A pyrene compound and an organic electroluminescence device thereof

Abstract

The application discloses a pyrene compound and an organic electroluminescent device thereof, and relates to the technical field of organic electroluminescent devices.The organic luminescent device disclosed by the application innovatively adopts a pyrene derivative compound with a specific characteristic structure as a main body material of a light-emitting layer.The material design effectively adjusts the charge transport balance in the device, thereby significantly optimizing the light-emitting performance of the device and greatly prolonging the service life.Based on this, the application successfully prepares an organic luminescent device with dual excellent characteristics of long service life and high efficiency, and the comprehensive index of the device can perfectly adapt to various high-end display products such as flat panel displays, flexible folding terminals and wearable electronic devices.

Description

Technical Field

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

[0002] OLED, or Organic Light-Emitting Diode, is a display technology based on the self-emissive properties of organic materials, eliminating the need for a backlight and liquid crystal molecules. With its core advantages such as self-emission, high contrast, thinness, flexibility, and low blue light, it has penetrated multiple fields including consumer electronics, automotive, professional displays, and the Internet of Things.

[0003] OLEDs typically consist of a substrate, an anode, an organic layer (including a hole transport layer, an electron transport layer, and an emissive layer), and a cathode. Electrons are injected through the cathode, and holes are injected through the anode. These electrons and holes recombine in the organic layer, exciting organic molecules to form excitons. When these excitons transition from a high-energy state to a low-energy state, they release photons, thus emitting light. The emissive layer is the core functional layer of an OLED, directly determining the screen's luminous efficiency, color performance, lifespan, and power consumption; it is crucial for achieving the "self-emissive" characteristic.

[0004] OLED emissive layer materials are centered around a "host-doped" structure. The host material, with its wide bandgap, high carrier mobility, and good thermal stability, plays a crucial role in capturing and transporting carriers, stabilizing excitons, and preventing the aggregation and quenching of guest materials. It is a vital foundation for ensuring efficient light emission from doped materials and adapting to the needs of various display scenarios. Therefore, developing high-performance OLED host materials is of paramount importance for further optimizing the overall performance of the emissive layer, overcoming core performance bottlenecks in OLED devices, and expanding their practical value in various application fields. Summary of the Invention

[0005] Purpose of the invention: In view of the above problems, the purpose of this invention is to provide a pyrene compound and its organic electroluminescent device, so as to improve the luminous efficiency of the organic electroluminescent device and extend its service life.

[0006] This invention provides a pyrene compound, wherein the pyrene compound is selected from the structure shown in Formula 1:

[0007] In Equation 1, each of the n is independently selected from N or CRn, and the n connected to L1 is selected from C; Each of the Rn groups is independently selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C24 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C30 Any one of the following: aryl, substituted or unsubstituted C2-C30 heteroaryl, fused ring of substituted or unsubstituted C3-C20 aliphatic ring and C6-C30 aromatic ring, fused ring of substituted or unsubstituted C3-C20 aliphatic ring and C2-C30 heteroaromatic ring, when two or more Rn are present at the same time, the two or more Rn are the same or different, and adjacent two Rn can be connected to form a substituted or unsubstituted ring; And at least one Rn is not selected from H; The L1 is selected from any one of the following: a single bond, a substituted or unsubstituted C6-C30 arylene, a substituted or unsubstituted C2-C30 heteroarylene, a fused cycloalcoholic group of a substituted or unsubstituted C3-C20 aliphatic ring and a C6-C30 heteroarylene ring, or a fused cycloalcoholic group of a substituted or unsubstituted C3-C20 aliphatic ring and a C2-C30 heteroarylene ring; The m1 is selected from 0, 1, 2, 3, 4 or 5; The Ar is selected from the group shown in Formula A or the group shown in Formula B; The rings A1 and A2 are each independently selected from one of the following: a substituted or unsubstituted C6-C30 aromatic ring, a substituted or unsubstituted C2-C30 heteroaromatic ring, or a ring formed by fusion of a substituted or unsubstituted C3-C20 aliphatic ring and a C6-C30 aromatic ring. X1 is selected from O or S; X2 is selected from O, S or CR6R7; The Y is selected from O, S, or CR6R7; R6 and R7 are each independently selected from any one of hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 aliphatic ring and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C20 aliphatic ring and C2-C30 heteroaromatic ring, or R6 and R7 are interconnected to form substituted or unsubstituted rings.

[0008] Beneficial effects

[0009] Compared with existing technologies, the compounds described in this invention can be used as materials for various organic functional layers of organic light-emitting devices, thereby improving device efficiency, reducing driving voltage, and extending lifespan. Specifically, they can be used as hole injection, hole transport, electron blocking, light emission, hole blocking, electron transport, or electron injection materials. Crucially, the organic light-emitting device of this invention uses pyrene-derived compounds with characteristic structures as the main material of the light-emitting layer, which can significantly optimize the light-emitting performance and lifespan of the device, and prepare organic light-emitting devices with both long lifespan and high efficiency, suitable for various display devices such as flat panels, flexible displays, and wearable displays. Detailed Implementation

[0010] The technical solution will be clearly and completely described below with reference to embodiments of the present invention. It should be understood that the described embodiments are only a part of the present invention and do not cover all aspects of the present invention. After reading this invention, any equivalent modifications and variations made by those skilled in the art should fall within the protection scope defined by this invention.

[0011] In the compounds of this invention, " "This refers to the portion that is connected to another substituent." "It can be connected to any optional position of the group / fragment to which it is connected."

[0012] In the compounds of this invention, any atom not specified as a particular isotope contains any stable isotope of that atom, and contains atoms at both their natural and non-natural isotopic abundances. Taking hydrogen as an example, each hydrogen atom in all naturally occurring compounds contains about 0.0156 atomic percent deuterium.

[0013] In this invention, the use of "H" and "hydrogen atom" refers to the presence of no more than the natural abundance of deuterium or tritium atoms in the chemical structure, for example, no more than 0.0156 atomic% of deuterium. "D" and "deuterium atom" refer to a deuterium abundance greater than the natural abundance, for example, any value exceeding 0.1 atomic%, 1 atomic%, or 10 atomic%, such as approximately 95 atomic% of deuterium. "T" and "tritium atom" refer to a tritium abundance greater than the natural abundance, for example, any value exceeding 0.1 atomic%, 1 atomic%, or 10 atomic%, such as approximately 95% of tritium. In this invention, the omission of undrawn hydrogen atoms signifies "H" or "hydrogen atom".

[0014] The halogens described in this invention include F, Cl, Br, and I.

[0015] In this invention, "substituted or unsubstituted" means unsubstituted or substituted by one or more substituents selected from the group consisting of: deuterium, halogen, amino, cyano, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 cycloalkenyl, substituted or unsubstituted C3-C30 heterocyclic alkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C2-C60 heteroaryl, substituted or unsubstituted silyl, preferably deuterium, halogen, cyano, nitro, C1-C12 alkyl, C3-C12 cycloalkyl, ... Alkyl, C3-C12 cycloalkenyl, C3-C12 heterocycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, substituted or unsubstituted silyl, wherein, when substituted by multiple substituents, the multiple substituents are the same or different from each other; preferably, it means unsubstituted or substituted by one or more substituents selected from the group consisting of: deuterium, fluorine, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, deuterated ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, deuterated tert-butyl, cyclopropane, methyl-substituted cyclopropane, ethyl-substituted cyclopropane, deuterated cyclopropane, cyclobutane, methyl-substituted cyclobutane, ethyl-substituted cyclopropane Butyl, deuterated cyclobutyl, cyclopentyl, methyl-substituted cyclopentyl, ethyl-substituted cyclopentyl, deuterated cyclopentyl, cyclohexyl, methyl-substituted cyclohexyl, ethyl-substituted cyclohexyl, n-propyl-substituted cyclohexyl, n-butyl-substituted cyclohexyl, cyclohexane-substituted cyclohexyl, deuterated cyclohexyl, cycloheptyl, cyclopentenyl, methyl-substituted cyclopentenyl, ethyl-substituted cyclopentenyl, cyclohexenyl, cycloheptenyl, adamantyl, methyl-substituted adamantyl, ethyl-substituted adamantyl, deuterated adamantyl, norbornyl, methyl-substituted norbornyl, ethyl-substituted norbornyl, deuterated norbornyl, tetrahydropyrrolyl, piperidinyl, morpholinyl, thiomorpholine The following substituents are used: methyl-substituted piperazine, ethyl-substituted piperazine, phenyl-substituted piperazine, naphthyl-substituted piperazine, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, anthracene, deuterated anthracene, phenanthrene, deuterated phenanthrene, triphenylene, pyrene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-adamantyl-fluorenyl, spiro-cyclopentenyl-fluorenyl, spiro-cyclohexenyl-fluorenyl, N-phenylcarbazolyl, dibenzofuranyl, dibenzothiopheneyl, trimethylsilyl, triphenylsilyl. When substituted with multiple substituents, the multiple substituents may be the same or different from each other; in addition, adjacent substituents may also be linked to form a ring.

[0016] The alkyl group described in this invention refers to a monovalent group formed by removing one hydrogen atom from an alkane molecule. The alkyl group can be a straight-chain alkyl group or a branched-chain alkyl group. When the number of carbon atoms in the chain alkyl group described in this invention is 3 or more, it includes its isomers. For example, propyl includes n-propyl and isopropyl; butyl includes n-butyl, isobutyl, sec-butyl, tert-butyl, and so on. The number of carbon atoms in the alkyl group is C1 to C24, preferably C1 to C20, more preferably C1 to C10, and most preferably C1 to C6. Examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, etc., but are not limited to the above list.

