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 film-forming property and thermal stability, can improve optical efficiency and reduce loss of light reflected by a nearby electrode during luminescence when being used in a covering layer, improves the luminous efficiency of a device, and prolongs the service life 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) have the characteristics of self-illumination, wide viewing angle, short response time, high luminous efficiency, wide color gamut, low operating voltage, thin panel, flexible size design, flexible shape design and simple manufacturing method. They have been widely used in the lighting and display fields and are considered by the industry to be one of the most promising display technologies.

[0003] The light-emitting mechanism of organic electroluminescent devices (OLEDs) involves the injection of holes and electrons from the anode and cathode, respectively, under the influence of an applied voltage. These electrons then recombine to generate excitons, releasing energy. Under the influence of an electric field, the excitons migrate, transferring energy to the luminescent material. Electrons in the luminescent material molecules transition from the ground state to an excited state. Since the excited state is unstable, the electrons return to the stable ground state, thus releasing energy as light, producing the luminescence phenomenon. The structure of an OLED device generally includes an anode, hole injection layer, hole transport layer, electron blocking layer, luminescent layer, hole blocking layer, electron transport layer, electron injection layer, cathode, and capping layer.

[0004] The low refractive index and glass transition temperature of the capping layer in existing organic light-emitting diodes (OLEDs) result in limited improvement in light extraction efficiency, failing to effectively enhance the luminous efficiency of OLEDs, leading to poor stability and shortened device lifespan. These issues restrict the further promotion and application of OLED technology in high-end displays, high-efficiency lighting, and other fields.

[0005] Therefore, in order to solve the above problems, it is crucial to develop capping materials for use in organic electroluminescent devices, thereby enabling the devices to have higher luminous efficiency and longer lifespan. Summary of the Invention

[0006] 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.

[0007] This invention provides a carbazole compound, wherein the carbazole compound is selected from the structure represented by formula I:

[0008] Wherein, Ar1 is selected from formula II;

[0009] Ring A and ring B are independently selected from any one of the substituted or unsubstituted structures in group 1, and ring A and ring B are not simultaneously selected from substituted or unsubstituted structures. ; Group 1:

[0010] X is selected from either O or S; The i is independently selected from C(R) i Any one of N; The z is independently selected from C(R) t Any one of N; The R i R t 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 Ar2 is selected from formula III;

[0011] The Y 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. R1 and R2 are 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 hIt is 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, 3 or 4; when there are two or more R1s, the two or more R1s are the same or different from each other, or two adjacent R1s are connected to each other to form a substituted or unsubstituted ring; The Ar3 is selected from deuterium, fluorine, trifluoromethyl, substituted or unsubstituted silyl group, substituted or unsubstituted C1-C25 alkyl group, substituted or unsubstituted C3-C25 cycloalkyl group or any one of the following groups;

[0012] 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 u' is independently selected from any one of CH and N atoms, and at least one is selected from N. When u' is bonded to other groups, the u' is selected from C atoms. The ring C is selected from substituted or unsubstituted C3~C10 alicyclic rings; X1 is selected from O, S, N(R) s Any one of the following; X2 is selected from C(R) p R q ), N(R s Any one of the following; X3 and X4 are independently selected from O, S, and C(R). p R q ), N(R s Any one of the following; The R c R c '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 pR 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 s It is 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; c1 is selected from 0, 1, 2, 3, 4, or 5; c2 is selected from 0, 1, 2, 3, or 4; c3 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; c4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; c5 is selected from 0, 1, or 2; c6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; c7 is selected from 0, 1, 2, or 3; c8 is selected from 0, 1, 2, 3, 4, 5, or 6; 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 c'0 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; the c'1 is selected from 0, 1, or 2; when there are two or more R... c At that time, two or more R c 'They may be the same as or different from each other; The L1 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 rings, and substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic rings.

[0013] 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.

[0014] Beneficial effects

[0015] This invention provides a carbazole compound with good film-forming properties and thermal stability. When used as a capping layer, it can improve optical efficiency and reduce light loss due to reflection from nearby electrodes during emission, thereby enhancing the luminous efficiency of the device and extending its lifespan. The compound provided by this invention has a simple preparation method, readily available raw materials, and can meet industrialization needs, showing good prospects for industrialization. Detailed Implementation

[0016] The technical solutions of the embodiments of the present invention will be clearly and completely described below. Obviously, the described embodiments are only some embodiments of the present invention, and not all embodiments. 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.

[0017] 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."

[0018] 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.

[0019] 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.

[0020] For example, Can represent , , ; Can represent , , ; Can represent , , , , , , , , , .

[0021] And so on.

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

[0023] 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.

[0024] 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.

[0025] 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.

[0026] 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.

[0027] 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.

[0028] 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.

[0029] 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.

[0030] 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.

[0031] 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.

[0032] 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.

[0033] 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, trimethyleneene, pyrene, perylene, fluorene, phenylfluorene, dibenzo[a]fluorene, spirodifluorene, benzo[a]spirodifluorene, fluorenylene, etc., but are not limited thereto.

[0034] 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.

[0035] 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, pyrene, fluoranyl, indene, dihydroindene, dihydronaphthyl, tetrahydronaphthyl, and 9,9 -Dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, spirodifluorenyl, carbazolyl, 9-phenylcarbazolyl, carbazo-indoleyl, pyrrololyl, furanyl, thiophene, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, pyridyl, 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.

[0036] The "substituted or unsubstituted silyl group" mentioned in this invention refers to -Si(R n )3 groups, wherein each R nThe 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.

[0037] 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:

[0038] 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.

[0039] 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.

