Heterocyclic compound and organic electroluminescent device thereof

Abstract

This invention relates to a heterocyclic compound and its organic electroluminescent device. The heterocyclic compound possesses suitable energy levels and excellent electron transport properties. As an electron transport material, it can increase electron migration rate, reduce carrier transport imbalance, increase the recombination probability of holes and electrons within the luminescent layer, enhance device luminous efficiency, and extend lifespan. As a hole-blocking material, it can lower the energy level barrier, promote electron injection, and effectively block hole diffusion, confining exciton recombination within the luminescent layer, further improving device luminous efficiency and lifespan. As a host material, it possesses a high triplet energy level, providing an energy transfer channel for guest luminescent materials, suppressing aggregation quenching phenomena, adjusting the uniformity of luminous color, and ensuring the stability and consistency of device luminescence.

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 devices (OLEDs), also known as organic light-emitting diodes, have advantages such as self-illumination, no need for backlighting, wide viewing angle, fast response speed, vivid colors, thinness and flexibility, wide operating temperature range, high definition, strong flexibility, and low energy consumption. They have become one of the core technologies in the display and lighting fields, attracting widespread attention and in-depth research worldwide. They are gradually replacing traditional display and lighting technologies and driving the upgrading and iteration of related industries.

[0003] Organic electroluminescent devices employ a classic "sandwich" layered structure, primarily composed of functional layers such as an anode, cathode, hole injection layer, hole transport layer, hole blocking layer, luminescent layer, electron blocking layer, electron transport layer, electron injection layer, and capping layer. Their light-emitting mechanism can be summarized as follows: Under an applied electric field, holes and electrons are injected into the device from the anode and cathode, respectively. They migrate to the luminescent layer, meet, and recombine to form excitons. These excitons transfer energy to organic molecules in the luminescent layer, causing them to transition from the ground state to an unstable excited state. During the return process to the ground state, the excited molecules undergo radiative transitions, releasing energy in the form of light, thus achieving electroluminescence.

[0004] In organic light-emitting diodes (OLEDs), the performance of each organic functional layer directly affects key indicators such as luminous efficiency, lifetime, color purity, and driving voltage. However, currently widely used electron transport materials often have low electron mobility, and some hole-blocking materials suffer from insufficient thermal stability, poor film formation, and poor compatibility with adjacent layers. This not only easily introduces interface defects but also makes it difficult to effectively control the energy level barrier, leading to hole leakage into the electron transport layer. At the same time, some host materials suffer from carrier transport imbalance and insufficient energy level matching. These problems collectively restrict the luminous efficiency and lifetime of OLEDs.

[0005] Therefore, to address the performance shortcomings of existing functional layers and the overall optoelectronic requirements of devices, there is an urgent need to develop next-generation organic functional materials. Ideal electron transport materials, hole blocking materials, and host materials should possess high carrier mobility, appropriate energy level matching, good thermal and chemical stability, and excellent film-forming properties. Through material-level optimization, it is hoped that the luminous efficiency of OLEDs can be further improved, their lifespan extended, and the driving voltage reduced. Summary of the Invention

[0006] To address the aforementioned problems, this invention provides a heterocyclic compound and applies it to organic electroluminescent devices. This heterocyclic compound can reduce the driving voltage of organic electroluminescent devices, increase electron mobility, and improve the luminous efficiency and lifetime of organic electroluminescent devices.

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

[0008] In Equation 1, the X values ​​are the same or different from each other, and each is independently selected from C or N, wherein there are exactly three X values ​​selected as N; The V values ​​may be the same as or different from each other, and each is independently selected from CH or N; R1 is independently selected from any one of the following: substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C6-C30 aromatic ring and C3-C12 alicyclic ring, and fused cycloalcoholic group of substituted or unsubstituted C2-C30 heteroaryl ring and C3-C12 alicyclic ring; The R2 is independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C6-C30 aromatic ring and C3-C12 alicyclic ring, fused cycloalcoholic group of substituted or unsubstituted C2-C30 heteroaryl ring and C3-C12 alicyclic ring, or adjacent R2 can be interconnected to form a substituted or unsubstituted ring; The n is independently selected from 0, 1, 2, 3 or 4; The M is selected from the following groups:

[0009] The " "This is the connection site with L, L3, or L0; The R3 is independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C6-C30 aromatic ring and C3-C12 alicyclic ring, fused cycloalcoholic group of substituted or unsubstituted C2-C30 heteroaryl ring and C3-C12 alicyclic ring, or adjacent R3s can be interconnected to form substituted or unsubstituted rings; The m is independently selected from 0, 1, 2, or 3; The Ar, Ar1, and Ar2 may be the same as or different from each other, and each is independently selected from any one of the following: substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, fused cyclic groups of substituted or unsubstituted C6-C30 aromatic rings and C3-C12 alicyclic rings, and fused cyclic groups of substituted or unsubstituted C2-C30 heteroaryl rings and C3-C12 alicyclic rings; the substituted groups in "substituted or unsubstituted" of Ar, Ar1, and Ar2 are selected from deuterium, cyano, ... Halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C6-C30 aromatic ring and C3-C12 alicyclic ring, fused cycloalcoholic group of substituted or unsubstituted C2-C30 heteroaryl ring and C3-C12 alicyclic ring, or adjacent substituents may be interconnected to form substituted or unsubstituted rings; The L is independently selected from any one or a combination of substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups; The L0, L1, L2, and L3 may be the same as or different from each other, and are independently selected from any one or a combination of single-bonded, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene. The condition is that the compound of formula 1 does not contain the following structure. .

[0010] The present invention also provides an organic electroluminescent device, wherein the organic electroluminescent device comprises any one or more of the heterocyclic compounds described in the present invention.

[0011] Beneficial effects: The heterocyclic compounds provided by this invention possess suitable energy levels and excellent electron transport properties. When used as electron transport materials, they can increase the electron migration rate in devices, reduce the exciton recombination region shift caused by carrier transport imbalance, thereby increasing the recombination probability of holes and electrons within the emissive layer, enhancing device luminescence efficiency, and extending lifespan. When used as hole-blocking materials, they can lower the energy level barrier, promote electron injection into the emissive layer, and effectively block hole diffusion into the electron transport layer, confining the exciton recombination process within the emissive layer, further improving device luminescence efficiency and lifespan. When used as host materials, they possess high triplet energy levels, providing energy transfer channels for doped guest luminescent materials, suppressing aggregation and quenching phenomena between guest molecules, and regulating the uniformity of the emitted color, thus ensuring the stability and consistency of device luminescence, ultimately achieving high-efficiency luminescence in organic electroluminescent devices. Detailed Implementation

[0012] The present invention will be further illustrated below with reference to specific embodiments. It should be understood that these embodiments are for illustrative purposes only and are not intended to limit the scope of the invention. After reading the present invention, any modifications of the present invention in various equivalent forms by those skilled in the art will fall within the scope of protection claimed in this application.

[0013] In the compounds of this invention, any atom not specified as a particular isotope includes any stable isotope of that atom, and includes atoms at both their natural and non-natural isotopic abundances.

[0014] Examples of halogen atoms described in this invention may include fluorine, chlorine, bromine, or iodine.

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

[0016] In this invention, 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.

[0017] In this invention, when the bond containing the substituent or linking site extends through two or more rings, it indicates that it 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.

[0018] In this invention, "two adjacent groups connecting to form a ring" refers to the formation of a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle by combining adjacent groups with each other and optionally aromatizing them. The hydrocarbon ring can be an aliphatic or aromatic hydrocarbon ring. The heterocycle can be an aliphatic or aromatic heterocycle. The aliphatic hydrocarbon ring can be a saturated or unsaturated aliphatic hydrocarbon ring, and the aliphatic heterocycle can be a saturated or unsaturated aliphatic heterocycle. The hydrocarbon ring and heterocycle can be monocyclic or polycyclic groups. Furthermore, the ring formed by the combination of adjacent groups can be connected to another ring to form a spirostructure. Specific examples are shown below:

[0019] In this invention, the rings formed by the connection can be three-membered rings, four-membered rings, five-membered rings, six-membered rings, seven-membered rings, eight-membered rings, fused rings, spirocyclic rings, etc., such as cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, adamantane, norbornene, benzene, naphthalene, phenanthrene, triphenylene, pyridine, pyrimidine, quinoline, isoquinoline, quinazoline, quinoxaline, fluorene, dibenzofuran, dibenzothiophene, carbazole, etc., but are not limited to these.

[0020] The term "substitution" as used in this invention refers to the replacement of a hydrogen atom in certain functional groups by another atom or functional group (i.e., a substituent), and the position of substitution is not limited, as long as the position is where the hydrogen atom is substituted. Furthermore, when two or more are substituted, the two or more substituents may be the same as or different from each other.

[0021] The term "substituted or unsubstituted" as used in this invention means either unsubstituted or substituted by one or more substituents selected from the group consisting of: deuterium, halogen, cyano, nitro, trifluoromethyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted silyl, etc., but not limited thereto. The substituents are preferably the following groups: deuterium, halogen, cyano, nitro, trifluoromethyl, methyl, deuterated methyl, ethyl, deuterated ethyl, n-propyl, isopropyl, deuterated isopropyl, n-butyl, isobutyl, tert-butyl, deuterated tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, vinyl, isopropenyl, cyclopentenyl, cyclohexenyl, adamantyl, norbornel, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, anthracene, phenanthrene, pyrene, phenyl, peryl, fluoranyl, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9 -Phenylfluorenyl, spirofluorenyl, carbazole, 9-phenylcarbazole, 9,9'-spirodifluorenyl, pyrroleyl, furanyl, thiopheneyl, benzofuranyl, benzothiopheneyl, pyridofuranyl, pyridothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl, naphthinyl, o-phenanthrolinel, oxazolyl, thiazolyl, benzooxazolyl, benzoxazolyl, benzothiazolyl, pyridothiazolyl, phenthiazolyl, phenoxazinyl, acridineyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentenyl, benzocyclohexenyl, etc., but not limited to these. When a substance is substituted by multiple substituents, the substituents may be the same or different from each other, and two adjacent substituents may be linked together to form a ring.

[0022] The alkyl group described in this invention refers to a monovalent group obtained by removing one hydrogen atom from an alkane molecule. It can be a straight-chain alkyl group or a branched alkyl group. The number of carbon atoms in the alkyl group is preferably 1 to 12, more preferably 1 to 8, and most preferably 1 to 6. The straight-chain alkyl group includes methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, etc., but is not limited thereto. The branched alkyl group includes isopropyl, isobutyl, sec-butyl, tert-butyl, isomers of n-pentyl, isomers of n-hexyl, isomers of n-heptyl, etc., but is not limited thereto.

[0023] The cycloalkyl group described in this invention refers to a monovalent group obtained by removing one hydrogen atom from a cyclic alkane molecule. The cycloalkyl group preferably has 3 to 12 carbon atoms, more preferably 3 to 8, and most preferably 3 to 6. The cycloalkyl group includes monocyclic cycloalkyl, polycyclic cycloalkyl, and bridged cycloalkyl. Examples of cycloalkyl groups include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornene, camphene, fentanyl, isocamphene, etc., but are not limited thereto.

[0024] The silyl group described in this invention refers to a monovalent group formed by removing one hydrogen atom from a silane molecule, and can be represented by the group -Si(Rs)(Rs)(Rs), where Rs is selected from hydrogen, deuterium, cyano, halogen, or any one or more of the alkyl, alkenyl, alkoxy, and cycloalkyl groups mentioned above. Preferably, it has 1 to 30 carbon atoms, particularly preferably 1 to 25 carbon atoms, more preferably 1 to 22 carbon atoms, and most preferably 1 to 18 carbon atoms. Examples may include trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, dimethylethylsilyl, dimethyltert-butylsilyl, diethylmethylsilyl, tricyclopropanesilyl, tricyclobutanesilyl, etc., but are not limited thereto.

