A compound containing a nitrogen-containing fused aromatic ring and an organic electroluminescent device thereof

Abstract

The application provides a nitrogen-containing fused aromatic ring compound and an organic electroluminescent device thereof, and relates to the technical field of organic electroluminescent materials. In order to solve the problems existing in the prior art of organic electroluminescent materials and devices, the application provides a nitrogen-containing fused aromatic ring compound, which is applied to an organic electroluminescent device as a host material of an electron transport layer, a hole blocking layer and a light-emitting layer, so that the luminous efficiency, driving voltage and service life of the device can be effectively improved. The novel nitrogen-containing fused aromatic ring organic compound has a high triplet energy level, appropriate HOMO / LUMO energy level, high electron affinity and electron mobility, is conducive to the transmission of electrons, balances the transmission of holes and electrons, and has a high decomposition temperature and glass transition temperature and good film-forming property, so that the stability and high efficiency of the device can be effectively ensured, and the luminous efficiency of the organic electroluminescent device can be significantly improved when the compound is applied to the organic electroluminescent device as a host material of a light-emitting layer.

Description

Technical Field

[0001] This invention relates to the field of organic electroluminescent materials technology, specifically to a nitrogen-containing fused aromatic ring compound and its organic electroluminescent device. Background Technology

[0002] In recent years, Organic Light Emitting Diode (OLED) displays and lighting, as a novel technology, are poised to usher in a new era due to their advantages such as wide color gamut, simple structure, soft light, fast response time, wide viewing angle, low driving voltage, and thin panel. Currently, this display technology is mainly used in mobile phones, television displays, and lighting fixtures, and is gradually expanding its market share.

[0003] As research on organic electroluminescence (OLEDs) matures, the structures of these devices become increasingly complex. However, the vast majority of OLEDs are multilayer sandwich-type dual-carrier (hole and electron) DC-DC-injected devices. They consist of a cathode, an anode, and an organic functional layer between them. These organic functional layers generally include: a hole injection layer (HIL), a hole transport layer (HTL), an emissive layer (EML), an electron transport layer (ETL), and an electron injection layer (EIL). Under the influence of an applied electric field, electrons and holes are injected from the cathode and anode, respectively. These electrons and holes are injected into the HOMO level of the electron transport layer and the LUMO level of the hole transport layer. Due to the energy difference, electrons in the HOMO level and holes in the LUMO level continuously migrate to the emissive layer, forming "hole-electron" pairs. These "hole-electron" pairs are the excitons formed by recombination. These high-energy excitons freely migrate within the emissive layer, undergoing free transitions from the excited state to the ground state. The energy of the resulting photons determines the color of the light produced.

[0004] OLEDs, as one of the most promising optoelectronic technologies of the 21st century, have made significant progress in both display and lighting fields. However, many issues regarding their luminescent performance and manufacturing technology still require further exploration. The luminescent material is an indispensable factor determining the luminous efficiency of OLEDs. Luminescent materials can be categorized into host materials and dopant materials based on their function. Obtaining an effective host material is crucial for achieving high electroluminescence efficiency. Therefore, a high-performance host material should have a higher triplet energy level than the guest material. Simultaneously, the transport of electrons and holes in the host material should be effectively balanced. However, achieving a balance of these factors within a single molecule is far from easy. Therefore, developing high-performance luminescent host materials to effectively improve the luminous efficiency, driving voltage, and lifespan of OLEDs is an urgent task.

[0005] Organic electron transport materials are organic semiconductor materials that can control the directional and orderly migration of electrons under the influence of an electric field to achieve electron transport. However, their preparation and characterization are challenging, and they suffer from low mobility and poor stability, which seriously affects the development of organic optoelectronic materials and devices. Therefore, it is crucial to develop electron transport materials with high mobility, appropriate triplet energy levels, and good thermal and chemical stability. Summary of the Invention

[0006] To address the problems existing in the prior art, the present invention provides a nitrogen-containing fused aromatic ring compound and its organic electroluminescent device, which can effectively improve the luminous efficiency, driving voltage and lifespan of OLEDs.

[0007] Specifically, the present invention provides a compound containing a nitrogen-containing fused aromatic ring, wherein the compound containing the nitrogen-containing fused aromatic ring is represented by the following formula I:

[0008]

[0009] Ar1 is selected from the group represented by formula II, wherein the ring A is selected from any one of substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C2-C60 heteroaryl;

[0010] X is selected from O, S, C(R) x )2 or N(R a );

[0011] Each of the Ts is independently selected from CH or N; the Ts fused with ring A are selected from C;

[0012] The R a It is selected from any one of substituted or unsubstituted silyl groups, substituted or unsubstituted C1-C30 alkyl groups, substituted or unsubstituted C3-C30 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic groups, and fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl groups;

[0013] The R x It is selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring;

[0014] R1 is independently selected from any one or a combination thereof, including hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl.

[0015] The R2 is independently selected from any one or a combination of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl ring.

[0016] The n1 is selected from 0, 1, or 2; the n2 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10;

[0017] Z1 to Z6 are each independently selected from C(R) y () or N, at least one of Z1 to Z6 is selected from N, and at most three of Z1 to Z6 are selected from N;

[0018] The R y It is selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring;

[0019] At least one of Ar2 and Ar3 is selected from the group shown in 1-a or 1-b, and the others are each independently selected from any one of the following: substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl ring;

[0020]

[0021] The Y is independently selected from O, S, C(R) c R d ) or N(R b );

[0022] The R c R d Each is independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring, or R c R d They connect with each other to form substituted or unsubstituted rings;

[0023] The R b It is selected from any one of substituted or unsubstituted silyl groups, substituted or unsubstituted C1-C30 alkyl groups, substituted or unsubstituted C3-C30 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic groups, and fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl groups;

[0024] The R3 is independently selected from any one or combination of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl ring, or adjacent R3s are connected to each other to form a substituted or unsubstituted ring;

[0025] The n3 is selected from 0, 1, 2, 3, 4, 5, 6 or 7;

[0026] Each of L1 to L3 is independently selected from one or a combination of single bonds, substituted or unsubstituted C6 to C60 arylene groups, substituted or unsubstituted C2 to C60 heteroarylene groups, substituted or unsubstituted C3 to C30 alicyclic and C6 to C60 aromatic groups, substituted or unsubstituted C3 to C30 alicyclic and C2 to C60 heteroaromatic groups.

[0027] The present invention also provides an organic electroluminescent device comprising an anode, a cathode, and an organic layer, wherein the organic layer comprises at least one of the nitrogen-containing fused aromatic compounds described in the present invention.

[0028] Beneficial effects

[0029] The nitrogen-containing fused aromatic ring compound of Formula I provided by this invention has a high decomposition temperature and glass transition temperature, as well as good film-forming properties and a high triplet energy level, which can effectively ensure the stability and high efficiency of the device and effectively prevent energy back-transfer from the guest material to the host material. When used as the host material of the light-emitting layer in organic electroluminescent devices, it can significantly improve the luminous efficiency and lifespan. In addition, the compound has high electrophilicity, appropriate HOMO and LUMO energy levels, and good hole blocking ability to ensure work function matching with the cathode, reduce the energy barrier between the cathode and the light-emitting layer, and effectively prevent holes in the light-emitting layer from escaping to the electron transport layer, so that electrons and holes in the light-emitting layer recombine efficiently, thereby improving the luminous efficiency of organic electroluminescent devices.

[0030] In summary, the nitrogen-containing fused aromatic ring compounds provided by this invention can effectively improve the luminous efficiency and lifespan of OLED devices when applied to them, making them a class of OLED materials with superior performance. Detailed Implementation

[0031] The technical solutions described below, in conjunction with embodiments of the present invention, will further clarify and fully illustrate the invention. Obviously, the described embodiments are merely some, not all, of the embodiments of the present invention. After reading this invention, any modifications of the present invention by those skilled in the art will fall within the scope defined by the present invention.

[0032] In this instruction manual, This refers to the portion that is connected to another substituent. It can be attached to any optional position of the attached group / fragment.

[0033] 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.

[0034] In this specification, when the position of a substituent or linker site on the ring is not fixed, it means that it can be linked to any of the optional sites on the ring. For example, Can represent Can represent Can represent And so on.

[0035] Examples of halogens described in this invention may include fluorine, chlorine, bromine, and iodine.

[0036] The alkyl group referred to in this invention refers to the general term for monovalent groups remaining after removing one hydrogen atom from an alkane molecule. It can be a straight-chain alkyl group or a branched-chain alkyl group, preferably having 1 to 20 carbon atoms, more preferably having 1 to 15 carbon atoms, more preferably having 1 to 12 carbon atoms, and particularly preferably having 1 to 6 carbon atoms. The straight-chain alkyl group includes methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl, etc., but is not limited thereto. The branched-chain alkyl group includes isopropyl, isobutyl, sec-butyl, tert-butyl, isomeric groups of n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, etc., but is not limited thereto. The alkyl groups mentioned above are preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, etc., but are not limited thereto.

[0037] The "substituted or unsubstituted silyl group" mentioned in this invention refers to -Si(R n )3 groups, wherein each R n Each R is independently selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic rings, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl rings. Preferably, each R n Each group is independently selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, and substituted or unsubstituted C3-C30 cycloalkyl. The alkyl group preferably has 1 to 20 carbon atoms, more preferably 1 to 15 carbon atoms, more preferably 1 to 10 carbon atoms, and particularly preferably 1 to 8 carbon atoms. The cycloalkyl group preferably has 3 to 20 carbon atoms, more preferably 3 to 15 carbon atoms, more preferably 3 to 10 carbon atoms, and particularly preferably 3 to 7 carbon atoms. Preferably, each R... nEach group is independently selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted heptyl, substituted or unsubstituted octyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl. Examples may include, but are not limited to, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, dimethylethylsilyl, dimethylisopropylsilyl, dimethyltert-butylsilyl, tricyclopentylsilyl, tricyclohexylsilyl, triphenylsilyl, triphenylsilyl, tripyridylsilyl, tripyridylsilyl, etc.

[0038] The cycloalkyl group described in this invention refers to the general term for a monovalent group remaining after removing one hydrogen atom from a cyclic alkane molecule. It can be a monocyclic cycloalkyl group, a polycyclic cycloalkyl group, or a bridged cycloalkyl group. Preferably, it has 3 to 20 carbon atoms, more preferably 3 to 18 carbon atoms, more preferably 3 to 12 carbon atoms, and particularly preferably 3 to 6 carbon atoms. The cycloalkyl group includes, but is not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, camphenyl, ferricyl, and isocamphenyl.

[0039] The aryl group referred to in this invention refers to the general term for a monovalent group remaining after removing a hydrogen atom from the aromatic carbon atom of an aromatic compound molecule. It can be a monocyclic aryl, polycyclic aryl, or fused-ring aryl. Preferably, it has 6 to 60 carbon atoms, more preferably 6 to 30 carbon atoms, more preferably 6 to 18 carbon atoms, and particularly preferably 6 to 12 carbon atoms. The monocyclic aryl group refers to an aryl group with only one aromatic ring in the molecule, such as phenyl, but not limited to this; the polycyclic aryl group refers to an aryl group with two or more independent aromatic rings in the molecule, and specific examples may include biphenyl, terphenyl, tetraphenyl, 1-phenylnaphthyl, 2-phenylnaphthyl, etc., but not limited to this; the fused-ring aryl group refers to an aryl group with two or more aromatic rings in the molecule that are fused together by sharing two adjacent carbon atoms, and specific examples may include naphthyl, anthraceneyl, phenanthryl, pyrene, peryl, fluorenyl, benzo[a]fluorenyl, triphenylene, fluoranyl, spirofluorenyl, spirodifluorenyl, etc., but not limited to this.

[0040] The heteroaryl group described in this invention refers to a group obtained by replacing one or more aromatic carbon atoms in an aryl group with heteroatoms. The heteroatoms include, but are not limited to, oxygen, sulfur, nitrogen, silicon, or phosphorus atoms, and preferably have 2 to 60 carbon atoms, more preferably 2 to 30 carbon atoms, more preferably 2 to 18 carbon atoms, and particularly preferably 2 to 12 carbon atoms. The linking site of the heteroaryl group can be located on a cyclic carbon atom or on a cyclic heteroatom. The heteroaryl group can be a monocyclic heteroaryl, polycyclic heteroaryl, or fused-ring heteroaryl. Specific examples of the monocyclic heteroaryl group may include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thiopheneyl, pyrroloyl, oxazolyl, thiazolyl, imidazolyl, etc., but are not limited thereto; specific examples of the polycyclic heteroaryl group may include bipyridyl, bipyrimidinyl, phenylpyridinyl, phenylpyrimidinyl, etc., but are not limited thereto; specific examples of the fused-ring heteroaryl group may include quinolinyl, isoquinolinyl, benzo[a]quinolinyl, benzo[a]isoquinolinyl, quinazolinyl, quinoxalinyl, benzo[a]quinazolinyl, benzo[a]quinazolinyl, benzo[a] Quinoxolinyl, o-phenantholinyl, naphridyl, indolyl, benzothiopheneyl, benzofuranyl, benzooxazolyl, benzoimidazoyl, benzothiazoyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothiopheneyl, benzodibenzothiopheneyl, dibenzooxazolyl, dibenzoimidazoyl, dibenzothiazoyl, carbazoleyl, benzocarbazoleyl, acridineyl, 9,10-dihydroacridyl, phenoxazinyl, phenthiazinyl, phenoxazinyl, spirofluorenexanthraceneyl, spirofluorenethixanthraceneyl, etc., but not limited to these.