[0017] The silyl group referred to in this invention is a -Si(R)3 group, wherein each R is the same or different and is selected from any of the following groups: hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C6-C30 aromatic ring, and substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C2-C30 heteroaromatic ring. Preferably, each R is the same or different and is selected from the following groups: hydrogen, deuterium, halogen, nitro, or substituted or unsubstituted of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, isobutyl, sec-butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, cyclopropyl, cyclobutyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, vinyl, propenyl, 1,3-butadienyl, ethynyl, 1-propynyl, 2-butynyl, methoxy, ethoxy, propoxy, phenoxy, 1-naphthoxy, 9-anthraoxy, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, tetrahydronaphthyl. Examples include, but are not limited to, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, dimethylethylsilyl, dimethylisopropylsilyl, dimethyltert-butylsilyl, tricyclopentylsilyl, tricyclohexylsilyl, triphenylsilyl, triphenylsilyl, tripyridylsilyl, and tripyridylsilyl.

[0018] The cycloalkyl group described in this invention refers to a monovalent group formed by removing one hydrogen atom from a cyclic alkane molecule, preferably with a carbon number of C3 to C20, more preferably C3 to C12, and most preferably C3 to C7. Examples include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornene, etc., but are not limited to the above-listed groups.

[0019] The alkoxy group described in this invention is represented by -O-alkyl. Examples and preferred examples of alkyl groups are the same as those described above. It can be a straight-chain alkoxy group, preferably with 1 to 20 carbon atoms, more preferably with 1 to 12 carbon atoms, and most preferably with 1 to 6 carbon atoms. Examples include methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, etc., but are not limited to the above-listed examples.

[0020] The alkenyl group described in this invention refers to a monovalent group remaining after removing one hydrogen atom from an olefin molecule. It can be a straight-chain alkenyl or a branched alkenyl, preferably with C2 to C20 carbon atoms, more preferably C1 to C12, and most preferably C2 to C6. Examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, styryl, etc., but are not limited to the above-listed groups.

[0021] The alkynyl group mentioned in this invention refers to a monovalent group in an alkyne molecule after removing one hydrogen atom. It can be a straight-chain alkynyl group or a branched-chain alkynyl group, preferably with C2 to C20 carbon atoms, more preferably with C1 to C12 carbon atoms, and most preferably with C2 to C6 carbon atoms. Examples include ethynyl, 1-propynyl, 1-butynyl, 1-pentynyl, 1-hexynyl, 1-heptyynyl, 1-octyynyl, 1-nonynyl, 1-decynyl, 2-butynyl, 3-methyl-1-butynyl, 4-methyl-2-pentynyl, phenylethynyl, 1-phenyl-2-propynyl, 3-phenyl-1-propynyl, 2-naphthylethynyl, 1-naphthylethynyl, diphenylethynyl, 1-benzocyclobutenylethynyl, 2-biphenylethynyl, 9-phenanthylethynyl, 2-anthraylethynyl, 2-thienylethynyl, 3-pyridylethynyl, 2-furanylethynyl, etc., but not limited to the above-listed examples.

[0022] The aryloxy group described in this invention is represented by -O-aryl. The aromatic hydrocarbon portion of the aryloxy group includes monocyclic aromatic hydrocarbons, polycyclic aromatic hydrocarbons, fused-ring aromatic hydrocarbons, and heterocyclic aromatic hydrocarbons, etc., preferably with a carbon number of C6 to C30, more preferably C6 to C20, and most preferably C6 to C12. Examples include phenoxy, methylphenoxy, ethylphenoxy, methoxyphenoxy, ethoxyphenoxy, biphenoxy, naphthoxy, anthraquinoxaloxy, phenanthoxy, furanoxaloxy, thiophenoxy, pyridinoxaloxy, quinolinoxaloxy, benzofuranoxaloxy, benzothiophenoxaloxy, benzyloxy, phenylethoxy, phenylpropoxy, phenylbutoxy, naphthylmethyloxy, anthraquinoxaloxy, methylbenzyloxy, methoxybenzyloxy, chlorobenzyloxy, nitrobenzyloxy, etc., but are not limited to the above-listed examples.

[0023] The aryl group described in this invention refers to the group formed by removing one hydrogen atom from the aromatic carbon atom in an aromatic hydrocarbon molecule. It can be a monocyclic aryl or a fused-ring aryl. Preferably, the number of carbon atoms is C6 to C30, more preferably C6 to C18, and most preferably C6 to C12. Examples include phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, pyrene, thionyl, triphenylene, perylene, fluorene, benzo[a]fluorene, spirodifluorene, fluoranyl, etc., but are not limited to the above-listed groups.

[0024] The heteroaryl group described in this invention refers to a group formed by replacing one or more aromatic nucleus carbon atoms in an aryl group with heteroatoms (such as O, S, N, Si, or P). It can be a monocyclic heteroaryl or a fused-ring heteroaryl. Preferably, the number of carbon atoms is C2-C30, more preferably C2-C18, particularly preferably C2-C15, and most preferably C2-C12. Examples include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thiopheneyl, pyrroleyl, oxazolyl, thiazolyl, imidazolyl, bipyridyl, bipyrimidinyl, phenylpyridyl, phenylpyrimidinyl, quinolinyl, isoquinolinyl, benzo[a]quinolinyl, benzo[a]isoquinolinyl, quinazolinyl, quinoxolinyl, benzo[a]quinoxolinyl, benzo[a]quinoxolinyl, o-phenanthrolinel, naphridyl, indoleyl, benzo[a]thiopheneyl, benzo[a]furanyl, N-hexabenzothiopheneyl, N-hexabenzofuranyl, benzyl The compounds include, but are not limited to, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, N-hexabenzofuranyl, benzodibenzofuranyl, dibenzothiophenyl, N-hexabenzothiophenyl, benzodibenzothiophenyl, dibenzoxazolyl, dibenzoimidazolyl, dibenzothiazolyl, carbazoleyl, N-hexacarbazoleyl, benzocarbazoleyl, acridineyl, 9,10-dihydroacridyl, phenoxazinyl, phenthiazinyl, phenoxazinyl, spirofluorenexanthyl, spirofluorenethionthanthyl, etc.

[0025] The fused alicyclic and aromatic ring group described in this invention refers to a monovalent group formed by removing one hydrogen atom after the alicyclic and aromatic rings are fused. The alicyclic ring preferably has 3-20 carbon atoms, more preferably 3-15, and most preferably 3-8. The aromatic ring preferably has 6-30 carbon atoms, more preferably 6-20, more preferably 6-18, and most preferably 6-10. Examples include benzocyclopropane, benzocyclobutane, benzocyclopentane, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, benzocycloheptane, benzocycloheptenyl, naphthocyclopropyl, naphthocyclobutyl, naphthocyclopentyl, naphthocyclohexyl, etc., but are not limited to the above-listed groups.

[0026] The fused alicyclic and heteroaromatic ring group described in this invention refers to a monovalent group formed by removing one hydrogen atom after the alicyclic and heteroaromatic rings are fused. The alicyclic ring preferably has 3-20 carbon atoms, more preferably 3-15, and most preferably 3-8. The heteroaromatic ring preferably has 2-30 carbon atoms, more preferably 2-18, particularly preferably 2-15, and most preferably 2-12. Examples include, but not limited to, dibenzofuranocyclopropyl, dibenzofuranocyclobutyl, dibenzofuranocyclopentyl, dibenzofuranocyclohexyl, dibenzofuranocycloheptyl, dibenzothiophenecyclopropyl, dibenzothiophenecyclobutyl, dibenzothiophenecyclopentyl, dibenzothiophenecyclohexyl, dibenzothiophenecycloheptyl, carbazocyclopropyl, carbazocyclobutyl, carbazocyclopentyl, carbazocyclohexyl, carbazocycloheptyl, indolecyclobutyl, indolecyclopentyl, indolecyclohexyl, indolecycloheptyl, pyridinocyclopropyl, pyridinocyclobutyl, pyridinocyclopentyl, pyridinocyclohexyl, pyridinobenzocycloheptyl, pyrimidinocyclopropyl, pyrimidinocyclobutyl, pyrimidinocyclopentyl, pyrimidinocyclohexyl, pyrimidinobenzocycloheptyl, etc.

[0027] The alicyclic group described in this invention refers to aliphatic hydrocarbons with 3 to 20 carbon atoms, which can be completely unsaturated or partially unsaturated. Examples include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, and cycloheptene, but are not limited to the above list. Multiple monocyclic hydrocarbons can also be linked in various ways: two rings in the molecule can share a single carbon atom to form a spirocyclic ring; two carbon atoms on a ring can be connected by a carbon bridge to form a bridged ring; several rings can also be interconnected to form a cage-like structure, such as adamantane, norbornane, camphene, etc., but are not limited to the above list.

[0028] The amine group described in this invention refers to a monovalent or polyvalent group formed by removing one or more hydrogen atoms from an ammonia molecule. It can be a primary amine group (-NH2), a secondary amine group (-NHR), or a tertiary amine group (-NR2), wherein R is independently hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, or substituted or unsubstituted... The group comprises any one of the following: an alkenyl group (C2-C20), a substituted or unsubstituted alkynyl group (C2-C20), a substituted or unsubstituted aryl group (C6-C30), a substituted or unsubstituted aryl group (C6-C30), a substituted or unsubstituted heteroaryl group (C2-C30), a substituted or unsubstituted amino group, a fused cycloalcoholic group (C3-C20 alicyclic ring and C6-C30 aromatic ring), or a fused cycloalcoholic group (C3-C20 alicyclic ring and C2-C30 heteroaryl ring). Preferably, each R is the same or different and is selected from the following groups: hydrogen, deuterium, tritium, or substituted or unsubstituted groups of the following: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, tetrahydronaphthyl. Specific examples may include, but are not limited to, amino, methylamino, dimethylamino, ethylamino, di-n-propylamino, methylethylamino, n-propylamino, isopropylamino, n-butylamino, tert-butylamino, isobutylamino, sec-butylamino, n-pentylamino, n-hexylamino, cyclohexylamino, benzylamino, aniline, diphenylamino, tert-butylphenylamino, pyridineamino, phenylpyridineamino, dipyridineamino, pyrimidineamino, and dipyrimidineamino.

[0029] In the compounds of 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 on the rings. For example, Can represent or ; Can represent , , And so on.

[0030] In the compounds of this invention, when the position of the substituent or linking site on the ring is not fixed, it means that it can be linked to any of the optional sites on the ring. For example, Can represent , , ; Can represent , , ; Can represent , , , , , , , , , , And so on.