[0025] The aryl group described in this invention refers to a monovalent group obtained by removing a hydrogen atom from the aromatic carbon atom of an aromatic compound molecule, and can be a monocyclic aryl, polycyclic aryl, fused-ring aryl, or a combination thereof. The number of carbon atoms in the aryl group is preferably 6 to 30, more preferably 6 to 18, and most preferably 6 to 12. 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, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-adamantyl-fluorenyl, spiro-cyclopentenyl-fluorenyl, spiro-cyclohexenyl-fluorenyl, etc., but not limited to this.

[0026] The heteroaryl group described in this invention refers to a group obtained by substituting at least one aromatic carbon atom in an aryl group with a heteroatom. The heteroatom includes, but is not limited to, oxygen, sulfur, nitrogen, silicon, selenium, boron, and phosphorus atoms. The heteroaryl group preferably has 2 to 30 carbon atoms, more preferably 2 to 18, and most preferably 3 to 12. 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, fused-ring heteroaryl, or a combination thereof. The monocyclic heteroaryl groups include furanyl, thiophene, oxazolyl, thiazolyl, imidazole, pyrrolyl, imidazole, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, etc., but are not limited thereto; the polycyclic heteroaryl groups include bipyridyl, bipyrimidinyl, phenylpyridyl, phenylpyrimidinyl, phenylfuranyl, phenylthiophene, etc., but are not limited thereto; the fused-ring heteroaryl groups include quinolinyl, isoquinolinyl, benzo[a]quinolinyl, benzo[a]isoquinolinyl, quinazolinyl, quinazolinyl, quinoxalyl, benzo[a]quinolinyl, quinazolinyl, quinoxal ... Azolinyl, benzoquinoxalinyl, o-phenanthrolinel, naphthidyl, indolyl, benzothiopheneyl, benzofuranyl, benzooxazolyl, benzoimidazolyl, benzothiazolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothiopheneyl, benzodibenzothiopheneyl, dibenzooxazolyl, dibenzoimidazolyl, dibenzothiazolyl, carbazoleyl, benzocarbazoleyl, acridineyl, phenoxazinyl, phenthiazinyl, phenoxthiayl, spirofluorenexanthraceneyl, spirofluorenethionthanthraceneyl, etc., but not limited to these.

[0027] The fused alicyclic and aromatic ring group described in this invention refers to the monovalent group obtained by removing one hydrogen atom after the alicyclic and aromatic rings are fused together. The aromatic ring preferably has 6 to 30 carbon atoms, more preferably 6 to 18, and most preferably 6 to 15. The alicyclic ring has 3 to 12 carbon atoms, more preferably 3 to 10, and most preferably 3 to 6. Specific examples may include benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, naphthocyclopropane, naphthocyclobutane, naphthocyclopentane, naphthocyclohexane, etc., but are not limited thereto.

[0028] 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. The heteroaromatic ring preferably has 2 to 30 carbon atoms, more preferably 2 to 18, and most preferably 2 to 12. The alicyclic ring preferably has 3 to 12 carbon atoms, more preferably 3 to 10, and most preferably 3 to 6. Specific examples may include, but are not limited to, pyridocyclopropyl, pyridocyclobutyl, pyridocyclopentyl, pyridocyclohexyl, pyridinium-benzocycloheptyl, pyrimidinium-cyclopropyl, pyrimidinium-cyclobutyl, pyrimidinium-cyclopentyl, pyrimidinium-benzocyclohexyl, dibenzofuranocyclopropyl, dibenzofuranocyclobutyl, dibenzofuranocyclopentyl, dibenzofuranocyclohexyl, dibenzofuranocycloheptyl, dibenzothiophenecyclopropyl, dibenzothiophenecyclobutyl, dibenzothiophenecyclopentyl, dibenzothiophenecyclohexyl, dibenzothiophenecycloheptyl, carbazocyclopropyl, carbazocyclobutyl, carbazocyclopentyl, carbazocyclohexyl, carbazocycloheptyl, etc.

[0029] The arylene group described in this invention refers to a divalent group obtained by removing two hydrogen atoms from the aromatic carbon atom of an aromatic compound molecule. It can be described using the same principles as the aryl group described above, except that the arylene group is a divalent group.

[0030] The heteroaryl group described in this invention refers to a divalent group in which at least one carbon atom of the aryl group is replaced by a heteroatom. The above description of heteroaryl groups can be applied to it, the difference being that the heteroaryl group is a divalent group.

[0031] This invention provides a heterocyclic compound having the structure shown in Formula 1.

[0032] In Equation 1, the X values ​​are the same or different from each other, and each is independently selected from C or N, wherein there are exactly three X values ​​selected as N; The V values ​​may be the same as or different from each other, and each is independently selected from CH or N; R1 is independently selected from any one of the following: substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C6-C30 aromatic ring and C3-C12 alicyclic ring, and fused cycloalcoholic group of substituted or unsubstituted C2-C30 heteroaryl ring and C3-C12 alicyclic ring; The R2 is independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C6-C30 aromatic ring and C3-C12 alicyclic ring, fused cycloalcoholic group of substituted or unsubstituted C2-C30 heteroaryl ring and C3-C12 alicyclic ring, or adjacent R2 can be interconnected to form a substituted or unsubstituted ring; The n is independently selected from 0, 1, 2, 3 or 4; The M is selected from the following groups:

[0033] The " "This is the connection site with L, L3, or L0; The R3 is independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C6-C30 aromatic ring and C3-C12 alicyclic ring, fused cycloalcoholic group of substituted or unsubstituted C2-C30 heteroaryl ring and C3-C12 alicyclic ring, or adjacent R3s can be interconnected to form substituted or unsubstituted rings; The m is independently selected from 0, 1, 2, or 3; The Ar, Ar1, and Ar2 may be the same as or different from each other, and each is independently selected from any one of the following: substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, fused cyclic groups of substituted or unsubstituted C6-C30 aromatic rings and C3-C12 alicyclic rings, and fused cyclic groups of substituted or unsubstituted C2-C30 heteroaryl rings and C3-C12 alicyclic rings; the substituted groups in "substituted or unsubstituted" of Ar, Ar1, and Ar2 are selected from deuterium, cyano, ... Halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C6-C30 aromatic ring and C3-C12 alicyclic ring, fused cycloalcoholic group of substituted or unsubstituted C2-C30 heteroaryl ring and C3-C12 alicyclic ring, or adjacent substituents may be interconnected to form substituted or unsubstituted rings; The L is independently selected from any one or a combination of substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups; The L0, L1, L2, and L3 may be the same as or different from each other, and are independently selected from any one or a combination of single-bonded, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene. The condition is that the compound of formula 1 does not contain the following structure. .

[0034] Preferably, the heterocyclic compound of Formula 1 is selected from any one of the structures shown in Formulas I-1 to I-6 below.

[0035] ; The definitions of Ar, Ar1, Ar2, L, L0, L1, L2, L3, X, V, R1, R2, R3, m, and n are the same as those described above.

[0036] Preferably, R1 is independently selected from any one or a combination of the following groups, substituted or unsubstituted: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyrene, thioyl, peryl, fluorenyl, furanyl, thiophene, benzofuranyl, benzothiophene, pyridofuranyl, pyridothiophene, di... Benzofuranyl, dibenzothiopheneyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthinyl, o-phenanthrolinel, oxazolyl, thiazolyl, benzooxazolyl, benzothiazolyl, pyridooxazolyl, pyridothiazolyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl.

[0037] Preferably, R2 is independently selected from hydrogen, deuterium, fluorine, chlorine, bromine, iodine, cyano, trifluoromethyl, or selected from any one or a combination of the following substituted or unsubstituted groups: methyl, ethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, phenylenetriene, pyrene, hydroxyl, perylene, fluorenyl, furanyl, thiophene, benzofuranyl Benzothiophene, pyridofuran, pyridothiophene, dibenzofuran, dibenzothiophene, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl, naphthinyl, o-phenanthrolinel, oxazolyl, thiazolyl, benzooxazolyl, benzothiazolyl, pyridooxazolyl, pyridothiazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, triphenylsilyl, or two adjacent R2s can be linked together to form substituted or unsubstituted: benzene ring, naphthyl ring, pyridine ring, pyrimidinyl ring.

[0038] Preferably, R3 is independently selected from hydrogen, deuterium, fluorine, chlorine, bromine, iodine, cyano, trifluoromethyl, or selected from any one or a combination of the following substituted or unsubstituted groups: methyl, ethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, phenylenetriene, pyrene, alkyl, perylene, fluorenyl, furanyl, thiophene. Benzofuranyl, benzothiopheneyl, pyridofuranyl, pyridothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl, naphthinyl, o-phenanthrolinel, oxazolyl, thiazolyl, benzooxazolyl, benzothiazolyl, pyridooxazolyl, pyridothiazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, triphenylsilyl, or two adjacent R3s may be linked together to form substituted or unsubstituted rings.

[0039] Preferably, the " Choose from any of the structures shown below.

[0040] ; The " "Indicates the connection site with L3; The definitions of Ar1, Ar2, L1, and L2 are the same as those described above.

[0041] Preferably, Ar, Ar1, and Ar2 are each independently selected from any one of the following structures.

[0042]

[0043]

[0044]

[0045]

[0046]

[0047]

[0048]

[0049]

[0050]

[0051]

[0052]

[0053]

[0054] ; The t values ​​may be the same as or different from each other, and are each independently selected from CH or N; The R4s may be the same as or different from each other, and each is independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C6-C30 aromatic ring and C3-C12 alicyclic ring, fused cycloalcoholic group of substituted or unsubstituted C2-C30 heteroaryl ring and C3-C12 alicyclic ring, or two adjacent R4s are connected to each other to form a substituted or unsubstituted ring; The Ra may be the same as or different from each other, and each is independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C6-C30 aromatic ring and C3-C12 alicyclic ring, fused cycloalcoholic group of substituted or unsubstituted C2-C30 heteroaryl ring and C3-C12 alicyclic ring, or two adjacent Ra are connected to each other to form a substituted or unsubstituted ring; The Rc may be the same as or different from each other, and each is independently selected from any one of the following: substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C6-C30 aromatic ring and C3-C12 alicyclic ring, and fused cycloalcoholic group of substituted or unsubstituted C2-C30 heteroaryl ring and C3-C12 alicyclic ring; The Rx and Rx' may be the same as or different from each other, and are each independently selected from any one of the following: substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl. a1 is independently selected from 0, 1, 2, 3, 4 or 5; a2 is independently selected from 0, 1, 2, 3 or 4; a3 is independently selected from 0, 1, 2 or 3; a4 is independently selected from 0, 1, 2, 3, 4, 5, 6 or 7; a5 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; a6 is independently selected from 0, 1, 2, 3, 4, 5 or 6; a7 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; a8 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; and a9 is independently selected from 0, 1 or 2. f1 is independently selected from 0, 1, 2, 3 or 4; f2 is independently selected from 0, 1, 2, 3, 4, 5 or 6; f3 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; f4 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; and f5 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14.

[0055] More preferably, at most two or at most one t in each structure are selected from N.