[0041] The arylene group referred to in this invention refers to the collective term for the divalent group remaining after removing two hydrogen atoms from the aromatic carbon atom of an aromatic hydrocarbon molecule. It can be a monocyclic arylene, a polycyclic arylene, or a fused-ring arylene, preferably having 6 to 60 carbon atoms, more preferably 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 12 carbon atoms. The monocyclic arylene includes, but is not limited to, phenylene; the polycyclic arylene includes, but is not limited to, biphenylene, terphenylene; specific examples may include naphthylene, anthracene, phenanthrene, pyrene, terphenylene, fluoranthracene, etc., but are not limited to.

[0042] The term "heteroaryl" refers to a divalent group in which at least one carbon atom is replaced by a heteroatom. The heteroatom includes, but is not limited to, oxygen, sulfur, nitrogen, or phosphorus atoms. Preferably, it has 2 to 60 carbon atoms, more preferably 2 to 30 carbon atoms, more preferably 2 to 18 carbon atoms, and particularly preferably 2 to 12 carbon atoms. The linking site of the heteroaryl can be located on a cyclic carbon atom or a cyclic nitrogen atom. The heteroaryl can be a monocyclic, polycyclic, or fused-ring heteroaryl. Specific examples of the monocyclic and fused-ring heteroaryl groups may include, but are not limited to, pyridinyl, pyrimidinyl, triazineyl, furanyl, thiopheneyl, carbazolyl, benzofuranyl, benzothiopheneyl, benzocarbazolyl, dibenzofuranyl, dibenzothiopheneyl, and dibenzocarbazolyl; specific examples of the polycyclic heteroaryl groups may include, but are not limited to, bipyridinyl, bipyrimidinyl, and phenylpyridinyl.

[0043] The fused alicyclic and aromatic ring groups described in this invention refer to the general term for monovalent groups formed by fusion of an alicyclic and an aromatic ring and the removal of one hydrogen atom. Preferably, they have 6 to 60 carbon atoms, more preferably 6 to 30 carbon atoms, more preferably 6 to 18 carbon atoms, and particularly preferably 6 to 12 carbon atoms. The fused alicyclic and aromatic ring groups may include, but are not limited to, benzocyclopropane, benzocyclobutane, benzocyclobutenyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, benzocycloheptane, benzocycloheptenyl, etc.

[0044] The fused cyclic group of alicyclic and heteroaromatic rings described in this invention refers to the general term for the monovalent group obtained by removing one 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 particularly preferably 5 to 12 carbon atoms. The fused cycloyl groups of the alicyclic and heterocyclic rings may include, but are not limited to, pyridocyclopropyl, pyridocyclobutyl, pyridocyclopentyl, pyridocyclohexyl, pyridinium-benzocycloheptyl, pyrimidinium-cyclopropyl, pyrimidinium-cyclobutyl, pyrimidinium-cyclopentyl, pyrimidinium-benzohexyl, dibenzofuranocyclopropyl, dibenzofuranocyclobutyl, dibenzofuranocyclopentyl, dibenzofuranocyclohexyl, dibenzofuranocycloheptyl, dibenzothiophenecyclopropyl, dibenzothiophenecyclobutyl, dibenzothiophenecyclopentyl, dibenzothiophenecyclohexyl, dibenzothiophenecycloheptyl, carbazocyclopropyl, carbazocyclobutyl, carbazocyclopentyl, carbazocyclohexyl, carbazocycloheptyl, etc.

[0045] The fused alicyclic and aromatic ring cycloalgides described in this invention refer to the general term for divalent groups obtained by removing two hydrogen atoms after the alicyclic and aromatic rings are fused together. Preferably, they have 6 to 30 carbon atoms, more preferably 6 to 25 carbon atoms, even more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 12 carbon atoms. The fused alicyclic and aromatic ring cycloalgides may include, but are not limited to, benzo[a]cyclopropyl, benzo[a]cyclobutyl, benzo[a]cyclopentyl, benzo[a]cyclohexyl, benzo[a]cycloheptyl, benzo[a]cyclopentenyl, benzo[a]cyclohexenyl, benzo[a]cycloheptenyl, naphtho[a]cyclopropyl, naphtho[a]cyclobutyl, naphtho[a]cyclopentyl, and naphtho[a]cyclohexyl, etc.

[0046] The fused alicyclic and heteroaromatic ring groups described in this invention refer to the general term for the divalent groups obtained by removing two hydrogen atoms after the alicyclic and heteroaromatic rings are fused together. Preferably, they have 3 to 30 carbon atoms, more preferably 3 to 20 carbon atoms, more preferably 3 to 18 carbon atoms, and particularly preferably 3 to 12 carbon atoms. The fused alicyclic and heteroaromatic ring groups may include pyridinocyclopropyl, pyridinocyclobutyl, pyridinocyclopentyl, pyridinocyclohexyl, pyridinobenzocycloheptyl, pyrimidinoxopropyl, pyrimidinoxobutyl, pyrimidinoxopentyl, pyrimidinoxocyclohexyl, pyrimidinoxobenzocycloheptyl, and so on. Dibenzofuranocyclopropyl, dibenzofuranocyclobutyl, dibenzofuranocyclopentyl, dibenzofuranocyclohexyl, dibenzofuranocycloheptyl, dibenzothiophenocyclopropyl, dibenzothiophenocyclobutyl, dibenzothiophenocyclopentyl, dibenzothiophenocyclohexyl, dibenzothiophenocycloheptyl, carbazocyclopropyl, carbazocyclobutyl, carbazocyclopentyl, carbazocyclohexyl, carbazocycloheptyl, etc., but not limited to these.

[0047] The term "substituted..." as used in this invention, such as "substituted alkyl, substituted cycloalkyl, substituted aryl, substituted heteroaryl, substituted alicyclic and aromatic fused ring group, substituted arylene, substituted heteroaryl, alicyclic and aromatic fused ring group, alicyclic and heteroaromatic fused ring group", refers to an independent group that is monosubstituted or polysubstituted with the following groups: deuterium, cyano, nitro, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, etc., but not limited to these, or adjacent substituents may be linked to form a ring. Preferably, the following groups are monosubstituted or polysubstituted: deuterium, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cyclopentadienyl, cyclohexadienyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, perylene, pyrene, benzyl, 9,9-Dimethylfluorenyl, 9,9-Diphenylfluorenyl, 9-Methyl-9-phenylfluorenyl, 9,9'-spirodifluorenyl, diphenylamino, pyridyl, pyrimidinyl, triazinyl, carbazoleyl, acridineyl, furanyl, thiopheneyl, benzofuranyl, benzothiopheneyl, benzoxazolyl, benzoimidazolyl, benzothiazolyl, dibenzofuranyl, dibenzothiopheneyl, phenothiazinyl, phenothiazinyl, indolyl, etc., but not limited to these.

[0048] The cyclic structure formed by bonding as described in this invention refers to two groups being linked together by chemical bonds and optionally aromatized. Examples are shown below:

[0049]

[0050] In this invention, the rings formed by the connection can be three-membered rings, four-membered rings, five-membered rings, six-membered rings, seven-membered rings, eight-membered rings, fused rings, etc., such as cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, benzene, naphthalene, phenanthrene, triphenylene, pyridine, pyrimidine, quinoline, isoquinoline, quinazoline, quinoxaline, fluorene, dibenzofuran, dibenzothiophene, carbazole, etc., but are not limited to these.

[0051] This invention provides a nitrogen-containing fused aromatic ring compound having the structure shown in Formula I:

[0052]

[0053] Ar1 is selected from the group represented by formula II, wherein the ring A is selected from any one of substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C2-C60 heteroaryl;

[0054] X is selected from O, S, C(R)x )2 or N(R a );

[0055] Each of the Ts is independently selected from CH or N; the Ts fused with ring A are selected from C;

[0056] The R a It is selected from any one of substituted or unsubstituted silyl groups, substituted or unsubstituted C1-C30 alkyl groups, substituted or unsubstituted C3-C30 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic groups, and fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl groups;

[0057] The R x It is selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring;

[0058] R1 is independently selected from any one or a combination thereof, including hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl.

[0059] The R2 is independently selected from any one or a combination of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl ring.

[0060] The n1 is selected from 0, 1, or 2; the n2 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10;

[0061] Z1 to Z6 are each independently selected from C(R) y () or N, at least one of Z1 to Z6 is selected from N, and at most three of Z1 to Z6 are selected from N;

[0062] The R y It is selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring;

[0063] At least one of Ar2 and Ar3 is selected from the group shown in 1-a or 1-b, and the others are each independently selected from any one of the following: substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl ring;

[0064]

[0065] The Y is independently selected from O, S, C(R) c R d ) or N(R b );

[0066] The R c R d Each is independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring, or R c R d They connect with each other to form substituted or unsubstituted rings;

[0067] The R bIt is selected from any one of substituted or unsubstituted silyl groups, substituted or unsubstituted C1-C30 alkyl groups, substituted or unsubstituted C3-C30 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic groups, and fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl groups;

[0068] The R3 is independently selected from any one or combination of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl ring, or adjacent R3s are connected to each other to form a substituted or unsubstituted ring;

[0069] The n3 is selected from 0, 1, 2, 3, 4, 5, 6 or 7;

[0070] Each of L1 to L3 is independently selected from one or a combination of single bonds, substituted or unsubstituted C6 to C60 arylene groups, substituted or unsubstituted C2 to C60 heteroarylene groups, substituted or unsubstituted C3 to C30 alicyclic and C6 to C60 aromatic groups, substituted or unsubstituted C3 to C30 alicyclic and C2 to C60 heteroaromatic groups.

[0071] Preferably, the nitrogen-containing fused aromatic ring compound is selected from at least one of formulas I-1 to I-13:

[0072]

[0073]

[0074] More preferably, the nitrogen-containing fused aromatic ring compound is selected from at least one of formulas II-1 to II-14:

[0075]

[0076] Preferably, the group represented by Ar1 or Formula II is selected from any one of the following groups:

[0077]

[0078]

[0079] X is selected from O, S, C(R) x )2 or N(R a );

[0080] The T is selected from CH or N;

[0081] The R a It is selected from any one of substituted or unsubstituted silyl groups, substituted or unsubstituted C1-C30 alkyl groups, substituted or unsubstituted C3-C30 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic groups, and fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl groups;

[0082] The R x It is selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring;

[0083] R1 is independently selected from any one or a combination thereof, including hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl.

[0084] The R2 is independently selected from any one or a combination of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl ring.

[0085] The n1 is selected from 0, 1 or 2; the n4 is selected from 0, 1, 2, 3, 4, 5 or 6; the n5 is selected from 0, 1, 2, 3 or 4; and the n6 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.

[0086] More preferably, the group represented by Ar1 or Formula II is selected from any one of the following groups:

[0087]

[0088]

[0089] R1 is independently selected from any one or a combination thereof, including hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl.

[0090] The R2 is independently selected from any one or a combination thereof, including hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl.

[0091] The n1 is selected from 0, 1, or 2; the n3 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; the n4 is selected from 0, 1, 2, 3, 4, 5, or 6; the n5 is selected from 0, 1, 2, 3, or 4; the n6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the n7 is selected from 0, 1, 2, or 3; the n9 is selected from 0, 1, 2, 3, 4, or 5; the n 10 Choose from 0 or 1.

[0092] More preferably, the group represented by Ar1 or Formula II is selected from any one of the following groups:

[0093]

[0094]

[0095] R1 is independently selected from any one or a combination thereof, including hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl.

[0096] The R2 is independently selected from any one or a combination thereof, including hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl.

[0097] The n1 is selected from 0, 1, or 2; the n5 is selected from 0, 1, 2, 3, or 4; the n7 is selected from 0, 1, 2, or 3; the n 10 Selected from 0 or 1.

[0098] Preferably, R1 is independently selected from hydrogen, deuterium, cyano, nitro, halogen atom, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, dimethylethylsilyl, triphenylsilyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornel, phenyl, biphenyl, terphenyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, naphthalene Anthrayl, phenanthrene, triphenylene, pyridyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, naphthidyl, o-phenanthrolinel, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9,9'-spirodifluorenyl, benzo9,9-dimethylfluorenyl, benzo9,9'-spirodifluorenyl, furanyl, thiopheneyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzodibenzofuranyl, benzodibenzothiopheneyl, oxazolyl, thiazolyl, imidazolyl, benzooxazolyl, benzothiazolyl, benzoimidazolyl, deuterated methyl, deuterated ethyl, deuterated n-propyl, deuterated isopropyl, deuterated n-Butyl, deuterated isobutyl, deuterated sec-butyl, deuterated tert-butyl, deuterated adamantyl, deuterated norbornel, deuterated phenyl, deuterated biphenyl, deuterated terphenyl, deuterated naphthyl, deuterated anthracene, deuterated phenanthryl, deuterated triphenylene, deuterated pyridyl, deuterated pyrimidinyl, deuterated quinolinyl, deuterated isoquinolinyl, deuterated benzofuranyl, deuterated benzothiopheneyl, deuterated benzoxazolyl, deuterated benzothiazolyl, deuterated benzimidazolyl, fluorinated phenyl, fluorinated biphenyl, trifluoromethyl substituted phenyl, trifluoromethyl substituted biphenyl, trifluoromethyl substituted naphthyl, cyano-substituted phenyl, cyano-substituted biphenyl, cyano-substituted naphthyl, cyano-substituted... The following are listed: phenanthrene-substituted, cyano-substituted phenylene, cyano-substituted 9,9-dimethylfluorenyl, methyl-substituted adamantyl, methyl-substituted norbornel, methyl-substituted phenyl, methyl-substituted biphenyl, methyl-substituted naphthyl, ethyl-substituted phenyl, ethyl-substituted biphenyl, ethyl-substituted naphthyl, isopropyl-substituted phenyl, isopropyl-substituted biphenyl, isopropyl-substituted naphthyl, tert-butyl-substituted adamantyl, tert-butyl-substituted phenyl, tert-butyl-substituted biphenyl, tert-butyl-substituted naphthyl, tert-butyl-substituted phenanthrene, tert-butyl-substituted 9,9-dimethylfluorenyl, tert-butyl-substituted 9,9-diphenylfluorenyl, tert-butyl-substituted 9,9-diphenylfluorenyl, tert-butyl-substituted 9,9-diphenylfluorenyl, tert-butyl-substituted 9,9-dimethyl ...9'-Spirodifluorenyl, trimethylsilyl-substituted phenyl, triethylsilyl-substituted phenyl, triphenylsilyl-substituted phenyl, trimethylsilyl-substituted naphthyl, adamantyl-substituted phenyl, adamantyl-substituted biphenyl, norbornyl-substituted phenyl, norbornyl-substituted biphenyl, deuterated methyl-substituted phenyl, deuterated methyl-substituted biphenyl, deuterated isopropyl-substituted phenyl, deuterated isopropyl-substituted biphenyl, deuterated tert-butyl-substituted phenyl, deuterated tert-butyl-substituted biphenyl, naphthyl-substituted phenyl, phenanthryl-substituted phenyl, triphenylene-substituted phenyl, benzofuran-substituted phenyl, benzothiophene-substituted phenyl, pyridine-substituted phenyl, pyrimidine-substituted phenyl, quinoline-substituted phenyl, isoquinoline-substituted phenyl, quinazoline-substituted phenyl, quinoxaline-substituted phenyl, benzoxazole-substituted phenyl, benzothiazole-substituted phenyl, benzimidazole-substituted phenyl.