[0040] This invention provides a carbazole compound, wherein the carbazole compound is selected from the structure represented by formula I:

[0041] Wherein, Ar1 is selected from formula II;

[0042] Ring A and ring B are independently selected from any one of the substituted or unsubstituted structures in group 1, and ring A and ring B are not simultaneously selected from substituted or unsubstituted structures. ; Group 1:

[0043] X is selected from either O or S; The i is independently selected from C(R) i Any one of N; The z is independently selected from C(R) t Any one of N; The R iR t 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 Ar2 is selected from formula III;

[0044] The Y 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. R1 and R2 are 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 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, 3 or 4; when there are two or more R1s, the two or more R1s are the same or different from each other, or two adjacent R1s are connected to each other to form a substituted or unsubstituted ring; The Ar3 is selected from deuterium, fluorine, trifluoromethyl, substituted or unsubstituted silyl group, substituted or unsubstituted C1-C25 alkyl group, substituted or unsubstituted C3-C25 cycloalkyl group or any one of the following groups;

[0045] 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 u' is independently selected from any one of CH and N atoms, and at least one is selected from N. When u' is bonded to other groups, the u' is selected from C atoms. The ring C is selected from substituted or unsubstituted C3~C10 alicyclic rings; X1 is selected from O, S, N(R) s Any one of the following; X2 is selected from C(R) p R q ), N(R s Any one of the following; X3 and X4 are independently selected from O, S, and C(R). p R q ), N(R s Any one of the following; The R c R c '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 Rs It is 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; c1 is selected from 0, 1, 2, 3, 4, or 5; c2 is selected from 0, 1, 2, 3, or 4; c3 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; c4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; c5 is selected from 0, 1, or 2; c6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; c7 is selected from 0, 1, 2, or 3; c8 is selected from 0, 1, 2, 3, 4, 5, or 6; 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 c'0 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; the c'1 is selected from 0, 1, or 2; when there are two or more R... c At that time, two or more R c 'They may be the same as or different from each other; The L1 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 rings, and substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic rings.

[0046] Preferably, the Selected from any one of the following groups:

[0047] 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; E1 is selected from O, S, N(R) r Any one of the following; The E2 is independently selected from O, S, C(R) u R v ), N(R r Any one of the following; The R i Ru R v 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. Benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyrene, perylene, pyridyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thiophene, benzothiophene, dibenzothiophene, benzodibenzothiophene, pyrrole, indole The following are all of the following: 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 r 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, phenylsilyl, vinyldimethyl 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, triphenylene, pyrene, peryl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, and triazinyl.

[0048] Preferably, in each six-membered ring containing i, at most two or at most one i are selected from N.

[0049] Preferably, i is independently selected from C(R) i ).

[0050] Preferably, the Ar1 is selected from any one of the following groups:

[0051]

[0052]

[0053]

[0054]

[0055]

[0056]

[0057]

[0058]

[0059]

[0060]

[0061]

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069] X is independently selected from either O or S; The R tThe group is independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, and the following groups, whether substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, n-decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, trimethylsilane. Triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane Benzocyclohexyl, naphthocyclohexyl, benzocycloheptyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyrene, perylene, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thiophene, benzothiophene, dibenzothiophene, benzene The following are all of the following: dibenzothiophene, pyrrole, indolyl, carbazolyl, oxazolyl, benzoxazolyl, dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzoimidazolyl, dibenzoimidazolyl, quinolinyl, benzoquinolinyl, isoquinolinyl, benzoisoquinolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenantholinyl, naphridyl, acridineyl, phenoxazinyl, and phenothiazinyl. t1 is selected from 0, 1, 2, 3, 4, 5, or 6; t2 is selected from 0, 1, 2, or 3; t3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; t4 is selected from 0, 1, 2, 3, or 4; t5 is selected from 0, 1, 2, 3, 4, or 5; t6 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; when there are two or more R... t At that time, two or more R t They may be the same as or different from each other.

[0070] Preferably, at most three, two, or one z in each group are selected from N atoms.

[0071] Preferably, in each six-membered ring containing z, at most three, at most two, or at most one z are selected from N atoms.

[0072] More preferably, the Ar1 is selected from any one of the following groups:

[0073] X is selected from either O or S.

[0074] Preferably, the Ar2 group is selected from any one of the following groups:

[0075] The Y is selected from O, S, N(R) h Any one of the following; R1 and R2 are 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, norbornel, 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, benzocyclobutane Alkenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyrene, perylene, pyridyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thiophene, benzothiophene, dibenzothiophene, benzodibenzothiophene, 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 h 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 Any one of silyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthraceneyl, phenanthrene, triphenylene, pyrene, perylene, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, and triazinyl; a1 is selected from 0, 1, 2, 3 or 4; a2 is selected from 0, 1, 2, 3, 4, 5 or 6; a3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; a4 is selected from 0, 1, 2 or 3; a5 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; a6 is selected from 0, 1 or 2; a7 is selected from 0, 1, 2, 3, 4 or 5; when there are two or more R1s, the two or more R1s are the same as or different from each other.

[0076] Preferably, the Ar3 is selected from deuterium, fluorine, trifluoromethyl, substituted or unsubstituted silyl groups, substituted or unsubstituted C1-C25 alkyl groups, substituted or unsubstituted C3-C25 cycloalkyl groups, or any one of the following groups:

[0077] The R c R c '、R p R qThe 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. Benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyrene, perylene, pyridyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thiophene, benzothiophene, dibenzothiophene, benzodibenzothiophene, pyrrole, indole The following are all of the following: 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 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 Any one of silyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthraceneyl, phenanthrene, triphenylene, pyrene, perylene, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, and triazinyl; c1 is selected from 0, 1, 2, 3, 4, or 5; c2 is selected from 0, 1, 2, 3, or 4; c3 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; c4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; c5 is selected from 0, 1, or 2; c6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; c7 is selected from 0, 1, 2, or 3; c8 is selected from 0, 1, 2, 3, 4, 5, or 6; c9 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 c'0 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; the c'1 is selected from 0, 1, or 2; the c'2 is selected from 0, 1, 2, 3, or 4; the c'3 is selected from 0, 1, 2, 3, 4, 5, or 6; the c'4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the c'5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; the c'6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14; the c'7 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; 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.'

