Heterocyclic compound and organic electroluminescent device thereof

Abstract

The invention provides a heterocyclic compound and an organic electroluminescent device thereof, and relates to the technical field of organic electroluminescent materials. The heterocyclic compound provided by the invention has relatively high glass transition temperature, good film-forming property and thermal stability, can be used as a covering layer material to be applied to the organic electroluminescent device, can effectively improve the light extraction efficiency, and is beneficial to improving the luminous efficiency and prolonging the service life of the device. Besides, the heterocyclic compound also has a high triplet state energy level and a high hole mobility, and can effectively improve the transmission efficiency of holes in a device as a hole transport material, thereby improving the performance of the device. Meanwhile, as a P-type main body material in a light-emitting layer, the compound can balance electrons and holes in the light-emitting layer, broaden an exciton recombination region and improve exciton recombination efficiency, so that the light-emitting efficiency of a device is improved, and the service life of the device is prolonged. The material can be applied to the fields of information display, illumination and organic solar cells.

Description

Technical Field

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

[0002] Organic light-emitting diodes (OLEDs) are self-emissive electronic devices that directly convert electrical energy into light energy using organic semiconductor materials. They require no additional backlight or complex optical auxiliary structures, offering advantages such as light weight, fast response speed, high resolution, and low power consumption. OLEDs mainly consist of an anode, cathode, hole injection layer, hole transport layer, electron blocking layer, emissive layer, hole blocking layer, electron transport layer, electron injection layer, and capping layer. The electroluminescence process is as follows: Under voltage drive, electrons are injected from the cathode, and holes are injected from the anode. These electrons are transported through their corresponding functional layers to the emissive layer, where they recombine to form high-energy excitons. When these excitons transition from the excited state to the ground state, they release energy, which is then expressed as light, completing the conversion from electrical energy to light energy and achieving electroluminescence.

[0003] Currently, the performance of various organic functional layer materials in OLED devices still has significant shortcomings, falling far short of meeting market demands for high efficiency, long lifespan, and stability. This has become a core bottleneck restricting the development of the industry. For example, capping layer materials face the problem of low refractive index and low glass transition temperature. A lower refractive index exacerbates light loss within the device, while a low glass transition temperature easily leads to thermal deformation of the material during long-term operation, directly damaging the structural stability of the device and significantly shortening its lifespan. Hole transport layer materials have low hole mobility, which easily causes carrier transport imbalance, resulting in decreased charge recombination efficiency of the emissive layer and uneven light emission. In addition, the "triangular contradiction" between driving voltage, luminous efficiency, and lifespan in the main emissive layer material has not been resolved. These shortcomings collectively limit the performance of OLED devices.

[0004] Therefore, developing higher-performance capping layer materials, hole transport layer materials, and host materials, and achieving breakthroughs in key parameters, is the current research focus in the OLED field. Summary of the Invention

[0005] To address the problems existing in the prior art, the present invention provides a heterocyclic compound and its organic electroluminescent device.

[0006] This invention provides a heterocyclic compound, represented by the following formula 1.

[0007]

[0008] Wherein, the same or different v is selected from CR aOr N, or C atoms bonded to L2 or L3;

[0009] The R a The same or different from one selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, or two adjacent R a Bonding forms substituted or unsubstituted benzene rings, naphthalene rings, anthracene rings, phenanthrene rings, and triphenylene rings;

[0010] The same or different R0s are selected from one of the following: hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, fused cycloalkanes of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic rings, or adjacent R0s bonded to form substituted or unsubstituted aromatic rings;

[0011] The c0 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9;

[0012] The Ar1 is selected from one of the groups shown in formula 1-a or 2-a to 2-m below.

[0013]

[0014] The R 21 The same or different from deuterium, halogen, nitro, trifluoromethyl, substituted or unsubstituted silyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, or two adjacent R groups. 21 Bonding forms substituted or unsubstituted alicyclic rings;

[0015] The R 22 The same or different from one of the following: hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, or two adjacent R groups. 22 Bonding forms substituted or unsubstituted aromatic rings;

[0016] The T is selected from O or S;

[0017] The R 23 R 24The same or different from one of the following: hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, or two adjacent R groups. 23 Two Rs 24 Bonding forms substituted or unsubstituted rings;

[0018] The T0 is selected from O, S, or NR. g The T1 is selected from CR i Or N;

[0019] The u that is the same or different is selected from CR 40 Or N;

[0020] The R 40 The same or different from one of the following: hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, or two adjacent R groups. 40 Bonding forms substituted or unsubstituted rings;

[0021] The R i It is selected from one of the following: hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and fused cycloalkanes of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic rings;

[0022] The R d R e The same or different from one selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, or adjacent R d R e Bonding forms substituted or unsubstituted rings;

[0023] The R f Rg The same or different from one of the following: substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic fused cycloalcohol;

[0024] The R 41 R 42 The same or different from one of the following: hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic fused cycloalcoholic group;

[0025] a1 is selected from 0, 1, 2, 3, 4, or 5; a2 is selected from 0, 1, 2, 3, or 4; a3 is selected from 0, 1, 2, or 3; a4 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; a5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; a6 is selected from 1, 2, 3, 4, or 5.

[0026] The Ar2 and Ar3 are selected from one of the groups shown in formula 1-a or 1-b to 1-j below.

[0027]

[0028] The R 25 The same or different from deuterium, halogen, nitro, trifluoromethyl, substituted or unsubstituted silyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, or two adjacent R groups. 25 Bonding forms substituted or unsubstituted alicyclic rings;

[0029] The R 26 The same or different from one of the following: hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, or two adjacent R groups. 26 Bonding forms substituted or unsubstituted rings;

[0030] The z that are the same or different are selected from CR 27 Or N; the z1 that is the same as or different from CR is selected. 28 Or N;

[0031] The R 27 R 28 The same or different from one of the following: hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, or two adjacent R groups. 27 Two Rs 28 Bonding forms substituted or unsubstituted rings;

[0032] Q is selected from O, S, and CR. 29 R 30 Q1 is selected from O, S or NR. 31 Q2 is selected from CR 32 Or N;

[0033] The R 29 R 30 The same or different from one selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, or adjacent R 29 R 30 Bonding forms substituted or unsubstituted rings;

[0034] The R 31 It is selected from one of the following: substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and fused cycloalkanes of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic rings;

[0035] The R 32 It is selected from one of the following: hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and fused cycloalkanes of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic rings;

[0036] The d1 is selected from 0, 1, 2, 3, 4 or 5; the d2 is selected from 0, 1, 2, 3 or 4; the d3 is selected from 0, 1, 2 or 3; the d4 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the d6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; the d7 is selected from 1, 2, 3, 4 or 5.

[0037] Furthermore, at least one of Ar1, Ar2, and Ar3 is selected from the group shown in Formula 1-a;

[0038] The L1, L2, and L3, whether identical or different, are selected from single bonds or one or a combination of the following groups.

[0039]

[0040] The same or different e are selected from CR1 or N, and at most one e is selected from N;

[0041] The W is selected from O, S, or CR2R3; the Y1 is selected from O, S, or NR5; the Y2 is selected from CR6 or N;

[0042] The R1s, whether identical or different, are selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic groups of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic rings, or adjacent R1s bonded together to form a substituted or unsubstituted ring;

[0043] The same or different R2 and R3 are selected from one of the following: hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, or adjacent R2 and R3 are bonded to form a substituted or unsubstituted ring;

[0044] The R5 is selected from one of the following: substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and fused cycloalkanes of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic rings;

[0045] R6 is selected from one of the following: hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and fused cycloalkanes of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic rings.

[0046] The present invention also provides an organic electroluminescent device, wherein the organic electroluminescent device contains the heterocyclic compound described in the present invention.

[0047] Beneficial Effects: The heterocyclic compound of Formula 1 of this invention has a high glass transition temperature, good film-forming properties, and thermal stability. When used as a capping layer material in organic electroluminescent devices, it can effectively improve light extraction efficiency, thus improving the luminous efficiency and lifespan of the device. Furthermore, the heterocyclic compound of Formula 1 of this invention also possesses high triplet energy levels and high hole mobility. As a hole transport material, it can effectively improve the hole transport efficiency within the device, thereby enhancing the device's performance. Simultaneously, as the P-type host material in the luminescent layer, it can balance electrons and holes within the luminescent layer, widen the exciton recombination region, and improve exciton recombination efficiency, thereby increasing the luminous efficiency and extending the device's lifespan. Detailed Implementation

[0048] 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.

[0049] 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.

[0050] The halogens described in this invention include fluorine, chlorine, bromine, and iodine.

[0051] In this invention, "unsubstituted ZZ group" in "substituted or unsubstituted ZZ group" means that the hydrogen atom of the "ZZ group" is not substituted by a substituent. For example, "unsubstituted aryl group" in "substituted or unsubstituted C6-C60 aryl group" means that the hydrogen atom of the "aryl group" is not substituted by a substituent. And so on.

[0052] In this invention, "CXX~CYY" in "substituted or unsubstituted CXX~CYY ZZ group" represents the number of carbon atoms in the unsubstituted "ZZ group". When the "ZZ group" has a substituent, it does not include the number of carbon atoms in the substituent. For example, in "substituted or unsubstituted C6~C60 aryl group", "C6~C60" represents the number of carbon atoms in the unsubstituted "aryl group". When the "aryl group" has a substituent, it does not include the number of carbon atoms in the substituent. In "fused cycloalcoholic group of substituted or unsubstituted C3~C25 alicyclic ring and C6~C30 aromatic ring", "C3~C25" represents the number of carbon atoms in the unsubstituted "alicyclic ring". When the "alicyclic ring" has a substituent, it does not include the number of carbon atoms in the substituent; "C6~C30" represents the number of carbon atoms in the unsubstituted "aromatic ring". When the "aromatic ring" has a substituent, it does not include the number of carbon atoms in the substituent. And so on.

[0053] 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 Can represent And so on.

[0054] In this invention, when the position of the substituent on the aromatic ring is not fixed, it means that it can be attached to any of the corresponding optional sites on the aromatic ring. For example, Can represent Can represent Can represent And so on.