[0099] Preferably, R2 is independently selected from hydrogen, deuterium, cyano, nitro, halogen atom, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, dimethylethylsilyl, triphenylsilyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornel, phenyl, biphenyl, terphenyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, naphthalene Anthrayl, phenanthrene, triphenylene, pyridyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, naphthidyl, o-phenanthrolinel, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9,9'-spirodifluorenyl, benzo9,9-dimethylfluorenyl, benzo9,9'-spirodifluorenyl, furanyl, thiopheneyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzodibenzofuranyl, benzodibenzothiopheneyl, oxazolyl, thiazolyl, imidazolyl, benzooxazolyl, benzothiazolyl, benzoimidazolyl, deuterated methyl, deuterated ethyl, deuterated n-propyl, deuterated isopropyl, deuterated n-Butyl, deuterated isobutyl, deuterated sec-butyl, deuterated tert-butyl, deuterated adamantyl, deuterated norbornel, deuterated phenyl, deuterated biphenyl, deuterated terphenyl, deuterated naphthyl, deuterated anthracene, deuterated phenanthryl, deuterated triphenylene, deuterated pyridyl, deuterated pyrimidinyl, deuterated quinolinyl, deuterated isoquinolinyl, deuterated benzofuranyl, deuterated benzothiopheneyl, deuterated benzoxazolyl, deuterated benzothiazolyl, deuterated benzimidazolyl, fluorinated phenyl, fluorinated biphenyl, trifluoromethyl substituted phenyl, trifluoromethyl substituted biphenyl, trifluoromethyl substituted naphthyl, cyano-substituted phenyl, cyano-substituted biphenyl, cyano-substituted naphthyl, cyano-substituted... The following are listed: phenanthrene-substituted, cyano-substituted phenylene, cyano-substituted 9,9-dimethylfluorenyl, methyl-substituted adamantyl, methyl-substituted norbornel, methyl-substituted phenyl, methyl-substituted biphenyl, methyl-substituted naphthyl, ethyl-substituted phenyl, ethyl-substituted biphenyl, ethyl-substituted naphthyl, isopropyl-substituted phenyl, isopropyl-substituted biphenyl, isopropyl-substituted naphthyl, tert-butyl-substituted adamantyl, tert-butyl-substituted phenyl, tert-butyl-substituted biphenyl, tert-butyl-substituted naphthyl, tert-butyl-substituted phenanthrene, tert-butyl-substituted 9,9-dimethylfluorenyl, tert-butyl-substituted 9,9-diphenylfluorenyl, tert-butyl-substituted 9,9-diphenylfluorenyl, tert-butyl-substituted 9,9-diphenylfluorenyl, tert-butyl-substituted 9,9-dimethyl ...9'-Spirodifluorenyl, trimethylsilyl-substituted phenyl, triethylsilyl-substituted phenyl, triphenylsilyl-substituted phenyl, trimethylsilyl-substituted naphthyl, adamantyl-substituted phenyl, adamantyl-substituted biphenyl, norbornyl-substituted phenyl, norbornyl-substituted biphenyl, deuterated methyl-substituted phenyl, deuterated methyl-substituted biphenyl, deuterated isopropyl-substituted phenyl, deuterated isopropyl-substituted biphenyl, deuterated tert-butyl-substituted phenyl, deuterated tert-butyl-substituted biphenyl, naphthyl-substituted phenyl, phenanthryl-substituted phenyl, triphenylene-substituted phenyl, benzofuran-substituted phenyl, benzothiophene-substituted phenyl, pyridine-substituted phenyl, pyrimidine-substituted phenyl, quinoline-substituted phenyl, isoquinoline-substituted phenyl, quinazoline-substituted phenyl, quinoxaline-substituted phenyl, benzoxazole-substituted phenyl, benzothiazole-substituted phenyl, benzimidazole-substituted phenyl.

[0100] Preferably, at least one of Ar2 and Ar3 is selected from one of the groups derived from formulas 1-a and 1-b:

[0101]

[0102]

[0103] The R b It is selected from any one of substituted or unsubstituted silyl groups, substituted or unsubstituted C1-C30 alkyl groups, substituted or unsubstituted C3-C30 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic groups, and fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl groups;

[0104] The R c R d Each is independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring, or R c R d They connect with each other to form substituted or unsubstituted rings;

[0105] The R3 is independently selected from any one or combination of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl ring, or adjacent R3s are connected to each other to form a substituted or unsubstituted ring;

[0106] The n2 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; the n3 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; the n4 is selected from 0, 1, 2, 3, 4, 5, or 6; the n5 is selected from 0, 1, 2, 3, or 4; the n6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the n7 is selected from 0, 1, 2, or 3; the n8 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; the n9 is selected from 0, 1, 2, 3, 4, or 5; the n 11 Choose from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11.

[0107] Preferably, the R bSelected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, dimethylethylsilyl, triphenylsilyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornel, phenyl, biphenyl, terphenyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, naphthyl, anthracene, phenanthrene, phenylenetriene, pyridyl, pyrimidine alkyl, pyrazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, naphthidyl, o-phenanthrolinel, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9,9'-spirodifluorenyl, benzo9,9-dimethylfluorenyl, benzo9,9'-spirodifluorenyl, furanyl, thiopheneyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzodibenzofuranyl, benzodibenzothiopheneyl, oxazolyl, thiazolyl, imidazolyl, benzooxazolyl, benzothiazolyl, benzoimidazolyl, deuterated methyl, deuterated ethyl, deuterated n-propyl, deuterated isopropyl, deuterated n-butyl, deuterated isobutyl, deuterated sec-butyl, deuterated tert-butyl, deuterated adamantyl, deuterated norbornel, deuterated phenyl, deuterated biphenyl, deuterated terphenyl, deuterated naphthyl, deuterated anthracene, deuterated phenanthryl, deuterated triphenylene, deuterated pyridyl, deuterated pyrimidinyl, deuterated quinolinyl, deuterated isoquinolinyl, deuterated benzofuranyl, deuterated benzothiopheneyl, deuterated benzoxazolyl, deuterated benzothiazolyl, deuterated benzimidazolyl, fluorinated phenyl, fluorinated biphenyl, trifluoromethyl substituted phenyl, trifluoromethyl substituted biphenyl, trifluoromethyl substituted naphthyl, cyano-substituted phenyl, cyano-substituted biphenyl, cyano-substituted naphthyl, cyano-substituted phenanthryl, cyano alkyl-substituted triphenylene, cyano-substituted 9,9-dimethylfluorenyl, methyl-substituted adamantyl, methyl-substituted norbornel, methyl-substituted phenyl, methyl-substituted biphenyl, methyl-substituted naphthyl, ethyl-substituted phenyl, ethyl-substituted biphenyl, ethyl-substituted naphthyl, isopropyl-substituted phenyl, isopropyl-substituted biphenyl, isopropyl-substituted naphthyl, tert-butyl-substituted adamantyl, tert-butyl-substituted phenyl, tert-butyl-substituted biphenyl, tert-butyl-substituted naphthyl, tert-butyl-substituted phenanthrene, tert-butyl-substituted 9,9-dimethylfluorenyl, tert-butyl-substituted 9,9-diphenylfluorenyl, tert-butyl-substituted 9,9-diphenylfluorenyl9'-Spirodifluorenyl, trimethylsilyl-substituted phenyl, triethylsilyl-substituted phenyl, triphenylsilyl-substituted phenyl, trimethylsilyl-substituted naphthyl, adamantyl-substituted phenyl, adamantyl-substituted biphenyl, norbornyl-substituted phenyl, norbornyl-substituted biphenyl, deuterated methyl-substituted phenyl, deuterated methyl-substituted biphenyl, deuterated isopropyl-substituted phenyl, deuterated isopropyl-substituted biphenyl, deuterated tert-butyl-substituted phenyl, deuterated tert-butyl-substituted biphenyl, naphthyl-substituted phenyl, phenanthryl-substituted phenyl, triphenylene-substituted phenyl, benzofuran-substituted phenyl, benzothiophene-substituted phenyl, pyridine-substituted phenyl, pyrimidine-substituted phenyl, quinoline-substituted phenyl, isoquinoline-substituted phenyl, quinazoline-substituted phenyl, quinoxaline-substituted phenyl, benzoxazole-substituted phenyl, benzothiazole-substituted phenyl, benzimidazole-substituted phenyl.

[0108] Preferred, R c R dEach is independently selected from hydrogen, deuterium, cyano, nitro, halogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, dimethylethylsilyl, triphenylsilyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, naphthyl, anthracene, phenanthrene alkyl, triphenylene, pyridinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, naphthidyl, o-phenanthrolinel, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9,9'-spirodifluorenyl, benzo9,9-dimethylfluorenyl, benzo9,9'-spirodifluorenyl, furanyl, thiopheneyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzodibenzofuranyl, benzodibenzothiopheneyl, oxazolyl, thiazolyl, imidazolyl, benzooxazolyl, benzothiazolyl, benzoimidazolyl, deuterated methyl, deuterated ethyl, deuterated n-propyl, deuterated isopropyl, deuterated n-butyl Deuterated isobutyl, deuterated sec-butyl, deuterated tert-butyl, deuterated adamantyl, deuterated norbornel, deuterated phenyl, deuterated biphenyl, deuterated terphenyl, deuterated naphthyl, deuterated anthracene, deuterated phenanthrene, deuterated triphenylene, deuterated pyridyl, deuterated pyrimidinyl, deuterated quinolinyl, deuterated isoquinolinyl, deuterated benzofuranyl, deuterated benzothiopheneyl, deuterated benzoxazolyl, deuterated benzothiazolyl, deuterated benzimidazolyl, fluorinated phenyl, fluorinated biphenyl, trifluoromethyl substituted phenyl, trifluoromethyl substituted biphenyl, trifluoromethyl substituted naphthyl, cyano-substituted phenyl, cyano-substituted biphenyl, cyano-substituted naphthyl, cyano-substituted Phenylenyl, cyano-substituted phenylene, cyano-substituted 9,9-dimethylfluorenyl, methyl-substituted adamantyl, methyl-substituted norbornel, methyl-substituted phenyl, methyl-substituted biphenyl, methyl-substituted naphthyl, ethyl-substituted phenyl, ethyl-substituted biphenyl, ethyl-substituted naphthyl, isopropyl-substituted phenyl, isopropyl-substituted biphenyl, isopropyl-substituted naphthyl, tert-butyl-substituted adamantyl, tert-butyl-substituted phenyl, tert-butyl-substituted biphenyl, tert-butyl-substituted naphthyl, tert-butyl-substituted phenylenyl, tert-butyl-substituted 9,9-dimethylfluorenyl, tert-butyl-substituted 9,9-diphenylfluorenyl, tert-butyl-substituted 9,9-diphenylfluorenyl9'-Spirodifluorenyl, trimethylsilyl-substituted phenyl, triethylsilyl-substituted phenyl, triphenylsilyl-substituted phenyl, trimethylsilyl-substituted naphthyl, adamantyl-substituted phenyl, adamantyl-substituted biphenyl, norbornyl-substituted phenyl, norbornyl-substituted biphenyl, deuterated methyl-substituted phenyl, deuterated methyl-substituted biphenyl, deuterated isopropyl-substituted phenyl, deuterated isopropyl-substituted biphenyl, deuterated tert-butyl-substituted phenyl, deuterated tert-butyl-substituted biphenyl, naphthyl-substituted phenyl, phenanthryl-substituted phenyl, triphenylene-substituted phenyl, benzofuran-substituted phenyl, benzothiophene-substituted phenyl, pyridine-substituted phenyl, pyrimidine-substituted phenyl, quinoline-substituted phenyl, isoquinoline-substituted phenyl, quinazoline-substituted phenyl, quinoxaline-substituted phenyl, benzoxazole-substituted phenyl, benzothiazole-substituted phenyl, benzimidazole-substituted phenyl.