[0056] More preferably, R4 is independently selected from hydrogen, deuterium, fluorine, chlorine, bromine, iodine, cyano, trifluoromethyl, or selected from any one or a combination of the following substituted or unsubstituted groups: methyl, ethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, sanyl Phenyl, pyrene, thyl, peryl, fluorenyl, furanyl, thiophene, benzofuranyl, benzothiophene, pyridofuranyl, pyridothiophene, dibenzofuranyl, dibenzothiophene, pyridyl, pyrimidinyl, pyrazinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, o-phenanthrolinel, oxazolyl, thiazolyl, benzooxazolyl, benzothiazolyl, pyridooxazolyl, pyridothiazolyl, or two adjacent R4s may be linked together to form substituted or unsubstituted rings; More preferably, Ra is independently selected from hydrogen, deuterium, fluorine, chlorine, bromine, iodine, cyano, trifluoromethyl, or selected from any one or a combination of the following substituted or unsubstituted groups: methyl, ethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, sanyl Phenyl, pyrene, alkyl, peryl, fluorenyl, furanyl, thiophene, benzofuranyl, benzothiophene, pyridofuranyl, pyridothiophene, dibenzofuranyl, dibenzothiophene, pyridyl, pyrimidinyl, pyrazinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalolinyl, naphthidyl, o-phenanthrolinel, oxazolyl, thiazolyl, benzooxazolyl, benzothiazolyl, pyridooxazolyl, pyridothiazolyl, or two adjacent Ra may be linked together to form substituted or unsubstituted rings; More preferably, the Rc is independently selected from any one or a combination of the following groups, substituted or unsubstituted: methyl, ethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenyl Phenylidene, pyrene, thionyl, perylene, fluorenyl, furanyl, thiophene, benzofuranyl, benzothiophene, pyridofuranyl, pyridothiophene, dibenzofuranyl, dibenzothiophene, pyridyl, pyrimidinyl, pyrazinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, o-phenanthrolinel, oxazolyl, thiazolyl, benzooxazolyl, benzothiazolyl, pyridooxazolyl, pyridothiazolyl; More preferably, Rx and Rx' are independently selected from any one or a combination of the following groups, substituted or unsubstituted: methyl, ethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, phenylenetriene, pyrene, thioyl, perylene, fluorenyl, furanyl, thiophene, benzofuranyl, benzothiophene Phenoyl, pyridofuranyl, pyridothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl, naphthinyl, o-phenanthrolinel, oxazolyl, thiazolyl, benzooxazolyl, benzothiazolyl, pyridooxazolyl, pyridothiazolyl, or adjacent Rx and Rx' can be linked together to form substituted or unsubstituted rings.

[0057] Preferably, L is selected from any one or a combination of the structures shown below.

[0058]

[0059]

[0060]

[0061]

[0062]

[0063]

[0064]

[0065]

[0066] ; The u values ​​may be the same as or different from each other, and each is independently selected from CH or N; The R5s may be the same as or different from each other, and each is independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C6-C30 aromatic ring and C3-C12 alicyclic ring, fused cycloalcoholic group of substituted or unsubstituted C2-C30 heteroaryl ring and C3-C12 alicyclic ring, or two adjacent R5s may be connected to each other to form a substituted or unsubstituted ring; The Rb may be the same as or different from each other, and each is independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C6-C30 aromatic ring and C3-C12 alicyclic ring, fused cycloalcoholic group of substituted or unsubstituted C2-C30 heteroaryl ring and C3-C12 alicyclic ring, or two adjacent Rb are connected to each other to form a substituted or unsubstituted ring; The Rd may be the same as or different from each other, and each is independently selected from any one of the following: substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C6-C30 aromatic ring and C3-C12 alicyclic ring, and fused cycloalcoholic group of substituted or unsubstituted C2-C30 heteroaryl ring and C3-C12 alicyclic ring; b1 is independently selected from 0, 1, 2, 3, or 4; b2 is independently selected from 0, 1, 2, or 3; b3 is independently selected from 0, 1, or 2; b4 is independently selected from 0, 1, 2, 3, 4, or 5; b5 is independently selected from 0, 1, 2, 3, 4, 5, or 6; b6 is independently selected from 0, 1, 2, 3, 4, 5, 6, or 7; b7 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; b8 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. The g1 is independently selected from 0, 1, 2, 3 or 4, the g2 is independently selected from 0, 1, 2, 3, 4, 5 or 6, the g3 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, and the g4 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.

[0067] More preferably, at most two or at most one u in each structure are selected from N.

[0068] More preferably, R5 is independently selected from hydrogen, deuterium, fluorine, chlorine, bromine, iodine, cyano, trifluoromethyl, or selected from any one or a combination of the following substituted or unsubstituted groups: methyl, ethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, phenylenetriene, pyrene, hydroxyl, perylene, fluorenyl, furanyl, thiophene. R5, benzofuranyl, benzothiophene, pyridofuranyl, pyridothiophene, dibenzofuranyl, dibenzothiophene, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, o-phenanthrolinel, oxazolyl, thiazolyl, benzooxazolyl, benzothiazolyl, pyridooxazolyl, pyridothiazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, triphenylsilyl, or two adjacent R5s may be linked together to form substituted or unsubstituted rings; More preferably, the Rb is independently selected from hydrogen, deuterium, fluorine, chlorine, bromine, iodine, cyano, trifluoromethyl, or selected from any one or a combination of the following substituted or unsubstituted groups: methyl, ethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, phenylenetriene, pyrene, hydroxyl, perylene, fluorenyl, furanyl, thiophene. The following compounds can be substituted or unsubstituted: benzofuranyl, benzothiophenyl, pyridofuranyl, pyridothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, o-phenanthrolinel, oxazolyl, thiazolyl, benzooxazolyl, benzothiazolyl, pyridooxazolyl, pyridothiazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, triphenylsilyl, or two adjacent Rb can be linked together to form substituted or unsubstituted rings; More preferably, the Rd is independently selected from any one or a combination of the following groups, substituted or unsubstituted: methyl, ethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyrene, alkyl, peryl, fluorenyl, furanyl, thiazolyl Fenyl, benzofuranyl, benzothiophenyl, pyridofuranyl, pyridothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl, naphthinyl, o-phenanthrolinel, oxazolyl, thiazolyl, benzooxazolyl, benzothiazolyl, pyridooxazolyl, pyridothiazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, triphenylsilyl.

[0069] Preferably, L0, L1, L2, and L3 are each independently selected from a single bond or any one or a combination of the structures shown below.

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078] ; The y values ​​may be the same as or different from each other, and each is independently selected from CH or N; The R6 may be the same as or different from each other, and each is independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C6-C30 aromatic ring and C3-C12 alicyclic ring, fused cycloalcoholic group of substituted or unsubstituted C2-C30 heteroaryl ring and C3-C12 alicyclic ring, or two adjacent R6 are connected to each other to form a substituted or unsubstituted ring; The Re may be the same as or different from each other, and each is independently selected from any one of the following: substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C6-C30 aromatic ring and C3-C12 alicyclic ring, and fused cycloalcoholic group of substituted or unsubstituted C2-C30 heteroaryl ring and C3-C12 alicyclic ring; The Rf may be the same as or different from each other, and each is independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C6-C30 aromatic ring and C3-C12 alicyclic ring, fused cycloalcoholic group of substituted or unsubstituted C2-C30 heteroaryl ring and C3-C12 alicyclic ring, or two adjacent Rf are connected to each other to form a substituted or unsubstituted ring; The c1 is independently selected from 0, 1, 2, 3, or 4; the c2 is independently selected from 0, 1, 2, or 3; the c3 is independently selected from 0, 1, or 2; the c4 is independently selected from 0, 1, 2, 3, 4, or 5; the c5 is independently selected from 0, 1, 2, 3, 4, 5, or 6; the c6 is independently selected from 0, 1, 2, 3, 4, 5, 6, or 7; the c7 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; and the c8 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. h1 is independently selected from 0, 1, 2, 3 or 4, h2 is independently selected from 0, 1, 2, 3, 4, 5 or 6, h3 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, and h4 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.

[0079] More preferably, R6 is independently selected from hydrogen, deuterium, fluorine, chlorine, bromine, iodine, cyano, trifluoromethyl, or selected from any one or a combination of the following substituted or unsubstituted groups: methyl, ethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, phenylenetriene, pyrene, hydroxyl, perylene, fluorenyl, furanyl, thiophene. The following compounds can be linked together to form substituted or unsubstituted rings: benzofuranyl, benzothiophenyl, pyridofuranyl, pyridothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl, naphthinyl, o-phenanthrolinel, oxazolyl, thiazolyl, benzooxazolyl, benzothiazolyl, pyridooxazolyl, pyridothiazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, triphenylsilyl, or two adjacent R6 groups can be linked together to form substituted or unsubstituted rings; More preferably, the Re is independently selected from any one or a combination of the following groups, substituted or unsubstituted: methyl, ethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyrene, alkyl, peryl, fluorenyl, furanyl, thiazolyl Fenyl, benzofuranyl, benzothiophenyl, pyridofuranyl, pyridothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, o-phenanthrolinel, oxazolyl, thiazolyl, benzooxazolyl, benzothiazolyl, pyridooxazolyl, pyridothiazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, triphenylsilyl; More preferably, the Rf is independently selected from hydrogen, deuterium, fluorine, chlorine, bromine, iodine, cyano, trifluoromethyl, or selected from any one or a combination of the following substituted or unsubstituted groups: methyl, ethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, phenylenetriene, pyrene, alkyl, perylene, fluorenyl, furanyl, thiophene. The following compounds can be linked together to form substituted or unsubstituted rings: benzofuranyl, benzothiophenyl, pyridinyl, pyridinyl, dibenzofuranyl, dibenzothiophenyl, pyridinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl, naphthinyl, o-phenanthrolinel, oxazolyl, thiazolyl, benzooxazolyl, benzothiazolyl, pyridinyloxazolyl, pyridinylthiazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, triphenylsilyl, or two adjacent Rf groups can be linked together to form substituted or unsubstituted rings.

[0080] Preferably, the Choose any one of the structures shown below.

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088] ; The R2s may be the same as or different from each other, and each is independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C6-C30 aromatic ring and C3-C12 alicyclic ring, fused cycloalcoholic group of substituted or unsubstituted C2-C30 heteroaryl ring and C3-C12 alicyclic ring, or two adjacent R2s are connected to each other to form a substituted or unsubstituted ring; The R7s may be the same as or different from each other, and each is independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C6-C30 aromatic ring and C3-C12 alicyclic ring, fused cycloalcoholic group of substituted or unsubstituted C2-C30 heteroaryl ring and C3-C12 alicyclic ring, or two adjacent R7s are connected to each other to form a substituted or unsubstituted ring; The Rgs may be the same as or different from each other, and each is independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C6-C30 aromatic ring and C3-C12 alicyclic ring, fused cycloalcoholic group of substituted or unsubstituted C2-C30 heteroaryl ring and C3-C12 alicyclic ring, or adjacent Rgs may be connected to each other to form a substituted or unsubstituted ring; The n is independently selected from 0, 1, 2, 3 or 4; the n1 is independently selected from 0, 1, 2, 3, 4, 5 or 6; the n2 is independently selected from 0, 1, 2 or 3; and the n3 is independently selected from 0, 1 or 2. The d1 is independently selected from 0, 1, 2, 3, 4 or 5; the d2 is independently selected from 0, 1, 2, 3 or 4; the d3 is independently selected from 0, 1, 2, 3, 4, 5, 6 or 7; the d4 is independently selected from 0, 1, 2 or 3; the d5 is independently selected from 0, 1, 2, 3, 4, 5 or 6; and the d6 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9. The r1 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; the r2 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; the r3 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the r4 is independently selected from 0, 1, 2, 3, 4, 5 or 6; and the r5 is independently selected from 0, 1, 2, 3 or 4.

