Carbazole compound and organic electroluminescent device thereof

Abstract

The invention provides a carbazole compound and an organic electroluminescent device thereof, and particularly relates to the technical field of organic photoelectric materials. The compound provided by the invention has good refractive index and thermal stability when being used as a covering layer material, can reduce the loss of light reflected by a nearby electrode during luminescence, effectively improves the stability of a film layer, effectively prolongs the service life of a device, and improves the luminous efficiency of the device. The preparation method of the compound is simple, raw materials are easy to obtain, and the compound can be widely applied to the fields of organic thin film transistors, panel display and the like and has good application effects and industrialization prospects.

Description

Technical Field

[0001] This invention relates to the field of organic optoelectronic materials technology, specifically to a carbazole compound and its organic electroluminescent device. Background Technology

[0002] Organic light-emitting diodes (OLEDs) are light-emitting devices that directly convert electrical energy into light energy based on organic optoelectronic materials. Compared with traditional display technologies such as liquid crystal displays (LCDs), OLEDs have higher luminous efficiency, faster response speed, greater flexibility, and simpler manufacturing processes. They are expected to replace traditional liquid crystal displays and fluorescent lighting, and can be fully utilized in the field of electronic displays and lighting products, with a wider range of application and development prospects.

[0003] Organic light-emitting diodes (OLEDs) mainly consist of three parts: an anode, a cathode, and organic functional layers. These organic functional layers include a hole injection layer (HIL), a hole transport layer (HTL), an electron blocking layer (EBL), an emissive layer (EML), and a capping layer (CPL). Through the clear division of labor and synergistic cooperation among these functional layers, efficient carrier injection, directional transport, and precise recombination are achieved, significantly improving the luminous efficiency and operational stability of the device. The light-emitting principle of OLEDs involves applying voltage to the two electrodes, injecting electrons and holes from the cathode and anode into the emissive layer, respectively. The recombination of these electrons and holes generates excitons, which then undergo radiative transitions to achieve light emission. The capping layer material needs to possess advantages such as suitable refractive index and thickness. However, due to the physicochemical properties of organic semiconductor materials, OLED devices suffer from problems such as low luminous efficiency, reduced resolution, and increased driving voltage, hindering the optimization and development of OLEDs.

[0004] Therefore, to solve the above problems, OLED materials need further improvement and refinement. Developing new and efficient capping layer materials to improve the performance of OLED devices is crucial. Summary of the Invention

[0005] To address the aforementioned problems, the present invention aims to provide a carbazole compound and its organic electroluminescent device, which can improve the luminous efficiency of the organic electroluminescent device and extend its service life.

[0006] This invention provides a carbazole compound, wherein the carbazole compound is selected from the structure represented by formula I:

[0007] Wherein, Ar1 is selected from either formula I-1 or I-2;

[0008] The i is independently selected from C(R) i Any one of N, wherein when i is bonded to other groups, i is selected from C atoms; The Y is independently selected from S, N(R) s Any one of the following; The R i R1, R2, R a R b Independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl, or two adjacent R i They connect with each other to form substituted or unsubstituted rings; The R s It is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl; a1 is selected from 0, 1, 2, or 3; when there are two or more R... a At that time, two or more R a The same or different between each other, or two adjacent R a They connect with each other to form substituted or unsubstituted rings; b1 is selected from 0, 1, 2, or 3; when there are two or more R b At that time, two or more R b They are the same as or different from each other; The Ar2 is selected from formula II;

[0009] X is selected from O, S, N(R) h Any one of the following; The v is independently selected from any one of CH and N atoms; when v is bonded to other groups, the v is selected from C atoms. The R cIndependently selected from hydrogen, deuterium, fluorine, trifluoromethyl, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, 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 groups, substituted or unsubstituted C1-C25 heterocyclic alkanes and C6-C30 aromatic ring fused cycloyl groups, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl groups, pyridine The following are all groups: pyrimidinyl, pyrazinyl, pyridazinyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thiophenyl, benzothiophenyl, dibenzothiophenyl, benzodibenzothiophenyl, pyrroleyl, indolyl, carbazoyl, oxazolyl, benzooxazolyl, dibenzooxazolyl, thiazoyl, benzothiazoyl, dibenzothiazoyl, imidazoyl, benzoimidazoyl, dibenzoimidazoyl, quinolinyl, benzoquinolinyl, isoquinolinyl, benzoisoquinolinyl, quinazolinyl, benzoquinazolinyl, quinoxolinyl, benzoquinoxolinyl, quinoxolinyl, benzoquinoxolinyl, phenantholinyl, naphridyl, acridineyl, phenoxazinyl, phenothiazinyl; The R h It is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl; The c1 is selected from 0, 1, 2, 3, or 4; when there are two or more R... c At that time, two or more R c The same or different between each other, or two adjacent R c They connect with each other to form substituted or unsubstituted rings; The Ar3 is independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl; L1, L2, and L3 are independently selected from any one of the following: single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C6-C30 heteroarylene, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl groups, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroarylene ring fused cycloyl groups, wherein the "substituted" group in "substituted or unsubstituted" is selected from deuterium, fluorine, trifluoromethyl, cyano, nitro, silyl, C1-C25 alkyl, C3-C25 cycloalkyl, C1-C25 heterocyclic alkyl, C6-C30 aryl, C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl groups, C1-C25 heterocyclic alkanes, and... Fused cyclic groups of aromatic rings (C6-C30), alicyclic and heterocyclic groups (C3-C25), pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thiophene, benzothiophene, dibenzothiophene, benzodibenzothiophene, pyrroleyl, indolyl, carbazoleyl. Any one of the following: oxazolyl, benzoxazolyl, dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzoimidazolyl, dibenzoimidazolyl, quinolinyl, benzoquinolinyl, isoquinolinyl, benzoisoquinolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenantholinyl, naphridinyl, acridineyl, phenoxazinyl, phenthiazinyl.

[0010] The present invention also provides an organic electroluminescent device, comprising an anode, a cathode, and an organic layer, wherein the organic layer is located between the anode and the cathode or on the side of the cathode away from the anode, and the organic layer comprises at least one of the carbazole compounds described in the present invention.

[0011] Beneficial effects

[0012] This invention provides a carbazole compound that, when used as a capping material, exhibits excellent refractive index and thermal stability. This reduces light loss due to reflection from nearby electrodes during luminescence, effectively improving film stability, extending device lifespan, and increasing luminous efficiency. The compound provided by this invention has a simple preparation method, readily available raw materials, and meets industrial requirements, demonstrating promising prospects for industrialization. Attached Figure Description

[0013] Figure 1 This is the HPLC chromatogram of compound 65. Detailed Implementation

[0014] The technical solutions of the present invention will be clearly and completely described below with reference to the embodiments of the present invention. Obviously, the described embodiments are only some embodiments of the present invention, and not all embodiments. After reading the present invention, any modifications of the present invention in various equivalent forms by those skilled in the art fall within the scope defined by the present invention.

[0015] In this specification, " "This refers to the portion that is connected to another substituent." "It can be attached to any optional position of the attached group / fragment."

[0016] 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 ring. For example, Can represent or ; Can represent , , And so on.

[0017] In this specification, when the position of a substituent or linking site on the ring is not fixed, it means that it can be linked to any of the optional sites on the ring.

[0018] For example, Can represent , , ; Can represent , , ; Can represent , , , , , , , , , .

[0019] And so on.

[0020] The substituents described in the "substituted or unsubstituted" of this invention may be independently selected from deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcohols of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C1-C6 alkylthio, substituted or unsubstituted C1-C12 alkylamine, substituted or unsubstituted C6-C30 aryloxy, etc., but are not limited thereto, or adjacent substituents may be linked to form a ring. Preferred compounds include deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl groups, C1-C25 alkyl groups, C3-C25 cycloalkyl groups, C6-C30 aryl groups, C2-C30 heteroaryl groups, C3-C30 alicyclic and C6-C30 fused cycloyl groups, and C1-C12 alkoxy groups. Specific examples may include deuterium, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, propyl, butyl, cyclopropyl, cyclohexyl, adamantyl, norbornel, phenyl, tolyl, mesitylene, pentadeuterated phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, perylene, phenylene, acenaphthene, fluoranyl, pyrene, fluoranyl, indene, dihydroindene, dihydronaphthyl, and tetrahydronaphthyl. The following are listed: 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, spirodifluorenyl, carbazolyl, 9-phenylcarbazolyl, carbazo-indolyl, pyrrololyl, furanyl, thiophene, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, pyridinyl, pyrimidinyl, pyrazinyl, pyrazinyl, triazinyl, oxazolyl, thiazolyl, imidazolyl, benzooxazolyl, benzothiazolyl, benzotriazolyl, benzoimidazolyl, quinolinyl, isoquinolinyl, quinoxolinyl, quinazolinyl, phenothiazinyl, phenothiazinyl, acridineyl, benzocyclobutyl, benzocyclobutenyl, benzocyclopentyl, benzocyclopentenyl, benzocyclohexyl, benzocyclohexenyl, etc., but not limited to these. Or, when there are multiple substituents, the multiple substituents may be the same or different from each other; or adjacent substituents may be connected to form a ring.

[0021] The "substituted or unsubstituted silyl group" mentioned in this invention refers to -Si(R k )3 groups, wherein each R kThe same or different from any one selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl.

[0022] Examples of halogen atoms described in this invention may include fluorine, chlorine, bromine, and iodine.

[0023] The aryl group described in this invention refers to a monovalent group formed by removing a hydrogen atom from the aromatic carbon atom of an aromatic compound molecule. It can be a monocyclic aryl group or a fused-ring aryl group, preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 15 carbon atoms, and most preferably 6 to 12 carbon atoms. Examples of aryl groups include, but are not limited to, phenyl, biphenyl, terphenyl, tetraphenyl, pentaphenyl, naphthyl, phenanthryl, anthraceneyl, fluorenyl, pyrene, triphenylene, fluoranthyl, benzo[a]fluorenyl, spirodifluorenyl, benzo[a]fluoranthyl, trefoilyl, etc.

[0024] The heteroaryl group described in this invention refers to a group formed by replacing one or more aromatic carbon atoms in an aryl group with heteroatoms. It can be a monocyclic heteroaryl or a fused-ring heteroaryl. The heteroatoms include, but are not limited to, oxygen, sulfur, nitrogen, silicon, and phosphorus atoms. Preferably, it has 2 to 30 carbon atoms, more preferably 2 to 18 carbon atoms, particularly preferably 2 to 15 carbon atoms, and most preferably 2 to 12 carbon atoms. These include, but are not limited to, pyridinyl, triazinyl, furanyl, thiopheneyl, pyrroleyl, imidazolyl, oxazolyl, thiazolyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzodibenzofuranyl, benzodibenzothiopheneyl, carbazolyl, benzocarbazolyl, acridineyl, phenoxazinyl, phenthiazinyl, phenoxthiazinyl, quinazolinyl, quinoxolinyl, quinolinyl, indolyl, azacarbazolyl, azafluorenyl, azaspirodifluorenyl, oxanthracenel, and thioxanthracenel.