[0109] Preferably, R3 is independently selected from hydrogen, deuterium, cyano, nitro, halogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, dimethylethylsilyl, triphenylsilyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornel, phenyl, biphenyl, terphenyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, naphthyl Anthrayl, phenanthrene, triphenylene, pyridyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, naphthidyl, o-phenanthrolinel, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9,9'-spirodifluorenyl, benzo9,9-dimethylfluorenyl, benzo9,9'-spirodifluorenyl, furanyl, thiopheneyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzodibenzofuranyl, benzodibenzothiopheneyl, oxazolyl, thiazolyl, imidazolyl, benzooxazolyl, benzothiazolyl, benzoimidazolyl, deuterated methyl, deuterated ethyl, deuterated n-propyl, deuterated isopropyl, deuterated n-Butyl, deuterated isobutyl, deuterated sec-butyl, deuterated tert-butyl, deuterated adamantyl, deuterated norbornel, deuterated phenyl, deuterated biphenyl, deuterated terphenyl, deuterated naphthyl, deuterated anthracene, deuterated phenanthryl, deuterated triphenylene, deuterated pyridyl, deuterated pyrimidinyl, deuterated quinolinyl, deuterated isoquinolinyl, deuterated benzofuranyl, deuterated benzothiopheneyl, deuterated benzoxazolyl, deuterated benzothiazolyl, deuterated benzimidazolyl, fluorinated phenyl, fluorinated biphenyl, trifluoromethyl substituted phenyl, trifluoromethyl substituted biphenyl, trifluoromethyl substituted naphthyl, cyano-substituted phenyl, cyano-substituted biphenyl, cyano-substituted naphthyl, cyano-substituted... The following are listed: phenanthrene-substituted, cyano-substituted phenylene, cyano-substituted 9,9-dimethylfluorenyl, methyl-substituted adamantyl, methyl-substituted norbornel, methyl-substituted phenyl, methyl-substituted biphenyl, methyl-substituted naphthyl, ethyl-substituted phenyl, ethyl-substituted biphenyl, ethyl-substituted naphthyl, isopropyl-substituted phenyl, isopropyl-substituted biphenyl, isopropyl-substituted naphthyl, tert-butyl-substituted adamantyl, tert-butyl-substituted phenyl, tert-butyl-substituted biphenyl, tert-butyl-substituted naphthyl, tert-butyl-substituted phenanthrene, tert-butyl-substituted 9,9-dimethylfluorenyl, tert-butyl-substituted 9,9-diphenylfluorenyl, tert-butyl-substituted 9,9-diphenylfluorenyl, tert-butyl-substituted 9,9-diphenylfluorenyl, tert-butyl-substituted 9,9-dimethyl ...9'-Spirodifluorenyl, trimethylsilyl-substituted phenyl, triethylsilyl-substituted phenyl, triphenylsilyl-substituted phenyl, trimethylsilyl-substituted naphthyl, adamantyl-substituted phenyl, adamantyl-substituted biphenyl, norbornyl-substituted phenyl, norbornyl-substituted biphenyl, deuterated methyl-substituted phenyl, deuterated methyl-substituted biphenyl, deuterated isopropyl-substituted phenyl, deuterated isopropyl-substituted biphenyl, deuterated tert-butyl-substituted phenyl, deuterated tert-butyl-substituted biphenyl, naphthyl-substituted phenyl, phenanthryl-substituted phenyl, triphenylene-substituted phenyl, benzofuran-substituted phenyl, benzothiophene-substituted phenyl, pyridine-substituted phenyl, pyrimidine-substituted phenyl, quinoline-substituted phenyl, isoquinoline-substituted phenyl, quinazoline-substituted phenyl, quinoxaline-substituted phenyl, benzoxazole-substituted phenyl, benzothiazole-substituted phenyl, benzimidazole-substituted phenyl.

[0110] Preferably, when Ar2 and Ar3 are not of formulas 1-a and 1-b, they are selected from one or a combination of the following groups:

[0111]

[0112] Wherein, each of the r is independently selected from CH or N;

[0113] Each of M1 to M4 is independently selected from O, S, and C(R). j R k ), N(R z ), Si(R) m Any one of 2;

[0114] The R j R k Each is independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring, or R j R k The links between them form substituted or unsubstituted rings;

[0115] The R zIt is selected from any one of the following: substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring;

[0116] The R m It is selected from any one of hydrogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring;

[0117] The R h Each is independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring;

[0118] The R4 is independently selected from any one or combination of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl ring, or adjacent R4s connected to each other to form a substituted or unsubstituted ring;

[0119] The R5 is independently selected from any one or combination of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl ring, or adjacent R5s are connected to each other to form a substituted or unsubstituted ring;

[0120] The n1 is selected from 0, 1, or 2; the n3 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; the n5 is selected from 0, 1, 2, 3, or 4; the n7 is selected from 0, 1, 2, or 3; the n8 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; and the n9 is selected from 0, 1, 2, 3, 4, or 5.

[0121] More preferably, when Ar2 and Ar3 are not of formulas 1-a and 1-b, they are selected from one or a combination of the following groups:

[0122]

[0123]

[0124] The R f R g Each is independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl ring;

[0125] The R h Each is independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl ring;

[0126] The R i It is selected from any one of the following: substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring;

[0127] The R4 is independently selected from any one or combination of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl ring, or adjacent R4s are connected to each other to form a substituted or unsubstituted ring;

[0128] The R5 is independently selected from any one or combination of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl ring, or adjacent R5s are connected to each other to form a substituted or unsubstituted ring;

[0129] The k1 is selected from 0, 1, 2, 3, 4, or 5; the k2 is selected from 0, 1, 2, 3, or 4; the k3 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; the k4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; the k5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; the k6 is selected from 0, 1, or 2; the k7 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the k8 is selected from 0, 1, 2, or 3; the k9 is selected from 0, 1, 2, 3, 4, 5, or 6; the k 10 Choose from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.

[0130] Preferably, R4 is independently selected from hydrogen, deuterium, cyano, nitro, halogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, dimethylethylsilyl, triphenylsilyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornel, phenyl, biphenyl, terphenyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, naphthyl Anthrayl, phenanthrene, triphenylene, pyridyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, naphthidyl, o-phenanthrolinel, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9,9'-spirodifluorenyl, benzo9,9-dimethylfluorenyl, benzo9,9'-spirodifluorenyl, furanyl, thiopheneyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzodibenzofuranyl, benzodibenzothiopheneyl, oxazolyl, thiazolyl, imidazolyl, benzooxazolyl, benzothiazolyl, benzoimidazolyl, deuterated methyl, deuterated ethyl, deuterated n-propyl, deuterated isopropyl, deuterated n-Butyl, deuterated isobutyl, deuterated sec-butyl, deuterated tert-butyl, deuterated adamantyl, deuterated norbornel, deuterated phenyl, deuterated biphenyl, deuterated terphenyl, deuterated naphthyl, deuterated anthracene, deuterated phenanthryl, deuterated triphenylene, deuterated pyridyl, deuterated pyrimidinyl, deuterated quinolinyl, deuterated isoquinolinyl, deuterated benzofuranyl, deuterated benzothiopheneyl, deuterated benzoxazolyl, deuterated benzothiazolyl, deuterated benzimidazolyl, fluorinated phenyl, fluorinated biphenyl, trifluoromethyl substituted phenyl, trifluoromethyl substituted biphenyl, trifluoromethyl substituted naphthyl, cyano-substituted phenyl, cyano-substituted biphenyl, cyano-substituted naphthyl, cyano-substituted... The following are listed: phenanthrene-substituted, cyano-substituted phenylene, cyano-substituted 9,9-dimethylfluorenyl, methyl-substituted adamantyl, methyl-substituted norbornel, methyl-substituted phenyl, methyl-substituted biphenyl, methyl-substituted naphthyl, ethyl-substituted phenyl, ethyl-substituted biphenyl, ethyl-substituted naphthyl, isopropyl-substituted phenyl, isopropyl-substituted biphenyl, isopropyl-substituted naphthyl, tert-butyl-substituted adamantyl, tert-butyl-substituted phenyl, tert-butyl-substituted biphenyl, tert-butyl-substituted naphthyl, tert-butyl-substituted phenanthrene, tert-butyl-substituted 9,9-dimethylfluorenyl, tert-butyl-substituted 9,9-diphenylfluorenyl, tert-butyl-substituted 9,9-diphenylfluorenyl, tert-butyl-substituted 9,9-diphenylfluorenyl, tert-butyl-substituted 9,9-dimethyl ...9'-Spirodifluorenyl, trimethylsilyl-substituted phenyl, triethylsilyl-substituted phenyl, triphenylsilyl-substituted phenyl, trimethylsilyl-substituted naphthyl, adamantyl-substituted phenyl, adamantyl-substituted biphenyl, norbornyl-substituted phenyl, norbornyl-substituted biphenyl, deuterated methyl-substituted phenyl, deuterated methyl-substituted biphenyl, deuterated isopropyl-substituted phenyl, deuterated isopropyl-substituted biphenyl, deuterated tert-butyl-substituted phenyl, deuterated tert-butyl-substituted biphenyl, naphthyl-substituted phenyl, phenanthryl-substituted phenyl, triphenylene-substituted phenyl, benzofuran-substituted phenyl, benzothiophene-substituted phenyl, pyridine-substituted phenyl, pyrimidine-substituted phenyl, quinoline-substituted phenyl, isoquinoline-substituted phenyl, quinazoline-substituted phenyl, quinoxaline-substituted phenyl, benzoxazole-substituted phenyl, benzothiazole-substituted phenyl, benzimidazole-substituted phenyl.

[0131] Preferably, R5 is independently selected from hydrogen, deuterium, cyano, nitro, halogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, dimethylethylsilyl, triphenylsilyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornel, phenyl, biphenyl, terphenyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, naphthyl Anthrayl, phenanthrene, triphenylene, pyridyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, naphthidyl, o-phenanthrolinel, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9,9'-spirodifluorenyl, benzo9,9-dimethylfluorenyl, benzo9,9'-spirodifluorenyl, furanyl, thiopheneyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzodibenzofuranyl, benzodibenzothiopheneyl, oxazolyl, thiazolyl, imidazolyl, benzooxazolyl, benzothiazolyl, benzoimidazolyl, deuterated methyl, deuterated ethyl, deuterated n-propyl, deuterated isopropyl, deuterated n-Butyl, deuterated isobutyl, deuterated sec-butyl, deuterated tert-butyl, deuterated adamantyl, deuterated norbornel, deuterated phenyl, deuterated biphenyl, deuterated terphenyl, deuterated naphthyl, deuterated anthracene, deuterated phenanthryl, deuterated triphenylene, deuterated pyridyl, deuterated pyrimidinyl, deuterated quinolinyl, deuterated isoquinolinyl, deuterated benzofuranyl, deuterated benzothiopheneyl, deuterated benzoxazolyl, deuterated benzothiazolyl, deuterated benzimidazolyl, fluorinated phenyl, fluorinated biphenyl, trifluoromethyl substituted phenyl, trifluoromethyl substituted biphenyl, trifluoromethyl substituted naphthyl, cyano-substituted phenyl, cyano-substituted biphenyl, cyano-substituted naphthyl, cyano-substituted... The following are listed: phenanthrene-substituted, cyano-substituted phenylene, cyano-substituted 9,9-dimethylfluorenyl, methyl-substituted adamantyl, methyl-substituted norbornel, methyl-substituted phenyl, methyl-substituted biphenyl, methyl-substituted naphthyl, ethyl-substituted phenyl, ethyl-substituted biphenyl, ethyl-substituted naphthyl, isopropyl-substituted phenyl, isopropyl-substituted biphenyl, isopropyl-substituted naphthyl, tert-butyl-substituted adamantyl, tert-butyl-substituted phenyl, tert-butyl-substituted biphenyl, tert-butyl-substituted naphthyl, tert-butyl-substituted phenanthrene, tert-butyl-substituted 9,9-dimethylfluorenyl, tert-butyl-substituted 9,9-diphenylfluorenyl, tert-butyl-substituted 9,9-diphenylfluorenyl, tert-butyl-substituted 9,9-diphenylfluorenyl, tert-butyl-substituted 9,9-dimethyl ...9'-Spirodifluorenyl, trimethylsilyl-substituted phenyl, triethylsilyl-substituted phenyl, triphenylsilyl-substituted phenyl, trimethylsilyl-substituted naphthyl, adamantyl-substituted phenyl, adamantyl-substituted biphenyl, norbornyl-substituted phenyl, norbornyl-substituted biphenyl, deuterated methyl-substituted phenyl, deuterated methyl-substituted biphenyl, deuterated isopropyl-substituted phenyl, deuterated isopropyl-substituted biphenyl, deuterated tert-butyl-substituted phenyl, deuterated tert-butyl-substituted biphenyl, naphthyl-substituted phenyl, phenanthryl-substituted phenyl, triphenylene-substituted phenyl, benzofuran-substituted phenyl, benzothiophene-substituted phenyl, pyridine-substituted phenyl, pyrimidine-substituted phenyl, quinoline-substituted phenyl, isoquinoline-substituted phenyl, quinazoline-substituted phenyl, quinoxaline-substituted phenyl, benzoxazole-substituted phenyl, benzothiazole-substituted phenyl, benzimidazole-substituted phenyl.

[0132] Preferably, each of L1 to L3 is independently selected from a single bond or a combination thereof from the following groups:

[0133]

[0134] Wherein, each of the p is independently selected from CH or N;

[0135] Each of M5 to M7 is independently selected from O, S, and C(R). p R q ), N(R r Any one of the following;

[0136] The R p R q Each is independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloyl group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, fused cycloyl group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl rings, or R p R q The links between them form substituted or unsubstituted rings;

[0137] The R rIt is selected from any one of the following: substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring;

[0138] The R n Each is independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring;

[0139] The R6 is independently selected from any one or a combination of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl ring.

[0140] The b0 is selected from 0, 1, or 2; the b1 is selected from 0, 1, 2, 3, or 4; the b2 is selected from 0, 1, 2, 3, 4, 5, or 6; and the b3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8.

