 51-B, respectively, to obtain intermediate 51-d (15.08 g), with an HPLC purity ≥99.60%. Mass spectrometry m / z: 377.0629 (theoretical value: 377.0647).

[0191] [Synthetic Example 7] Synthesis of Intermediate 105-d

[0192]

[0193] Following the preparation method of Synthesis Example 1, 6-A and 6-B were replaced with equimolar amounts of 105-A and 9-B, respectively, to obtain intermediate 105-d (12.06 g), with an HPLC purity ≥99.48%. Mass spectrometry m / z: 294.1573 (theoretical value: 294.1557).

[0194] [Synthetic Example 8] Synthesis of Intermediate 178-d

[0195]

[0196] Following the preparation method of Synthesis Example 1, 6-A and 6-B were replaced with equimolar amounts of 178-A and 178-B, respectively, to obtain intermediate 178-d (13.60 g), with an HPLC purity ≥99.78%. Mass spectrometry m / z: 344.1702 (theoretical value: 344.1713).

[0197] [Synthetic Example 9] Synthesis of Intermediate 201-d

[0198]

[0199] Following the preparation method of Synthesis Example 1, 6-A was replaced with an equimolar amount of 201-A to obtain intermediate 201-d (13.86 g), with an HPLC purity ≥99.87%. Mass spectrometry m / z: 342.1599 (theoretical value: 342.1588).

[0200] [Synthetic Example 10] Synthesis of Intermediate 206-d

[0201]

[0202] Synthesis of intermediate 33-d

[0203] 33-A (23.41 g, 100.00 mmol) was dissolved in NMP (1000 ml), and 6-B (17.01 g, 105.00 mmol), sodium sulfate (14.20 g, 100 mmol), potassium carbonate (13.82 g, 100 mmol), and copper (1.92 g, 130 mmol) were added. The mixture was heated to 200 °C and reacted for 18 hours. After the reaction was completed, the solvent was removed by vacuum distillation, followed by extraction with dichloromethane and water. The organic phase was dried over anhydrous magnesium sulfate, then purified by vacuum distillation, column chromatography, and recrystallization to obtain intermediate 33-d (26.17 g, yield 83%) with an HPLC purity ≥99.81%. Mass spectrometry m / z: 315.2168 (theoretical value: 315.2184).

[0204] Synthesis of intermediate 206-E

[0205] Under nitrogen protection, 33-D (25.85 g, 82.00 mmol), 206-D (18.52 g, 80 mmol), tetrakis(triphenylphosphine)palladium (1.85 g, 1.60 mmol), potassium carbonate (22.11 g, 160.00 mmol), toluene (300 mL), and ethanol (100 mL) were added to a reaction flask. The mixture was stirred and refluxed for 6.5 hours. After the reaction was complete and cooled to room temperature, the filter cake was obtained by suction filtration and washed with ethanol. Finally, the filter cake was recrystallized from toluene / ethanol at a ratio of 5:1 to obtain intermediate 206-E (23.06 g, 71%); HPLC purity ≥99.63%. Mass spectrometry m / z: 405.2049 (theoretical value: 405.2037).

[0206] Synthesis of intermediate 206-d

[0207] Under nitrogen protection, 206-E (20.30 g, 50.00 mmol), pinacol diborate (13.20 g, 52.00 mmol), potassium acetate (9.81 g, 100.00 mmol), 1,1'-bis(diphenylphosphine)ferrocene palladium dichloride (0.73 g, 1.00 mmol), and 1,4-dioxane (200 mL) were added to a reaction flask. The mixture was stirred and refluxed for 5 hours. After the reaction was complete and cooled to room temperature, the filter cake was obtained by suction filtration and washed with ethanol. Finally, the filter cake was recrystallized from toluene to give intermediate 206-d (17.91 g, 72%); HPLC purity ≥99.88%. Mass spectrometry m / z: 497.3262 (theoretical value: 497.3279).

[0208] [Synthetic Example 11] Synthesis of Intermediate 217-d

[0209]

[0210] Following the preparation method of Synthesis Example 10, 33-A and 206-D were replaced with equimolar amounts of 6-A and 217-D, respectively, to obtain intermediate 217-d (16.44 g), with an HPLC purity ≥99.64%. Mass spectrometry m / z: 450.2539 (theoretical value: 450.2527).

[0211] [Synthetic Example 12] Synthesis of Intermediate 244-d

[0212]

[0213] Following the preparation method of Synthesis Example 10, 33-A, 6-B, and 206-D were replaced with equimolar amounts of 6-A, 244-B, and 244-D, respectively, to obtain intermediate 244-d (22.35 g), with an HPLC purity ≥99.49%. Mass spectrometry m / z: 629.3449 (theoretical value: 629.3465).

[0214] [Synthetic Example 13] Synthesis of Intermediate 311-d

[0215]

[0216] Following the preparation method of Synthesis Example 10, 33-d and 206-D were replaced with equimolar amounts of 311-C and 217-D, respectively, to obtain intermediate 311-d (17.84 g), with an HPLC purity ≥99.85%. Mass spectrometry m / z: 495.2388 (theoretical value: 495.2370).

[0217] [Synthetic Example 14] Synthesis of Intermediate 364-d

[0218]

[0219] Synthesis of intermediate 364-I

[0220] Under nitrogen protection, 364-G (28.99 g, 100.00 mmol), tetrahydrofuran (450 mL), and n-butyllithium (55 mL of 1.6 M hexane solution) were added to a reaction flask and stirred at -78 °C for 1 hour. Then, a tetrahydrofuran solution (150 mL) containing 364-H (25.83 g, 100 mmol) was added dropwise to the reaction flask, and the reaction was continued at -78 °C for 1 hour, followed by stirring at room temperature for 4 hours. After the reaction was complete, a saturated ammonium chloride solution was added to separate the organic layer, and the organic layer was concentrated. The concentrated organic solid, acetic anhydride (800 mL), and hydrochloric acid (40 mL) were added to a reaction flask and stirred at 100 °C for 4 hours. After the reaction was completed, cold water (350 mL) was added to precipitate the solid product, which was then filtered. The product was then purified by silica gel column chromatography (petroleum ether / dichloromethane = 9:1) to obtain intermediate 364-I (34.75 g, yield 77%) with HPLC purity ≥99.61% and mass spectrometry m / z: 451.1730 (theoretical value: 451.1744).

[0221] Synthesis of intermediate 364-d

[0222] Under nitrogen protection, intermediate 364-I (24.82 g, 55 mmol), toluene (300 mL), 6-B (8.1 g, 50 mmol), tris(benzylacetone)palladium (0.46 g, 0.50 mmol), 1,1'-binaphthyl-2,2'-bis(diphenylphosphine) (1.00 g, 1.6 mmol), and sodium tert-butoxide (15.36 g, 160 mmol) were added to a reaction flask, stirred to dissolve, and refluxed for 8 hours. After the reaction was complete, the mixture was cooled to room temperature, filtered, and the organic solvent was removed by vacuum distillation. The obtained solid was recrystallized from methanol to give intermediate 364-d (21.03 g, yield 79%) with an HPLC purity ≥99.74%. Mass spectrometry m / z: 532.2385 (theoretical value: 532.2370).

[0223] [Synthetic Example 15] Synthesis of Intermediate 376-d

[0224]

[0225] Following the preparation method of Synthesis Example 14, 364-H and 6-B were replaced with equimolar amounts of 376-H and 376-J, respectively, to obtain intermediate 376-d (23.20 g), with an HPLC purity ≥99.64%. Mass spectrometry m / z: 602.3141 (theoretical value: 602.3153).

[0226] [Synthetic Example 16] Synthesis of Intermediate 382-d

[0227]

[0228] Following the preparation method of Synthesis Example 1, 6-B was replaced with an equimolar amount of 382-B to obtain intermediate 382-d (18.07 g), with an HPLC purity ≥99.75%. Mass spectrometry m / z: 463.1732 (theoretical value: 463.1744).

[0229] [Synthetic Example 17] Synthesis of Intermediate 391-d

[0230]

[0231] Following the preparation method of Synthesis Example 1, 6-B was replaced with an equimolar amount of 391-B to obtain intermediate 391-d (14.38 g), with an HPLC purity ≥99.45%. Mass spectrometry m / z: 351.0980 (theoretical value: 351.0991).

[0232] [Synthetic Example 18] Synthesis of Intermediate 411-d

[0233]

[0234] Following the preparation method of Synthesis Example 1, 6-A was replaced with an equimolar amount of 411-A to obtain intermediate 411-d (12.92 g), with an HPLC purity ≥99.63%. Mass spectrometry m / z: 315.2199 (theoretical value: 315.2184).