[0025] The arylene group described in this invention can be a monocyclic arylene, a polycyclic arylene, or a fused-ring arylene. An arylene refers to a divalent group formed by removing two hydrogen atoms from the aromatic nucleus of an aromatic hydrocarbon molecule. It preferably has 6 to 30 carbon atoms, more preferably 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 18 carbon atoms, and most preferably 6 to 12 carbon atoms. Examples include phenylene, biphenylene, terphenylene, naphthylene, anthracene, phenanthrene, tricrene, pyrene, perylene, phenanthrene, acenaphthene, fluorene, phenyl fluorene, dibenzo[a]fluorene, spirodifluorene, benzo[a]spirodifluorene, fluorene anthracene, etc., but are not limited thereto.

[0026] The heteroaryl group described in this invention refers to a group formed by replacing one or more aromatic carbon atoms in the aryl group with heteroatoms, including but not limited to O, S, N, Si, or P atoms. Preferably, it has 2 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 15 carbon atoms. Examples include, but are not limited to, pyridinyl, pyrimidinyl, triazineyl, furanyl, thiopheneyl, carbazolyl, benzofuranyl, benzothiopheneyl, benzocarbazolyl, dibenzofuranyl, dibenzothiopheneyl, dibenzocarbazolyl, benzodibenzofuranyl, benzodibenzothiopheneyl, isoquinolinyl, bipyridinyl, bipyrimidinyl, phenylpyridinyl, phenylpyrimidinyl, etc.

[0027] The fused alicyclic and aromatic ring group described in this invention refers to a monovalent group formed by removing one hydrogen atom after the alicyclic and aromatic rings are fused together. Preferably, it has 7 to 30 carbon atoms, more preferably 7 to 18 carbon atoms, and most preferably 7 to 13 carbon atoms. Examples include benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, naphthocyclopropyl, naphthocyclobutyl, naphthocyclopentyl, naphthocyclohexyl, etc., but are not limited thereto.

[0028] The fused cyclic group of heterocyclic alkanes and aromatic rings described in this invention refers to the monovalent group formed by removing one hydrogen atom after a heterocyclic alkanes and aromatic rings are fused together. Preferably, it has 6 to 30 carbon atoms, more preferably 7 to 18 carbon atoms, and most preferably 7 to 13 carbon atoms. Examples include benzo[a]tetrahydropyrrole, naphtho[a]tetrahydropyrrole, phenanthrene[a]tetrahydropyrrole, benzo[a]hexacyclic butyl, benzo[a]hexacyclic heptyl, benzo[a]piperidinyl, naphtho[a]piperidinyl, phenanthrene[a]piperidinyl, etc., but are not limited thereto.

[0029] The fused cyclic group of alicyclic and heteroaromatic rings mentioned in this invention refers to a monovalent group formed by removing a hydrogen atom after the alicyclic and heteroaromatic rings are fused together. Preferably, it has 5 to 30 carbon atoms, more preferably 5 to 18 carbon atoms, and most preferably 5 to 12 carbon atoms. Examples include, but not limited to, dibenzofuranocyclopropyl, dibenzofuranocyclobutyl, dibenzofuranocyclopentyl, dibenzofuranocyclohexyl, dibenzofuranocycloheptyl, dibenzothiophenecyclopropyl, dibenzothiophenecyclobutyl, dibenzothiophenecyclopentyl, dibenzothiophenecyclohexyl, dibenzothiophenecycloheptyl, carbazocyclopropyl, carbazocyclobutyl, carbazocyclopentyl, carbazocyclohexyl, carbazocycloheptyl, pyridinocyclopropyl, pyridinocyclobutyl, pyridinocyclopentyl, pyridinocyclohexyl, pyridinobenzocycloheptyl, pyrimidinocyclopropyl, pyrimidinocyclobutyl, pyrimidinocyclopentyl, pyrimidinocyclohexyl, pyrimidinobenzocycloheptyl, etc.

[0030] The alicyclic and aromatic ring fused cyclic groups described in this invention refer to the divalent groups formed by removing two hydrogen atoms after the alicyclic and aromatic rings are fused together. Preferably, they have 7 to 30 carbon atoms, more preferably 7 to 18 carbon atoms, and most preferably 7 to 13 carbon atoms. Examples include, but are not limited to, benzo[a]cyclopropyl, benzo[a]cyclobutyl, benzo[a]cyclopentyl, benzo[a]cyclohexyl, benzo[a]cycloheptyl, naphtho[a]cyclopropyl, naphtho[a]cyclobutyl, naphtho[a]cyclopentyl, and naphtho[a]cyclohexyl.

[0031] The fused alicyclic and heteroaromatic ring cyclic groups described in this invention refer to the divalent groups formed by removing two hydrogen atoms after the alicyclic and heteroaromatic rings are fused together. Preferably, they have 5 to 30 carbon atoms, more preferably 5 to 18 carbon atoms, and most preferably 5 to 12 carbon atoms. Examples include dibenzofuranocyclopropyl, dibenzofuranocyclobutyl, dibenzofuranocyclopentyl, dibenzofuranocyclohexyl, dibenzofuranocycloheptyl, dibenzothiophenocyclopropyl, dibenzothiophenocyclobutyl, dibenzothiophenocyclopentyl, and dibenzothiophenocyclohexyl. Dibenzothiophene-cycloheptyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, pyridinyl-cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, benzophenyl-cycloheptyl, pyrimidinyl-cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, benzophenyl-cycloheptyl, pyrimidinyl-cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, benzophenyl-cycloheptyl, etc., but not limited to these.

[0032] The alkyl group described in this invention refers to a monovalent group formed by removing one hydrogen atom from an alkane molecule, preferably having 1 to 25 carbon atoms, more preferably having 1 to 12 carbon atoms, more preferably having 1 to 8 carbon atoms, and particularly preferably having 1 to 6 carbon atoms. This includes, but is not limited to, methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, isopropyl, isobutyl, sec-butyl, tert-butyl, etc.

[0033] The cycloalkyl group described in this invention refers to a monovalent group formed by removing one hydrogen atom from a cyclic alkane molecule, preferably having 3 to 25 carbon atoms, more preferably 3 to 12 carbon atoms, particularly preferably 5 to 10 carbon atoms, and most preferably 5 to 7 carbon atoms. Examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, camphenyl, etc., but are not limited thereto.

[0034] The heterocyclic alkyl group described in this invention refers to a group formed by removing one hydrogen atom from a heterocyclic molecule in which the atoms constituting the ring contain at least one heteroatom in addition to carbon atoms. The heteroatom includes, but is not limited to, O, S, N, Si, or P atoms, and preferably has 1 to 25 carbon atoms, more preferably 1 to 15 carbon atoms, more preferably 2 to 12 carbon atoms, and particularly preferably 2 to 6 carbon atoms. Examples include piperidinyl, piperazineyl, tetrahydropyrrolyl, ethylene oxide, cyclothioethylene, propylenediyl, morpholinyl, thiomorpholinyl, etc., but are not limited thereto.

[0035] The "linked ring formation" described in this invention refers to two groups being linked together by chemical bonds and optionally undergoing aromatization. Examples are shown below:

[0036] In this invention, the ring formed by the connection can be an aromatic ring system, an aliphatic ring system, or a ring system formed by the fusion of the two. The ring formed by the connection can be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring, or a fused ring, such as benzene, naphthalene, indene, cyclopentene, cyclopentane, cyclopentanophenene, cyclohexene, cyclohexane, cyclohexanophenene, quinoline, isoquinoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, phenanthrene, or pyrene, but is not limited thereto.

[0037] In this invention, "at least one" includes one, two, three, four, or more. "Two or more" may include two, three, four, or more, where permissible.

[0038] This invention provides a carbazole compound, wherein the carbazole compound is selected from the structure represented by formula I:

[0039] Wherein, Ar1 is selected from either formula I-1 or I-2;

[0040] The i is independently selected from C(R) i Any one of N, wherein when i is bonded to other groups, i is selected from C atoms; The Y is independently selected from S, N(R) s Any one of the following; The R i R1, R2, R a R b Independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl, or two adjacent R i They connect with each other to form substituted or unsubstituted rings; The R s It is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl; a1 is selected from 0, 1, 2, or 3; when there are two or more R... a At that time, two or more R a The same or different between each other, or two adjacent R a They connect with each other to form substituted or unsubstituted rings; b1 is selected from 0, 1, 2, or 3; when there are two or more R b At that time, two or more R b They are the same as or different from each other; The Ar2 is selected from formula II;

[0041] X is selected from O, S, N(R) h Any one of the following; The v is independently selected from any one of CH and N atoms; when v is bonded to other groups, the v is selected from C atoms. The R c Independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, 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 groups, substituted or unsubstituted C1-C25 heterocyclic alkanes and C6-C30 aromatic ring fused cycloyl groups, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl groups, pyridine The following are all groups: pyrimidinyl, pyrazinyl, pyridazinyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thiophenyl, benzothiophenyl, dibenzothiophenyl, benzodibenzothiophenyl, pyrroleyl, indolyl, carbazoyl, oxazolyl, benzooxazolyl, dibenzooxazolyl, thiazoyl, benzothiazoyl, dibenzothiazoyl, imidazoyl, benzoimidazoyl, dibenzoimidazoyl, quinolinyl, benzoquinolinyl, isoquinolinyl, benzoisoquinolinyl, quinazolinyl, benzoquinazolinyl, quinoxolinyl, benzoquinoxolinyl, quinoxolinyl, benzoquinoxolinyl, phenantholinyl, naphridyl, acridineyl, phenoxazinyl, phenothiazinyl; The R h It is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl; The c1 is selected from 0, 1, 2, 3, or 4; when there are two or more R... c At that time, two or more R c The same or different between each other, or two adjacent R c They connect with each other to form substituted or unsubstituted rings; The Ar3 is independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl; L1, L2, and L3 are independently selected from any one of the following: single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C6-C30 heteroarylene, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl groups, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroarylene ring fused cycloyl groups, wherein the "substituted" group in "substituted or unsubstituted" is selected from deuterium, fluorine, trifluoromethyl, cyano, nitro, silyl, C1-C25 alkyl, C3-C25 cycloalkyl, C1-C25 heterocyclic alkyl, C6-C30 aryl, C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl groups, C1-C25 heterocyclic alkanes, and... Fused cyclic groups of aromatic rings (C6-C30), alicyclic and heterocyclic groups (C3-C25), pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thiophene, benzothiophene, dibenzothiophene, benzodibenzothiophene, pyrroleyl, indolyl, carbazoleyl. Any one of the following: oxazolyl, benzoxazolyl, dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzoimidazolyl, dibenzoimidazolyl, quinolinyl, benzoquinolinyl, isoquinolinyl, benzoisoquinolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenantholinyl, naphridinyl, acridineyl, phenoxazinyl, phenthiazinyl.

