Heterocyclic compound and organic electroluminescent device thereof

Abstract

The invention provides a heterocyclic compound and an organic electroluminescent device thereof, and relates to the technical field of organic electroluminescent materials. The heterocyclic compound has relatively high electron mobility and triplet state energy level, and can be used as an efficient electron transport layer material and a hole blocking layer material to improve the recombination effect of excitons; when the compound is applied to the organic electroluminescent device, the driving voltage of the device can be reduced, and the luminous efficiency can be improved. And meanwhile, the excellent thermal stability and film-forming property are favorable for guaranteeing the long-acting stability of the device.

Description

Technical Field

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

[0002] Organic light-emitting diodes (OLEDs) have gained widespread application and continued development in the display and lighting fields due to their outstanding characteristics such as wide viewing angle, high brightness, wide color gamut, high efficiency, thinness and flexibility, fast response, and low driving voltage. The performance advantages of OLEDs fundamentally stem from their organic semiconductor material system. As the core of light emission and charge transport in the device, the optimization of the structure and properties of this material directly determines the device's efficiency, stability, and functional performance.

[0003] The basic structure of an OLED typically consists of an anode, a cathode, and organic layers in between. These organic layers generally include hole injection layers, hole transport layers, electron blocking layers, and light-emitting layers. The light-emitting mechanism is as follows: under an applied electric field, holes and electrons are injected from the anode and cathode respectively, migrate to the light-emitting layer, and recombine to form excitons; subsequently, the excitons release photons through radiative transitions, achieving a direct conversion of electrical energy into light energy. To achieve high-efficiency energy conversion, the selection of the various organic functional materials in the device is crucial. This requires not only appropriate energy level matching between the layers to reduce the injection and transport barriers, but also precise control of the mobility of holes and electrons to achieve dynamic equilibrium and effective recombination within the light-emitting layer, thereby maximizing exciton generation efficiency and reducing non-radiative energy loss.

[0004] In OLEDs, ideal electron transport / hole blocking materials need to meet two requirements: firstly, the LUMO level should be deep enough to facilitate efficient electron injection and transport from the cathode; secondly, the HOMO level should be high enough to form a barrier, preventing holes from leaking from the emissive layer to the cathode, thereby confining electrons and holes within the emissive layer for efficient recombination and light emission. However, existing materials often fail to meet both requirements simultaneously: most electron transport materials have low intrinsic electron mobility, limiting electron transport efficiency; while many hole blocking materials have insufficient HOMO levels to effectively block holes, leading to exciton quenching and efficiency loss.

[0005] To fundamentally overcome the bottlenecks of OLEDs in terms of driving voltage, external quantum efficiency, and operating life, developing organic electroluminescent functional layer materials with high mobility, stable energy levels, and excellent film-forming properties has become a key path to improve the overall performance of devices. Summary of the Invention

[0006] To address the aforementioned problems, this invention provides a heterocyclic compound for organic electroluminescent devices. This heterocyclic compound can improve electron mobility, suppress hole diffusion, enhance carrier recombination efficiency, and improve light extraction efficiency, thereby comprehensively optimizing the overall performance of the device.

[0007] This invention provides a heterocyclic compound having the structure shown in Formula 1.

[0008] The X atoms may be the same or different from each other, are selected from C(R1) or N atoms, and have at least one N atom. When X is bonded to other groups, X is selected from C. The R1 is independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic group, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaromatic ring, or two adjacent R1s bonded together to form a substituted or unsubstituted ring; The Y atoms may be the same or different from each other, are selected from C(R2) or N atoms, and have at least one N atom. When Y is bonded to other groups, Y is selected from C. The R2 is independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic group, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaromatic ring, or two adjacent R2s bonded together to form a substituted or unsubstituted ring; The P is selected from the structure shown in formula 1-a. "This refers to the connection points with X, Y, and L;

[0009] The Q atoms may be the same or different from each other, and are selected from C(R3) or N atoms; The R3 is independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic group, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaromatic ring, or two adjacent R3s bonded together to form a substituted or unsubstituted ring; The Ar is selected from the structure shown in Formula 1-1; The z atoms may be the same or different from each other, and are selected from C(R4) or N atoms. When z is bonded to other groups, the z atoms are selected from C. The E is selected from O, S, C(R5)(R6) or N(R7); The R4, R5, and R6 are independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic group, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaromatic ring, or two adjacent R4 are bonded to form a substituted or unsubstituted ring, or two adjacent R5 and R6 are bonded to form a substituted or unsubstituted ring; The R7 is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic group, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, and fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaromatic ring; The R is independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic group, fused cycloyl group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, and fused cycloyl group of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaromatic ring; The n is selected from 0, 1, or 2; The L, L1, L2, L3, and L4 are independently selected from any one of the following: single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C3-C30 heteroarylene, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic rings, and substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaromatic rings. Ar1, Ar2, Ar3, and Ar4 are independently selected from any one of the following: substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 heteroaryl groups, substituted or unsubstituted C3-C20 alicyclic groups, fused cyclic groups of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic groups, and fused cyclic groups of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaromatic groups. The present invention also provides an organic electroluminescent device, comprising an anode, a cathode, and an organic layer disposed between the anode and the cathode, the organic layer comprising at least one of the heterocyclic compounds described in the present invention.

[0010] Beneficial effects: This invention provides a heterocyclic compound with high electron mobility and a deep HOMO energy level, which can be used as a highly efficient electron transport layer material and hole blocking layer material to improve exciton recombination. Its application in organic electroluminescent devices helps reduce device driving voltage and improve luminous efficiency. Simultaneously, its excellent thermal stability and film-forming properties help ensure the long-term stability of the device. Detailed Implementation

[0011] The present invention will be further explained and illustrated below with reference to specific embodiments. It should be noted that these embodiments are merely examples to aid in understanding the present invention and are not intended to limit the scope of the invention. All other embodiments obtained by those skilled in the art based on the embodiments disclosed in this invention without inventive effort should be covered within the protection scope of this invention.

[0012] In this specification, " "This refers to the portion that is connected to another substituent."

[0013] In this specification, when the position of the substituent on the ring is not fixed, it means that it can be attached to any of the corresponding optional sites on the ring. For example, Can represent , , ; Can represent , , ; Can represent , , , , , , , , , And so on.

[0014] 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.

[0015] In this invention, "forming a ring by connecting two adjacent groups" refers to the formation of substituted or unsubstituted aromatic rings, heteroaromatic rings, aliphatic rings, or aliphatic heterocycles by combining adjacent groups with each other and optionally aromatizing them. Examples are shown below:

[0016] The term "adjacent groups" refers to two substituents on two directly connected atoms, a substituent positioned spatially closest to the corresponding substituent, or another substituent on an atom with a corresponding substituent. For example, two substituents substituted at the ortho position of a benzene ring or two substituents on the same carbon atom in an alicyclic ring can be considered "adjacent" to each other.

[0017] The aliphatic ring and the aliphatic heterocycle can be saturated or unsaturated rings. Specifically, the rings formed can be three-membered, four-membered, five-membered, six-membered, seven-membered, spirocyclic, or fused rings. The aromatic ring formed preferably has 6 to 30 carbon atoms, particularly preferably 6 to 18 carbon atoms, more preferably 6 to 15 carbon atoms, and most preferably 6 to 12 carbon atoms. The heteroaromatic ring formed preferably has 3 to 30 carbon atoms, particularly preferably 3 to 18 carbon atoms, and most preferably 3 to 12 carbon atoms. The aliphatic ring formed preferably has 3 to 20 carbon atoms, particularly preferably 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, and most preferably 3 to 8 carbon atoms. Furthermore, the rings formed by the connection can be, for example, benzene, naphthalene, indene, cyclopentene, cyclopentane, cyclopentanophenene, cyclohexene, cyclohexane, cyclohexanophenene, pyridine, quinoline, isoquinoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, phenanthrene, or pyrene, but are not limited to these.

[0018] Examples of halogen atoms described in this invention may include fluorine, chlorine, bromine, or iodine.

[0019] The alkyl group described in this invention refers to a monovalent group in an alkane molecule after removing one hydrogen atom. 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 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 group is preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, etc., but is not limited thereto.

[0020] The silyl group mentioned in this invention refers to -Si(R) f )3 groups, wherein each R f The same or different groups are selected from the following: hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 alicyclic group, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, or fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaryl. Preferably, each R f The same or different groups are selected from the following: hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 alicyclic group, substituted or unsubstituted C6-C30 aryl. The alkyl group preferably has C1-C20 carbon atoms, more preferably C1-C12, and most preferably C1-C6. The alicyclic group preferably has C3-C20 carbon atoms, more preferably C3-C12, and most preferably C3-C6. The aryl group preferably has C6-C30 carbon atoms, more preferably C6-C18, and most preferably C6-C12. Preferably, each R... fThe same or different groups are selected from the following: 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 cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, 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. Preferably, the substituted silyl groups specifically include, but are not limited to, trimethylsilyl, triethylsilyl, triisopropylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc.

[0021] The alicyclic group described in this invention refers to a monovalent group obtained by removing one hydrogen atom from a cyclic aliphatic molecule. It can be cycloalkyl, cycloalkenyl, or cycloynyl; preferably having 3 to 20 carbon atoms, more preferably having 3 to 12 carbon atoms, and particularly preferably having 3 to 6 carbon atoms. Examples may include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cycloheptane, cyclooctane, adamantane, norbornyl, cyclopropene, cyclopentenyl, cyclohexenyl, cyclopentadienyl, cyclohexadiene, cyclooctatetraene, cyclopentynyl, cyclooctyne, decahydronaphthalene, perhydroanthracene, perhydrophenanthrene, etc., but are not limited thereto.

[0022] The aryl group described in this invention refers to 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 having 6 to 30 carbon atoms, more preferably 6 to 18 carbon atoms, and particularly preferably 6 to 12 carbon atoms. The aryl group can be substituted or unsubstituted. 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, such as biphenyl, terphenyl, tetraphenyl, 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, such as naphthyl, anthracene, phenanthrene, pyrene, peryl, thionyl, triphenylene, fluoranthyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, benzo[a]fluorenyl, 9,9'-spirodifluorenyl, etc., but not limited to this.

[0023] 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. These heteroatoms include, but are not limited to, oxygen, sulfur, nitrogen, silicon, or phosphorus atoms, and preferably have 3 to 30 carbon atoms, more preferably 3 to 18 carbon atoms, and particularly preferably 3 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. The heteroaryl group can be substituted or unsubstituted. 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.

[0024] 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 30 carbon atoms, more preferably 6 to 18 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, anthraceneene, phenanthrene, pyreneene, terphenylene, fluoranthracene, etc., but are not limited to.

[0025] The heteroaryl group described in this invention 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 3 to 30 carbon atoms, more preferably 3 to 18 carbon atoms, and most preferably 3 to 12 carbon atoms. The linking site of the heteroaryl group can be located on a cyclic carbon atom or a cyclic nitrogen atom. The heteroaryl group can be a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a fused-ring heteroaryl group. 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.

[0026] The fused cyclic group of alicyclic and aromatic rings described in this invention refers to the general term for a monovalent group remaining after removing one hydrogen atom from the fused alicyclic and aromatic rings. Preferably, the alicyclic ring has 3 to 20 carbon atoms, more preferably 3 to 12 carbon atoms, and particularly preferably 3 to 6 carbon atoms; the aromatic ring preferably has 6 to 30 carbon atoms, more preferably 6 to 18 carbon atoms, and most preferably 6 to 12 carbon atoms. The fused cyclic group of alicyclic and aromatic rings may include, but is not limited to, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentenyl, benzocyclohexenyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, benzocycloheptane, benzocycloheptenyl, etc.