[0235] [Synthetic Example 19] Synthesis of Intermediate 451-d

[0236]

[0237] Following the preparation method of Synthesis Example 1, 6-A and 6-B were replaced with equimolar amounts of 451-A and 451-B, respectively, to obtain intermediate 451-d (14.49 g), with an HPLC purity ≥99.71%. Mass spectrometry m / z: 362.1215 (theoretical value: 362.1227).

[0238] [Synthetic Example 20] Synthesis of Intermediate 468-d

[0239]

[0240] Following the preparation method of Synthesis Example 1, 6-A and 6-B were replaced with equimolar amounts of 33-A and 468-B, respectively, to obtain intermediate 468-d (17.55 g), with an HPLC purity ≥99.88%. Mass spectrometry m / z: 444.2039 (theoretical value: 444.2026).

[0241] [Synthetic Example 21] Synthesis of Intermediate 473-d

[0242]

[0243] Following the preparation method of Synthesis Example 14, 364-H and 6-B were replaced with equimolar amounts of 473-H and 473-J, respectively, to obtain intermediate 473-d (27.52 g), with an HPLC purity ≥99.68%. Mass spectrometry m / z: 705.2817 (theoretical value: 705.2839).

[0244] [Synthetic Example 22] Synthesis of Intermediate 493-d

[0245]

[0246] Following the preparation method of Synthesis Example 1, 6-A and 6-B were replaced with equimolar amounts of 33-A and 451-B, respectively, to obtain intermediate 493-d (13.94 g), with an HPLC purity ≥99.52%. Mass spectrometry m / z: 344.1702 (theoretical value: 344.1713).

[0247] [Synthetic Example 23] Synthesis of Compound 2

[0248]

[0249] Synthesis of intermediate 2-c

[0250] Under nitrogen protection, 2-a (21.04 g, 75.00 mmol), tetrahydrofuran (350 mL), and n-butyllithium (40 mL of 1.6 M hexane solution) were added to a reaction flask and stirred at -78 °C for 1 hour. Then, a tetrahydrofuran solution (150 mL) containing 2-b (15.02 g, 75 mmol) was added dropwise to the reaction flask, and the reaction was continued at -78 °C for 1 hour, followed by stirring at room temperature for 4 hours. After the reaction was complete, a saturated ammonium chloride solution was added to separate the organic layer, which was then concentrated. The concentrated organic solid, acetic anhydride (700 mL), and hydrochloric acid (30 mL) were added to a reaction flask and stirred at 100 °C for 4 hours. After the reaction was completed, cold water (300 mL) was added to precipitate the solid product, which was then filtered. The product was then purified by silica gel column chromatography (petroleum ether / dichloromethane = 10:1) to obtain intermediate 2-c (22.46 g, yield 78%) with HPLC purity ≥99.46% and mass spectrometry m / z: 383.0826 (theoretical value: 383.0877).

[0251] Synthesis of intermediate 2-e

[0252] Under argon protection, 2-d (12.63 g, 44 mmol), intermediate 2-c (15.35 g, 40 mmol), tetrakis(triphenylphosphine)palladium (0.58 g, 0.50 mmol), potassium acetate (7.65 g, 78.00 mmol), toluene (200 mL), ethanol (75 mL), and water (75 mL) were added sequentially to a reaction flask. The mixture was stirred and refluxed for 4 hours. After the reaction was completed, the mixture was cooled to room temperature, filtered to obtain a filter cake, and washed with ethanol. Finally, the filter cake was recrystallized from toluene / ethanol at a ratio of 10:3 to obtain intermediate 2-e (19.85 g, yield 84%) with an HPLC purity ≥99.83%. Mass spectrometry m / z: 590.2173 (theoretical value: 590.2158).

[0253] Synthesis of Compound 2

[0254] Under nitrogen protection, intermediate 2-e (16.54 g, 28 mmol), toluene (150 mL), 2-f (4.05 g, 25 mmol), tris(benzylacetone)palladium (0.23 g, 0.25 mmol), 1,1'-binaphthyl-2,2'-bis(diphenylphosphine) (0.50 g, 0.8 mmol), and sodium tert-butoxide (7.68 g, 80 mmol) were added to a reaction flask, stirred to dissolve, and refluxed for 8 hours. After the reaction was complete, the mixture was cooled to room temperature, filtered, and the organic solvent was removed by vacuum distillation. The obtained solid was recrystallized from methanol to give compound 2 (13.60 g, yield 81%), with an HPLC purity ≥99.94%. Mass spectrometry m / z: 671.2796 (theoretical value: 671.2785). Theoretical elemental content (%) C 49 H 26 D5FN2: C, 87.60; H, 5.40; N, 4.17. Measured elemental content (%): C, 87.62; H, 5.41; N, 4.14.

[0255] [Synthetic Example 24] Synthesis of Compound 6

[0256]

[0257] Following the preparation method of Synthesis Example 23, 2-a, 2-b, 2-d, 2-e, and 2-f were replaced with equimolar amounts of 6-a, 6-b, 6-d, 6-e, and 6-f, respectively, to obtain compound 6 (14.30 g) with an HPLC purity ≥99.98%. Mass spectrometry m / z: 794.4328 (theoretical value: 794.4383). Theoretical elemental content (%) C 59 H 30 D 14 N2: C, 89.13; H, 7.35; N, 3.52. Measured elemental content (%): C, 89.11; H, 7.36; N, 3.54.

[0258] [Synthetic Example 25] Synthesis of Compound 9

[0259]

[0260] Following the preparation method of Synthesis Example 23, 2-a, 2-b, 2-d, 2-e, and 2-f were replaced with equimolar amounts of 9-a, 9-b, 9-d, 9-e, and 9-B, respectively, to obtain compound 9 (15.58 g) with an HPLC purity ≥99.96%. Mass spectrometry m / z: 788.4052 (theoretical value: 788.4038). Theoretical elemental content (%) C 59 H 40D6N2: C, 89.81; H, 6.64; N, 3.55. Measured elemental content (%): C, 89.84; H, 6.62; N, 3.57.

[0261] [Synthetic Example 26] Synthesis of Compound 14

[0262]

[0263] Following the preparation method of Synthesis Example 23, 2-a, 2-b, 2-d, 2-e, and 2-f were replaced with equimolar amounts of 14-a, 14-b, 14-d, 14-e, and 9-B, respectively, to obtain compound 14 (15.70 g), with an HPLC purity ≥99.91%. Mass spectrometry m / z: 804.3518 (theoretical value: 804.3506). Theoretical elemental content (%) C 56 H 23 D 12 F3N2: C, 83.56; H, 5.88; N, 3.48. Measured elemental content (%): C, 83.59; H, 5.85; N, 3.46.

[0264] [Synthetic Example 27] Synthesis of Compound 27

[0265]

[0266] Following the preparation method of Synthesis Example 23, 2-b, 2-d, 2-e, and 2-f were replaced with equimolar amounts of 27-b, 6-d, 27-e, and 6-B, respectively, to obtain compound 27 (14.63 g) with an HPLC purity ≥99.97%. Mass spectrometry m / z: 759.3445 (theoretical value: 759.3459). Theoretical elemental content (%) C 56 H 25 D 10 N3: C, 88.50; H, 5.97; N, 5.53. Measured element content (%): C, 88.55; H, 5.94; N, 5.56.

[0267] [Synthetic Example 28] Synthesis of Compound 33

[0268]

[0269] Synthesis of intermediate 33-c

[0270] Under nitrogen protection, 33-a (14.27 g, 40.00 mmol), tetrahydrofuran (200 mL), and n-butyllithium (25 mL of 1.6 M hexane solution) were added to a reaction flask and stirred at -78 °C for 1 hour. Then, a tetrahydrofuran solution (100 mL) containing 33-b (12.58 g, 40 mmol) was added dropwise to the reaction flask, and the reaction was continued at -78 °C for 1 hour, followed by stirring at room temperature for 4 hours. After the reaction was complete, a saturated ammonium chloride solution was added to separate the organic layer, which was then concentrated. The concentrated organic solid, acetic anhydride (500 mL), and hydrochloric acid (20 mL) were added to a reaction flask and stirred at 100 °C for 4 hours. After the reaction was completed, cold water (200 mL) was added to precipitate the solid product, which was then filtered. The product was then purified by silica gel column chromatography (petroleum ether / dichloromethane = 10:1) to obtain intermediate 33-c (17.91 g, yield 78%) with HPLC purity ≥99.66% and mass spectrometry m / z: 573.2241 (theoretical value: 573.2223).