[0141] More preferably, each of L1 to L3 is independently selected from a single bond or a combination thereof from the following groups:

[0142]

[0143]

[0144] The R s Each is independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring;

[0145] The R t Any one of the following: substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring fused cycloalcohol, or substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl ring fused cycloalcohol;

[0146] The R v Each is independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring;

[0147] The R7 is independently selected from any one or a combination thereof, including hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl.

[0148] The c0 is selected from 0, 1, or 2; the c1 is selected from 0, 1, 2, 3, or 4; the c2 is selected from 0, 1, 2, 3, 4, 5, or 6; the c3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the c4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; the c5 is selected from 0, 1, 2, or 3; the c6 is selected from 0 or 1; the c7 is selected from 0, 1, 2, 3, 4, or 5; and the c8 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9.

[0149] Preferably, R7 is independently selected from hydrogen, deuterium, cyano, nitro, halogen atom, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, dimethylethylsilyl, triphenylsilyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornel, phenyl, biphenyl, terphenyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, naphthalene Anthrayl, phenanthrene, triphenylene, pyridyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, naphthidyl, o-phenanthrolinel, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9,9'-spirodifluorenyl, benzo9,9-dimethylfluorenyl, benzo9,9'-spirodifluorenyl, furanyl, thiopheneyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzodibenzofuranyl, benzodibenzothiopheneyl, oxazolyl, thiazolyl, imidazolyl, benzooxazolyl, benzothiazolyl, benzoimidazolyl, deuterated methyl, deuterated ethyl, deuterated n-propyl, deuterated isopropyl, deuterated n-Butyl, deuterated isobutyl, deuterated sec-butyl, deuterated tert-butyl, deuterated adamantyl, deuterated norbornel, deuterated phenyl, deuterated biphenyl, deuterated terphenyl, deuterated naphthyl, deuterated anthracene, deuterated phenanthryl, deuterated triphenylene, deuterated pyridyl, deuterated pyrimidinyl, deuterated quinolinyl, deuterated isoquinolinyl, deuterated benzofuranyl, deuterated benzothiopheneyl, deuterated benzoxazolyl, deuterated benzothiazolyl, deuterated benzimidazolyl, fluorinated phenyl, fluorinated biphenyl, trifluoromethyl substituted phenyl, trifluoromethyl substituted biphenyl, trifluoromethyl substituted naphthyl, cyano-substituted phenyl, cyano-substituted biphenyl, cyano-substituted naphthyl, cyano-substituted... The following are listed: phenanthrene-substituted, cyano-substituted phenylene, cyano-substituted 9,9-dimethylfluorenyl, methyl-substituted adamantyl, methyl-substituted norbornel, methyl-substituted phenyl, methyl-substituted biphenyl, methyl-substituted naphthyl, ethyl-substituted phenyl, ethyl-substituted biphenyl, ethyl-substituted naphthyl, isopropyl-substituted phenyl, isopropyl-substituted biphenyl, isopropyl-substituted naphthyl, tert-butyl-substituted adamantyl, tert-butyl-substituted phenyl, tert-butyl-substituted biphenyl, tert-butyl-substituted naphthyl, tert-butyl-substituted phenanthrene, tert-butyl-substituted 9,9-dimethylfluorenyl, tert-butyl-substituted 9,9-diphenylfluorenyl, tert-butyl-substituted 9,9-diphenylfluorenyl, tert-butyl-substituted 9,9-diphenylfluorenyl, tert-butyl-substituted 9,9-dimethyl ...9'-Spirodifluorenyl, trimethylsilyl-substituted phenyl, triethylsilyl-substituted phenyl, triphenylsilyl-substituted phenyl, trimethylsilyl-substituted naphthyl, adamantyl-substituted phenyl, adamantyl-substituted biphenyl, norbornyl-substituted phenyl, norbornyl-substituted biphenyl, deuterated methyl-substituted phenyl, deuterated methyl-substituted biphenyl, deuterated isopropyl-substituted phenyl, deuterated isopropyl-substituted biphenyl, deuterated tert-butyl-substituted phenyl, deuterated tert-butyl-substituted biphenyl, naphthyl-substituted phenyl, phenanthryl-substituted phenyl, triphenylene-substituted phenyl, benzofuran-substituted phenyl, benzothiophene-substituted phenyl, pyridine-substituted phenyl, pyrimidine-substituted phenyl, quinoline-substituted phenyl, isoquinoline-substituted phenyl, quinazoline-substituted phenyl, quinoxaline-substituted phenyl, benzoxazole-substituted phenyl, benzothiazole-substituted phenyl, benzimidazole-substituted phenyl.

[0150] Most preferably, the nitrogen-containing fused aromatic ring compound is selected from at least one of the following structures:

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173] The above lists some specific structural forms of nitrogen-containing fused aromatic ring 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.

[0174] The present invention also provides an organic electroluminescent device comprising at least one of the nitrogen-containing fused aromatic ring compounds described in the present invention.

[0175] Preferably, the organic electroluminescent device includes an anode, a cathode, and an organic layer, wherein the organic layer is located between the anode and the cathode or outside one or more electrodes of the anode and the cathode, and the organic layer contains at least one of the nitrogen-containing fused aromatic compounds described in this invention.

[0176] Preferably, the organic electroluminescent device of the present invention may comprise one or more organic layers. These organic layers may include a light-emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, a hole blocking layer, an electron blocking layer, and a capping layer. Specifically, the organic layer located between the anode and cathode may include a light-emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron blocking layer. The organic layer located outside one or more electrodes of the anode and cathode may include a capping layer. The organic layers may be formed as a single layer or as a multilayer structure with multiple organic layers stacked on top of each other. Furthermore, each organic layer may also include one or more layers; for example, the hole transport layer may include a first hole transport layer and a second hole transport layer. However, the structure of the organic electroluminescent device is not limited to this and may include fewer or more organic layers.

[0177] More preferably, the organic layer comprises at least one of an electron transport layer or a hole blocking layer, wherein the at least one of the electron transport layer or hole blocking layer comprises at least one of the nitrogen-containing fused aromatic ring compounds described in this invention.

[0178] More preferably, the organic layer is located between the anode and the cathode, and the organic layer includes an electron transport layer, which includes at least one of the nitrogen-containing fused aromatic compounds described in this invention.

[0179] More preferably, the organic layer is located between the anode and the cathode, and the organic layer includes a hole-blocking layer, which includes at least one of the nitrogen-containing fused aromatic compounds of the present invention.

[0180] Most preferably, the organic layer is located between the anode and the cathode, and the organic layer includes a light-emitting layer, which includes at least one of the nitrogen-containing fused aromatic compounds of the present invention.

[0181] As the anode of the present invention, a material with a high work function is preferred. The anode can be a transmission electrode, a reflection electrode, or a semi-transmission electrode. When the anode is a transmission electrode, the material used to form the anode can be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or any combination thereof; when the anode is a semi-transmission electrode or a reflection electrode, the material used to form the anode can be selected from magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof. The anode can have a single-layer structure or a multilayer structure including two or more layers. For example, the anode can have a single-layer structure of Al or a three-layer structure of ITO / Ag / ITO, but the structure of the anode is not limited to these.

[0182] As the hole injection layer of the present invention, a material with good hole-accepting ability is preferred. Specific examples include metalloporphyrins, oligothiophenes, arylamines, hexanitrile hexaazabenzanphenanthrene, quinacridones, perylene oxides, etc. Examples include 4,4',4”-tris[2-naphthylphenylamino]triphenylamine (2-TNATA), 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazabenzanphenanthrene (HATCN), copper phthalocyanine (CuPC), 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanodimethyl-p-benzoquinone (F4-TCNQ), poly(3,4-ethylenedioxythiophene)-poly(styrenesulfonic acid) (PEDOT / PSS), etc., but are not limited to these. It can be a single structure composed of a single substance, or a single-layer or multi-layer structure formed by different substances.

[0183] As the hole transport layer of the present invention, a material with high hole mobility is preferred. Specific examples may include materials such as diphenylamine compounds, fluorene compounds, carbazole compounds, and benzidine compounds. Examples include 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), 4,4'4"-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4'-cyclohexylbis[N,N-di(4-methylphenyl)aniline] (TAPC), and 4,4',4"-tris(carbazole-9-yl)triphenylamine (TCTA), but are not limited thereto.

[0184] As the luminescent layer material described in this invention, in addition to the nitrogen-containing fused aromatic ring compound described in this invention, red, green or blue luminescent materials can be used. They typically contain a guest (doped) material and a host material. The guest material can be a simple fluorescent material or a phosphorescent material, or a combination of fluorescent and phosphorescent materials. The host material of the luminescent layer not only needs to possess bipolar charge transport properties, but also needs appropriate energy levels to effectively transfer excitation energy to the guest luminescent material. Examples of such materials include stilbene aryl derivatives, stilbene derivatives, carbazole derivatives, triarylamine derivatives, anthracene derivatives, and pyrene derivatives. Examples include 9,9'-diphenyl-9H,9'H-3,3'-bicarbazole, 9-(5-(3-(9H-carbazole-9-yl)phenyl)pyridin-3-yl)-9H-carbazole (CPPyC), 5,7-diphenyl-5,7-dihydroindolo[2,3-b]carbazole, 4,4'-bis(carbazole-9-yl)-2,2'-dimethylbiphenyl (CDBP), 9,10-bis(2-naphthyl)anthracene (ADN), and 2-tert-butyl-9,10-bis(2-naphthyl)anthracene (TBADN), but are not limited to these.

[0185] The guest material can be selected from any one or more of the following structures: metal complexes (e.g., iridium complexes, platinum complexes, osmium complexes, rhodium complexes, etc.), anthracene derivatives, pyrene derivatives, perylene derivatives, etc. Examples include bis(2-(naphthyl-2-yl)pyridine)(acetylacetone)iridium (Ir(npy)2acac), bis(2-phenylpyridine)iridium acetylacetone (Ir(ppy)2(acac)), tris[2-(3-methyl-2-pyridyl)phenyl]iridium (Ir(3mppy)3), bis... (2-Benzo[H]quinoline-C2,N')(acetylacetone)iridium (Ir(bzq)2(acac)), bis(1-phenyl-isoquinoline)(acetylacetone)iridium (Ir(piq)2(acac)), tris(2-phenylpyridine)iridium (Ir(ppy3)), 4,4'-bis(9-ethyl-3-carbazolevinyl)-1,1'-biphenyl (BCzVBi), 4,4'-bis[4-(di-p-tolylamino)styryl]biphenyl (DPAVBi), etc., but not limited to these.

[0186] As the electron transport layer material of the present invention, in addition to the nitrogen-containing fused aromatic ring compound described in the present invention, materials with high electron mobility are preferred, and can be selected from any one or more of the following structures: metal chelates, oxazole derivatives, thiazole derivatives, diazole derivatives, azabenzene derivatives, diazanthracene derivatives, silicon-containing heterocyclic compounds, boron-containing heterocyclic compounds, cyano compounds, quinoline derivatives, phenanthroline derivatives, benzimidazole derivatives, etc., but are not limited thereto. It can be a single structure composed of a single substance, or a single-layer structure or a multi-layer structure formed by different substances.

[0187] As the hole-blocking layer material of the present invention, in addition to the nitrogen-containing fused aromatic ring compound described in the present invention, a material that can effectively block holes is preferred, and can be selected from any one or more of the following structures: phenanthroline derivatives, rare earth derivatives, oxazole derivatives, triazole derivatives, triazine derivatives, etc., but not limited thereto.

[0188] As the electron injection layer material of the present invention, a material with a low work function is preferred, and can be selected from any one or more of the following structures: metals, alkali metals, alkaline earth metals, alkali metal halides, alkaline earth metal halides, alkali metal oxides, alkaline earth metal oxides, alkali metal salts, alkaline earth metal salts, metal complexes, and other substances with high electron injection properties. Examples include Li, Ca, Sr, LiF, CsF, CaF2, BaO, Li2CO3, CaCO3, Li2C2O4, Cs2C2O4, CsAlF4, LiOx, Yb, Tb, cesium 8-hydroxyquinoline, tris(8-hydroxyquinoline)aluminum, etc., but are not limited thereto.

[0189] As the cathode of the present invention, a material with a low work function is preferred, and the cathode can be selected from a transmission electrode, a semi-reflective electrode, or a reflective electrode. When the cathode is a transmission electrode, the material used to form the cathode can be selected from transparent metal oxides (e.g., ITO, IZO, etc.); when the cathode is a semi-reflective electrode or a reflective electrode, the material used to form the cathode can be selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, compounds including them, or mixtures thereof (e.g., mixtures of Ag and Mg), but is not limited thereto.

[0190] As the capping layer material of the present invention, a material having a photocoupler effect is preferred. Specific examples may include: metal halides, metal oxides, metal nitrides, aromatic amine derivatives, carbazole derivatives, oxazole derivatives, etc. Examples include LiF, CsF, MgF2, CaF2, CsCl, CuI, V2O5, WO3, MoO3, TiO2, ZrO, ZnO, SiO2, SiN, Alq3, but are not limited thereto.

[0191] The aforementioned organic layers, cathode, anode, and capping layer can be prepared using any one of the following methods: vacuum evaporation, inkjet printing, sputtering, plasma coating, spin coating, dip coating, or screen printing. There are no particular limitations on the thickness of each layer, as long as good device performance is achieved. The aforementioned organic layers are preferably prepared using vacuum evaporation, inkjet printing, or spin coating, but are not limited to these methods.

[0192] The organic electroluminescent device provided by this invention can be applied to lighting and display fields, specifically including lighting sources, smartphone displays, tablet displays, flat-panel displays, VR, smartwatches, wearable devices, and automotive systems.

[0193] Preparation and characterization of compounds

[0194] Description of raw materials, reagents, and characterization equipment:

[0195] 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.

[0196] Mass spectrometry was performed using a Waters G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer, with chloroform as the solvent.