[0031] In this invention, "the formation of a ring by bonding two adjacent groups" refers to the formation of a substituted or unsubstituted hydrocarbon ring by bonding adjacent groups together and optionally aromatizing them. The hydrocarbon ring can be an aromatic hydrocarbon ring. The hydrocarbon ring can be a monocyclic or polycyclic group. Examples are shown below:

[0032] Furthermore, a ring formed by the bonding of adjacent groups can connect with another ring to form a helical structure. See the example below:

[0033] 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, spirorings, etc., such as cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, benzene, naphthalene, phenanthrene, triphenylene, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, fluorene, etc., but are not limited to these.

[0034] This invention provides a pyrene compound, wherein the pyrene compound is selected from the structure shown in Formula 1:

[0035] In Equation 1, each of the n is independently selected from N or CRn, and the n connected to L1 is selected from C; Each of the Rn groups is independently selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C24 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C30 Any one of the following: aryl, substituted or unsubstituted C2-C30 heteroaryl, fused ring of substituted or unsubstituted C3-C20 aliphatic ring and C6-C30 aromatic ring, fused ring of substituted or unsubstituted C3-C20 aliphatic ring and C2-C30 heteroaromatic ring, when two or more Rn are present at the same time, the two or more Rn are the same or different, and adjacent two Rn can be connected to form a substituted or unsubstituted ring; And at least one Rn is not selected from H; The L1 is selected from any one of the following: a single bond, a substituted or unsubstituted C6-C30 arylene, a substituted or unsubstituted C2-C30 heteroarylene, a fused cycloalcoholic group of a substituted or unsubstituted C3-C20 aliphatic ring and a C6-C30 heteroarylene ring, or a fused cycloalcoholic group of a substituted or unsubstituted C3-C20 aliphatic ring and a C2-C30 heteroarylene ring; The m1 is selected from 0, 1, 2, 3, 4 or 5; The Ar is selected from the group shown in Formula A or the group shown in Formula B; The rings A1 and A2 are each independently selected from one of the following: a substituted or unsubstituted C6-C30 aromatic ring, a substituted or unsubstituted C2-C30 heteroaromatic ring, or a ring formed by fusion of a substituted or unsubstituted C3-C20 aliphatic ring and a C6-C30 aromatic ring. X1 is selected from O or S; X2 is selected from O, S or CR6R7; The Y is selected from O, S, or CR6R7; R6 and R7 are each independently selected from any one of hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 aliphatic ring and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C20 aliphatic ring and C2-C30 heteroaromatic ring, or R6 and R7 are interconnected to form substituted or unsubstituted rings.

[0036] Preferably, at most three, two, or one of the n are selected from N.

[0037] Preferably, "at least one Rn" includes one, two, three, four or more Rn.

[0038] Preferably, Rn is independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted groups of the following: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, formula A, formula B, or any one of the following groups:

[0039] The n1 is selected from 0, 1, 2, 3, 4, or 5; the n2 is selected from 0, 1, 2, 3, or 4; the n3 is selected from 0, 1, 2, or 3; the n4 is selected from 0, 1, or 2; the n5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; the n6 is selected from 0, 1, 2, 3, 4, 5, or 6; the n7 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; the n8 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; the n9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; and the n10 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. The L is selected from any one of the following: a single bond, a substituted or unsubstituted C6-C30 arylene, a substituted or unsubstituted C2-C30 heteroarylene, a fused cycloalcoholic group of a substituted or unsubstituted C3-C20 aliphatic ring and a C6-C30 heteroarylene ring, or a fused cycloalcoholic group of a substituted or unsubstituted C3-C20 aliphatic ring and a C2-C30 heteroarylene ring; R10, R11, R12, R13, Ra, Rt, and Rj are each independently selected from any one of hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C6-C30 aromatic ring, and substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C2-C30 heteroaromatic ring.

[0040] More preferably, at least one (one, two, three, four or more) Rn is selected from any one of substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, fused cycloalcoholic groups of substituted or unsubstituted C3-C20 aliphatic rings and C6-C30 aromatic rings, and fused cycloalcoholic groups of substituted or unsubstituted C3-C20 aliphatic rings and C2-C30 heteroaromatic rings.

[0041] Particularly preferred, at least one (one, two, three, four or more) Rn is selected from formula A, formula B or any of the following groups: .

[0042] Preferably, the substituents in Rn that are "substituted or unsubstituted" are selected from: deuterium, cyano, nitro, halogen atom, hydroxyl, trifluoromethyl, methyl, ethyl, propyl, butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, norbornyl, adamantyl, phenyl, biphenyl, terphenyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, naphthyl, anthracene, phenanthrene, phenylenetriene, etc. 9,9-Dimethylfluorenyl, 9,9-Diphenylfluorenyl, 9-Methyl-9-phenylfluorenyl, furanyl, benzofuranyl, dibenzofuranyl, thiopheneyl, benzothiopheneyl, dibenzothiopheneyl, pyridyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, deuterated methyl, deuterated ethyl, deuterated propyl, deuterated butyl, deuterated adamantyl, deuterated norbornel, methyl-substituted adamantyl, ethyl-substituted adamantyl, methyl-substituted norbornel The following are listed: trimethylsilyl, triethylsilyl, ethyl dimethylsilyl, triisopropylsilyl, propyl dimethylsilyl, tri-tert-butylsilyl, tert-butyl dimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyl dimethylsilyl, and those with deuterium, cyano, nitro, halogen atom, trifluoromethyl, methyl, ethyl, propyl, butyl, deuterated methyl, deuterated ethyl, deuterated propyl, deuterated butyl, cyclopropyl One or more substituted phenyl groups from the group consisting of alkyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, norbornelyl, and adamantyl; biphenyl, terphenyl, naphthyl, anthraceneyl, phenanthryl, triphenylene, furanyl, benzofuranyl, dibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, pyridyl, pyrazinyl, pyridazinyl, quinolinyl, and isoquinolinyl; in the case of being substituted by multiple substituents, the multiple substituents may be the same as or different from each other.

[0043] Preferably, Formula 1 is selected from any of the following structures:

[0044] The value of i is selected from 0, 1, 2, 3, 4 or 5; The value of j is selected from 0, 1, 2, 3 or 4; p is selected from 0, 1, 2, or 3; The q is selected from 0, 1, or 2; The definitions of Rn, L1, m1, X1, X2, Y, ring A1, and ring A2 are the same as those in the compound of formula 1.

[0045] Preferably, Formula 1 is selected from any of the following structures:

[0046] The value of i is selected from 0, 1, 2, 3, 4 or 5; The value of j is selected from 0, 1, 2, 3 or 4; p is selected from 0, 1, 2, or 3; The q is selected from 0, 1, or 2; The definitions of Rn, L1, m1, ring A1, and ring A2 are the same as those in the compound of Formula 1.

[0047] Preferably, formulas A and B are each independently selected from any one of the following groups:

[0048] a' is selected from 0, 1, 2, 3, 4, 5, 6, or 7; b' is selected from 0, 1, 2, 3, 4, 5, or 6; c' is selected from 0, 1, 2, 3, 4, or 5; d' is selected from 0, 1, 2, 3, or 4; e' is selected from 0, 1, 2, or 3; f' is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; R8 and R9 are each independently selected from any one of hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, substituted or unsubstituted C2-C30 fused cycloalcoholic group of aliphatic ring and C6-C30 aromatic ring, substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C2-C30 heteroaromatic ring, or R8 and R9 are interconnected to form substituted or unsubstituted rings; The definitions of R6 and R7 are the same as those in the compound of Formula 1.

[0049] Preferably, each L1 is independently selected from a single bond or any one of the following groups:

[0050] Each u is independently selected from CRu or N, and at least one u is not selected from N; Each Ru is independently selected from any one of hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkoxy, substituted or unsubstituted C6-C30 aryl, 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, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaryl ring, or substituted or unsubstituted Ru are connected to form substituted or unsubstituted rings; The ring C is selected from substituted or unsubstituted C3~C20 alicyclic rings; U1 is selected from O, S, or NR1; The U2 is selected from N or CR2; The V is selected from single bond, O, S, CR3R4, NR5, SiR3R4, GeR3R4, or Se; The W is selected from O, S, CR3R4, NR5, SiR3R4, GeR3R4, or Se; R1, R2, R3, R4, and R5 are each independently selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6 Any one of the following: ~C30 aryloxy group, substituted or unsubstituted C6~C30 aryl group, substituted or unsubstituted C2~C30 heteroaryl group, substituted or unsubstituted amino group, fused cycloalcoholic group of substituted or unsubstituted C3~C20 alicyclic group and C6~C30 aromatic group, fused cycloalcoholic group of substituted or unsubstituted C3~C20 alicyclic group and C2~C30 heteroaromatic group, or R3 and R4 connected to form a substituted or unsubstituted ring.

[0051] More preferably, each of the L1 groups is independently selected from a single bond or any one of the following groups:

[0052] The 'a' is selected from 0, 1, 2, 3, or 4; the 'b' is selected from 0, 1, 2, 3, 4, 5, or 6; the 'c' is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the 'd' is selected from 0, 1, 2, 3, 4, 5, 6, or 7; the 'e' is selected from 0, 1, 2, or 3; the 'f' is selected from 0, 1, 2, 3, 4, or 5; the 'g' is selected from 0, 1, or 2; the 'h' is selected from 0 or 1; and the 'k' is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. Each of the Rc groups is independently selected from any one of the following: hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted amino, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaryl ring. The definitions of Ru, Ri, R1, R2, R3, R4, and R5 are the same as those in the compounds of Formula 1.

[0053] Most preferably, the compound of formula 1 is selected from any one of the following structures: 。

[0054] The above lists some specific structural forms of pyrene compounds represented by Chemical Formula 1 according to the present invention. However, the present invention is not limited to these listed chemical structures. Any structure based on the structure shown in Chemical Formula 1, with substituents as defined above, should be included.

[0055] The present invention provides an organic electroluminescent device, wherein the organic electroluminescent device comprises one or more of the pyrene compounds described in the present invention.