[0027] 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 alicyclic and heteroaromatic rings are fused together. Preferably, the alicyclic ring has 3 to 20 carbon atoms, more preferably 3 to 12 carbon atoms, and particularly preferably 3 to 6 carbon atoms; the heteroaromatic ring preferably has 3 to 30 carbon atoms, more preferably 3 to 18 carbon atoms, and most preferably 3 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.

[0028] In this invention, "substituted or unsubstituted" as used in terms such as "substituted or unsubstituted alkyl, substituted or unsubstituted silyl, substituted or unsubstituted alicyclic, substituted or unsubstituted heterocyclic, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted arylene, substituted or unsubstituted heteroaryl" means that at least one hydrogen atom on the group is replaced by a substituent. When multiple hydrogens are replaced by multiple substituents, the multiple substituents may be the same or different. The substituents include, but are not limited to, the following groups: deuterium, tritium, cyano, nitro, hydroxyl, halogen atom, substituted or unsubstituted silyl group, substituted or unsubstituted C1-C20 alkyl group, substituted or unsubstituted C2-C20 alkenyl group, substituted or unsubstituted C3-C20 alicyclic group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C3-C30 heteroaryl group, substituted or unsubstituted C1-C20 alkoxy group, substituted or unsubstituted C1-C20 alkylthio group, substituted or unsubstituted C1-C20 alkylamino group, substituted or unsubstituted C6-C30 aryloxy group, substituted or unsubstituted C6-C30 arylamino group, etc. The substituents are preferably the following groups: deuterium, tritium, cyano, fluorine, chlorine, bromine, iodine, nitro, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cyclobutenyl, cyclopentenyl, cyclohexenyl, adamantyl, norbornyl, trifluoromethyl, trifluoroethyl, trimethylsilyl, triethylsilyl, tri-tert-butylsilyl, triphenylsilyl, trideuterylmethyl, methoxy, ethoxy, phenyl, biphenyl, terphenyl, naphthyl, phenanthrene, triphenylene, anthracene, pyrene, phenyl, fluoranyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzo[] Cyclohexyl, benzocycloheptyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, 9,9'-spirodifluorenyl, diphenylamino, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl, benzoquinolinyl, benzoisoquinolinyl, phenanthrolinel, oxazolyl, benzooxazolyl, thiazolyl, benzothiazolyl, imidazolyl, benzoimidazolyl, benzothiadiazolyl, benzooxiadiazolyl, benzotriazolyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, indolyl, carbazoleyl, etc., but not limited to these. Furthermore, each of the above substituents can be substituted or unsubstituted, and two adjacent substituents can be linked to form a ring.

[0029] The terms "at least one" and "one or more" as used in this invention may include one, two, three, four, five, six, or more, where permitted.

[0030] This invention provides a heterocyclic compound having the structure shown in Formula 1.

[0031] The X atoms may be the same or different from each other, are selected from C(R1) or N atoms, and have at least one N atom. When X is bonded to other groups, X is selected from C. The R1 is independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic group, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaromatic ring, or two adjacent R1s bonded together to form a substituted or unsubstituted ring; The Y atoms may be the same or different from each other, are selected from C(R2) or N atoms, and have at least one N atom. When Y is bonded to other groups, Y is selected from C. The R2 is independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic group, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaromatic ring, or two adjacent R2s bonded together to form a substituted or unsubstituted ring; The P is selected from the structure shown in formula 1-a. "This refers to the connection points with X, Y, and L;

[0032] The Q atoms may be the same or different from each other, and are selected from C(R3) or N atoms; The R3 is independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic group, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaromatic ring, or two adjacent R3s bonded together to form a substituted or unsubstituted ring; The Ar is selected from the structure shown in Formula 1-1; The z atoms may be the same or different from each other, and are selected from C(R4) or N atoms. When z is bonded to other groups, the z atoms are selected from C. The E is selected from O, S, C(R5)(R6) or N(R7); The R4, R5, and R6 are independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic group, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaromatic ring, or two adjacent R4 are bonded to form a substituted or unsubstituted ring, or two adjacent R5 and R6 are bonded to form a substituted or unsubstituted ring; The R7 is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic group, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, and fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaromatic ring; The R is independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic group, fused cycloyl group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, and fused cycloyl group of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaromatic ring; The n is selected from 0, 1, or 2; The L, L1, L2, L3, and L4 are independently selected from any one of the following: single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C3-C30 heteroarylene, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic rings, and substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaromatic rings. Ar1, Ar2, Ar3, and Ar4 are independently selected from any one of the following: substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 heteroaryl groups, substituted or unsubstituted C3-C20 alicyclic groups, fused cyclic groups of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic groups, and fused cyclic groups of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaromatic groups.

[0033] Preferably, the heterocyclic compound of Formula 1 is selected from any one of the following structures:

[0034]

[0035] The limitations of P, Ar, Ar1, Ar2, Ar3, Ar4, L, L1, L2, L3, L4, R1, and R2 are the same as those in Formula 1; t1 is selected from 0 or 1; t2 is selected from 0, 1 or 2; The q1 is selected from 0 or 1; the q2 is selected from 0, 1 or 2.

[0036] More preferably, the heterocyclic compound of Formula 1 is selected from any one of the following structures:

[0037]

[0038]

[0039]

[0040]

[0041] Preferably, P is selected from any of the following structures:

[0042] “ "This refers to the connection points with X, Y, and L; The R3 mentioned is the same as the limitation in Equation 1.

[0043] More preferably, R3 is independently selected from hydrogen, deuterium, cyano, fluorine, chlorine, bromine, iodine, or selected from any one or a combination of the following groups, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, benzo[a]cyclopropane, benzo[a]cyclobutane, benzo[a]cyclopentane, benzo[a]cyclohexane, benzo[a]cycloheptane, benzo[a]cyclopentenyl, benzo[a]cyclohexenyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, phenylenetriene, pyrene, hydroxyl, perylene, Fluoranthryl, acenaphthyl, fluorenyl, furanyl, thiophene, benzofuranyl, benzothiophene, pyridofuranyl, pyridothiophene, dibenzofuranyl, dibenzothiophene, carbazoyl, pyridinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl, naphthinyl, o-phenanthrolinel, oxazolyl, thiazoyl, benzooxazolyl, benzothiazoyl, pyridooxazolyl, pyridothiazoyl, trimethylsilyl, triethylsilyl, tri-tert-butylsilyl, triphenylsilyl, or two adjacent R3 bonds forming a substituted or unsubstituted benzene ring.

[0044] Preferably, the Choose from any of the following structures:

[0045]

[0046]

[0047]

[0048]

[0049]

[0050]

[0051]

[0052]

[0053]

[0054]

[0055]

[0056]

[0057] The R4, R5, and R6 are independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic group, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaromatic ring, or two adjacent R4 are bonded to form a substituted or unsubstituted ring, or two adjacent R5 and R6 are bonded to form a substituted or unsubstituted ring; The R7 is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic group, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, and fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaromatic ring; The R is independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic group, fused cycloyl group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, and fused cycloyl group of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaromatic ring; The n is selected from 0, 1, or 2; the n1 is selected from 0 or 1; The m1 is selected from 0, 1, 2, 3, or 4; the m2 is selected from 0, 1, 2, or 3; the m3 is selected from 0, 1, or 2; the m4 is selected from 0 or 1; the m5 is selected from 0, 1, 2, 3, 4, 5, or 6; the m6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the m7 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. More preferably, R4, R5, and R6 are independently selected from hydrogen, deuterium, cyano, fluorine, chlorine, bromine, iodine, or selected from any one or a combination of the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, benzo[a]cyclopropane, benzo[a]cyclobutane, benzo[a]cyclopentane, benzo[a]cyclohexane, benzo[a]cycloheptane, benzo[a]cyclopentenyl, benzo[a]cyclohexenyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, phenylenetriene, pyrene, alkyl, perylene. alkyl, fluoranthyl, acenaphthyl, fluorenyl, furanyl, thiophene, benzofuranyl, benzothiophene, pyridofuranyl, pyridothiophene, dibenzofuranyl, dibenzothiophene, carbazoyl, pyridinyl, pyrimidinyl, pyrazinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, o-phenanthrolinel, oxazolyl, thiazoyl, benzooxazolyl, benzothiazoyl, pyridooxazolyl, pyridothiazoyl, trimethylsilyl, triethylsilyl, tri-tert-butylsilyl, triphenylsilyl, or two adjacent R5 and R6 bonds forming substituted or unsubstituted rings; More preferably, R7 is independently selected from hydrogen, deuterium, or any one or a combination thereof selected from substituted or unsubstituted groups of the following: cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, pyridinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthraceneyl, phenanthrene, triphenylene, pyrene, β-carboxyl, etc. alkyl, peryl, fluoranyl, acenaphthel, fluorenyl, furanyl, thiopheneyl, oxazolyl, thiazolyl, o-phenanthrolinel, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiopheneyl, pyridofuranyl, pyridothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzooxazolyl, benzothiazolyl, pyridooxazolyl, pyridothiazolyl; More preferably, R is independently selected from hydrogen, deuterium, cyano, fluorine, chlorine, bromine, iodine, or selected from any one or a combination of the following groups, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, pyridinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, adamantyl, norbornelyl, phenyl, biphenyl, terphenyl, naphthyl, anthraceneyl, phenanthrene. Triphenylene, pyrene, phenyl, peryl, fluoranyl, acenaphthene, fluorenyl, furanyl, thiophene, oxazolyl, thiazolyl, o-phenanthrolinel, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophene, pyridofuranyl, pyridothiophene, dibenzofuranyl, dibenzothiophene, benzooxazolyl, benzothiazolyl, pyridooxazolyl, pyridothiazolyl, trimethylsilyl, triphenylsilyl.