[0078] Preferably, L1 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:

[0079] 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. Y1 and Y2 are independently selected from O, S, and N(R). k Any one of the following; Y3, Y4, and Y5 are independently selected from O, S, and C(R). i R j ), N(R k Any one of the following; The ring E is selected from substituted or unsubstituted C3~C10 alicyclic rings; The R e R e '、R i R jIndependently 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, 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 R i R j The links between them form substituted or unsubstituted rings; The R k 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.'

[0080] More preferably, L1 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:

[0081] The R e R e'Independently selected from hydrogen, deuterium, fluorine, cyano, nitro, or substituted or unsubstituted groups of the following: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, 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, benzocyclocyclohep ...hepane, benzocyclohepane, benzocyclohepane, benzocyclohepane, benzocyclohepane, benzocyclohepane, benzocyclohepane, benzocyclohepane, benzocyclohepane, benzocyclohepane, benzocyclohepane, Butenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthraceneyl, phenanthrene, triphenylene, pyrene, perylene, pyridyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thiophene, benzothiophene, dibenzothiophene, benzodibenzothiophene, 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 i R j The group independently selected from hydrogen, deuterium, fluorine, cyano, nitro, or substituted or unsubstituted groups of the following: 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 The following are all of the following: silyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyrene, perylene, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, and triazinyl; The R kThe following groups, independently selected from hydrogen, deuterium, substituted or unsubstituted, are allowed: 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. The following are all of the following: vinyl dimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyrene, perylene, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, and triazinyl; 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.'

[0082] Preferably, at most 3, 2, or 1 r in each group are selected from N atoms.

[0083] Most preferably, formula I is selected from any of the following structures:

[0084] 。

[0085] 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.

[0086] 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.

[0087] 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.

[0088] Preferably, the hole transport region includes at least one of a hole injection layer, a hole transport layer, and an electron blocking layer.

[0089] 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.

[0090] 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.

[0091] Preferably, the light-emitting layer comprises a host material and a dopant material.

[0092] Preferably, the electron transport region comprises at least one of an electron injection layer, an electron transport layer, and a hole blocking layer.

[0093] 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.

[0094] 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).

[0095] 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.

[0096] 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.

[0097] 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.

[0098] 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.

[0099] 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.

[0100] 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.

[0101] 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.

[0102] 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).

[0103] 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.

[0104] 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.

[0105] [Synthesis Route]

[0106] Preparation of compound I:

[0107] or

[0108] 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, L3, and i are the same as those described above.

[0109] 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.

[0110] 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.

[0111] Synthesis Example 1: Preparation of Compound 59

[0112] Preparation of intermediate A-59

[0113] Under nitrogen protection, a-59 (16.39 g, 100.00 mmol), b-59 (28.05 g, 100.00 mmol), and K2CO3 (27.64 g, 200.00 mmol) were dissolved in 500 mL of toluene / ethanol / water (2:1:1). Pd(dppf)Cl2 (1.46 g, 2.0 mmol) was added with stirring, and the mixture was heated to reflux for 4 h. After the reaction was complete, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from the solid using toluene / ethanol in an 8:1 ratio to give intermediate A-59 (26.86 g, 84% yield); HPLC purity ≥ 99.79%. Mass spectrometry m / z: 319.0524 (theoretical value: 319.0512).

[0114] Preparation of intermediate B-59

[0115] Under argon protection, A-59 (22.38 g, 70.00 mmol), c-59 (19.05 g, 70.00 mmol), K2CO3 (14.51 g, 105 mmol), and 585 mL of toluene / ethanol / water (2:1:1) mixed solvent were added to the reaction flask. After purging the air three times with argon, Pd(PPh3)4 (0.81 g, 0.70 mmol) was added. The mixture was stirred and heated under reflux for 5.5 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. The crystals were filtered and recrystallized from toluene / methanol at a ratio of 10:1 to obtain intermediate B-59 (27.57 g, yield 77%) with an HPLC purity ≥99.85%. Mass spectrometry m / z: 511.1674 (theoretical value: 511.1685).

[0116] Preparation of compound 59

[0117] Under nitrogen protection, B-59 (17.91 g, 35.00 mmol), d-59 (10.40 g, 35.00 mmol), and sodium tert-butoxide (5.05 g, 52.50 mmol) dissolved in 160 mL of toluene were added to a reaction flask with stirring. Pd₂(dba)₃ (0.32 g, 0.35 mmol) and X-Phos (0.33 g, 0.70 mmol) were then added. The mixture of the above reactants was heated under reflux for 7.5 h. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallization from toluene yielded compound 59 (19.11 g, 75% yield). HPLC analysis showed a solid purity ≥ 99.99%. Mass spectrometry m / z: 727.2270 (theoretical value: 727.2260). Theoretical elemental content (%) C 52 H 29 N3O2: C, 85.81; H, 4.02; N, 5.77. Measured elemental content (%): C, 85.82; H, 4.03; N, 5.79.

[0118] Synthesis Example 2: Preparation of Compound 79

[0119] According to the preparation method in Example 1, a-59 was replaced with an equimolar amount of a-79, c-59 with an equimolar amount of c-79, and d-59 with an equimolar amount of d-79, yielding compound 79 (19.24 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 752.2451 (theoretical value: 752.2464). Theoretical elemental content (%) C 55 H 32 N2O2: C, 87.74; H, 4.28; N, 3.72. Measured elemental content (%): C, 87.75; H, 4.26; N, 3.74.

[0120] Synthesis Example 3: Preparation of Compound 89

[0121] According to the preparation method in Synthesis Example 1, a-59 was replaced with an equimolar amount of a-89, b-59 with an equimolar amount of b-89, c-59 with an equimolar amount of c-89, and d-59 with an equimolar amount of d-89, yielding compound 89 (19.83 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 786.2981 (theoretical value: 786.2995). Theoretical elemental content (%) C 55 H 38N4O2: C, 83.95; H, 4.87; N, 7.12. Measured elemental content (%): C, 83.96; H, 4.83; N, 7.15.