[0056] Preferably, the organic electroluminescent device includes an anode, a cathode, and an organic functional layer. The organic functional layer includes one or more of the following: a hole transport region, a light-emitting layer, an electron transport region, and a capping layer on the side of the cathode away from the anode. The organic layer contains one or more of the pyrene compounds described in this invention.

[0057] Preferably, the organic electroluminescent device includes an anode, a cathode, and an organic functional layer. The organic layer is located between the anode and the cathode in a hole transport region, a light-emitting layer, and an electron transport region. The light-emitting layer contains one or more of the pyrene compounds described in this invention.

[0058] More preferably, the light-emitting layer comprises a host material and a guest material, wherein the host material comprises one or more of the pyrene compounds described in this invention.

[0059] 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 layers and electrodes on both sides of the aforementioned organic electroluminescent device are described below: The anode of this invention is preferably a high work function material with low sheet resistance, high transmittance, and good stability. Specific examples of anode materials in this invention include: metals, such as magnesium, silver, aluminum, copper, zinc, and gold, or alloys thereof; metal oxides, such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides, such as molybdenum oxide-silver-molybdenum oxide (MoO3-Ag-MoO3) or aluminum-nickel-molybdenum oxide (Al / Ni / MoO3); conductive polymers, such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, polythiophene derivatives, and polyaniline, but not limited thereto.

[0060] The hole injection layer described in this invention is preferably made of a highly conductive material with good film-forming properties and high chemical stability. Specific examples include, but are not limited to, aromatic amine derivatives, metalloporphyrins, oligothiophene, molybdenum hexacyanohexaazabenzophenanthrene oxide (HAT-CN), and molybdenum trioxide (MoO3).

[0061] The hole transport layer described in this invention is preferably made of materials with high hole mobility and high thermal stability. Most are aromatic polyamine compounds, specific examples of which include: N,N'-diphenyl-N,N'-di(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB), N,N'-di(1-naphthyl)-N,N'-diphenyl-1,1'-biphenyl-4,4'-diamine (α-NPD), etc. Polymers such as poly(N-vinylcarbazole) (PVK) and poly(4-vinyltriphenylamine) (PVTPA) can also be used, but are not limited to these.

[0062] The electron blocking layer of this invention is preferably made of materials with high hole mobility and extremely low electron mobility. Specific examples include: carbazole derivatives, such as 4,4'-bis(9-carbazole)biphenyl (CBP), 1,3-bis(9-carbazole)benzene (mCP), and 3,3'-bis(9-carbazole)biphenyl (mCBP); spirofluorene derivatives, such as N-([1,1'-diphenyl]-4-yl)-N-(9,9-dimethyl-9H-furan-2-yl)-9,9'-spirodifluorene-2-amine, etc., but are not limited thereto.

[0063] The light-emitting layer of the present invention comprises a host material and a dopant material. The host material may comprise a single host material or a dual host material, and the guest material may be a simple fluorescent material or a phosphorescent material, or a combination of fluorescent and phosphorescent materials. The main material of the luminescent layer can be selected from 4,4'-bis(9-carbazole)biphenyl (CBP), 9,10-bis(2-naphthyl)anthracene (ADN), 4,4-bis(9-carbazole)biphenyl (CPB), 9,9'-(1,3-phenyl)bis-9H-carbazole (mCP), 4,4',4”-tris(carbazole-9-yl)triphenylamine (TCTA), 9,10-bis(1-naphthyl)anthracene (α-ADN), N,N'-bis-(1-naphthyl)-N,N'-diphenyl-[1,1':4',1”:4”,1”'-tetraphenyl]-4,4”'-diamino (4PNPB), 1,3,5-tris(9-carbazole)benzene (TCP), pyrene compounds described in this invention, etc., but is not limited thereto.

[0064] Doping materials can be polycyclic aromatic hydrocarbon derivatives or styrene-based derivatives. Specific examples include 4,4'-bis(2,2'-diphenylvinyl)biphenyl (DPVBi) and 4,4'-bis[4-(diphenylamino)styrene]biphenyl (BDAVBi). Phosphorescent materials are mainly complexes containing heavy metals (such as iridium, platinum, etc.). Specific examples include tris(2-phenylpyridine)iridium (Ir(ppy)3), tris(1-phenylisoquinoline)iridium (Ir(piq)3), bis(2-benzo[b]thiophene-2-ylpyridine)acetylacetone iridium (Ir(bt)2(acac)), etc., but are not limited to these.

[0065] The hole blocking layer described in this invention is preferably made of materials with high electron mobility and extremely low hole mobility. Specific examples include: nitrogen-containing heterocyclic compounds, such as 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene (TPBi), 4,7-diphenyl-1,10-phenanthroline (Bphen), 1,3-bis(4-(pyridin-3-yl)phenyl)benzene (mCPy), 1,3,5-tris(4-(3-pyridinyl)phenyl)benzene (TmPyPB); metal complexes, such as tris(8-hydroxyquinoline)aluminum (Alq3), lithium 8-hydroxyquinoline (Liq), etc., but are not limited thereto.

[0066] The electron transport layer described in this invention is preferably made of materials with high electron mobility and high triplet energy. Specific examples include: metal complexes, such as Alq3, BAlq, and LiQ; nitrogen-containing heterocyclic derivatives, such as 1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi), 4,7-diphenyl-1,10-phenanthroline (BPhen), etc., but are not limited thereto.

[0067] The electron injection layer described in this invention is preferably made of a material with strong electron injection capability and low work function. Specific examples include: alkali metals, such as lithium (Li) and cesium (Cs); alkaline earth metals, such as magnesium (Mg) and calcium (Ca); alkali metal oxides, such as lithium fluoride (LiF) and cesium carbonate (Cs₂CO₃); organoalkali metal complexes, such as lithium 8-hydroxyquinoline (Liq), etc., but are not limited thereto.

[0068] The cathode of this invention is preferably made of a low work function material with high conductivity and good stability. Specific examples include: low work function metals, such as aluminum (Al), magnesium (Mg), calcium (Ca), and silver (Ag); alloys, such as Mg:Ag alloy and Li:Al alloy; multilayer structure materials, such as lithium fluoride (LiF), lithium oxide (Li2O), and magnesium oxide (MgO); and doped composite materials, such as indium tin oxide (ITO) and 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB), but are not limited thereto.

[0069] The organic layer of the aforementioned organic electroluminescent device can be obtained through vacuum evaporation, sputtering, spin coating, spraying, screen printing, laser transfer, etc., but is not limited to these methods.

[0070] The fabrication of the above-described organic electroluminescent device is specifically described in the following embodiments. However, the following embodiments are merely illustrative of this specification, and the scope of this specification is not limited to these embodiments.

[0071] The technical solutions and effects of the present invention will be further described below with reference to embodiments and comparative examples.

[0072] The present invention does not impose any particular restrictions on the source of raw materials used in the following embodiments, which can be commercially available products or prepared using preparation methods well known to those skilled in the art.

[0073] The mass spectrometry of the compounds in this invention was performed using a G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer from Waters Instruments, UK, with chloroform as the solvent. Elemental analysis was performed using a VarioELcube organic elemental analyzer from Elementar GmbH, Germany, with sample masses ranging from 5 to 10 mg.

[0074] Synthesis Example 1: Synthesis of Intermediate E-218

[0075] Under nitrogen protection, e-218 (81.83 g, 225 mmol), B-283 (57.63 g, 225 mmol), K2CO3 (62.19 g, 450 mmol), Pd(PPh3)4 (2.60 g, 2.25 mmol), and 750 mL of toluene / ethanol / water (2:1:1) were added to a reaction flask. The mixture was stirred under reflux for 5.5 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from the resulting solid using toluene / ethanol in an 8:1 ratio to obtain intermediate E-218 (83.55 g, 75%). HPLC analysis showed that the purity of the solid was ≥99.86%. Mass spectrometry m / z: 494.1846 (theoretical value: 494.1835).

[0076] Synthesis Example 2: Synthesis of Intermediate E-546

[0077] Preparation of intermediate e'-546: Under a nitrogen atmosphere, e-546 (93.98 g, 310 mmol), pinacol diboronate (78.72 g, 310 mmol), and K₂CO₃ (60.85 g, 620 mmol) were added sequentially to a reaction flask. Then, 1500 mL of DMF was added, and after purging the air three times with nitrogen, Pd(dppf)Cl₂ (2.53 g, 3.1 mmol) was added. The reaction system was heated and stirred, and refluxed for 6 h. After the reaction was complete, the mixture was cooled to room temperature, distilled water was added, and the mixture was extracted with ethyl acetate (800 mL × 3 times). The organic phase was separated, dried over anhydrous magnesium sulfate, and then rotary evaporated under reduced pressure to obtain the crude product. The obtained solid was purified by recrystallization from n-hexane:ethyl acetate in an 8:1 ratio to obtain intermediate e'-546 (87.95 g, 81%); HPLC purity ≥ 99.87%. Mass spectrometry m / z: 350.1135 (theoretical value: 350.1148).

[0078] Preparation of intermediate E-546: Under nitrogen protection, e'-546 (78.80 g, 225 mmol), b-546 (60.20 g, 225 mmol), K2CO3 (62.19 g, 450 mmol), Pd(PPh3)4 (2.60 g, 2.25 mmol), and 750 mL of toluene / ethanol / water (2:1:1) were added to a reaction flask. The mixture was stirred under reflux for 5.5 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from the resulting solid using toluene / ethanol in an 8:1 ratio to obtain intermediate E-546 (65.64 g, 71%). HPLC analysis showed that the purity of the solid was ≥99.88%. Mass spectrometry m / z: 410.0546 (theoretical value: 410.0532).

[0079] Synthesis Example 3: Synthesis of Intermediate E-565

[0080] Following the preparation method of Synthesis Example 2, e-546 was replaced with an equimolar amount of e-565, and b-546 was replaced with an equimolar amount of b-565 to obtain compound 52 (57.15 g), with an HPLC purity ≥ 99.84%. Mass spectrometry m / z: 362.0659 (theoretical value: 362.0644).