[0271] Synthesis of Compound 33

[0272] Under argon protection, 33-d (8.83 g, 28 mmol), intermediate 33-c (14.35 g, 25 mmol), tetratetraphenylphosphine palladium (0.35 g, 0.30 mmol), potassium acetate (4.91 g, 78.00 mmol), toluene (150 mL), ethanol (50 mL), and water (50 mL) were added sequentially to a reaction flask. The mixture was stirred and refluxed for 5 hours. After the reaction was completed, the mixture was cooled to room temperature, filtered to obtain a filter cake, and washed with ethanol. Finally, the filter cake was recrystallized from toluene / ethanol at a ratio of 5:1 to obtain intermediate 33 (16.26 g, yield 82%), with an HPLC purity ≥99.95%. Mass spectrometry m / z: 792.4245 (theoretical value: 792.4258). Theoretical elemental content (%) C 59 H 32 D 12 N2: C, 89.35; H, 7.11; N, 3.53. Measured elemental content (%): C, 89.38; H, 7.14; N, 3.50.

[0273] [Synthetic Example 29] Synthesis of Compound 40

[0274]

[0275] Following the preparation method of Synthesis Example 23, 2-a, 2-b, 2-d, 2-e, and 2-f were replaced with equimolar amounts of 40-a, 40-b, 33-d, 40-e, and 6-B, respectively, to obtain compound 40 (14.72 g) with an HPLC purity ≥99.92%. Mass spectrometry m / z: 735.4336 (theoretical value: 735.4322). Theoretical elemental content (%) C 54 H 13 D 23 N2: C, 88.12; H, 8.07; N, 3.81. Measured elemental content (%): C, 88.16; H, 8.04; N, 3.85.

[0276] [Synthetic Example 30] Synthesis of Compound 45

[0277]

[0278] Following the preparation method of Synthesis Example 28, 33-b and 33-d were replaced with equimolar amounts of 364-H and 45-d, respectively, to obtain compound 45 (15.19 g), with an HPLC purity ≥99.98%. Mass spectrometry m / z: 731.3302 (theoretical value: 731.3318). Theoretical elemental content (%) C 55 H 29 D7N2: C, 90.25; H, 5.92; N, 3.83. Measured elemental content (%): C, 90.29; H, 5.90; N, 3.85.

[0279] [Synthetic Example 31] Synthesis of Compound 51

[0280]

[0281] Following the preparation method of Synthesis Example 23, 2-a, 2-b, 2-d, 2-e, and 2-f were replaced with equimolar amounts of 51-a, 473-H, 51-d, 51-e, and 6-B, respectively, to obtain compound 51 (15.28 g) with an HPLC purity ≥99.93%. Mass spectrometry m / z: 763.2956 (theoretical value: 763.2941). Theoretical elemental content (%) C 50 H 18 D 11 F5N2: C, 78.62; H, 5.28; N, 3.67. Measured elemental content (%): C, 78.66; H, 5.25; N, 3.64.

[0282] [Synthetic Example 32] Synthesis of Compound 58

[0283]

[0284] Following the preparation method of Synthesis Example 23, 2-b, 2-d, 2-e, and 2-f were replaced with equimolar amounts of 473-H, 58-d, 58-e, and 58-f, respectively, to obtain compound 58 (14.19 g), with an HPLC purity ≥99.96%. Mass spectrometry m / z: 819.3674 (theoretical value: 819.3662). Theoretical elemental content (%) C 62 H 37 D5N2: C, 90.81; H, 5.78; N, 3.42. Measured elemental content (%): C, 90.80; H, 5.77; N, 3.44.

[0285] [Synthetic Example 33] Synthesis of Compound 105

[0286]

[0287] Following the preparation method of Synthesis Example 23, 2-b, 2-d, 2-e, and 2-f were replaced with equimolar amounts of 473-H, 105-d, 105-e, and 105-f, respectively, to obtain compound 105 (15.13 g) with an HPLC purity ≥99.98%. Mass spectrometry m / z: 775.3958 (theoretical value: 775.3944). Theoretical elemental content (%) C 58 H 37 D7N2: C, 89.77; H, 6.62; N, 3.61. Measured elemental content (%): C, 89.73; H, 6.65; N, 3.63.

[0288] [Synthetic Example 34] Synthesis of Compound 124

[0289]

[0290] Following the preparation method of Synthesis Example 23, 2-a, 2-b, 2-e, and 2-f were replaced with equimolar amounts of 40-a, 364-H, 124-e, and 9-B, respectively, to obtain compound 124 (14.98 g) with an HPLC purity ≥99.93%. Mass spectrometry m / z: 730.3242 (theoretical value: 730.3255). Theoretical elemental content (%) C 55 H 30 D6N2: C, 90.38; H, 5.79; N, 3.83. Measured elemental content (%): C, 90.35; H, 5.77; N, 3.86.

[0291] [Synthetic Example 35] Synthesis of Compound 129

[0292]

[0293] Following the preparation method of Synthesis Example 28, 33-b and 33-d were replaced with equimolar amounts of 129-b and 2-d, respectively, to obtain compound 129 (15.31 g), with an HPLC purity ≥99.94%. Mass spectrometry m / z: 737.3682 (theoretical value: 737.3694). Theoretical elemental content (%) C 55 H 23 D 13 N2: C, 89.51; H, 6.69; N, 3.80. Measured elemental content (%): C, 89.53; H, 6.65; N, 3.82.

[0294] [Synthetic Example 36] Synthesis of Compound 138

[0295]

[0296] Following the preparation method of Synthesis Example 23, 2-b, 2-d, 2-e, and 2-f were replaced with equimolar amounts of 364-H, 6-d, 138-e, and 6-B, respectively, to obtain compound 138 (14.88 g) with an HPLC purity ≥99.98%. Mass spectrometry m / z: 734.3519 (theoretical value: 734.3506). Theoretical elemental content (%) C 55 H 26 D 10 N2: C, 89.88; H, 6.31; N, 3.81. Measured elemental content (%): C, 89.86; H, 6.33; N, 3.86.

[0297] [Synthetic Example 37] Synthesis of Compound 143

[0298]

[0299] Following the preparation method of Synthesis Example 23, 2-b, 2-e, and 2-f were replaced with equimolar amounts of 143-b, 143-e, and 51-B, respectively, to obtain compound 143 (15.97 g) with an HPLC purity ≥99.92%. Mass spectrometry m / z: 818.2646 (theoretical value: 818.2658). Theoretical elemental content (%) C 55 H 27 D4F5N2: C, 80.67; H, 4.31; N, 3.42. Measured elemental content (%): C, 80.65; H, 4.35; N, 3.40.

[0300] [Synthetic Example 38] Synthesis of Compound 145

[0301]

[0302] Following the preparation method of Synthesis Example 23, 2-b, 2-d, 2-e, and 2-f were replaced with equimolar amounts of 364-H, 45-d, 145-e, and 145-f, respectively, to obtain compound 145 (15.56 g) with an HPLC purity ≥99.97%. Mass spectrometry m / z: 787.3959 (theoretical value: 787.3944). Theoretical elemental content (%) C 59 H 37 D7N2: C, 89.92; H, 6.52; N, 3.55. Measured elemental content (%): C, 89.90; H, 6.55; N, 3.53.

[0303] [Synthetic Example 39] Synthesis of Compound 156

[0304]

[0305] Following the preparation method of Synthesis Example 23, 2-b, 2-d, 2-e, and 2-f were replaced with equimolar amounts of 376-H, 6-d, 156-e, and 156-f, respectively, to obtain compound 156 (14.82 g) with an HPLC purity ≥99.91%. Mass spectrometry m / z: 759.3442 (theoretical value: 759.3459). Theoretical elemental content (%) C 56 H 25 D 10 N3: C, 88.50; H, 5.97; N, 5.53. Measured elemental content (%): C, 88.55; H, 5.94; N, 5.50.

[0306] [Synthetic Example 40] Synthesis of Compound 178

[0307]

[0308] Following the preparation method of Synthesis Example 23, 2-a, 2-b, 2-d, 2-e, and 2-f were replaced with equimolar amounts of 14-a, 376-H, 178-d, 178-e, and 178-B, respectively, to obtain compound 178 (16.04 g) with an HPLC purity ≥99.96%. Mass spectrometry m / z: 843.4396 (theoretical value: 843.4384). Theoretical elemental content (%) C 63 H 21 D 19 N2: C, 89.64; H, 7.04; N, 3.32. Measured elemental content (%): C, 89.66; H, 7.08; N, 3.30.