[0055] In this invention, "forming a ring by bonding two adjacent groups" refers to the formation of a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle by bonding adjacent groups together 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 bonding adjacent groups can be connected to another ring to form a spirostructure. Specific examples are shown below:

[0056]

[0057] 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, benzene, naphthalene, phenanthrene, triphenylene, pyridine, pyrimidine, quinoline, isoquinoline, quinazoline, quinoxaline, fluorene, dibenzofuran, dibenzothiophene, carbazole, etc., but are not limited to these.

[0058] In this invention, "substituted or unsubstituted" means that at least one hydrogen atom on a group is replaced by a substituent. When multiple hydrogen atoms are replaced by multiple substituents, the multiple substituents may be the same or different. The position of the hydrogen atoms replaced by the substituents can be arbitrary. The substituents represented by "substituted or unsubstituted" in the above-mentioned terms include the following groups: deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkoxy groups, substituted or unsubstituted C6-C20 aryloxy groups, substituted or unsubstituted C2-C15 heterocyclic groups, substituted or unsubstituted C1-C15 alkyl groups, substituted or unsubstituted silyl groups, substituted or unsubstituted C3-C15 cycloalkyl groups, substituted or unsubstituted C6-C20 aryl groups, substituted or unsubstituted C2-C20 heteroaryl groups, fused cycloalcoholic groups of substituted or unsubstituted C3-C15 alicyclic and C6-C20 aromatic rings, fused cycloalcoholic groups of substituted or unsubstituted C3-C15 alicyclic and C2-C20 heteroaromatic rings, etc. Preferred groups include: deuterium, tritium, cyano, halogen, nitro, methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, camphenyl, isocamphenyl, fentanyl, silyl, trimethylsilyl, triethylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, phenanthrene, triphenylene, anthracene, pyrene. The substituents include benzo[a]yl, fluoranyl, benzocyclopropane, benzocyclobutane, dihydroindyl, tetrahydronaphthyl, benzocycloheptyl, benzocyclobutenyl, indyl, dihydronaphthyl, fluorenyl, spirodifluorenyl, benzofuranyl, dibenzofuranyl, benzothiopheneyl, dibenzothiopheneyl, indolyl, carbazoleyl, benzodioxonyl, benzodisulfideyl, dihydroisobenzofuranyl, dihydrobenzofuranyl, dihydrobenzothiopheneyl, dihydroisobenzothiopheneyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, etc. Furthermore, each of the above substituents can be substituted or unsubstituted. Two adjacent substituents can bond to form a ring.

[0059] The alkyl group described in this invention refers to a hydrocarbon group formed by removing one hydrogen atom from an alkane molecule. The alkyl group can be a straight-chain alkyl group or a branched alkyl group. When the chain alkyl group described in this invention has three or more carbon atoms, it includes its isomers; for example, propyl includes n-propyl and isopropyl; butyl includes n-butyl, isobutyl, sec-butyl, tert-butyl, and so on. Examples of alkyl groups include, but are not limited to, the following groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, etc., but are not limited thereto. The alkyl group has a carbon number of C1 to C30, preferably C1 to C25, preferably C1 to C20, preferably C1 to C15, and even more preferably C1 to C10.

[0060] The silyl group mentioned in this invention refers to -Si(R) k )3 groups, wherein each R k The same or different groups are selected from the following: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkenyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic rings, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl rings. Preferably, each R k The same or different groups are selected from the following: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl groups, and substituted or unsubstituted C3-C30 cycloalkyl groups. The alkyl group preferably has C1-C20 carbon atoms, more preferably C1-C15, even more preferably C1-C10, and most preferably C1-C8. The cycloalkyl group preferably has C3-C20 carbon atoms, more preferably C3-C15, even more preferably C3-C10, and most preferably C3-C7. Preferably, each R... kThe same or different groups are selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted heptyl, substituted or unsubstituted octyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl. Examples may include, but are not limited to, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, dimethylethylsilyl, dimethylisopropylsilyl, dimethyltert-butylsilyl, tricyclopentylsilyl, tricyclohexylsilyl, triphenylsilyl, triphenylsilyl, tripyridylsilyl, tripyridylsilyl, etc.

[0061] The cycloalkyl group described in this invention refers to a hydrocarbon group formed by removing one hydrogen atom from a cycloalkane molecule. The cycloalkyl group includes monocyclic cycloalkyl, polycyclic cycloalkyl, and bridged cycloalkyl groups. Examples of cycloalkyl groups include, but are not limited to, the following groups: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, camphenyl, fentanyl, isocamphenyl, etc., but are not limited thereto. The cycloalkyl group has 3 to 30 carbon atoms, preferably 3 to 25, preferably 3 to 20, preferably 3 to 15, and more preferably 3 to 10.

[0062] The aryl group referred to in this invention refers to the general term for a monovalent group remaining after removing a hydrogen atom from the aromatic carbon atom of an aromatic compound molecule. The aryl group includes monocyclic aryl, polycyclic aryl, fused-ring aryl, or combinations thereof. Examples of the aryl group include, but are not limited to, the following groups: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracene, triphenylene, fluorene, benzo[a]fluorene, spirodifluorene, spiroanthracenefluorene, pyrene, etc. Aryl, fluoranthyl, etc., but not limited to these. The number of carbon atoms in the aryl group is C6 to C60, preferably C6 to C30, more preferably C6 to C25, and even more preferably C6 to C20.

[0063] The heteroaryl group described in this invention refers to a monovalent group in which at least one carbon atom of an aryl group is replaced by a heteroatom. The heteroatom is selected from O, S, N, Si, B, P, etc., but is not limited thereto. Examples of heteroaryl groups include, but are not limited to, the following groups: benzofuranyl, naphthofuranyl, phenanthrofuranyl, dibenzofuranyl, benzodibenzofuranyl, benzothiophene, naphthothiophene, phenanthiophene, dibenzothiophene, benzodibenzothiophene, indolyl, naphthoindolyl, carbazoyl, benzocarbazoyl, spirofluorenexanthracene, spirofluorenethionanthracene, spirofluoreneazanthracene, dihydrobenzofuranyl, dihydrobenzothiophene, phenoxazinyl, phenthiazinyl, dihydroacridyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, etc., but are not limited thereto. The heteroaryl group has a carbon number of C2 to C60, preferably C2 to C30, more preferably C2 to C25, and even more preferably C3 to C20.

[0064] The fused alicyclic and aromatic ring groups described in this invention refer to the general term for monovalent groups formed by fusion of an alicyclic and an aromatic ring and the removal of one hydrogen atom. Examples of fused alicyclic and aromatic ring groups include, but are not limited to, the following groups: benzocyclopropane, benzocyclobutane, benzocyclobutenyl, dihydroindene, indene, tetrahydronaphthyl, dihydronaphthyl, benzocycloheptane, benzocycloheptenyl, etc., but are not limited thereto. The alicyclic ring has a carbon number of C3 to C30, preferably C3 to C25, preferably C3 to C20, preferably C3 to C15, even more preferably C3 to C10, and more preferably C3 to C8. The aromatic ring has a carbon number of C6 to C60, preferably C6 to C30, preferably C6 to C25, preferably C6 to C18, even more preferably C6 to C12, and more preferably C6 to C10.

[0065] The arylene group referred to in this invention refers to the general term for the divalent group remaining after removing two hydrogen atoms from the aromatic carbon atom of an aromatic compound molecule. The arylene group includes monocyclic arylene, polycyclic arylene, fused-ring arylene, or combinations thereof. Examples of the arylene group include, but are not limited to, the following groups: phenylene, biphenylene, terphenylene, naphthylene, phenanthrene, fluorene, benzo[a]fluorene, dibenzo[a]fluorene, naphthyl[a]fluorene, spirodifluorene, etc., but are not limited thereto. The arylene group has a carbon number of C6 to C30, preferably C6 to C25, more preferably C6 to C20, and more preferably C6 to C18.

[0066] 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 heteroatom is selected from O, S, N, Si, B, P, etc., but is not limited thereto. The heteroaryl group includes monocyclic heteroaryl, polycyclic heteroaryl, fused-ring heteroaryl, or combinations thereof. Examples of the heteroaryl group include, but are not limited to, the following groups: pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, quinazolinyl, naphthidyl, etc., but are not limited thereto. The number of carbon atoms in the heteroaryl group is C2 to C30, preferably C2 to C25, and more preferably C2 to C20.

[0067] The fused alicyclic and aromatic ring groups described in this invention refer to the general term for divalent groups remaining after removing two hydrogen atoms from the fused alicyclic and aromatic rings. Examples of fused alicyclic and aromatic ring groups include, but are not limited to, the following groups: benzo[a]cyclopropane, benzo[a]cyclobutane, dihydroindene, indene, tetrahydronaphthyl, dihydronaphthyl, benzo[a]cycloheptane, benzo[a]cyclobutenyl, benzo[a]cycloheptenyl, etc., but are not limited thereto. The alicyclic ring has 3 to 30 carbon atoms, preferably 3 to 25, preferably 3 to 20, preferably 3 to 15, and even more preferably 3 to 8. The aromatic ring has 6 to 60 carbon atoms, preferably 6 to 30, preferably 6 to 20, preferably 6 to 18, and preferably 6 to 10.

[0068] This invention provides a heterocyclic compound, represented by the following formula 1.

[0069]

[0070] Wherein, the same or different v is selected from CR a Or N, or C atoms bonded to L2 or L3;

[0071] The R a The same or different from one selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, or two adjacent R a Bonding forms substituted or unsubstituted benzene rings, naphthalene rings, anthracene rings, phenanthrene rings, and triphenylene rings;

[0072] The same or different R0s are selected from one of the following: hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, fused cycloalkanes of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic rings, or adjacent R0s bonded to form substituted or unsubstituted aromatic rings;

[0073] The c0 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9;

[0074] The Ar1 is selected from one of the groups shown in formula 1-a or 2-a to 2-m below.