[0081] Synthesis Example 4: Synthesis of Intermediate E-588

[0082] Preparation of intermediate B'-588: Under nitrogen protection, b-588 (69.21 g, 225 mmol), b'-588 (38.70 g, 225 mmol), K2CO3 (62.19 g, 450 mmol), Pd(PPh3)4 (2.60 g, 2.25 mmol), and 750 mL of toluene / ethanol / water (2:1:1) were added to a reaction flask. The mixture was stirred under reflux for 5.5 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from the resulting solid using toluene / ethanol in an 8:1 ratio to obtain intermediate B'-588 (59.89 g, 75%). HPLC analysis showed that the purity of the solid was ≥99.87%. Mass spectrometry m / z: 354.1161 (theoretical value: 354.1175).

[0083] Preparation of intermediate B-588: Under a nitrogen atmosphere, B'-588 (53.23 g, 150 mmol), pinacol diboronate (38.09 g, 150 mmol), and K2CO3 (41.46 g, 300 mmol) were added sequentially to a reaction flask. Then, 1000 mL of DMF was added, and after purging the air three times with nitrogen, Pd(dppf)Cl2 (1.22 g, 1.50 mmol) was added. The reaction system was heated and stirred, and refluxed for 6 h. After the reaction was complete, the mixture was cooled to room temperature, distilled water was added, and the mixture was extracted with ethyl acetate (800 mL × 3 times). The organic phase was separated, dried over anhydrous magnesium sulfate, and then rotary evaporated under reduced pressure to obtain the crude product. The obtained solid was purified by recrystallization from n-hexane:ethyl acetate in an 8:1 ratio to obtain intermediate B-588 (48.21 g, 72%); HPLC purity ≥ 99.88%. Mass spectrometry m / z: 446.2431 (theoretical value: 446.2417).

[0084] Synthesis Example 5: Synthesis of Intermediate E-597

[0085] Following the preparation method of Synthesis Example 2, e-546 was replaced with an equimolar amount of e-597, and b-546 was replaced with an equimolar amount of b-597 to obtain compound 52 (59.75 g), with an HPLC purity ≥ 99.84%. Mass spectrometry m / z: 384.0929 (theoretical value: 384.0917).

[0086] Synthesis Example 6: Synthesis of Compound 1

[0087] Preparation of intermediate C-1: Under nitrogen protection, A-1 (31.56 g, 100 mmol), B-1 (12.19 g, 100 mmol), K₂CO₃ (20.73 g, 150 mmol), Pd(PPh₃)₄ (1.16 g, 1 mmol), toluene (450 ml), ethanol (100 ml), and water (100 ml) were added to a reaction flask, and the mixture was reacted under reflux for 8 hours. After the reaction was completed, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic phase was washed with water, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The mixture was then subjected to silica gel column chromatography (petroleum ether: dichloromethane = 6:1) to give intermediate C-1 (23.77 g, 76%). The purity of the solid was ≥99.78% as determined by HPLC. Mass spectrometry m / z: 312.0721 (theoretical value: 312.0706).

[0088] Preparation of intermediate D-1: Under a nitrogen atmosphere, C-1 (15.64 g, 50 mmol), pinacol diborate (12.70 g, 50 mmol), and potassium acetate (9.81 g, 100 mmol) were added sequentially to the reaction flask. Then, 300 mL of DMF was added, and after purging the air three times with nitrogen, Pd(dppf)Cl2 (0.41 g, 0.5 mmol) was added. The reaction system was heated and stirred, and refluxed for 6 h. After the reaction was complete, the mixture was cooled to room temperature, distilled water was added, and the mixture was extracted with ethyl acetate (800 mL × 3 times). The organic phase was separated, dried over anhydrous magnesium sulfate, and then rotary evaporated under reduced pressure to obtain the crude product. The obtained solid was purified by recrystallization from n-hexane:ethyl acetate in an 8:1 ratio to give intermediate D-1 (16.37 g, 81%); HPLC purity ≥ 99.87%. Mass spectrometry m / z: 404.1932 (theoretical value: 404.1948).

[0089] Preparation of compound 1: Under nitrogen protection, D-1 (4.04 g, 10 mmol), E-1 (3.19 g, 10 mmol), K3PO4 (4.25 g, 20 mmol), Pd(OAc)2 (0.04 g, 0.20 mmol), X-Phos (0.19 g, 0.40 mmol), toluene (100 ml), and water (5 ml) were added to a reaction flask, and the mixture was reacted under reflux for 12 hours. After the reaction was completed, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic phase was washed with water, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The mixture was then subjected to silica gel column chromatography (n-hexane:ethyl acetate = 6:1) to give compound 1 (4.13 g, 80%). The purity of the solid was ≥99.94% as determined by HPLC. Mass spectrometry m / z: 516.1019 (theoretical value: 516.1006). Theoretical elemental content (%) C 36 H20 S2: C, 83.69; H, 3.90; Actual element content (%): C, 83.68; H, 3.92.

[0090] Synthesis Example 7: Synthesis of Compound 58

[0091] Following the preparation method of Synthesis Example 6, A-1 was replaced with an equimolar amount of A-58, and E-1 was replaced with an equimolar amount of E-58, yielding compound 58 (3.85 g) with an HPLC purity ≥ 99.95%. Mass spectrometry m / z: 500.1248 (theoretical value: 500.1235). Theoretical elemental content (%) C 36 H 20 OS: C, 86.37; H, 4.03; Actual element content (%): C, 86.35; H, 4.05.

[0092] Synthesis Example 8: Synthesis of Compound 60

[0093] Following the preparation method of Synthesis Example 6, A-1 was replaced with an equimolar amount of A-60, and E-1 was replaced with an equimolar amount of E-60, yielding compound 60 (4.06 g) with an HPLC purity ≥ 99.93%. Mass spectrometry m / z: 548.3271 (theoretical value: 548.3257). Theoretical elemental content (%) C 42 H 20 D 12 : C, 91.92; H, 8.08; Actual element content (%): C, 91.94; H, 8.06.

[0094] Synthesis Example 9: Synthesis of Compound 132

[0095] Following the preparation method of Synthesis Example 6, A-1 was replaced with an equimolar amount of A-60, B-1 with an equimolar amount of B-132, and E-1 with an equimolar amount of E-132, yielding compound 132 (4.38 g) with an HPLC purity ≥ 99.96%. Mass spectrometry m / z: 607.2935 (theoretical value: 607.2923). Theoretical elemental content (%) C 46 H 29 D5O: C, 90.90; H, 6.47; Actual element content (%): C, 90.92; H, 6.46.

[0096] Synthesis Example 10: Synthesis of Compound 155

[0097] Following the preparation method of Synthesis Example 6, A-1 was replaced with an equimolar amount of A-60, and B-1 was replaced with an equimolar amount of B-155, yielding compound 155 (4.35 g) with an HPLC purity ≥ 99.94%. Mass spectrometry m / z: 572.1644 (theoretical value: 572.1632). Theoretical elemental content (%) C 40 H 28 S2: C, 83.88; H, 4.93; Actual element content (%): C, 83.87; H, 4.95.

[0098] Synthesis Example 11: Synthesis of Compound 198

[0099] Following the preparation method of Synthesis Example 6, B-1 was replaced with an equimolar amount of B-198 to obtain compound 198 (5.22 g), with an HPLC purity ≥ 99.97%. Mass spectrometry m / z: 668.1645 (theoretical value: 668.1632). Theoretical elemental content (%) C 48 H 28 S2: C, 86.19; H, 4.22; Actual element content (%): C, 86.17; H, 4.23.

[0100] Synthesis Example 12: Synthesis of Compound 218

[0101] Following the preparation method of Synthesis Example 6, A-1 was replaced with an equimolar amount of A-218, B-1 with an equimolar amount of B-218, and E-1 with an equimolar amount of E-218, yielding compound 218 (6.10 g) with an HPLC purity ≥ 99.93%. Mass spectrometry m / z: 812.3463 (theoretical value: 812.3477). Theoretical elemental content (%) C 61 H 48 S: C, 90.11; H, 5.95; Actual element content (%): C, 90.13; H, 5.94.

[0102] Synthesis Example 13: Synthesis of Compound 232

[0103] Following the preparation method of Synthesis Example 6, B-1 was replaced with an equimolar amount of B-232, and E-1 was replaced with an equimolar amount of E-232, yielding compound 232 (6.12 g) with an HPLC purity ≥ 99.94%. Mass spectrometry m / z: 794.3381 (theoretical value: 794.3369). Theoretical elemental content (%) C 60 H 46 Si: C, 90.64; H, 5.83; Actual element content (%): C, 90.65; H, 5.84.

[0104] Synthesis Example 14: Synthesis of Compound 240

[0105] Following the preparation method of Synthesis Example 6, B-1 was replaced with an equimolar amount of B-240, and E-1 was replaced with an equimolar amount of E-240, yielding compound 240 (4.40 g) with an HPLC purity ≥ 99.98%. Mass spectrometry m / z: 556.1874 (theoretical value: 556.1859). Theoretical elemental content (%) C 39 H 28 O2Si: C, 84.14; H, 5.07; Actual element content (%): C, 84.15; H, 5.06.

[0106] Synthesis Example 15: Synthesis of Compound 283

[0107] Following the preparation method of Synthesis Example 6, B-1 was replaced with an equimolar amount of B-283, and E-1 was replaced with an equimolar amount of E-283, yielding compound 283 (5.02 g) with an HPLC purity ≥ 99.92%. Mass spectrometry m / z: 660.2863 (theoretical value: 660.2851). Theoretical elemental content (%) C 49 H 40 S: C, 89.05; H, 6.10; Actual element content (%): C, 89.03; H, 6.11.

[0108] Synthesis Example 16: Synthesis of Compound 294

[0109] Following the preparation method of Synthesis Example 6, A-1 was replaced with an equimolar amount of A-218, B-1 with an equimolar amount of B-283, and E-1 with an equimolar amount of E-294, yielding compound 294 (4.63 g) with an HPLC purity ≥ 99.95%. Mass spectrometry m / z: 634.2342 (theoretical value: 634.2330). Theoretical elemental content (%) C46 H 34 OS: C, 87.03; H, 5.40; Actual element content (%): C, 87.02; H, 5.41.