[0122] Synthesis Example 4: Preparation of Compound 104

[0123] According to the preparation method in Example 1, a-59 was replaced with an equimolar amount of a-79, c-59 with an equimolar amount of c-104, and d-59 with an equimolar amount of d-104, yielding compound 104 (19.24 g). HPLC analysis showed a solid purity ≥ 99.99%. Mass spectrometry m / z: 704.2223 (theoretical value: 704.2212). Theoretical elemental content (%) C 49 H 28 N4O2: C, 83.51; H, 4.00; N, 7.95. Measured elemental content (%): C, 83.53; H, 4.02; N, 7.96.

[0124] Synthesis Example 5: Preparation of Compound 240

[0125] According to the preparation method in Example 1, a-59 was replaced with an equimolar amount of a-79, and c-59 was replaced with an equimolar amount of c-240 to obtain compound 240 (17.89 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 709.1837 (theoretical value: 709.1824). Theoretical elemental content (%) C 48 H 27 N3O2S: C, 81.22; H, 3.83; N, 5.92. Measured elemental content (%): C, 81.24; H, 3.82; N, 5.93.

[0126] Synthesis Example 6: Preparation of Compound 256

[0127] According to the preparation method in Example 1, a-59 was replaced with an equimolar amount of a-79, c-59 with an equimolar amount of c-256, and d-59 with an equimolar amount of d-256, yielding compound 256 (23.74 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 880.2740 (theoretical value: 880.2726). Theoretical elemental content (%) C 64 H 36 N2O3: C, 87.25; H, 4.12; N, 3.18. Measured elemental content (%): C, 87.26; H, 4.11; N, 3.15.

[0128] Synthesis Execution 7: Preparation of Compound 357

[0129] According to the preparation method in Example 1, a-59 was replaced with an equimolar amount of a-79, c-59 with an equimolar amount of c-357, and d-59 with an equimolar amount of d-357, yielding compound 357 (20.23 g). HPLC analysis showed a solid purity ≥ 99.99%. Mass spectrometry m / z: 770.2333 (theoretical value: 770.2318). Theoretical elemental content (%) C 53 H 30 N4O3: C, 82.58; H, 3.92; N, 7.27. Measured elemental content (%): C, 82.56; H, 3.95; N, 7.28.

[0130] Synthesis Example 8: Preparation of Compound 379

[0131] According to the preparation method in Example 1, a-59 was replaced with an equimolar amount of a-79, c-59 with an equimolar amount of c-379, and d-59 with an equimolar amount of d-379, yielding compound 379 (21.46 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 785.2154 (theoretical value: 785.2137). Theoretical elemental content (%) C 54 H 31 N3O2S: C, 82.53; H, 3.98; N, 5.35. Measured elemental content (%): C, 82.55; H, 3.99; N, 5.36.

[0132] Synthesis Example 9: Preparation of Compound 391

[0133] According to the preparation method in Example 1, a-59 was replaced with an equimolar amount of a-79, b-59 with an equimolar amount of b-391, and c-59 with an equimolar amount of c-391, yielding compound 391 (19.08 g). HPLC analysis showed a solid purity ≥ 99.99%. Mass spectrometry m / z: 726.2325 (theoretical value: 726.2307). Theoretical elemental content (%) C 53 H 30 N2O2: C, 87.58; H, 4.16; N, 3.85. Measured elemental content (%): C, 87.57; H, 4.17; N, 3.88.

[0134] Synthesis Example 10: Preparation of Compound 400

[0135] According to the preparation method in Example 1, a-59 was replaced with an equimolar amount of a-79, and c-59 was replaced with an equimolar amount of c-400, yielding compound 400 (21.42 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 826.3541 (theoretical value: 826.3559). Theoretical elemental content (%) C 60 H 46 N2O2: C, 87.14; H, 5.61; N, 3.39. Measured elemental content (%): C, 87.15; H, 5.64; N, 3.41.

[0136] Synthesis Example 11: Preparation of Compound 402

[0137] Preparation of intermediate A-402

[0138] Under nitrogen protection, a-79 (16.29 g, 100.00 mmol), b-402 (26.41 g, 100.00 mmol), and K2CO3 (27.64 g, 200.00 mmol) were dissolved in 500 mL of toluene / ethanol / water (2:1:1). Pd(dppf)Cl2 (1.46 g, 2.0 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 solid using toluene / ethanol in an 8:1 ratio to give intermediate A-402 (24.79 g, 82% yield); HPLC purity ≥ 99.83%. Mass spectrometry m / z: 302.0869 (theoretical value: 302.0855).

[0139] Preparation of compound 402

[0140] Under nitrogen protection, A-402 (10.58 g, 35.00 mmol), d-402 (14.82 g, 35.00 mmol), and sodium tert-butoxide (5.05 g, 52.50 mmol) dissolved in 160 mL of toluene were added to a reaction flask with stirring. Pd2(dba)3 (0.32 g, 0.35 mmol) and X-Phos (0.33 g, 0.70 mmol) were then added, and the mixture 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 yielded compound 402 (17.15 g, 76%), with a solid purity ≥99.94% as determined by HPLC. Mass spectrometry m / z: 644.1920 (theoretical value: 644.1900). Theoretical elemental content (%) C 45 H 25 FN2O2: C, 83.84; H, 3.91; N, 4.35. Measured elemental content (%): C, 83.85; H, 3.93; N, 4.37.

[0141] Synthesis Example 12: Preparation of Compound 403

[0142] According to the preparation method in Synthesis Example 1, a-59 was replaced with an equimolar amount of a-403, b-59 with an equimolar amount of b-403, c-59 with an equimolar amount of c-403, and d-59 with an equimolar amount of d-79, yielding compound 403 (19.21 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 694.2068 (theoretical value: 694.2057). Theoretical elemental content (%) C 49 H 27 FN2O2: C, 84.71; H, 3.92; N, 4.03. Measured elemental content (%): C, 84.73; H, 3.93; N, 4.06.