[0075]

[0076] The R 21 The same or different from deuterium, halogen, nitro, trifluoromethyl substituted or unsubstituted silyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, or two adjacent R groups. 21 Bonding forms substituted or unsubstituted alicyclic rings;

[0077] The R 22 The same or different from one of the following: hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, or two adjacent R groups. 22 Bonding forms substituted or unsubstituted aromatic rings;

[0078] The T is selected from O or S;

[0079] The R 23 R 24 The same or different from one of the following: hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, or two adjacent R groups. 23 Two Rs 24 Bonding forms substituted or unsubstituted rings;

[0080] The T0 is selected from O, S, or NR. g The T1 is selected from CR i Or N;

[0081] The u that is the same or different is selected from CR 40 Or N;

[0082] The R 40The same or different from one of the following: hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, or two adjacent R groups. 40 Bonding forms substituted or unsubstituted rings;

[0083] The R i It is selected from one of the following: hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and fused cycloalkanes of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic rings;

[0084] The R d R e The same or different from one selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, or adjacent R d R e Bonding forms substituted or unsubstituted rings;

[0085] The R f R g The same or different from one of the following: substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic fused cycloalcohol;

[0086] The R 41 R 42 The same or different from one of the following: hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic fused cycloalcoholic group;

[0087] a1 is selected from 0, 1, 2, 3, 4, or 5; a2 is selected from 0, 1, 2, 3, or 4; a3 is selected from 0, 1, 2, or 3; a4 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; a5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; a6 is selected from 1, 2, 3, 4, or 5.

[0088] The Ar2 and Ar3 are selected from one of the groups shown in formula 1-a or 1-b to 1-j below.

[0089]

[0090] The R 25 The same or different from deuterium, halogen, nitro, trifluoromethyl, substituted or unsubstituted silyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, or two adjacent R groups. 25 Bonding forms substituted or unsubstituted alicyclic rings;

[0091] The R 26 The same or different from one of the following: hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, or two adjacent R groups. 26 Bonding forms substituted or unsubstituted rings;

[0092] The z that are the same or different are selected from CR 27 Or N; the z1 that is the same as or different from CR is selected. 28 Or N;

[0093] The R 27 R 28 The same or different from one of the following: hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, or two adjacent R groups. 27 Two Rs 28 Bonding forms substituted or unsubstituted rings;

[0094] Q is selected from O, S, and CR. 29 R 30 Q1 is selected from O, S or NR. 31 Q2 is selected from CR 32 Or N;

[0095] The R 29 R 30 The same or different from one selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, or adjacent R 29 R 30 Bonding forms substituted or unsubstituted rings;

[0096] The R 31 It is selected from one of the following: substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and fused cycloalkanes of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic rings;

[0097] The R 32 It is selected from one of the following: hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and fused cycloalkanes of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic rings;

[0098] The d1 is selected from 0, 1, 2, 3, 4 or 5; the d2 is selected from 0, 1, 2, 3 or 4; the d3 is selected from 0, 1, 2 or 3; the d4 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the d6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; the d7 is selected from 1, 2, 3, 4 or 5.

[0099] Furthermore, at least one of Ar1, Ar2, and Ar3 is selected from the group shown in Formula 1-a;

[0100] The L1, L2, and L3, whether identical or different, are selected from single bonds or one or a combination of the following groups.

[0101]

[0102] The same or different e are selected from CR1 or N, and at most one e is selected from N;

[0103] The W is selected from O, S, or CR2R3; the Y1 is selected from O, S, or NR5; the Y2 is selected from CR6 or N;

[0104] The R1s, whether identical or different, are selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic groups of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic rings, or adjacent R1s bonded together to form a substituted or unsubstituted ring;

[0105] The same or different R2 and R3 are selected from one of the following: hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, or adjacent R2 and R3 are bonded to form a substituted or unsubstituted ring;

[0106] The R5 is selected from one of the following: substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and fused cycloalkanes of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic rings;

[0107] R6 is selected from one of the following: hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and fused cycloalkanes of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic rings.

[0108] Preferably, the heterocyclic compound is selected from one of the following formulas 1-1 to 1-5.

[0109]

[0110] Preferably, the Selected from one of the following groups,

[0111]

[0112] The R aThe same or different from one of the following groups selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, or two adjacent R groups. a Bonding forms substituted or unsubstituted benzene rings, naphthalene rings, anthracene rings, phenanthrene rings, and triphenylene rings;

[0113] The n1 is selected from 0, 1, 2 or 3; the n2 is selected from 0, 1 or 2; the n3 is selected from 0, 1, 2, 3, 4 or 5; the n4 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; and the n5 is selected from 0, 1, 2, 3 or 4.

[0114] Preferably, formula 1-a is selected from one of the following groups:

[0115]

[0116] The R0s, whether identical or different, are selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted groups as shown below: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentenyl, benzocyclohexenyl, or adjacent R0s bonded to form a substituted or unsubstituted benzene ring;

[0117] The c0 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; the c1 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the c2 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the c3 is selected from 0, 1, 2, 3, 4, 5 or 6; the c4 is selected from 0, 1, 2, 3, 4 or 5; the c5 is selected from 0, 1, 2 or 3; the c6 is selected from 0, 1, 2, 3 or 4; and the c7 is selected from 0, 1 or 2.

[0118] Preferably, the R0, R aThe "substituted or unsubstituted" substituent is selected from deuterium, cyano, halogen, nitro, and one of the following groups substituted or unsubstituted by one or more deuterium or C1-C6 alkyl groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, trimethylsilyl, triethylsilyl, triisopropylsilyl Alkyl, tri-tert-butylsilyl, triphenylsilyl, ethyl dimethylsilyl, tert-butyl dimethylsilyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzooxazolyl, benzothiazolyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl.

[0119] Preferably, the Ar1 is selected from one of formula 1-a or the following groups.

[0120]

[0121]

[0122] The R k 'The same or different from one of the following groups selected from deuterium, halogen, nitro, trifluoromethyl, substituted or unsubstituted: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl;

[0123] The R k The same or different from one of the following groups selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, triphenyl alkylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, pyridyl, pyrimidinyl, triazineyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, benzothiazolyl, or two adjacent R k Bonding forms substituted or unsubstituted aromatic rings;

[0124] The R k1 The same or different from one of the following groups selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilane alkyl, triphenylsilyl, ethyl dimethylsilyl, tert-butyl dimethylsilyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, benzothiazolyl;

[0125] The b1 is selected from 0, 1, 2, 3, 4, or 5; the b2 is selected from 0, 1, 2, 3, or 4; the b3 is selected from 0, 1, 2, or 3; the b4 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; the b5 is selected from 0, 1, 2, 3, 4, 5, or 6; the b6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; the b7 is selected from 0, 1, or 2; the b8 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the b9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; the b 10 The value is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; the value of b1' is selected from 1, 2, 3, 4 or 5.

[0126] Preferably, the R k R k1 The "substituted or unsubstituted" substituent is selected from deuterium, cyano, halogen, nitro, or one of the following substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl Silyl, triphenylsilyl, ethyl dimethylsilyl, tert-butyl dimethylsilyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzooxazolyl, benzothiazolyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl.

[0127] Preferably, the Selected from one of the following groups,

[0128]

[0129] Preferably, the Ar2 and Ar3 are selected from formula 1-a or one of the following groups.

[0130]

[0131]

[0132] The R q 'The same or different from one of the following groups selected from hydrogen, deuterium, halogen, nitro, trifluoromethyl, substituted or unsubstituted: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl;

[0133] The R q The same or different from one of the following groups selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, triphenyl alkylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, pyridyl, pyrimidinyl, triazineyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, benzothiazolyl, or two adjacent R q Bonding forms substituted or unsubstituted rings;

[0134] The f1 is selected from 0, 1, 2, 3, 4, or 5; the f2 is selected from 0, 1, 2, 3, or 4; the f3 is selected from 0, 1, 2, or 3; the f4 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; the f5 is selected from 0, 1, 2, 3, 4, 5, or 6; the f6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; the f7 is selected from 0, 1, or 2; the f8 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the f9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; the f 10The f1' is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; the f1' is selected from 1, 2, 3, 4 or 5.

[0135] Preferably, the R q The "substituted or unsubstituted" substituent is selected from deuterium, cyano, halogen, nitro, or one of the following substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl Silyl, triphenylsilyl, ethyl dimethylsilyl, tert-butyl dimethylsilyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzooxazolyl, benzothiazolyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl.

[0136] Preferably, the Selected from one of the following groups,

[0137]

[0138] Preferably, L1, L2, and L3, whether the same or different, are selected from single bonds or one or a combination of the following groups:

[0139]

[0140]

[0141] The R 11 The same or different from one of the following groups selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritertyl... Butylsilyl, triphenylsilyl, ethyl dimethylsilyl, tert-butyl dimethylsilyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, pyridyl, quinolinyl, isoquinolinyl, benzoxazolyl, benzothiazolyl, or two adjacent R 11 Bonding forms substituted or unsubstituted rings;

[0142] p1 is selected from 0, 1, 2, 3 or 4; p2 is selected from 0, 1, 2, 3, 4, 5 or 6; p3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; p4 is selected from 0, 1, 2 or 3; p5 is selected from 0, 1 or 2; p6 is selected from 0 or 1; p7 is selected from 0, 1, 2, 3, 4 or 5; p8 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; p9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.

[0143] Preferably, the R 11 The "substituted or unsubstituted" substituent is selected from deuterium, cyano, halogen, nitro, and one of the following substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, trimethylsilyl, triethylsilyl, triisopropylmethyl Silyl, tri-tert-butylsilyl, triphenylsilyl, ethyl dimethylsilyl, tert-butyl dimethylsilyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzooxazolyl, benzothiazolyl, pyridyl, quinolinyl, isoquinolinyl.

[0144] Preferably, the heterocyclic compound is selected from any one of the structures shown below.

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174] The above lists some specific chemical structures of the heterocyclic compounds represented by Formula 1 of the present invention. However, the present invention is not limited to these listed chemical structures. Any structure based on Formula 1 with substituents as defined above should be included.

[0175] In addition, the present invention also provides an organic electroluminescent device containing the heterocyclic compound of the present invention described above.

[0176] Preferably, the organic electroluminescent device includes an anode, a cathode, and an organic layer, wherein the organic layer is located between the cathode and the anode or outside one or more electrodes of the anode and the cathode, and the organic layer contains the heterocyclic compound of the present invention described above.