[0110] Synthesis Example 17: Synthesis of Compound 332

[0111] Following the preparation method of Synthesis Example 6, A-1 was replaced with an equimolar amount of A-60, B-1 with an equimolar amount of B-332, and E-1 with an equimolar amount of E-332, yielding compound 332 (4.69 g) with an HPLC purity ≥ 99.97%. Mass spectrometry m / z: 616.1848 (theoretical value: 616.1861). Theoretical elemental content (%) C 45 H 28 OS: C, 87.63; H, 4.58; Actual element content (%): C, 87.64; H, 4.57.

[0112] Synthesis Example 18: Synthesis of Compound 339

[0113] Following the preparation method of Synthesis Example 6, B-1 was replaced with an equimolar amount of B-339, and E-1 was replaced with an equimolar amount of E-339, yielding compound 339 (6.09 g) with an HPLC purity ≥ 99.94%. Mass spectrometry m / z: 790.3249 (theoretical value: 790.3236). Theoretical elemental content (%) C 61 H 42 O: C, 92.63; H, 5.35; Actual element content (%): C, 92.64; H, 5.34.

[0114] Synthesis Example 19: Synthesis of Compound 345

[0115] Following the preparation method of Synthesis Example 6, A-1 was replaced with an equimolar amount of A-345, B-1 with an equimolar amount of B-345, and E-1 with an equimolar amount of E-297, yielding compound 345 (5.26 g) with an HPLC purity ≥ 99.97%. Mass spectrometry m / z: 740.2161 (theoretical value: 740.2174). Theoretical elemental content (%) C 55 H 32 OS: C, 89.16; H, 4.35; Actual element content (%): C, 89.15; H, 4.37.

[0116] Synthesis Example 20: Synthesis of Compound 379

[0117] Following the preparation method of Synthesis Example 6, B-1 was replaced with an equimolar amount of B-379, and E-1 was replaced with an equimolar amount of E-379, yielding compound 379 (5.00 g) with an HPLC purity ≥ 99.96%. Mass spectrometry m / z: 666.2941 (theoretical value: 666.2956). Theoretical elemental content (%) C 48 H 42 OS: C, 86.45; H, 6.35; Actual element content (%): C, 86.44; H, 6.36.

[0118] Synthesis Example 21: Synthesis of Compound 383

[0119] Following the preparation method of Synthesis Example 6, B-1 was replaced with an equimolar amount of B-383 to obtain compound 383 (5.14 g), with an HPLC purity ≥ 99.93%. Mass spectrometry m / z: 642.1462 (theoretical value: 642.1476). Theoretical elemental content (%) C 46 H 26 S2: C, 85.95; H, 4.08; Actual element content (%): C, 85.94; H, 4.09.

[0120] Synthesis Example 22: Synthesis of Compound 397

[0121] Following the preparation method of Synthesis Example 6, A-1 was replaced with an equimolar amount of A-397, B-1 with an equimolar amount of B-397, and E-1 with an equimolar amount of E-297, yielding compound 397 (4.45 g) with an HPLC purity ≥ 99.95%. Mass spectrometry m / z: 600.1563 (theoretical value: 600.1548). Theoretical elemental content (%) C 44 H 24 OS: C, 87.97; H, 4.03; Actual element content (%): C, 87.98; H, 4.01.

[0122] Synthesis Example 23: Synthesis of Compound 425

[0123] Following the preparation method of Synthesis Example 6, B-1 was replaced with an equimolar amount of B-425, and E-1 was replaced with an equimolar amount of E-425 to obtain compound 425 (6.52 g), with an HPLC purity ≥ 99.98%. Mass spectrometry m / z: 904.2816 (theoretical value: 904.2800). Theoretical elemental content (%) C 68 H 40 OS: C, 90.24; H, 4.45; Actual element content (%): C, 90.26; H, 4.44.

[0124] Synthesis Example 24: Synthesis of Compound 443

[0125] Following the preparation method of Synthesis Example 6, B-1 was replaced with an equimolar amount of B-443, and E-1 was replaced with an equimolar amount of E-443, yielding compound 443 (3.84 g) with an HPLC purity ≥ 99.97%. Mass spectrometry m / z: 485.1429 (theoretical value: 485.1416). Theoretical elemental content (%) C 35 H 19 NO2: C, 86.58; H, 3.94; N, 2.88; Actual element content (%): C, 86.57; H, 3.96; N, 2.87.

[0126] Synthesis Example 25: Synthesis of Compound 457

[0127] Following the preparation method of Synthesis Example 6, A-1 was replaced with an equimolar amount of A-345, B-1 with an equimolar amount of B-457, and E-1 with an equimolar amount of E-332, yielding compound 457 (4.52 g) with an HPLC purity ≥ 99.96%. Mass spectrometry m / z: 602.1440 (theoretical value: 602.1453). Theoretical elemental content (%) C 42 H 22 N2OS: C, 83.70; H, 3.68; N, 4.65; Actual element content (%): C, 83.71; H, 3.67; N, 4.64.

[0128] Synthesis Example 26: Synthesis of Compound 474

[0129] Following the preparation method of Synthesis Example 6, B-1 was replaced with an equimolar amount of B-474, and E-1 was replaced with an equimolar amount of E-474, yielding compound 474 (4.56 g) with an HPLC purity ≥ 99.94%. Mass spectrometry m / z: 633.1235 (theoretical value: 633.1221). Theoretical elemental content (%) C 43 H 23 NOS2: C, 81.49; H, 3.66; N, 2.21; Actual element content (%): C, 81.47; H, 3.65; N, 2.24.

[0130] Synthesis Example 27: Synthesis of Compound 485

[0131] Following the preparation method of Synthesis Example 6, B-1 was replaced with an equimolar amount of B-485, and E-1 was replaced with an equimolar amount of E-485, yielding compound 485 (4.45 g) with an HPLC purity ≥ 99.92%. Mass spectrometry m / z: 626.2232 (theoretical value: 626.2246). Theoretical elemental content (%) C 47 H 30 O2: C, 90.07; H, 4.82; Actual element content (%): C, 90.06; H, 4.83.

[0132] Synthesis Example 28: Synthesis of Compound 492

[0133] Following the preparation method of Synthesis Example 6, B-1 was replaced with an equimolar amount of B-492, and E-1 was replaced with an equimolar amount of E-492, yielding compound 492 (4.43 g) with an HPLC purity ≥ 99.95%. Mass spectrometry m / z: 606.1101 (theoretical value: 606.1112). Theoretical elemental content (%) C 42 H 22 OS2: C, 83.14; H, 3.65; Actual element content (%): C, 83.15; H, 3.63.

[0134] Synthesis Example 29: Synthesis of Compound 512

[0135] Preparation of intermediate D-512: Under a nitrogen atmosphere, A-512 (18.00 g, 50 mmol), pinacol diborate (33.01 g, 130 mmol), and potassium acetate (25.52 g, 260 mmol) were added sequentially to a reaction flask. Then, 1000 mL of DMF was added, and after purging the air three times with nitrogen, Pd(dppf)Cl2 (1.06 g, 1.3 mmol) was added. The reaction system was heated and stirred, and refluxed for 6 h. After the reaction was complete, the mixture was cooled to room temperature, distilled water was added, and the mixture was extracted with ethyl acetate (800 mL × 3 times). The organic phase was separated, dried over anhydrous magnesium sulfate, and then rotary evaporated under reduced pressure to obtain the crude product. The obtained solid was purified by recrystallization from n-hexane:ethyl acetate in an 8:1 ratio to give intermediate D-512 (18.85 g, yield 83%); HPLC purity ≥ 99.87%. Mass spectrometry m / z: 454.2472 (theoretical value: 454.2487).

[0136] Preparation of compound 512: Under nitrogen protection, D-512 (4.54 g, 10 mmol), E-512 (5.50 g, 20 mmol), K3PO4 (8.49 g, 40 mmol), Pd(OAc)2 (0.09 g, 0.40 mmol), X-Phos (0.38 g, 0.80 mmol), toluene (200 ml), and water (10 ml) were added to a reaction flask, and the mixture was reacted under reflux for 12 hours. After the reaction was completed, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic phase was washed with water, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The mixture was then subjected to silica gel column chromatography (n-hexane:ethyl acetate = 6:1) to give compound 512 (5.50 g, 81%). The purity of the solid was ≥99.97% as determined by HPLC. Mass spectrometry m / z: 678.0619 (theoretical value: 678.0604). Theoretical elemental content (%) C 44 H 22 S4: C, 77.84; H, 3.27; Actual element content (%): C, 77.85; H, 3.26.

[0137] Synthesis Example 30: Synthesis of Compound 546

[0138] Following the preparation method of Synthesis Example 6, B-1 was replaced with an equimolar amount of B-546, and E-1 was replaced with an equimolar amount of E-546, yielding compound 546 (5.31 g) with an HPLC purity ≥ 99.96%. Mass spectrometry m / z: 758.1724 (theoretical value: 758.1738). Theoretical elemental content (%) C 54 H 30OS2: C, 85.46; H, 3.98; Actual element content (%): C, 85.47; H, 3.97.

[0139] Synthesis Example 31: Synthesis of Compound 565

[0140] Following the preparation method of Synthesis Example 6, A-1 was replaced with an equimolar amount of A-565, B-1 with an equimolar amount of B-565, and E-1 with an equimolar amount of E-565, yielding compound 565 (5.10 g) with an HPLC purity ≥ 99.94%. Mass spectrometry m / z: 738.3055 (theoretical value: 738.3069). Theoretical elemental content (%) C 53 H 42 N2S: C, 86.14; H, 5.73; N, 3.79; Actual element content (%): C, 86.13; H, 5.75; N, 3.78.

[0141] Synthesis Example 32: Synthesis of Compound 588

[0142] Following the preparation method of Synthesis Example 6, B-1 was replaced with an equimolar amount of B-588, and E-1 was replaced with an equimolar amount of E-332, yielding compound 588 (5.05 g) with an HPLC purity ≥ 99.96%. Mass spectrometry m / z: 742.2343 (theoretical value: 742.2330). Theoretical elemental content (%) C 55 H 34 OS: C, 88.92; H, 4.61; Actual element content (%): C, 88.91; H, 4.63.