[0309] [Synthetic Example 41] Synthesis of Compound 201

[0310]

[0311] Following the preparation method of Synthesis Example 23, 2-a, 2-b, 2-d, 2-e, and 2-f were replaced with equimolar amounts of 201-a, 364-H, 201-d, 201-e, and 6-B, respectively, to obtain compound 201 (15.50 g) with an HPLC purity ≥99.93%. Mass spectrometry m / z: 784.3650 (theoretical value: 784.3663). Theoretical elemental content (%) C 59 H 28 D 10 N2: C, 90.27; H, 6.16; N, 3.57. Measured elemental content (%): C, 90.23; H, 6.18; N, 3.55.

[0312] [Synthetic Example 42] Synthesis of Compound 206

[0313]

[0314] Synthesis of intermediate 206-c

[0315] Following the preparation method of Synthesis Example 28, 33-b was replaced with an equimolar amount of 473-H to obtain intermediate 206-c (14.59 g), with an HPLC purity ≥99.78%. Mass spectrometry m / z: 455.1459 (theoretical value: 455.1441).

[0316] Synthesis of Compound 206

[0317] Under nitrogen protection, intermediates 206-d (12.44 g, 25.00 mmol), 206-c (11.40 g, 25.00 mmol), tris(benzylacetone)palladium (0.27 g, 0.30 mmol), tri-tert-butylphosphine (1.20 mL of 0.5 M toluene solution, 0.60 mmol), potassium carbonate (5.53 g, 40.00 mmol), and tetrahydrofuran (250 mL) were added sequentially to a reaction flask. The mixture was stirred and the reaction system was heated under reflux for 5 hours. After the reaction was completed, the mixture was cooled to room temperature, filtered to obtain a filter cake, and washed with a small amount of toluene. Finally, the filter cake was recrystallized from toluene to obtain compound 206 (16.22 g, yield 82%); HPLC purity ≥99.98%. Mass spectrometry m / z: 790.4142 (theoretical value: 790.4101). Theoretical elemental content (%) C 59 H 30 D 12 N2: C, 89.58; H, 6.88; N, 3.54. Measured elemental content (%): C, 89.55; H, 6.86; N, 3.59.

[0318] [Synthetic Example 43] Synthesis of Compound 217

[0319]

[0320] Synthesis of intermediate 217-c

[0321] Following the preparation method of Synthesis Example 23, 2-a and 2-b were replaced with equimolar amounts of 40-a and 473-H, respectively, to obtain intermediate 217-c (23.16 g), with an HPLC purity ≥99.68%. Mass spectrometry m / z: 385.1518 (theoretical value: 385.1504).

[0322] Synthesis of intermediate 217-e

[0323] Under nitrogen protection, intermediates 217-d (18.02 g, 40.00 mmol), 206-c (15.44 g, 40.00 mmol), tris(benzylacetone)palladium (0.44 g, 0.48 mmol), tri-tert-butylphosphine (1.92 mL of 0.5 M toluene solution, 0.96 mmol), potassium carbonate (8.85 g, 64.00 mmol), and tetrahydrofuran (300 mL) were added sequentially to a reaction flask. The mixture was stirred and the reaction system was heated under reflux for 5 hours. After the reaction was completed, the mixture was cooled to room temperature, filtered to obtain a filter cake, and washed with a small amount of toluene. Finally, the filter cake was recrystallized from toluene to obtain intermediate 217-e (21.56 g, yield 80%); HPLC purity ≥99.42%. Mass spectrometry m / z: 673.3401 (theoretical value: 673.3412).

[0324] Synthesis of Compound 217

[0325] Following the preparation method of Synthesis Example 23, 2-e and 2-f were replaced with equimolar amounts of 217-e and 6-B, respectively, to obtain compound 217 (15.29 g), with an HPLC purity ≥99.98%. Mass spectrometry m / z: 754.4052 (theoretical value: 754.4039). Theoretical elemental content (%) C 56 H 22 D 16 N2: C, 89.08; H, 7.21; N, 3.71. Measured elemental content (%): C, 89.03; H, 7.26; N, 3.74.

[0326] [Synthetic Example 44] Synthesis of Compound 244

[0327]

[0328] Following the preparation method of Synthesis Example 43, 40-a, 217-d, 217-e, and 6-B were replaced with equimolar amounts of 244-a, 244-d, 244-e, and 9-B, respectively, to obtain compound 244 (18.59 g) with an HPLC purity ≥99.93%. Mass spectrometry m / z: 928.4652 (theoretical value: 928.4664). Theoretical elemental content (%) C 70 H 48 D6N2: C, 90.48; H, 6.51; N, 3.01. Measured elemental content (%): C, 90.45; H, 6.53; N, 3.06.

[0329] [Synthetic Example 45] Synthesis of Compound 311

[0330]

[0331] Following the preparation method of Synthesis Example 43, 473-H, 217-d, and 217-e were replaced with equimolar amounts of 311-b, 311-d, and 311-e, respectively, to obtain compound 311 (17.79 g) with an HPLC purity ≥99.96%. Mass spectrometry m / z: 911.3956 (theoretical value: 911.3943). Theoretical elemental content (%) C 67 H 29 D 11 N4: C, 88.22; H, 5.63; N, 6.14. Measured elemental content (%): C, 88.26; H, 5.60; N, 6.11.

[0332] [Synthetic Example 46] Synthesis of Compound 364

[0333]

[0334] Following the preparation method of Synthesis Example 23, 2-b, 2-d, 2-e, and 2-f were replaced with equimolar amounts of 364-H, 364-d, 364-e, and 6-B, respectively, to obtain compound 364 (19.26 g) with an HPLC purity ≥99.91%. Mass spectrometry m / z: 974.4431 (theoretical value: 974.4445). Theoretical elemental content (%) C 74 H 38 D 10 N2: C, 91.13; H, 5.99; N, 2.87. Measured elemental content (%): C, 91.18; H, 5.97; N, 2.84.

[0335] [Synthetic Example 47] Synthesis of Compound 376

[0336]

[0337] Following the preparation method of Synthesis Example 23, 2-b, 2-d, 2-e, and 2-f were replaced with equimolar amounts of 376-H, 376-d, 376-e, and 376-J, respectively, to obtain compound 376 (21.47 g) with an HPLC purity ≥99.97%. Mass spectrometry m / z: 1114.6024 (theoretical value: 1114.6010). Theoretical elemental content (%) C 84 H 58 D 10 N2: C, 90.44; H, 7.05; N, 2.51. Measured elemental content (%): C, 90.48; H, 7.03; N, 2.56.

[0338] [Synthetic Example 48] Synthesis of Compound 382

[0339]

[0340] Following the preparation method of Synthesis Example 23, 2-b, 2-d, 2-e, and 2-f were replaced with equimolar amounts of 473-H, 382-d, 382-e, and 178-B, respectively, to obtain compound 382 (17.70 g) with an HPLC purity ≥99.93%. Mass spectrometry m / z: 895.3930 (theoretical value: 895.3944). Theoretical elemental content (%) C 68 H 37 D7N2: C, 91.14; H, 5.74; N, 3.13. Measured elemental content (%): C, 91.18; H, 5.70; N, 3.11.

[0341] [Synthetic Example 49] Synthesis of Compound 388

[0342]

[0343] Following the preparation method of Synthesis Example 23, 2-a, 2-b, 2-e, and 2-f were replaced with equimolar amounts of 40-a, 473-H, 388-e, and 6-B, respectively, to obtain compound 388 (13.82 g) with an HPLC purity ≥99.94%. Mass spectrometry m / z: 673.3425 (theoretical value: 673.3412). Theoretical elemental content (%) C 50 H 23 D 11 N2: C, 89.12; H, 6.73; N, 4.16. Measured elemental content (%): C, 89.15; H, 6.70; N, 4.14.

[0344] [Synthetic Example 50] Synthesis of Compound 391

[0345]

[0346] Following the preparation method of Synthesis Example 23, 2-b, 2-d, 2-e, and 2-f were replaced with equimolar amounts of 473-H, 391-d, 391-e, and 6-f, respectively, to obtain compound 391 (16.32 g) with an HPLC purity ≥99.97%. Mass spectrometry m / z: 815.3460 (theoretical value: 815.3474). Theoretical elemental content (%) C 57 H 28 D9F3N2: C, 83.90; H, 5.68; N, 3.43. Measured elemental content (%): C, 83.93; H, 5.65; N, 3.46.