[0058] Preferably, Ar1, Ar2, Ar3, and Ar4 are the same or different and are selected from any of the following structures:

[0059]

[0060]

[0061] The v may be the same as or different from each other, and are selected from C (R8) or N atoms. When v is bonded to other groups, the v is selected from C. The t atoms may be the same or different from each other, and are selected from C (Ra) or N atoms. When t is bonded to other groups, the t atoms are selected from C. The ring A is independently selected from substituted or unsubstituted C3 to C20 alicyclic rings; The Gs may be the same or different from each other, and are selected from any one of O, S, C(R1′)(R2′) or N(R3′); The R8 is independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic group, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaromatic ring, or two adjacent R8s bonded together to form a substituted or unsubstituted ring; The Ra is independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic group, fused cycloyl group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, and fused cycloyl group of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaromatic ring; The R1′ and R2′ are independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic group, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaromatic ring, or two adjacent R1′ and R2′ are bonded to form a substituted or unsubstituted ring; The R3′ is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic group, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, and fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaromatic ring; More preferably, Ar1, Ar2, Ar3, and Ar4 are the same or different and are selected from any of the following structures:

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081] The R8 is independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic group, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaromatic ring, or two adjacent R8s bonded together to form a substituted or unsubstituted ring; The Ra is independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic group, fused cycloyl group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, and fused cycloyl group of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaromatic ring; The R1′ and R2′ are independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic group, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaromatic ring, or two adjacent R1′ and R2′ are bonded to form a substituted or unsubstituted ring; The R3′ is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic group, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, and fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaromatic ring; a1 is selected from 0, 1, 2, 3, 4, or 5; a2 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; a3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; a4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; a5 is selected from 0, 1, 2, 3, or 4; a6 is selected from 0, 1, 2, or 3; a7 is selected from 0, 1, 2, 3, 4, 5, or 6; a8 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; a9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; a1 is selected from 0, 1, 2, 3, 4, or 5; a 10 Selected from 0, 1, or 2; the a 11 Selected from 0 or 1; Preferably, R8 is independently selected from hydrogen, deuterium, cyano, fluorine, chlorine, bromine, iodine, or selected from any one or a combination of the following groups, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentenyl, benzocyclohexenyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, phenylenetriene, pyrene, phenyl, peryl, fluoranyl, acenaphthene, fluorenyl Furanyl, thiopheneyl, benzofuranyl, benzothiopheneyl, pyridofuranyl, pyridothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, carbazoyl, pyridinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl, naphthidyl, o-phenanthrolinel, oxazolyl, thiazoyl, benzooxazolyl, benzothiazoyl, pyridooxazolyl, pyridothiazoyl, trimethylsilyl, triethylsilyl, tri-tert-butylsilyl, triphenylsilyl, or two adjacent R8 bonds forming substituted or unsubstituted benzene rings, naphthyl rings, anthracene rings, phenanthrene rings, furan rings or thiophene rings; The Ra is independently selected from hydrogen, deuterium, cyano, fluorine, chlorine, bromine, iodine, or selected from any one or a combination of the following groups, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, pyridinyl, pyridinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, adamantyl, norbornelyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenyl Phenylidene, pyrene, phenyl, peryl, fluoranyl, acenaphthene, fluorenyl, furanyl, thiophene, oxazolyl, thiazolyl, o-phenanthrolinel, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophene, pyridofuranyl, pyridothiophene, dibenzofuranyl, dibenzothiophene, benzooxazolyl, benzothiazolyl, pyridooxazolyl, pyridothiazolyl, trimethylsilyl, triphenylsilyl; R1′ and R2′ are independently selected from hydrogen, deuterium, cyano, fluorine, chlorine, bromine, iodine, or selected from any one or a combination of the following groups, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, pyridinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, adamantyl, norbornelyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, phenylenetriene , pyrene, phenyl, peryl, fluoranyl, acenaphthene, fluorenyl, furanyl, thiophene, oxazolyl, thiazolyl, o-phenanthrolinel, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophene, pyridofuranyl, pyridothiophene, dibenzofuranyl, dibenzothiophene, benzooxazolyl, benzothiazolyl, pyridooxazolyl, pyridothiazolyl, or two adjacent R1′, R2′ bonds forming substituted or unsubstituted rings; The R3′ is independently selected from hydrogen, deuterium, or any one or a combination thereof selected from the following groups, substituted or unsubstituted: cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, pyridinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthraceneyl, phenanthrene, triphenylene, pyrene, hydroxyl, etc. Peryl, fluoranthracene, acenaphthene, fluorenyl, furanyl, thiophene, oxazolyl, thiazolyl, o-phenanthroline, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophene, pyridofuranyl, pyridothiophene, dibenzofuranyl, dibenzothiophene, benzooxazolyl, benzothiazolyl, pyridooxazolyl, pyridothiazolyl.

[0082] Preferably, one, two, three, or four identical or different Ar1, Ar2, Ar3, and Ar4 are selected from any of the following structures: .

[0083] Preferably, the L, L1, L2, L3, and L4 are the same or different and are selected from single bonds or any of the following structures:

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096] The W is selected from O, S, or N(R6′); The R9 is independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic group, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaromatic ring, or two adjacent R9s bonded together to form a substituted or unsubstituted ring; The Rb is independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic group, fused cycloyl group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, and fused cycloyl group of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaromatic ring; The R4′ and R5′ are independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic group, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaromatic ring, or two adjacent R4′ and R5′ are bonded to form a substituted or unsubstituted ring; The R6′ is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic group, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, and fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaromatic ring; The number b1 is selected from 0, 1, 2, 3, or 4; the number b2 is selected from 0, 1, 2, 3, 4, 5, or 6; the number b3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the number b4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; the number b5 is selected from 0, 1, 2, or 3; the number b6 is selected from 0, 1, or 2; the number b7 is selected from 0 or 1; the number b8 is selected from 0, 1, 2, 3, 4, or 5; and the number b9 is selected from 0, 1, 2, 3, 4, 5, 6, or 7.

[0097] More preferably, R9 is independently selected from hydrogen, deuterium, cyano, fluorine, chlorine, bromine, iodine, or selected from any one or a combination of the following groups, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentenyl, benzocyclohexenyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, phenylenetriene, pyrene, phenyl, peryl, fluoranyl, acenaphthene, fluorenyl Furanyl, thiopheneyl, benzofuranyl, benzothiopheneyl, pyridofuranyl, pyridothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, carbazoyl, pyridinyl, pyrimidinyl, pyrazinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl, naphthinyl, o-phenanthrolinel, oxazolyl, thiazoyl, benzooxazolyl, benzothiazoyl, pyridooxazolyl, pyridothiazoyl, trimethylsilyl, triethylsilyl, tri-tert-butylsilyl, triphenylsilyl, or two adjacent R9 bonds forming substituted or unsubstituted benzene rings, naphthyl rings, anthracene rings, phenanthrene rings, furan rings or thiophene rings; The Rb is independently selected from hydrogen, deuterium, cyano, fluorine, chlorine, bromine, iodine, or selected from any one or a combination of the following groups, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, pyridinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, adamantyl, norbornelyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenyl Phenylidene, pyrene, phenyl, peryl, fluoranyl, acenaphthene, fluorenyl, furanyl, thiophene, oxazolyl, thiazolyl, o-phenanthrolinel, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophene, pyridofuranyl, pyridothiophene, dibenzofuranyl, dibenzothiophene, benzooxazolyl, benzothiazolyl, pyridooxazolyl, pyridothiazolyl, trimethylsilyl, triphenylsilyl; R4′ and R5′ are independently selected from hydrogen, deuterium, cyano, fluorine, chlorine, bromine, iodine, or selected from any one or a combination of the following groups, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, pyridinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, adamantyl, norbornelyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene , pyrene, phenyl, peryl, fluoranyl, acenaphthene, fluorenyl, furanyl, thiophene, oxazolyl, thiazolyl, o-phenanthrolinel, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophene, pyridofuranyl, pyridothiophene, dibenzofuranyl, dibenzothiophene, benzooxazolyl, benzothiazolyl, pyridooxazolyl, pyridothiazolyl, or two adjacent R4′, R5′ bonds forming substituted or unsubstituted rings; The R6′ is independently selected from hydrogen, deuterium, or any one or a combination thereof selected from the following groups, substituted or unsubstituted: cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, pyridinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthraceneyl, phenanthrene, triphenylene, pyrene, hydroxyl, etc. Peryl, fluoranthracene, acenaphthene, fluorenyl, furanyl, thiophene, oxazolyl, thiazolyl, o-phenanthroline, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophene, pyridofuranyl, pyridothiophene, dibenzofuranyl, dibenzothiophene, benzooxazolyl, benzothiazolyl, pyridooxazolyl, pyridothiazolyl.

[0098] Most preferably, the heterocyclic compound is selected from any one of the following structures:

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234]

[0235]

[0236]

[0237]

[0238]

[0239]

[0240]

[0241]

[0242]

[0243]

[0244]

[0245]

[0246]

[0247]

[0248]

[0249]

[0250]

[0251]

[0252]

[0253]

[0254]

[0255]

[0256]

[0257]

[0258]

[0259]

[0260]

[0261]

[0262]

[0263]

[0264]

[0265]

[0266]

[0267]

[0268]

[0269]

[0270]

[0271]

[0272]

[0273]

[0274]

[0275]

[0276]

[0277]

[0278]

[0279]

[0280]

[0281]

[0282]

[0283]

[0284]

[0285]

[0286]

[0287]

[0288]

[0289]

[0290]

[0291]

[0292]

[0293]

[0294]

[0295]

[0296]

[0297]

[0298]

[0299]

[0300]

[0301] The above lists some specific structural forms of heterocyclic compounds represented by Formula 1 according to the present invention. However, the present invention is not limited to these chemical structures. Any structure based on the structure shown in Formula 1, with substituents as defined above, should be included.

[0302] This invention also provides a method for preparing the compound of Formula 1, the specific synthetic route of which is shown below, but is not limited thereto: [Synthetic route of compound Equation 1] when and When the represented structures are the same, the synthetic route for compound 1 is as follows: ; when and When the represented structures are different, the synthetic route for compound 1 is as follows:

[0303] ; Qa, Qb, and Qc are independently selected from Cl, Br, or I; The Qe is independently selected from Or B(OH)2; The Qt independent selection ; Intermediate a” can be prepared by the following method:

[0304] or

[0305] Qa, Qb, and Qc are independently selected from Cl, Br, or I; The Qe is independently selected from Or B(OH)2; The Qt independent selection .

[0306] The present invention also provides an organic electroluminescent device comprising at least one of the heterocyclic compounds described in the present invention.

[0307] 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, and the organic layer contains at least one of the heterocyclic compounds described in this invention.

[0308] Preferably, the organic electroluminescent device of the present invention may comprise one or more organic layers, wherein the organic layers may include a light-emitting layer, a hole injection layer, a hole transport layer, a charge generation layer, an electron transport layer, an electron injection layer, a hole blocking layer, an electron blocking layer, etc. The organic layers may be formed as a single-layer structure or as a multi-layer structure with stacked organic layers; furthermore, each organic layer may also comprise 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 comprise fewer or more organic layers.

[0309] Preferably, the organic layer includes a light-emitting layer containing at least one of the heterocyclic compounds described in this invention.

[0310] Preferably, the organic layer comprises at least one of an electron transport layer and a hole blocking layer, wherein the at least one of the electron transport layer and the hole blocking layer comprises at least one of the heterocyclic compounds described in this invention.

[0311] 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 heterocyclic compounds described in this invention.

[0312] 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 heterocyclic compounds described in this invention.

[0313] Preferably, the organic layer is located between the anode and the cathode, the organic layer contains two or more light-emitting units, and a charge-generating layer is contained between two adjacent light-emitting units, the charge-generating layer containing at least one of the heterocyclic compounds described in this invention.

[0314] This invention does not particularly limit the materials of the thin films in the organic electroluminescent device; substances known in the art can be used. The organic functional layers of the aforementioned organic electroluminescent device and the electrodes on both sides of the device are described below: The organic electroluminescent device of the present invention is typically formed on a substrate. The substrate can be any material that remains unchanged when forming electrodes or organic layers, such as glass, plastic, polymer films, silicon, etc.

[0315] The anode material described in this invention preferably uses a material with a high functional function and improved hole injection efficiency. The anode includes, but is not limited to, the materials described below: metal oxides, combinations of metals and oxides, metals or alloys thereof, multilayer materials, conductive polymers, etc. Specific examples may include gold (Au), platinum (Pt), magnesium (Mg), silver (Ag), aluminum (Al), calcium (Ca), indium zinc oxide (IZO), indium tin oxide (ITO), tin oxide (SnO2), zinc oxide (ZnO), aluminum-lithium (Al-Li), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof, but are not limited thereto. The anode can have a single-layer structure or a multilayer structure comprising 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 is not limited thereto.