[0143] Synthesis Example 33: Synthesis of Compound 597

[0144] Following the preparation method of Synthesis Example 6, A-1 was replaced with an equimolar amount of A-597, B-1 with an equimolar amount of B-597, and E-1 with an equimolar amount of E-597, yielding compound 597 (4.67 g) with an HPLC purity ≥ 99.92%. Mass spectrometry m / z: 752.2728 (theoretical value: 752.2715). Theoretical elemental content (%) C 57 H 36 O2: C, 90.93; H, 4.82; Actual element content (%): C, 90.95; H, 4.80.

[0145] Synthesis Example 34: Synthesis of Compound 615

[0146] Following the preparation method of Synthesis Example 29, A-512 was replaced with an equimolar amount of A-615, and E-512 was replaced with an equimolar amount of E-1, yielding compound 615 (5.17 g) with an HPLC purity ≥ 99.97%. Mass spectrometry m / z: 679.0541 (theoretical value: 679.0557). Theoretical elemental content (%) C 43 H 21 NS4: C, 75.96; H, 3.11; N, 2.06; Actual element content (%): C, 75.95; H, 3.13; N, 2.05.

[0147] Synthesis Example 35: Synthesis of Compound 619

[0148] Following the preparation method of Synthesis Example 6, A-1 was replaced with an equimolar amount of A-345, B-1 with an equimolar amount of B-619, and E-1 with an equimolar amount of E-619, yielding compound 619 (3.96 g) with an HPLC purity ≥ 99.96%. Mass spectrometry m / z: 535.1558 (theoretical value: 535.1572). Theoretical elemental content (%) C 39 H 21 NO2: C, 87.46; H, 3.95; N, 2.62; Actual element content (%): C, 87.45; H, 3.94; N, 2.64.

[0149] Synthesis Example 36: Synthesis of Compound 630

[0150] Following the preparation method of Synthesis Example 6, B-1 was replaced with an equimolar amount of B-630, and E-1 was replaced with an equimolar amount of E-630, yielding compound 630 (4.86 g) with an HPLC purity ≥ 99.94%. Mass spectrometry m / z: 656.1285 (theoretical value: 656.1269). Theoretical elemental content (%) C 46 H 24 OS2: C, 84.12; H, 3.68; Actual element content (%): C, 84.14; H, 3.67.

[0151] Synthesis Example 37: Synthesis of Compound 682

[0152] Following the preparation method of Synthesis Example 6, A-1 was replaced with an equimolar amount of A-682, B-1 with an equimolar amount of B-240, and E-1 with an equimolar amount of E-332, yielding compound 682 (4.72 g) with an HPLC purity ≥ 99.98%. Mass spectrometry m / z: 628.2241 (theoretical value: 628.2256). Theoretical elemental content (%) C 43 H 36 OSSi: C, 82.12; H, 5.77; Actual element content (%): C, 82.14; H, 5.75.

[0153] Synthesis Example 38: Synthesis of Compound 723

[0154] Preparation of intermediate D-723: Under a nitrogen atmosphere, A-723 (21.95 g, 50 mmol), pinacol diborate (38.09 g, 150 mmol), and potassium acetate (29.44 g, 300 mmol) were added sequentially to a reaction flask. Then, 750 mL of DMF was added, and after purging the air three times with nitrogen, Pd(dppf)Cl2 (1.22 g, 1.5 mmol) was added. The reaction system was heated and stirred, and refluxed for 6 h. After the reaction was complete, the mixture was cooled to room temperature, distilled water was added, and the mixture was extracted with ethyl acetate (800 mL × 3 times). The organic phase was separated, dried over anhydrous magnesium sulfate, and then rotary evaporated under reduced pressure to obtain the crude product. The obtained solid was purified by recrystallization from n-hexane:ethyl acetate in an 8:1 ratio to give intermediate D-723 (24.08 g, yield 83%); HPLC purity ≥ 99.89%. Mass spectrometry m / z: 580.3352 (theoretical value: 580.3339).

[0155] Preparation of compound 723: Under nitrogen protection, D-723 (5.80 g, 10 mmol), E-332 (9.10 g, 30 mmol), K3PO4 (12.74 g, 60 mmol), Pd(OAc)2 (0.13 g, 0.60 mmol), X-Phos (0.57 g, 1.20 mmol), toluene (250 ml), and water (10 ml) were added to a reaction flask, and the mixture was reacted under reflux for 12 hours. After the reaction was completed, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic phase was washed with water, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The mixture was then subjected to silica gel column chromatography (n-hexane:ethyl acetate = 6:1) to give compound 723 (6.52 g, 75%). The purity of the solid was ≥99.97% as determined by HPLC. Mass spectrometry m / z: 868.1218 (theoretical value: 868.1201). Theoretical elemental content (%) C58 H 28 O3S3: C, 80.16; H, 3.25; Actual element content (%): C, 80.15; H, 3.26.

[0156] Synthesis Example 39: Synthesis of Compound 734

[0157] Preparation of intermediate C-734: Under nitrogen protection, A-734 (47.34 g, 100 mmol), B-1 (36.58 g, 300 mmol), K₂CO₃ (62.19 g, 450 mmol), Pd(PPh₃)₄ (3.47 g, 3 mmol), toluene (1500 ml), ethanol (300 ml), and water (300 ml) were added to a reaction flask, and the mixture was reacted under reflux for 10 hours. After the reaction was completed, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic phase was washed with water, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The mixture was then subjected to silica gel column chromatography (petroleum ether: dichloromethane = 6:1) to give intermediate C-734 (33.48 g, 72%). The purity of the solid was ≥99.79% as determined by HPLC. Mass spectrometry m / z: 464.1346 (theoretical value: 464.1332).

[0158] Preparation of intermediate D-734: Under a nitrogen atmosphere, C-734 (23.25 g, 50 mmol), pinacol diborate (12.70 g, 50 mmol), and potassium acetate (9.81 g, 100 mmol) were added sequentially to a reaction flask. Then, 300 mL of DMF was added, and after purging the air three times with nitrogen, Pd(dppf)Cl2 (0.41 g, 0.5 mmol) was added. The reaction system was heated and stirred, and refluxed for 6 h. After the reaction was complete, the mixture was cooled to room temperature, distilled water was added, and the mixture was extracted with ethyl acetate (800 mL × 3 times). The organic phase was separated, dried over anhydrous magnesium sulfate, and then rotary evaporated under reduced pressure to obtain the crude product. The obtained solid was purified by recrystallization from n-hexane:ethyl acetate in an 8:1 ratio to give intermediate D-734 (21.98 g, yield 79%); HPLC purity ≥ 99.87%. Mass spectrometry m / z: 556.2560 (theoretical value: 556.2574).

[0159] Preparation of compound 1: Under nitrogen protection, D-734 (5.57 g, 10 mmol), E-1 (3.19 g, 10 mmol), K3PO4 (4.25 g, 20 mmol), Pd(OAc)2 (0.04 g, 0.20 mmol), X-Phos (0.19 g, 0.40 mmol), toluene (100 ml), and water (5 ml) were added to a reaction flask, and the mixture was reacted under reflux for 12 hours. After the reaction was completed, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic phase was washed with water, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The mixture was then subjected to silica gel column chromatography (n-hexane:ethyl acetate = 6:1) to give compound 734 (5.08 g, 76%). The purity of the solid was ≥99.92% as determined by HPLC. Mass spectrometry m / z: 668.1647 (theoretical value: 668.1632). Theoretical elemental content (%) C 48 H 28 S2: C, 86.19; H, 4.22; Actual element content (%): C, 86.17; H, 4.24.

[0160] Synthesis Example 40: Synthesis of Compound 746

[0161] Preparation of intermediate D-746: Under a nitrogen atmosphere, A-746 (25.89 g, 50 mmol), pinacol diborate (50.79 g, 200 mmol), and potassium acetate (39.26 g, 400 mmol) were added sequentially to a reaction flask. Then, 1500 mL of DMF was added, and after purging the air three times with nitrogen, Pd(dppf)Cl2 (1.63 g, 2 mmol) was added. The reaction system was heated and stirred, and refluxed for 5 h. After the reaction was complete, the mixture was cooled to room temperature, distilled water was added, and the mixture was extracted with ethyl acetate (800 mL × 3 times). The organic phase was separated, dried over anhydrous magnesium sulfate, and then rotary evaporated under reduced pressure to obtain the crude product. The obtained solid was purified by recrystallization from n-hexane:ethyl acetate in an 8:1 ratio to give intermediate D-746 (28.24 g, 80% yield); HPLC purity ≥ 99.82%. Mass spectrometry m / z: 706.4176 (theoretical value: 706.4191).

[0162] Preparation of compound 1: Under nitrogen protection, D-746 (7.06 g, 10 mmol), E-1 (12.77 g, 40 mmol), K3PO4 (16.98 g, 80 mmol), Pd(OAc)2 (0.18 g, 0.80 mmol), X-Phos (0.76 g, 1.60 mmol), toluene (250 ml), and water (10 ml) were added to a reaction flask, and the mixture was reacted under reflux for 12 hours. After the reaction was completed, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic phase was washed with water, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The mixture was then subjected to silica gel column chromatography (n-hexane:ethyl acetate = 6:1) to give compound 723 (8.90 g, 77%). The purity of the solid was ≥99.96% as determined by HPLC. Mass spectrometry m / z: 1154.0440 (theoretical value: 1154.0426). Theoretical elemental content (%) C 72 H 34 S8: C, 74.84; H, 2.97; Actual element content (%): C, 74.85; H, 2.96.

[0163] Synthesis Example 41: Synthesis of Compound 769

[0164] Following the preparation method of Synthesis Example 39, B-1 was replaced with an equimolar amount of B-769, and E-1 was replaced with an equimolar amount of E-443, yielding compound 769 (6.80 g) with an HPLC purity ≥ 99.92%. Mass spectrometry m / z: 906.2422 (theoretical value: 906.2406). Theoretical elemental content (%) C 66 H 34 O5: C, 87.40; H, 3.78; Actual element content (%): C, 87.42; H, 3.76.