[0347] [Synthetic Example 51] Synthesis of Compound 405

[0348]

[0349] Following the preparation method of Synthesis Example 23, 2-a, 2-b, 2-d, 2-e, and 2-f were replaced with equimolar amounts of 51-a, 405-b, 33-d, 405-e, and 6-B, respectively, to obtain compound 405 (15.76 g) with an HPLC purity ≥99.92%. Mass spectrometry m / z: 797.4490 (theoretical value: 797.4479). Theoretical elemental content (%) C 59 H 15 D 23 N2: C, 88.79; H, 7.70; N, 3.51. Measured elemental content (%): C, 88.76; H, 7.72; N, 3.53.

[0350] [Synthetic Example 52] Synthesis of Compound 411

[0351]

[0352] Following the preparation method of Synthesis Example 23, 2-a, 2-b, 2-d, 2-e, and 2-f were replaced with equimolar amounts of 411-a, 364-H, 411-d, 411-e, and 411-f, respectively, to obtain compound 411 (16.32 g) with an HPLC purity ≥99.96%. Mass spectrometry m / z: 836.3931 (theoretical value: 836.3945). Theoretical elemental content (%) C 63 H 28 D 12 N2: C, 90.39; H, 6.26; N, 3.35. Measured elemental content (%): C, 90.36; H, 6.22; N, 3.39.

[0353] [Synthetic Example 53] Synthesis of Compound 421

[0354]

[0355] Following the preparation method of Synthesis Example 23, 2-a, 2-b, 2-d, 2-e, and 2-f were replaced with equimolar amounts of 421-a, 364-H, 6-d, 421-e, and 6-B, respectively, to obtain compound 421 (15.70 g) with an HPLC purity ≥99.98%. Mass spectrometry m / z: 784.3678 (theoretical value: 784.3663). Theoretical elemental content (%) C 59 H 28 D 10 N2: C, 90.27; H, 6.16; N, 3.57. Measured elemental content (%): C, 90.22; H, 6.18; N, 3.55.

[0356] [Synthetic Example 54] Synthesis of Compound 428

[0357]

[0358] Following the preparation method of Synthesis Example 23, 2-a, 2-b, 2-d, 2-e, and 2-f were replaced with equimolar amounts of 40-a, 364-H, 33-d, 428-e, and 6-B, respectively, to obtain compound 428 (15.15 g) with an HPLC purity ≥99.91%. Mass spectrometry m / z: 747.431 (theoretical value: 747.4322). Theoretical elemental content (%) C 55 H 13 D 23 N2: C, 88.31; H, 7.94; N, 3.74. Measured elemental content (%): C, 88.35; H, 7.90; N, 3.77.

[0359] [Synthetic Example 55] Synthesis of Compound 438

[0360]

[0361] Following the preparation method of Synthesis Example 28, 33-b was replaced with an equimolar amount of 438-b to obtain compound 438 (17.16 g), with an HPLC purity ≥99.94%. Mass spectrometry m / z: 836.3932 (theoretical value: 836.3945). Theoretical elemental content (%) C 63 H 28 D 12 N2: C, 90.39; H, 6.26; N, 3.35. Measured elemental content (%): C, 90.35; H, 6.22; N, 3.39.

[0362] [Synthetic Example 56] Synthesis of Compound 441

[0363]

[0364] Following the preparation method of Synthesis Example 23, 2-a, 2-b, 2-d, 2-e, and 2-f were replaced with equimolar amounts of 40-a, 364-H, 6-d, 441-e, and 441-f, respectively, to obtain compound 441 (19.04 g), with an HPLC purity ≥99.95%. Mass spectrometry m / z: 975.4519 (theoretical value: 975.4508). Theoretical elemental content (%) C 74 H 37 D 11 N2: C, 91.04; H, 6.09; N, 2.87. Measured elemental content (%): C, 91.08; H, 6.03; N, 2.85.

[0365] [Synthetic Example 57] Synthesis of Compound 451

[0366]

[0367] Following the preparation method of Synthesis Example 23, 2-a, 2-b, 2-d, 2-e, and 2-f were replaced with equimolar amounts of 451-a, 473-H, 451-d, 451-e, and 451-f, respectively, to obtain compound 451 (18.91 g), with an HPLC purity ≥99.93%. Mass spectrometry m / z: 981.3978 (theoretical value: 981.3990). Theoretical elemental content (%) C 74 H 39 D6N3: C, 90.49; H, 5.23; N, 4.28. Measured elemental content (%): C, 90.46; H, 5.25; N, 4.25.

[0368] [Synthetic Example 58] Synthesis of Compound 468

[0369]

[0370] Following the preparation method of Synthesis Example 23, 2-a, 2-b, 2-d, 2-e, and 2-f were replaced with equimolar amounts of 40-a, 473-H, 468-d, 468-e, and 468-f, respectively, to obtain compound 468 (18.81 g) with an HPLC purity ≥99.96%. Mass spectrometry m / z: 951.4489 (theoretical value: 951.4477). Theoretical elemental content (%) C 72 H 33 D 13 N2: C, 90.82; H, 6.24; N, 2.94. Measured elemental content (%): C, 90.80; H, 6.26; N, 2.92.

[0371] [Synthetic Example 59] Synthesis of Compound 473

[0372]

[0373] Following the preparation method of Synthesis Example 23, 2-a, 2-b, 2-d, 2-e, and 2-f were replaced with equimolar amounts of 40-a, 473-H, 473-d, 473-e, and 6-B, respectively, to obtain compound 473 (21.85 g) with an HPLC purity ≥99.92%. Mass spectrometry m / z: 1091.5120 (theoretical value: 1091.5134). Theoretical elemental content (%) C 83 H 45 D 11 N2: C, 91.26; H, 6.18; N, 2.56. Measured elemental content (%): C, 91.29; H, 6.16; N, 2.58.

[0374] [Synthetic Example 60] Synthesis of Compound 493

[0375]

[0376] Following the preparation method of Synthesis Example 23, 2-a, 2-b, 2-d, 2-e, and 2-f were replaced with equimolar amounts of 40-a, 14-b, 493-d, 493-e, and 9-B, respectively, to obtain compound 493 (19.38 g) with an HPLC purity ≥99.97%. Mass spectrometry m / z: 956.3973 (theoretical value: 956.3990). Theoretical elemental content (%) C 67 H 27 D 13 F3N3: C, 84.08; H, 5.58; N, 4.39. Measured elemental content (%): C, 84.10; H, 5.55; N, 4.37.

[0377] [Synthetic Example 61] Synthesis of Compound 527

[0378]

[0379] Following the preparation method of Synthesis Example 23, 2-b, 2-d, 2-e, and 2-f were replaced with equimolar amounts of 473-H, 527-d, 58-e, and 527-f, respectively, to obtain compound 527 (17.14 g) with an HPLC purity ≥99.98%. Mass spectrometry m / z: 820.3685 (theoretical value: 820.3614). Theoretical elemental content (%) C 61 H 36 D5N3: C, 89.24; H, 5.65; N, 5.12. Measured elemental content (%): C, 89.21; H, 5.66; N, 5.14.

[0380] [Device Examples 1-38]

[0381] Device Example 1: The ITO glass substrate was ultrasonically cleaned twice with a 5% glass cleaning solution for 20 minutes each time, followed by ultrasonic cleaning twice with deionized water for 10 minutes each time. It was then ultrasonically cleaned sequentially with acetone and isoacetone for 20 minutes each time, and dried at 120°C. HI was vacuum-deposited on the ITO substrate as a hole injection layer with a thickness of 25 nm; HT was vacuum-deposited on the hole injection layer as a hole transport layer with a thickness of 80 nm; Compound 2 of this invention:GD = 94:6 (mass ratio) was vacuum-deposited on the hole transport layer as a light-emitting layer with a thickness of 20 nm; ET was vacuum-deposited on the light-emitting layer as an electron transport layer with a thickness of 30 nm; LiF was vacuum-deposited on the electron transport layer as an electron injection layer with a thickness of 1 nm; and Al was vacuum-deposited on the electron injection layer as a cathode with a thickness of 70 nm.

[0382]

[0383] Device Examples 2-38: Compounds 6, 9, 14, 27, 33, 40, 45, 51, 58, 105, 124, 129, 138, 143, 145, 156, 178, 201, 206, 217, 244, 311, 364, 376, 382, ​​388, 391, 405, 411, 421, 428, 438, 441, 451, 468, 473, 493, and 527 of the present invention were used to replace compound 2 of the present invention in Device Example 1 as the main material. Otherwise, organic electroluminescent devices were prepared using the same steps as in Device Example 1.