[0316] The hole injection layer material of the present invention is a material with good hole acceptance capability and suitable HOMO energy level and other properties. The hole injection layer material includes, but is not limited to, the following materials: metal oxides, phthalocyanine metal complexes, aromatic amine derivatives, polycyano conjugated organic materials, quinacridone compounds, anthraquinone compounds, and conductive polymers based on polyaniline and polythiophene. Specific examples may include molybdenum trioxide (MoO3), vanadium pentoxide (V2O5), copper phthalocyanine (CuPC), N,N'-bis[4-di(m-tolyl)aminophenyl]-N,N'-diphenylbenzidine (DNTPD), 4,4',4"-tris(N(1-naphthyl)-N-phenylamino)triphenylamine (1-TNATA), 1,4,5,8,9,11-hexaazabenzonitrile (HAT-CN), poly(4-vinyltriphenylamine) (PVTPA), etc., but is not limited to these.

[0317] The hole transport layer of the present invention is preferably made of a material with good stability and high hole mobility. The hole transport layer includes, but is not limited to, the following materials: carbazole compounds, triaromatic amine compounds, benzidine diamine compounds, fluorene compounds, phthalocyanine compounds, anthraquinone compounds, polyaniline, polythiophene, polyvinylcarbazole, etc. Specific examples may include, but are not limited to, 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-[1-[4-[di(4-methylphenyl)amino]phenyl]cyclohexyl]-N-(3-methylphenyl)-N-(4-methylphenyl)aniline (TAPC), N,N,N',N'-tetra(3-methylphenyl)-3,3'-dimethylbiphenyldiamine (HMTPD), etc.

[0318] In the organic electroluminescent device of the present invention, the electron blocking layer material is preferably a material with a high LUMO energy level and a high hole mobility. The electron blocking material includes, but is not limited to, aromatic amine derivatives, carbazole derivatives, spirofluorene derivatives, etc. Specific examples may include N,N'-bis(naphthyl-1-yl)-N,N'-diphenyl-benzidine (NPD), N,N-bis([1,1'-biphenyl]-4-)-(9H-carbazole-9-yl)-[1,1'-biphenyl]-4-amine, etc., but are not limited thereto.

[0319] The luminescent layer of this invention comprises a host material and doped materials. The host material of the luminescent layer not only needs to possess bipolar charge transport properties but also requires appropriate energy levels to effectively transfer excitation energy to the guest luminescent material. The host material can be one material or two or more materials. The host material includes, but is not limited to, heterocyclic compounds, metal complexes, fused polycyclic aromatic hydrocarbons, and aromatic amine compounds. Specific examples may include 4,4'-bis(carbazole-9-yl)biphenyl (CBP), 9,9'-(1,3-phenyl)bis-9H-carbazole (mCP), 4,4',4”-tris(carbazole-9-yl)triphenylamine (TCTA), 1,3,5-tris(carbazole-9-yl)benzene (TCP), and 9,10-bis(2-naphthyl)anthracene (ADN), but is not limited to these.

[0320] The doping material of the luminescent layer of the present invention can be a fluorescent material, a phosphorescent material, a TADF material, or a combination thereof. The doping material includes, but is not limited to, the following: metal complexes, aromatic amine derivatives, styrene amine compounds, fused aromatic compounds, heterocyclic compounds, etc. Specific examples may include tris(2-phenylpyridine)iridium (Ir(ppy)3), bis(1-phenyl-isoquinoline)(acetylacetone)iridium (Ir(piq)2(acac)), tris(1-phenyl-isoquinoline)iridium (Ir(piq)3), 2,5,8,11-tetratert-butylperylene (TBPe), tris[2-(3-methyl-2-pyridyl)phenyl]iridium (Ir(3mppy)3), tris(2-(3,5-dimethylphenyl)quinoline-C2,N')iridium (Ir(dmpq)3), etc., but are not limited thereto.

[0321] The charge generation layer material described in this invention includes n-type charge generation materials and p-type charge generation materials.

[0322] The N-type charge-generating layer material described in this invention is preferably a material with high electron mobility, strong electron-withdrawing properties, and good chemical stability. The N-type charge-generating layer material may include, but is not limited to, tris-(8-hydroxyquinoline)aluminum (Alq3), lithium quinoline (Liq), bis(2-methyl-8-quinoline-N1,O8)-(1,1'-biphenyl-4-phenololine)aluminum (BAlq), 4,7-diphenyl-1,10-phenanthroline (Bphen), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), and 1,3,5-tris(p-pyridin-3-yl-phenyl)benzene (TpPyPB). Furthermore, it may include auxiliary N-type charge-generating materials, which may be alkali metals or alkaline earth metals, such as Li, Cs, K, Rb, Na, Fr, Be, Mg, Ca, Sr, Ba, or Ra, but are not limited to these. Heterocyclic compounds described in this invention are preferred.

[0323] The P-type charge generation layer material described in this invention is preferably a material with good hole injection and hole migration capabilities. The P-type charge generation layer material may include, but is not limited to, 4,4',4”-tris(3-methylphenylamino)triphenylamine (MTDATA), 4,4',4”-tris(N,N-diphenyl-amino)triphenylamine (NATA), tris(4-carbazolyl-9-yl-phenyl)amine (TCTA), N,N'-diphenyl-N,N'-bis(1-naphthyl)-1,1'-biphenyl-4,4”-diamine (NPD), 4,4',4”-tris(N-(naphthyl-2-yl)-N-phenyl-amino)triphenylamine (2T-NATA), copper phthalocyanine (CuPc), etc.

[0324] The hole-blocking layer material described in this invention preferably uses a material with suitable energy levels and hole-blocking capability. The hole-blocking layer material includes, but is not limited to, phenanthrene-roline derivatives, rare earth derivatives, imidazole derivatives, oxazole derivatives, oxadiazole derivatives, triazole derivatives, triazine derivatives, quinoline derivatives, diazanphenanthrene derivatives, azirbenzene derivatives, anthrone derivatives, etc. Specific examples may include 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene (TPBi), 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), bis(2-methyl-8-hydroxyquinoline)(4-phenylphenol)aluminum(III) (BAlq), etc., but is not limited to these. Heterocyclic compounds described in this invention are preferred.

[0325] The electron transport layer material described in this invention preferably possesses good stability and high electron mobility, enabling it to effectively receive electrons from the cathode and transfer them to the light-emitting layer. The electron transport layer material includes, but is not limited to, metal complexes, oxazole derivatives, thiazole derivatives, quinoline derivatives, triazine derivatives, and polymeric compounds. Specific examples may include lithium 8-hydroxyquinolineate (LiQ), aluminum 8-hydroxyquinoline (Alq3), bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,4'-bis(4,6-diphenyl-1,3,5-triazin-2-yl)biphenyl (BTB), but is not limited to these. Heterocyclic compounds described in this invention are preferred.

[0326] The electron injection layer of this invention is preferably made of a material with good electron injection capability. The electron injection layer material includes, but is not limited to, alkali metals, alkali metal compounds, alkali metal complexes, alkaline earth metal complexes, and rare earth metal complexes. Specific examples may include ytterbium (Yb), lithium fluoride (LiF), magnesium fluoride (MgF), lithium 8-hydroxyquinoline (LiQ), cesium carbonate (Cs₂CO₃), rubidium acetate (CH₃COORb), lithium oxide (Li₂O), etc., but are not limited to these.

[0327] The cathode material described in this invention preferably uses a material with a low work function that can promote electron injection into the organic layer, thereby reducing the electron injection barrier. The cathode material includes, but is not limited to, metals, alloys, and mixtures thereof with low work functions. Specific examples may include metals such as gold (Au), platinum (Pt), magnesium (Mg), calcium (Ca), sodium (Na), potassium (K), nickel (Ni), titanium (Ti), indium (In), lithium (Li), aluminum (Al), silver (Ag), tin (Sn), or lead (Pb), as well as LiF / Al or LiO2 / Al multilayer structures, but are not limited to these.

[0328] The light efficiency improvement layer material of this invention preferably possesses strong ultraviolet absorption, high refractive index, and uniform film formation. The light efficiency improvement layer material includes, but is not limited to, alkali metal complexes, metal oxides, metal nitrides, aromatic amine compounds, benzimidazole derivatives, benzoxazole derivatives, benzothiazole derivatives, triazole derivatives, benzidine derivatives, etc. Specific examples may include, but are not limited to, tris(8-hydroxyquinoline)aluminum (Alq3), 4,4'-bis(carbazole-9-yl)biphenyl (CBP), zirconium oxide (ZrO), zinc oxide (ZnO), etc.

[0329] The present invention does not impose any special restrictions on the thickness of each organic layer of the organic electroluminescent device; thicknesses commonly used in the field can be adopted.

[0330] There are no particular limitations on the preparation method of each thin film in the organic electroluminescent device of the present invention. Vacuum evaporation, sputtering, spin coating, spraying, screen printing, laser transfer, etc. can be used, but are not limited to these methods.

[0331] The organic electroluminescent device of the present invention can be a top-emitting type, a bottom-emitting type, or a bidirectional-emitting type.

[0332] The organic electroluminescent device of this invention is mainly used in the fields of information display technology and lighting. In terms of information display, it is widely used in various information displays, such as mobile phones, tablet computers, flat-screen TVs, smartwatches, VR, in-vehicle systems, digital cameras, wearable devices, etc.

[0333] The manufacture of compounds represented by Formula 1 above and organic electroluminescent devices containing them is specifically described in the following examples. However, the following examples are merely illustrative of this specification, and the scope of this specification is not limited to these examples.

[0334] Raw materials and reagents: The present invention does not impose any particular restrictions on the raw materials or reagents used in the following synthesis examples. They can be commercially available products or prepared using methods well known to those skilled in the art.

[0335] Testing instruments: G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer (Waters Corporation, UK); VarioELcube organic elemental analyzer (Elementar Corporation, Germany).

[0336] [Synthetic Example 1] Preparation of intermediate a”-86:

[0337] Preparation of intermediate a”-86: Under nitrogen protection, a”-86 (17.69 g, 60 mmol), pinacol diborate (15.24 g, 60 mmol), and K2CO3 (16.59 g, 120 mmol) were added to a reaction flask, followed by 450 mL of LDM. After purging the air with nitrogen three times, Pd(PPh3)4 (0.69 g, 0.60 mmol) was added. The mixture was heated and stirred for 6.0 h. After the reaction was completed, the reactants were cooled to room temperature, and distilled water was added. The mixture was extracted with dichloromethane, separated, and the organic phase was washed three times with distilled water and dried with anhydrous magnesium sulfate. The obtained solid was purified by recrystallization from toluene:ethanol = 20:5 (v / v) to obtain intermediate a”-86 (19.70 g, yield 85%), with HPLC purity ≥99.87% and mass spectrometry m / z: 386.1501 (theoretical value: 386.1512).

[0338] By substituting the raw materials accordingly and following the preparation method of intermediate a”-86 in Synthesis Example 1, intermediates a”-889, a”-954, and a”-994 can be prepared. The raw materials are shown in the table below: Table 1:

[0339] [Synthetic Example 2] Preparation of intermediate a”-115:

[0340] Preparation of intermediate a'-115: Under nitrogen protection, a-11 (15.61 g, 60 mmol), n-115 (16.89 g, 60 mmol), K2CO3 (12.44 g, 90 mmol), Pd(PPh3)4 (0.69 g, 0.6 mmol), and 200 mL of toluene / ethanol / water (2:1:1) mixed solvent were added to a reaction flask. The mixture was stirred and reacted under reflux for 6 hours. After the reaction was completed, the mixture was cooled to room temperature and filtered to obtain a filter cake. The filter cake was recrystallized from toluene:ethanol = 5:1 (v / v) to obtain intermediate a'-115 (17.28 g, yield 86%); HPLC purity ≥ 99.87%. Mass spectrometry m / z: 334.0237 (theoretical value: 334.0219).