[0143] Synthesis Example 13: Preparation of Compound 406

[0144] According to the preparation method in Example 1, a-59 was replaced with an equimolar amount of a-406, b-59 with an equimolar amount of b-406, and c-59 with an equimolar amount of c-391, yielding compound 406 (19.42 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 749.2490 (theoretical value: 749.2499). Theoretical elemental content (%) C 51 H 35N3O2Si: C, 81.68; H, 4.70; N, 5.60. Measured elemental content (%): C, 81.69; H, 4.72; N, 5.64.

[0145] Synthesis Example 14: Preparation of Compound 423

[0146] According to the preparation method in Example 1, a-59 was replaced with an equimolar amount of a-79, and c-59 was replaced with an equimolar amount of c-423, yielding compound 423 (18.53 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 696.2359 (theoretical value: 696.2351). Theoretical elemental content (%) C 49 H 24 D4N2O3: C, 84.46; H, 4.63; N, 4.02. Measured elemental content (%): C, 84.47; H, 4.62; N, 4.05.

[0147] Synthesis Example 15: Preparation of Compound 443

[0148] According to the preparation method in Synthesis Example 1, a-59 was replaced with an equimolar amount of a-79, b-59 with an equimolar amount of b-443, c-59 with an equimolar amount of c-443, and d-59 with an equimolar amount of d-357, yielding compound 443 (19.52 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 714.2259 (theoretical value: 714.2248). Theoretical elemental content (%) C 49 H 22 D6N2O2S: C, 82.33; H, 4.79; N, 3.92. Measured elemental content (%): C, 82.31; H, 4.77; N, 3.93.

[0149] Synthesis Example 16: Preparation of Compound 507

[0150] According to the preparation method in Example 1, a-59 was replaced with an equimolar amount of a-507, c-59 with an equimolar amount of c-507, and d-59 with an equimolar amount of d-507, yielding compound 507 (21.45 g). HPLC analysis showed a solid purity ≥ 99.91%. Mass spectrometry m / z: 816.2255 (theoretical value: 816.2235). Theoretical elemental content (%) C 59 H 32N₂OS: C, 86.74; H, 3.95; N, 3.43. Measured elemental content (%): C, 86.76; H, 3.93; N, 3.44.

[0151] Synthesis Example 17: Preparation of Compound 562

[0152] According to the preparation method in Example 1, a-59 was replaced with an equimolar amount of a-507, c-59 with an equimolar amount of c-562, and d-59 with an equimolar amount of d-562, yielding compound 562 (20.69 g). HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 809.2154 (theoretical value: 809.2137). Theoretical elemental content (%) C 56 H 31 N3O2S: C, 83.04; H, 3.86; N, 5.19. Measured elemental content (%): C, 83.05; H, 3.83; N, 5.15.

[0153] Synthetic Example 18: Preparation of Compound 579

[0154] According to the preparation method in Synthesis Example 1, a-59 was replaced with an equimolar amount of a-579, and c-59 was replaced with an equimolar amount of c-579, yielding compound 579 (20.69 g). HPLC analysis showed a solid purity ≥ 99.99%. Mass spectrometry m / z: 798.1817 (theoretical value: 798.1800). Theoretical elemental content (%) C 55 H 30 N₂OS₂: C, 82.68; H, 3.78; N, 3.51. Measured elemental content (%): C, 82.69; H, 3.75; N, 3.53.

[0155] Synthesis Example 19: Preparation of Compound 614

[0156] According to the preparation method in Example 1, a-59 was replaced with an equimolar amount of a-507, and c-59 was replaced with an equimolar amount of c-614 to obtain compound 614 (18.27 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 724.2198 (theoretical value: 724.2184). Theoretical elemental content (%) C 50 H 32 N2O2S: C, 82.85; H, 4.45; N, 3.86. Measured elemental content (%): C, 82.87; H, 4.46; N, 3.85.

[0157] Synthesis Example 20: Preparation of Compound 731

[0158] According to the preparation method in Synthesis Example 1, a-59 was replaced with an equimolar amount of a-507, b-59 with an equimolar amount of b-731, c-59 with an equimolar amount of c-731, and d-59 with an equimolar amount of d-731, yielding compound 731 (18.97 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 694.1814 (theoretical value: 694.1827). Theoretical elemental content (%) C 47 H 26 N4OS: C, 81.25; H, 3.77; N, 8.06. Measured elemental content (%): C, 81.26; H, 3.79; N, 8.07.

[0159] Synthesis Example 21: Preparation of Compound 740

[0160] According to the preparation method in Synthesis Example 1, a-59 was replaced with an equimolar amount of a-507, c-59 with an equimolar amount of c-740, and d-59 with an equimolar amount of d-740, yielding compound 740 (19.38 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 700.1444 (theoretical value: 700.1432). Theoretical elemental content (%) C 44 H 23 F3N2O2S: C, 75.42; H, 3.31; N, 4.00. Measured elemental content (%): C, 75.45; H, 3.32; N, 4.03.

[0161] Synthesis Example 22: Preparation of Compound 755

[0162] According to the preparation method in Example 1, a-59 was replaced with an equimolar amount of a-507, c-59 with an equimolar amount of c-755, and d-59 with an equimolar amount of d-755, yielding compound 755 (19.27 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 733.2080 (theoretical value: 733.2098). Theoretical elemental content (%) C 48 H 19 D8N3OS2: C, 78.55; H, 4.80; N, 5.73. Measured elemental content (%): C, 78.56; H, 4.82; N, 5.74.