[0384] Comparative Examples 1 and 2: Comparative Compound 1 and Comparative Compound 2 were used to replace Compound 2 of the present invention in Device Example 1 as the main material, respectively. Otherwise, the organic electroluminescent devices were prepared using the same steps as in Device Example 1.

[0385] A combined IVL testing system was used to test the luminous efficiency of electromechanical light-emitting devices (EMFs), comprising testing software, a computer, a Keithley K2400 digital source meter, and a PhotoResearch PR788 spectral scanning luminance meter. Lifetime testing was performed using a McScience M6000 OLED lifetime testing system. The testing environment was atmospheric, at room temperature.

[0386] The luminescence characteristics of the obtained organic electroluminescent devices are shown in Table 1. Table 1 shows the luminescence characteristics of the organic electroluminescent devices prepared by the compounds prepared in the embodiments of the present invention and the comparative substances.

[0387] Table 1. Luminescence characteristics test of organic electroluminescent devices

[0388]

[0389]

[0390]

[0391] As can be seen from the results in Table 1, compared with Comparative Examples 1-2, the organic electroluminescent devices in Device Examples 1-38 have higher luminous efficiency and longer device lifetime.

[0392] [Device Examples 39-76]

[0393] Device Example 39: The ITO glass substrate was ultrasonically cleaned twice with a 5% glass cleaning solution for 20 minutes each time, and then ultrasonically cleaned twice with deionized water for 10 minutes each time. It was then ultrasonically cleaned sequentially with acetone and isoacetone for 20 minutes each time, and dried at 120°C. HI was vacuum-deposited on the ITO substrate as a hole injection layer with a thickness of 25 nm; HT was vacuum-deposited on the hole injection layer as a hole transport layer with a thickness of 80 nm; compound 2:RD (mass ratio) of the present invention was vacuum-deposited on the hole transport layer as a light-emitting layer with a thickness of 20 nm; ET was vacuum-deposited on the light-emitting layer as an electron transport layer with a thickness of 30 nm; LiF was vacuum-deposited on the electron transport layer as an electron injection layer with a thickness of 1 nm; and Al was vacuum-deposited on the electron injection layer as a cathode with a thickness of 70 nm.

[0394] Device Examples 40–76: Compound 2 of the present invention in Device Example 39 was replaced with compounds 6, 9, 14, 27, 33, 40, 45, 51, 58, 105, 124, 129, 138, 143, 145, 156, 178, 201, 206, 217, 244, 311, 364, 376, 382, ​​388, 391, 405, 411, 421, 428, 438, 441, 451, 468, 473, 493, and 527 as the main material. Otherwise, organic electroluminescent devices were prepared using the same steps as in Device Example 9.

[0395] Comparative Examples 3-4: Comparative Compound 1 and Comparative Compound 2 were used to replace Compound 2 of the present invention in Device Example 39 as the main material, respectively. Otherwise, the organic electroluminescent devices were prepared using the same steps as in Device Example 39.

[0396] A combined IVL testing system was used to test the luminous efficiency of organic electroluminescent devices (OLEDs), comprising testing software, a computer, a Keithley K2400 digital source meter, and a PhotoResearch PR788 spectral scanning luminance meter. Lifetime testing was performed using a McScience M6000 OLED lifetime testing system. The testing environment was atmospheric, at room temperature.

[0397] The luminescence characteristics of the obtained organic electroluminescent devices are shown in Table 2. Table 2 shows the luminescence characteristics of the organic electroluminescent devices prepared by the compounds prepared in the embodiments of the invention and the comparative materials.

[0398] Table 2. Luminescence characteristics test of organic electroluminescent devices

[0399]

[0400]

[0401]

[0402] As can be seen from the results in Table 2, compared with Comparative Examples 3-4, the devices of Examples 39-76 exhibit higher luminous efficiency and longer device lifetime.

[0403] 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. A carbazole compound, characterized in that, The carbazole compounds have the structure shown in Formula 1. The x and z that are the same or different are selected from CH or N; among the four x in each ring, at most one is selected from N; among the four z in each ring, at most one is selected from N. The Choose any one of the structures shown below. The Ra is selected from any one of fluorine, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraceneyl, and substituted or unsubstituted phenanthryl. When Ra is a substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, or substituted or unsubstituted adamantyl, the substituent is selected from any one of deuterium, fluorine, methyl, or deuterated methyl. When two or more substituents are present, the two or more substituents are the same as or different from each other. When Ra is a substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraceneyl, or substituted or unsubstituted phenanthryl, the substituent is selected from any one of deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, deuterated methyl, deuterated isopropyl, deuterated tert-butyl, trifluoromethyl, or phenyl. When two or more substituents are present, the two or more substituents are the same as or different from each other. The Ar1 and Ar2, whether identical or different, are selected from any of the structures shown below. The Rb and Rc that are the same or different are selected from any one of substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, and substituted or unsubstituted naphthyl. When Rb and Rc are substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, or substituted or unsubstituted tert-butyl, the substituent is selected from deuterium and fluorine. When two or more substituents are present, the two or more substituents are the same as or different from each other. When Rb and Rc are substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or substituted or unsubstituted naphthyl, the substituent is selected from deuterium, fluorine, methyl, ethyl, isopropyl, tert-butyl, deuterated methyl, deuterated isopropyl, deuterated tert-butyl, or trifluoromethyl. When two or more substituents are present, the two or more substituents are the same as or different from each other. The m 11 The m4 is selected from 7; the m4 is selected from 1, 2, 3, 4 or 5; the m 41 Selected from 5; the m 42 The m5 is selected from 4; the m5 is selected from 1, 2, 3 or 4; the m 51 The m6 is selected from 4; the m6 is selected from 1, 2, 3, 4, 5, 6, 7 or 8; The same or different R2 is selected from any one of hydrogen, deuterium, fluorine, cyano, substituted or unsubstituted C1-C6 alkyl groups; the "substituted or unsubstituted C1-C6 alkyl group" means that it is not substituted or is substituted by one or more substituents selected from the group consisting of: deuterium, fluorine; The R3 is the same as or different from any one of hydrogen, deuterium, fluorine, cyano, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted fluorenyl; the "substituted or unsubstituted" in "substituted or unsubstituted C1-C6 alkyl" means unsubstituted or substituted by one or more substituents selected from the group consisting of: deuterium, fluorine; the "substituted or unsubstituted" in "substituted or unsubstituted fluorenyl" means unsubstituted or substituted by one or more substituents selected from the group consisting of: deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, phenyl; The b is selected from 1, 2, 3, 4, 5 or 6; when there are two or more R2s, the two or more R2s are the same or different from each other, or adjacent R2s are connected to each other to form a substituted or unsubstituted benzene ring; the "substituted or unsubstituted benzene ring" means that it is not substituted or is substituted by one or more substituents selected from the group consisting of: deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl; The c is selected from 1, 2, 3, 4, 5, 6 or 7; when there are two or more R3s, the two or more R3s are the same or different from each other, or adjacent R3s are connected to each other to form a substituted or unsubstituted benzene ring; the "substituted or unsubstituted benzene ring" means that it is not substituted or is substituted by one or more substituents selected from the group consisting of: deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl; The L0 is selected from a single bond or any of the structures shown below. The L1 and L2, whether identical or different, are selected from single bonds or any of the structures shown below. The same or different R5s are selected from any one of hydrogen, deuterium, fluorine, cyano, substituted or unsubstituted C1-C6 alkyl groups; the "substituted or unsubstituted C1-C6 alkyl group" means that it is not substituted or is substituted by one or more substituents selected from the group consisting of: deuterium, fluorine; The n1 that is the same or different is selected from 1, 2, 3 or 4; the n2 that is the same or different is selected from 1, 2, 3, 4, 5 or 6; the n3 that is the same or different is selected from 1, 2, 3, 4, 5, 6, 7 or 8; the n4 that is the same or different is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; when there are two or more R5, the two or more R5 are the same or different from each other.