[0341] Preparation of intermediate a”-115: Under nitrogen protection, a”-115 (13.39 g, 40 mmol), pinacol diboronate (10.16 g, 40 mmol), and K2CO3 (11.06 g, 80 mmol) were added to a reaction flask, followed by 500 mL of LDM. After purging the air with nitrogen three times, Pd(PPh3)4 (0.46 g, 0.40 mmol) was added. The mixture was heated and stirred for 6.0 h. After the reaction was completed, the reactants were cooled to room temperature, and distilled water was added. The mixture was extracted with dichloromethane, separated, and the organic phase was washed three times with distilled water and dried with anhydrous magnesium sulfate. The obtained solid was purified by recrystallization from toluene:ethanol = 20:5 (v / v) to obtain intermediate a”-115 (14.32 g, yield 84%), with HPLC purity ≥99.82% and mass spectrometry m / z: 426.1446 (theoretical value: 426.1461).

[0342] By substituting the raw materials accordingly and following the preparation method of intermediate a”-115 in Synthesis Example 2, intermediates a”-133, a”-137, a”-307, and a”-928 can be prepared. The raw materials are shown in the table below: Table 1:

[0343] [Synthetic Example 3] Preparation of Compound 6:

[0344] Preparation of intermediate A-6: Under nitrogen protection, a-6 (26.02 g, 100.00 mmol), b-6 (22.59 g, 100.00 mmol), Pd(dppf)Cl2 (0.73 g, 1.00 mmol), K2CO3 (27.64 g, 200 mmol), and 1000 mL of toluene / ethanol / water (2:1:1) were added sequentially to a reaction flask. The mixture was stirred at 60 °C for 6 hours. After the reaction was completed, the mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from the obtained solid with ethyl acetate to give intermediate A-6 (22.89 g, yield 82%), with an HPLC purity ≥99.86%. Mass spectrometry m / z: 277.9738 (theoretical value: 277.9724).

[0345] Preparation of intermediate B-6: Under nitrogen protection, A-6 (19.54 g, 70 mmol), pinacol diboronate (35.55 g, 140 mmol), and K2CO3 (29.02 g, 210 mmol) were added to a reaction flask, followed by 788 mL of LDM. After purging the air with nitrogen three times, Pd(PPh3)4 (1.04 g, 0.90 mmol) was added. The mixture was heated and stirred for 6.0 h. After the reaction was completed, the reactants were cooled to room temperature, and distilled water was added. The mixture was extracted with dichloromethane, separated, and the organic phase was washed three times with distilled water and dried with anhydrous magnesium sulfate. The obtained solid was purified by recrystallization from toluene:ethanol = 20:5 (v / v) to obtain intermediate B-6 (25.56 g, yield 79%), with an HPLC purity of ≥99.89% and a mass spectrometry m / z of 462.2224 (theoretical value: 462.2207).

[0346] Preparation of Compound 6: Under nitrogen protection, B-6 (13.87 g, 30.00 mmol), c-6 (16.06 g, 60.00 mmol), Pd(dppf)Cl2 (0.33 g, 0.45 mmol), K2CO3 (12.44 g, 90.00 mmol), and 675 mL of toluene / ethanol / water (2:1:1) were added sequentially to a reaction flask. The reaction mixture was stirred at 100 °C for 5.5 hours. After the reaction was completed, the mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from the solid with ethyl acetate to give Compound 6 (14.94 g, yield 74%), with an HPLC purity ≥99.98%. Mass spectrometry m / z: 672.2080 (theoretical value: 672.2096). Theoretical elemental content (%): C 44 H 28 N6S: C, 78.55; H, 4.19; N, 12.49. Measured elemental composition: C, 78.54; H, 4.16; N, 12.47.

[0347] [Synthetic Example 4] Preparation of Compound 11:

[0348] Preparation of Compound 11: Following the same preparation method as in Synthesis Example 3, a-6 was replaced with an equimolar amount of a-11, and b-6 was replaced with an equimolar amount of b-11, yielding Compound 11 (14.73 g) with an HPLC purity ≥99.99%. Mass spectrometry m / z: 672.2084 (theoretical value: 672.2096). Theoretical elemental content (%): C 44 H 28 N6S: C, 78.55; H, 4.19; N, 12.49. Measured elemental content (%): C, 78.56; H, 4.23; N, 12.48.

[0349] [Synthetic Example 5] Preparation of Compound 15:

[0350] Preparation of Compound 15: Following the same preparation method as in Synthesis Example 3, a-6 was replaced with an equimolar amount of a-15, and b-6 was replaced with an equimolar amount of b-15, yielding Compound 15 (14.13 g) with an HPLC purity ≥99.96%. Mass spectrometry m / z: 672.2083 (theoretical value: 672.2096). Theoretical elemental content (%): C 44 H 28 N6S: C, 78.55; H, 4.19; N, 12.49. Measured elemental content (%): C, 78.58; H, 4.17; N, 12.50.

[0351] [Synthetic Example 6] Preparation of Compound 19:

[0352] Preparation of Compound 19: Following the same preparation method as in Synthesis Example 3, a-6 was replaced with an equimolar amount of a-19, and b-6 was replaced with an equimolar amount of b-11, yielding Compound 19 (14.73 g) with an HPLC purity ≥99.94%. Mass spectrometry m / z: 672.2081 (theoretical value: 672.2096). Theoretical elemental content (%): C 44 H 28 N6S: C, 78.55; H, 4.19; N, 12.49. Measured elemental content (%): C, 78.56; H, 4.16; N, 12.48.

[0353] [Synthetic Example 7] Preparation of Compound 31:

[0354] Preparation of compound 31: Following the same preparation method as in Synthesis Example 3, a-6 was replaced with an equimolar amount of a-31 to obtain compound 31 (15.50 g), with an HPLC purity ≥99.92%. Mass spectrometry m / z: 748.2420 (theoretical value: 748.2409). Theoretical elemental content (%): C 50 H 32 N6S: C, 80.19; H, 4.31; N, 11.22. Measured elemental content (%): C, 80.22; H, 4.35; N, 11.23.

[0355] [Synthetic Example 8] Preparation of Compound 86:

[0356] Preparation of compound 86: Following the same preparation method as in Synthesis Example 3, a-6 was replaced with an equimolar amount of a”-86, and b-6 was replaced with an equimolar amount of b-11, yielding compound 86 (16.06 g) with an HPLC purity ≥99.91%. Mass spectrometry m / z: 798.2556 (theoretical value: 798.2566). Theoretical elemental content (%): C 54 H 34 N6S: C, 81.18; H, 4.29; N, 10.52. Measured elemental content (%): C, 81.22; H, 4.27; N, 10.56.

[0357] [Synthetic Example 9] Preparation of Compound 115:

[0358] Preparation of compound 115: Following the same preparation method as in Synthesis Example 3, a-6 was replaced with an equimolar amount of a”-115 to obtain compound 115 (16.36 g), with HPLC purity ≥99.93%. Mass spectrometry m / z: 838.2530 (theoretical value: 838.2515). Theoretical elemental content (%): C 56 H 34 N6OS: C, 80.17; H, 4.08; N, 10.02. Measured elemental content (%): C, 80.19; H, 4.05; N, 10.08.

[0359] [Synthetic Example 10] Preparation of Compound 133:

[0360] Preparation of compound 133: Following the same preparation method as in Synthesis Example 3, a-6 was replaced with an equimolar amount of a”-133, and b-6 was replaced with an equimolar amount of b-11, yielding compound 133 (19.33 g) with an HPLC purity ≥99.98%. Mass spectrometry m / z: 990.3521 (theoretical value: 990.3505). Theoretical elemental content (%): C 69 H 46 N6S: C, 83.61; H, 4.68; N, 8.48. Measured elemental content (%): C, 83.55; H, 4.75; N, 8.49.

[0361] [Synthetic Example 11] Preparation of Compound 137:

[0362] Preparation of compound 137: Following the same preparation method as in Synthesis Example 3, a-6 was replaced with an equimolar amount of a”-137 to obtain compound 137 (19.29 g), with HPLC purity ≥99.96%. Mass spectrometry m / z: 988.3356 (theoretical value: 988.3348). Theoretical elemental content (%): C 69 H 44 N6S: C, 83.78; H, 4.48; N, 8.50. Measured elemental content (%): C, 83.75; H, 4.53; N, 8.54.

[0363] [Synthetic Example 12] Preparation of Compound 146:

[0364] Preparation of intermediate A-146: Under nitrogen protection, a-19 (31.22 g, 120.00 mmol), b-146 (38.08 g, 120.00 mmol), Pd(dppf)Cl2 (0.88 g, 1.20 mmol), K2CO3 (33.17 g, 240.00 mmol), and 1200 mL of toluene / ethanol / water (2:1:1) were added sequentially to a reaction flask. The mixture was stirred at 60 °C for 6 hours. After the reaction was complete, the mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from the obtained solid with ethyl acetate to give intermediate A-146 (33.40 g, yield 86%), with an HPLC purity ≥99.85%. Mass spectrometry m / z: 321.9230 (theoretical value: 321.9219).

[0365] Preparation of intermediate B-146: Under nitrogen protection, A-146 (29.13 g, 90.00 mmol), pinacol diboronate (22.85 g, 90.00 mmol), and K2CO3 (24.88 g, 180 mmol) were added to a reaction flask, followed by the addition of 675 mL of LDMF. After purging the air with nitrogen three times, Pd(PPh3)4 (1.04 g, 0.90 mmol) was added, and the mixture was heated and stirred. After 6.0 h of reaction, the reactants were cooled to room temperature, distilled water was added, and the mixture was extracted with dichloromethane. The mixture was separated, and the organic phase was washed three times with distilled water and dried with anhydrous magnesium sulfate. The solid obtained was purified by recrystallization from toluene:ethanol = 20:5 (v / v) to give intermediate B-146 (27.69 g, yield 83%), HPLC purity ≥ 99.87%, mass spectrometry m / z: 370.0953 (theoretical value: 370.0966).

[0366] Preparation of intermediate C-146: Under nitrogen protection, B-146 (25.95 g, 70.00 mmol), c-6 (18.74 g, 70.00 mmol), Pd(dppf)Cl2 (0.51 g, 0.70 mmol), K2CO3 (19.35 g, 140.00 mmol), and 1050 mL of toluene / ethanol / water (2:1:1) were added sequentially to a reaction flask. The reaction mixture was stirred at 100 °C for 5.5 hours. After the reaction was completed, the mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from the solid with ethyl acetate to give compound C-146 (27.32 g, yield 82%), with an HPLC purity ≥99.89%. Mass spectrometry m / z: 475.0921 (theoretical value: 475.0910).

[0367] Preparation of intermediate D-146: Under nitrogen protection, C-146 (23.80 g, 50 mmol), pinacol diboronate (12.70 g, 50 mmol), and K2CO3 (13.82 g, 100 mmol) were added to a reaction flask, followed by 375 mL of LDM. After purging the air with nitrogen three times, Pd(PPh3)4 (0.58 g, 0.50 mmol) was added. The mixture was heated and stirred for 6.0 h. After the reaction was completed, the reactants were cooled to room temperature, and distilled water was added. The mixture was extracted with dichloromethane, separated, and the organic phase was washed three times with distilled water and dried with anhydrous magnesium sulfate. The obtained solid was purified by recrystallization from toluene:ethanol = 20:5 (v / v) to obtain intermediate D-146 (22.42 g, yield 79%), with an HPLC purity of ≥99.88% and a mass spectrometry m / z of 567.2166 (theoretical value: 567.2152).