[0197] Elemental analysis was performed using a Vario EL cube organic elemental analyzer from Elementar GmbH, Germany, with sample masses ranging from 5 to 10 mg.

[0198] 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, using conventional methods well known to those skilled in the art. The main reaction types involved in this invention are the Suzuki coupling reaction and the Miyaura borate esterification reaction.

[0199] Synthetic route

[0200] Preparation of compound I:

[0201]

[0202] The X a ~X c Each is independently selected from any one of I, Br, and Cl; the limitations of Z1 to Z6, Ar1 to Ar3, and L1 to L3 are the same as those mentioned above.

[0203] Synthesis Example 1: Preparation of Intermediate A-4

[0204]

[0205] Add a-4 (53.26 g, 195.00 mmol), b-4 (36.88 g, 200.00 mmol), sodium carbonate (31.80 g, 300.00 mmol), and 780 mL of toluene / ethanol / water (volume ratio 2:1:1) to a reaction flask. After purging the air three times with nitrogen, add tetrakis(triphenylphosphine)palladium (2.31 g, 2.00 mmol). Stir the reaction mixture under nitrogen protection for 5.5 hours. After the reaction is complete, cool the reaction mixture to room temperature, filter, wash with distilled water, and then recrystallize the obtained solid from toluene to give intermediate c-4 (53.86 g, yield 83%). HPLC analysis showed that the purity of the solid was ≥99.69%.

[0206] C-4 (49.92 g, 150.00 mmol), (methoxymethyl)triphenylphosphine chloride (77.13 g, 225.00 mmol), and 750 mL of tetrahydrofuran were added to a reaction flask. The mixture was stirred and then cooled to below 0°C. Potassium tert-butoxide (1 M, in THF, 375 mL) was slowly added dropwise to the mixture. After the addition was complete, the temperature of the mixture was slowly increased, and the mixture was stirred at room temperature for 6.5 hours. After the reaction was completed, the mixture was cooled to room temperature, distilled water was added, and the mixture was extracted with dichloromethane. The mixture was allowed to stand and separated, and the organic layer was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. The mixture was cooled to allow crystals to form, filtered, and the resulting solid was recrystallized from toluene / methanol (8:1 v / v) to give intermediate d-4 (43.30 g, 80% yield). The purity of the solid was ≥99.76% as determined by HPLC.

[0207] Add d-4 (37.89 g, 105.00 mmol), 175 mL of Eaton reagent (7.7 wt% phosphorus pentoxide methanesulfonic acid solution), and 275 mL of chlorobenzene to the reaction flask. Reflux for 7.5 hours. After the reaction is complete, cool the mixture to room temperature, add distilled water, and extract with dichloromethane. Dry the organic phase with anhydrous magnesium sulfate, filter, concentrate the solvent by vacuum distillation, cool to crystallize, filter, and recrystallize with toluene to obtain intermediate e-4 (27.96 g, yield 81%). HPLC analysis showed a solid purity ≥99.83%.

[0208] E-4 (24.66 g, 75.00 mmol), pinacol diborate (20.32 g, 80.00 mmol), potassium acetate (14.72 g, 150.00 mmol), and DMF (400 mL) were added to the reaction flask. After purging the air three times with nitrogen, Pd(dppf)Cl2 (0.59 g, 0.80 mmol) was added. The mixture was heated and stirred for 8 hours. After the reaction was completed, the mixture was cooled to room temperature, distilled water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, the solvent was concentrated by vacuum distillation, and crystals were precipitated by cooling. The crystals were filtered and recrystallized from toluene to give intermediate A-4 (27.11 g, yield 86%); HPLC purity ≥99.88%. Mass spectrometry m / z: 420.1885 (theoretical value: 420.1897).

[0209] According to the above preparation method, the following intermediates were also synthesized in this invention:

[0210]

[0211]

[0212]

[0213] Synthesis Example 2: Preparation of Intermediate D-39

[0214]

[0215] Synthesis of intermediate M-39:

[0216] A-39 (25.22 g, 60.00 mmol), n-39 (11.49 g, 60.00 mmol), sodium carbonate (11.45 g, 108.00 mmol), and 240 mL of toluene / ethanol / water (2:1:1) mixed solvent were added to the reaction flask. After purging the air three times with nitrogen, tetrakis(triphenylphosphine)palladium (0.69 g, 0.60 mmol) was added to the reaction flask, and the reaction was carried out under reflux for 7 hours. After the reaction was completed, the mixture was cooled to room temperature, filtered, and the filter cake was obtained. The filter cake was recrystallized from toluene / ethanol at a ratio of 5:1 to obtain intermediate M-39 (20.16 g, yield 83%); HPLC purity ≥99.78%. Mass spectrometry m / z: 404.0979 (theoretical value: 404.0968).

[0217] Synthesis of intermediate D-39:

[0218] Under nitrogen protection, M-39 (18.22 g, 45.00 mmol), pinacol diboronate (12.70 g, 50.00 mmol), potassium acetate (8.83 g, 90.00 mmol), and DMF (240 mL) were added to the reaction flask. After purging the air with nitrogen three times, Pd(dppf)Cl2 (0.37 g, 0.50 mmol) was added to the reaction flask. The mixture was heated and stirred for 7.5 hours. After the reaction was completed, the mixture was cooled to room temperature, distilled water was added, and the mixture was extracted with dichloromethane. The organic layer was dried with anhydrous magnesium sulfate, the solvent was concentrated by vacuum distillation, and crystals were precipitated by cooling. The crystals were filtered and recrystallized from toluene to obtain intermediate D-39 (17.87 g, yield 80%); HPLC purity ≥99.85%. Mass spectrometry m / z: 496.2198 (theoretical value: 496.2210).

[0219] According to the above preparation method, the following intermediates were also synthesized in this invention:

[0220]

[0221] Synthesis Example 3: Preparation of Intermediate F-48

[0222]

[0223] Synthesis of intermediate E-48:

[0224] H-39 (17.65 g, 60.00 mmol), B'-48 (11.73 g, 60.00 mmol), sodium carbonate (11.45 g, 108.00 mmol), and 240 mL of toluene / ethanol / water (2:1:1) mixed solvent were added to the reaction flask. After purging the air three times with nitrogen, tetrakis(triphenylphosphine)palladium (0.69 g, 0.60 mmol) was added to the reaction flask, and the reaction was carried out under reflux for 6.5 hours. After the reaction was completed, the mixture was cooled to room temperature, filtered, and the filter cake was obtained. The filter cake was recrystallized from toluene / ethanol at a ratio of 5:1 to obtain intermediate E-48 (13.74 g, yield 81%); HPLC purity ≥99.78%. Mass spectrometry m / z: 282.0735 (theoretical value: 282.0749).

[0225] Synthesis of intermediate F-48:

[0226] Under nitrogen protection, E-48 (12.72 g, 45.00 mmol), pinacol diborate (12.70 g, 50.00 mmol), potassium acetate (8.83 g, 90.00 mmol), and DMF (240 mL) were added to the reaction flask. After purging the air with nitrogen three times, Pd(dppf)Cl2 (0.37 g, 0.50 mmol) was added to the reaction flask. The mixture was heated and stirred for 7 hours. After the reaction was completed, the mixture was cooled to room temperature, and distilled water was added. The mixture was then extracted with dichloromethane, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was concentrated by vacuum distillation, and the mixture was cooled to crystallize. The crystals were filtered and recrystallized from toluene to obtain intermediate F-48 (13.98 g, yield 83%); HPLC purity ≥99.88%. Mass spectrometry m / z: 374.1979 (theoretical value: 374.1991).

[0227] According to the above preparation method, the following intermediates were also synthesized in this invention:

[0228]

[0229] Synthesis Example 4: Preparation of Compound 4

[0230]

[0231] Synthesis of intermediate B-4:

[0232] Under nitrogen protection, f-4 (12.91 g, 70.00 mmol), g-4 (15.31 g, 75.00 mmol), potassium acetate (13.74 g, 140.00 mmol), Pd(dppf)Cl2 (0.51 g, 0.70 mmol), and 340 mL of THF were added to the reaction flask, and the mixture was reacted under reflux for 5 hours. After the reaction was completed, the mixture was cooled to room temperature, filtered to obtain a filter cake, and recrystallized from the filter cake using toluene / ethanol at a ratio of 10:1 to obtain intermediate B-4 (12.50 g, yield 79%); HPLC purity ≥99.82%. Mass spectrometry m / z: 224.9873 (theoretical value: 224.9861).

[0233] Synthesis of intermediate C-4:

[0234] Under nitrogen protection, B-4 (11.30 g, 50.00 mmol), h-4 (13.24 g, 45.00 mmol), potassium acetate (9.81 g, 100.00 mmol), Pd(dppf)Cl2 (0.37 g, 0.50 mmol), and 270 mL of THF were added to a reaction flask, and the mixture was reacted under reflux for 6 hours. After the reaction was completed, the mixture was cooled to room temperature, filtered, and the filter cake was obtained. The filter cake was recrystallized from toluene / ethanol at a ratio of 10:1 to give intermediate C-4 (14.31 g, yield 80%); HPLC purity ≥99.86%. Mass spectrometry m / z: 357.0682 (theoretical value: 357.0669).

[0235] Synthesis of compound 4:

[0236] Under nitrogen protection, C-4 (12.52 g, 35.00 mmol), A-4 (14.71 g, 35.00 mmol), sodium carbonate (7.42 g, 70.00 mmol), palladium acetate (0.08 g, 0.35 mmol), P(t-Bu)3 (0.20 g, 0.70 mmol), and 115 mL of THF were added to a reaction flask, and the mixture was reacted under reflux for 8 hours. After the reaction was completed, the mixture was cooled to room temperature, water was added, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous MgSO4, the solvent was removed under reduced pressure, and the mixture was recrystallized from toluene to give compound 4 (16.81, yield 78%); HPLC purity ≥99.93%. Mass spectrometry m / z: 615.1958 (theoretical value: 615.1947). Theoretical elemental content (%) C 43 H 25 N3O2: C, 83.88; H, 4.09; N, 6.83. Measured elemental content (%): C, 83.92; H, 4.14; N, 6.79.

[0237] Synthesis Example 5: Preparation of Compound 25

[0238]

[0239] Synthesis of intermediate B-25:

[0240] Under nitrogen protection, f-25 (22.35 g, 70.00 mmol), g-4 (15.31 g, 75.00 mmol), potassium acetate (13.74 g, 140.00 mmol), Pd(dppf)Cl2 (0.51 g, 0.70 mmol), and 340 mL of THF were added to the reaction flask, and the mixture was reacted under reflux for 5.5 hours. After the reaction was completed, the mixture was cooled to room temperature, filtered to obtain a filter cake, and recrystallized from the filter cake using toluene / ethanol at a ratio of 5:1 to obtain intermediate B-25 (15.28 g, yield 81%); HPLC purity ≥99.85%. Mass spectrometry m / z: 267.9416 (theoretical value: 267.9403).

[0241] Synthesis of intermediate C-25:

[0242] Under nitrogen protection, B-25 (13.48 g, 50.00 mmol), h-25 (15.50 g, 45.00 mmol), potassium acetate (9.81 g, 100.00 mmol), Pd(dppf)Cl2 (0.37 g, 0.50 mmol), and 250 mL of THF were added to a reaction flask, and the mixture was reacted under reflux for 7 hours. After the reaction was completed, the mixture was cooled to room temperature, filtered, and the filter cake was obtained. The filter cake was recrystallized from toluene / ethanol at a ratio of 5:1 to obtain intermediate C-25 (16.68 g, yield 82%); HPLC purity ≥99.87%. Mass spectrometry m / z: 406.0860 (theoretical value: 406.0873).

[0243] Synthesis of compound 25:

[0244] Under nitrogen protection, C-25 (14.24 g, 35.00 mmol), A-25 (17.37 g, 35.00 mmol), sodium carbonate (7.42 g, 70.00 mmol), palladium acetate (0.08 g, 0.35 mmol), P(t-Bu)3 (0.20 g, 0.70 mmol), and 100 mL THF were added to a reaction flask, and the mixture was reacted under reflux for 8 hours. After the reaction was completed, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous MgSO4, the solvent was removed under reduced pressure, and the mixture was recrystallized from toluene to give compound 25 (19.97 g, yield 77%); HPLC purity ≥99.91%. Mass spectrometry m / z: 740.2475 (theoretical value: 740.2464). Theoretical elemental content (%) C 54 H 32N2O2: C, 87.55; H, 4.35; N, 3.78. Measured elemental content (%): C, 87.50; H, 4.39; N, 3.81.

[0245] Synthesis Example 6: Preparation of Compound 39

[0246]

[0247] Following the same preparation method as compound 4 in Example 4, h-4 was replaced with an equimolar amount of h-39, and A-4 was replaced with an equimolar amount of D-39, yielding compound 39 (18.89 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 691.2273 (theoretical value: 691.2260). Theoretical elemental content (%) C 49 H 29 N3O2: C, 85.07; H, 4.23; N, 6.07. Measured elemental content (%): C, 85.11; H, 4.18; N, 6.10.

[0248] Synthesis Example 7: Preparation of Compound 48

[0249]

[0250] Following the same preparation method as compound 4 in Example 4, h-4 was replaced with an equimolar amount of F-48, and A-4 was replaced with an equimolar amount of A-39, yielding compound 48 (18.51 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 695.2524 (theoretical value: 695.2511). Theoretical elemental content (%) C 49 H 25 D4N3O2: C, 84.58; H, 4.78; N, 6.04. Measured elemental content (%): C, 84.63; H, 4.82; N, 6.01.

[0251] Synthesis Example 8: Preparation of Compound 74

[0252]

[0253] Following the same preparation method as compound 4 in Example 4, g-4 was replaced with an equimolar amount of g-74 to obtain compound 74 (19.52 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 763.2643 (theoretical value: 763.2655). Theoretical elemental content (%) C 52 H 37 N3O2Si: C, 81.75; H, 4.88; N, 5.50. Measured elemental content (%): C, 81.80; H, 4.92; N, 5.48.