2. A carbazole compound, characterized in that, The carbazole compounds have the structure shown in Formula 1. The x and z that are the same or different are selected from CH or N; among the four x in each ring, at most one is selected from N; among the four z in each ring, at most one is selected from N. The Choose any one of the structures shown below. The Ra is selected from any one of fluorine, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraceneyl, and substituted or unsubstituted phenanthryl. When Ra is a substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, or substituted or unsubstituted adamantyl, the substituent is selected from any one of deuterium, fluorine, methyl, or deuterated methyl. When two or more substituents are present, the two or more substituents are the same as or different from each other. When Ra is a substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraceneyl, or substituted or unsubstituted phenanthryl, the substituent is selected from any one of deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, deuterated methyl, deuterated isopropyl, deuterated tert-butyl, trifluoromethyl, or phenyl. When two or more substituents are present, the two or more substituents are the same as or different from each other. The Ar1 is selected from any of the structures shown below. The Ar2 is selected from any of the structures shown below. The Rb and Rc that are the same or different are selected from any one of substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, and substituted or unsubstituted naphthyl. When Rb and Rc are substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, or substituted or unsubstituted tert-butyl, the substituent is selected from deuterium and fluorine. When two or more substituents are present, the two or more substituents are the same as or different from each other. When Rb and Rc are substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or substituted or unsubstituted naphthyl, the substituent is selected from deuterium, fluorine, methyl, ethyl, isopropyl, tert-butyl, deuterated methyl, deuterated isopropyl, deuterated tert-butyl, or trifluoromethyl. When two or more substituents are present, the two or more substituents are the same as or different from each other. The m 11 The m4 is selected from 7; the m4 is selected from 1, 2, 3, 4 or 5; the m 41 Selected from 5; the m 42 The m5 is selected from 4; the m5 is selected from 1, 2, 3 or 4; the m 51 The m6 is selected from 4; the m6 is selected from 1, 2, 3, 4, 5, 6, 7 or 8; The same or different R2 is selected from any one of hydrogen, deuterium, fluorine, cyano, substituted or unsubstituted C1-C6 alkyl groups; the "substituted or unsubstituted C1-C6 alkyl group" means that it is not substituted or is substituted by one or more substituents selected from the group consisting of: deuterium, fluorine; The R3 is the same as or different from any one of hydrogen, deuterium, fluorine, cyano, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted fluorenyl; the "substituted or unsubstituted" in "substituted or unsubstituted C1-C6 alkyl" means unsubstituted or substituted by one or more substituents selected from the group consisting of: deuterium, fluorine; the "substituted or unsubstituted" in "substituted or unsubstituted fluorenyl" means unsubstituted or substituted by one or more substituents selected from the group consisting of: deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, phenyl; The b is selected from 1, 2, 3, 4, 5 or 6; when there are two or more R2s, the two or more R2s are the same or different from each other, or adjacent R2s are connected to each other to form a substituted or unsubstituted benzene ring; the "substituted or unsubstituted benzene ring" means that it is not substituted or is substituted by one or more substituents selected from the group consisting of: deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl; The c is selected from 1, 2, 3, 4, 5, 6 or 7; when there are two or more R3s, the two or more R3s are the same or different from each other, or adjacent R3s are connected to each other to form a substituted or unsubstituted benzene ring; the "substituted or unsubstituted benzene ring" means that it is not substituted or is substituted by one or more substituents selected from the group consisting of: deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl; The L0 is selected from a single bond or any of the structures shown below. The L1 and L2, whether identical or different, are selected from single bonds or any of the structures shown below. The same or different R5s are selected from any one of hydrogen, deuterium, fluorine, cyano, substituted or unsubstituted C1-C6 alkyl groups; the "substituted or unsubstituted C1-C6 alkyl group" means that it is not substituted or is substituted by one or more substituents selected from the group consisting of: deuterium, fluorine; The n1 that is the same or different is selected from 1, 2, 3 or 4; the n2 that is the same or different is selected from 1, 2, 3, 4, 5 or 6; the n3 that is the same or different is selected from 1, 2, 3, 4, 5, 6, 7 or 8; the n4 that is the same or different is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; when there are two or more R5, the two or more R5 are the same or different from each other.

3. A carbazole compound, characterized in that, The carbazole compounds have the structure shown in Formula 1. The x and z that are the same or different are selected from CH or N; among the four x in each ring, at most one is selected from N; among the four z in each ring, at most one is selected from N. The Choose any one of the structures shown below. The Ra is selected from any one of fluorine, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraceneyl, and substituted or unsubstituted phenanthryl. When Ra is a substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, or substituted or unsubstituted adamantyl, the substituent is selected from any one of deuterium, fluorine, methyl, or deuterated methyl. When two or more substituents are present, the two or more substituents are the same as or different from each other. When Ra is a substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraceneyl, or substituted or unsubstituted phenanthryl, the substituent is selected from any one of deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, deuterated methyl, deuterated isopropyl, deuterated tert-butyl, trifluoromethyl, or phenyl. When two or more substituents are present, the two or more substituents are the same as or different from each other. The Ar1 is selected from any of the structures shown below. The Ar2 is selected from any of the structures shown below. The Rb and Rc that are the same or different are selected from any one of substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, and substituted or unsubstituted naphthyl. When Rb and Rc are substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, or substituted or unsubstituted tert-butyl, the substituent is selected from deuterium and fluorine. When two or more substituents are present, the two or more substituents are the same as or different from each other. When Rb and Rc are substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or substituted or unsubstituted naphthyl, the substituent is selected from deuterium, fluorine, methyl, ethyl, isopropyl, tert-butyl, deuterated methyl, deuterated isopropyl, deuterated tert-butyl, or trifluoromethyl. When two or more substituents are present, the two or more substituents are the same as or different from each other. The m 11 The m4 is selected from 7; the m4 is selected from 1, 2, 3, 4 or 5; the m 41 Selected from 5; the m 42 The m5 is selected from 4; the m5 is selected from 1, 2, 3 or 4; the m 51 The m6 is selected from 4; the m6 is selected from 1, 2, 3, 4, 5, 6, 7 or 8; The same or different R2 is selected from any one of hydrogen, deuterium, fluorine, cyano, substituted or unsubstituted C1-C6 alkyl groups; the "substituted or unsubstituted C1-C6 alkyl group" means that it is not substituted or is substituted by one or more substituents selected from the group consisting of: deuterium, fluorine; The R3 is the same as or different from any one of hydrogen, deuterium, fluorine, cyano, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted fluorenyl; the "substituted or unsubstituted" in "substituted or unsubstituted C1-C6 alkyl" means unsubstituted or substituted by one or more substituents selected from the group consisting of: deuterium, fluorine; the "substituted or unsubstituted" in "substituted or unsubstituted fluorenyl" means unsubstituted or substituted by one or more substituents selected from the group consisting of: deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, phenyl; The b is selected from 1, 2, 3, 4, 5 or 6; when there are two or more R2s, the two or more R2s are the same or different from each other, or adjacent R2s are connected to each other to form a substituted or unsubstituted benzene ring; the "substituted or unsubstituted benzene ring" means that it is not substituted or is substituted by one or more substituents selected from the group consisting of: deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl; The c is selected from 1, 2, 3, 4, 5, 6 or 7; when there are two or more R3s, the two or more R3s are the same or different from each other, or adjacent R3s are connected to each other to form a substituted or unsubstituted benzene ring; the "substituted or unsubstituted benzene ring" means that it is not substituted or is substituted by one or more substituents selected from the group consisting of: deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl; The L0 is selected from a single bond or any of the structures shown below. The L1 and L2, whether identical or different, are selected from single bonds or any of the structures shown below. The same or different R5s are selected from any one of hydrogen, deuterium, fluorine, cyano, substituted or unsubstituted C1-C6 alkyl groups; the "substituted or unsubstituted C1-C6 alkyl group" means that it is not substituted or is substituted by one or more substituents selected from the group consisting of: deuterium, fluorine; The n1 that is the same or different is selected from 1, 2, 3 or 4; the n2 that is the same or different is selected from 1, 2, 3, 4, 5 or 6; the n3 that is the same or different is selected from 1, 2, 3, 4, 5, 6, 7 or 8; the n4 that is the same or different is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; when there are two or more R5, the two or more R5 are the same or different from each other.

