A carbazole compound and an organic electroluminescent device thereof

Abstract

The application provides a carbazole compound and an organic electroluminescent device thereof, and particularly relates to the technical field of organic optoelectronic materials.The compound has good thermal stability and refractive index, can reduce light loss caused by reflection of a nearby electrode during light emission when used as a cover layer material, increase light extraction efficiency, effectively improve the stability of a film layer, can improve the light-emitting efficiency of a device, and prolong the service life of the device.The compound has a simple preparation method, raw materials are easy to obtain, can be widely applied to the fields of organic thin film transistors, panel displays and the like, and has good application effect and industrialization prospect.

Description

Technical Field

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

[0002] Organic light-emitting diodes (OLEDs) are one of the most promising new display technologies. Compared with traditional display technologies such as liquid crystal displays (LCDs), OLEDs have advantages such as light weight, small thickness, wide viewing angle, fast response speed, low energy consumption, high efficiency, wide adaptability, and good color purity. They are expected to replace traditional liquid crystal displays and fluorescent lighting, and have broad application prospects.

[0003] OLEDs consist of a cathode, an anode, and an organic layer. The organic layer includes a hole injection layer (HIL), a hole transport layer (HTL), an electron blocking layer (EBL), an emissive layer (EML), and a capping layer (CPL). The light-emitting principle of OLEDs involves holes and electrons being injected into the organic layer from the anode and cathode respectively under the influence of an external electric field. They then enter the emissive layer through the hole transport region and the electron transport region, respectively. In the emissive layer, they recombine to generate excitons, releasing energy. These excitons migrate under the influence of the electric field, transferring energy to the luminescent material in the emissive layer. Electrons in the luminescent material molecules transition from the ground state to an excited state, and then back to the ground state, releasing energy as light. By placing a capping layer with a high refractive index outside the semi-transparent electrode, total internal reflection loss and waveguide loss in the OLED device are reduced, trapping light within the device is coupled out, enhancing light extraction efficiency, thereby improving the device's luminous efficiency and extending its lifespan. However, the existing materials have poor compatibility with other film layers of the device due to their refractive index, transmittance and other optical parameters. This makes it difficult to effectively suppress internal light loss, resulting in low light extraction efficiency. A large amount of light energy is blocked inside the device, which directly affects the brightness of the device. Alternatively, some materials may have unstable chemical properties, leading to insufficient charge recombination and shortened device lifespan.

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

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

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

[0007] Wherein, Ar1 is selected from formula II;

[0008] 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:

[0009] X is selected from either O or S; The i is independently selected from C(R) i Any one of N, wherein when i is bonded to other groups, i is selected from C atoms; The z is selected from C(R) t Any one of N; The Ar2 is selected from Formula III;

[0010] The v is independently selected from any one of CH and N atoms; when v is bonded to other groups, the v is selected from C atoms. The R i R t R2 is independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl group, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl group, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl group, or two adjacent Rs. i They connect with each other to form substituted or unsubstituted rings; The b1 is selected from 0, 1, 2, 3, 4 or 5; when there are two or more R2, the two or more R2 are the same or different from each other, or two adjacent R2 are connected to each other to form a substituted or unsubstituted ring; The Ar3 is selected from any one of the following: substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl groups, substituted or unsubstituted C1-C25 heterocyclic alkanes and C6-C30 aromatic ring fused cycloyl groups, and substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl groups; L1, L2, and L3 are 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.

[0011] 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.

[0012] Beneficial effects

[0013] This invention provides a carbazole compound with good thermal stability and refractive index. When used as a capping layer material, it can reduce light loss due to reflection from nearby electrodes during luminescence, increase light extraction efficiency, effectively improve film stability, enhance device luminous efficiency, and extend device 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

[0014] 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.

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

[0016] In this specification, when a substituent or linking site lies within a bond that extends through two or more rings, it indicates that the substituent or linking site can be linked to any one of the two or more rings, specifically to any one of the corresponding optional sites within the ring. For example, Can represent or ; Can represent , , And so on.

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

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

[0019] And so on.

[0020] Examples of halogen atoms described in this invention may include fluorine, chlorine, bromine, and iodine.

[0021] 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.

[0022] 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.

[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 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.

[0025] 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.

[0026] The arylene group described in this invention can be a monocyclic arylene, a polycyclic arylene, or a fused-ring arylene. An arylene refers to a divalent group formed by removing two hydrogen atoms from the aromatic nucleus of an aromatic hydrocarbon molecule. It preferably has 6 to 30 carbon atoms, more preferably 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 18 carbon atoms, and most preferably 6 to 12 carbon atoms. Examples include phenylene, biphenylene, terphenylene, naphthylene, anthracene, phenanthrene, tricrene, pyrene, perylene, phenanthrene, acenaphthene, fluorene, phenyl fluorene, dibenzo[a]fluorene, spirodifluorene, benzo[a]spirodifluorene, fluorene anthracene, etc., but are not limited thereto.

[0027] 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.

[0028] 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.

[0029] 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.

[0030] The fused cyclic group of alicyclic and heteroaromatic rings described 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.

[0031] 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.

[0032] 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.

[0033] The "substituted or unsubstituted silyl group" mentioned in this invention refers to -Si(R k )3 groups, wherein each R k The 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.

[0034] The substituents described in the "substituted or unsubstituted" of this invention may be independently selected from deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcohols of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C1-C6 alkylthio, substituted or unsubstituted C1-C12 alkylamine, substituted or unsubstituted C6-C30 aryloxy, etc., but are not limited thereto, or adjacent substituents may be linked to form a ring. Preferred compounds include deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl groups, C1-C25 alkyl groups, C3-C25 cycloalkyl groups, C6-C30 aryl groups, C2-C30 heteroaryl groups, C3-C30 alicyclic and C6-C30 fused cycloyl groups, and C1-C12 alkoxy groups. Specific examples may include deuterium, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, propyl, butyl, cyclopropyl, cyclohexyl, adamantyl, norbornel, phenyl, tolyl, mesitylene, pentadeuterated phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, perylene, phenylene, acenaphthene, fluoranyl, pyrene, fluoranyl, indene, dihydroindene, dihydronaphthyl, and tetrahydronaphthyl. The following are listed: 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, spirodifluorenyl, carbazolyl, 9-phenylcarbazolyl, carbazo-indolyl, pyrrololyl, furanyl, thiophene, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, pyridinyl, pyrimidinyl, pyrazinyl, pyrazinyl, triazinyl, oxazolyl, thiazolyl, imidazolyl, benzooxazolyl, benzothiazolyl, benzotriazolyl, benzoimidazolyl, quinolinyl, isoquinolinyl, quinoxolinyl, quinazolinyl, phenothiazinyl, phenothiazinyl, acridineyl, benzocyclobutyl, benzocyclobutenyl, benzocyclopentyl, benzocyclopentenyl, benzocyclohexyl, benzocyclohexenyl, etc., but not limited to these. Or, when there are multiple substituents, the multiple substituents may be the same or different from each other; or adjacent substituents may be connected to form a ring.