[0254] Synthesis Example 9: Preparation of Compound 84

[0255]

[0256] Following the same preparation method as compound 25 in Synthesis Example 5, f-25 was replaced with an equimolar amount of f-84, g-4 with an equimolar amount of g-84, h-25 with an equimolar amount of F-84, and A-25 with an equimolar amount of A-84, yielding compound 84 (19.79 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 715.2248 (theoretical value: 715.2260). Theoretical elemental content (%) C 51 H 29 N3O2: C, 85.58; H, 4.08; N, 5.87. Measured elemental content (%): C, 85.62; H, 4.13; N, 5.90.

[0257] Synthesis Example 10: Preparation of Compound 102

[0258]

[0259] Following the same preparation method as compound 4 in Example 4, g-4 was replaced with an equimolar amount of g-102, h-4 with an equimolar amount of h-39, and A-4 with an equimolar amount of A-102, yielding compound 102 (18.99 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 704.2226 (theoretical value: 704.2212). Theoretical elemental content (%) C 49 H 28 N4O2: C, 83.51; H, 4.00; N, 7.95. Measured elemental content (%): C, 83.46; H, 3.97; N, 7.99.

[0260] Synthetic Example 11: Preparation of Compound 106

[0261]

[0262] Following the same preparation method as compound 4 in Example 4, g-4 was replaced with an equimolar amount of g-106, h-4 with an equimolar amount of h-39, and A-4 with an equimolar amount of A-39, yielding compound 106 (18.80 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 725.3055 (theoretical value: 725.3042). Theoretical elemental content (%) C 51 H 39N3O2: C, 84.39; H, 5.42; N, 5.79. Measured elemental content (%): C, 84.44; H, 5.38; N, 5.82.

[0263] Synthesis Example 12: Preparation of Compound 112

[0264]

[0265] Following the same preparation method as compound 4 in Example 4, g-4 was replaced with an equimolar amount of g-112, and A-4 was replaced with an equimolar amount of A-39, yielding compound 112 (18.91 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 692.2201 (theoretical value: 692.2212). Theoretical elemental content (%) C 48 H 28 N4O2: C, 83.22; H, 4.07; N, 8.09. Measured elemental content (%): C, 83.17; H, 4.11; N, 8.12.

[0266] Synthesis Example 13: Preparation of Compound 125

[0267]

[0268] Following the same preparation method as compound 4 in Example 4, g-4 was replaced with an equimolar amount of h-39, h-4 was replaced with an equimolar amount of h-39, and A-4 was replaced with an equimolar amount of A-39, yielding compound 125 (18.77 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 705.2065 (theoretical value: 705.2052). Theoretical elemental content (%) C 49 H 27 N3O3: C, 83.39; H, 3.86; N, 5.95. Measured elemental content (%): C, 83.44; H, 3.90; N, 5.92.

[0269] Synthesis Example 14: Preparation of Compound 133

[0270]

[0271] Following the same preparation method as compound 4 in Example 4, h-4 was replaced with an equimolar amount of h-133, and A-4 was replaced with an equimolar amount of A-133, yielding compound 133 (18.06 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 687.2332 (theoretical value: 687.2344). Theoretical elemental content (%) C 47 H 33N3OS: C, 82.07; H, 4.84; N, 6.11. Measured elemental content (%): C, 82.11; H, 4.79; N, 6.08.

[0272] Synthesis Example 15: Preparation of Compound 142

[0273]

[0274] Following the same preparation method as compound 4 in Example 4, h-4 was replaced with an equimolar amount of h-142, and A-4 was replaced with an equimolar amount of A-142, yielding compound 142 (18.19 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 649.1637 (theoretical value: 649.1624). Theoretical elemental content (%) C 43 H 24 FN3OS: C, 79.49; H, 3.72; N, 6.47. Measured elemental content (%): C, 79.54; H, 3.68; N, 6.50.

[0275] Synthetic Example 16: Preparation of Compound 150

[0276]

[0277] Following the same preparation method as compound 4 in Example 4, h-4 was replaced with an equimolar amount of h-150, and A-4 was replaced with an equimolar amount of A-150 to obtain compound 150 (17.07 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 580.1371 (theoretical value: 580.1358). Theoretical elemental content (%) C 38 H 20 N4OS: C, 78.60; H, 3.47; N, 9.65. Measured elemental content (%): C, 78.55; H, 3.51; N, 9.69.

[0278] Synthesis Example 17: Preparation of Compound 160

[0279]

[0280] Following the same preparation method as compound 4 in Example 4, h-4 was replaced with an equimolar amount of F-160, and A-4 was replaced with an equimolar amount of A-160, yielding compound 160 (18.58 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 707.2019 (theoretical value: 707.2031). Theoretical elemental content (%) C 49 H 29N3OS: C, 83.14; H, 4.13; N, 5.94. Measured elemental content (%): C, 83.09; H, 4.07; N, 5.98.

[0281] Synthesis Example 18: Preparation of Compound 260

[0282]

[0283] Following the same preparation method as compound 4 in Synthesis Example 4, g-4 was replaced with an equimolar amount of g-260, h-4 with an equimolar amount of h-260, and A-4 with an equimolar amount of A-39, yielding compound 260 (18.96 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 712.2334 (theoretical value: 712.2345). Theoretical elemental content (%) C 49 H 24 D5N3OS: C, 82.56; H, 4.81; N, 5.89. Measured elemental content (%): C, 82.61; H, 4.77; N, 5.92.

[0284] Synthetic Example 19: Preparation of Compound 295

[0285]

[0286] Following the same preparation method as compound 25 in Synthesis Example 5, f-25 was replaced with an equimolar amount of f-295, g-4 with an equimolar amount of g-295, h-25 with an equimolar amount of h-295, and A-25 with an equimolar amount of A-295, yielding compound 295 (19.06 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 735.1127 (theoretical value: 735.1114). Theoretical elemental content (%) C 45 H 22 F5NS2: C, 73.46; H, 3.01; N, 1.90. Measured elemental content (%): C, 73.51; H, 2.97; N, 1.86.

[0287] Synthesis Example 20: Preparation of Compound 321

[0288]

[0289] Following the same preparation method as compound 4 in Example 4, h-4 was replaced with an equimolar amount of h-39, and A-4 was replaced with an equimolar amount of A-321, yielding compound 321 (18.10 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 615.1958 (theoretical value: 615.1947). Theoretical elemental content (%) C 43H 25 N3O2: C, 83.88; H, 4.09; N, 6.83. Measured elemental content (%): C, 83.92; H, 4.14; N, 6.79.

[0290] Synthesis Example 21: Preparation of Compound 352

[0291]

[0292] Following the same preparation method as compound 4 in Example 4, h-4 was replaced with an equimolar amount of h-39, and A-4 was replaced with an equimolar amount of D-352, yielding compound 352 (19.13 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 691.2247 (theoretical value: 691.2260). Theoretical elemental content (%) C 49 H 29 N3O2: C, 85.07; H, 4.23; N, 6.07. Measured elemental content (%): C, 85.11; H, 4.08; N, 6.10.

[0293] Synthesis Example 22: Preparation of Compound 361

[0294]

[0295] Following the same preparation method as compound 25 in Synthesis Example 5, f-25 was replaced with an equimolar amount of f-361, h-25 with an equimolar amount of h-4, and A-25 with an equimolar amount of D-361, yielding compound 361 (18.54 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 687.2356 (theoretical value: 687.2342). Theoretical elemental content (%) C 46 H 33 N3O2Si: C, 80.32; H, 4.84; N, 6.11. Measured elemental content (%): C, 80.28; H, 4.79; N, 6.08.

[0296] Synthesis Example 23: Preparation of Compound 371

[0297]

[0298] Following the same preparation method as compound 4 in Example 4, g-4 was replaced with an equimolar amount of g-371, h-4 with an equimolar amount of F-371, and A-4 with an equimolar amount of A-371, yielding compound 371 (18.34 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 717.2152 (theoretical value: 717.2165). Theoretical elemental content (%) C 49 H27 N5O2: C, 81.99; H, 3.79; N, 9.76. Measured elemental content (%): C, 82.04; H, 3.83; N, 9.80.

[0299] Synthesis Example 24: Preparation of Compound 372

[0300]

[0301] Following the same preparation method as compound 4 in Example 4, g-4 was replaced with an equimolar amount of g-372, h-4 with an equimolar amount of h-39, and A-4 with an equimolar amount of A-321, yielding compound 372 (18.40 g). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 691.2249 (theoretical value: 691.2260). Theoretical elemental content (%) C 49 H 29 N3O2: C, 85.07; H, 4.23; N, 6.07. Measured elemental content (%): C, 85.12; H, 4.09; N, 6.11.

[0302] Synthesis Example 25: Preparation of Compound 385

[0303]

[0304] Following the same preparation method as compound 25 in Synthesis Example 5, g-4 was replaced with an equimolar amount of g-385, h-25 with an equimolar amount of h-39, and A-25 with an equimolar amount of A-385, yielding compound 385 (19.70 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 792.2537 (theoretical value: 792.2525). Theoretical elemental content (%) C 56 H 32 N4O2: C, 84.83; H, 4.07; N, 7.07. Measured elemental content (%): C, 84.78; H, 4.11; N, 7.10.

[0305] Synthesis Example 26: Preparation of Compound 405

[0306]

[0307] Following the same preparation method as compound 4 in Synthesis Example 4, g-4 was replaced with an equimolar amount of h-260, h-4 with an equimolar amount of h-39, and A-4 with an equimolar amount of A-405, yielding compound 405 (18.70 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 721.1811 (theoretical value: 721.1824). Theoretical elemental content (%) C49 H 27 N3O2S: C, 81.53; H, 3.77; N, 5.82. Measured elemental content (%): C, 81.49; H, 3.82; N, 5.79.

[0308] Synthesis Example 27: Preparation of Compound 421

[0309]

[0310] Following the same preparation method as compound 4 in Example 4, h-4 was replaced with an equimolar amount of h-421, and A-4 was replaced with an equimolar amount of D-421, yielding compound 421 (18.61 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 681.1886 (theoretical value: 681.1875). Theoretical elemental content (%) C 47 H 27 N3OS: C, 82.80; H, 3.99; N, 6.16. Measured elemental content (%): C, 82.75; H, 4.02; N, 6.20.

[0311] Synthesis Example 28: Preparation of Compound 432

[0312]

[0313] Following the same preparation method as compound 4 in Example 4, g-4 was replaced with an equimolar amount of g-432, h-4 with an equimolar amount of h-39, and A-4 with an equimolar amount of A-432, yielding compound 432 (19.30 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 765.2802 (theoretical value: 765.2814). Theoretical elemental content (%) C 53 H 39 N3OS: C, 83.11; H, 5.13; N, 5.49. Measured elemental content (%): C, 83.08; H, 5.09; N, 5.52.

[0314] Synthesis Example 29: Preparation of Compound 502

[0315]

[0316] Following the same preparation method as compound 4 in Example 4, h-4 was replaced with an equimolar amount of h-260, and A-4 was replaced with an equimolar amount of A-502, yielding compound 502 (19.21 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 731.2043 (theoretical value: 731.2031). Theoretical elemental content (%) C 51 H29 N3OS: C, 83.70; H, 3.99; N, 5.74. Measured elemental content (%): C, 83.64; H, 4.04; N, 5.71.

[0317] Synthesis Example 30: Preparation of Compound 516

[0318]

[0319] Following the same preparation method as compound 4 in Example 4, h-4 was replaced with an equimolar amount of h-516, and A-4 was replaced with an equimolar amount of D-516, yielding compound 516 (18.23 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 667.1519 (theoretical value: 667.1530). Theoretical elemental content (%) C 43 H 23 F2N3OS: C, 77.35; H, 3.47; N, 6.29. Measured elemental content (%): C, 77.40; H, 3.51; N, 6.32.

[0320] Synthesis Example 31: Preparation of Compound 545

[0321]

[0322] Following the same preparation method as compound 4 in Example 4, g-4 was replaced with an equimolar amount of h-260, h-4 with an equimolar amount of h-545, and A-4 with an equimolar amount of A-321, yielding compound 545 (19.63 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 747.2359 (theoretical value: 747.2344). Theoretical elemental content (%) C 52 H 33 N3OS: C, 83.51; H, 4.45; N, 5.62. Measured elemental content (%): C, 83.47; H, 4.50; N, 5.59.

[0323] Synthesis Example 32: Preparation of Compound 560

[0324]

[0325] Following the same preparation method as compound 4 in Synthesis Example 4, g-4 was replaced with an equimolar amount of g-560, h-4 with an equimolar amount of h-560, and A-4 with an equimolar amount of A-560, yielding compound 560 (18.81 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 697.1660 (theoretical value: 697.1646). Theoretical elemental content (%) C 47 H27 N3S2: C, 80.89; H, 3.90; N, 6.02. Measured elemental content (%): C, 80.93; H, 3.85; N, 5.98.

[0326] Synthesis Example 33: Preparation of Compound 585

[0327]

[0328] Following the same preparation method as compound 25 in Synthesis Example 5, f-25 was replaced with an equimolar amount of f-585, h-25 with an equimolar amount of h-260, and A-25 with an equimolar amount of D-585, yielding compound 585 (18.51 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 695.1753 (theoretical value 695.1741). Theoretical elemental content (%) C 49 H 29 NS2: C, 84.57; H, 4.20; N, 2.01. Measured elemental content (%): C, 84.62; H, 4.16; N, 1.98.