[0089] More preferably, R2 is independently selected from hydrogen, deuterium, fluorine, chlorine, bromine, iodine, cyano, trifluoromethyl, or selected from any one or a combination of the following substituted or unsubstituted groups: methyl, ethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, phenylenetriene, pyrene, alkyl, perylene, fluorenyl, furanyl, thiophene. The following compounds can be used: benzofuranyl, benzothiophenyl, pyridofuranyl, pyridothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, o-phenanthrolinel, oxazolyl, thiazolyl, benzooxazolyl, benzothiazolyl, pyridooxazolyl, pyridothiazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, triphenylsilyl, or two adjacent R2s can be linked together to form substituted or unsubstituted rings; More preferably, R7 is independently selected from hydrogen, deuterium, fluorine, chlorine, bromine, iodine, cyano, trifluoromethyl, or selected from any one or a combination of the following substituted or unsubstituted groups: methyl, ethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, phenylenetriene, pyrene, hydroxyl, perylene, fluorenyl, furanyl, thiophene. The following compounds can be linked together to form substituted or unsubstituted rings: benzofuranyl, benzothiophenyl, pyridofuranyl, pyridothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl, naphthinyl, o-phenanthrolinel, oxazolyl, thiazolyl, benzooxazolyl, benzothiazolyl, pyridooxazolyl, pyridothiazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, triphenylsilyl, or two adjacent R7s can be linked together to form substituted or unsubstituted rings; More preferably, Rg is independently selected from hydrogen, deuterium, fluorine, chlorine, bromine, iodine, cyano, trifluoromethyl, or selected from any one or a combination of the following substituted or unsubstituted groups: methyl, ethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, phenylenetriene, pyrene, hydroxyl, perylene, fluorenyl, furanyl, thiophene. Rg, benzofuranyl, benzothiopheneyl, pyridofuranyl, pyridothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl, naphthinyl, o-phenanthrolinel, oxazolyl, thiazolyl, benzooxazolyl, benzothiazolyl, pyridooxazolyl, pyridothiazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, triphenylsilyl, or two adjacent Rgs may be linked together to form substituted or unsubstituted rings.

[0090] Most preferably, the heterocyclic compound is selected from any one of the following structures:

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[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]

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[0303] ; The above lists some specific structural forms of heterocyclic compounds represented by Formula 1 of this invention. However, this invention is not limited to these listed chemical structures. Any compound based on the structure shown in Formula 1, whose substituents fall within the scope defined by this invention, is within the protection scope of this invention.

[0304] The preparation method of the heterocyclic compound shown in Formula 1 of this invention is not particularly limited, and conventional methods well known to those skilled in the art can be used, such as the Miyaura borylation reaction, the Suzuki coupling reaction, etc. The heterocyclic compound shown in Formula 1 of this invention can be prepared using the synthetic route shown below, but is not limited thereto.

[0305] [Synthetic route of compound Equation 1]

[0306] [Synthesis route for intermediate c]

[0307] The limitations of Ar, Ar1, Ar2, L, L0, L1, L2, L3, X, V, R1, R2, R3, m, and n are the same as those in Equation 1 above; Xa, Xb, Xc, Xd, and Xe are each independently selected from any one of Cl, Br, and I; The Q is independently selected from or Any one of them.

[0308] The present invention also provides an organic electroluminescent device comprising at least one of the heterocyclic compounds described in the present invention.

[0309] Preferably, the organic electroluminescent device includes an anode, a cathode, and an organic layer, wherein the organic layer is located between the anode and the cathode or outside one or more electrodes of the anode and the cathode, and the organic layer contains at least one of the heterocyclic compounds described in this invention.

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

[0311] Preferably, the organic layer includes an electron transport layer, which includes at least one of the heterocyclic compounds described in this invention.

[0312] Preferably, 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 includes a light-emitting layer, which contains at least one of the heterocyclic compounds described in this invention.

[0314] More preferably, the light-emitting layer comprises a host material and a guest material, wherein the host material comprises at least one of the heterocyclic compounds described in this invention.

[0315] 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.

[0316] Preferably, the organic layer is located outside either the anode or the cathode electrode, and the organic layer includes a light efficiency improvement layer, which includes at least one of the heterocyclic compounds described in this invention.

[0317] The organic electroluminescent devices described in this invention are typically fabricated on a substrate. The substrate material is selected to ensure stability during the formation of the electrodes and organic layers, preferably a material that does not undergo deformation or chemical change. Specific examples of substrate materials usable in this invention include, but are not limited to, glass, plastics, polymer films, silicon, etc. When the substrate is opaque, the electrodes opposite it are preferably transparent or translucent.

[0318] This invention does not impose any particular limitation on the materials of the thin films in the organic electroluminescent device; substances known in the art can be used. The following describes each organic layer and the electrodes on both sides of the organic electroluminescent device: The anode of this invention preferably has a high work function, improving hole injection efficiency. The anode material includes, but is not limited to, transparent conductive metal oxides, metals, metal alloys, and conductive polymers. Specific examples may include copper (Cu), silver (Ag), gold (Au), magnesium-silver (Mg-Ag), aluminum-lithium (Al-Li), zinc oxide (ZnO), tin oxide (SnO2), indium tin oxide (ITO), indium zinc oxide (IZO), ZnO / Al, SnO2 / Sb, ITO / Ag / ITO, poly(3-methylthiophene), polypyrrole, and polyaniline, but are not limited to these.

[0319] The hole injection layer described in this invention preferably uses a material with good hole injection capability, which can effectively reduce the interfacial barrier between the anode and the hole transport layer. The hole injection material includes aromatic amine derivatives, perylene derivatives, hexanitrile hexaazabenzophenanthrene compounds, quinacridone compounds, anthraquinone compounds, phthalocyanine metal complexes, polycyano conjugated organic compounds, polymers, etc. Specific examples may include copper phthalocyanine (CuPc), 4,4',4''-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4”-tris[2-naphthylphenylamino]triphenylamine (2-TNATA), 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazabenzophenanthrene (HAT-CN), etc., but is not limited to these.

[0320] The hole transport layer described in this invention is preferably made of a material with high hole mobility. The hole transport material includes, but is not limited to, carbazole derivatives, aromatic amine derivatives, benzidine derivatives, fluorene derivatives, phthalocyanine compounds, polymers, etc. Specific examples may include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), 4,4'-cyclohexylbis[N,N-di(4-methylphenyl)aniline] (TAPC), 4,4'-bis[N-(spiro-9,9'-bisfluorene-2-yl)-N-phenylamino]biphenyl (BSPB), 4,4'-bis(9-carbazolyl)biphenyl (CBP), 4,4',4”-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4”-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (MTDATA), 1,3,5-tris(9-carbazolyl)benzene (TCB), 4 ,4' ,4”-tris(carbazole-9-yl)triphenylamine (TCTA), etc., but not limited to these.

[0321] The electron blocking layer of this invention is preferably made of a material with good hole transport and electron blocking capabilities, which can effectively transport holes and restrict electrons from escaping to the interface of the light-emitting layer. The electron blocking material includes, but is not limited to, aromatic amine derivatives, carbazole derivatives, fluorene derivatives, etc. Specific examples may include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB), N,N-bis([1,1'-biphenyl]-4-)-(9H-carbazole-9-yl)-[1,1'-biphenyl]-4-amine, 4,4',4”-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (MTDATA), etc., but is not limited to these.

[0322] The light-emitting layer of the present invention may be composed of only the guest material, or it may be in the form of dispersing the guest material in the host material, wherein the host material may be composed of a single material or multiple materials.

[0323] The host material described in this invention must possess bipolar charge transport characteristics and have appropriate energy levels to effectively transfer excitation energy to the guest luminescent material. The host material includes, but is not limited to, heterocyclic compounds, metal complexes, fused polycyclic aromatic compounds, aromatic amine derivatives, carbazole derivatives, stilbeneylaryl derivatives, anthracene derivatives, and pyrene derivatives. Specific examples may include, but are not limited to, 4,4'-bis(carbazole-9-yl)biphenyl (CBP), 4,4'-bis(9-carbazole)-2,2'-dimethylbiphenyl (CDBP), 9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole (CZSi), 1,3-bis(N-carbazole)benzene (MCP), 9,10-bis(2-naphthyl)anthracene (ADN), 2-tert-butyl-9,10-bis(2-naphthyl)anthracene (TBADN), tris(8-hydroxyquinoline)aluminum (Alq3), and heterocyclic compounds described in this invention. Heterocyclic compounds described in this invention are preferred.

[0324] The guest material described in this invention can be a fluorescent material, a phosphorescent material, or a TADF material, or a combination of fluorescent and phosphorescent materials. The guest material includes, but is not limited to, aromatic amine derivatives, boron nitrogen compounds, anthracene derivatives, pyrene derivatives, perylene derivatives, and metal complexes. 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-tetra-tert-butylperylene (TBPe), 1,4-bis(4-(9H-carbazole-9-yl)styryl)benzene (BCzSB), etc., but is not limited to these.

[0325] The P-type charge-generating layer material of this invention includes organic materials doped with metals or P-type dopants. For example, the metal may include alloys of one or two of the following: aluminum (Al), copper (Cu), iron (Fe), lead (Pb), zinc (Zn), gold (Au), platinum (Pt), tungsten (W), indium (In), molybdenum (Mo), nickel (Ni), and titanium (Ti). The P-type dopant may include F4-TCNQ, iodine (I), ferric chloride (FeCl3), ferric fluoride (FeF3), and antimony chloride (SbCl5), and the substrate may include at least one selected from the group consisting of NPB, TPD, TNB, and HAT-CN, but is not limited thereto.

[0326] The N-type charge-generating layer material described in this invention, in addition to the heterocyclic compounds provided by this invention, may also include N-type doped organic materials such as alkali metals like Li, Na, K, Rb, Cs, and Fr; alkaline earth metals like Be, Mg, Ca, Sr, Ba, and Ra; Group 15 metals like Bi (bismuth) and Sb (antimony); lanthanide metals like La (lanthanum), Ce (cerium), Pr (praseodymium), Nd (neodymium), Pm (promethium), Sm (samarium), and Gd (gadolinium); and one or more of the aforementioned metal compounds. Alternatively, it may be an organic N-type dopant that has electron-donating properties and can donate at least a portion of its electron charge to the organic host to form a charge-transfer complex with the organic host. Examples include BEDT-TTF and TTF, but it is not limited to these. The heterocyclic compounds described in this invention are preferred.

[0327] The hole-blocking layer of this invention is preferably made of a material with good electron transport and hole blocking capabilities, which can effectively transport electrons and restrict the escape of holes to the emissive layer interface. The hole-blocking layer material includes metal complexes, quinoline derivatives, imidazole derivatives, o-phenanthroline derivatives, aziridine derivatives, triazole derivatives, etc., but is not limited to these. Specific examples may include 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene (TPBi), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 3,3'-[5'-[3-(3-pyridyl)phenyl][1,1':3',1”-terphenyl]-3,3”-diyl]dipyridine (TmPyPB), heterocyclic compounds of this invention, etc., but are not limited to these. Heterocyclic compounds of this invention are preferred.

[0328] The electron transport layer of this invention is preferably made of a material with high electron mobility. The electron transport material includes, but is not limited to, imidazole derivatives, phenanthroline derivatives, pyridine derivatives, quinoline derivatives, azabenzene derivatives, oxazole derivatives, thiazole derivatives, and metal complexes. Specific examples may include 8-hydroxyquinoline aluminum (Alq3), 2,9-bis(naphthyl-2-yl)-4,7-diphenyl-1,10-phenanthroline (NBphen), 1,3,5-tris(4-pyridin-3-ylphenyl)benzene (TpPyPB), 1,3,5-tris(4-pyridylquinoline-2-yl)benzene (TPyQB), 1,3,5-tris(N-phenyl-2-benzimidazole)benzene (TPBi), and heterocyclic compounds of this invention, but are not limited to these. Heterocyclic compounds of this invention are preferred.

[0329] The electron injection layer of the present invention is preferably made of a material capable of reducing the interfacial barrier between the cathode and the electron transport layer. The electron injection material includes alkali metals, alkaline earth metals, rare earth metals, oxides, halides and organic complexes containing these metals, etc. Specific examples may include lithium (Li), ytterbium (Yb), terbium (Tb), lithium fluoride (LiF), calcium fluoride (CaF2), lithium 8-hydroxyquinoline (Liq), lithium oxide (Li2O), barium oxide (BaO), cesium carbonate (Cs2CO3), etc., but are not limited thereto.