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

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

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

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

[0039] Wherein, Ar1 is selected from formula II;

[0040] 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:

[0041] X is selected from either O or S; The i is independently selected from C(R) i Any one of N, wherein when i is bonded to other groups, i is selected from C atoms; The z is selected from C(R) t Any one of N; The Ar2 is selected from Formula III;

[0042] The v is independently selected from any one of CH and N atoms; when v is bonded to other groups, the v is selected from C atoms. The R i R tR2 is independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl group, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl group, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl group, or two adjacent Rs. i They connect with each other to form substituted or unsubstituted rings; The b1 is selected from 0, 1, 2, 3, 4 or 5; when there are two or more R2, the two or more R2 are the same or different from each other, or two adjacent R2 are connected to each other to form a substituted or unsubstituted ring; The Ar3 is selected from any one of the following: substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl groups, substituted or unsubstituted C1-C25 heterocyclic alkanes and C6-C30 aromatic ring fused cycloyl groups, and substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl groups; L1, L2, and L3 are 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.

[0043] Preferably, the Selected from any one of the following groups:

[0044] 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; Z1 is selected from O, S, N(R) h Any one of the following; Z2 is independently selected from O, S, C(R) u R v ), N(R h Any one of the following; The Ri R u R v 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 u R v The links between them form substituted or unsubstituted rings; The R h It is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl.

[0045] Preferably, in each six-membered ring containing i, at most two or at most one i are selected from N.

[0046] Preferably, i is independently selected from C(R) i ).

[0047] Preferably, the Ar1 is selected from any one of the following groups:

[0048]

[0049]

[0050]

[0051]

[0052]

[0053]

[0054]

[0055]

[0056]

[0057]

[0058]

[0059]

[0060]

[0061]

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068] 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, trimethylsilyl. Triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane Naphthocyclohexyl, benzocycloheptyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, pyrene, perylene, phenylene, acenaphthene, fluoranyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thiophene, benzothiophene, dibenzothiophene The following are all of the following: benzodibenzothiophene, pyrrole, indolyl, carbazolyl, oxazolyl, benzoxazolyl, dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzoimidazolyl, dibenzoimidazolyl, quinolinyl, benzoquinolinyl, isoquinolinyl, benzoisoquinolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenantholinyl, naphridyl, acridineyl, phenoxazinyl, 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.

[0069] Preferably, at most three, two, or one z in each group are selected from N atoms.

[0070] Preferably, in each six-membered ring containing z, at most three, at most two, or at most one z is selected from N atoms.

[0071] More preferably, the Ar1 is selected from any one of the following groups: .

[0072] Preferably, the Ar2 group is selected from any one of the following groups:

[0073] R2 is independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, and substituted or unsubstituted groups of the following: 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, trimethylsilyl Alkyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclocyclo Hexyl, naphthocyclohexyl, benzocycloheptyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, pyrene, peryl, phenyl, acenaphthene, fluoranyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thiophene, benzothiophene, dibenzothiophene The following are all of the following: benzo[a]dibenzothiophene, pyrrole, indolyl, carbazolyl, oxazolyl, benzo[a]oxazolyl, dibenzo[a]oxazolyl, thiazolyl, benzo[a]thiazolyl, dibenzo[a]thiazolyl, imidazolyl, benzo[a]imidazolyl, dibenzo[a]imidazolyl, quinolinyl, benzo[a]quinolinyl, isoquinolinyl, benzo[a]isoquinolinyl, quinazolinyl, benzo[a]quinazolinyl, quinoxalinyl, benzo[a]quinoxalinyl, phenanthiazolyl, naphridinyl, acridineyl, phenoxazinyl, phenthiazolyl; b1 is selected from 0, 1, 2, 3, 4 or 5; b2 is selected from 0, 1, 2, 3 or 4; b3 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; b4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; b5 is selected from 0, 1, 2 or 3; b6 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; b7 is selected from 0, 1, 2, 3, 4, 5 or 6; when there are two or more R2s, the two or more R2s are the same as or different from each other.

[0074] More preferably, the Ar2 is selected from any one of the following groups: .

[0075] Preferably, the Ar3 is selected from any one of the following groups:

[0076] The u is independently selected from any one of CH and N atoms; when u is bonded to other groups, the u is selected from C atoms. The ring C is selected from substituted or unsubstituted C3~C10 alicyclic rings; X1 and X2 are independently selected from O, S, and N(R). s Any one of the following; X3, X4, and X5 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 sIt is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl; 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'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 are the same as or different from each other.'

[0077] More preferably, the Ar3 is selected from any one of the following groups:

[0078] The R c R c 'Independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, nitro, 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, benzocyclobutenyl, benzocyclopentenyl Benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthraceneyl, phenanthrene, pyrene, perylene, phenylene, acenaphthene, fluoranyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thiopheneyl, benzothiopheneyl, dibenzothiopheneyl, benzodibenzothiopheneyl, pyrroleyl 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 p R qThe group is independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, nitro, and substituted or unsubstituted groups of the following: methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, 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, pyrene, peryl, phenyl, acenaphthene, fluoranyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl; The R s The following groups are independently selected from hydrogen, deuterium, substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenyl Any one of the following: silyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl; The c1 is selected from 0, 1, 2, 3, 4, or 5; the c2 is selected from 0, 1, 2, 3, or 4; the c3 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; the c4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; the c5 is selected from 0, 1, or 2; the c6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; the c7 is selected from 0, 1, 2, or 3; the c8 is selected from 0, 1, 2, 3, 4, 5, or 6; the c9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the c 10 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, or 13; 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 Rc They connect with each other to form substituted or unsubstituted rings; c'1 is selected from 0, 1, or 2; c'2 is selected from 0, 1, 2, 3, or 4; c'3 is selected from 0, 1, 2, 3, 4, 5, or 6; c'4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; c'5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; when there are two or more R... c At that time, two or more R c 'They are the same as or different from each other.'