[0042] Preferably, the Selected from any one of the following groups:

[0043] The z is independently selected from C(R) z Z can be any one of N, and when z is bonded to other groups, z is selected from C atoms; Z1 is selected from O, S, N(R) h Any one of the following; Z2 is independently selected from O, S, C(R) u R v ), N(R h Any one of the following; The R z R u R vIt is independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl; The R h It is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl.

[0044] Preferably, in each six-membered ring containing z, at most two or at most one z are selected from N.

[0045] Preferably, z is independently selected from C(R) z ).

[0046] Preferably, when When selected from any of the following groups:

[0047] The Ar3 is selected from hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted silyl group, substituted or unsubstituted C1-C25 alkyl group, substituted or unsubstituted C3-C25 cycloalkyl group, substituted or unsubstituted C1-C25 heterocyclic alkyl group, and L3 is selected from single bond.

[0048] Preferably, the Ar1 is selected from any one of the following groups:

[0049] The R1, R2, R a R bThe group independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, or substituted or unsubstituted groups, including: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl. Benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthraceneyl, phenanthrene, pyrene, perylene, phenylene, acenaphthene, fluoranyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thiopheneyl, benzothiopheneyl, dibenzothiopheneyl, benzodibenzothiopheneyl, pyridyl Any one of the following: pyrrolyl, indolyl, carbazolyl, oxazolyl, benzoxazolyl, dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzoimidazolyl, dibenzoimidazolyl, quinolinyl, benzoquinolinyl, isoquinolinyl, benzoisoquinolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenantholinyl, naphridyl, acridineyl, phenoxazinyl, phenothiazinyl; The R s The following groups are independently selected from hydrogen, deuterium, substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl The following are all of the following: silyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthraceneyl, phenanthrene, pyrene, peryl, phenyl, acenaphthene, fluoranyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl; a1 is selected from 0, 1, 2, or 3; a2 is selected from 0, 1, 2, 3, 4, or 5; a3 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; a4 is selected from 0, 1, 2, 3, or 4; a5 is selected from 0, 1, 2, 3, 4, 5, or 6; when there are two or more R... a At that time, two or more R a The same or different between each other, or two adjacent R a They connect with each other to form substituted or unsubstituted rings; b1 is selected from 0, 1, 2, or 3; when there are two or more R b At that time, two or more R b They may be the same as or different from each other.

[0050] More preferably, the Ar1 is selected from any one of the following groups: .

[0051] Preferably, the Ar2 group is selected from any one of the following groups:

[0052] The R cThe group independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, nitro, or substituted or unsubstituted groups, including: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl. Benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthraceneyl, phenanthrene, pyrene, perylene, phenylene, acenaphthene, fluoranyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thiopheneyl, benzothiopheneyl, dibenzothiopheneyl, benzodibenzothiopheneyl, pyrroleyl Any one of the following: indolyl, carbazolyl, oxazolyl, benzoxazolyl, dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzoimidazolyl, dibenzoimidazolyl, quinolinyl, benzoquinolinyl, isoquinolinyl, benzoisoquinolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenantholinyl, naphridyl, acridineyl, phenoxazinyl, phenothiazinyl; The R h The following groups are independently selected from hydrogen, deuterium, substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl The following are all of the following: silyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthraceneyl, phenanthrene, pyrene, peryl, phenyl, acenaphthene, fluoranyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl; c1 is selected from 0, 1, 2, 3, or 4; c2 is selected from 0, 1, 2, or 3; c3 is selected from 0, 1, or 2; c4 is selected from 0, 1, 2, 3, 4, 5, or 6; c5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; when there are two or more R... c At that time, two or more R c The same or different between each other, or two adjacent R c They connect with each other to form substituted or unsubstituted rings.

[0053] More preferably, the Ar2 is selected from any one of the following groups: .

[0054] Preferably, the Ar3 is selected from hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted silyl group, substituted or unsubstituted C1-C25 alkyl group, substituted or unsubstituted C3-C25 cycloalkyl group, substituted or unsubstituted C1-C25 heterocycloalkyl group, and any one of the following groups:

[0055] The u is independently selected from any one of CH and N atoms; when u is bonded to other groups, the u is selected from C atoms. The ring A is selected from substituted or unsubstituted C3~C10 alicyclic rings; X1 and X2 are independently selected from O, S, and N(R). k Any one of the following; X3, X4, and X5 are independently selected from O, S, and C(R). p R q ), N(R k Any one of the following; The R d R d'Independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl; The R p R q Independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or R p R q The links between them form substituted or unsubstituted rings; The R k It is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl; The d1 is selected from 0, 1, 2, 3, 4, or 5; the d2 is selected from 0, 1, 2, 3, or 4; the d3 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; the d4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; the d5 is selected from 0, 1, or 2; the d6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; the d7 is selected from 0, 1, 2, or 3; the d8 is selected from 0, 1, 2, 3, 4, 5, or 6; when there are two or more R... d At that time, two or more R d The same or different between each other, or two adjacent R d They connect with each other to form substituted or unsubstituted rings; The d'1 is selected from 0, 1, or 2; when there are two or more R d At that time, two or more R d 'They are the same as or different from each other.'

[0056] More preferably, the Ar3 is selected from hydrogen, deuterium, fluorine, trifluoromethyl, nitro, and substituted or unsubstituted groups such as: methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, and any one of the following groups:

[0057] The R d R d '、R p R qThe group is independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, nitro, and substituted or unsubstituted groups of the following: methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl. Benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthraceneyl, phenanthrene, pyrene, perylene, phenylene, acenaphthene, fluoranyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thiopheneyl, benzothiopheneyl, dibenzothiopheneyl, benzodibenzothiopheneyl, pyrroleyl, indole Any one of the following: doloyl, carbazolyl, oxazolyl, benzoxazolyl, dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzoimidazolyl, dibenzoimidazolyl, quinolinyl, benzoquinolinyl, isoquinolinyl, benzoisoquinolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenantholinyl, naphridyl, acridineyl, phenoxazinyl, phenothiazinyl; The R k The following groups are independently selected from hydrogen, deuterium, substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenyl Any one of the following: silyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl; The d1 is selected from 0, 1, 2, 3, 4, or 5; the d2 is selected from 0, 1, 2, 3, or 4; the d3 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; the d4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; the d5 is selected from 0, 1, or 2; the d6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; the d7 is selected from 0, 1, 2, or 3; the d8 is selected from 0, 1, 2, 3, 4, 5, or 6; the d9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; when there are two or more R... c At that time, two or more R c The same or different between each other, or two adjacent R c They connect with each other to form substituted or unsubstituted rings; The d'1 is selected from 0, 1, or 2; the d'2 is selected from 0, 1, 2, 3, or 4; the d'3 is selected from 0, 1, 2, 3, 4, 5, or 6; the d'4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the d'5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; when there are two or more R... c At that time, two or more R c 'They are the same as or different from each other.'

[0058] More preferably, the Ar3 is selected from hydrogen, deuterium, fluorine, trifluoromethyl, nitro, methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, and any one of the following groups: .

[0059] Preferably, L1, L2, and L3 are independently selected from single bonds or any one of the following groups, or a combination of two or more of the following groups:

[0060] The r is independently selected from either C or N atoms, and when r is bonded to other groups, the r is selected from C atoms; Z1 and Z2 are independently selected from O, S, and N(R). t Any one of the following; Z3, Z4, and Z5 are independently selected from O, S, and C(R). i R j ), N(R t Any one of the following; The ring B is selected from substituted or unsubstituted C3~C10 alicyclic rings; The R e R e '、R i R j Independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, 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 groups, substituted or unsubstituted C1-C25 heterocyclic alkanes and C6-C30 aromatic ring fused cycloyl groups, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl groups, pyridyl, Pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thiophenyl, benzothiophenyl, dibenzothiophenyl, benzodibenzothiophenyl, pyrroleyl, indolyl, carbazoleyl, oxazolyl, benzooxazolyl, dibenzooxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzoimidazolyl, dibenzoimidazolyl, quinolinyl, benzoquinolinyl, isoquinolinyl, benzoisoquinolinyl, quinazolinyl, benzoquinazolinyl, quinoxolinyl, benzoquinoxolinyl, quinoxolinyl, benzoquinoxolinyl, phenantholinyl, naphridinyl, acridineyl, phenoxazinyl, phenothiazinyl, or R i R j The links between them form substituted or unsubstituted rings; The R t It is selected from any one of hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl; The number n is selected from 1, 2, 3, or 4; The value of e1 is selected from 0, 1, 2, 3, or 4; the value of e2 is selected from 0, 1, 2, 3, 4, 5, or 6; the value of e3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the value of e4 is selected from 0, 1, or 2; when there are two or more R... e At that time, two or more R e The same or different between each other, or two adjacent R e They connect with each other to form substituted or unsubstituted rings; The term e'1 is selected from 0, 1, or 2; when there are two or more R... e At that time, two or more R e 'They are the same as or different from each other.'

[0061] More preferably, L1, L2, and L3 are independently selected from single bonds or any one of the following groups, or a combination of two or more of the following groups:

[0062] The R e R e '、R i R jThe group is independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, and substituted or unsubstituted groups of the following: methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentene. Benzyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthraceneyl, phenanthrene, pyrene, perylene, phenylene, acenaphthene, fluoranyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thiopheneyl, benzothiopheneyl, dibenzothiopheneyl, benzodibenzothiopheneyl, pyrroleyl, Any one of the following: indolyl, carbazolyl, oxazolyl, benzoxazolyl, dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzoimidazolyl, dibenzoimidazolyl, quinolinyl, benzoquinolinyl, isoquinolinyl, benzoisoquinolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenantholinyl, naphridyl, acridineyl, phenoxazinyl, phenothiazinyl; The R t Selected from hydrogen, deuterium, and the following substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetramethylsilyl, etc. The following is a list of compounds: pyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthraceneyl, phenanthrene, pyrene, peryl, phenyl, acenaphthene, fluoranyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, and triazinyl. The value of e1 is selected from 0, 1, 2, 3, or 4; the value of e2 is selected from 0, 1, 2, 3, 4, 5, or 6; the value of e3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the value of e4 is selected from 0, 1, or 2; the value of e5 is selected from 0, 1, 2, or 3; the value of e6 is selected from 0, 1, 2, 3, 4, or 5; the value of e7 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; when there are two or more R... e At that time, two or more R e The same or different between each other, or two adjacent R e They connect with each other to form substituted or unsubstituted rings; The term e'1 is selected from 0, 1, or 2; the term e'2 is selected from 0, 1, 2, 3, or 4; the term e'3 is selected from 0, 1, 2, 3, 4, 5, or 6; the term e'4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the term e'5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; when there are two or more R... e At that time, two or more R e 'They are the same as or different from each other.'