[0330] The cathode of the present invention is preferably made of a material with a low work function. The cathode material includes metals, alloys, metal oxides, etc., and specific examples may include lithium (Li), magnesium (Mg), silver (Ag), aluminum (Al), indium (In), LiF / Al, Mg / Ag, etc., but are not limited thereto.

[0331] The capping layer of this invention preferably uses a material with a high refractive index, which contributes to improving the light efficiency of organic light-emitting devices, especially to improving external luminous efficiency. The capping layer material includes, but is not limited to, metal oxides, metal nitrides, metal fluorides, aromatic amine derivatives, carbazole derivatives, etc. Specific examples of the capping layer material may include, but are not limited to, tris(8-hydroxyquinoline)aluminum (Alq3), zinc oxide (ZnO), silicon dioxide (SiO2), cesium fluoride (CsF), lithium fluoride (LiF), N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), 4,4'-di(9-carbazole)biphenyl (CBP), etc. Heterocyclic compounds of this invention are preferred.

[0332] The preparation method of each thin film in the organic electroluminescent device of the present invention is not particularly limited. Vacuum evaporation, spin coating, vapor deposition, blade coating, laser thermal transfer, electrospray coating, slot coating, dip coating, etc. can be used, but are not limited to these.

[0333] 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.

[0334] The organic electroluminescent device of the present invention can be a top-emitting type, a bottom-emitting type, or a bidirectional-emitting type.

[0335] The organic electroluminescent device provided by this invention can be widely used in electronic equipment and lighting fields, specifically in products such as mobile phone displays, tablet computer displays, smart wearable device displays, large-size displays such as televisions, VR devices, and vehicle systems.

[0336] The invention is explained in more detail through the following examples, but is not intended to limit the invention. Based on this description, those skilled in the art will be able to practice the invention and prepare other compounds and devices according to the invention within the entire scope disclosed without inventive effort.

[0337] Preparation and characterization of compounds: Description of raw materials, reagents, and characterization equipment: The present invention does not impose any particular restrictions on the source of raw materials and reagents used in the following embodiments, which can be commercially available products or prepared using preparation methods well known to those skilled in the art.

[0338] Mass spectrometry was performed using a Waters G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer, with chloroform as the solvent. Elemental analysis was performed using a Vario EL cube organic elemental analyzer from Elementar GmbH, Germany, with sample masses ranging from 5 to 10 mg.

[0339] [Synthetic Example 1] Preparation of intermediate c-297:

[0340] Preparation of intermediate c-297: Under nitrogen protection, c'-297 (34.64 g, 80 mmol), pinacol diboronate (20.32 g, 80 mmol), and K2CO3 (22.11 g, 160 mmol) were added to a reaction flask, followed by 500 mL of LDM. After purging the air with nitrogen three times, Pd(PPh3)4 (0.92 g, 0.80 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 tetrahydrofuran, separated, and the organic phase was washed three times with distilled water and dried with anhydrous magnesium sulfate. The resulting solid was purified by recrystallization from dichloromethane to obtain intermediate c-297 (35.67 g, 85%); HPLC purity ≥ 99.83%. Mass spectrometry m / z: 524.2838 (theoretical value: 524.2825).

[0341] By substituting the raw materials accordingly, and following the preparation method of intermediate c-297 in Synthesis Example 1, intermediates c-594 and c-930 can be prepared. The raw materials are shown in the table below: Table 1:

[0342] [Synthetic Example 2] Preparation of Compound 1:

[0343] Preparation of intermediate A-1: ​​Under nitrogen protection, a-1 (25.39 g, 80.00 mmol), b-1 (16.33 g, 80.00 mmol), Pd(PPh3)4 (0.92 g, 0.80 mmol), and K2CO3 (16.59 g, 120.00 mmol), along with 600 mL of toluene / ethanol / water (2:1:1), were added to a reaction flask. The mixture was stirred and refluxed for 3.5 h. After the reaction was complete, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from toluene / ethanol (7:1 v / v). The solid was dried to obtain intermediate A-1 (18.41 g, 86%), with an HPLC purity ≥99.83%. Mass spectrometry m / z: 265.9481 (theoretical value: 265.9498).

[0344] Preparation of intermediate B-1: Under nitrogen protection, intermediate A-1 (16.05 g, 60.00 mmol), c-1 (26.66 g, 60.00 mmol), K2CO3 (12.44 g, 90.00 mmol), Pd(dppf)Cl2 (0.44 g, 0.60 mmol), and 500 mL of toluene / ethanol / water (2:1:1) were added to a reaction flask. The mixture was stirred under reflux for 5 h. After the reaction was completed, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from toluene / ethanol = 9:1 (v / v) to obtain intermediate B-1 (24.85 g, 82%), with an HPLC purity ≥ 99.87%. Mass spectrometry m / z: 504.1659 (theoretical value: 504.1645).

[0345] Preparation of intermediate C-1: Under nitrogen protection, intermediate B-1 (20.20 g, 40.00 mmol), pinacol diborate (10.16 g, 40.00 mmol), K2CO3 (8.29 g, 60.00 mmol), Pd(dppf)Cl2 (0.29 g, 0.40 mmol), and 300 mL of dioxane were added to a reaction flask. The mixture was stirred under reflux for 6.5 h. After the reaction was completed, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from dichloromethane to obtain intermediate C-1 (18.85 g, 79%), with an HPLC purity ≥ 99.91%. Mass spectrometry m / z: 596.2871 (theoretical value: 596.2887).

[0346] Preparation of Compound 1: Under nitrogen protection, C-1 (11.93 g, 20.00 mmol), d-1 (5.35 g, 20.00 mmol), K2CO3 (4.15 g, 30.00 mmol), Pd(PPh3)4 (0.23 g, 0.20 mmol), and 200 mL of 1,4-dioxane were added to a reaction flask. The mixture was stirred under reflux for 6 h. After the reaction was completed, the reaction mixture was cooled to room temperature, distilled water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous MgSO4, the solvent was removed under reduced pressure, and the mixture was recrystallized from toluene to give Compound 1 (10.67 g, 76%), HPLC purity ≥ 99.97%, mass spectrometry m / z: 701.2847 (theoretical value: 701.2831). Theoretical elemental content (%) C 52 H 35 N3: C, 88.99; H, 5.03; N, 5.99. Measured elemental content (%): C, 88.96; H, 5.07; N, 5.94.

[0347] [Synthetic Example 3] Preparation of Compound 5:

[0348] Preparation of Compound 5: Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-5 to obtain Compound 5 (10.53 g), with an HPLC purity ≥99.94%. Mass spectrometry m / z: 701.2817 (theoretical value: 701.2831). Theoretical elemental content (%): C 52 H 35 N3: C, 88.99; H, 5.03; N, 5.99. Measured element content (%): C, 88.95; H, 5.05; N, 5.96.

[0349] [Synthetic Example 4] Preparation of Compound 10:

[0350] Preparation of Compound 10: Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-10, and c-1 was replaced with an equimolar amount of c-10, yielding Compound 10 (10.39 g) with an HPLC purity ≥99.96%. Mass spectrometry m / z: 701.2843 (theoretical value: 701.2831). Theoretical elemental content (%): C 52 H 35 N3: C, 88.99; H, 5.03; N, 5.99. Measured elemental content (%): C, 88.95; H, 5.07; N, 5.97.

[0351] [Synthetic Example 5] Preparation of Compound 56:

[0352] Preparation of compound 56: Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-56, and c-1 was replaced with an equimolar amount of c-56, yielding compound 56 (11.36 g) with an HPLC purity ≥99.97%. Mass spectrometry m / z: 777.3159 (theoretical value: 777.3144). Theoretical elemental content (%): C 58 H 39 N3: C, 89.55; H, 5.05; N, 5.40. Measured element content (%): C, 89.51; H, 5.02; N, 5.44.

[0353] [Synthetic Example 6] Preparation of Compound 83:

[0354] Preparation of compound 83: Following the same preparation method as in Synthesis Example 2, b-1 was replaced with an equimolar amount of b-83, c-1 with an equimolar amount of c-56, and d-1 with an equimolar amount of d-83, yielding compound 83 (12.33 g) with an HPLC purity ≥99.98%. Mass spectrometry m / z: 855.3348 (theoretical value: 855.3362). Theoretical elemental content (%): C 62 H 41 N5: C, 86.99; H, 4.83; N, 8.18. Measured elemental content (%): C, 86.96; H, 4.85; N, 8.14.

[0355] [Synthetic Example 7] Preparation of Compound 97:

[0356] Preparation of Compound 97: Following the same preparation method as in Synthesis Example 2, b-1 was replaced with an equimolar amount of b-97, and c-1 was replaced with an equimolar amount of c-97, yielding Compound 97 (13.55 g) with an HPLC purity ≥99.93%. Mass spectrometry m / z: 953.3782 (theoretical value: 953.3770). Theoretical elemental content (%): C 72 H 47 N3: C, 90.63; H, 4.97; N, 4.40. Measured element content (%): C, 90.66; H, 4.94; N, 4.35.

[0357] [Synthetic Example 8] Preparation of Compound 108:

[0358] Preparation of compound 108: Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-56, b-1 with an equimolar amount of b-108, and d-1 with an equimolar amount of d-108, yielding compound 108 (12.66 g) with an HPLC purity ≥99.97%. Mass spectrometry m / z: 903.3631 (theoretical value: 903.3613). Theoretical elemental content (%): C 68 H 45 N3: C, 90.34; H, 5.02; N, 4.65. Measured elemental content (%): C, 90.37; H, 5.06; N, 4.61.

[0359] [Synthetic Example 9] Preparation of Compound 131:

[0360] Preparation of compound 131: Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-56, c-1 with an equimolar amount of c-10, and d-1 with an equimolar amount of d-131, yielding compound 131 (11.67 g) with an HPLC purity ≥99.95%. Mass spectrometry m / z: 777.3157 (theoretical value: 777.3144). Theoretical elemental content (%): C 58 H 39 N3: C, 89.55; H, 5.05; N, 5.40. Measured element content (%): C, 89.51; H, 5.08; N, 5.43.

[0361] [Synthetic Example 10] Preparation of Compound 137:

[0362] Preparation of compound 137: Following the same preparation method as in Synthesis Example 2, c-1 was replaced with an equimolar amount of c-137, and d-1 was replaced with an equimolar amount of d-137 to obtain compound 137 (11.51 g), with an HPLC purity ≥99.96%. Mass spectrometry m / z: 777.3128 (theoretical value: 777.3144). Theoretical elemental content (%): C 58 H 39 N3: C, 89.55; H, 5.05; N, 5.40. Measured element content (%): C, 89.52; H, 5.07; N, 5.36.

[0363] [Synthetic Example 11] Preparation of Compound 147:

[0364] Preparation of compound 147: Following the same preparation method as in Synthesis Example 2, b-1 was replaced with an equimolar amount of b-147 to obtain compound 147 (10.32 g), with an HPLC purity ≥99.98%. Mass spectrometry m / z: 706.3130 (theoretical value: 706.3145). Theoretical elemental content (%): C 52 H 30 D5N3: C, 88.35; H, 5.70; N, 5.94. Measured elemental content (%): C, 88.32; H, 5.75; N, 5.90.

[0365] [Synthetic Example 12] Preparation of Compound 199:

[0366] Preparation of compound 199: Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-199, b-1 with an equimolar amount of b-199, and d-1 with an equimolar amount of d-131, yielding compound 199 (11.56 g) with an HPLC purity ≥99.92%. Mass spectrometry m / z: 802.3077 (theoretical value: 802.3096). Theoretical elemental content (%): C 59 H 38 N4: C, 88.25; H, 4.77; N, 6.98. Measured elemental content (%): C, 88.28; H, 4.74; N, 6.95.

[0367] [Synthetic Example 13] Preparation of Compound 242:

[0368] Preparation of compound 242: Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-56, and d-1 was replaced with an equimolar amount of d-242 to obtain compound 242 (11.10 g), with an HPLC purity ≥99.96%. Mass spectrometry m / z: 781.3379 (theoretical value: 781.3395). Theoretical elemental content (%): C 58 H 35 D4N3: C, 89.08; H, 5.54; N, 5.37. Measured elemental content (%): C, 89.11; H, 5.51; N, 5.39.