[0079] More preferably, the Ar3 is selected from any one of the following groups:

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095] 。

[0096] Preferably, L1, L2, and L3 are independently selected from single bonds or any one of the following groups, or a combination of two or more of the following groups:

[0097] The r is independently selected from any one of CH and N atoms, and 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 D 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-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl; The 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 Re 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.'

[0098] More preferably, L1, L2, and L3 are independently selected from single bonds or any one of the following groups, or a combination of two or more of the following groups:

[0099] The R e R e '、R i R j The group is independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, and substituted or unsubstituted groups of the following: methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentene. Benzyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthraceneyl, phenanthrene, pyrene, perylene, phenylene, acenaphthene, fluoranyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thiopheneyl, benzothiopheneyl, dibenzothiopheneyl, benzodibenzothiopheneyl, pyrroleyl, Any one of the following: indolyl, carbazolyl, oxazolyl, benzoxazolyl, dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzoimidazolyl, dibenzoimidazolyl, quinolinyl, benzoquinolinyl, isoquinolinyl, benzoisoquinolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenantholinyl, naphridyl, acridineyl, phenoxazinyl, phenothiazinyl; The R kSelected from hydrogen, deuterium, and the following substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetramethylsilyl, etc. The following is a list of compounds: pyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthraceneyl, phenanthrene, pyrene, peryl, phenyl, acenaphthene, fluoranyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, and triazinyl. The value of e1 is selected from 0, 1, 2, 3, or 4; the value of e2 is selected from 0, 1, 2, 3, 4, 5, or 6; the value of e3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the value of e4 is selected from 0, 1, or 2; the value of e5 is selected from 0, 1, 2, or 3; the value of e6 is selected from 0, 1, 2, 3, 4, or 5; the value of e7 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; when there are two or more R... e At that time, two or more R e The same or different between each other, or two adjacent R e They connect with each other to form substituted or unsubstituted rings; The term e'1 is selected from 0, 1, or 2; the term e'2 is selected from 0, 1, 2, 3, or 4; the term e'3 is selected from 0, 1, 2, 3, 4, 5, or 6; the term e'4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the term e'5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; when there are two or more R... e At that time, two or more R e 'They are the same as or different from each other.'

[0100] More preferably, L1, L2, and L3 are independently selected from single bonds or any one of the following groups, or a combination of two or more of the following groups:

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114] .

[0115] Most preferably, formula I is selected from any of the following structures:

[0116]

[0117]

[0118] .

[0119] 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.

[0120] 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.

[0121] 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.

[0122] Preferably, the hole transport region includes at least one of a hole injection layer, a hole transport layer, and an electron blocking layer.

[0123] 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.

[0124] 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.

[0125] Preferably, the light-emitting layer comprises a host material and a dopant material.

[0126] Preferably, the electron transport region comprises at least one of an electron injection layer, an electron transport layer, and a hole blocking layer.

[0127] 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.

[0128] The anode of the present invention is preferably made of a material with a high work function. The anode can be a transmission electrode, a reflection electrode, or a semi-transmission electrode. Specific examples of the anode material include, but are not limited to, 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, but are not limited to, poly[3,4-(ethylene-1,2-dioxothiophene)] (PEDOT), polypyrrole (PPY), and polyaniline (PANI).

[0129] The hole injection layer described in this invention is preferably made of a material with high hole injection capability. It may include metal compounds, quinone derivatives, phthalocyanine derivatives, perylene derivatives, polymers, triarylamine compounds, axialene compounds, and other substances with high hole injection capability. Specific examples include, but are not limited to, 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), 4,4',4''-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4”-tris(N-3-methylphenyl-N-phenylamino)triphenylamine (m-MTDATA), molybdenum trioxide (MoO3), vanadium pentoxide (V2O5), and trioxide... Tungsten oxide (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), tetracyanoquinone dimethyl ether (TCNQ), 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanoquinone-dimethyl ether (F4-TCNQ), etc.

[0130] The hole transport layer described in this invention is preferably made of a material with high hole transport properties. This material may include carbazole derivatives, fluorene derivatives, aromatic amine derivatives, biphenyl diamine 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, 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), N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), 2,2,7,7-tetra(diphenylamino)-9,9-spirodifluorene (Spiro-TAD), and 4,4',4”-tris(carbazole-9-yl)triphenylamine (TCTA), etc.

[0131] The electron blocking layer of 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 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), etc., but are not limited thereto.

[0132] The luminescent layer described in this invention can use red, green, or blue luminescent materials, typically comprising a single material, a host material (also called a matrix material), and a dopant material (also called a guest material). The luminescent layer material can contain multiple host materials and multiple dopant materials. The host material of the luminescent layer needs to possess bipolar charge transport properties and appropriate energy levels to effectively transfer excitation energy to the guest luminescent material. The host material of the luminescent layer can include fused aromatic ring derivatives, heterocyclic compounds, etc. Fused aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene derivatives, fluoranthene derivatives, etc., and heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, pyrimidine derivatives, etc., such as Alq3, BAlq, TPBi, TPD, CBP, TCTA, ADN, etc., but are not limited to these. The dopant material of the luminescent layer can be a fluorescent material, a phosphorescent material, or a TADF material. Fluorescent doped 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 doped materials may include: heavy metal complexes, phosphorescent rare-earth metal complexes, etc., such as FIrpic, Ir(ppy)3, Ir(ppy)2(acac), etc., but are not limited to these.

[0133] The hole-blocking layer of this invention preferably possesses good electron transport performance and is made of materials that block or restrict hole transport. These materials may include triazine derivatives, quinoline derivatives, oxazole derivatives, benzoxazole derivatives, thiazole derivatives, benzothiazole derivatives, imidazole derivatives, benzimidazole derivatives, phenanthroline derivatives, aluminum complexes, lithium complexes, beryllium complexes, polymers, rare earth derivatives, diazoxide-phenanthroline derivatives, azabenzene derivatives, anthrone derivatives, etc. Specific examples of the hole-blocking layer materials include, but are not limited to, BAlq, BCP, and TPBi.

[0134] The electron transport layer described in this invention is preferably made of a material with high electron transport properties, and can be a single-layer or multi-layer structure. 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.

[0135] 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), magnesium phosphide (MgP), cesium carbonate (Cs₂CO₃), lithium oxide (Li₂O), lithium boron oxide (LiBO₂), aluminum oxide (Al₂O₃), vanadium oxide (V₂O₅), lithium fluoride (LiF), lithium oxide (Li₂O), and cesium fluoride (CsF).

[0136] 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, magnesium-silver alloys (Mg:Al), lithium-aluminum alloys (Li:Al), calcium / silver (Ca / Ag), aluminum (Al), silver (Ag), gold (Au), lead (Pb), lithium (Li), magnesium (Mg), ytterbium (Yb), and calcium (Ca).