[0165] Device Example 1: In this invention, the ITO glass substrate is ultrasonically cleaned twice with a 5% glass cleaning solution for 20 minutes each time, followed by ultrasonic cleaning twice with deionized water for 10 minutes each time. It is then ultrasonically cleaned sequentially with acetone and isoacetone for 20 minutes each time, and dried at 120°C. All organic materials are sublimated and have a purity of over 99.99%.

[0166] 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 atmospheric, at room temperature.

[0167] On an ITO transparent electrode, a hole injection layer is formed by thermal vacuum evaporation of the following 2-TNATA compound to a thickness of 5 nm. Next, a first hole transport layer is formed by thermal vacuum evaporation of HTL-1 to a thickness of 100 nm, and a second hole transport layer is formed by thermal vacuum evaporation of HTL-2 to a thickness of 10 nm. Next, a first light-emitting layer with a thickness of 8 nm is formed by simultaneous vacuum evaporation of the following compound 1 (substrate) synthesized in the above synthesis example and the following compound BD (dopant) (substrate compound weight ratio:dopant compound weight ratio = 95:5). Next, a second light-emitting layer with a thickness of 16 nm is formed by simultaneous vacuum evaporation of the following compound BH (substrate) and the following compound BD (dopant) (substrate compound weight ratio:dopant compound weight ratio = 95:5). Next, an electron transport layer is formed by vacuum evaporation of the following compound ETL to a thickness of 20 nm. Next, an electron injection layer is formed by vacuum evaporation of LiF to a thickness of 0.5 nm. Next, aluminum is vapor-deposited to a thickness of 100 nm to form a cathode, thereby manufacturing an organic light-emitting device.

[0168] Device Examples 2 to 36: Compound 1 in Device Example 1 was replaced as the main material by replacing compound 1 with compounds 58, 60, 132, 155, 198, 218, 232, 240, 283, 294, 332, 339, 345, 379, 383, 397, 425, 443, 457, 474, 485, 492, 512, 546, 565, 588, 597, 615, 619, 630, 682, 723, 734, 746, and 769, respectively. Otherwise, an organic electroluminescent device was prepared using the same preparation method as Device Example 1.

[0169] Comparative Examples 1 to 5: Comparative compounds 1, 2, 3, 4, and 5 were used to replace compound 1 in device example 1 as the main material. Otherwise, an organic electroluminescent device was prepared using the same preparation method as device example 1.

[0170] The molecular structures of the relevant materials are shown below:

[0171] A combined IVL testing system was used to test the current efficiency and peak emission of organic electroluminescent devices (OLEDs). This system consisted of testing software, a computer, a Keithley K2400 digital source meter, and a PhotoResearch PR788 spectrophotometer. The full width at half maximum (FWHM) in the thin-film state was obtained using a Horiba Fluorolog-3 series fluorescence spectrometer. The lifetime of the OLEDs was tested using a McScience M6000 OLED lifetime testing system. The testing environment was atmospheric, at room temperature.

[0172] After completing the OLED light-emitting device as described above, the anode and cathode are connected using a known driving circuit. The luminous efficiency, half-width at half-maximum, peak emission, and lifetime of the device are measured. The test results of the device are shown in Table 1.

[0173] Table 1: Luminescence characteristics test results of Device Examples 1 to 36 and Comparative Examples 1 to 5:

[0174]

[0175] As can be seen from the data in Table 1, when the materials of other functional layers of organic electroluminescent devices are the same, organic electroluminescent devices containing the compound of Formula 1 of this invention as the main material for blue light have higher luminous efficiency, higher color purity, and longer lifespan.

[0176] In summary, the above are merely preferred embodiments of the present invention and are not intended to limit the present invention. Any modifications, equivalent substitutions, improvements, etc., made within the spirit and principles of the present invention should be included within the protection scope of the present invention.

Claims

1. A pyrene compound, characterized in that, The pyrene compounds are selected from the structures shown in Formula 1: In Equation 1, each of the n is independently selected from N or CRn, and the n connected to L1 is selected from C; Each of the Rn groups is independently selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C24 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C30... Any one of the following: aryl, substituted or unsubstituted C2-C30 heteroaryl, fused ring of substituted or unsubstituted C3-C20 aliphatic ring and C6-C30 aromatic ring, fused ring of substituted or unsubstituted C3-C20 aliphatic ring and C2-C30 heteroaromatic ring, when two or more Rn are present at the same time, the two or more Rn are the same or different, or adjacent two Rn can be connected to form a substituted or unsubstituted ring; And at least one Rn is not selected from H; The L1 is selected from any one of the following: a single bond, a substituted or unsubstituted C6-C30 arylene, a substituted or unsubstituted C2-C30 heteroarylene, a fused cycloalcoholic group of a substituted or unsubstituted C3-C20 aliphatic ring and a C6-C30 heteroarylene ring, or a fused cycloalcoholic group of a substituted or unsubstituted C3-C20 aliphatic ring and a C2-C30 heteroarylene ring; The m1 is selected from 0, 1, 2, 3, 4 or 5; The Ar is selected from the group shown in Formula A or the group shown in Formula B; The rings A1 and A2 are each independently selected from any one of the following: substituted or unsubstituted C6-C30 aromatic rings, substituted or unsubstituted C2-C30 heteroaromatic rings, and rings formed by fusion of substituted or unsubstituted C3-C20 aliphatic rings and C6-C30 aromatic rings. X1 is selected from O or S; X2 is selected from O, S or CR6R7; The Y is selected from O, S, or CR6R7; R6 and R7 are each independently selected from any one of hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 aliphatic ring and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C20 aliphatic ring and C2-C30 heteroaromatic ring, or R6 and R7 are interconnected to form substituted or unsubstituted rings.

2. The pyrene compound according to claim 1, characterized in that, Equation 1 is selected from any of the following structures: The value of i is selected from 0, 1, 2, 3, 4 or 5; The value of j is selected from 0, 1, 2, 3 or 4; p is selected from 0, 1, 2, or 3; The q is selected from 0, 1, or 2; The definitions of Rn, L1, m1, X1, X2, Y, ring A1, and ring A2 are the same as those in the compound of formula 1.

3. The pyrene compound according to claim 1, characterized in that, Equation 1 is selected from any of the following structures: The value of i is selected from 0, 1, 2, 3, 4 or 5; The value of j is selected from 0, 1, 2, 3 or 4; p is selected from 0, 1, 2, or 3; The q is selected from 0, 1, or 2; The definitions of Rn, L1, m1, X1, X2, Y, ring A1, and ring A2 are the same as those in the compound of formula 1.

4. The pyrene compound according to claim 1, characterized in that, Formula A and Formula B are each independently selected from any one of the following groups: a' is selected from 0, 1, 2, 3, 4, 5, 6, or 7; b' is selected from 0, 1, 2, 3, 4, 5, or 6; c' is selected from 0, 1, 2, 3, 4, or 5; d' is selected from 0, 1, 2, 3, or 4; e' is selected from 0, 1, 2, or 3; f' is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; R8 and R9 are each independently selected from any one of hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, substituted or unsubstituted C2-C30 fused cycloalcoholic group of aliphatic ring and C6-C30 aromatic ring, substituted or unsubstituted fused cycloalcoholic group of aliphatic ring and C2-C30 heteroaromatic ring, or R8 and R9 are interconnected to form substituted or unsubstituted rings; The definitions of R6 and R7 are the same as those in the compound of Formula 1.

5. The pyrene compound according to claim 1, characterized in that, Each L1 is independently selected from a single bond or any of the following groups: Each u is independently selected from CRu or N, and at least one u is not selected from N; Each Ru is independently selected from any one of hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkoxy, substituted or unsubstituted C6-C30 aryl, 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, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaryl ring, or substituted or unsubstituted Ru are connected to form substituted or unsubstituted rings; The ring C is selected from substituted or unsubstituted C3~C20 alicyclic rings; U1 is selected from O, S, or NR1; The U2 is selected from N or CR2; The V is selected from single bond, O, S, CR3R4, NR5, SiR3R4, GeR3R4, or Se; The W is selected from O, S, CR3R4, NR5, SiR3R4, GeR3R4, or Se; R1, R2, R3, R4, and R5 are each independently selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6 Any one of the following: ~C30 aryloxy group, substituted or unsubstituted C6~C30 aryl group, substituted or unsubstituted C2~C30 heteroaryl group, substituted or unsubstituted amino group, fused cycloalcoholic group of substituted or unsubstituted C3~C20 alicyclic group and C6~C30 aromatic group, fused cycloalcoholic group of substituted or unsubstituted C3~C20 alicyclic group and C2~C30 heteroaromatic group, or R3 and R4 connected to form a substituted or unsubstituted ring.

6. The pyrene compound according to claim 1, characterized in that, The pyrene compounds are selected from any one of the following structures: 。 7. An organic electroluminescent device, characterized in that, The organic electroluminescent device comprises one or more of the pyrene compounds according to any one of claims 1 to 6.

8. The organic electroluminescent device according to claim 7, wherein the organic electroluminescent device comprises an anode, a cathode, and an organic functional layer, wherein the organic functional layer comprises one or more of a hole transport region, a light-emitting layer, an electron transport region, and a capping layer on the side of the cathode facing away from the anode, characterized in that, The organic functional layer comprises one or more of the pyrene compounds described in any one of claims 1 to 6.

9. The organic electroluminescent device according to claim 7, wherein the organic electroluminescent device comprises an anode, a cathode, and an organic functional layer, the organic functional layer comprising a hole transport region, a light-emitting layer, and an electron transport region located between the anode and the cathode, characterized in that, The light-emitting layer comprises one or more of the pyrene compounds described in any one of claims 1 to 6.

10. The organic electroluminescent device according to claim 9, wherein the light-emitting layer comprises a host material and a guest material, characterized in that, The main material comprises one or more of the pyrene compounds described in any one of claims 1 to 6.

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