[0369] [Synthetic Example 14] Preparation of Compound 297:

[0370] Preparation of compound 297: Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-10, c-1 with an equimolar amount of c-297, and d-1 with an equimolar amount of d-297, yielding compound 297 (11.02 g) with an HPLC purity ≥99.97%. Mass spectrometry m / z: 786.3719 (theoretical value: 786.3709). Theoretical elemental content (%): C 58 H 30 D9N3: C, 88.52; H, 6.15; N, 5.34. Measured elemental content (%): C, 88.55; H, 6.11; N, 5.30.

[0371] [Synthetic Example 15] Preparation of Compound 307:

[0372] Preparation of compound 307: Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-56, c-1 with an equimolar amount of c-307, and d-1 with an equimolar amount of d-307, yielding compound 307 (12.42 g) with an HPLC purity ≥99.94%. Mass spectrometry m / z: 827.3315 (theoretical value: 827.3300). Theoretical elemental content (%): C 62 H 41 N3: C, 89.93; H, 4.99; N, 5.07. Measured element content (%): C, 89.90; H, 4.96; N, 5.11.

[0373] [Synthetic Example 16] Preparation of Compound 391:

[0374] Preparation of compound 391: Following the same preparation method as in Synthesis Example 2, b-1 was replaced with an equimolar amount of b-391, and c-1 was replaced with an equimolar amount of c-137, yielding compound 391 (14.15 g) with an HPLC purity ≥99.95%. Mass spectrometry m / z: 955.3546 (theoretical value: 955.3563). Theoretical elemental content (%): C 71 H 45 N3O: C, 89.19; H, 4.74; N, 4.39. Measured elemental content (%): C, 89.16; H, 4.78; N, 4.35.

[0375] [Synthetic Example 17] Preparation of Compound 394:

[0376] Preparation of compound 394: Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-199, b-1 with an equimolar amount of b-394, and d-1 with an equimolar amount of d-394, yielding compound 394 (13.17 g) with an HPLC purity ≥99.92%. Mass spectrometry m / z: 901.3471 (theoretical value: 901.3457). Theoretical elemental content (%): C 68 H 43 N3: C, 90.54; H, 4.80; N, 4.66. Measured elemental content (%): C, 90.57; H, 4.76; N, 4.62.

[0377] [Synthetic Example 18] Preparation of Compound 445:

[0378] Preparation of compound 445: Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-56, b-1 with an equimolar amount of b-445, and d-1 with an equimolar amount of d-445, yielding compound 445 (13.83 g) with an HPLC purity ≥99.97%. Mass spectrometry m / z: 959.3349 (theoretical value: 959.3334). Theoretical elemental content (%): C 70 H 45 N3S: C, 87.56; H, 4.72; N, 4.38. Measured elemental content (%): C, 87.52; H, 4.75; N, 4.34.

[0379] [Synthetic Example 19] Preparation of Compound 491:

[0380] Preparation of compound 491: Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-56, b-1 with an equimolar amount of b-491, and d-1 with an equimolar amount of d-491, yielding compound 491 (13.49 g) with an HPLC purity ≥99.95%. Mass spectrometry m / z: 949.4378 (theoretical value: 949.4396). Theoretical elemental content (%): C 71 H 55 N3: C, 89.74; H, 5.83; N, 4.42. Measured element content (%): C, 89.77; H, 5.80; N, 4.45.

[0381] [Synthetic Example 20] Preparation of Compound 492:

[0382] Preparation of compound 492: Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-56, b-1 with an equimolar amount of b-492, c-1 with an equimolar amount of c-10, and d-1 with an equimolar amount of d-492, yielding compound 492 (12.49 g) with an HPLC purity ≥99.93%. Mass spectrometry m / z: 891.2657 (theoretical value: 891.2673). Theoretical elemental content (%): C 60 H 34 F5N3: C, 80.80; H, 3.84; N, 4.71. Measured elemental content (%): C, 80.85; H, 3.80; N, 4.74.

[0383] [Synthetic Example 21] Preparation of Compound 493:

[0384] Preparation of compound 493: Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-10, b-1 with an equimolar amount of b-493, and d-1 with an equimolar amount of d-493, yielding compound 493 (13.23 g) with an HPLC purity ≥99.94%. Mass spectrometry m / z: 881.3786 (theoretical value: 881.3770). Theoretical elemental content (%): C 66 H 47 N3: C, 89.87; H, 5.37; N, 4.76. Measured element content (%): C, 89.85; H, 5.34; N, 4.71.

[0385] [Synthetic Example 22] Preparation of Compound 534:

[0386] Preparation of compound 534: Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-56, b-1 with an equimolar amount of b-534, and c-1 with an equimolar amount of c-534, yielding compound 534 (12.95 g) with an HPLC purity ≥99.96%. Mass spectrometry m / z: 874.3678 (theoretical value: 874.3689). Theoretical elemental content (%): C 64 H 34 D7N3O: C, 87.84; H, 5.53; N, 4.80. Measured elemental content (%): C, 87.87; H, 5.50; N, 4.84.

[0387] [Synthetic Example 23] Preparation of Compound 558:

[0388] Preparation of compound 558: Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-199, and d-1 was replaced with an equimolar amount of d-558, yielding compound 558 (12.83 g) with an HPLC purity ≥99.93%. Mass spectrometry m / z: 878.3419 (theoretical value: 878.3409). Theoretical elemental content (%): C 65 H 42 N4: C, 88.81; H, 4.82; N, 6.37. Measured element content (%): C, 88.85; H, 4.85; N, 6.33.

[0389] [Synthetic Example 24] Preparation of Compound 577:

[0390] Preparation of compound 577: Following the same preparation method as in Synthesis Example 2, d-1 was replaced with an equimolar amount of d-577 to obtain compound 577 (12.50 g), with an HPLC purity ≥99.97%. Mass spectrometry m / z: 867.3265 (theoretical value: 867.3250). Theoretical elemental content (%): C 64 H 41 N3O: C, 88.56; H, 4.76; N, 4.84. Measured elemental content (%): C, 88.53; H, 4.72; N, 4.87.

[0391] [Synthetic Example 25] Preparation of Compound 594:

[0392] Preparation of compound 594: Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-594, c-1 with an equimolar amount of c-594, and d-1 with an equimolar amount of d-594, yielding compound 594 (13.65 g) with an HPLC purity ≥99.96%. Mass spectrometry m / z: 960.3272 (theoretical value: 960.3287). Theoretical elemental content (%): C 69 H 44 N4S: C, 86.22; H, 4.61; N, 5.83. Measured elemental content (%): C, 86.25; H, 4.64; N, 5.80.

[0393] [Synthetic Example 26] Preparation of Compound 604:

[0394] Preparation of compound 604: Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-5, c-1 with an equimolar amount of c-604, and d-1 with an equimolar amount of d-604, yielding compound 604 (13.25 g) with an HPLC purity ≥99.93%. Mass spectrometry m / z: 945.3454 (theoretical value: 945.3468). Theoretical elemental content (%): C 68 H 43 N5O: C, 86.33; H, 4.58; N, 7.40. Measured elemental content (%): C, 86.36; H, 4.53; N, 7.44.

[0395] [Synthetic Example 27] Preparation of Compound 653:

[0396] Preparation of compound 653: Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-199, and d-1 was replaced with an equimolar amount of d-653, yielding compound 653 (12.04 g) with an HPLC purity ≥99.95%. Mass spectrometry m / z: 802.3112 (theoretical value: 802.3096). Theoretical elemental content (%): C 59 H 38 N4: C, 88.25; H, 4.77; N, 6.98. Measured elemental content (%): C, 88.28; H, 4.74; N, 6.95.

[0397] [Synthetic Example 28] Preparation of Compound 658:

[0398] Preparation of compound 658: Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-199, b-1 with an equimolar amount of b-658, and d-1 with an equimolar amount of d-658, yielding compound 658 (15.10 g) with an HPLC purity ≥99.96%. Mass spectrometry m / z: 1019.3977 (theoretical value: 1019.3988). Theoretical elemental content (%): C 75 H 49 N5: C, 88.29; H, 4.84; N, 6.86. Measured elemental content (%): C, 88.26; H, 4.80; N, 6.89.

[0399] [Synthetic Example 29] Preparation of Compound 662:

[0400] Preparation of compound 662: Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-10, b-1 with an equimolar amount of b-662, and d-1 with an equimolar amount of d-662, yielding compound 662 (12.10 g) with an HPLC purity ≥99.98%. Mass spectrometry m / z: 828.3267 (theoretical value: 828.3253). Theoretical elemental content (%): C 61 H 40 N4: C, 88.38; H, 4.86; N, 6.76. Measured elemental content (%): C, 88.35; H, 4.89; N, 6.72.

[0401] [Synthetic Example 30] Preparation of Compound 665:

[0402] Preparation of compound 665: Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-10, b-1 with an equimolar amount of b-665, and d-1 with an equimolar amount of d-665, yielding compound 665 (11.27 g) with an HPLC purity ≥99.96%. Mass spectrometry m / z: 782.3059 (theoretical value: 782.3046). Theoretical elemental content (%): C 56 H 38 N4O: C, 85.91; H, 4.89; N, 7.16. Measured elemental content (%): C, 85.95; H, 4.85; N, 7.19.

[0403] [Synthetic Example 31] Preparation of Compound 670:

[0404] Preparation of compound 670: Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-199, b-1 with an equimolar amount of b-670, and d-1 with an equimolar amount of d-670, yielding compound 670 (14.12 g) with an HPLC purity ≥99.94%. Mass spectrometry m / z: 993.4128 (theoretical value: 993.4117). Theoretical elemental content (%): C 72 H 55 N3S: C, 86.97; H, 5.58; N, 4.23. Measured elemental content (%): C, 86.94; H, 5.54; N, 4.27.

[0405] [Synthetic Example 32] Preparation of Compound 672:

[0406] Preparation of compound 672: Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-5, b-1 with an equimolar amount of b-672, c-1 with an equimolar amount of c-10, and d-1 with an equimolar amount of d-672, yielding compound 672 (13.22 g) with an HPLC purity ≥99.96%. Mass spectrometry m / z: 943.2995 (theoretical value: 943.2986). Theoretical elemental content (%): C 64 H 38 F5N3: C, 81.43; H, 4.06; N, 4.45. Measured elemental content (%): C, 81.47; H, 4.02; N, 4.42.

[0407] [Synthetic Example 33] Preparation of Compound 674:

[0408] Preparation of compound 674: Following the same preparation method as in Synthesis Example 2, b-1 was replaced with an equimolar amount of b-674, and d-1 was replaced with an equimolar amount of d-674, yielding compound 674 (13.53 g) with an HPLC purity ≥99.97%. Mass spectrometry m / z: 901.3469 (theoretical value: 901.3457). Theoretical elemental content (%): C 68 H 43 N3: C, 90.54; H, 4.80; N, 4.66. Measured elemental content (%): C, 90.57; H, 4.83; N, 4.62.

[0409] [Synthetic Example 34] Preparation of Compound 678:

[0410] Preparation of compound 678: Following the same preparation method as in Synthesis Example 2, b-1 was replaced with an equimolar amount of b-678, and d-1 was replaced with an equimolar amount of d-678, yielding compound 678 (13.75 g) with an HPLC purity ≥99.93%. Mass spectrometry m / z: 928.3578 (theoretical value: 928.3566). Theoretical elemental content (%): C 69 H 44 N4: C, 89.20; H, 4.77; N, 6.03. Measured element content (%): C, 89.24; H, 4.75; N, 6.07.