[0137] 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, lithium fluoride (LiF), magnesium fluoride (MgF2), aluminum(III)tris(8-hydroxyquinoline)alcohol(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), etc. The carbazole compound of this invention is preferred.

[0138] 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.

[0139] [Synthesis Route]

[0140] Preparation of compound I: or

[0141] Xa, Xb, Xc, and Xd are each independently selected from any one of Cl, Br, and I; the limitations of Ar1, Ar2, Ar3, L1, L2, L3, and i are the same as those described above.

[0142] 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.

[0143] 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.

[0144] Synthesis Example 1: Preparation of Compound 219

[0145] Preparation of intermediate A-219

[0146] Under nitrogen protection, a-219 (22.51 g, 90 mmol), b-219 (25.25 g, 90 mmol), and K₂CO₃ (24.88 g, 180.00 mmol) were dissolved in 450 mL of toluene / ethanol / water (2:1:1). Pd(dppf)Cl₂ (1.32 g, 1.80 mmol) was added with stirring, and the mixture was heated under reflux for 5.0 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-219 (31.05 g, 85% yield); HPLC purity ≥ 99.79%. Mass spectrometry m / z: 405.1044 (theoretical value: 405.1033).

[0147] Preparation of intermediate B-219

[0148] Under argon protection, A-219 (24.35 g, 60.00 mmol), c-219 (14.89 g, 60.00 mmol), K2CO3 (12.44 g, 90.00 mmol), and 500 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 (0.69 g, 0.60 mmol) was added. The mixture was stirred, and the system was heated under reflux for 6.0 hours. After the reaction was completed, the mixture was cooled to room temperature, distilled water was added, and the toluene layer was separated and dried with anhydrous magnesium sulfate. The solvent was concentrated by rotary evaporation after filtration, and crystals were precipitated by cooling and filtration. The crystals were then recrystallized from toluene / methanol at a ratio of 10:1 to obtain intermediate B-219 (26.16 g, yield 76%) with an HPLC purity ≥99.87%. Mass spectrometry m / z: 573.2221 (theoretical value: 573.2205).

[0149] Preparation of compound 219

[0150] Under nitrogen protection, B-219 (22.95 g, 40.00 mmol), d-219 (11.89 g, 40.00 mmol), and sodium tert-butoxide (5.77 g, 60.00 mmol) dissolved in 180 mL of toluene were added to a reaction flask with stirring. Pd₂(dba)₃ (0.37 g, 0.40 mmol) and X-Phos (0.38 g, 0.80 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 219 (23.07 g, 73% yield). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 789.2796 (theoretical value: 789.2780). Theoretical elemental content (%) C 58 H 35 N3O: C, 88.19; H, 4.47; N, 5.32. Measured elemental content (%): C, 88.21; H, 4.50; N, 5.35.

[0151] Synthesis Example 2: Preparation of Compound 247

[0152] According to the preparation method in Synthesis Example 1, c-219 was replaced with an equimolar amount of c-247, and d-219 was replaced with an equimolar amount of d-247 to obtain compound 247 (24.19 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 839.2925 (theoretical value: 839.2937). Theoretical elemental content (%) C 62 H 37 N3O: C, 88.65; H, 4.44; N, 5.00. Measured elemental content (%): C, 88.62; H, 4.42; N, 4.98.

[0153] Synthesis Example 3: Preparation of Compound 272

[0154] According to the preparation method in Example 1, c-219 was replaced with an equimolar amount of c-272, and d-219 was replaced with an equimolar amount of d-247, yielding compound 272 (22.79 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 813.2768 (theoretical value: 813.2780). Theoretical elemental content (%) C 60 H 35 N3O: C, 88.54; H, 4.33; N, 5.16. Measured elemental content (%): C, 88.51; H, 4.30; N, 5.13.

[0155] Synthesis Example 4: Preparation of Compound 281

[0156] According to the preparation method in Synthesis Example 1, a-219 was replaced with an equimolar amount of a-281, c-219 was replaced with an equimolar amount of c-281, and d-219 was replaced with an equimolar amount of d-281, yielding compound 281 (23.12 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 813.2767 (theoretical value: 813.2780). Theoretical elemental content (%) C 60 H 35 N3O: C, 88.54; H, 4.33; N, 5.16. Measured element content (%): C, 88.52; H, 4.31; N, 5.14.

[0157] Synthesis Implementation 5: Preparation of Compound 291

[0158] Preparation of intermediate C-291

[0159] Under nitrogen protection, f-291 (38.42 g, 150.00 mmol), g-291 (36.38 g, 150.00 mmol), potassium carbonate (41.46 g, 300.00 mmol), tetrakis(triphenylphosphine)palladium (2.08 g, 1.80 mmol), and 750 mL of a 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 4 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 over anhydrous magnesium sulfate, and the solvent was concentrated by rotary evaporation. Crystallization was carried out under cooling and filtered. The resulting solid was recrystallized from toluene to give intermediate C-291 (38.07 g, yield 87%); HPLC purity ≥ 99.68%. Mass spectrometry m / z: 291.0579 (theoretical value: 291.0563).

[0160] Preparation of intermediate a-291

[0161] Under nitrogen protection, C-291 (35.01 g, 120.00 mmol), h-291 (30.47 g, 120.00 mmol), Pd(dppf)Cl2 (0.33 g, 0.45 mmol), potassium acetate (17.67 g, 180.00 mmol), and DMF (450 ml) were added to the reaction flask, and the mixture was stirred under reflux for 6 hours. After the reaction was completed, the mixture was cooled to room temperature, the solvent was removed under reduced pressure, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure, and the mixture was recrystallized from toluene:ethanol = 3:1 to give intermediate a-291 (38.17 g, yield 83%); HPLC purity ≥ 99.73%. Mass spectrometry m / z: 383.1817 (theoretical value: 383.1805).

[0162] According to the preparation method in Example 1, a-219 was replaced with an equimolar amount of a-291, c-219 with an equimolar amount of c-291, and d-219 with an equimolar amount of d-291, yielding compound 291 (23.45 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 802.2748 (theoretical value: 802.2733). Theoretical elemental content (%) C 58 H 34 N4O: C, 86.76; H, 4.27; N, 6.98. Measured elemental content (%): C, 86.74; H, 4.23; N, 6.97.