[0063] More preferably, L1, L2, and L3 are independently selected from single bonds or any one of the following groups, or a combination of two or more of the following groups: .

[0064] Most preferably, formula I is selected from any of the following structures: .

[0065] The above lists some specific structural forms of carbazole compounds represented by chemical formula I according to the present invention. However, the present invention is not limited to these listed chemical structures. Any structure based on the structure shown in chemical formula I, with substituents as defined above, should be included.

[0066] The present invention provides an organic electroluminescent device, comprising an anode, a cathode, and an organic layer, wherein the organic layer is located between the anode and the cathode or on the side of the cathode away from the anode, and the organic layer comprises at least one of the carbazole compounds described in the present invention.

[0067] Preferably, the organic layer is located between the anode and the cathode, and the organic layer includes at least one of a hole transport region, a light-emitting layer, and an electron transport layer.

[0068] Preferably, the hole transport region includes at least one of a hole injection layer, a hole transport layer, and an electron blocking layer.

[0069] Preferably, the hole transport layer includes a first hole transport layer and a second hole transport layer, wherein the first hole transport layer is located between the anode and the light-emitting layer, and the second hole transport layer is located between the first hole transport layer and the light-emitting layer.

[0070] Preferably, the hole transport layer includes a first hole transport layer, a second hole transport layer, and a third hole transport layer, wherein the first hole transport layer is located between the anode and the light-emitting layer, the second hole transport layer is located between the first hole transport layer and the light-emitting layer, and the third hole transport layer is located between the second hole transport layer and the light-emitting layer.

[0071] Preferably, the light-emitting layer comprises a host material and a dopant material.

[0072] Preferably, the electron transport region comprises at least one of an electron injection layer, an electron transport layer, and a hole blocking layer.

[0073] Preferably, the organic layer is located on the side of the cathode opposite to the anode, and the organic layer includes a capping layer containing at least one of the carbazole compounds described in this invention.

[0074] The cathode of this invention is preferably made of a material with a low work function. The cathode materials of this invention include, but are not limited to, metals, metal alloys, conductive compounds, and mixtures thereof. Specific examples of the cathode materials include, but are not limited to, aluminum (Al), silver (Ag), gold (Au), lead (Pb), lithium (Li), magnesium (Mg), ytterbium (Yb), calcium (Ca), magnesium-silver alloy (Mg:Al), lithium-aluminum alloy (Li:Al), and calcium / silver (Ca / Ag).

[0075] The hole injection layer described in this invention is preferably made of a material with high hole injection capability. It may include triarylamine compounds, metal compounds, quinone derivatives, phthalocyanine derivatives, polymers, axialene compounds, and other substances with high hole injection capability. Specific examples include, but are not limited to, tetracyanoquinone dimethyl ether (TCNQ), 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanoquinone-dimethyl ether (F4-TCNQ), 4,4',4''-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4”-tris(N-3-methylphenyl-N-phenylamino)triphenylamine (m-MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N' [-phenylamino]phenyl}-N-phenylamino)biphenyl (DNTPD), molybdenum trioxide (MoO3), vanadium pentoxide (V2O5), tungsten trioxide (WO3), nickel oxide (NiO), titanium dioxide (TiO2), copper phthalocyanine (CuPc), titanium phthalocyanine (TiOPC), 4,4',4”-tris[2-naphthylphenylamino]triphenylamine (2T-NATA), 1,4,5,8,9,11-hexaazabenzonitrile (HAT-CN), poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS), etc.

[0076] The hole transport layer described in this invention is preferably made of a material with high hole transport properties. It may include aromatic amine derivatives, biphenyl diamine derivatives, carbazole derivatives, fluorene derivatives, stilbene derivatives, phthalocyanine compounds, anthraquinone compounds, quinacridone compounds, hexanitrile hexaazabenzophenanthrene compounds, polythiophene, polyaniline, polyvinylcarbazole, etc. Specific examples of hole transport materials include, but are not limited to, N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), N4,N4,N4',N4'-tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine, 4,4'-cyclohexylbis[N,N-di(4-methylphenyl)aniline] (TAPC), N,N'-diphenyl-N,N'-di(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), 2,2,7,7-tetra(diphenylamino)-9,9-spirodifluorene (Spiro-TAD), and 4,4',4”-tris(carbazole-9-yl)triphenylamine (TCTA), etc.

[0077] The electron blocking layer described in this invention is preferably made of a material with good hole transport capability and electron blocking capability. It may include aromatic amine derivatives, carbazole derivatives, etc. Specific examples may include N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB), etc., but are not limited thereto.

[0078] The luminescent layer of this invention may include a single material, a host material (also called a matrix material), and a dopant material (also called a guest material). The luminescent layer material may include multiple host materials and multiple dopant materials. The type of dopant material can be fluorescent, phosphorescent, or TADF. Fluorescent dopant materials may include: fused polycyclic aromatic derivatives, styrene-based amine derivatives, fused-ring amine derivatives, boron-containing compounds, pyrrole derivatives, indole derivatives, carbazole derivatives, etc., such as C545T, BCzVBi, DPAVBi, etc. Phosphorescent dopant materials may include: heavy metal complexes, phosphorescent rare-earth metal complexes, etc., such as FIrpic, Ir(ppy)3, Ir(ppy)2(acac), etc. The host material of the luminescent layer may include fused aromatic ring derivatives, heterocyclic compounds, etc. Fused aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentane derivatives, phenanthrene derivatives, fluoranthene derivatives, etc., as well as heterocyclic compounds including carbazole derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, pyrimidine derivatives, etc., such as Alq3, BAlq, TPBi, TPD, CBP, TCTA, ADN, etc., but not limited to these.

[0079] The electron injection layer described in this invention is preferably made of a material with high electron injection properties, including metals, metal salts, and metal oxides. The electron injection materials include, but are not limited to, lithium (Li), cesium (Cs), lithium fluoride (LiF), lithium oxide (Li₂O), cesium fluoride (CsF), magnesium phosphide (MgP), cesium carbonate (Cs₂CO₃), lithium oxide (Li₂O), lithium boron oxide (LiBO₂), aluminum oxide (Al₂O₃), and vanadium oxide (V₂O₅).

[0080] The electron transport layer described in this invention is preferably made of a material with high electron transport properties. Electron transport layer materials may include metal complexes, pyridine derivatives, imidazole derivatives, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, etc. The electron transport materials include, but are not limited to, tris(8-hydroxyquinoline)aluminum(III) (Alq3), 3,3'-[5'-[3-(3-pyridyl)phenyl](TmPyPB), 1,3,5-tris(N-phenyl-2-benzimidazole)benzene (TPBi), 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (PBD), 3-(biphenyl-4-yl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (TAZ), 4,7-diphenyl-1,10-phenanthroline (Bphen), bis(10-hydroxybenzo[h]quinoline)beryllium (BeBq2), and bis(2-methyl-8-hydroxyquinoline)(4-phenylphenol)aluminum(III) (BAlq), etc.

[0081] The hole-blocking layer described in this invention can typically be formed under the same conditions as the hole injection layer. It may include aluminum complexes, lithium complexes, beryllium complexes, oxazole derivatives, benzoxazole derivatives, thiazole derivatives, benzothiazole derivatives, imidazole derivatives, benzimidazole derivatives, phenanthrene derivatives, polymers, rare earth derivatives, triazine derivatives, quinoline derivatives, diazanphenanthrene derivatives, azirbenzene derivatives, anthrone derivatives, etc. Specific examples of the hole-blocking layer material include, but are not limited to, BCP, BAlq, TPBi, etc.

[0082] The anode material described in this invention is preferably a high work function material, including metals, alloys, conductive compounds, and mixtures thereof. It may include zinc (Zn), gold (Au), platinum (Pt), chromium (Cr), copper (Cu), palladium (Pd), titanium (Ti), and palladium (Pd), or alloys thereof; metal oxides may include zinc oxide (ZnO), indium oxide (InO), tin oxide (SnO2), indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides may include zinc oxide / aluminum (ZnO / Al), silver / indium tin oxide (Ag / ITO), and indium tin oxide / silver / indium tin oxide (ITO / Ag / ITO); conductive polymers may include poly[3,4-(ethylene-1,2-dioxothiophene)] (PEDOT), polypyrrole (PPY), and polyaniline (PANI), but are not limited thereto.

[0083] The capping material described in this invention is preferably a material with photocoupling properties. In addition to the carbazole compound provided in this invention, the capping material also includes imidazole derivatives, oxazole derivatives, thiazole derivatives, aromatic amine derivatives, etc. Specific examples of the capping material include, but are not limited to, tris(8-hydroxyquinoline)aluminum(III) (Alq3), N,N'-di(naphthyl-1-yl)-N,N'-di(phenyl)-2,2'-dimethylbenzidine (NPD), 4,4'-di(9-carbazole)biphenyl (CBP), N4,N4,N4',N4'-tetra(4-methoxyphenyl)-[1,1'-biphenyl]-4,4'-diamine (MeO-TPD), lithium fluoride, magnesium fluoride, etc. The carbazole compound of this invention is preferred.

[0084] The following is one method for preparing the compound represented by chemical formula I of this invention, but the preparation method of this invention is not limited thereto. The core structure of the compound of chemical formula I can be prepared by the reaction route shown below. 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.

[0085] [Synthesis Route]

[0086] Preparation of compound I: or

[0087] Xa, Xb, Xc, Xd, and Xe are each independently selected from any one of Cl, Br, and I; the limitations of Ar1, Ar2, Ar3, L1, L2, L3, and i are the same as those described above.

[0088] Description of raw materials, reagents, and characterization equipment: 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 using preparation methods well known to those skilled in the art.

[0089] Mass spectrometry was performed using a Waters G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer, with chloroform as the solvent. Elemental analysis was performed using a VarioELcube organic elemental analyzer from Elementar GmbH, Germany, with sample masses ranging from 5 to 10 mg.

[0090] Synthesis Example 1: Preparation of Compound 65

[0091] Preparation of intermediate A-65

[0092] Under nitrogen protection, a-65 (23.13 g, 80 mmol), b-65 (19.69 g, 80 mmol), and K₂CO₃ (22.11 g, 160.00 mmol) were dissolved in 400 mL of toluene / ethanol / water (2:1:1). Pd(dppf)Cl₂ (1.17 g, 1.60 mmol) was added with stirring, and the mixture was heated to reflux for 5 h. After the reaction was complete, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from the resulting solid using toluene / ethanol in an 8:1 ratio to give intermediate A-65 (27.26 g, yield 83%); HPLC purity ≥ 99.85%. Mass spectrometry m / z: 410.1432 (theoretical value: 410.1419).