4. A carbazole compound, characterized in that, The carbazole compounds have the structure shown in Formula 1. The x and z that are the same or different are selected from CH or N; among the four x in each ring, at most one is selected from N; among the four z in each ring, at most one is selected from N. The Choose any one of the structures shown below. The Ra is selected from any one of fluorine, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraceneyl, and substituted or unsubstituted phenanthryl. When Ra is a substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, or substituted or unsubstituted adamantyl, the substituent is selected from any one of deuterium, fluorine, methyl, or deuterated methyl. When two or more substituents are present, the two or more substituents are the same as or different from each other. When Ra is a substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraceneyl, or substituted or unsubstituted phenanthryl, the substituent is selected from any one of deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, deuterated methyl, deuterated isopropyl, deuterated tert-butyl, trifluoromethyl, or phenyl. When two or more substituents are present, the two or more substituents are the same as or different from each other. The Ar1 and Ar2, whether identical or different, are selected from any of the structures shown below. The Rb and Rc that are the same or different are selected from any one of substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, and substituted or unsubstituted naphthyl. When Rb and Rc are substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, or substituted or unsubstituted tert-butyl, the substituent is selected from deuterium and fluorine. When two or more substituents are present, the two or more substituents are the same as or different from each other. When Rb and Rc are substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or substituted or unsubstituted naphthyl, the substituent is selected from deuterium, fluorine, methyl, ethyl, isopropyl, tert-butyl, deuterated methyl, deuterated isopropyl, deuterated tert-butyl, or trifluoromethyl. When two or more substituents are present, the two or more substituents are the same as or different from each other. The m 11 The m4 is selected from 7; the m4 is selected from 1, 2, 3, 4 or 5; the m 41 Selected from 5; the m 42 The m5 is selected from 4; the m5 is selected from 1, 2, 3 or 4; the m 51 The m6 is selected from 4; the m6 is selected from 1, 2, 3, 4, 5, 6, 7 or 8; The same R2 is selected from deuterium; The R3 is the same as or different from any one of hydrogen, deuterium, fluorine, cyano, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted fluorenyl; the "substituted or unsubstituted" in "substituted or unsubstituted C1-C6 alkyl" means unsubstituted or substituted by one or more substituents selected from the group consisting of: deuterium, fluorine; the "substituted or unsubstituted" in "substituted or unsubstituted fluorenyl" means unsubstituted or substituted by one or more substituents selected from the group consisting of: deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, phenyl; b is selected from 6; The c is selected from 1, 2, 3, 4, 5, 6 or 7; when there are two or more R3s, the two or more R3s are the same or different from each other, or adjacent R3s are connected to each other to form a substituted or unsubstituted benzene ring; the "substituted or unsubstituted benzene ring" means that it is not substituted or is substituted by one or more substituents selected from the group consisting of: deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl; The L0 is selected from a single bond or any of the structures shown below. The L1 and L2, whether identical or different, are selected from single bonds or any of the structures shown below. The same or different R5s are selected from any one of hydrogen, deuterium, fluorine, cyano, substituted or unsubstituted C1-C6 alkyl groups; the "substituted or unsubstituted C1-C6 alkyl group" means that it is not substituted or is substituted by one or more substituents selected from the group consisting of: deuterium, fluorine; The n1 that is the same or different is selected from 1, 2, 3 or 4; the n2 that is the same or different is selected from 1, 2, 3, 4, 5 or 6; the n3 that is the same or different is selected from 1, 2, 3, 4, 5, 6, 7 or 8; the n4 that is the same or different is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; when there are two or more R5, the two or more R5 are the same or different from each other.

5. A carbazole compound, characterized in that, The carbazole compounds have the structure shown in Formula 1. The x and z that are the same or different are selected from CH or N; among the four x in each ring, at most one is selected from N; among the four z in each ring, at most one is selected from N. The Choose any one of the structures shown below. The Ra is selected from any one of fluorine, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraceneyl, and substituted or unsubstituted phenanthryl. When Ra is a substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, or substituted or unsubstituted adamantyl, the substituent is selected from any one of deuterium, fluorine, methyl, or deuterated methyl. When two or more substituents are present, the two or more substituents are the same as or different from each other. When Ra is a substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraceneyl, or substituted or unsubstituted phenanthryl, the substituent is selected from any one of deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, deuterated methyl, deuterated isopropyl, deuterated tert-butyl, trifluoromethyl, or phenyl. When two or more substituents are present, the two or more substituents are the same as or different from each other. The Ar1 and Ar2, whether identical or different, are selected from any of the structures shown below. The Rb and Rc that are the same or different are selected from any one of substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, and substituted or unsubstituted naphthyl. When Rb and Rc are substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, or substituted or unsubstituted tert-butyl, the substituent is selected from deuterium and fluorine. When two or more substituents are present, the two or more substituents are the same as or different from each other. When Rb and Rc are substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or substituted or unsubstituted naphthyl, the substituent is selected from deuterium, fluorine, methyl, ethyl, isopropyl, tert-butyl, deuterated methyl, deuterated isopropyl, deuterated tert-butyl, or trifluoromethyl. When two or more substituents are present, the two or more substituents are the same as or different from each other. The m 11 The m4 is selected from 7; the m4 is selected from 1, 2, 3, 4 or 5; the m 41 Selected from 5; the m 42 The m5 is selected from 4; the m5 is selected from 1, 2, 3 or 4; the m 51 The m6 is selected from 4; the m6 is selected from 1, 2, 3, 4, 5, 6, 7 or 8; The R2s, whether identical or different, are selected from any one of hydrogen, deuterium, fluorine, cyano, substituted or unsubstituted C1-C6 alkyl, or substituted or unsubstituted fluorenyl; the "substituted or unsubstituted" in "substituted or unsubstituted C1-C6 alkyl" means unsubstituted or substituted by one or more substituents selected from the group consisting of: deuterium, fluorine; the "substituted or unsubstituted" in "substituted or unsubstituted fluorenyl" means unsubstituted or substituted by one or more substituents selected from the group consisting of: deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, phenyl; The R3 is the same as that selected from deuterium; The b is selected from 1, 2, 3, 4, 5 or 6; when there are two or more R2s, the two or more R2s are the same or different from each other, or adjacent R2s are connected to each other to form a substituted or unsubstituted benzene ring; the "substituted or unsubstituted benzene ring" means that it is not substituted or is substituted by one or more substituents selected from the group consisting of: deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl; The c is selected from 7; The L0 is selected from a single bond or any of the structures shown below. The L1 and L2, whether identical or different, are selected from single bonds or any of the structures shown below. The same or different R5s are selected from any one of hydrogen, deuterium, fluorine, cyano, substituted or unsubstituted C1-C6 alkyl groups; the "substituted or unsubstituted C1-C6 alkyl group" means that it is not substituted or is substituted by one or more substituents selected from the group consisting of: deuterium, fluorine; The n1 that is the same or different is selected from 1, 2, 3 or 4; the n2 that is the same or different is selected from 1, 2, 3, 4, 5 or 6; the n3 that is the same or different is selected from 1, 2, 3, 4, 5, 6, 7 or 8; the n4 that is the same or different is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; when there are two or more R5, the two or more R5 are the same or different from each other.

6. A carbazole compound according to any one of claims 2-5, characterized in that, The Choose any one of the structures shown below. The Ra is selected from any one of substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, and substituted or unsubstituted phenanthryl. When Ra is a substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, or substituted or unsubstituted adamantyl, the substituent is selected from deuterium; when Ra is a substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, or substituted or unsubstituted phenanthryl, the substituent is selected from any one of deuterium, methyl, ethyl, isopropyl, tert-butyl, deuterated methyl, deuterated isopropyl, or deuterated tert-butyl, and when two or more substituents are present, the two or more substituents may be the same as or different from each other.

7. A carbazole compound according to any one of claims 1, 4, and 5, characterized in that, The Ar1 and Ar2, whether identical or different, are selected from any of the structures shown below. The Rb and Rc that are the same or different are selected from any one of substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, and substituted or unsubstituted naphthyl. When Rb and Rc are substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, or substituted or unsubstituted tert-butyl, the substituent is selected from deuterium; when Rb and Rc are substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or substituted or unsubstituted naphthyl, the substituent is selected from any one of deuterium, methyl, ethyl, isopropyl, tert-butyl, deuterated methyl, deuterated isopropyl, or deuterated tert-butyl, and when two or more substituents are present, the two or more substituents are the same as or different from each other.

8. A carbazole compound according to any one of claims 1-5, characterized in that, The L0 is selected from a single bond or any of the structures shown below. The same or different R5s are selected from any one of hydrogen, deuterium, substituted or unsubstituted C1 to C6 alkyl groups; "substituted or unsubstituted" means unsubstituted or substituted by one or more substituents selected from the group consisting of: deuterium.

9. A carbazole compound, characterized in that, The carbazole compounds are selected from any one of the structures shown below. 。 10. An organic electroluminescent device, comprising an anode, an organic layer, and a cathode, characterized in that, The organic layer comprises one or a combination of at least two of the carbazole compounds as described in any one of claims 1 to 9.

11. An organic electroluminescent device according to claim 10, characterized in that, The organic layer includes a light-emitting layer, which comprises one or a combination of at least two of the carbazole compounds according to any one of claims 1 to 9.

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