[0163] Synthesis Example 6: Preparation of Compound 296

[0164] According to the preparation method in Example 1, c-219 was replaced with an equimolar amount of c-296, and d-219 was replaced with an equimolar amount of d-247, yielding compound 296 (24.65 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 855.3240 (theoretical value: 855.3250). Theoretical elemental content (%) C 63 H 41 N3O: C, 88.39; H, 4.83; N, 4.91. Measured elemental content (%): C, 88.37; H, 4.81; N, 4.89.

[0165] Synthesis Example 7: Preparation of Compound 307

[0166] According to the preparation method in Synthesis Example 1, c-219 was replaced with an equimolar amount of c-307, and d-219 was replaced with an equimolar amount of d-307 to obtain compound 307 (21.93 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 740.2589 (theoretical value: 740.2576). Theoretical elemental content (%) C 53 H 32 N4O: C, 85.92; H, 4.35; N, 7.56. Measured elemental content (%): C, 85.96; H, 4.39; N, 7.60.

[0167] Synthesis Example 8: Preparation of Compound 329

[0168] According to the preparation method in Synthesis Example 1, c-219 was replaced with an equimolar amount of a-219, and d-219 was replaced with an equimolar amount of d-247, yielding compound 329 (23.76 g). HPLC analysis showed a solid purity ≥ 99.99%. Mass spectrometry m / z: 791.2672 (theoretical value: 791.2685). Theoretical elemental content (%) C 56 H 33 N5O: C, 84.94; H, 4.20; N, 8.84. Measured elemental content (%): C, 84.98; H, 4.24; N, 8.88.

[0169] Synthesis Example 9: Preparation of Compound 413

[0170] According to the preparation method in Synthesis Example 1, c-219 was replaced with an equimolar amount of c-413, and d-219 was replaced with an equimolar amount of d-413, yielding compound 413 (23.62 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 797.2235 (theoretical value: 797.2249). Theoretical elemental content (%) C 54 H 31 N5OS: C, 81.28; H, 3.92; N, 8.78. Measured elemental content (%): C, 81.25; H, 3.93; N, 8.77.

[0171] Synthesis Example 10: Preparation of Compound 423

[0172] According to the preparation method in Synthesis Example 1, c-219 was replaced with an equimolar amount of c-423, and d-219 was replaced with an equimolar amount of d-423 to obtain compound 423 (24.73 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 846.2466 (theoretical value: 846.2453). Theoretical elemental content (%) C 59 H 34 N4OS: C, 83.66; H, 4.05; N, 6.61. Measured elemental content (%): C, 83.69; H, 4.08; N, 6.64.

[0173] Synthetic Example 11: Preparation of Compound 441

[0174] According to the preparation method in Synthesis Example 1, c-219 was replaced with an equimolar amount of c-441, and d-219 was replaced with an equimolar amount of d-247, yielding compound 441 (23.15 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 803.2560 (theoretical value: 803.2573). Theoretical elemental content (%) C 58 H 33 N3O2: C, 86.66; H, 4.14; N, 5.23. Measured elemental content (%): C, 86.62; H, 4.10; N, 5.19.

[0175] Synthesis Example 12: Preparation of Compound 454

[0176] According to the preparation method in Synthesis Example 1, a-219 was replaced with an equimolar amount of a-454, b-219 with an equimolar amount of b-454, c-219 with an equimolar amount of c-454, and d-219 with an equimolar amount of d-454, yielding compound 454 (24.99 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 879.2985 (theoretical value: 879.2998). Theoretical elemental content (%) C 63 H 37 N5O: C, 85.99; H, 4.24; N, 7.96. Measured elemental content (%): C, 85.96; H, 4.21; N, 7.93.

[0177] Synthesis Example 13: Preparation of Compound 458

[0178] According to the preparation method in Example 1, a-219 was replaced with an equimolar amount of a-458, c-219 was replaced with an equimolar amount of c-458, and d-219 was replaced with an equimolar amount of d-458, yielding compound 458 (26.07 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 917.3030 (theoretical value: 917.3042). Theoretical elemental content (%) C 67 H 39 N3O2: C, 87.66; H, 4.28; N, 4.58. Measured elemental content (%): C, 87.62; H, 4.24; N, 4.54.

[0179] Synthesis Example 14: Preparation of Compound 460

[0180] According to the preparation method in Synthesis Example 1, a-219 was replaced with an equimolar amount of a-460, c-219 was replaced with an equimolar amount of a-460, and d-219 was replaced with an equimolar amount of d-247, yielding compound 460 (30.07 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 1043.3611 (theoretical value: 1043.3624). Theoretical elemental content (%) C 76 H 45 N5O: C, 87.42; H, 4.34; N, 6.71. Measured elemental content (%): C, 87.39; H, 4.31; N, 6.68.

[0181] Synthetic Example 15: Preparation of Compound 515

[0182] According to the preparation method in Synthesis Example 1, a-219 was replaced with an equimolar amount of a-515, c-219 was replaced with an equimolar amount of c-515, and d-219 was replaced with an equimolar amount of d-515, yielding compound 515 (22.31 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 763.2636 (theoretical value: 763.2624). Theoretical elemental content (%) C 56 H 33 N3O: C, 88.05; H, 4.35; N, 5.50. Measured elemental content (%): C, 88.09; H, 4.39; N, 5.54.

[0183] Synthesis Example 16: Preparation of Compound 576

[0184] According to the preparation method in Synthesis Example 1, a-219 was replaced with an equimolar amount of a-515, c-219 was replaced with an equimolar amount of a-515, and d-219 was replaced with an equimolar amount of d-576, yielding compound 576 (22.81 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 791.2673 (theoretical value: 791.2685). Theoretical elemental content (%) C 56 H 33 N5O: C, 84.94; H, 4.20; N, 8.84. Measured elemental content (%): C, 84.91; H, 4.17; N, 8.81.

[0185] Synthesis Example 17: Preparation of Compound 628

[0186] According to the preparation method in Synthesis Example 1, a-219 was replaced with an equimolar amount of a-515, c-219 was replaced with an equimolar amount of c-628, and d-219 was replaced with an equimolar amount of d-628, yielding compound 628 (22.80 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 780.2537 (theoretical value: 780.2525). Theoretical elemental content (%) C 55 H 32 N4O2: C, 84.60; H, 4.13; N, 7.17. Measured elemental content (%): C, 84.66; H, 4.17; N, 7.23.

[0187] Synthesis Example 18: Preparation of Compound 863

[0188] According to the preparation method in Synthesis Example 1, b-219 was replaced with an equimolar amount of b-863, c-219 was replaced with an equimolar amount of c-863, and d-219 was replaced with an equimolar amount of d-247, yielding compound 863 (21.71 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 753.2409 (theoretical value: 753.2416). Theoretical elemental content (%) C 54 H 31 N3O2: C, 86.04; H, 4.15; N, 5.57. Measured elemental content (%): C, 86.02; H, 4.12; N, 5.54.