[0093] Preparation of compound 65

[0094] Under nitrogen protection, A-65 (12.31 g, 30.00 mmol), c-65 (8.71 g, 30.00 mmol), and sodium tert-butoxide (4.32 g, 45.00 mmol) dissolved in 135 mL of toluene were added to a reaction flask. Pd₂(dba)₃ (0.27 g, 0.30 mmol) and X-Phos (0.29 g, 0.60 mmol) were added with stirring. The mixture of the above reactants was heated under reflux for 7 h. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallization from toluene gave compound 65 (13.76 g, 74% yield). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 619.1736 (theoretical value: 619.1718). Theoretical elemental content C 42 H 25 N3OS, C, 81.40; H, 4.07; N, 6.78; (%) Measured element content (%): C, 81.44; H, 4.09; N, 6.79.

[0095] Synthesis Example 2: Preparation of Compound 93

[0096] According to the preparation method in Synthesis Example 1, a-65 was replaced with an equimolar amount of a-93, b-65 was replaced with an equimolar amount of b-93, and c-65 was replaced with an equimolar amount of c-93, yielding compound 93 (13.94 g). HPLC analysis showed a solid purity ≥ 99.99%. Mass spectrometry m / z: 619.1727 (theoretical value: 619.1718). Theoretical elemental content (%) C 42 H 25N3OS: C, 81.40; H, 4.07; N, 6.78. Measured elemental content (%): C, 81.43; H, 4.05; N, 6.77.

[0097] Synthesis Example 3: Preparation of Compound 116

[0098] According to the preparation method in Example 1, a-65 was replaced with an equimolar amount of a-116, b-65 with an equimolar amount of b-116, and c-65 with an equimolar amount of c-116, yielding compound 116 (14.47 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 660.1634 (theoretical value: 660.1620). Theoretical elemental content (%) C 43 H 24 N4O2S: C, 78.16; H, 3.66; N, 8.48. Measured elemental content (%): C, 78.13; H, 3.67; N, 8.46.

[0099] Synthesis Example 4: Preparation of Compound 169

[0100] Preparation of intermediate A-169

[0101] Under nitrogen protection, a-93 (19.55 g, 120 mmol), b-169 (33.67 g, 120 mmol), and K₂CO₃ (33.17 g, 240.00 mmol) were dissolved in 600 mL of toluene / ethanol / water (2:1:1). Pd(dppf)Cl₂ (1.76 g, 2.40 mmol) was added with stirring, and the mixture was heated under reflux for 4.5 h. After the reaction was complete, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from the resulting solid using toluene / ethanol in an 8:1 ratio to give intermediate A-169 (32.13 g, 84% yield); HPLC purity ≥ 99.77%. Mass spectrometry m / z: 318.0572 (theoretical value: 318.0560).

[0102] Preparation of intermediate B-169

[0103] Under argon protection, A-169 (25.50 g, 80.00 mmol), d-169 (13.84 g, 80.00 mmol), K2CO3 (16.59 g, 120.00 mmol), and 700 mL of toluene / ethanol / water (2:1:1) mixed solvent were added to the reaction flask. After purging the air with argon three times, Pd(PPh3)4 (0.92 g, 0.80 mmol) was added. The mixture was stirred and the system was heated under reflux for 6.5 hours. After the reaction was completed, the mixture was cooled to room temperature, distilled water was added, and the toluene layer was separated and dried with anhydrous magnesium sulfate. The solvent was concentrated by rotary evaporation after filtration, and crystals were precipitated by cooling and filtration. The crystals were then recrystallized from toluene / methanol at a ratio of 10:1 to obtain intermediate B-169 (25.68 g, yield 78%) with an HPLC purity ≥99.89%. Mass spectrometry m / z: 411.1389 (theoretical value: 411.1372).

[0104] Preparation of compound 169

[0105] Under nitrogen protection, B-169 (12.34 g, 30.00 mmol), c-169 (10.99 g, 30.00 mmol), and sodium tert-butoxide (4.32 g, 45.00 mmol) dissolved in 132 mL of toluene were added to a reaction flask with stirring. Pd₂(dba)₃ (0.27 g, 0.30 mmol) and X-Phos (0.29 g, 0.60 mmol) were then added, and the mixture was heated under reflux for 8 h. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallization from toluene yielded compound 169 (15.05 g, 72% yield). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 696.1971 (theoretical value: 696.1984). Theoretical elemental content (%) C 47 H 28 N4OS: C, 81.01; H, 4.05; N, 8.04. Measured elemental content (%): C, 81.03; H, 4.07; N, 8.06.

[0106] Synthesis Example 5: Preparation of Compound 172

[0107] According to the preparation method in Synthesis Example 4, b-169 was replaced with an equimolar amount of b-172, d-169 was replaced with an equimolar amount of a-93, and c-169 was replaced with an equimolar amount of c-172, yielding compound 172 (13.74 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 610.1478 (theoretical value: 610.1463). Theoretical elemental content (%) C39 H 22 N4O2S: C, 76.70; H, 3.63; N, 9.17. Measured elemental content (%): C, 76.74; H, 3.61; N, 9.19.

[0108] Synthesis Example 6: Preparation of Compound 175

[0109] According to the preparation method in Synthesis Example 4, b-169 was replaced with an equimolar amount of b-172, d-169 was replaced with an equimolar amount of a-93, and c-169 was replaced with an equimolar amount of c-93, yielding compound 175 (15.04 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 686.1765 (theoretical value: 686.1776). Theoretical elemental content (%) C 45 H 26 N4O2S: C, 78.70; H, 3.82; N, 8.16. Measured elemental content (%): C, 78.71; H, 3.84; N, 8.18.

[0110] Synthesis Example 7: Preparation of Compound 181

[0111] According to the preparation method in Synthesis Example 4, a-93 was replaced with an equimolar amount of a-181, b-169 was replaced with an equimolar amount of b-172, d-169 was replaced with an equimolar amount of a-181, and c-169 was replaced with an equimolar amount of c-93, yielding compound 181 (15.29 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 688.1671 (theoretical value: 688.1681). Theoretical elemental content (%) C 43 H 24 N6O2S: C, 74.99; H, 3.51; N, 12.20. Measured elemental content (%): C, 74.98; H, 3.52; N, 12.23.

[0112] Synthesis Example 8: Preparation of Compound 210

[0113] According to the preparation method in Synthesis Example 4, b-169 was replaced with an equimolar amount of b-172, d-169 with an equimolar amount of d-210, and c-169 with an equimolar amount of c-210, yielding compound 210 (15.67 g). HPLC analysis showed a solid purity ≥ 99.91%. Mass spectrometry m / z: 735.1997 (theoretical value: 735.1980). Theoretical elemental content (%) C 50H 29 N3O2S: C, 81.61; H, 3.97; N, 5.71. Measured elemental content (%): C, 81.62; H, 3.95; N, 5.74.

[0114] Synthesis Example 9: Preparation of Compound 222

[0115] According to the preparation method in Synthesis Example 4, a-93 was replaced with an equimolar amount of a-116, b-169 with an equimolar amount of b-172, d-169 with an equimolar amount of d-222, and c-169 with an equimolar amount of c-222, yielding compound 222 (15.66 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 745.2199 (theoretical value: 745.2188). Theoretical elemental content (%) C 52 H 31 N3OS: C, 83.73; H, 4.19; N, 5.63. Measured elemental content (%): C, 83.74; H, 4.16; N, 5.62.

[0116] Synthesis Example 10: Preparation of Compound 231

[0117] According to the preparation method in Synthesis Example 4, a-93 was replaced with an equimolar amount of a-116, b-169 with an equimolar amount of b-172, d-169 with an equimolar amount of d-231, and c-169 with an equimolar amount of c-65, yielding compound 231 (14.98 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 683.2046 (theoretical value: 683.2031). Theoretical elemental content (%) C 47 H 29 N3OS: C, 82.55; H, 4.27; N, 6.14. Measured elemental content (%): C, 82.58; H, 4.25; N, 6.12.

[0118] Synthesis Example 11: Preparation of Compound 285

[0119] According to the preparation method in Synthesis Example 4, b-169 was replaced with an equimolar amount of b-172, d-169 with an equimolar amount of d-285, and c-169 with an equimolar amount of c-285, yielding compound 285 (13.89 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 625.2176 (theoretical value: 625.2188). Theoretical elemental content (%) C42 H 31 N3OS: C, 80.61; H, 4.99; N, 6.71. Measured elemental content (%): C, 80.62; H, 4.96; N, 6.75.

[0120] Synthesis Example 12: Preparation of Compound 305

[0121] According to the preparation method in Synthesis Example 4, b-169 was replaced with an equimolar amount of b-172, d-169 with an equimolar amount of a-93, and c-169 with an equimolar amount of c-305, yielding compound 305 (13.85 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 615.1760 (theoretical value: 615.1777). Theoretical elemental content (%) C 39 H 17 D5N4O2S: C, 76.08; H, 4.42; N, 9.10. Measured elemental content (%): C, 76.09; H, 4.45; N, 9.13.

[0122] Synthetic Example 13: Preparation of Compound 313

[0123] According to the preparation method in Synthesis Example 4, b-169 was replaced with an equimolar amount of b-313, d-169 with an equimolar amount of a-93, and c-169 with an equimolar amount of c-93, yielding compound 313 (14.97). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 692.2167 (theoretical value: 692.2153). Theoretical elemental content (%) C 45 H 20 D6N4O2S: C, 78.01; H, 4.65; N, 8.09. Measured elemental content (%): C, 78.03; H, 4.68; N, 8.06.

[0124] Synthesis Example 14: Preparation of Compound 360

[0125] According to the preparation method in Example 1, a-65 was replaced with an equimolar amount of a-360, b-65 with an equimolar amount of b-360, and c-65 with an equimolar amount of c-360, yielding compound 360 (15.23 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 685.1658 (theoretical value: 685.1646). Theoretical elemental content (%) C 46 H 27N3S2: C, 80.56; H, 3.97; N, 6.13. Measured elemental content (%): C, 80.59; H, 3.99; N, 6.11.

[0126] Synthesis Example 15: Preparation of Compound 365

[0127] According to the preparation method in Synthesis Example 1, a-65 was replaced with an equimolar amount of a-360, and c-65 was replaced with an equimolar amount of c-365, yielding compound 365 (13.18 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 585.1346 (theoretical value: 585.1333). Theoretical elemental content (%) C 38 H 23 N3S2: C, 77.92; H, 3.96; N, 7.17. Measured elemental content (%): C, 77.95; H, 3.97; N, 7.19.

[0128] Synthesis Example 16: Preparation of Compound 381

[0129] According to the preparation method in Example 1, a-65 was replaced with an equimolar amount of a-381, b-65 was replaced with an equimolar amount of b-381, and c-65 was replaced with an equimolar amount of c-93, yielding compound 381 (15.16 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 701.1971 (theoretical value: 701.1959). Theoretical elemental content (%) C 47 H 31 N3S2: C, 80.43; H, 4.45; N, 5.99. Measured elemental content (%): C, 80.45; H, 4.46; N, 5.95.