[0177] Preferably, the organic electroluminescent device includes an anode, a cathode, and an organic layer, the organic layer being located outside one or more electrodes of the anode and the cathode, the organic layer including a capping layer containing the heterocyclic compound of the present invention described above.

[0178] Preferably, the organic electroluminescent device includes an anode, a cathode, and an organic layer, the organic layer being located outside the anode, and the organic layer including a capping layer containing the heterocyclic compound of the present invention described above.

[0179] Preferably, the organic electroluminescent device includes an anode, a cathode, and an organic layer, the organic layer being located outside the cathode, and the organic layer including a capping layer containing the heterocyclic compound of the present invention described above.

[0180] Preferably, the organic electroluminescent device includes an anode, a cathode, and an organic layer, the organic layer being located outside the anode and the cathode, and the organic layer including a capping layer containing the heterocyclic compound of the present invention described above.

[0181] Preferably, the organic electroluminescent device includes an anode, a cathode, and an organic layer, wherein the organic layer is located between the anode and the cathode, and the organic layer includes at least one of a light-emitting layer and a hole transport layer, wherein the at least one of the light-emitting layer and the hole transport layer contains the heterocyclic compound of the present invention described above.

[0182] Preferably, the organic electroluminescent device includes an anode, a cathode, and an organic layer, the organic layer being located between the anode and the cathode, the organic layer including a light-emitting layer, the light-emitting layer containing the heterocyclic compound of the present invention described above.

[0183] Preferably, the organic electroluminescent device includes an anode, a cathode, and an organic layer, the organic layer being located between the anode and the cathode, the organic layer including a light-emitting layer, the light-emitting layer including a host material, the host material containing the heterocyclic compound of the present invention described above.

[0184] Preferably, the organic electroluminescent device includes an anode, a cathode, and an organic layer, the organic layer being located between the anode and the cathode, the organic layer including a light-emitting layer, the light-emitting layer including a host material, the host material including an N-type host material and a P-type host material, the P-type host material containing the heterocyclic compound of the present invention described above.

[0185] Preferably, the organic electroluminescent device includes an anode, a cathode, and an organic layer, the organic layer being located between the anode and the cathode, the organic layer including a hole transport layer containing the heterocyclic compound of the present invention described above.

[0186] Preferably, the organic electroluminescent device includes an anode, a cathode, and an organic layer, the organic layer being located between the anode and the cathode, the organic layer including a hole transport layer, the hole transport layer comprising a first hole transport layer and a second hole transport layer, at least one of the first hole transport layer and the second hole transport layer containing the heterocyclic compound of the present invention described above.

[0187] Preferably, the organic electroluminescent device includes an anode, a cathode, and an organic layer, the organic layer being located between the anode and the cathode, the organic layer including a hole transport layer, the hole transport layer comprising a first hole transport layer and a second hole transport layer, the first hole transport layer containing the heterocyclic compound of the present invention described above.

[0188] Preferably, the organic electroluminescent device includes an anode, a cathode, and an organic layer, the organic layer being located between the anode and the cathode, the organic layer including a hole transport layer, the hole transport layer comprising a first hole transport layer and a second hole transport layer, the second hole transport layer containing the heterocyclic compound of the present invention described above.

[0189] Preferably, the organic electroluminescent device includes an anode, a cathode, and an organic layer, the organic layer being located between the anode and the cathode, the organic layer including a hole transport layer, the hole transport layer comprising a first hole transport layer and a second hole transport layer, the first hole transport layer and the second hole transport layer containing the heterocyclic compound of the present invention described above.

[0190] Preferably, the organic electroluminescent device includes an anode, a cathode, and an organic layer, wherein the organic layer is located between the anode and the cathode, and the organic layer includes a hole transport layer, which comprises a first hole transport layer, a second hole transport layer, and a third hole transport layer, wherein at least one of the first hole transport layer, the second hole transport layer, and the third hole transport layer contains the heterocyclic compound of the present invention described above.

[0191] Preferably, the organic electroluminescent devices of the present invention are divided into single-layer organic electroluminescent devices and multilayer organic electroluminescent devices. The single-layer organic electroluminescent device is an organic electroluminescent device containing one light-emitting unit, and the multilayer organic electroluminescent device is an organic electroluminescent device formed by connecting two or more independent light-emitting units in series through a charge generation layer.

[0192] Preferably, the organic electroluminescent device of the present invention is a single-layer organic electroluminescent device, which includes an anode, a cathode and an organic layer. 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 the heterocyclic compound of the present invention.

[0193] Preferably, the organic electroluminescent device of the present invention is a stacked organic electroluminescent device, which includes an anode, a cathode and an organic layer, wherein the organic layer is located between the anode and the cathode, and the organic layer contains the heterocyclic compound of the present invention.

[0194] The organic functional layer of the organic electroluminescent device of the present invention may include a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, a capping layer, etc. The organic functional layer may be formed by a single-layer structure or by a multi-layer structure with multiple organic layers stacked on top of each other. Each organic functional layer may also contain one or more materials.

[0195] This invention does not particularly limit the materials of the thin films in the organic electroluminescent device; substances known in the art can be used. The organic functional layers of the aforementioned organic electroluminescent device and the electrodes on both sides of the device are described below:

[0196] The anode of the present invention is preferably a material with a high work function, including metal oxides, metals and their alloys, conductive polymers, etc., but not limited thereto. Specific examples may include gold (Au), silver (Ag), indium tin oxide (ITO), zinc oxide (ZnO), indium tin oxide / silver / indium tin oxide (ITO / Ag / ITO), polyaniline, etc., but not limited thereto.

[0197] The hole injection layer described in this invention is preferably made of a material with good hole injection capability, including arylamine derivatives, hexanitrile hexaazabenzophenanthrene compounds, quinacridone compounds, anthraquinone compounds, and polyaniline-based conductive polymers, but not limited thereto. Specific examples may include copper phthalocyanine (CuPc), 4,4',4"-tris(N-(1-naphthyl)-N-phenylamino)triphenylamine (1-TNATA), 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazabenzophenanthrene (HAT-CN), etc., but not limited thereto.

[0198] The hole transport layer of 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, etc. Specific examples may include, but are not limited to, N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), 4,4',4”-tris(carbazole-9-yl)triphenylamine (TCTA), etc. Heterocyclic compounds of this invention are preferred.

[0199] The electron blocking layer described in this invention is preferably made of a material with electron blocking capability and suitable energy level. Electron blocking materials include, but are not limited to, aromatic amine derivatives, carbazole derivatives, etc. Specific examples may include N,N'-bis(naphthyl-1-yl)-N,N'-diphenyl-benzidine (NPD), N,N-bis([1,1'-biphenyl]-4-)-(9H-carbazole-9-yl)-[1,1'-biphenyl]-4-amine, etc., but are not limited to these.

[0200] The luminescent layer of this invention comprises a host material and a guest material. The host material includes, but is not limited to, thiazole derivatives, benzimidazole derivatives, aromatic amine derivatives, carbazole derivatives, etc. Specific examples may include 4,4'-bis(carbazole-9-yl)biphenyl (CBP), 1,3-bis(N-carbazoleyl)benzene (MCP), 1,3,5-tris(carbazole-9-yl)benzene (TCP), etc., but are not limited to these. Heterocyclic compounds are preferred. The heterocyclic compound of this invention can be used alone as a host material or in combination with an N-type host material. When used in combination with an N-type host material, the weight ratio of the heterocyclic compound to the N-type host material is 1:99 to 99:1, preferably 20:80 to 80:20. The guest material includes, but is not limited to, aromatic amine derivatives, boron-containing compounds, metal complexes, etc. Specific examples may include, but are not limited to, tri(2-phenylpyridine)iridium (Ir(ppy)3), di(2-phenylpyridine)(acetylacetone)iridium (Ir(ppy)2(acac)), tri(1-phenyl-isoquinoline)iridium (Ir(piq)3), 2,5,8,11-tetra-tert-butylperylene (TBPe), etc.

[0201] The hole-blocking layer of the present invention is preferably made of a material with hole-blocking capability and suitable energy level. The hole-blocking material includes, but is not limited to, metal complexes, heteroaromatic compounds, etc. Specific examples may include, but are not limited to, bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq) and 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene (TPBi).

[0202] The electron transport layer of the present invention is preferably made of a material with high electron mobility. The electron transport material includes, but is not limited to, phenanthroline derivatives, triazine derivatives, quinoline derivatives, etc. Specific examples may include, but are not limited to, aluminum 8-hydroxyquinoline (Alq3), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), etc.

[0203] The electron injection layer of the present invention is preferably made of a material with good electron injection capability. The electron injection material includes metals, metal compounds, etc., but is not limited thereto. Specific examples may include lithium (Li), lithium fluoride (LiF), lithium 8-hydroxyquinoline (LiQ), lithium oxide (Li2O), etc., but are not limited thereto.

[0204] The cathode of the present invention is preferably made of a material with a low work function. The cathode material includes metals and their alloys, metal oxides, conductive polymers, etc., but is not limited thereto. Specific examples may include aluminum (Al), lithium (Li), magnesium (Mg), magnesium-silver alloy (Mg / Ag), LiF / Al multilayer structure materials, etc., but are not limited thereto.

[0205] The capping material of the present invention is preferably a material with excellent light extraction performance. The capping material includes, but is not limited to, aromatic amine derivatives, metal compounds, carbazole derivatives, etc. Specific examples may include tris(8-hydroxyquinoline)aluminum (Alq3), 4,4'-bis(carbazole-9-yl)biphenyl (CBP), etc., but are not limited to these. Heterocyclic compounds as described in the present invention are preferred.

[0206] There are no particular limitations on the preparation method of each thin film in the organic electroluminescent device of the present invention. Vacuum evaporation, sputtering, spin coating, spraying, screen printing, laser transfer, etc. can be used, but are not limited to these methods.

[0207] The organic electroluminescent device of the present invention is mainly used in panel display, lighting, organic solar cells, organic thin film transistors, flexible OLEDs and other fields, but is not limited thereto.

[0208] The following embodiments illustrate the present invention in more detail; however, the embodiments described below are merely illustrative of this specification, and the scope of this specification is not limited to these embodiments.