[0189] Synthesis Example 19: Preparation of Compound 869

[0190] According to the preparation method in Example 1, c-219 was replaced with an equimolar amount of c-869, and d-219 was replaced with an equimolar amount of d-247, yielding compound 869 (23.56 g). HPLC analysis showed a solid purity ≥ 99.99%. Mass spectrometry m / z: 795.3266 (theoretical value: 795.3250). Theoretical elemental content (%) C 58 H 41 N3O: C, 87.52; H, 5.19; N, 5.28. Measured elemental content (%): C, 87.57; H, 5.24; N, 5.31.

[0191] Synthesis Example 20: Preparation of Compound 882

[0192] According to the preparation method in Example 1, a-219 was replaced with an equimolar amount of a-882, c-219 was replaced with an equimolar amount of c-882, and d-219 was replaced with an equimolar amount of d-882, yielding compound 882 (23.91 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 807.2699 (theoretical value: 807.2686). Theoretical elemental content (%) C 58 H 34 FN3O: C, 86.23; H, 4.24; N, 5.20. Measured elemental content (%): C, 86.26; H, 4.27; N, 5.22.

[0193] Synthesis Example 21: Preparation of Compound 891

[0194] According to the preparation method in Synthesis Example 1, c-219 was replaced with an equimolar amount of c-891, and d-219 was replaced with an equimolar amount of d-247, yielding compound 891 (23.71 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 811.3030 (theoretical value: 811.3019). Theoretical elemental content (%) C 57 H 41 N3OSi: C, 84.31; H, 5.09; N, 5.17. Measured elemental content (%): C, 84.35; H, 5.13; N, 5.21.

[0195] Synthesis Example 22: Preparation of Compound 922

[0196] According to the preparation method in Synthesis Example 1, b-219 was replaced with an equimolar amount of b-922, c-219 was replaced with an equimolar amount of a-219, and d-219 was replaced with an equimolar amount of d-247, yielding compound 922 (23.30 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 797.3073 (theoretical value: 797.3062). Theoretical elemental content (%) C 56 H 27 D6N5O: C, 84.29; H, 4.93; N, 8.78. Measured elemental content (%): C, 84.33; H, 4.95; N, 8.82.

[0197] Synthesis Example 23: Preparation of Compound 936

[0198] According to the preparation method in Example 1, c-219 was replaced with an equimolar amount of c-936, and d-219 was replaced with an equimolar amount of d-936, yielding compound 936 (24.77 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 859.3515 (theoretical value: 859.3501). Theoretical elemental content (%) C 63 H 37 D4N3O: C, 87.98; H, 5.27; N, 4.89. Measured elemental content (%): C, 87.96; H, 5.25; N, 4.87.

[0199] Synthesis Example 24: Preparation of Compound 940

[0200] According to the preparation method in Synthesis Example 1, a-219 was replaced with an equimolar amount of a-940, c-219 was replaced with an equimolar amount of c-940, and d-219 was replaced with an equimolar amount of d-940, yielding compound 940 (25.20 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 874.3559 (theoretical value: 874.3548). Theoretical elemental content (%) C 63 H 30 D8N4O: C, 86.47; H, 5.30; N, 6.40. Measured elemental content (%): C, 86.49; H, 5.34; N, 6.42.

[0201] Synthesis Example 25: Preparation of Compound 996

[0202] According to the preparation method in Synthesis Example 1, a-219 was replaced with an equimolar amount of a-515, b-219 with an equimolar amount of b-996, c-219 with an equimolar amount of a-515, and d-219 with an equimolar amount of d-996, yielding compound 996 (20.89 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 705.1972 (theoretical value: 705.1987). Theoretical elemental content (%) C 48 H 27 N5S: C, 81.68; H, 3.86; N, 9.92. Measured elemental content (%): C, 81.70; H, 3.88; N, 9.95.

[0203] Synthesis Example 26: Preparation of Compound 1048

[0204] Preparation of intermediate a-1048

[0205] According to the preparation method in Synthesis Example 5, g-291 was replaced with an equimolar amount of g-1048 to obtain synthetic intermediate a-1048 (32.48 g, 81%). The purity of the solid was ≥99.66% as determined by HPLC. Mass spectrometry m / z: 334.1618 (theoretical value: 334.1601).

[0206] According to the preparation method in Synthesis Example 1, a-219 was replaced with an equimolar amount of a-1048, b-219 with an equimolar amount of b-1048, c-219 with an equimolar amount of c-1048, and d-219 with an equimolar amount of d-1048, yielding compound 1048 (24.38 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 834.2551 (theoretical value: 834.2566). Theoretical elemental content (%) C 57 H 34 N6S: C, 81.99; H, 4.10; N, 10.06. Measured elemental content (%): C, 81.97; H, 4.14; N, 10.08.

[0207] Synthesis Example 27: Preparation of Compound 1102

[0208] According to the preparation method in Example 1, a-219 was replaced with an equimolar amount of a-1102, c-219 was replaced with an equimolar amount of c-1102, and d-219 was replaced with an equimolar amount of d-1102, yielding compound 1102 (28.32 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 996.3278 (theoretical value: 996.3287). Theoretical elemental content (%) C 72 H 44 N4S: C, 86.72; H, 4.45; N, 5.62. Measured elemental content (%): C, 86.73; H, 4.49; N, 5.65.

[0209] Synthesis Example 28: Preparation of Compound 1105

[0210] According to the preparation method in Synthesis Example 1, b-219 was replaced with an equimolar amount of b-1105, c-219 was replaced with an equimolar amount of c-1105, and d-219 was replaced with an equimolar amount of d-1102, yielding compound 1105 (26.65 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 937.3478 (theoretical value: 937.3491). Theoretical elemental content (%) C 68 H 47 N3S: C, 87.05; H, 5.05; N, 4.48. Measured elemental content (%): C, 87.01; H, 5.03; N, 4.44.

[0211] Synthesis Example 29: Preparation of Compound 1142

[0212] According to the preparation method in Synthesis Example 1, a-219 was replaced with an equimolar amount of a-1142, c-219 was replaced with an equimolar amount of a-1142, and d-219 was replaced with an equimolar amount of d-1142, yielding compound 1142 (23.92 g). HPLC analysis showed a solid purity ≥ 99.99%. Mass spectrometry m / z: 807.2466 (theoretical value: 807.2457). Theoretical elemental content (%) C 56 H 33 N5S: C, 83.25; H, 4.12; N, 8.67. Measured elemental content (%): C, 83.21; H, 4.11; N, 8.65.