[0163] Synthesis Example 23: Preparation of Compound 795

[0164] According to the preparation method in Example 1, a-59 was replaced with an equimolar amount of a-795, and c-59 was replaced with an equimolar amount of c-795, yielding compound 795 (20.67 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 766.2746 (theoretical value: 766.2733). Theoretical elemental content (%) C 55 H 34 N4O: C, 86.14; H, 4.47; N, 7.31. Measured elemental content (%): C, 86.15; H, 4.49; N, 7.34.

[0165] Synthesis Example 24: Preparation of Compound 827

[0166] According to the preparation method in Synthesis Example 1, a-59 was replaced with an equimolar amount of a-79, b-59 with an equimolar amount of b-827, c-59 with an equimolar amount of c-403, and d-59 with an equimolar amount of d-827, yielding compound 827 (18.43 g). HPLC analysis showed a solid purity ≥ 99.99%. Mass spectrometry m / z: 692.1936 (theoretical value: 692.1922). Theoretical elemental content (%) C 49 H 28 N₂OS: C, 84.95; H, 4.07; N, 4.04. Measured elemental content (%): C, 84.93; H, 4.09; N, 4.05.

[0167] Synthesis Example 25: Preparation of Compound 921

[0168] Synthetic intermediate d-921

[0169] Under nitrogen protection, e-921 (33.38 g, 120.00 mmol), f-921 (29.10 g, 120.00 mmol), potassium carbonate (33.17 g, 240.00 mmol), tetraphenylphosphine palladium (1.66 g, 1.44 mmol), and 600 mL of toluene / ethanol / water (2:1:1) mixed solvent were added to a reaction flask. The mixture was stirred and the reaction system was heated under reflux for 3.5 h. After the reaction was completed, the mixture was cooled to room temperature, toluene was added, and the phases were separated. The toluene phase was washed three times with distilled water, dried with anhydrous magnesium sulfate, and the solvent was concentrated by rotary evaporation. Crystallization was carried out at a lower temperature, filtered, and the resulting solid was recrystallized from toluene to obtain intermediate d-921 (39.91 g, yield 84%); HPLC purity ≥ 99.72%. Mass spectrometry m / z: 395.0550 (theoretical value: 395.0535).

[0170] According to the preparation method in Synthesis Example 1, a-59 was replaced with an equimolar amount of a-79, c-59 was replaced with an equimolar amount of c-921, and d-59 was replaced with an equimolar amount of d-921, yielding compound 921 (25.20 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 959.2978 (theoretical value: 959.2970). Theoretical elemental content (%) C 69 H 41 N3OS: C, 86.31; H, 4.30; N, 4.38. Measured elemental content (%): C, 86.33; H, 4.31; N, 4.39.

[0171] Synthesis Example 26: Preparation of Compound 923

[0172] According to the preparation method in Synthesis Example 1, a-59 was replaced with an equimolar amount of a-923, c-59 with an equimolar amount of c-923, and d-59 with an equimolar amount of d-923, yielding compound 923 (19.52 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 819.2359 (theoretical value: 819.2344). Theoretical elemental content (%) C 58 H 33 N3OS: C, 84.96; H, 4.06; N, 5.12. Measured elemental content (%): C, 84.94; H, 4.09; N, 5.14.

[0173] Synthesis Example 27: Preparation of Compound 962

[0174] Synthetic intermediate d-962

[0175] According to the preparation method of Synthesis Example 25, f-921 was replaced with an equimolar amount of f-962 to obtain synthetic intermediate d-962 (35.79 g, 86%). The purity of the solid was ≥99.75% as determined by HPLC. Mass spectrometry m / z: 346.0339 (theoretical value: 346.0331).

[0176] According to the preparation method in Synthesis Example 11, b-402 was replaced with an equimolar amount of b-962, and d-402 was replaced with an equimolar amount of d-962, yielding compound 962 (16.01 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 601.1963 (theoretical value: 601.1954). Theoretical elemental content (%) C 39 H 15 D7N4OS: C, 77.85; H, 4.86; N, 9.31. Measured elemental content (%): C, 77.86; H, 4.85; N, 9.32.

[0177] Synthesis Example 28: Preparation of Compound 988

[0178] According to the preparation method in Example 1, a-59 was replaced with an equimolar amount of a-79, c-59 with an equimolar amount of c-988, and d-59 with an equimolar amount of d-988, yielding compound 988 (21.54 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 788.2443 (theoretical value: 788.2436). Theoretical elemental content (%) C 55 H 28 D4N2O2S: C, 83.73; H, 4.60; N, 3.55. Measured elemental content (%): C, 83.72; H, 4.66; N, 3.57.

[0179] Synthesis Example 29: Preparation of Compound 1006

[0180] According to the preparation method in Example 1, a-59 was replaced with an equimolar amount of a-507, c-59 with an equimolar amount of c-1006, and d-59 with an equimolar amount of d-1006, yielding compound 1006 (18.73 g). HPLC analysis showed a solid purity ≥ 99.99%. Mass spectrometry m / z: 732.1682 (theoretical value: 732.1694). Theoretical elemental content (%) C 51 H 28 N2S2: C, 83.58; H, 3.85; N, 3.82. Measured elemental content (%): C, 83.59; H, 3.83; N, 3.83.

[0181] Synthesis Example 30: Preparation of Compound 1007

[0182] Synthetic intermediate d-1007

[0183] According to the preparation method of Synthesis Example 25, f-921 was replaced with an equimolar amount of f-1007 to obtain synthetic intermediate d-1007 (35.38 g, 85%), and the solid purity was ≥99.76% as determined by HPLC. Mass spectrometry m / z: 346.0345 (theoretical value: 346.0331).

[0184] According to the preparation method in Synthesis Example 1, a-59 was replaced with an equimolar amount of a-507, b-59 with an equimolar amount of b-403, c-59 with an equimolar amount of c-443, and d-59 with an equimolar amount of d-1007, yielding compound 1007 (20.28 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 742.1337 (theoretical value: 742.1320). Theoretical elemental content (%) C 47 H 26 N4S3: C, 75.98; H, 3.53; N, 7.54. Measured elemental content (%): C, 75.95; H, 3.56; N, 7.52.