[0130] Synthesis Example 17: Preparation of Compound 395

[0131] According to the preparation method in Synthesis Example 4, a-93 was replaced with an equimolar amount of a-381, b-169 with an equimolar amount of b-172, d-169 with an equimolar amount of d-395, and c-169 with an equimolar amount of c-93, yielding compound 395 (15.77 g). HPLC analysis showed a solid purity ≥ 99.99%. Mass spectrometry m / z: 761.1950 (theoretical value: 761.1959). Theoretical elemental content (%) C 52 H 31N3S2: C, 81.97; H, 4.10; N, 5.51. Measured elemental content (%): C, 81.98; H, 4.12; N, 5.53.

[0132] Synthesis Example 18: Preparation of Compound 405

[0133] According to the preparation method in Synthesis Example 4, a-93 was replaced with an equimolar amount of a-381, b-169 with an equimolar amount of b-405, d-169 with an equimolar amount of a-381, and c-169 with an equimolar amount of c-210, yielding compound 405 (15.53 g). HPLC analysis showed a solid purity ≥ 99.99%. Mass spectrometry m / z: 718.1334 (theoretical value: 718.1320). Theoretical elemental content (%) C 45 H 26 N4S3: C, 75.18; H, 3.65; N, 7.79. Measured elemental content (%): C, 75.16; H, 3.63; N, 7.78.

[0134] Synthesis Example 19: Preparation of Compound 406

[0135] According to the preparation method in Synthesis Example 4, a-93 was replaced with an equimolar amount of a-381, b-169 with an equimolar amount of b-172, d-169 with an equimolar amount of a-381, and c-169 with an equimolar amount of c-285, yielding compound 406 (14.27 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 642.1019 (theoretical value: 642.1007). Theoretical elemental content (%) C 39 H 22 N4S3: C, 72.87; H, 3.45; N, 8.72. Measured elemental content (%): C, 72.85; H, 3.48; N, 8.71.

[0136] Synthesis Example 20: Preparation of Compound 409

[0137] According to the preparation method in Synthesis Example 4, a-93 was replaced with an equimolar amount of a-381, b-169 with an equimolar amount of b-172, d-169 with an equimolar amount of a-381, and c-169 with an equimolar amount of c-93, yielding compound 409 (15.31 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 718.1334 (theoretical value: 718.1320). Theoretical elemental content (%) C45 H 26 N4S3: C, 75.18; H, 3.65; N, 7.79. Measured elemental content (%): C, 75.19; H, 3.62; N, 7.76.

[0138] Synthesis Example 21: Preparation of Compound 431

[0139] According to the preparation method in Synthesis Example 4, a-93 was replaced with an equimolar amount of a-381, b-169 with an equimolar amount of b-172, d-169 with an equimolar amount of a-381, and c-169 with an equimolar amount of c-431, yielding compound 431 (15.17 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 692.1174 (theoretical value: 692.1163). Theoretical elemental content (%) C 43 H 24 N4S3: C, 74.54; H, 3.49; N, 8.09. Measured elemental content (%): C, 74.56; H, 3.45; N, 8.08.

[0140] Synthesis Example 22: Preparation of Compound 440

[0141] According to the preparation method in Synthesis Example 4, a-93 was replaced with an equimolar amount of a-360, b-169 with an equimolar amount of b-172, d-169 with an equimolar amount of d-440, and c-169 with an equimolar amount of c-440, yielding compound 440 (16.10 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 777.2286 (theoretical value: 777.2272). Theoretical elemental content (%) C 53 H 35 N3S2: C, 81.82; H, 4.53; N, 5.40. Measured elemental content (%): C, 81.84; H, 4.55; N, 5.41.

[0142] Synthesis Example 23: Preparation of Compound 450

[0143] According to the preparation method in Synthesis Example 4, a-93 was replaced with an equimolar amount of a-450, b-169 with an equimolar amount of b-172, d-169 with an equimolar amount of d-450, and c-169 with an equimolar amount of c-222, yielding compound 450 (15.83 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 742.2261 (theoretical value: 742.2273). Theoretical elemental content (%) C 50 H 26 D5N3S2: C, 80.83; H, 4.88; N, 5.66. Measured elemental content (%): C, 80.85; H, 4.89; N, 5.67.

[0144] Synthesis Example 24: Preparation of Compound 464

[0145] According to the preparation method in Synthesis Example 4, a-93 was replaced with an equimolar amount of a-360, b-169 with an equimolar amount of b-172, d-169 with an equimolar amount of a-360, and c-169 with an equimolar amount of c-93, yielding compound 464 (17.51 ​​g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 870.1962 (theoretical value: 870.1946). Theoretical elemental content (%) C 57 H 34 N4S3: C, 78.59; H, 3.93; N, 6.43. Measured elemental content (%): C, 78.57; H, 3.94; N, 6.45.

[0146] Synthesis Example 25: Preparation of Compound 482

[0147] According to the preparation method in Synthesis Example 1, a-65 was replaced with an equimolar amount of a-381, b-65 with an equimolar amount of b-482, and c-65 with an equimolar amount of c-93, yielding compound 482 (13.58 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 603.1255 (theoretical value: 603.1239). Theoretical elemental content (%) C 38 H 22 FN3S2: C, 75.60; H, 3.67; N, 6.96. Measured elemental content (%): C, 75.61; H, 3.69; N, 6.99.

[0148] Synthesis Example 26: Preparation of Compound 485

[0149] According to the preparation method in Synthesis Example 4, a-93 was replaced with an equimolar amount of a-381, b-169 with an equimolar amount of b-172, d-169 with an equimolar amount of d-485, and c-169 with an equimolar amount of c-93, yielding compound 485 (17.26 g). HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 845.2157 (theoretical value: 845.2146). Theoretical elemental content (%) C 54 H 34 F3N3S2: C, 76.67; H, 4.05; N, 4.97. Measured elemental content (%): C, 76.69; H, 4.06; N, 4.98.

[0150] Synthesis Example 27: Preparation of Compound 492

[0151] According to the preparation method in Synthesis Example 1, a-65 was replaced with an equimolar amount of a-492, and c-65 was replaced with an equimolar amount of c-492, yielding compound 492 (15.11 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 689.1882 (theoretical value: 689.1897). Theoretical elemental content (%) C 46 H 23 D4N3S2: C, 80.09; H, 4.53; N, 6.09. Measured elemental content (%): C, 80.07; H, 4.52; N, 6.08.

[0152] Synthesis Example 28: Preparation of Compound 552

[0153] According to the preparation method in Synthesis Example 4, a-93 was replaced with an equimolar amount of a-381, b-169 with an equimolar amount of b-172, d-169 with an equimolar amount of d-552, and c-169 with an equimolar amount of c-285, yielding compound 552 (15.16 g). HPLC analysis showed a solid purity ≥ 99.99%. Mass spectrometry m / z: 701.1722 (theoretical value: 701.1708). Theoretical elemental content (%) C 45 H 27 N5S2: C, 77.01; H, 3.88; N, 9.98. Measured elemental content (%): C, 77.04; H, 3.86; N, 9.97.

[0154] Synthesis Example 29: Preparation of Compound 639

[0155] According to the preparation method in Example 1, a-65 was replaced with an equimolar amount of a-639, b-65 with an equimolar amount of b-639, and c-65 with an equimolar amount of c-639, yielding compound 639 (16.31 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 787.2129 (theoretical value: 787.2116). Theoretical elemental content (%) C 54 H 33 N3S2: C, 82.31; H, 4.22; N, 5.33. Measured elemental content (%): C, 82.32; H, 4.26; N, 5.32.

[0156] Synthesis Example 30: Preparation of Compound 640

[0157] According to the preparation method in Example 1, a-65 was replaced with an equimolar amount of a-116, and c-65 was replaced with an equimolar amount of c-640, yielding compound 640 (11.23 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 492.1282 (theoretical value: 492.1296). Theoretical elemental content (%) C 33 H 20 N₂OS: C, 80.46; H, 4.09; N, 5.69. Measured elemental content (%): C, 80.48; H, 4.06; N, 5.67.

[0158] Synthesis Example 31: Preparation of Compound 667

[0159] According to the preparation method in Synthesis Example 1, a-65 was replaced with an equimolar amount of a-667, b-65 with an equimolar amount of b-667, and c-65 with an equimolar amount of c-667, yielding compound 667 (14.80 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 675.1459 (theoretical value: 675.1439). Theoretical elemental content (%) C 44 H 25 N3OS2: C, 78.20; H, 3.73; N, 6.22. Measured elemental content (%): C, 78.21; H, 3.76; N, 6.23.

[0160] Synthesis Example 32: Preparation of Compound 695

[0161] According to the preparation method in Synthesis Example 4, b-169 was replaced with an equimolar amount of b-695, d-169 was replaced with an equimolar amount of d-695, and c-169 was replaced with an equimolar amount of c-695, yielding compound 695 (13.94 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 619.1736 (theoretical value: 619.1718). Theoretical elemental content (%) C 42 H 25 N3OS: C, 81.40; H, 4.07; N, 6.78. Measured elemental content (%): C, 81.41; H, 4.09; N, 6.79.

[0162] Synthesis Example 33: Preparation of Compound 704

[0163] Synthetic intermediate C-704

[0164] Under nitrogen protection, intermediates e-704 (22.63 g, 80.00 mmol), f-704 (20.33 g, 80.00 mmol), Pd(PPh3)4 (1.39 g, 1.20 mmol), KOAc (15.70 g, 160.00 mmol), and 800 mL of a toluene / ethanol / water (4:1:1) mixed solvent were added sequentially to a reaction flask. The mixture was stirred, and the reaction system was heated under reflux for 6 hours. After the reaction was completed, the mixture was cooled to room temperature, filtered to obtain a filter cake, washed with ethanol, and finally recrystallized from toluene to obtain intermediate c-704 (23.67 g, yield 81%). The purity of the solid was ≥99.75% as determined by HPLC. Mass spectrometry m / z: 363.9939 (theoretical value: 363.9921).

[0165] According to the preparation method in Synthesis Example 4, b-169 was replaced with an equimolar amount of b-172, d-169 with an equimolar amount of d-704, and c-169 with an equimolar amount of c-704, yielding compound 704 (16.69 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 794.2378 (theoretical value: 794.2392). Theoretical elemental content (%) C 57 H 34 N₂OS: C, 86.12; H, 4.31; N, 3.52. Measured elemental content (%): C, 86.13; H, 4.34; N, 3.53.

[0166] Synthesis Example 34: Preparation of Compound 712

[0167] Synthetic intermediate c-712

[0168] According to the preparation method of Synthesis Example 33, f-704 was replaced with an equimolar amount of f-712 to obtain synthetic intermediate c-712 (23.96 g, 82%). The purity of the solid was ≥99.77% as determined by HPLC. Mass spectrometry m / z: 363.9932 (theoretical value: 363.9921).