[0411] [Synthetic Example 35] Preparation of Compound 814:

[0412] Preparation of compound 814: Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-594, c-1 with an equimolar amount of c-814, and d-1 with an equimolar amount of d-814, yielding compound 814 (11.62 g) with an HPLC purity ≥99.92%. Mass spectrometry m / z: 795.4148 (theoretical value: 795.4164). Theoretical elemental content (%): C 57 H 21 D 17 N4: C, 86.00; H, 6.96; N, 7.04. Measured elemental content (%): C, 86.02; H, 6.93; N, 7.07.

[0413] [Synthetic Example 36] Preparation of Compound 827:

[0414] Preparation of compound 827: Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-56, c-1 with an equimolar amount of c-827, and d-1 with an equimolar amount of d-131, yielding compound 827 (11.92 g) with an HPLC purity ≥99.94%. Mass spectrometry m / z: 827.3314 (theoretical value: 827.3300). Theoretical elemental content (%): C 62 H 41 N3: C, 89.93; H, 4.99; N, 5.07. Measured element content (%): C, 89.96; H, 4.95; N, 5.11.

[0415] [Synthetic Example 37] Preparation of Compound 837:

[0416] Preparation of compound 837: Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-594, c-1 with an equimolar amount of c-837, and d-1 with an equimolar amount of d-837, yielding compound 837 (11.03 g) with an HPLC purity ≥99.96%. Mass spectrometry m / z: 776.2951 (theoretical value: 776.2940). Theoretical elemental content (%): C 57 H 36 N4: C, 88.12; H, 4.67; N, 7.21. Measured elemental content (%): C, 88.15; H, 4.62; N, 7.24.

[0417] [Synthetic Example 38] Preparation of Compound 864:

[0418] Preparation of compound 864: Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-5, b-1 with an equimolar amount of b-864, c-1 with an equimolar amount of c-864, and d-1 with an equimolar amount of d-864, yielding compound 864 (13.19 g) with an HPLC purity ≥99.95%. Mass spectrometry m / z: 941.3784 (theoretical value: 941.3770). Theoretical elemental content (%): C 71 H 47 N3: C, 90.51; H, 5.03; N, 4.46. Measured elemental content (%): C, 90.54; H, 5.06; N, 4.42.

[0419] [Synthetic Example 39] Preparation of Compound 898:

[0420] Preparation of compound 898: Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-56, b-1 with an equimolar amount of b-898, and c-1 with an equimolar amount of c-898, yielding compound 898 (12.18 g) with an HPLC purity ≥99.91%. Mass spectrometry m / z: 811.3941 (theoretical value: 811.3926). Theoretical elemental content (%): C 60 H 49 N3: C, 88.74; H, 6.08; N, 5.17. Measured elemental content (%): C, 88.77; H, 6.05; N, 5.19.

[0421] [Synthetic Example 40] Preparation of Compound 905:

[0422] Preparation of compound 905: Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-56, c-1 with an equimolar amount of c-905, and d-1 with an equimolar amount of d-905, yielding compound 905 (13.92 g) with an HPLC purity ≥99.93%. Mass spectrometry m / z: 939.4536 (theoretical value: 939.4552). Theoretical elemental content (%): C 70 H 57 N3: C, 89.42; H, 6.11; N, 4.47. Measured elemental content (%): C, 89.45; H, 6.14; N, 4.42.

[0423] [Synthetic Example 41] Preparation of Compound 930:

[0424] Preparation of compound 930: Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-10, b-1 with an equimolar amount of b-930, and c-1 with an equimolar amount of c-930, yielding compound 930 (13.76 g) with an HPLC purity ≥99.98%. Mass spectrometry m / z: 941.3535 (theoretical value: 941.3518). Theoretical elemental content (%): C 69 H 43 N5: C, 87.97; H, 4.60; N, 7.43. Measured elemental content (%): C, 87.95; H, 4.64; N, 7.41.

[0425] [Synthetic Example 42] Preparation of Compound 934:

[0426] Preparation of compound 934: Following the same preparation method as in Synthesis Example 2, c-1 was replaced with an equimolar amount of c-934, and d-1 was replaced with an equimolar amount of d-934, yielding compound 934 (13.08 g) with an HPLC purity ≥99.92%. Mass spectrometry m / z: 907.3944 (theoretical value: 907.3926). Theoretical elemental content (%): C 68 H 49 N3: C, 89.93; H, 5.44; N, 4.63. Measured element content (%): C, 89.95; H, 5.41; N, 4.67.

[0427] [Synthetic Example 43] Preparation of Compound 940:

[0428] Preparation of compound 940: Following the same preparation method as in Synthesis Example 2, b-1 was replaced with an equimolar amount of b-940, and c-1 was replaced with an equimolar amount of c-940, yielding compound 940 (12.33 g) with an HPLC purity ≥99.95%. Mass spectrometry m / z: 867.3626 (theoretical value: 867.3613). Theoretical elemental content (%): C 65 H 45 N3: C, 89.93; H, 5.23; N, 4.84. Measured elemental content (%): C, 89.97; H, 5.20; N, 4.86.

[0429] [Synthetic Example 44] Preparation of Compound 970:

[0430] Preparation of compound 970: Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-56, c-1 with an equimolar amount of c-970, and d-1 with an equimolar amount of d-970, yielding compound 970 (12.22 g) with an HPLC purity ≥99.96%. Mass spectrometry m / z: 872.3546 (theoretical value: 872.3563). Theoretical elemental content (%): C 64 H 36 D5N3O: C, 88.04; H, 5.31; N, 4.81. Measured elemental content (%): C, 88.08; H, 5.28; N, 4.84.

[0431] [Synthetic Example 45] Preparation of Compound 972:

[0432] Preparation of compound 972: Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-5, and c-1 was replaced with an equimolar amount of c-972, yielding compound 972 (11.73 g) with an HPLC purity ≥99.94%. Mass spectrometry m / z: 781.3377 (theoretical value: 781.3395). Theoretical elemental content (%): C 58 H 35 D4N3: C, 89.08; H, 5.54; N, 5.37. Measured elemental content (%): C, 89.11; H, 5.58; N, 5.34.

[0433] [Synthetic Example 46] Preparation of Compound 978:

[0434] Preparation of compound 978: Following the same preparation method as in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-56, b-1 with an equimolar amount of b-978, and c-1 with an equimolar amount of c-978, yielding compound 978 (12.27 g) with an HPLC purity ≥99.96%. Mass spectrometry m / z: 828.3269 (theoretical value: 828.3253). Theoretical elemental content (%): C 61 H 40 N4: C, 88.38; H, 4.86; N, 6.76. Measured elemental content (%): C, 88.42; H, 4.83; N, 6.72.

[0435] Device Examples

[0436] In this invention, the ITO glass substrate is 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 is then ultrasonically cleaned sequentially with acetone and isoacetone for 20 minutes each time, and dried at 120°C. The organic materials used in the device fabrication examples are all purified by sublimation, with a purity of over 99.99%.

[0437] A combined IVL testing system was constructed, consisting of testing software, a computer, a Keithley K2400 digital source meter, and a PhotoResearch PR788 spectrophotometer. The device prepared according to this invention was tested at atmospheric pressure and room temperature at a current density of 10 mA / cm². 2 The luminous efficiency and driving voltage were measured. Using McScience's M6000 OLED lifetime testing system, the lifetime of the device prepared in this invention (brightness decaying to 95% of initial brightness) was tested at atmospheric pressure and room temperature, with a test current density of 10 mA / cm². 2 .

[0438] Device Example 1: Fabrication of a Green Organic Electroluminescent Device

[0439] An organic electroluminescent device is fabricated by vacuum evaporating a 15 nm layer of HT-1:HI-1 (mixed in a mass ratio of 97%:3%) onto a glass substrate using ITO as the anode; a hole injection layer is formed by vacuum evaporating a 110 nm layer of HT-1 onto the hole injection layer; an electron blocking layer is formed by vacuum evaporating a 10 nm layer of EB-1 onto the hole transport layer; a light-emitting layer is formed by vacuum evaporating a 30 nm layer of GH-1:GH-2:GD-1 (mixed in a mass ratio of 48%:48%:4%) onto the electron blocking layer; an electron transport layer is formed by vacuum evaporating a 30 nm layer of the compound 1:Liq of this invention (mixed in a mass ratio of 1:1) onto the light-emitting layer; an electron injection layer is formed by vacuum evaporating a 1.0 nm layer of LiF onto the electron transport layer; and a cathode is formed by vacuum evaporating a 120 nm layer of Al onto the electron injection layer.

[0440]

[0441] Device Examples 2-45: Organic electroluminescent devices were prepared by replacing compound 1 in device example 1 with compounds from Table 2 as the electron transport layer material, while keeping the rest of the fabrication process exactly the same.

[0442] Comparative Examples 1-3: Organic electroluminescent devices were prepared by replacing compound 1 in device example 1 with R-1, R-2, and R-3 from Table 2 as electron transport layer materials, while keeping the rest of the fabrication process exactly the same.

[0443] Table 2: Test data on the luminescence characteristics of the organic electroluminescent devices prepared in Device Examples 1-45 and Comparative Examples 1-3

[0444]

[0445] As shown in Table 2, the heterocyclic compounds of this invention have high electron mobility. When used as electron transport layer materials for organic electroluminescent devices, they can reduce the electron injection transport barrier and drive voltage, and improve the binding efficiency of holes and electrons, thereby improving the luminous efficiency and lifetime of organic electroluminescent devices. The compounds of this invention are high-performance electron transport materials.

[0446] Device Example 46: Fabrication of a Blue Organic Electroluminescent Device

[0447] An organic electroluminescent device is fabricated by vacuum evaporating 15 nm of HT-1:HI-1 (mixed at a mass ratio of 97%:3%) onto a glass substrate using ITO as the anode; a hole injection layer is formed by vacuum evaporating 110 nm of HT-1 onto the hole injection layer; a light-emitting layer is formed by vacuum evaporating 30 nm of BH-1:BD-1 (mixed at a mass ratio of 96%:4%) onto the hole transport layer; a hole blocking layer is formed by vacuum evaporating 25 nm of compound 1 of the present invention onto the light-emitting layer; an electron transport layer is formed by vacuum evaporating 30 nm of ET-1:Liq (mixed at a mass ratio of 1:1) onto the hole blocking layer; an electron injection layer is formed by vacuum evaporating 1.0 nm of LiF onto the electron transport layer; and a cathode is formed by vacuum evaporating 120 nm of Al onto the electron injection layer.

[0448]

[0449] Device Examples 47-90: Organic electroluminescent devices were prepared by replacing compound 1 in device example 46 with compounds from Table 3 as hole blocking layer materials, while keeping the rest of the fabrication process exactly the same.

[0450] Comparative Examples 4-6: Organic electroluminescent devices were prepared by replacing compound 1 in device example 46 with R-4, R-5, and R-6 from Table 3 as hole blocking layer materials, while keeping the rest of the fabrication process exactly the same.

[0451] Table 3: Test data on the luminescence characteristics of the organic electroluminescent devices prepared in Device Examples 46-90 and Comparative Examples 4-6

[0452]

[0453] As shown in Table 3, the heterocyclic compounds provided by this invention have suitable energy levels. When used as hole blocking materials in organic electroluminescent devices, the required driving voltage of the device is low, the luminous efficiency is high, and the device lifespan is extended. The compounds of this invention are hole blocking materials with good performance.

[0454] Device Example 91: Fabrication of Green Organic Electroluminescent Devices

[0455] An organic electroluminescent device is fabricated by vacuum evaporating 15 nm of HT-2:HI-1 (mixed in a mass ratio of 97%:3%) onto a glass substrate using ITO as the anode; forming a hole injection layer by vacuum evaporating 110 nm of HT-2 onto the hole injection layer; forming an electron transport layer by vacuum evaporating 10 nm of EB-2 onto the hole transport layer; forming a light-emitting layer by vacuum evaporating 30 nm of the compound 1 of this invention:GH-2:GD-2 (mixed in a mass ratio of 48%:48%:4%) onto the electron blockage layer; forming an electron transport layer by vacuum evaporating 30 nm of ET-1:Liq (mixed in a mass ratio of 1:1) onto the light-emitting layer; forming an electron injection layer by vacuum evaporating 1.0 nm of LiF onto the electron transport layer; and forming a cathode by vacuum evaporating 120 nm of Al onto the electron injection layer.