[0209] Synthesis Examples

[0210] Raw materials and reagents: This invention does not impose any particular limitations on the raw materials or reagents used in the following synthesis examples. They can be commercially available products or prepared using methods well-known to those skilled in the art. All raw materials and reagents used in this invention are of reagent purity.

[0211] Instruments: G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer (Waters Corporation, UK); Vario ELcube organic elemental analyzer (Elementar Corporation, Germany).

[0212] There are no particular limitations on the preparation method of the heterocyclic compound shown in Formula 1 of this invention, and conventional methods well known to those skilled in the art can be used. For example, carbon-nitrogen coupling reaction, carbon-carbon coupling reaction, etc. The heterocyclic compound shown in Formula 1 of this invention can be prepared using the synthetic route shown below.

[0213] Synthesis Route 1:

[0214]

[0215] Synthesis Route 2: When raw material b is the same as raw material d,

[0216]

[0217] The X n For example, X is a halogen. n The same or different ones are selected from Cl, Br, and I;

[0218] The A is selected from *-B(OH)2 or

[0219] The limitations of Ar1, Ar2, Ar3, L1, L2, L3, and v are the same as those described above.

[0220] The above-mentioned substituents can be bonded by methods known in the art, and the type and position or number of substituents can be changed according to techniques known in the art.

[0221] 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.

[0222] Synthesis Example 1: Preparation of Compound 3

[0223]

[0224] Preparation of intermediate B-3:

[0225] Under nitrogen protection, a-3 (16.25 g, 50.00 mmol), b-3 (19.41 g, 100.00 mmol), and K2CO3 (20.73 g, 150.00 mmol) were dissolved in 600 mL of toluene / ethanol / water (2:1:1). Pd(dppf)Cl2 (0.88 g, 1.20 mmol) was added with stirring, and the mixture was heated under reflux for 6.0 h. After the reaction was complete, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from the resulting solid using toluene / ethanol at an 8:1 ratio to give intermediate B-3 (18.32 g, yield 79%); HPLC purity ≥ 99.85%. Mass spectrometry m / z: 463.2171 (theoretical value: 463.2152).

[0226] Preparation of compound 3:

[0227] Under nitrogen protection, B-3 (13.91 g, 30.00 mmol), c-3 (8.43 g, 30.00 mmol), and sodium tert-butoxide (4.32 g, 45.00 mmol) dissolved in 200 mL of toluene were added to a reaction flask. Pd₂(dba)₃ (0.27 g, 0.30 mmol) and X-Phos (0.29 g, 0.60 mmol) were added with stirring. The mixture of the above reactants was heated under reflux for 5.0 h. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallization from toluene gave compound 3 (14.54 g, 73% yield). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 663.2790 (theoretical value: 663.2778). Theoretical elemental content (%) C 46 H 41 NSi2: C, 83.21; H, 6.22; N, 2.11; Measured elemental content (%): C, 83.23; H, 6.21; N, 2.14.

[0228] Synthesis Example 2: Preparation of Compound 7

[0229]

[0230] According to the preparation method in Example 1, a-3 was replaced with an equimolar amount of a-7, b-3 was replaced with an equimolar amount of b-7, and c-3 was replaced with an equimolar amount of c-7, yielding compound 7 (15.23 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 704.4699 (theoretical value: 704.4684). Theoretical elemental content (%) C 52 D 33N: C, 88.59; H, 9.43; N, 1.99; Measured element content (%): C, 88.56; H, 9.44; N, 1.97.

[0231] Synthesis Example 3: Preparation of Compound 15

[0232]

[0233] According to the preparation method in Example 1, b-3 was replaced with an equimolar amount of b-15 to obtain compound 15 (13.57 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 619.2316 (theoretical value: 619.2300). Theoretical elemental content (%) C 48 H 29 N: C, 93.02; H, 4.72; N, 2.26; Measured element content (%): C, 93.06; H, 4.70; N, 2.23.

[0234] Synthesis Example 4: Preparation of Compound 22

[0235]

[0236] According to the preparation method in Example 1, b-3 was replaced with an equimolar amount of b-22 to obtain compound 22 (17.14 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 771.2914 (theoretical value: 771.2926). Theoretical elemental content (%) C 60 H 37 N: C, 93.35; H, 4.83; N, 1.81; Measured element content (%): C, 93.31; H, 4.84; N, 1.84.

[0237] Synthesis Example 5: Preparation of Compound 44

[0238]

[0239] According to the preparation method in Example 1, b-3 was replaced with an equimolar amount of b-44 to obtain compound 44 (15.77 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 719.2621 (theoretical value: 719.2613). Theoretical elemental content (%) C 56 H 33 N: C, 93.43; H, 4.62; N, 1.95; Measured element content (%): C, 93.47; H, 4.60; N, 1.92.

[0240] Synthesis Example 6: Preparation of Compound 48

[0241]

[0242] According to the preparation method in Example 1, b-3 was replaced with an equimolar amount of b-48 to obtain compound 48 (15.33 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 719.2602 (theoretical value: 719.2613). Theoretical elemental content (%) C 56 H 33 N: C, 93.43; H, 4.62; N, 1.95; Measured element content (%): C, 93.46; H, 4.61; N, 1.91.

[0243] Synthesis Example 7: Preparation of Compound 63

[0244]

[0245] According to the preparation method in Example 1, b-3 was replaced with an equimolar amount of b-63 to obtain compound 63 (16.24 g). HPLC analysis showed a solid purity ≥ 99.91%. Mass spectrometry m / z: 751.3249 (theoretical value: 751.3239). Theoretical elemental content (%) C 58 H 41 N: C, 92.64; H, 5.50; N, 1.86; Measured element content (%): C, 92.66; H, 5.51; N, 1.83.

[0246] Synthesis Example 8: Preparation of Compound 88

[0247]

[0248] According to the preparation method in Example 1, b-3 was replaced with an equimolar amount of b-88 to obtain compound 88 (16.69 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 751.2498 (theoretical value: 751.2511). Theoretical elemental content (%) C 56 H 33 NO2: C, 89.46; H, 4.42; N, 1.86; Measured element content (%): C, 89.44; H, 4.41; N, 1.88.

[0249] Synthesis Example 9: Preparation of Compound 91

[0250]

[0251] According to the preparation method in Example 1, b-3 was replaced with an equimolar amount of b-91 to obtain compound 91 (15.33 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 699.2189 (theoretical value: 699.2198). Theoretical elemental content (%) C 52 H 29 NO2: C, 89.25; H, 4.18; N, 2.00; Measured element content (%): C, 89.26; H, 4.16; N, 2.02.

[0252] Synthesis Example 10: Preparation of Compound 109

[0253]

[0254] According to the preparation method in Example 1, b-3 was replaced with an equimolar amount of b-109 to obtain compound 109 (14.03 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 631.1411 (theoretical value: 631.1428). Theoretical elemental content (%) C 44 H 25 NS2: C, 83.65; H, 3.99; N, 2.22; Measured elemental content (%): C, 83.67; H, 3.98; N, 2.23.

[0255] Synthetic Example 11: Preparation of Compound 138

[0256]

[0257] According to the preparation method in Example 1, b-3 was replaced with an equimolar amount of b-138 to obtain compound 138 (13.18 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 601.1799 (theoretical value: 601.1790). Theoretical elemental content (%) C 42 H 23 N3O2: C, 83.84; H, 3.85; N, 6.98; Measured element content (%): C, 83.86; H, 3.83; N, 6.99.

[0258] Synthesis Example 12: Preparation of Compound 142

[0259]

[0260] According to the preparation method in Example 1, b-3 was replaced with an equimolar amount of b-142 to obtain compound 142 (16.06 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 753.2402 (theoretical value: 753.2416). Theoretical elemental content (%) C54 H 31 N3O2: C, 86.04; H, 4.15; N, 5.57; Measured element content (%): C, 86.07; H, 4.14; N, 5.55.

[0261] Synthetic Example 13: Preparation of Compound 156

[0262]

[0263] According to the preparation method in Example 1, b-3 was replaced with an equimolar amount of b-156 to obtain compound 156 (17.80 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 801.2427 (theoretical value: 801.2416). Theoretical elemental content (%) C 58 H 31 N3O2: C, 86.87; H, 3.90; N, 5.24; Measured element content (%): C, 86.89; H, 3.88; N, 5.26.

[0264] Synthesis Example 14: Preparation of Compound 183

[0265]

[0266] According to the preparation method in Example 1, b-3 was replaced with an equimolar amount of b-183 to obtain compound 183 (15.75 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 699.2187 (theoretical value: 699.2198). Theoretical elemental content (%) C 52 H 29 NO2: C, 89.25; H, 4.18; N, 2.00; Measured element content (%): C, 89.28; H, 4.17; N, 1.98.

[0267] Synthetic Example 15: Preparation of Compound 191

[0268]

[0269] According to the preparation method in Example 1, b-3 was replaced with an equimolar amount of b-191 to obtain compound 191 (17.52 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 799.2520 (theoretical value: 799.2511). Theoretical elemental content (%) C 60 H 33 NO2: C, 90.09; H, 4.16; N, 1.75; Measured element content (%): C, 90.11; H, 4.17; N, 1.73.

[0270] Synthesis Example 16: Preparation of Compound 238

[0271]

[0272] According to the preparation method in Example 1, b-3 was replaced with an equimolar amount of b-238, and c-3 was replaced with an equimolar amount of c-238 to obtain compound 238 (16.11 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 745.2788 (theoretical value: 745.2770). Theoretical elemental content (%) C 58 H 35 N: C, 93.39; H, 4.73; N, 1.88; Measured element content (%): C, 93.37; H, 4.72; N, 1.91.

[0273] Synthesis Example 17: Preparation of Compound 251

[0274]

[0275] According to the preparation method in Synthesis Example 1, b-3 was replaced with an equimolar amount of b-251, and c-3 was replaced with an equimolar amount of c-251 to obtain compound 251 (15.12 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 709.1655 (theoretical value: 709.1646). Theoretical elemental content (%) C 48 H 27 N3S2: C, 81.21; H, 3.83; N, 5.92; Measured element content (%): C, 81.23; H, 3.84; N, 5.91.