[0368] Preparation of compound 146: Under nitrogen protection, D-146 (17.03 g, 30.00 mmol), d-146 (10.31 g, 30.00 mmol), Pd(dppf)Cl2 (0.22 g, 0.30 mmol), K2CO3 (8.29 g, 60.00 mmol), and 450 mL of toluene / ethanol / water (2:1:1) were added sequentially to a reaction flask. The reaction mixture was stirred at 100 °C for 5.5 hours. After the reaction was completed, the mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from the solid with ethyl acetate to give compound 146 (16.63 g, yield 74%), with an HPLC purity ≥99.99%. Mass spectrometry m / z: 748.2422 (theoretical value: 748.2409). Theoretical elemental content (%): C 50 H 32 N6S: C, 80.19; H, 4.31; N, 11.22. Measured elemental composition: C, 80.20; H, 4.33; N, 11.26.

[0369] [Synthetic Example 13] Preparation of Compound 217:

[0370] Preparation of compound 217: Following the same preparation method as in Synthesis Example 12, a-19 was replaced with an equimolar amount of a-15, b-146 with an equimolar amount of b-217, and d-146 with an equimolar amount of d-217, yielding compound 217 (15.61 g) with an HPLC purity ≥99.97%. Mass spectrometry m / z: 722.2264 (theoretical value: 722.2253). Theoretical elemental content (%): C 48 H 30 N6S: C, 79.76; H, 4.18; N, 11.63. Measured elemental content (%): C, 79.77; H, 4.19; N, 11.65.

[0371] [Synthetic Example 14] Preparation of Compound 267:

[0372] Preparation of compound 267: Following the same preparation method as in Synthesis Example 12, b-146 was replaced with an equimolar amount of b-217, and d-146 was replaced with an equimolar amount of d-267 to obtain compound 267 (19.12 g), with an HPLC purity ≥99.98%. Mass spectrometry m / z: 872.2734 (theoretical value: 872.2722). Theoretical elemental content (%): C 60 H 36N6S: C, 82.55; H, 4.16; N, 9.63. Measured elemental content (%): C, 82.57; H, 4.18; N, 9.65.

[0373] [Synthetic Example 15] Preparation of Compound 277:

[0374] Preparation of compound 277: Following the same preparation method as in Synthesis Example 12, a-19 was replaced with an equimolar amount of a-31, and d-146 was replaced with an equimolar amount of d-277, yielding compound 277 (16.66 g) with an HPLC purity ≥99.95%. Mass spectrometry m / z: 804.2143 (theoretical value: 804.2130). Theoretical elemental content (%): C 52 H 32 N6S2: C, 77.59; H, 4.01; N, 10.44. Measured elemental content (%): C, 77.60; H, 4.03; N, 10.41.

[0375] [Synthetic Example 16] Preparation of Compound 290:

[0376] Preparation of compound 290: Following the same preparation method as in Synthesis Example 12, a-19 was replaced with an equimolar amount of a-6, and d-146 was replaced with an equimolar amount of d-290, yielding compound 290 (15.40 g) with an HPLC purity ≥99.92%. Mass spectrometry m / z: 789.2327 (theoretical value: 789.2311). Theoretical elemental content (%): C 51 H 31 N7OS: C, 77.55; H, 3.96; N, 12.41. Measured elemental content (%): C, 77.50; H, 3.97; N, 12.43.

[0377] [Synthetic Example 17] Preparation of Compound 295:

[0378] Preparation of compound 295: Following the same preparation method as in Synthesis Example 12, a-19 was replaced with an equimolar amount of a-11, and d-146 was replaced with an equimolar amount of d-295, yielding compound 295 (16.44 g) with an HPLC purity ≥99.93%. Mass spectrometry m / z: 805.2095 (theoretical value: 805.2082). Theoretical elemental content (%): C 51 H 31N7S2: C, 76.00; H, 3.88; N, 12.17. Measured elemental content (%): C, 76.03; H, 3.89; N, 12.15.

[0379] [Synthetic Example 18] Preparation of Compound 301:

[0380] Preparation of compound 301: Following the same preparation method as in Synthesis Example 12, a-19 was replaced with an equimolar amount of a-6, b-146 with an equimolar amount of b-217, and d-146 with an equimolar amount of d-301, yielding compound 301 (15.79 g) with an HPLC purity ≥99.95%. Mass spectrometry m / z: 762.2219 (theoretical value: 762.2202). Theoretical elemental content (%): C 50 H 30 N6OS: C, 78.72; H, 3.96; N, 11.02. Measured elemental content (%): C, 78.69; H, 3.95; N, 11.05.

[0381] [Synthetic Example 19] Preparation of Compound 307:

[0382] Preparation of compound 307: Following the same preparation method as in Synthesis Example 12, a-19 was replaced with an equimolar amount of a”-307, b-146 with an equimolar amount of b-217, and d-146 with an equimolar amount of d-307, yielding compound 307 (17.99 g) with an HPLC purity ≥99.96%. Mass spectrometry m / z: 894.2252 (theoretical value: 894.2236). Theoretical elemental content (%): C 58 H 34 N6OS2: C, 77.83; H, 3.83; N, 9.39. Measured elemental content (%): C, 77.80; H, 3.85; N, 9.40.

[0383] [Synthetic Example 20] Preparation of Compound 316:

[0384] Preparation of compound 316: Following the same preparation method as in Synthesis Example 12, a-19 was replaced with an equimolar amount of a-11, b-146 with an equimolar amount of b-217, and d-146 with an equimolar amount of d-316, yielding compound 316 (16.57 g) with an HPLC purity ≥99.97%. Mass spectrometry m / z: 788.2738 (theoretical value: 788.2722). Theoretical elemental content (%): C 53 H 36 N6S: C, 80.69; H, 4.60; N, 10.65. Measured elemental content (%): C, 80.67; H, 4.57; N, 10.64.

[0385] [Synthetic Example 21] Preparation of Compound 319:

[0386] Preparation of compound 319: Following the same preparation method as in Synthesis Example 12, a-19 was replaced with an equimolar amount of a-6, b-146 with an equimolar amount of b-217, and d-146 with an equimolar amount of d-319, yielding compound 319 (18.63 g) with an HPLC purity ≥99.95%. Mass spectrometry m / z: 912.3050 (theoretical value: 912.3035). Theoretical elemental content (%): C 63 H 40 N6S: C, 82.87; H, 4.42; N, 9.20. Measured elemental content (%): C, 82.89; H, 4.40; N, 9.21.

[0387] [Synthetic Example 22] Preparation of Compound 323:

[0388] Preparation of compound 323: Following the same preparation method as in Synthesis Example 12, b-146 was replaced with an equimolar amount of b-217, and d-146 was replaced with an equimolar amount of d-323, yielding compound 323 (18.59 g) with an HPLC purity ≥99.94%. Mass spectrometry m / z: 910.2867 (theoretical value: 910.2879). Theoretical elemental content (%): C 63 H 38 N6S: C, 83.05; H, 4.20; N, 9.22. Measured elemental content (%): C, 83.07; H, 4.21; N, 9.18.

[0389] [Synthetic Example 23] Preparation of Compound 324:

[0390] Preparation of compound 324: Following the same preparation method as in Synthesis Example 12, a-19 was replaced with an equimolar amount of a-11, b-146 with an equimolar amount of b-217, and d-146 with an equimolar amount of d-324, yielding compound 324 (18.08 g) with an HPLC purity ≥99.96%. Mass spectrometry m / z: 926.2838 (theoretical value: 926.2828). Theoretical elemental content (%): C 63 H 38 N6OS: C, 81.62; H, 4.13; N, 9.07. Measured elemental content (%): C, 81.58; H, 4.14; N, 9.09.

[0391] [Synthetic Example 24] Preparation of Compound 331:

[0392] Preparation of compound 331: Following the same preparation method as in Synthesis Example 3, a-6 was replaced with an equimolar amount of a-331 to obtain compound 331 (13.99 g, HPLC purity ≥99.97%. Mass spectrometry m / z: 656.2340 (theoretical value: 656.2325). Theoretical elemental content (%): C 44 H 28 N6O: C, 80.47; H, 4.30; N, 12.80. Measured elemental content (%): C, 80.48; H, 4.28; N, 12.83.

[0393] [Synthetic Example 25] Preparation of Compound 376:

[0394] Preparation of compound 376: Following the same preparation method as in Synthesis Example 3, a-6 was replaced with an equimolar amount of a-376, and b-6 was replaced with an equimolar amount of b-11, yielding compound 376 (15.39 g) with an HPLC purity ≥99.95%. Mass spectrometry m / z: 732.2656 (theoretical value: 732.2638). Theoretical elemental content (%): C 50 H 32 N6O: C, 81.95; H, 4.40; N, 11.47. Measured elemental content (%): C, 81.90; H, 4.42; N, 11.48.

[0395] [Synthetic Example 26] Preparation of Compound 473:

[0396] Preparation of compound 473: Following the same preparation method as in Synthesis Example 12, a-19 was replaced with an equimolar amount of a-331, and d-146 was replaced with an equimolar amount of d-473, yielding compound 473 (17.23 g) with an HPLC purity ≥99.98%. Mass spectrometry m / z: 808.2965 (theoretical value: 808.2951). Theoretical elemental content (%): C 56 H 36 N6O: C, 83.15; H, 4.49; N, 10.39. Measured elemental content (%): C, 83.19; H, 4.50; N, 10.35.

[0397] [Synthetic Example 27] Preparation of Compound 508:

[0398] Preparation of compound 508: Following the same preparation method as in Synthesis Example 12, a-19 was replaced with an equimolar amount of a-508, b-146 with an equimolar amount of b-508, and d-146 with an equimolar amount of d-508, yielding compound 508 (15.97 g) with an HPLC purity ≥99.96%. Mass spectrometry m / z: 782.2784 (theoretical value: 782.2794). Theoretical elemental content (%): C 54 H 34 N6O: C, 82.84; H, 4.38; N, 10.73. Measured elemental content (%): C, 82.83; H, 4.41; N, 10.69.

[0399] [Synthetic Example 28] Preparation of Compound 539:

[0400] Preparation of compound 539: Following the same preparation method as in Synthesis Example 12, a-19 was replaced with an equimolar amount of a-539, b-146 was replaced with an equimolar amount of b-217, and d-146 was replaced with an equimolar amount of d-301, yielding compound 539 (15.01 g) with an HPLC purity ≥99.94%. Mass spectrometry m / z: 746.2446 (theoretical value: 746.2430). Theoretical elemental content (%): C 50 H 30 N6O2: C, 80.41; H, 4.05; N, 11.25. Measured elemental content (%): C, 80.43; H, 4.07; N, 11.20.

[0401] [Synthetic Example 29] Preparation of Compound 543:

[0402] Preparation of compound 543: Following the same preparation method as in Synthesis Example 12, a-19 was replaced with an equimolar amount of a-11, b-146 with an equimolar amount of b-508, and d-146 with an equimolar amount of d-543, yielding compound 543 (13.91 g) with an HPLC purity ≥99.97%. Mass spectrometry m / z: 671.2158 (theoretical value: 671.2144). Theoretical elemental content (%): C 45 H 29 N5S: C, 80.45; H, 4.35; N, 10.42. Measured elemental content (%): C, 80.47; H, 4.37; N, 10.38.