[0185] Synthesis Example 31: Preparation of Compound 1035

[0186] According to the preparation method in Example 1, a-59 was replaced with an equimolar amount of a-1035, c-59 was replaced with an equimolar amount of c-1035, and d-59 was replaced with an equimolar amount of d-1035, yielding compound 1035 (21.92 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 823.2132 (theoretical value: 823.2116). Theoretical elemental content (%) C 57 H 33 N3S2: C, 83.08; H, 4.04; N, 5.10. Measured elemental content (%): C, 83.07; H, 4.08; N, 5.12.

[0187] Synthesis Example 32: Preparation of Compound 1083

[0188] According to the preparation method in Synthesis Example 1, a-59 was replaced with an equimolar amount of a-507, b-59 with an equimolar amount of b-1083, c-59 with an equimolar amount of c-403, and d-59 with an equimolar amount of d-1083, yielding compound 1083 (20.69 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 798.1814 (theoretical value: 798.1800). Theoretical elemental content (%) C 55 H 30 N₂OS₂: C, 82.68; H, 3.78; N, 3.51. Measured elemental content (%): C, 82.66; H, 3.79; N, 3.53.

[0189] Synthesis Example 33: Preparation of Compound 1143

[0190] According to the preparation method in Example 1, a-59 was replaced with an equimolar amount of a-1143, c-59 was replaced with an equimolar amount of c-391, and d-59 was replaced with an equimolar amount of d-1143, yielding compound 1143 (20.82 g). HPLC analysis showed a solid purity ≥ 99.99%. Mass spectrometry m / z: 752.2479 (theoretical value: 752.2464). Theoretical elemental content (%) C 55 H 32 N2O2: C, 87.74; H, 4.28; N, 3.72. Measured elemental content (%): C, 87.75; H, 4.25; N, 3.73.

[0191] Synthesis Example 34: Preparation of Compound 1179

[0192] According to the preparation method in Synthesis Example 1, a-59 was replaced with an equimolar amount of a-1179, b-59 was replaced with an equimolar amount of b-1179, and c-59 was replaced with an equimolar amount of c-1179, yielding compound 1179 (21.82 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 830.2437 (theoretical value: 830.2426). Theoretical elemental content (%) C 57 H 38 N₂OS₂: C, 82.38; H, 4.61; N, 3.37. Measured elemental content (%): C, 82.36; H, 4.62; N, 3.38.

[0193] Synthesis Example 35: Preparation of Compound 1210

[0194] According to the preparation method in Example 1, a-59 was replaced with an equimolar amount of a-1210, c-59 was replaced with an equimolar amount of c-1210, and d-59 was replaced with an equimolar amount of d-827, yielding compound 1210 (20.75 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 834.2172 (theoretical value: 834.2163). Theoretical elemental content (%) C 59 H 34 N2S2: C, 84.86; H, 4.10; N, 3.35. Measured elemental content (%): C, 84.87; H, 4.12; N, 3.33.

[0195] [Device Examples]

[0196] 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.

[0197] [Example 1]

[0198] 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 onto 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 150 Å. HT-1 was deposited on the hole injection layer to form a hole transport layer with a thickness of 1000 Å. A light-emitting layer was deposited on the hole transport layer, using GH-1 as the host material and doped with 6 wt% GD-1 to form a light-emitting layer with a thickness of 300 Å. ET-1:LiQ (mass ratio 1:1) was deposited on the light-emitting layer to form an electron transport layer with a thickness of 300 Å. LiF was deposited on the electron transport layer to form an electron injection layer with a thickness of 10 Å. A Mg:Ag mixture (mass ratio 1:9) is deposited on the electron injection layer to form a cathode with a thickness of 150 Å. Compound 59 of this invention is then deposited on the cathode layer to form a capping layer with a thickness of 750 Å. This forms an organic light-emitting device.

[0199]

[0200] [Examples 2-35]

[0201] Compounds 79, 89, 104, 240, 256, 357, 379, 391, 400, 402, 403, 406, 423, 443, 507, 562, 579, 614, 731, 740, 755, 795, 827, 921, 923, 962, 988, 1006, 1007, 1035, 1083, 1143, 1179, and 1210 of the present invention were used to replace compound 59 in Example 1 as the capping layer material. Otherwise, an organic electroluminescent device was prepared using the same preparation method as in Example 1.

[0202] [Comparative Examples 1-2]

[0203] Organic electroluminescent devices were prepared by replacing compound 59 in Example 1 with compounds P-1 and P-2, respectively, as capping materials, except that the preparation method was the same as in Example 1.

[0204] The test environment was atmospheric, and the temperature was room temperature. The luminescence characteristics test results of the organic electroluminescent devices obtained by devices 1-35 and comparative examples 1-2 in the embodiments of the present invention are shown in Table 1 below.

[0205] Table 1:

[0206]

[0207] As shown in Table 1, when the carbazole compound of the present invention is applied to the capping layer of organic electroluminescent devices, the devices exhibit higher luminous efficiency and longer lifespan compared to comparative compounds P-1 to P-2. The carbazole compound of the present invention is a high-performance capping layer material.