[0276] Synthetic Example 18: Preparation of Compound 259

[0277]

[0278] According to the preparation method in Example 1, b-3 was replaced with an equimolar amount of b-259, and c-3 was replaced with an equimolar amount of c-259 to obtain compound 259 (15.21 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 675.2182 (theoretical value: 675.2198). Theoretical elemental content (%) C 50 H 29 NO2: C, 88.87; H, 4.33; N, 2.07; Measured element content (%): C, 88.88; H, 4.32; N, 2.09.

[0279] Synthetic Example 19: Preparation of Compound 351

[0280]

[0281] Preparation of intermediate A-351:

[0282] Under nitrogen protection, a-351 (28.05 g, 100.00 mmol), b-142 (23.90 g, 100.00 mmol), and K2CO3 (27.64 g, 200.00 mmol) were dissolved in 700 mL of toluene / ethanol / water (2:1:1). Pd(PPh3)4 (1.39 g, 1.20 mmol) was added with stirring, and the mixture was heated under reflux for 5.5 h. After the reaction was complete, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from the resulting solid using toluene / ethanol at an 8:1 ratio to give intermediate A-351 (30.80 g, yield 78%); HPLC purity ≥ 99.84%. Mass spectrometry m / z: 394.0893 (theoretical value: 394.0873).

[0283] Preparation of intermediate B-351:

[0284] Under nitrogen protection, A-351 (19.74 g, 50.00 mmol), d-351 (12.75 g, 50.00 mmol), and K2CO3 (13.82 g, 100.00 mmol) were dissolved in 400 mL of toluene / ethanol / water (2:1:1) and Pd(dppf)Cl2 (0.44 g, 0.60 mmol) were added with stirring. The mixture of the above reactants was heated under reflux for 6.0 h. After the reaction was completed, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from the obtained solid with toluene / ethanol = 8:1 to give intermediate B-351 (21.36 g, yield 75%); HPLC purity ≥ 99.87%. Mass spectrometry m / z: 569.1577 (theoretical value: 569.1562).

[0285] Preparation of compound 351

[0286] Under nitrogen protection, B-351 (17.09 g, 30.00 mmol), c-3 (8.43 g, 30.00 mmol), and sodium tert-butoxide (4.32 g, 45.00 mmol) dissolved in 200 mL of toluene were added to a reaction flask with stirring. Pd₂(dba)₃ (0.27 g, 0.30 mmol) and X-Phos (0.29 g, 0.60 mmol) were added, and the mixture was heated under reflux for 6.0 h. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallization from toluene yielded compound 351 (16.63 g, 72% yield). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 769.2198 (theoretical value: 769.2188). Theoretical elemental content (%) C 54 H 31 N3OS: C, 84.24; H, 4.06; N, 5.46; Measured element content (%): C, 84.26; H, 4.07; N, 5.45.

[0287] Synthesis Example 20: Preparation of Compound 367

[0288]

[0289] According to the preparation method in Synthesis Example 19, b-142 was replaced with an equimolar amount of b-367, and d-351 was replaced with an equimolar amount of d-367 to obtain compound 367 (16.03 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 731.1755 (theoretical value: 731.1741). Theoretical elemental content (%) C 52 H 29 NS2: C, 85.33; H, 3.99; N, 1.91; Measured element content (%): C, 85.35; H, 3.98; N, 1.93.

[0290] Synthesis Example 21: Preparation of Compound 379

[0291]

[0292] According to the preparation method in Synthesis Example 19, b-142 was replaced with an equimolar amount of b-379, d-351 was replaced with an equimolar amount of d-379, and c-3 was replaced with an equimolar amount of c-379, yielding compound 379 (17.27 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 777.2478 (theoretical value: 777.2490). Theoretical elemental content (%) C 58 H 35NS: C, 89.54; H, 4.53; N, 1.80; Measured element content (%): C, 89.57; H, 4.52; N, 1.78.

[0293] Synthesis Example 22: Preparation of Compound 388

[0294]

[0295] According to the preparation method in Synthesis Example 19, b-142 was replaced with an equimolar amount of b-388, d-351 was replaced with an equimolar amount of d-388, and c-3 was replaced with an equimolar amount of c-388, yielding compound 388 (17.56 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 812.3432 (theoretical value: 812.3420). Theoretical elemental content (%) C 60 H 32 D7NO2: C, 88.64; H, 5.70; N, 1.72; Measured element content (%): C, 88.67; H, 5.71; N, 1.69.

[0296] Synthesis Example 23: Preparation of Compound 403

[0297]

[0298] According to the preparation method in Example 1, b-3 was replaced with an equimolar amount of b-403, and c-3 was replaced with an equimolar amount of c-403 to obtain compound 403 (15.61 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 693.2469 (theoretical value: 693.2457). Theoretical elemental content (%) C 54 H 31 N: C, 93.48; H, 4.50; N, 2.02; Measured element content (%): C, 93.49; H, 4.48; N, 2.04.

[0299] Synthesis Example 24: Preparation of Compound 420

[0300]

[0301] According to the preparation method in Example 1, b-3 was replaced with an equimolar amount of b-403, and c-3 was replaced with an equimolar amount of c-420, yielding compound 420 (16.59 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 767.2626 (theoretical value: 767.2613). Theoretical elemental content (%) C 60 H 33N: C, 93.84; H, 4.33; N, 1.82; Measured element content (%): C, 93.86; H, 4.31; N, 1.84.

[0302] Synthesis Example 25: Preparation of Compound 443

[0303]

[0304] According to the preparation method in Synthesis Example 1, b-3 was replaced with an equimolar amount of b-403, and c-3 was replaced with an equimolar amount of c-443, yielding compound 443 (18.31 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 835.2860 (theoretical value: 835.2875). Theoretical elemental content (%) C 64 H 37 NO: C, 91.95; H, 4.46; N, 1.68; Measured element content (%): C, 91.97; H, 4.47; N, 1.67.

[0305] Synthesis Example 26: Preparation of Compound 453

[0306]

[0307] According to the preparation method in Example 1, b-3 was replaced with an equimolar amount of b-403, and c-3 was replaced with an equimolar amount of c-453 to obtain compound 453 (19.45 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 875.2811 (theoretical value: 875.2824). Theoretical elemental content (%) C 66 H 37 NO2: C, 90.49; H, 4.26; N, 1.60; Measured element content (%): C, 90.51; H, 4.24; N, 1.63.

[0308] Synthesis Example 27: Preparation of Compound 476

[0309]

[0310] According to the preparation method in Example 1, b-3 was replaced with an equimolar amount of b-403, and c-3 was replaced with an equimolar amount of c-476, yielding compound 476 (16.69 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 761.2478 (theoretical value: 761.2467). Theoretical elemental content (%) C 56 H 31 N3O: C, 88.28; H, 4.10; N, 5.52; Measured element content (%): C, 88.26; H, 4.11; N, 5.54.

[0311] Synthesis Example 28: Preparation of Compound 499

[0312]

[0313] According to the preparation method in Example 1, b-3 was replaced with an equimolar amount of b-403, and c-3 was replaced with an equimolar amount of c-499, yielding compound 499 (16.24 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 751.2347 (theoretical value: 751.2334). Theoretical elemental content (%) C 56 H 33 NS: C, 89.45; H, 4.42; N, 1.86; Measured element content (%): C, 89.48; H, 4.40; N, 1.85.

[0314] Synthesis Example 29: Preparation of Compound 527

[0315]

[0316] According to the preparation method in Example 1, b-3 was replaced with an equimolar amount of b-403, and c-3 was replaced with an equimolar amount of c-527 to obtain compound 527 (17.96 g). HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 808.2888 (theoretical value: 808.2878). Theoretical elemental content (%) C 62 H 36 N2: C, 92.05; H, 4.49; N, 3.46; Measured element content (%): C, 92.07; H, 4.48; N, 3.47.

[0317] Synthesis Example 30: Preparation of Compound 558

[0318]

[0319] According to the preparation method in Example 1, a-3 was replaced with an equimolar amount of a-558, b-3 was replaced with an equimolar amount of b-403, and c-3 was replaced with an equimolar amount of c-558, yielding compound 558 (16.81 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 777.3387 (theoretical value: 777.3396). Theoretical elemental content (%) C 60 H 43 N: C, 92.63; H, 5.57; N, 1.80; Measured element content (%): C, 92.66; H, 5.56; N, 1.78.

[0320] Synthesis Example 31: Preparation of Compound 574

[0321]

[0322] According to the preparation method in Example 1, b-3 was replaced with an equimolar amount of b-403, and c-3 was replaced with an equimolar amount of c-574, yielding compound 574 (17.28 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 767.2601 (theoretical value: 767.2613). Theoretical elemental content (%) C 60 H 33 N: C, 93.84; H, 4.33; N, 1.82; Measured element content (%): C, 93.85; H, 4.31; N, 1.83.

[0323] Synthesis Example 32: Preparation of Compound 652

[0324]

[0325] According to the preparation method in Synthesis Example 19, b-142 was replaced with an equimolar amount of b-403, and d-351 was replaced with an equimolar amount of d-652 to obtain compound 652 (16.41 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 759.2915 (theoretical value: 759.2926). Theoretical elemental content (%) C 59 H 37 N: C, 93.25; H, 4.91; N, 1.84; Measured element content (%): C, 93.28; H, 4.90; N, 1.82.

[0326] Synthesis Example 33: Preparation of Compound 703

[0327]

[0328] According to the preparation method in Synthesis Example 19, b-142 was replaced with an equimolar amount of b-403, d-351 was replaced with an equimolar amount of d-703, and c-3 was replaced with an equimolar amount of c-703, yielding compound 703 (17.72 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 831.2043 (theoretical value: 831.2054). Theoretical elemental content (%) C 60 H 33 NS2: C, 86.61; H, 4.00; N, 1.68; Measured element content (%): C, 86.63; H, 3.98; N, 1.69.