[0403] [Synthetic Example 30] Preparation of Compound 604:

[0404] Preparation of compound 604: Following the same preparation method as in Synthesis Example 3, b-6 was replaced with an equimolar amount of b-11, and c-6 was replaced with an equimolar amount of c-604, yielding compound 604 (14.69 g) with an HPLC purity ≥99.93%. Mass spectrometry m / z: 670.2179 (theoretical value: 670.2191). Theoretical elemental content (%): C 46 H 30 N4S: C, 82.36; H, 4.51; N, 8.35. Measured elemental content (%): C, 82.42; H, 4.54; N, 8.30.

[0405] [Synthetic Example 31] Preparation of Compound 651:

[0406] Preparation of compound 651: Following the same preparation method as in Synthesis Example 3, a-6 was replaced with an equimolar amount of a-19, b-6 with an equimolar amount of b-11, and c-6 with an equimolar amount of c-651, yielding compound 651 (13.85 g) with an HPLC purity ≥99.99%. Mass spectrometry m / z: 668.2298 (theoretical value: 668.2286). Theoretical elemental content (%): C 48 H 32 N₂S: C, 86.20; H, 4.82; N, 4.19. Measured elemental content (%): C, 86.19; H, 4.84; N, 4.23.

[0407] [Synthetic Example 32] Preparation of Compound 664:

[0408] Preparation of compound 664: Following the same preparation method as in Synthesis Example 12, a-19 was replaced with an equimolar amount of a-6, and d-146 was replaced with an equimolar amount of d-664, yielding compound 664 (13.48 g) with an HPLC purity ≥99.94%. Mass spectrometry m / z: 670.2199 (theoretical value: 670.2191). Theoretical elemental content (%): C 46 H 30 N4S: C, 82.36; H, 4.51; N, 8.35. Measured elemental content (%): C, 82.32; H, 4.52; N, 8.41.

[0409] [Synthetic Example 33] Preparation of Compound 725:

[0410] Preparation of compound 725: Following the same preparation method as in Synthesis Example 12, a-19 was replaced with an equimolar amount of a-331, b-146 with an equimolar amount of b-217, and d-146 with an equimolar amount of d-543, yielding compound 725 (13.57 g) with an HPLC purity ≥99.95%. Mass spectrometry m / z: 655.2360 (theoretical value: 655.2372). Theoretical elemental content (%): C 45 H 29 N5O: C, 82.42; H, 4.46; N, 10.68. Measured elemental content (%): C, 82.40; H, 4.51; N, 10.69.

[0411] [Synthetic Example 34] Preparation of Compound 768:

[0412] Preparation of compound 768: Following the same preparation method as in Synthesis Example 3, a-6 was replaced with an equimolar amount of a-768, and b-6 was replaced with an equimolar amount of b-11, yielding compound 768 (15.37 g) with an HPLC purity ≥99.96%. Mass spectrometry m / z: 731.2789 (theoretical value: 731.2797). Theoretical elemental content (%): C 50 H 33 N7: C, 82.06; H, 4.55; N, 13.40. Measured element content (%): C, 82.08; H, 4.51; N, 13.43.

[0413] [Synthetic Example 35] Preparation of Compound 802:

[0414] Preparation of compound 802: Following the same preparation method as in Synthesis Example 3, a-6 was replaced with an equimolar amount of a-802 to obtain compound 802 (13.93 g), with an HPLC purity ≥99.92%. Mass spectrometry m / z: 682.2860 (theoretical value: 682.2845). Theoretical elemental content (%): C 47 H 34 N6: C, 82.67; H, 5.02; N, 12.31. Measured elemental content (%): C, 82.70; H, 5.06; N, 12.35.

[0415] [Synthetic Example 36] Preparation of Compound 837:

[0416] Preparation of compound 837: Following the same preparation method as in Synthesis Example 3, a-6 was replaced with an equimolar amount of a-837 to obtain compound 837 (15.61 g), with an HPLC purity ≥99.93%. Mass spectrometry m / z: 722.2266 (theoretical value: 722.2253). Theoretical elemental content (%): C 48 H 30 N6S: C, 79.76; H, 4.18; N, 11.63. Measured elemental content (%): C, 79.72; H, 4.16; N, 11.60.

[0417] [Synthetic Example 37] Preparation of Compound 889:

[0418] Preparation of compound 889: Following the same preparation method as in Synthesis Example 3, a-6 was replaced with an equimolar amount of a”-889, and b-6 was replaced with an equimolar amount of b-11, yielding compound 889 (13.95 g) with an HPLC purity ≥99.97%. Mass spectrometry m / z: 673.2062 (theoretical value: 673.2049). Theoretical elemental content (%): C 43 H 27 N7S: C, 76.65; H, 4.04; N, 14.55. Measured elemental content (%): C, 76.60; H, 4.03; N, 14.57.

[0419] [Synthetic Example 38] Preparation of Compound 928:

[0420] Preparation of compound 928: Following the same preparation method as in Synthesis Example 12, a-19 was replaced with an equimolar amount of a”-928, and d-146 was replaced with an equimolar amount of d-928, yielding compound 928 (18.81 g) with an HPLC purity ≥99.95%. Mass spectrometry m / z: 882.2361 (theoretical value: 882.2348). Theoretical elemental content (%): C 56 H 34 N8S2: C, 76.17; H, 3.88; N, 12.69. Measured elemental content (%): C, 76.20; H, 3.84; N, 12.73.

[0421] [Synthetic Example 39] Preparation of Compound 945:

[0422] Preparation of compound 945: Following the same preparation method as in Synthesis Example 12, a-19 was replaced with an equimolar amount of a-6, b-146 with an equimolar amount of b-217, and d-146 with an equimolar amount of d-945, yielding compound 945 (15.05 g) with an HPLC purity ≥99.95%. Mass spectrometry m / z: 677.2427 (theoretical value: 677.2410). Theoretical elemental content (%): C 44 H 23 D5N6S: C, 77.97; H, 4.91; N, 12.40. Measured elemental content (%): C, 77.95; H, 4.94; N, 12.37.

[0423] [Synthetic Example 40] Preparation of Compound 954:

[0424] Preparation of compound 954: Following the same preparation method as in Synthesis Example 3, a-6 was replaced with an equimolar amount of a”-954 to obtain compound 954 (14.43 g), with an HPLC purity ≥99.97%. Mass spectrometry m / z: 728.2738 (theoretical value: 728.2722). Theoretical elemental content (%): C 48 H 36 N6S: C, 79.09; H, 4.98; N, 11.53. Measured elemental content (%): C, 79.12; H, 4.94; N, 11.57.

[0425] [Synthetic Example 41] Preparation of Compound 957:

[0426] Preparation of compound 957: Following the same preparation method as in Synthesis Example 3, a-6 was replaced with an equimolar amount of a-19, b-6 with an equimolar amount of b-11, and c-6 with an equimolar amount of c-957, yielding compound 957 (16.01 g) with an HPLC purity ≥99.99%. Mass spectrometry m / z: 784.3357 (theoretical value: 784.3348). Theoretical elemental content (%): C 52 H 44 N6S: C, 79.56; H, 5.65; N, 10.71. Measured elemental content (%): C, 79.53; H, 5.62; N, 10.66.

[0427] [Synthetic Example 42] Preparation of Compound 970:

[0428] Preparation of compound 970: Following the same preparation method as in Synthesis Example 12, a-19 was replaced with an equimolar amount of a-11, b-146 with an equimolar amount of b-217, and d-146 with an equimolar amount of d-970, yielding compound 970 (16.48 g) with an HPLC purity ≥99.95%. Mass spectrometry m / z: 762.1639 (theoretical value: 762.1625). Theoretical elemental content (%): C 44 H 23 F5N6S: C, 69.29; H, 3.04; N, 11.02. Measured elemental content (%): C, 69.34; H, 3.00; N, 11.06.

[0429] [Synthetic Example 43] Preparation of Compound 971:

[0430] Preparation of compound 972: Following the same preparation method as in Synthesis Example 12, d-146 was replaced with an equimolar amount of d-972 to obtain compound 972 (15.87 g), with an HPLC purity ≥99.93%. Mass spectrometry m / z: 744.2479 (theoretical value: 744.2491). Theoretical elemental content (%): C 47 H 36 N6SSi: C, 75.77; H, 4.87; N, 11.28. Measured elemental content (%): C, 75.78; H, 4.82; N, 11.30.

[0431] [Synthetic Example 44] Preparation of Compound 979:

[0432] Preparation of compound 979: Following the same preparation method as in Synthesis Example 12, a-19 was replaced with an equimolar amount of a-6, and d-146 was replaced with an equimolar amount of d-979, yielding compound 979 (16.48 g) with an HPLC purity ≥99.98%. Mass spectrometry m / z: 773.2374 (theoretical value: 773.2362). Theoretical elemental content (%): C 51 H 31 N7S: C, 79.15; H, 4.04; N, 12.67. Measured elemental content (%): C, 79.19; H, 4.07; N, 12.61.

[0433] [Synthetic Example 45] Preparation of Compound 994:

[0434] Preparation of compound 994: Following the same preparation method as in Synthesis Example 3, a-6 was replaced with an equimolar amount of a”-994 to obtain compound 994 (15.05 g), with an HPLC purity ≥99.96%. Mass spectrometry m / z: 748.2428 (theoretical value: 748.2409). Theoretical elemental content (%): C 50 H 32 N6S: C, 80.19; H, 4.31; N, 11.22. Measured elemental content (%): C, 80.14; H, 4.35; N, 11.20.

[0435] [Synthetic Example 46] Preparation of Compound 1003:

[0436] Preparation of compound 1003: Following the same preparation method as in Synthesis Example 3, a-6 was replaced with an equimolar amount of a-1003, and b-6 was replaced with an equimolar amount of b-15, yielding compound 1003 (17.45 g) with an HPLC purity ≥99.97%. Mass spectrometry m / z: 880.2457 (theoretical value: 880.2443). Theoretical elemental content (%): C 58 H 36 N6S2: C, 79.07; H, 4.12; N, 9.54. Measured elemental content (%): C, 79.11; H, 4.15; N, 9.51.

[0437] Device Examples

[0438] Test methods: Driving voltage and luminous efficiency were tested using a combined IVL testing system consisting of testing software, a computer, a Keithley K2400 digital source meter, and a Photo Research PR788 spectral scanning luminance meter. Lifetime was tested using a McScience M6000 OLED lifetime testing system. The testing environment was atmospheric, at room temperature; test conditions: voltage and efficiency were tested at an applied voltage of 10 mA / cm². 2 The value is determined by the current density; T95 refers to a value at 10 mA / cm². 2 The time (h) at which the initial brightness drops to 95% under the current density.

[0439] The materials used in fabricating the organic electroluminescent device and the contrast device are shown below:

[0440]

[0441] Device Example 1: Fabrication of a Blue Organic Electroluminescent Device

[0442] The ITO / Ag / ITO transparent glass substrate was ultrasonically cleaned twice with a 5% glass cleaning solution for 20 minutes each time, followed by ultrasonic cleaning twice with deionized water for 10 minutes each time. Then, it was ultrasonically cleaned sequentially with acetone and isoacetone for 20 minutes each, and dried at 120°C. All organic materials were sublimated and had a purity of over 99.99%. A 10 nm thick HI-1 layer is vacuum-deposited on an ITO / Ag / ITO transparent glass substrate as a hole injection layer. A 120 nm thick HT-1 layer is vacuum-deposited on the hole injection layer as a hole transport layer. A mixture of BH-1 and BD-1 (BH-1:BD-1 mass ratio = 99:1) is deposited on the hole transport layer to form a light-emitting layer with a deposition thickness of 20 nm. Then, a mixture of compound 6 of the present invention and LiQ (compound 6:LiQ mass ratio = 1:1) is vacuum-deposited on the light-emitting layer as an electron transport layer with a deposition thickness of 30 nm. Then, a 1 nm thick LiF layer is deposited as an electron injection layer. A 13 nm thick Mg:Ag (Mg:Ag mass ratio = 1:9) layer is vacuum-deposited on the electron injection layer as a cathode with a deposition thickness of 13 nm. Finally, a 73 nm thick CP-1 layer is deposited on the cathode as a capping layer to prepare an organic electroluminescent device.