[0169] According to the preparation method in Synthesis Example 4, b-169 was replaced with an equimolar amount of b-172, d-169 with an equimolar amount of a-93, and c-169 with an equimolar amount of c-712, yielding compound 712 (15.02 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 685.1838 (theoretical value: 685.1824). Theoretical elemental content (%) C 46 H 27 N3O2S: C, 80.56; H, 3.97; N, 6.13. Measured elemental content (%): C, 80.57; H, 3.95; N, 6.12.

[0170] Synthesis Example 35: Preparation of Compound 739

[0171] Synthetic intermediate c-739

[0172] According to the preparation method of Synthesis Example 33, f-704 was replaced with an equimolar amount of f-739 to obtain synthetic intermediate c-739 (22.71 g, 78%). The purity of the solid was ≥99.74% as determined by HPLC. Mass spectrometry m / z: 365.2896 (theoretical value: 365.2880).

[0173] According to the preparation method in Synthesis Example 4, b-169 was replaced with an equimolar amount of b-172, d-169 with an equimolar amount of d-739, and c-169 with an equimolar amount of c-739, yielding compound 739 (16.77 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 809.2514 (theoretical value: 809.2501). Theoretical elemental content (%) C 57 H 35 N3OS: C, 84.52; H, 4.36; N, 5.19. Measured elemental content (%): C, 84.53; H, 4.38; N, 5.16.

[0174] Synthesis Example 36: Preparation of Compound 812

[0175] According to the preparation method in Synthesis Example 4, a-93 was replaced with an equimolar amount of a-116, b-169 with an equimolar amount of b-172, d-169 with an equimolar amount of d-812, and c-169 with an equimolar amount of c-812, yielding compound 812 (15.27 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 716.2337 (theoretical value: 716.2318). Theoretical elemental content (%) C 48 H 36 N2OSSi: C, 80.41; H, 5.06; N, 3.91. Measured elemental content (%): C, 80.43; H, 5.04; N, 3.94.

[0176] Synthesis Example 37: Preparation of Compound 905

[0177] According to the preparation method in Synthesis Example 4, a-93 was replaced with an equimolar amount of a-381, b-169 with an equimolar amount of b-172, d-169 with an equimolar amount of a-116, and c-169 with an equimolar amount of c-812, yielding compound 905 (15.16 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 701.1580 (theoretical value: 701.1596). Theoretical elemental content (%) C 46 H 27 N3OS2: C, 78.72; H, 3.88; N, 5.99. Measured elemental content (%): C, 78.74; H, 3.89; N, 5.97.

[0178] Synthesis Example 38: Preparation of Compound 933

[0179] According to the preparation method in Synthesis Example 4, a-93 was replaced with an equimolar amount of a-933, b-169 with an equimolar amount of b-172, d-169 with an equimolar amount of d-933, and c-169 with an equimolar amount of c-933, yielding compound 933 (14.95 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 711.1820 (theoretical value: 711.1803). Theoretical elemental content (%) C 48 H 29 N3S2: C, 80.98; H, 4.11; N, 5.90. Measured elemental content (%): C, 80.99; H, 4.15; N, 5.93.

[0180] Synthesis Example 39: Preparation of Compound 1001

[0181] According to the preparation method in Synthesis Example 4, a-93 was replaced with an equimolar amount of a-360, b-169 with an equimolar amount of b-172, d-169 with an equimolar amount of d-1001, and c-169 with an equimolar amount of c-1001, yielding compound 1001 (18.03 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 870.3114 (theoretical value: 870.3102). Theoretical elemental content (%) C 61 H 46 N2S2: C, 84.10; H, 5.32; N, 3.22. Measured elemental content (%): C, 84.14; H, 5.34; N, 3.23.

[0182] Synthesis Example 40: Preparation of Compound 1010

[0183] According to the preparation method in Synthesis Example 4, a-93 was replaced with an equimolar amount of a-1010, b-169 with an equimolar amount of b-172, d-169 with an equimolar amount of a-1010, and c-169 with an equimolar amount of c-695, yielding compound 1010 (13.84 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 649.1569 (theoretical value: 649.1556). Theoretical elemental content (%) C 40 H 15 D8N3S3: C, 73.93; H, 4.81; N, 6.47. Measured elemental content (%): C, 73.94; H, 4.85; N, 6.49.

[0184] Synthesis Example 41: Preparation of Compound 1209

[0185] According to the preparation method in Synthesis Example 4, a-93 was replaced with an equimolar amount of d-552, b-169 with an equimolar amount of b-172, d-169 with an equimolar amount of d-1209, and c-169 with an equimolar amount of c-1209, yielding compound 1209 (17.63 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 903.3378 (theoretical value: 903.3362). Theoretical elemental content (%) C 66 H 41 N5: C, 87.68; H, 4.57; N, 7.75. Measured elemental content (%): C, 87.67; H, 4.55; N, 7.78.

[0186] Synthesis Example 42: Preparation of Compound 1275

[0187] According to the preparation method in Synthesis Example 4, a-93 was replaced with an equimolar amount of a-381, b-169 with an equimolar amount of b-172, d-169 with an equimolar amount of d-1275, and c-169 with an equimolar amount of c-1275, yielding compound 1275 (17.02 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 821.2521 (theoretical value: 821.2501). Theoretical elemental content (%) C 58 H 35 N3OS: C, 84.75; H, 4.29; N, 5.11. Measured elemental content (%): C, 84.76; H, 4.26; N, 5.14.

[0188] [Device Examples]

[0189] 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 the McScience M6000 OLED lifetime testing system.

[0190] [Example 1]

[0191] The glass substrate was cleaned using distilled water and ultrasonic cleaning. After distilled water washing, ultrasonic cleaning was performed using solvents such as isopropanol, acetone, and methanol, followed by drying. After drying, the substrate was transferred to a plasma cleaner, and then transferred to an evaporation deposition machine. ITO / Ag / ITO was coated on the glass substrate to form an anode. HI-1:HT-1 (mass ratio 3:97) was deposited on the anode to form a hole injection layer with a thickness of 300 Å. HT-1 was deposited on the hole injection layer to form a hole transport layer with a thickness of 1200 Å. A light-emitting layer was deposited on the hole transport layer, using BH-1 as the host material and doped with 5 wt% BD-1 to form a light-emitting layer with a thickness of 300 Å. HB-1 was deposited on the light-emitting layer to form a hole blocking layer with a thickness of 100 Å. ET-1:LiQ (mass ratio 1:1) was deposited on the hole blocking layer to form an electron transport layer with a thickness of 350 Å. LiF is deposited on the electron transport layer to form an electron injection layer with a thickness of 10 Å. Mg:Ag (mass ratio 1:9) is deposited on the electron injection layer to form a cathode with a thickness of 150 Å. Compound 65 of the present invention is deposited on the cathode layer to form a capping layer with a thickness of 800 Å. Thus, an organic light-emitting device is formed.

[0192]

[0193] [Examples 2-42]

[0194] Compounds 93, 116, 169, 172, 175, 181, 210, 222, 231, 285, 305, 313, 360, 365, 381, 395, 405, 406, 409, 431, 440, 450, 464, 482, 485, 492, 552, 639, 640, 667, 695, 704, 712, 739, 812, 905, 933, 1001, 1010, 1209, and 1275 of the present invention were used to replace compound 65 in Example 1 as the capping layer material. Otherwise, an organic electroluminescent device was prepared using the same preparation method as in Example 1.

[0195] [Comparative Examples 1-3]

[0196] Compounds P-1, P-2, and P-3 were used to replace compound 65 in Example 1 as the capping material, and organic electroluminescent devices were prepared using the same preparation method as in Example 1.

[0197] The test environment was atmospheric, and the temperature was room temperature. The luminescence characteristics test results of the organic electroluminescent devices obtained by devices 1-42 and comparative examples 1-3 in the embodiments of the present invention are shown in Table 1 below.

[0198] Table 1:

[0199] As shown in Table 1, when the carbazole compound of the present invention is applied to the capping layer of an organic electroluminescent device, the device exhibits higher luminous efficiency and longer lifespan compared to comparative compounds P-1 to P-3. The carbazole compound of the present invention is a high-performance capping layer material.

[0200] 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 compound has the structure represented by Formula I: Wherein, Ar1 is selected from either formula I-1 or I-2; The i is independently selected from C(R) i Any one of N, wherein when i is bonded to other groups, i is selected from C atoms; The Y is independently selected from S, N(R) s Any one of the following; The R i R1, R2, R a R b Independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl, or two adjacent R i They connect with each other to form substituted or unsubstituted rings; The R s It is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl; a1 is selected from 0, 1, 2, or 3; when there are two or more R... a At that time, two or more R a The same or different between each other, or two adjacent R a They connect with each other to form substituted or unsubstituted rings; b1 is selected from 0, 1, 2, or 3; when there are two or more R b At that time, two or more R b They are the same as or different from each other; The Ar2 is selected from formula II; X is selected from O, S, N(R) h Any one of the following; The v is independently selected from any one of CH and N atoms; when v is bonded to other groups, the v is selected from C atoms. The R c Independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, 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 groups, substituted or unsubstituted C1-C25 heterocyclic alkanes and C6-C30 aromatic ring fused cycloyl groups, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl groups, pyridine The following are all groups: pyrimidinyl, pyrazinyl, pyridazinyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thiophenyl, benzothiophenyl, dibenzothiophenyl, benzodibenzothiophenyl, pyrroleyl, indolyl, carbazoyl, oxazolyl, benzooxazolyl, dibenzooxazolyl, thiazoyl, benzothiazoyl, dibenzothiazoyl, imidazoyl, benzoimidazoyl, dibenzoimidazoyl, quinolinyl, benzoquinolinyl, isoquinolinyl, benzoisoquinolinyl, quinazolinyl, benzoquinazolinyl, quinoxolinyl, benzoquinoxolinyl, quinoxolinyl, benzoquinoxolinyl, phenantholinyl, naphridyl, acridineyl, phenoxazinyl, phenothiazinyl; The R h It is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl; The c1 is selected from 0, 1, 2, 3, or 4; when there are two or more R... c At that time, two or more R c The same or different between each other, or two adjacent R c They connect with each other to form substituted or unsubstituted rings; The Ar3 is independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl; L1, L2, and L3 are independently selected from any one of the following: single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C6-C30 heteroarylene, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl groups, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroarylene ring fused cycloyl groups, wherein the "substituted" group in "substituted or unsubstituted" is selected from deuterium, fluorine, trifluoromethyl, cyano, nitro, silyl, C1-C25 alkyl, C3-C25 cycloalkyl, C1-C25 heterocyclic alkyl, C6-C30 aryl, C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl groups, C1-C25 heterocyclic alkanes, and... Fused cyclic groups of aromatic rings (C6-C30), alicyclic and heterocyclic groups (C3-C25), pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thiophene, benzothiophene, dibenzothiophene, benzodibenzothiophene, pyrroleyl, indolyl, carbazoleyl. Any one of the following: oxazolyl, benzoxazolyl, dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzoimidazolyl, dibenzoimidazolyl, quinolinyl, benzoquinolinyl, isoquinolinyl, benzoisoquinolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenantholinyl, naphridinyl, acridineyl, phenoxazinyl, phenthiazinyl.