[0329] Synthesis Example 34: Preparation of Compound 716

[0330]

[0331] According to the preparation method in Synthesis Example 19, b-142 was replaced with an equimolar amount of b-403, d-351 was replaced with an equimolar amount of b-142, and c-3 was replaced with an equimolar amount of c-716, yielding compound 716 (15.92 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 757.2682 (theoretical value: 757.2667). Theoretical elemental content (%) C 54 H 27 D4N3O2: C, 85.58; H, 4.65; N, 5.54; Measured element content (%): C, 85.59; H, 4.63; N, 5.56.

[0332] Synthesis Example 35: Preparation of Compound 725

[0333]

[0334] According to the preparation method of Synthesis Example 19, b-142 was replaced with an equimolar amount of b-403, d-351 was replaced with an equimolar amount of b-15, and c-3 was replaced with an equimolar amount of c-725, yielding compound 725 (15.55 g). HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 719.2623 (theoretical value: 719.2613). Theoretical elemental content (%) C 56 H 33 N: C, 93.43; H, 4.62; N, 1.95; Measured element content (%): C, 93.45; H, 4.60; N, 1.91.

[0335] Synthesis Example 36: Preparation of Compound 871

[0336]

[0337] According to the preparation method in Synthesis Example 1, a-3 was replaced with an equimolar amount of a-871, b-3 was replaced with an equimolar amount of b-403, and c-3 was replaced with an equimolar amount of c-871, yielding compound 871 (16.28 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 809.2702 (theoretical value: 809.2719). Theoretical elemental content (%) C 62 H 35 NO: C, 91.94; H, 4.36; N, 1.73; Measured element content (%): C, 91.91; H, 4.40; N, 1.71.

[0338] Synthesis Example 37: Preparation of Compound 872

[0339]

[0340] According to the preparation method in Example 1, a-3 was replaced with an equimolar amount of a-872, and b-3 was replaced with an equimolar amount of b-872, yielding compound 872 (17.14 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 827.2834 (theoretical value: 827.2824). Theoretical elemental content (%) C 62 H 37 NO2: C, 89.94; H, 4.50; N, 1.69; Measured element content (%): C, 89.96; H, 4.47; N, 1.72.

[0341] Synthesis Example 38: Preparation of Compound 893

[0342]

[0343] According to the preparation method in Example 1, a-3 was replaced with an equimolar amount of a-893, and b-3 was replaced with an equimolar amount of b-893, yielding compound 893 (16.26 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 820.2860 (theoretical value: 820.2878). Theoretical elemental content (%) C 63 H 36 N2: C, 92.17; H, 4.42; N, 3.41; Measured element content (%): C, 92.20; H, 4.38; N, 3.43.

[0344] Synthesis Example 39: Preparation of Compound 912

[0345]

[0346] According to the preparation method in Example 1, b-3 was replaced with an equimolar amount of b-912 to obtain compound 912 (18.70 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 853.2717 (theoretical value: 853.2729). Theoretical elemental content (%) C 62 H 35 N3O2: C, 87.20; H, 4.13; N, 4.92; Measured element content (%): C, 87.23; H, 4.12; N, 4.93.

[0347] Synthesis Example 40: Preparation of Compound 914

[0348]

[0349] According to the preparation method in Example 1, a-3 was replaced with an equimolar amount of a-914, and b-3 was replaced with an equimolar amount of b-914 to obtain compound 914 (15.87 g). HPLC analysis showed a solid purity ≥ 99.91%. Mass spectrometry m / z: 755.2336 (theoretical value: 755.2321). Theoretical elemental content (%) C 52 H 29 N5O2: C, 82.63; H, 3.87; N, 9.27; Measured element content (%): C, 82.60; H, 3.90; N, 9.25.

[0350] Device Examples

[0351] In this invention, the ITO glass substrate and the ITO / Ag / ITO glass substrate are 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. They are then ultrasonically cleaned sequentially with acetone and isoacetone for 20 minutes each, and dried at 120°C. All organic materials are sublimated and have a purity of over 99.99%.

[0352] A combined IVL testing system was constructed, consisting of testing software, a computer, a Keithley K2400 digital source meter, and a PhotoResearch PR788 spectrophotometer, to test the driving voltage, luminous efficiency, and CIE color coordinates of organic electroluminescent devices. Lifetime testing was performed using a McScience M6000 OLED lifetime testing system. The testing environment was ambient air at room temperature.

[0353] Example 1: Fabrication of Organic Electroluminescent Device 1

[0354] A hole injection layer with a thickness of 11 nm was vacuum-deposited on the ITO / Ag / ITO anode using a HI-1:HI-2 ratio of 5:95 (wt%). HT-1 was vacuum-deposited on the hole injection layer as a hole transport layer with a thickness of 110 nm. RH-1:RD-1 = 98:2 (wt%) was vacuum-deposited on the hole transport layer to form a light-emitting layer with a thickness of 28 nm. ET-1:LiQ = 1:1 (wt%) was vacuum-deposited on the light-emitting layer as an electron transport layer with a thickness of 32 nm. LiF was vacuum-deposited on the electron transport layer as an electron injection layer with a deposition thickness of 1.0 nm. Mg:Ag = 10:90 (wt%) was vacuum-deposited on the electron injection layer as a cathode with a thickness of 10 nm. Compound 3 of this invention was vacuum-deposited on the cathode as a capping layer with a thickness of 70 nm.

[0355] Examples 2-43: Fabrication of Organic Electroluminescent Devices 2-43

[0356] Replacing compound 3 in the capping layer of Example 1 with compounds 7, 15, 22, 44, 48, 63, 88, 91, 109, 138, 142, 156, 183, 191, 238, 251, 259, 351, 367, 379, 388, 403, 420, 443, 453, 476, 499, 527, 574, 588, 652, 703, 716, 725, 871, 872, 893, 912, and 914 respectively, while following the same other steps, organic electroluminescent devices 2-40 were obtained.

[0357] Comparative Examples 1-2: Fabrication of Comparative Organic Electroluminescent Devices 1-2

[0358] By replacing compound 3 in the capping layer of Example 1 with R-1 and R-2 respectively, and keeping the other steps the same, comparative organic electroluminescent devices 1-2 were obtained.

[0359]

[0360]

[0361] The luminescence characteristics test results of the organic electroluminescent devices prepared in Examples 1-40 and Comparative Examples 1-2 of this invention are shown in Table 1.

[0362] Table 1. Test data on the luminescence characteristics of organic electroluminescent devices.

[0363]

[0364]

[0365] Note: T95 refers to a current density of 10 mA / cm². 2 Under certain conditions, the time it takes for the device's brightness to decay to 95%;

[0366] As can be seen from Table 1, the organic electroluminescent device containing the heterocyclic compound of Formula 1 of the present invention in the capping layer has higher luminous efficiency and longer lifespan compared with the comparative device, and the organic electroluminescent device has better performance.

[0367] Example 41: Fabrication of Organic Electroluminescent Device 41

[0368] A hole injection layer with a thickness of 12 nm was vacuum-deposited on the ITO anode as a HI-1:HI-2 ratio of 5:95 (wt%). A first hole transport layer with a thickness of 80 nm was vacuum-deposited on the hole injection layer as a first hole transport layer. HT-2 was vacuum-deposited on the first hole transport layer as a second hole transport layer with a thickness of 40 nm. A light-emitting layer with a thickness of 32 nm was formed by vacuum-depositing GH-1:compound 3 of this invention:GD-1 ratio of 46:46:8 (wt%) on the second hole transport layer. ET-1 was vacuum-deposited on the light-emitting layer as an electron transport layer with a thickness of 30 nm. LiF was vacuum-deposited on the electron transport layer as an electron injection layer with a deposition thickness of 1.0 nm. Al was vacuum-deposited on the electron injection layer as a cathode with a thickness of 110 nm.

[0369] Examples 42-80: Fabrication of Organic Electroluminescent Devices 42-80

[0370] The compounds in the light-emitting layer of Example 41 were replaced with compounds 7, 15, 22, 44, 48, 63, 88, 91, 109, 138, 142, 156, 183, 191, 238, 251, 259, 351, 367, 379, 388, 403, 420, 443, 453, 476, 499, 527, 574, 588, 652, 703, 716, 725, 871, 872, 893, 912, and 914, respectively, while the other steps remained the same, to obtain organic electroluminescent devices 42-80.

[0371] Comparative Examples 3-6: Fabrication of Comparative Organic Electroluminescent Devices 3-6

[0372] By replacing compound 3 in the light-emitting layer of step 41 with R-3, R-4, R-5, and R-6 respectively, and keeping the other steps the same, comparative organic electroluminescent devices 3 to 6 were obtained.

[0373]

[0374] The luminescence characteristics test results of the organic electroluminescent devices prepared in Examples 41-80 and Comparative Examples 3-6 of this invention are shown in Table 2.

[0375] Table 2. Test data on the luminescence characteristics of organic electroluminescent devices.

[0376]

[0377]

[0378] Note: T97 refers to a current density of 10 mA / cm². 2 Under these conditions, the time it takes for the device's brightness to decay to 97%;

[0379] As can be seen from Table 2, compared with comparative devices 3 to 6, the organic electroluminescent device containing the heterocyclic compound of Formula 1 of the present invention in the light-emitting layer has better device performance, specifically higher luminous efficiency and longer service life.

[0380] Example 81: Fabrication of Organic Electroluminescent Device 81

[0381] A hole injection layer with a thickness of 10 nm was vacuum-deposited on an ITO / Ag / ITO anode using a HI-1:HI-2 ratio of 5:95 (wt%). Compound 3 of this invention was vacuum-deposited on the hole injection layer as a hole transport layer with a thickness of 120 nm. A light-emitting layer with a thickness of 31 nm was formed by vacuum-depositing GH-2:GH-3:GD-2 ratio of 47:47:6 (wt%) on the hole transport layer. ET-2 was vacuum-deposited on the light-emitting layer as an electron transport layer with a thickness of 30 nm. LiF was vacuum-deposited on the electron transport layer as an electron injection layer with a deposition thickness of 1.1 nm. Mg:Ag ratio of 10:90 (wt%) was vacuum-deposited on the electron injection layer as a cathode with a thickness of 10 nm. CP-1 was vacuum-deposited on the cathode as a capping layer with a thickness of 72 nm.