[0213] Synthesis Example 30: Preparation of Compound 1170

[0214] According to the preparation method in Example 1, c-219 was replaced with an equimolar amount of c-1170, and d-219 was replaced with an equimolar amount of d-1102, yielding compound 1170 (24.83 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 861.2255 (theoretical value: 861.2272). Theoretical elemental content (%) C 60 H 35 N3S2: C, 83.60; H, 4.09; N, 4.87. Measured elemental content (%): C, 83.58; H, 4.06; N, 4.85.

[0215] Synthesis Example 31: Preparation of Compound 1183

[0216] According to the preparation method in Synthesis Example 1, a-219 was replaced with an equimolar amount of a-1183, b-219 with an equimolar amount of b-1183, c-219 with an equimolar amount of c-1183, and d-219 with an equimolar amount of d-1102, yielding compound 1183 (22.90 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 794.2516 (theoretical value: 794.2504). Theoretical elemental content (%) C 56 H 34 N4S: C, 84.61; H, 4.31; N, 7.05. Measured elemental content (%): C, 84.65; H, 4.36; N, 7.08.

[0217] Synthesis Example 32: Preparation of Compound 1192

[0218] According to the preparation method in Synthesis Example 1, c-219 was replaced with an equimolar amount of c-1192, and d-219 was replaced with an equimolar amount of d-1102, yielding compound 1192 (22.04 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 786.1926 (theoretical value: 786.1912). Theoretical elemental content (%) C 53 H 30 N4S2: C, 80.89; H, 3.84; N, 7.12. Measured elemental content (%): C, 80.84; H, 3.81; N, 7.09.

[0219] Synthesis Example 33: Preparation of Compound 1199

[0220] According to the preparation method in Synthesis Example 1, a-219 was replaced with an equimolar amount of a-1199, c-219 was replaced with an equimolar amount of c-1199, and d-219 was replaced with an equimolar amount of d-1199, yielding compound 1199 (25.34 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 904.2681 (theoretical value: 904.2694). Theoretical elemental content (%) C 62 H 40 N4S2: C, 82.27; H, 4.45; N, 6.19. Measured elemental content (%): C, 82.23; H, 4.43; N, 6.18.

[0221] Synthesis Example 34: Preparation of Compound 1316

[0222] Preparation of intermediate d-1316

[0223] Under nitrogen protection, d-1102 (33.38 g, 120.00 mmol), e-1316 (23.21 g, 120.00 mmol), potassium carbonate (33.17 g, 240.00 mmol), tetrakis(triphenylphosphine)palladium (1.66 g, 1.44 mmol), and 600 mL of a 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 over anhydrous magnesium sulfate, and the solvent was concentrated by rotary evaporation. Crystallization was carried out under cooling, and the solid was filtered. The obtained solid was recrystallized from toluene to give intermediate d-1316 (35.79 g, yield 86%); HPLC purity ≥ 99.75%. Mass spectrometry m / z: 346.0345 (theoretical value: 346.0331).

[0224] According to the preparation method in Synthesis Example 1, c-219 was replaced with an equimolar amount of c-1316, and d-219 was replaced with an equimolar amount of d-1316 to obtain compound 1316 (25.40 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 881.2626 (theoretical value: 881.2613). Theoretical elemental content (%) C 62 H 35 N5S: C, 84.43; H, 4.00; N, 7.94. Measured elemental content (%): C, 84.46; H, 4.05; N, 7.96.

[0225] Synthesis Example 35: Preparation of Compound 1367

[0226] Preparation of intermediate d-1367

[0227] According to the preparation method of Synthesis Example 34, e-1316 was replaced with an equimolar amount of e-1367 to obtain synthetic intermediate d-1367 (39.91 g, 84%). The purity of the solid was ≥99.72% as determined by HPLC. Mass spectrometry m / z: 395.0521 (theoretical value: 395.0535).

[0228] Preparation of intermediate B-1367

[0229] Under nitrogen protection, a-1367 (31.31 g, 180 mmol), b-1367 (39.70 g, 90 mmol), and K₂CO₃ (37.32 g, 270.00 mmol) were dissolved in 675 mL of toluene / ethanol / water (2:1:1). Pd(dppf)Cl₂ (1.98 g, 2.70 mmol) was added with stirring, and the mixture was heated under reflux for 5.5 h. After the reaction was complete, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from the resulting solid using toluene / ethanol in an 8:1 ratio to give intermediate B-1367 (40.31 g, yield 83%); HPLC purity ≥ 99.76%. Mass spectrometry m / z: 539.2128 (theoretical value: 539.2110).

[0230] According to the preparation method in Synthesis Example 1, B-219 was replaced with an equimolar amount of B-1367, and d-219 was replaced with an equimolar amount of d-1367 to obtain compound 1367 (25.53 g). HPLC analysis showed a solid purity ≥ 99.91%. Mass spectrometry m / z: 898.2863 (theoretical value: 898.2879). Theoretical elemental content (%) C 62 H 38 N6S: C, 82.83; H, 4.26; N, 9.35. Measured elemental content (%): C, 82.84; H, 4.23; N, 9.37.

[0231] Synthesis Example 36: Preparation of Compound 1377

[0232] According to the preparation method in Synthesis Example 1, c-219 was replaced with an equimolar amount of c-1377, and d-219 was replaced with an equimolar amount of d-1377, yielding compound 1377 (25.64 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 889.3475 (theoretical value: 889.3491). Theoretical elemental content (%) C 64 H 47N3S: C, 86.36; H, 5.32; N, 4.72. Measured elemental content (%): C, 86.33; H, 5.34; N, 4.69.

[0233] Synthesis Example 37: Preparation of Compound 1382

[0234] According to the preparation method in Synthesis Example 1, c-219 was replaced with an equimolar amount of c-1382, and d-219 was replaced with an equimolar amount of d-1102, yielding compound 1382 (24.39 g). HPLC analysis showed a solid purity ≥ 99.99%. Mass spectrometry m / z: 823.2281 (theoretical value: 823.2269). Theoretical elemental content (%) C 55 H 32 F3N3S: C, 80.18; H, 3.91; N, 5.10. Measured elemental content (%): C, 80.23; H, 3.92; N, 5.13.