[0456]

[0457] Device Examples 92-135: Organic electroluminescent devices were prepared by replacing compound 1 in device example 91 with compounds from Table 4 as the N-type host material, with the rest of the fabrication process being exactly the same.

[0458] Comparative Examples 7-8: Organic electroluminescent devices were prepared by replacing compound 1 in device example 91 with R-7 and R-8 from Table 4 as N-type host materials, with the rest of the fabrication process being exactly the same.

[0459] Table 4: Test data on the luminescence characteristics of the organic electroluminescent devices prepared in Device Examples 91-135 and Comparative Examples 7-8

[0460]

[0461] As shown in Table 4, when the compound described in this invention is applied to the N-type host material of organic electroluminescent devices, the devices have higher luminous efficiency and longer lifespan. The compound described in this invention is a high-performance N-type host material.

[0462] It should be noted that the present invention has been specifically described with reference to specific embodiments. For those skilled in the art, various improvements and modifications can be made to the present invention without departing from the principle of the present invention, and these improvements and modifications 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. In Equation 1, the X values ​​are the same or different from each other, and each is independently selected from C or N, wherein there are exactly three X values ​​selected as N; The V values ​​may be the same as or different from each other, and each is independently selected from CH or N; R1 is independently selected from any one of the following: substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C6-C30 aromatic ring and C3-C12 alicyclic ring, and fused cycloalcoholic group of substituted or unsubstituted C2-C30 heteroaryl ring and C3-C12 alicyclic ring; The R2 is independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C6-C30 aromatic ring and C3-C12 alicyclic ring, fused cycloalcoholic group of substituted or unsubstituted C2-C30 heteroaryl ring and C3-C12 alicyclic ring, or adjacent R2 can be interconnected to form a substituted or unsubstituted ring; The n is independently selected from 0, 1, 2, 3 or 4; The M is selected from the following groups: The " "This is the connection site with L, L3, or L0; The R3 is independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C6-C30 aromatic ring and C3-C12 alicyclic ring, fused cycloalcoholic group of substituted or unsubstituted C2-C30 heteroaryl ring and C3-C12 alicyclic ring, or adjacent R3s can be interconnected to form substituted or unsubstituted rings; The m is independently selected from 0, 1, 2, or 3; The Ar, Ar1, and Ar2 may be the same as or different from each other, and each is independently selected from any one of the following: substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, fused cyclic groups of substituted or unsubstituted C6-C30 aromatic rings and C3-C12 alicyclic rings, and fused cyclic groups of substituted or unsubstituted C2-C30 heteroaryl rings and C3-C12 alicyclic rings; the substituted groups in "substituted or unsubstituted" of Ar, Ar1, and Ar2 are selected from deuterium, cyano, ... Halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C6-C30 aromatic ring and C3-C12 alicyclic ring, fused cycloalcoholic group of substituted or unsubstituted C2-C30 heteroaryl ring and C3-C12 alicyclic ring, or adjacent substituents may be interconnected to form substituted or unsubstituted rings; The L is independently selected from any one or a combination of substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups; The L0, L1, L2, and L3 may be the same as or different from each other, and are independently selected from any one or a combination of single-bonded, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene. The condition is that the compound of formula 1 does not contain the following structure. 。 2. The heterocyclic compound according to claim 1, characterized in that, The heterocyclic compound is selected from any one of the structures shown in Formulas I-1 to I-6 below. ； Ar, Ar1, Ar2, L, L0, L1, L2, L3, X, V, R1, R2, R3, m, and n have the meanings defined in claim 1.

3. The heterocyclic compound according to claim 1, characterized in that, Ar, Ar1, and Ar2 are each independently selected from any one of the structures shown below. ； The t values ​​may be the same as or different from each other, and are each independently selected from CH or N; The R4s may be the same as or different from each other, and each is independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C6-C30 aromatic ring and C3-C12 alicyclic ring, fused cycloalcoholic group of substituted or unsubstituted C2-C30 heteroaryl ring and C3-C12 alicyclic ring, or two adjacent R4s are connected to each other to form a substituted or unsubstituted ring; The Ra may be the same as or different from each other, and each is independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C6-C30 aromatic ring and C3-C12 alicyclic ring, fused cycloalcoholic group of substituted or unsubstituted C2-C30 heteroaryl ring and C3-C12 alicyclic ring, or two adjacent Ra are connected to each other to form a substituted or unsubstituted ring; The Rc may be the same as or different from each other, and each is independently selected from any one of the following: substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C6-C30 aromatic ring and C3-C12 alicyclic ring, and fused cycloalcoholic group of substituted or unsubstituted C2-C30 heteroaryl ring and C3-C12 alicyclic ring; The Rx and Rx' may be the same as or different from each other, and are each independently selected from any one of the following: substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl. a1 is independently selected from 0, 1, 2, 3, 4 or 5; a2 is independently selected from 0, 1, 2, 3 or 4; a3 is independently selected from 0, 1, 2 or 3; a4 is independently selected from 0, 1, 2, 3, 4, 5, 6 or 7; a5 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; a6 is independently selected from 0, 1, 2, 3, 4, 5 or 6; a7 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; a8 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; and a9 is independently selected from 0, 1 or 2. f1 is independently selected from 0, 1, 2, 3 or 4; f2 is independently selected from 0, 1, 2, 3, 4, 5 or 6; f3 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; f4 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; and f5 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14.

4. The heterocyclic compound according to claim 1, characterized in that, The L is selected from any one or a combination of the structures shown below. ； The u values ​​may be the same as or different from each other, and each is independently selected from CH or N; The R5s may be the same as or different from each other, and each is independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C6-C30 aromatic ring and C3-C12 alicyclic ring, fused cycloalcoholic group of substituted or unsubstituted C2-C30 heteroaryl ring and C3-C12 alicyclic ring, or two adjacent R5s may be connected to each other to form a substituted or unsubstituted ring; The Rb may be the same as or different from each other, and each is independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C6-C30 aromatic ring and C3-C12 alicyclic ring, fused cycloalcoholic group of substituted or unsubstituted C2-C30 heteroaryl ring and C3-C12 alicyclic ring, or two adjacent Rb are connected to each other to form a substituted or unsubstituted ring; The Rd may be the same as or different from each other, and each is independently selected from any one of the following: substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C6-C30 aromatic ring and C3-C12 alicyclic ring, and fused cycloalcoholic group of substituted or unsubstituted C2-C30 heteroaryl ring and C3-C12 alicyclic ring; b1 is independently selected from 0, 1, 2, 3, or 4; b2 is independently selected from 0, 1, 2, or 3; b3 is independently selected from 0, 1, or 2; b4 is independently selected from 0, 1, 2, 3, 4, or 5; b5 is independently selected from 0, 1, 2, 3, 4, 5, or 6; b6 is independently selected from 0, 1, 2, 3, 4, 5, 6, or 7; b7 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; b8 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. The g1 is independently selected from 0, 1, 2, 3 or 4, the g2 is independently selected from 0, 1, 2, 3, 4, 5 or 6, the g3 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, and the g4 is independently 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, L0, L1, L2, and L3 may be the same as or different from each other, and each is independently selected from a single bond or any one or a combination of the structures shown below. ； The y values ​​may be the same as or different from each other, and each is independently selected from CH or N; The R6 may be the same as or different from each other, and each is independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C6-C30 aromatic ring and C3-C12 alicyclic ring, fused cycloalcoholic group of substituted or unsubstituted C2-C30 heteroaryl ring and C3-C12 alicyclic ring, or two adjacent R6 are connected to each other to form a substituted or unsubstituted ring; The Re may be the same as or different from each other, and each is independently selected from any one of the following: substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C6-C30 aromatic ring and C3-C12 alicyclic ring, and fused cycloalcoholic group of substituted or unsubstituted C2-C30 heteroaryl ring and C3-C12 alicyclic ring; The Rf may be the same as or different from each other, and each is independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C6-C30 aromatic ring and C3-C12 alicyclic ring, fused cycloalcoholic group of substituted or unsubstituted C2-C30 heteroaryl ring and C3-C12 alicyclic ring, or two adjacent Rf are connected to each other to form a substituted or unsubstituted ring; The c1 is independently selected from 0, 1, 2, 3, or 4; the c2 is independently selected from 0, 1, 2, or 3; the c3 is independently selected from 0, 1, or 2; the c4 is independently selected from 0, 1, 2, 3, 4, or 5; the c5 is independently selected from 0, 1, 2, 3, 4, 5, or 6; the c6 is independently selected from 0, 1, 2, 3, 4, 5, 6, or 7; the c7 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; and the c8 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. h1 is independently selected from 0, 1, 2, 3 or 4, h2 is independently selected from 0, 1, 2, 3, 4, 5 or 6, h3 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, and h4 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.

6. The heterocyclic compound according to claim 1, characterized in that, The Choose any one of the structures shown below. ； The R2s may be the same as or different from each other, and each is independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C6-C30 aromatic ring and C3-C12 alicyclic ring, fused cycloalcoholic group of substituted or unsubstituted C2-C30 heteroaryl ring and C3-C12 alicyclic ring, or two adjacent R2s are connected to each other to form a substituted or unsubstituted ring; The R7s may be the same as or different from each other, and each is independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C6-C30 aromatic ring and C3-C12 alicyclic ring, fused cycloalcoholic group of substituted or unsubstituted C2-C30 heteroaryl ring and C3-C12 alicyclic ring, or two adjacent R7s are connected to each other to form a substituted or unsubstituted ring; The Rgs may be the same as or different from each other, and each is independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C6-C30 aromatic ring and C3-C12 alicyclic ring, fused cycloalcoholic group of substituted or unsubstituted C2-C30 heteroaryl ring and C3-C12 alicyclic ring, or adjacent Rgs may be connected to each other to form a substituted or unsubstituted ring; The n is independently selected from 0, 1, 2, 3 or 4; the n1 is independently selected from 0, 1, 2, 3, 4, 5 or 6; the n2 is independently selected from 0, 1, 2 or 3; and the n3 is independently selected from 0, 1 or 2. The d1 is independently selected from 0, 1, 2, 3, 4 or 5; the d2 is independently selected from 0, 1, 2, 3 or 4; the d3 is independently selected from 0, 1, 2, 3, 4, 5, 6 or 7; the d4 is independently selected from 0, 1, 2 or 3; the d5 is independently selected from 0, 1, 2, 3, 4, 5 or 6; and the d6 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9. The r1 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; the r2 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; the r3 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the r4 is independently selected from 0, 1, 2, 3, 4, 5 or 6; and the r5 is independently selected from 0, 1, 2, 3 or 4.

7. The heterocyclic compound according to claim 1, characterized in that, The heterocyclic compound is selected from any one of the structures shown below; 。 8. An organic electroluminescent device, characterized in that, The organic electroluminescent device comprises one or more of the heterocyclic compounds described in any one of claims 1-7.

9. The organic electroluminescent device according to claim 8, characterized in that, The organic electroluminescent device comprises an anode, a cathode, and an organic layer, wherein the organic layer is located between the anode and the cathode or outside one or more electrodes of the anode and the cathode, and the organic layer comprises one or more heterocyclic compounds as described in any one of claims 1-7.

10. The organic electroluminescent device according to claim 9, characterized in that, The organic layer is located between the anode and the cathode, and the organic layer comprises at least one of an electron transport layer, a hole blocking layer and a light-emitting layer, wherein at least one of the electron transport layer, hole blocking layer and light-emitting layer comprises one or more of the heterocyclic compounds according to any one of claims 1-7.

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