[0382] Examples 82-120: Fabrication of Organic Electroluminescent Devices 82-120

[0383] Replacing compound 3 in the hole transport layer of Example 81 with compounds 7, 15, 22, 44, 48, 63, 88, 91, 109, 138, 142, 156, 183, 191, 238, 251, 259, 351, 367, 379, 388, 403, 420, 443, 453, 476, 499, 527, 574, 588, 652, 703, 716, 725, 871, 872, 893, 912, and 914 respectively, while keeping the other steps the same, organic electroluminescent devices 82-120 are obtained.

[0384] Comparative Examples 7-8: Fabrication of Comparative Organic Electroluminescent Devices 7-8

[0385] By replacing compound 3 in the hole transport layer of Example 81 with R-7 and R-8 respectively, and keeping the other steps the same, comparative organic electroluminescent devices 7-8 were obtained.

[0386]

[0387] The luminescence characteristics test results of the organic electroluminescent devices prepared in Examples 81-120 and Comparative Examples 7-8 of this invention are shown in Table 3.

[0388] Table 3. Test data on the luminescence characteristics of organic electroluminescent devices.

[0389]

[0390]

[0391]

[0392] Note: T97 refers to a current density of 10 mA / cm². 2 Under these conditions, the time it takes for the device's brightness to decay to 97%;

[0393] As can be seen from Table 3, compared with comparative devices 7-8, the organic electroluminescent device containing the heterocyclic compound of Formula 1 of the present invention in the hole transport layer has better performance, exhibiting higher luminous efficiency and longer lifespan. The heterocyclic compound of Formula 1 of the present invention is a good hole transport layer material.

[0394] It should be noted that the present invention has been specifically described with reference to individual embodiments, but those skilled in the art can make various forms or details of improvements to the present invention without departing from the principles of the present invention, and these improvements also fall within the protection scope of the present invention.

Claims

1. A heterocyclic compound, characterized in that, It is represented by the following equation 1, Wherein, the same or different v is selected from CR a Or N, or C atoms bonded to L2 or L3; The R a The same or different from one selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, or two adjacent R a Bonding forms substituted or unsubstituted benzene rings, naphthalene rings, anthracene rings, phenanthrene rings, and triphenylene rings; The same or different R0s are selected from one of the following: hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, fused cycloalkanes of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic rings, or adjacent R0s bonded to form substituted or unsubstituted aromatic rings; The c0 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; The Ar1 is selected from one of the groups shown in formula 1-a or 2-a to 2-m below. The R 21 The same or different from deuterium, halogen, nitro, trifluoromethyl, substituted or unsubstituted silyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, or two adjacent R groups. 21 Bonding forms substituted or unsubstituted alicyclic rings; The R 22 The same or different from one of the following: hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, or two adjacent R groups. 22 Bonding forms substituted or unsubstituted aromatic rings; The T is selected from O or S; The R 23 R 24 The same or different from one of the following: hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, or two adjacent R groups. 23 Two Rs 24 Bonding forms substituted or unsubstituted rings; The T0 is selected from O, S, or NR. g The T1 is selected from CR i Or N; The u that is the same or different is selected from CR 40 Or N; The R 40 The same or different from one of the following: hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, or two adjacent R groups. 40 Bonding forms substituted or unsubstituted rings; The R i It is selected from one of the following: hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and fused cycloalkanes of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic rings; The R d R e The same or different from one selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, or adjacent R d R e Bonding forms substituted or unsubstituted rings; The R f R g The same or different from one of the following: substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic fused cycloalcohol; The R 41 R 42 The same or different from one of the following: hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic fused cycloalcoholic group; a1 is selected from 0, 1, 2, 3, 4, or 5; a2 is selected from 0, 1, 2, 3, or 4; a3 is selected from 0, 1, 2, or 3; a4 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; a5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; a6 is selected from 1, 2, 3, 4, or 5. The Ar2 and Ar3 are selected from one of the groups shown in formula 1-a or 1-b to 1-j below. The R 25 The same or different from deuterium, halogen, nitro, trifluoromethyl, substituted or unsubstituted silyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, or two adjacent R groups. 25 Bonding forms substituted or unsubstituted alicyclic rings; The R 26 The same or different from one of the following: hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, or two adjacent R groups. 26 Bonding forms substituted or unsubstituted rings; The z that are the same or different are selected from CR 27 Or N; the z1 that is the same as or different from CR is selected. 28 Or N; The R 27 R 28 The same or different from one of the following: hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, or two adjacent R groups. 27 Two Rs 28 Bonding forms substituted or unsubstituted rings; Q is selected from O, S, and CR. 29 R 30 Q1 is selected from O, S or NR. 31 Q2 is selected from CR 32 Or N; The R 29 R 30 The same or different from one selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, or adjacent R 29 R 30 Bonding forms substituted or unsubstituted rings; The R 31 It is selected from one of the following: substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and fused cycloalkanes of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic rings; The R 32 It is selected from one of the following: hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and fused cycloalkanes of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic rings; The d1 is selected from 0, 1, 2, 3, 4 or 5; the d2 is selected from 0, 1, 2, 3 or 4; the d3 is selected from 0, 1, 2 or 3; the d4 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the d6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; the d7 is selected from 1, 2, 3, 4 or 5. Furthermore, at least one of Ar1, Ar2, and Ar3 is selected from the group shown in Formula 1-a; The L1, L2, and L3, whether identical or different, are selected from single bonds or one or a combination of the following groups. The same or different e are selected from CR1 or N, and at most one e is selected from N; The W is selected from O, S, or CR2R3; the Y1 is selected from O, S, or NR5; the Y2 is selected from CR6 or N; The R1s, whether identical or different, are selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic groups of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic rings, or adjacent R1s bonded together to form a substituted or unsubstituted ring; The same or different R2 and R3 are selected from one of the following: hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, or adjacent R2 and R3 are bonded to form a substituted or unsubstituted ring; The R5 is selected from one of the following: substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and fused cycloalkanes of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic rings; R6 is selected from one of the following: hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and fused cycloalkanes of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic rings.

2. The heterocyclic compound according to claim 1, characterized in that, The heterocyclic compound is selected from one of the following formulas: 1-1 to 1-5.

3. The heterocyclic compound according to claim 1, characterized in that, The Selected from one of the following groups, The R a The same or different from one of the following groups selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, or two adjacent R groups. a Bonding forms substituted or unsubstituted benzene rings, naphthalene rings, anthracene rings, phenanthrene rings, and triphenylene rings; The n1 is selected from 0, 1, 2 or 3; the n2 is selected from 0, 1 or 2; the n3 is selected from 0, 1, 2, 3, 4 or 5; the n4 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; and the n5 is selected from 0, 1, 2, 3 or 4.

4. The heterocyclic compound according to claim 1, characterized in that, The Ar1 is selected from one of formula 1-a or the following groups. The R k 'The same or different from one of the following groups selected from deuterium, halogen, nitro, trifluoromethyl, substituted or unsubstituted: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl; The R k The same or different from one of the following groups selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, triphenyl alkylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, pyridyl, pyrimidinyl, triazineyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, benzothiazolyl, or two adjacent R k Bonding forms substituted or unsubstituted aromatic rings; The R k1 The same or different from one of the following groups selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilane alkyl, triphenylsilyl, ethyl dimethylsilyl, tert-butyl dimethylsilyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, benzothiazolyl; The b1 is selected from 0, 1, 2, 3, 4, or 5; the b2 is selected from 0, 1, 2, 3, or 4; the b3 is selected from 0, 1, 2, or 3; the b4 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; the b5 is selected from 0, 1, 2, 3, 4, 5, or 6; the b6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; the b7 is selected from 0, 1, or 2; the b8 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the b9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; the b 10 The value is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; the value of b1' is selected from 1, 2, 3, 4 or 5.

5. The heterocyclic compound according to claim 1, characterized in that, The Ar2 and Ar3 are selected from one of formula 1-a or the following groups. The R q 'The same or different from one of the following groups selected from deuterium, halogen, nitro, trifluoromethyl, substituted or unsubstituted: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl; The R q The same or different from one of the following groups selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, triphenyl alkylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, pyridyl, pyrimidinyl, triazineyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, benzothiazolyl, or two adjacent R q Bonding forms substituted or unsubstituted rings; The f1 is selected from 0, 1, 2, 3, 4, or 5; the f2 is selected from 0, 1, 2, 3, or 4; the f3 is selected from 0, 1, 2, or 3; the f4 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; the f5 is selected from 0, 1, 2, 3, 4, 5, or 6; the f6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; the f7 is selected from 0, 1, or 2; the f8 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the f9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; the f 10 The f1' is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; the f1' is selected from 1, 2, 3, 4 or 5.

6. The heterocyclic compound according to claim 1, characterized in that, The L1, L2, and L3, whether identical or different, are selected from single bonds or one or a combination of the following groups. The R 11 The same or different from one of the following groups selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritertyl... Butylsilyl, triphenylsilyl, ethyl dimethylsilyl, tert-butyl dimethylsilyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, pyridyl, quinolinyl, isoquinolinyl, benzoxazolyl, benzothiazolyl, or two adjacent R 11 Bonding forms substituted or unsubstituted rings; p1 is selected from 0, 1, 2, 3 or 4; p2 is selected from 0, 1, 2, 3, 4, 5 or 6; p3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; p4 is selected from 0, 1, 2 or 3; p5 is selected from 0, 1 or 2; p6 is selected from 0 or 1; p7 is selected from 0, 1, 2, 3, 4 or 5; p8 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; p9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.

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 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 a heterocyclic compound as described in any one of claims 1 to 7.

9. The organic electroluminescent device according to claim 8, characterized in that, The organic electroluminescent device includes an anode, a cathode, and an organic layer, the organic layer being located outside one or more electrodes of the anode and the cathode, the organic layer including a capping layer containing a heterocyclic compound as described in any one of claims 1 to 7.

10. The organic electroluminescent device according to claim 8, characterized in that, The organic electroluminescent device includes an anode, a cathode, and an organic layer, wherein the organic layer is located between the anode and the cathode, and the organic layer includes at least one of a light-emitting layer and a hole transport layer, wherein at least one of the light-emitting layer and the hole transport layer contains a heterocyclic compound as described in any one of claims 1 to 7.

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