2. The carbazole compound according to claim 1, characterized in that, The Ar1 is selected from any one of the following groups: The R1, R2, R a R b The group independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, or substituted or unsubstituted groups, including: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl. Benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthraceneyl, phenanthrene, pyrene, perylene, phenylene, acenaphthene, fluoranyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thiopheneyl, benzothiopheneyl, dibenzothiopheneyl, benzodibenzothiopheneyl, pyridyl Any one of the following: pyrrolyl, indolyl, carbazolyl, oxazolyl, benzoxazolyl, dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzoimidazolyl, dibenzoimidazolyl, quinolinyl, benzoquinolinyl, isoquinolinyl, benzoisoquinolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenantholinyl, naphridyl, acridineyl, phenoxazinyl, phenothiazinyl; The R s The following groups are independently selected from hydrogen, deuterium, substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl The following are all of the following: silyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthraceneyl, phenanthrene, pyrene, peryl, phenyl, acenaphthene, fluoranyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl; a1 is selected from 0, 1, 2, or 3; a2 is selected from 0, 1, 2, 3, 4, or 5; a3 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; a4 is selected from 0, 1, 2, 3, or 4; a5 is selected from 0, 1, 2, 3, 4, 5, or 6; when there are two or more R... a At that time, two or more R a The same or different between each other, or two adjacent R a They connect with each other to form substituted or unsubstituted rings; b1 is selected from 0, 1, 2, or 3; when there are two or more R b At that time, two or more R b They may be the same as or different from each other.

3. The carbazole compound according to claim 1, characterized in that, The Ar2 group is selected from any one of the following groups: The R c The group independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, nitro, or substituted or unsubstituted groups, including: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl. Benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthraceneyl, phenanthrene, pyrene, perylene, phenylene, acenaphthene, fluoranyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thiopheneyl, benzothiopheneyl, dibenzothiopheneyl, benzodibenzothiopheneyl, pyrroleyl Any one of the following: indolyl, carbazolyl, oxazolyl, benzoxazolyl, dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzoimidazolyl, dibenzoimidazolyl, quinolinyl, benzoquinolinyl, isoquinolinyl, benzoisoquinolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenantholinyl, naphridyl, acridineyl, phenoxazinyl, phenothiazinyl; The R h The following groups are independently selected from hydrogen, deuterium, substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl The following are all of the following: silyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthraceneyl, phenanthrene, pyrene, peryl, phenyl, acenaphthene, fluoranyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl; c1 is selected from 0, 1, 2, 3, or 4; c2 is selected from 0, 1, 2, or 3; c3 is selected from 0, 1, or 2; c4 is selected from 0, 1, 2, 3, 4, 5, or 6; c5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; when there are two or more R... c At that time, two or more R c The same or different between each other, or two adjacent R c They connect with each other to form substituted or unsubstituted rings.

4. A carbazole compound according to claim 1, characterized in that, The Ar3 is selected from hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted silyl group, substituted or unsubstituted C1-C25 alkyl group, substituted or unsubstituted C3-C25 cycloalkyl group, substituted or unsubstituted C1-C25 heterocycloalkyl group, and any one of the following groups: The u is independently selected from either C or N atoms, and when u is bonded to other groups, the u is selected from C atoms; The ring A is selected from substituted or unsubstituted C3~C10 alicyclic rings; X1 and X2 are independently selected from O, S, and N(R). k Any one of the following; X3, X4, and X5 are independently selected from O, S, and C(R). p R q ), N(R k Any one of the following; The R d R d 'Independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl; The R p R q Independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or R p R q The links between them form substituted or unsubstituted rings; The R k It is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl; The d1 is selected from 0, 1, 2, 3, 4, or 5; the d2 is selected from 0, 1, 2, 3, or 4; the d3 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; the d4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; the d5 is selected from 0, 1, or 2; the d6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; the d7 is selected from 0, 1, 2, or 3; the d8 is selected from 0, 1, 2, 3, 4, 5, or 6; when there are two or more R... d At that time, two or more R d The same or different between each other, or two adjacent R d They connect with each other to form substituted or unsubstituted rings; The d'1 is selected from 0, 1, or 2; when there are two or more R d At that time, two or more R d 'They are the same as or different from each other.' 5. A carbazole compound according to claim 1, characterized in that, The Ar3 group is selected from hydrogen, deuterium, fluorine, trifluoromethyl, nitro, and substituted or unsubstituted groups such as: methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, and any one of the following groups: The R d R d '、R p R q The group is independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, nitro, and substituted or unsubstituted groups of the following: methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl. Benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthraceneyl, phenanthrene, pyrene, perylene, phenylene, acenaphthene, fluoranyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thiopheneyl, benzothiopheneyl, dibenzothiopheneyl, benzodibenzothiopheneyl, pyrroleyl, indole Any one of the following: doloyl, carbazolyl, oxazolyl, benzoxazolyl, dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzoimidazolyl, dibenzoimidazolyl, quinolinyl, benzoquinolinyl, isoquinolinyl, benzoisoquinolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenantholinyl, naphridyl, acridineyl, phenoxazinyl, phenothiazinyl; The R k The following groups are independently selected from hydrogen, deuterium, substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenyl Any one of the following: silyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl; The d1 is selected from 0, 1, 2, 3, 4, or 5; the d2 is selected from 0, 1, 2, 3, or 4; the d3 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; the d4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; the d5 is selected from 0, 1, or 2; the d6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; the d7 is selected from 0, 1, 2, or 3; the d8 is selected from 0, 1, 2, 3, 4, 5, or 6; the d9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; when there are two or more R... c At that time, two or more R c The same or different between each other, or two adjacent R c They connect with each other to form substituted or unsubstituted rings; The d'1 is selected from 0, 1, or 2; the d'2 is selected from 0, 1, 2, 3, or 4; the d'3 is selected from 0, 1, 2, 3, 4, 5, or 6; the d'4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the d'5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; when there are two or more R... c At that time, two or more R c 'They are the same as or different from each other.' 6. A carbazole compound according to claim 1, characterized in that, L1, L2, and L3 are independently selected from single bonds or any one of the following groups, or from a combination of two or more of the following groups: The r is independently selected from any one of CH and N atoms; when r is bonded to other groups, the r is selected from C atoms. Z1 and Z2 are independently selected from O, S, and N(R). t Any one of the following; Z3, Z4, and Z5 are independently selected from O, S, and C(R). i R j ), N(R t Any one of the following; The ring B is selected from substituted or unsubstituted C3~C10 alicyclic rings; The R e R e '、R i R j Independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, 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 groups, substituted or unsubstituted C1-C25 heterocyclic alkanes and C6-C30 aromatic ring fused cycloyl groups, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl groups, pyridyl, Pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thiophenyl, benzothiophenyl, dibenzothiophenyl, benzodibenzothiophenyl, pyrroleyl, indolyl, carbazoleyl, oxazolyl, benzooxazolyl, dibenzooxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzoimidazolyl, dibenzoimidazolyl, quinolinyl, benzoquinolinyl, isoquinolinyl, benzoisoquinolinyl, quinazolinyl, benzoquinazolinyl, quinoxolinyl, benzoquinoxolinyl, quinoxolinyl, benzoquinoxolinyl, phenantholinyl, naphridinyl, acridineyl, phenoxazinyl, phenothiazinyl, or R i R j The links between them form substituted or unsubstituted rings; The R t It is selected from any one of hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl; The number n is selected from 1, 2, 3, or 4; The value of e1 is selected from 0, 1, 2, 3, or 4; the value of e2 is selected from 0, 1, 2, 3, 4, 5, or 6; the value of e3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the value of e4 is selected from 0, 1, or 2; when there are two or more R... e At that time, two or more R e The same or different between each other, or two adjacent R e They connect with each other to form substituted or unsubstituted rings; The term e'1 is selected from 0, 1, or 2; when there are two or more R... e At that time, two or more R e 'They are the same as or different from each other.' 7. A carbazole compound according to claim 1, characterized in that, L1, L2, and L3 are independently selected from single bonds or any one of the following groups, or from a combination of two or more of the following groups: The R e R e '、R i R j The group is independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, and substituted or unsubstituted groups of the following: methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentene. Benzyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthraceneyl, phenanthrene, pyrene, perylene, phenylene, acenaphthene, fluoranyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thiopheneyl, benzothiopheneyl, dibenzothiopheneyl, benzodibenzothiopheneyl, pyrroleyl, Any one of the following: indolyl, carbazolyl, oxazolyl, benzoxazolyl, dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzoimidazolyl, dibenzoimidazolyl, quinolinyl, benzoquinolinyl, isoquinolinyl, benzoisoquinolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenantholinyl, naphridyl, acridineyl, phenoxazinyl, phenothiazinyl; The R t Selected from hydrogen, deuterium, and the following substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetramethylsilyl, etc. The following is a list of compounds: pyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthraceneyl, phenanthrene, pyrene, peryl, phenyl, acenaphthene, fluoranyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, and triazinyl. The value of e1 is selected from 0, 1, 2, 3, or 4; the value of e2 is selected from 0, 1, 2, 3, 4, 5, or 6; the value of e3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the value of e4 is selected from 0, 1, or 2; the value of e5 is selected from 0, 1, 2, or 3; the value of e6 is selected from 0, 1, 2, 3, 4, or 5; the value of e7 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; when there are two or more R... e At that time, two or more R e The same or different between each other, or two adjacent R e They connect with each other to form substituted or unsubstituted rings; The term e'1 is selected from 0, 1, or 2; the term e'2 is selected from 0, 1, 2, 3, or 4; the term e'3 is selected from 0, 1, 2, 3, 4, 5, or 6; the term e'4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the term e'5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; when there are two or more R... e At that time, two or more R e 'They are the same as or different from each other.' 8. A carbazole compound according to claim 1, characterized in that, The carbazole compound is selected from any one of the following structures: 。 9. An organic electroluminescent device, comprising an anode, a cathode, and an organic layer, wherein the organic layer is located between the anode and the cathode or on the side of the cathode facing away from the anode, characterized in that, The organic layer comprises at least one of the carbazole compounds according to any one of claims 1 to 8.

10. An organic electroluminescent device according to claim 9, wherein the organic layer is located on the side of the cathode opposite to the anode, characterized in that, The organic layer includes a capping layer, which contains at least one of the carbazole compounds according to any one of claims 1 to 8.

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