[0329] Synthesis Example 34: Preparation of Compound 598

[0330]

[0331] Following the same preparation method as compound 4 in Synthesis Example 4, g-4 was replaced with an equimolar amount of g-598, h-4 with an equimolar amount of h-39, and A-4 with an equimolar amount of A-598, yielding compound 598 (18.33 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 707.2020 (theoretical value: 707.2031). Theoretical elemental content (%) C 49 H 29 N3OS: C, 83.14; H, 4.13; N, 5.94. Measured elemental content (%): C, 83.09; H, 4.08; N, 5.97.

[0332] Synthesis Example 35: Preparation of Compound 609

[0333]

[0334] Following the same preparation method as compound 4 in Example 4, g-4 was replaced with an equimolar amount of g-609, and A-4 was replaced with an equimolar amount of A-609, yielding compound 609 (18.11 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 638.2680 (theoretical value: 638.2668). Theoretical elemental content (%) C 44 H18 D9N3O2: C, 82.73; H, 5.68; N, 6.58. Measured elemental content (%): C, 82.69; H, 5.73; N, 6.61.

[0335] Synthesis Example 36: Preparation of Compound 618

[0336]

[0337] Following the same preparation method as compound 4 in Example 4, g-4 was replaced with an equimolar amount of g-618, and A-4 was replaced with an equimolar amount of A-618 to obtain compound 618 (17.10 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 574.1864 (theoretical value: 574.1876). Theoretical elemental content (%) C 38 H 18 D5N3OS: C, 79.42; H, 4.91; N, 7.31. Measured elemental content (%): C, 79.38; H, 4.86; N, 7.28.

[0338] Synthesis Example 37: Preparation of Compound 671

[0339]

[0340] Following the same preparation method as compound 4 in Example 4, h-4 was replaced with an equimolar amount of h-39, and A-4 was replaced with an equimolar amount of A-671, yielding compound 671 (17.61 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 613.2167 (theoretical value: 613.2154). Theoretical elemental content (%) C 44 H 27 N3O: C, 86.11; H, 4.43; N, 6.85. Measured elemental content (%): C, 86.07; H, 4.38; N, 6.88.

[0341] Synthesis Example 38: Preparation of Compound 680

[0342]

[0343] Following the same preparation method as compound 4 in Example 4, A-4 was replaced with an equimolar amount of A-680 to obtain compound 680 (18.86 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 690.2409 (theoretical value: 690.2420). Theoretical elemental content (%) C 49 H 30N4O: C, 85.20; H, 4.38; N, 8.11. Measured elemental content (%): C, 85.17; H, 4.43; N, 8.07.

[0344] Device Example 1: Fabrication of a Red Organic Light Emitting Device

[0345] First, the ITO glass substrate is rinsed three times in distilled water and ultrasonically washed for 20 minutes. Then, it is rinsed twice more in distilled water and ultrasonically washed for 10 minutes. After the distilled water rinsing is completed, it is ultrasonically washed in sequence with solvents such as isopropanol, acetone, and methanol. It is then dried at 120°C and sent to the vapor deposition machine.

[0346] On the aforementioned glass substrate, a HI-1 film is deposited as a hole injection layer with a thickness of 10 nm. HT-1 is then vacuum-deposited on the hole injection layer as a hole transport layer with a thickness of 120 nm. EB-1 is then vacuum-deposited on the hole transport layer as an electron blocking layer with a thickness of 50 nm. Compound 4 of the present invention, as the first host material, RH-2, as the second host material, and RD-1, as the dopant material (mass ratio 49:49:2), are then vacuum-deposited on the electron blocking layer to form a light-emitting layer with a thickness of 35 nm. Then, ET-1 and Liq are vacuum-deposited on the light-emitting layer as an electron transport layer (mass ratio 1:1) with a thickness of 30 nm. LiF is then vacuum-deposited on the electron transport layer as an electron injection layer with a thickness of 1.0 nm. Finally, Al is vacuum-deposited on the electron injection layer as a cathode with a thickness of 160 nm, thereby fabricating an organic electroluminescent device.

[0347]

[0348] Device Examples 2-35:

[0349] Compounds 25, 39, 48, 74, 84, 102, 106, 112, 125, 133, 142, 150, 160, 260, 295, 321, 352, 361, 371, 372, 385, 405, 421, 432, 502, 516, 545, 560, 585, 598, 609, 618, 671, and 680 of the present invention were used to replace compound 4 in device example 1 as the light-emitting layer. Otherwise, an organic electroluminescent device was prepared using the same preparation method as device example 1.

[0350] Comparative devices: Examples 1-4

[0351] Comparative Examples 1-4: Fabrication of Comparative Organic Electroluminescent Devices 1-4

[0352] By replacing compound 4 in the light-emitting layer of Example 1 with comparative compounds 1 to 4, and keeping the other steps the same, comparative organic electroluminescent devices 1 to 4 were obtained.

[0353] 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.

[0354] The test environment was atmospheric, and the temperature was room temperature. The luminescence characteristics test results of devices 1-35 in the device embodiments of the present invention, and those obtained in comparative embodiments 1-4 are shown in Table 1 below.

[0355] Table 1:

[0356]

[0357]

[0358]

[0359] As shown in Table 1, when the nitrogen-containing fused aromatic ring compound described in this invention is used as the host material of the emitting layer of organic electroluminescent devices, it has a high triplet energy level, which can effectively prevent energy back-transfer from the guest material to the host material. The matching of its HOMO / LUMO energy level with the corresponding energy levels of the adjacent hole transport layer and electron transport layer can obtain a small injection barrier, which significantly reduces the device driving voltage. This indicates that the nitrogen-containing fused aromatic ring compound described in this invention is a class of high-performance host materials for the emitting layer of OLEDs.

[0360] Device Example 36: Fabrication of a Green Organic Light Emitting Device

[0361] After cleaning and drying, the ITO glass substrate is transferred to an evaporation machine. A HI-2 film with a hole injection layer and a thickness of 12 nm is deposited on the glass substrate. HT-2 is then vacuum-deposited on the hole injection layer as a hole transport layer with a thickness of 130 nm. EB-2 is then vacuum-deposited on the hole transport layer as an electron blocking layer with a thickness of 40 nm. GH-1 is then vacuum-deposited on the electron blocking layer as a first host material, GH-2 as a second host material, and GD-1 as a dopant material (mass ratio 47:47:6) to form a light-emitting layer with a thickness of 40 nm. Then, compound 4 and Liq of the present invention are vacuum-deposited on the light-emitting layer as an electron transport layer (mass ratio 1:1) with a thickness of 32 nm. LiF is then vacuum-deposited on the electron transport layer as an electron injection layer with a thickness of 1.1 nm. Finally, Al is vacuum-deposited on the electron injection layer as a cathode with a thickness of 170 nm, thereby fabricating an organic electroluminescent device.

[0362]

[0363] Device Examples 37–70:

[0364] Compounds 25, 39, 48, 74, 84, 102, 106, 112, 125, 133, 142, 150, 160, 260, 295, 321, 352, 361, 371, 372, 385, 405, 421, 432, 502, 516, 545, 560, 585, 598, 609, 618, 671, and 680 of the present invention were used to replace compound 4 in device example 36 as the electron transport layer material. Otherwise, an organic electroluminescent device was prepared using the same preparation method as device example 36.

[0365] Comparative device examples 5-8:

[0366] Comparative Examples 5-8: Fabrication of Comparative Organic Electroluminescent Devices 5-8

[0367] The compounds in the electron transport layer of Example 36 were replaced with comparative compounds 5-8, and the other steps were the same to obtain comparative organic electroluminescent devices 5-8.

[0368] 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.

[0369] The test environment was atmospheric, and the temperature was room temperature. The luminescence characteristics test results of the organic electroluminescent devices obtained in the device embodiments of the present invention (devices 36-70) and comparative embodiments 5-8 are shown in Table 2 below.

[0370] Table 2:

[0371]

[0372]

[0373] As shown in Table 2, when the nitrogen-containing fused aromatic ring compounds described in this invention are used as electron transport layer materials for organic electroluminescent devices, they exhibit high electron mobility and electrophilicity, stable electrochemical and electric field stability, and can effectively transport electrons to the light-emitting layer, ensuring matching with the work function of the cathode and withstanding high electric fields. This indicates that the nitrogen-containing fused aromatic ring compounds described in this invention are a class of high-performance electron transport layer materials for OLEDs.

[0374] Device Example 71: Fabrication of a Green Organic Light Emitting Device

[0375] After cleaning and drying, the ITO glass substrate was transferred to an evaporation machine. A HI-2 film was deposited on the glass substrate as a hole injection layer with a thickness of 12 nm. HT-2 was then vacuum-deposited on the hole injection layer as a hole transport layer with a thickness of 130 nm. EB-2 was then vacuum-deposited on the hole transport layer as an electron blocking layer with a thickness of 40 nm. Finally, GH-1 was vacuum-deposited on the electron blocking layer as the first host material, GH-2 as the second host material, and GD-1 as a dopant material (mass ratio: [missing information]). A light-emitting layer with a thickness of 40 nm is formed by vacuum evaporation of compound 4 of the present invention as a hole-blocking layer with a thickness of 20 nm; then, ET-2 and Liq (mass ratio 1:1) are vacuum evaporated on the hole-blocking layer as an electron transport layer with a thickness of 32 nm; LiF is vacuum evaporated on the electron transport layer as an electron injection layer with a thickness of 1.1 nm; and Al is vacuum evaporated on the electron injection layer as a cathode with a thickness of 170 nm, thereby preparing an organic electroluminescent device.

[0376]

[0377] Device Examples 72-105:

[0378] Compounds 25, 39, 48, 74, 84, 102, 106, 112, 125, 133, 142, 150, 160, 260, 295, 321, 352, 361, 371, 372, 385, 405, 421, 432, 502, 516, 545, 560, 585, 598, 609, 618, 671, and 680 of the present invention were used to replace compound 4 in device example 71 as hole blocking layer materials. Otherwise, an organic electroluminescent device was prepared using the same preparation method as device example 71.

[0379] Comparative device examples 9-12:

[0380] Comparative Examples 9-12: Fabrication of Comparative Organic Electroluminescent Devices 9-12

[0381] The compounds in the hole blocking layer of Example 71 were replaced with comparative compounds 9-12, and the other steps were the same to obtain comparative organic electroluminescent devices 9-12.

[0382] 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.

[0383] The test environment was atmospheric, and the temperature was room temperature. The luminescence characteristics test results of the organic electroluminescent devices obtained in the device embodiments of the present invention (devices 72-105) and comparative embodiments 9-12 are shown in Table 3 below.

[0384] Table 3:

[0385]

[0386]

[0387]

[0388] As shown in Table 3, when the nitrogen-containing fused aromatic ring compound described in this invention is used as a hole blocking layer material for organic electroluminescent devices, it has a high triplet energy level and good hole blocking ability. It can effectively prevent holes in the light-emitting layer from escaping to the electron transport layer, so that electrons and holes in the light-emitting layer recombine efficiently, thereby improving the luminous efficiency of organic electroluminescent devices. This indicates that the nitrogen-containing fused aromatic ring compound described in this invention is a class of high-performance hole blocking layer materials for OLEDs.

[0389] 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 compound containing a nitrogen-containing fused aromatic ring, characterized in that, The nitrogen-containing fused aromatic ring compound is at least one of the compounds of formula I-1, I-5, I-7, I-9, I-11, and I-13: Wherein, n is selected from 0 or 1; The Selected from any one of the following groups: This group is connected to L1 via a five-membered ring; X is selected from O or S; The T is selected from CH; R1 is independently selected from any one or a combination of hydrogen, deuterium, tritium, substituted or unsubstituted C1 to C6 alkyl groups; The R2 is independently selected from any one or a combination of hydrogen, deuterium, tritium, substituted or unsubstituted C1 to C6 alkyl groups; The n1 is selected from 0, 1, or 2; the n5 is selected from 0, 1, 2, 3, or 4; the n6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8. The R y Selected from any one of hydrogen, deuterium, tritium, and C1-C6 alkyl groups; One of Ar2 and Ar3 is selected from the group shown in 1-a or 1-b. The groups shown in formulas 1-a and 1-b are selected from one of the following: The R3 is independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1 to C6 alkyl groups; The n3 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the n4 is selected from 0, 1, 2, 3, 4, 5 or 6; the n7 is selected from 0, 1, 2 or 3; the n8 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; When Ar2 and Ar3 are not of formulas 1-a and 1-b, they are selected from one of the following groups: The R4 is independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C12 cycloalkyl; The k1 is selected from 0, 1, 2, 3, 4 or 5; The L1 is selected from one of a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group; Each of L2 to L3 is independently selected from one of single-bonded, substituted, or unsubstituted phenylene compounds; The term "substitution..." refers to the independent substitution by one or more of the following groups: deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, isopropyl, and tert-butyl.

2. The nitrogen-containing fused aromatic ring compound according to claim 1, characterized in that, The Selected from any one of the following groups: This group is connected to L1 via a five-membered ring.

3. The compound containing a nitrogen-containing fused aromatic ring according to claim 1, characterized in that, The groups shown in formulas 1-a and 1-b are selected from one of the following: 。 4. The compound containing a nitrogen-containing fused aromatic ring according to claim 1, characterized in that, When Ar2 and Ar3 are not of formulas 1-a and 1-b, they are selected from one of the following groups: The R4 is independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1 to C6 alkyl groups.

5. A compound containing a nitrogen-containing fused aromatic ring, characterized in that, The nitrogen-containing fused aromatic ring is selected from at least one of the following structures: 。 6. 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, characterized in that, The organic layer comprises at least one of an electron transport layer or a hole blocking layer, wherein the at least one of the electron transport layer or hole blocking layer comprises at least one of the nitrogen-containing fused aromatic ring compounds according to any one of claims 1 to 5.

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, characterized in that, The organic layer includes a light-emitting layer, which contains at least one of the nitrogen-containing fused aromatic ring compounds according to any one of claims 1 to 5.

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