[0443] Device Examples 2-44: Fabrication of Blue Organic Electroluminescent Devices

[0444] Organic electroluminescent devices were prepared by replacing compound 11 in device example 1 with compounds from Table 1 as the electron transport layer material, while keeping the rest of the fabrication process exactly the same.

[0445] Comparative Examples 1-2: Organic electroluminescent devices were prepared by replacing compound 6 in device example 1 with comparative compounds-1 and-2 from Table 1 as electron transport layer materials, while keeping the rest of the fabrication process exactly the same.

[0446] Table 1: Test data on the luminescence characteristics of the organic electroluminescent devices prepared in Device Examples 1-44 and Comparative Examples 1-2

[0447]

[0448] As shown in Table 1, the heterocyclic compound provided by the present invention has good electron mobility. When used as an electron transport layer material for organic electroluminescent devices, the device exhibits high luminous efficiency, low driving voltage, and long lifetime.

[0449] The materials used in fabricating the organic electroluminescent device and the contrast device are shown below:

[0450]

[0451] Device Example 45: Fabrication of Green Organic Electroluminescent Devices

[0452] The ITO / Ag / ITO transparent glass substrate was ultrasonically cleaned twice with a 5% glass cleaning solution for 20 minutes each time, followed by ultrasonic cleaning twice with deionized water for 10 minutes each time. It was then ultrasonically cleaned sequentially with acetone and isoacetone for 20 minutes each time, and dried at 120°C. All organic materials were sublimated and had a purity of over 99.99%. A 10nm thick mixture of HI-2 and HT-2 (HI-2:HT-2 mass ratio = 3:97) was vacuum-deposited onto the ITO / Ag / ITO transparent glass substrate as a hole injection layer. A 120nm thick HT-2 layer was then vacuum-deposited onto the hole injection layer as a hole transport layer. A 20nm thick mixture of GH-1, GH-2, and GD-1 (GH-1:GH-2:GD-1 mass ratio = 46:46:8) was then deposited onto the hole transport layer to form the light-emitting layer. Compound 6 of the present invention, with a thickness of 35 nm, is vacuum-deposited as a hole-blocking layer. Then, a mixture of ET-1 and LiQ (ET-1:LiQ mass ratio = 1:1) is vacuum-deposited on the hole-blocking layer as an electron transport layer with a thickness of 30 nm. Next, LiF with a thickness of 1 nm is vacuum-deposited as an electron injection layer. Mg:Ag (Mg:Ag mass ratio = 1:9) is vacuum-deposited on the electron injection layer as a cathode with a thickness of 13 nm. Finally, CP-1 with a thickness of 73 nm is deposited on the cathode as a capping layer, thereby preparing an organic electroluminescent device.

[0453] Device Examples 46-88: Fabrication of Blue Organic Electroluminescent Devices

[0454] Organic electroluminescent devices were prepared by replacing compound 11 in device example 1 with compounds from Table 1 as the electron transport layer material, while keeping the rest of the fabrication process exactly the same.

[0455] Comparative Examples 3-4: Organic electroluminescent devices were prepared using comparative compounds-3 and-4 from Table 2, and compound 6 from alternative device example 44 as hole blocking layer materials, with the rest of the fabrication process being exactly the same.

[0456] Table 2: Test data on the luminescence characteristics of the organic electroluminescent devices prepared in Device Examples 46-88 and Comparative Examples 3-4

[0457]

[0458] As shown in Table 2, the heterocyclic compound provided by the present invention has suitable energy levels. When used as a hole blocking layer material for organic electroluminescent devices, the device exhibits high luminous efficiency, low driving voltage, and long lifetime.

[0459] 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 heterocyclic compound, characterized in that, The heterocyclic compound has the structure shown in Formula 1: The X atoms may be the same or different from each other, are selected from C(R1) or N atoms, and have at least one N atom. When X is bonded to other groups, X is selected from C. The R1 is independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic group, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaromatic ring, or two adjacent R1s bonded together to form a substituted or unsubstituted ring; The Y atoms may be the same or different from each other, are selected from C(R2) or N atoms, and have at least one N atom. When Y is bonded to other groups, Y is selected from C. The R2 is independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic group, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaromatic ring, or two adjacent R2s bonded together to form a substituted or unsubstituted ring; The P is selected from the structure shown in formula 1-a. "This refers to the connection points with X, Y, and L; The Q atoms may be the same or different from each other, and are selected from C(R3) or N atoms; The R3 is independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic group, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaromatic ring, or two adjacent R3s bonded together to form a substituted or unsubstituted ring; The Ar is selected from the structure shown in Formula 1-1; The z atoms may be the same or different from each other, and are selected from C(R4) or N atoms. When z is bonded to other groups, the z atoms are selected from C. The E is selected from O, S, C(R5)(R6) or N(R7); The R4, R5, and R6 are independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic group, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaromatic ring, or two adjacent R4 are bonded to form a substituted or unsubstituted ring, or two adjacent R5 and R6 are bonded to form a substituted or unsubstituted ring; The R7 is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic group, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, and fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaromatic ring; The R is independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic group, fused cycloyl group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, and fused cycloyl group of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaromatic ring; The n is selected from 0, 1, or 2; The L, L1, L2, L3, and L4 are independently selected from any one of the following: single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C3-C30 heteroarylene, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic rings, and substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaromatic rings. Ar1, Ar2, Ar3, and Ar4 are independently selected from any one of the following: substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 heteroaryl groups, substituted or unsubstituted C3-C20 alicyclic groups, fused cyclic groups of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic groups, and fused cyclic groups of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaromatic groups.

2. The heterocyclic compound according to claim 1, characterized in that, Equation 1 is selected from any of the following structures: The limitations of P, Ar, Ar1, Ar2, Ar3, Ar4, L, L1, L2, L3, L4, R1, and R2 are the same as those in Formula 1; t1 is selected from 0 or 1; t2 is selected from 0, 1 or 2; The q1 is selected from 0 or 1; the q2 is selected from 0, 1 or 2.

3. The heterocyclic compound according to claim 1, characterized in that, The P is selected from any of the following structures: " "This refers to the connection points with X, Y, and L; The R3 mentioned is the same as the limitation in Equation 1.

4. The heterocyclic compound according to claim 1, characterized in that, The Choose any one of the following structures: The R4, R5, and R6 are independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic group, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaromatic ring, or two adjacent R4 are bonded to form a substituted or unsubstituted ring, or two adjacent R5 and R6 are bonded to form a substituted or unsubstituted ring; The R7 is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic group, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, and fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaromatic ring; The R is independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic group, fused cycloyl group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, and fused cycloyl group of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaromatic ring; The n is selected from 0, 1, or 2; the n1 is selected from 0 or 1; The m1 is selected from 0, 1, 2, 3 or 4; the m2 is selected from 0, 1, 2 or 3; the m3 is selected from 0, 1 or 2; the m4 is selected from 0 or 1; the m5 is selected from 0, 1, 2, 3, 4, 5 or 6; the m6 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the m7 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.

5. The heterocyclic compound according to claim 1, characterized in that, Ar1, Ar2, Ar3, and Ar4, whether identical or different, are selected from any of the following structures: The v may be the same as or different from each other, and are selected from C (R8) or N atoms. When v is bonded to other groups, the v is selected from C. The t atoms may be the same or different from each other, and are selected from C (Ra) or N atoms. When t is bonded to other groups, the t atoms are selected from C. The ring A is independently selected from substituted or unsubstituted C3-C20 alicyclic groups; The Gs may be the same or different from each other, and are selected from any one of O, S, C(R1′)(R2′) or N(R3′); The R8 is independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic group, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaromatic ring, or two adjacent R8s bonded together to form a substituted or unsubstituted ring; The Ra is independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic group, fused cycloyl group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, and fused cycloyl group of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaromatic ring; The R1′ and R2′ are independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic group, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaromatic ring, or two adjacent R1′ and R2′ are bonded to form a substituted or unsubstituted ring; The R3′ is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic group, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic rings, and fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaromatic rings.

6. The heterocyclic compound according to claim 1, characterized in that, Ar1, Ar2, Ar3, and Ar4, whether identical or different, are selected from any of the following structures: The R8 is independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic group, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaromatic ring, or two adjacent R8s bonded together to form a substituted or unsubstituted ring; The Ra is independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic group, fused cycloyl group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, and fused cycloyl group of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaromatic ring; The R1′ and R2′ are independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic group, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaromatic ring, or two adjacent R1′ and R2′ are bonded to form a substituted or unsubstituted ring; The R3′ is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic group, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, and fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaromatic ring; a1 is selected from 0, 1, 2, 3, 4, or 5; a2 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; a3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; a4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; a5 is selected from 0, 1, 2, 3, or 4; a6 is selected from 0, 1, 2, or 3; a7 is selected from 0, 1, 2, 3, 4, 5, or 6; a8 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; a9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; a 10 Selected from 0, 1, or 2; the a 11 Choose from 0 or 1.

7. The heterocyclic compound according to claim 1, characterized in that, The L, L1, L2, L3, and L4 that are the same or different are selected from single bonds or any of the following structures: The W is selected from O, S, or N(R6′); The R9 is independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic group, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaromatic ring, or two adjacent R9s bonded together to form a substituted or unsubstituted ring; The Rb is independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic group, fused cycloyl group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, and fused cycloyl group of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaromatic ring; The R4′ and R5′ are independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic group, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaromatic ring, or two adjacent R4′ and R5′ are bonded to form a substituted or unsubstituted ring; The R6′ is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic group, fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, and fused cyclic group of substituted or unsubstituted C3-C20 alicyclic and C3-C30 heteroaromatic ring; The number b1 is selected from 0, 1, 2, 3, or 4; the number b2 is selected from 0, 1, 2, 3, 4, 5, or 6; the number b3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the number b4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; the number b5 is selected from 0, 1, 2, or 3; the number b6 is selected from 0, 1, or 2; the number b7 is selected from 0 or 1; the number b8 is selected from 0, 1, 2, 3, 4, or 5; and the number b9 is selected from 0, 1, 2, 3, 4, 5, 6, or 7.

8. The heterocyclic compound according to claim 1, characterized in that, Equation 1 is selected from one of the following structures: 。 9. An organic electroluminescent device, comprising an anode, a cathode, and an organic layer disposed between the anode and the cathode, characterized in that, The organic layer comprises at least one of the heterocyclic compounds according to any one of claims 1 to 8.

10. The organic electroluminescent device according to claim 9, characterized in that, The organic layer comprises at least one of an electron transport layer, a hole blocking layer, and a charge generation layer, wherein at least one of the electron transport layer, hole blocking layer, and charge generation layer comprises at least one of the heterocyclic compounds according to any one of claims 1 to 8.

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