[0208] 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 formula II; Ring A and ring B are independently selected from any one of the substituted or unsubstituted structures in group 1, and ring A and ring B are not simultaneously selected from substituted or unsubstituted structures. ; Group 1: X is selected from either O or S; The i is independently selected from C(R) i Any one of N; The z is independently selected from C(R) t Any one of N; The R i R t 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 Ar2 is selected from Formula III; The Y 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. R1 and R2 are 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 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, 3 or 4; when there are two or more R1s, the two or more R1s are the same or different from each other, or two adjacent R1s are connected to each other to form a substituted or unsubstituted ring; The Ar3 is selected from deuterium, fluorine, trifluoromethyl, substituted or unsubstituted silyl group, substituted or unsubstituted C1-C25 alkyl group, substituted or unsubstituted C3-C25 cycloalkyl group or any one of the following groups; 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 u' is independently selected from any one of CH and N atoms, and at least one is selected from N. When u' is bonded to other groups, the u' is selected from C atoms. The ring C is selected from substituted or unsubstituted C3~C10 alicyclic rings; X1 is selected from O, S, N(R) s Any one of the following; X2 is selected from C(R) p R q ), N(R s Any one of the following; X3 and X4 are independently selected from O, S, and C(R). p R q ), N(R s Any one of the following; The R c R c '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 s It is 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; c1 is selected from 0, 1, 2, 3, 4, or 5; c2 is selected from 0, 1, 2, 3, or 4; c3 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; c4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; c5 is selected from 0, 1, or 2; c6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; c7 is selected from 0, 1, 2, or 3; c8 is selected from 0, 1, 2, 3, 4, 5, or 6; 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 c'0 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; the c'1 is selected from 0, 1, or 2; when there are two or more R... c At that time, two or more R c 'They may be the same as or different from each other; The L1 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 rings, and substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic rings.

2. The carbazole compound according to claim 1, characterized in that, The Ar1 is selected from any one of the following groups: X is independently selected from either O or S; The R t The group is independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, and the following groups, whether substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, n-decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, trimethylsilane. Triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane Benzocyclohexyl, naphthocyclohexyl, benzocycloheptyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyrene, perylene, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thiophene, benzothiophene, dibenzothiophene, benzene The following are all of the following: dibenzothiophene, pyrrole, indolyl, carbazolyl, oxazolyl, benzoxazolyl, dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzoimidazolyl, dibenzoimidazolyl, quinolinyl, benzoquinolinyl, isoquinolinyl, benzoisoquinolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenantholinyl, naphridyl, acridineyl, phenoxazinyl, and phenothiazinyl. t1 is selected from 0, 1, 2, 3, 4, 5, or 6; t2 is selected from 0, 1, 2, or 3; t3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; t4 is selected from 0, 1, 2, 3, or 4; t5 is selected from 0, 1, 2, 3, 4, or 5; t6 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; when there are two or more R... t At that time, two or more R t They may be the same as or different from each other.

3. The carbazole compound according to claim 1, characterized in that, The Ar1 is selected from any one of the following groups: X is selected from either O or S.

4. A carbazole compound according to claim 1, characterized in that, The Ar2 group is selected from any one of the following groups: The Y is selected from O, S, N(R) h Any one of the following; R1 and R2 are 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, norbornel, 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, benzocyclobutane Alkenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyrene, perylene, pyridyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thiophene, benzothiophene, dibenzothiophene, benzodibenzothiophene, 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 h 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 Any one of silyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthraceneyl, phenanthrene, triphenylene, pyrene, perylene, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, and triazinyl; a1 is selected from 0, 1, 2, 3 or 4; a2 is selected from 0, 1, 2, 3, 4, 5 or 6; a3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; a4 is selected from 0, 1, 2 or 3; a5 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; a6 is selected from 0, 1 or 2; a7 is selected from 0, 1, 2, 3, 4 or 5; when there are two or more R1s, the two or more R1s are the same as or different from each other.

5. A carbazole compound according to claim 1, characterized in that, The Ar3 is selected from deuterium, fluorine, trifluoromethyl, substituted or unsubstituted silyl groups, substituted or unsubstituted C1-C25 alkyl groups, substituted or unsubstituted C3-C25 cycloalkyl groups, or any one of the following groups: The R c R c '、R p R q 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. Benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyrene, perylene, pyridyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thiophene, benzothiophene, dibenzothiophene, benzodibenzothiophene, pyrrole, indole The following are all of the following: 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 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 Any one of silyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthraceneyl, phenanthrene, triphenylene, pyrene, perylene, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, and triazinyl; c1 is selected from 0, 1, 2, 3, 4, or 5; c2 is selected from 0, 1, 2, 3, or 4; c3 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; c4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; c5 is selected from 0, 1, or 2; c6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; c7 is selected from 0, 1, 2, or 3; c8 is selected from 0, 1, 2, 3, 4, 5, or 6; c9 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 c'0 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; the c'1 is selected from 0, 1, or 2; the c'2 is selected from 0, 1, 2, 3, or 4; the c'3 is selected from 0, 1, 2, 3, 4, 5, or 6; the c'4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the c'5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; the c'6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14; the c'7 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; 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, The L1 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. Y1 and Y2 are independently selected from O, S, and N(R). k Any one of the following; Y3, Y4, and Y5 are independently selected from O, S, and C(R). i R j ), N(R k Any one of the following; The ring E is selected from substituted or unsubstituted C3~C10 alicyclic rings; The R e R e '、R i R j 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, 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 R i R j The links between them form substituted or unsubstituted rings; The R k 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, The L1 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 'Independently selected from hydrogen, deuterium, fluorine, cyano, nitro, or substituted or unsubstituted groups of the following: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, 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, benzocyclocyclohep ...hepane, benzocyclohepane, benzocyclohepane, benzocyclohepane, benzocyclohepane, benzocyclohepane, benzocyclohepane, benzocyclohepane, benzocyclohepane, benzocyclohepane, benzocyclohepane, Butenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthraceneyl, phenanthrene, triphenylene, pyrene, perylene, pyridyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thiophene, benzothiophene, dibenzothiophene, benzodibenzothiophene, 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 i R j The group independently selected from hydrogen, deuterium, fluorine, cyano, nitro, or substituted or unsubstituted groups of the following: 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 The following are all of the following: silyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyrene, perylene, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, and triazinyl; The R k The following groups, independently selected from hydrogen, deuterium, substituted or unsubstituted, are allowed: 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. The following are all of the following: vinyl dimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyrene, perylene, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, and triazinyl; 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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