[0235] Synthesis Example 38: Preparation of Compound 1392

[0236] According to the preparation method in Synthesis Example 1, c-219 was replaced with an equimolar amount of c-1392, and d-219 was replaced with an equimolar amount of d-1102, yielding compound 1392 (22.64 g). HPLC analysis showed a solid purity ≥ 99.99%. Mass spectrometry m / z: 764.2977 (theoretical value: 764.2960). Theoretical elemental content (%) C 54 H 24 D9N3S: C, 84.78; H, 5.53; N, 5.49. Measured elemental content (%): C, 84.82; H, 5.56; N, 5.51.

[0237] Synthesis Example 39: Preparation of Compound 1410

[0238] According to the preparation method in Synthesis Example 1, a-219 was replaced with an equimolar amount of a-1410, c-219 was replaced with an equimolar amount of a-1410, and d-219 was replaced with an equimolar amount of d-1102, yielding compound 1410 (23.56 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 817.3071 (theoretical value: 817.3084). Theoretical elemental content (%) C 56 H 23 D 10N5S: C, 82.22; H, 5.30; N, 8.56. Measured elemental content (%): C, 82.20; H, 5.33; N, 8.54.

[0239] [Device Examples]

[0240] 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.

[0241] [Example 1]

[0242] The glass substrate was cleaned using distilled water and ultrasonic cleaning. After distilled water washing, ultrasonic cleaning was performed using solvents such as isopropanol, acetone, and methanol, followed by drying. After drying, the substrate was transferred to a plasma cleaner, and then transferred to an evaporation deposition machine. ITO / Ag / ITO was coated on the glass substrate to form an anode. HI-1:HT-1 (mass ratio 3:97) was deposited on the anode to form a hole injection layer with a thickness of 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, with GH-1 as the host material and 6 wt% GD-1 doped, forming a light-emitting layer with a thickness of 350 Å. HB-1 was deposited on the light-emitting layer to form a hole blocking layer with a thickness of 100 Å. ET-1:LiQ (mass ratio 1:1) was deposited on the hole blocking layer to form an electron transport layer with a thickness of 300 Å. LiF is deposited on the electron transport layer to form an electron injection layer with a thickness of 10 Å. Mg:Ag (mass ratio 1:9) is then deposited on the electron injection layer to form a cathode with a thickness of 150 Å. Compound 219 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.

[0243]

[0244] [Examples 2-39]

[0245] Compounds 247, 272, 281, 291, 296, 307, 329, 413, 423, 441, 454, 458, 460, 515, 576, 628, 863, 869, 882, 891, 922, 936, 940, 996, 1048, 1102, 1105, 1142, 1170, 1183, 1192, 1199, 1316, 1367, 1377, 1382, 1392, and 1410 of this invention were used to replace compound 219 in Example 1 as the capping layer material. Otherwise, an organic electroluminescent device was prepared using the same preparation method as in Example 1.

[0246] [Comparative Examples 1-3]

[0247] Organic electroluminescent devices were prepared by replacing compound 219 in Example 1 with compounds P-1, P-2, and P-3, respectively, using the same preparation method as in Example 1.

[0248] The test environment was atmospheric, and the temperature was room temperature. The luminescence characteristics test results of the organic electroluminescent devices obtained by devices 1-39 in the embodiments of the present invention and comparative examples 1-3 are shown in Table 1 below.

[0249] Table 1:

[0250]

[0251] As shown in Table 1, when the carbazole compound of the present invention is applied to the capping layer of an organic electroluminescent device, the device exhibits higher luminous efficiency and longer lifespan compared to comparative compounds P-1 to P-3. The carbazole compound of the present invention is a high-performance capping layer material.

[0252] 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, i is independently selected from C(R) i ); The R i It is independently selected from any one of hydrogen, deuterium, fluorine, cyano, substituted or unsubstituted C1 to C6 alkyl groups; The Ar1 is selected from any one of the following groups: X is independently selected from either O or S; The z is selected from either CH or N, and at most one z in each group is selected from an N atom; The R t The group is independently selected from hydrogen, deuterium, fluorine, cyano, or any of the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, and isohexyl. 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 are the same as or different from each other; The Ar2 group is selected from any one of the following groups: The R2 is independently selected from hydrogen, deuterium, fluorine, cyano, or any one of the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, and phenyl. The value of b1 is selected from 0, 1, 2, 3, 4 or 5; when there are two or more R2, the two or more R2 are the same as or different from each other; The Ar3 group is selected from any one of the following groups: The R c R c 'Independently selected from hydrogen, deuterium, fluorine, or any of the following groups, whether substituted or unsubstituted: methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, and phenyl; The R p R q The group is independently selected from any one of the following groups, whether substituted or unsubstituted: methyl, ethyl, propyl, butyl, pentyl, hexyl, phenyl, biphenyl, and naphthyl; The R s The group is independently selected from any one of the following groups, whether substituted or unsubstituted: phenyl, biphenyl, or naphthyl; 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 They are the same as or different from each other; c'1 is selected from 0, 1, or 2; c'2 is selected from 0, 1, 2, 3, or 4; c'3 is selected from 0, 1, 2, 3, 4, 5, or 6; c'4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; c'5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; when there are two or more R... c At that time, two or more R c 'They may be the same as or different from each other; The L1, L2, and L3 are independently selected from single bonds or any one of the following groups: The R e The group is independently selected from hydrogen, deuterium, fluorine, or any of the following groups, whether substituted or unsubstituted: methyl, ethyl, propyl, butyl, pentyl, hexyl, and phenyl. 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 e4 is selected from 0, 1, or 2; the value of e5 is selected from 0, 1, 2, or 3; the value of e6 is selected from 0, 1, 2, 3, 4, or 5; 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; The substituents in "substituted or unsubstituted" are independently selected from deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, propyl, and butyl.

2. The carbazole compound according to claim 1, characterized in that, The Ar1 is selected from any one of the following groups: 。 3. The carbazole compound according to claim 1, characterized in that, The R2 is independently selected from hydrogen, deuterium, fluorine, or any of the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, and phenyl.

4. A carbazole compound according to claim 1, characterized in that, The Ar3 group is selected from any one of the following groups: The R c R c 'Independently selected from hydrogen, deuterium, fluorine, or any of the following substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, adamantyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, and phenyl.' 5. A carbazole compound according to claim 1, characterized in that, The L1, L2, and L3 are independently selected from single bonds or any one of the following groups: The R e The group is independently selected from hydrogen, deuterium, fluorine, or any of the following groups, whether substituted or unsubstituted: methyl, ethyl, propyl, butyl.

6. A carbazole compound, characterized in that, The carbazole compound is selected from any one of the following structures: 。 7. 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 6.

8. An organic electroluminescent device according to claim 7, 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 6.

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