An organic light emitting device

Abstract

This invention provides an organic light-emitting device, belonging to the field of organic electroluminescence technology. The capping material in the organic light-emitting device of this invention can reduce total internal reflection loss and waveguide loss in OLED devices, effectively improving the luminous efficiency and lifespan of the device. It has good application effects and industrialization prospects, and can be widely used in panel displays, lighting sources, organic solar cells, organic photosensitive materials, or organic thin-film transistors.

Description

Technical Field

[0001] This invention relates to the field of organic electroluminescence technology, and more particularly to an organic light-emitting device. Background Technology

[0002] Organic light emission (OLED) generally refers to the phenomenon of converting electrical energy into light energy using organic materials. Organic light-emitting devices (OLEDs) typically have a structure comprising an anode, a cathode, and an organic functional layer between them. The organic functional layer is usually formed as a multilayer structure of different materials to improve the efficiency and stability of the OLED. For example, the organic functional layer can be formed from a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied between the two electrodes in such an OLED structure, holes and electrons are injected into the organic material layer from the anode and cathode, respectively. When the injected holes and electrons meet, they form excitons, which emit light when they return to the ground state.

[0003] The efficiency of organic light-emitting elements can generally be divided into internal luminous efficiency and external luminous efficiency. Internal luminous efficiency is related to the efficiency of generating excitons and realizing light conversion in the organic layers between the cathode and anode, such as hole transport layer, light-emitting layer, and electron transport layer. Theoretically, the internal luminous efficiency of fluorescence is 25%, while that of phosphorescence is 100%.

[0004] Furthermore, external luminous efficiency refers to the efficiency of extracting light generated in the organic layer to the outside of the organic light-emitting device. It is currently known that approximately 20% of the internal luminous efficiency can typically be extracted. Optimization and performance improvement of OLED devices can be achieved by improving the combination of materials in any layer and different layers within the device. Specifically, the capping layer in an OLED device is a layer of organic or inorganic transparent material with a high refractive index. This capping layer material can effectively improve the device's light coupling efficiency and improve the light emission mode, allowing light that was originally confined inside the device to exit, exhibiting higher light extraction efficiency. However, current capping layer materials still offer limited improvement in the light extraction efficiency of OLED devices, and the luminous performance of OLED devices cannot meet user needs. Therefore, developing a new capping layer material to improve its film-forming properties and thermal stability, thereby enhancing the luminous efficiency and lifespan of the device, is an urgent problem to be solved. Summary of the Invention

[0005] The purpose of this invention is to provide an organic light-emitting device (OLED) with industrialization as the goal, based on existing technology. This device utilizes the structure shown in Formula I and is applied to a capping layer to develop OLEDs with high efficiency and long lifetime. Its general molecular structure is shown in Formula I.

[0006]

[0007] X is selected from O or S;

[0008] The L0 is selected from one of the following groups:

[0009]

[0010] The R p Selected from any one of hydrogen, deuterium, cyano, trifluoromethyl, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; or any two adjacent Rs. p Groups can bond together to form rings;

[0011] The V values ​​are the same or different, and are each independently selected from CR. b Or N, and at least one V is selected from N; when V is bonded to other groups, the V is selected from C;

[0012] The R b Selected from any one of hydrogen, deuterium, cyano, trifluoromethyl, halogen, methyl, ethyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, adamantyl, phenyl, biphenyl, naphthyl, deuterated phenyl, deuterated biphenyl, deuterated naphthyl, pyridyl, pyrimidinyl, or two adjacent R groups. b They connect to form substituted or unsubstituted benzene rings;

[0013] p1 is selected from 0, 1, 2, 3 or 4;

[0014] The R a Whether identical or different, each is independently selected from one of hydrogen, deuterium, cyano, trifluoromethyl, halogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C20 heteroaryl, or optionally two adjacent R groups. a Groups can bond together to form rings;

[0015] The 'a' is selected from 0, 1, 2, 3, 4, or 5;

[0016] Ar1 and Ar2 may be the same as or different from each other, and are each independently selected from one of the following: substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring.

[0017] L1 and L2 are independently selected from one of the following: single bond, substituted or unsubstituted C6-C25 arylene, and substituted or unsubstituted C2-C20 heteroarylene.

[0018] The beneficial effects of this invention are:

[0019] This invention provides an organic light-emitting device. The capping material in the organic light-emitting device of this invention can reduce total reflection loss and waveguide loss in OLED devices, effectively improving the luminous efficiency and lifespan of the device. Detailed Implementation

[0020] The technical solutions of the embodiments of the present invention will be clearly and completely described below. Obviously, the described embodiments are only some embodiments of the present invention, and not all embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without creative effort are within the protection scope of the present invention.

[0021] In the compounds of the present invention, any atom not specified as a particular isotope is included as any stable isotope of that atom, and includes atoms at both their natural and non-natural isotopic abundances.

[0022] In this invention, the use of "H" and "hydrogen" 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" 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. In this invention, the omission of undrawn hydrogen atoms signifies "H" or "hydrogen".

[0023] In this specification, when the position of the substituent on the ring is not fixed, it means that it can be attached to any of the corresponding optional sites on the ring. For example, Can represent And so on.

[0024] The halogens mentioned in this invention refer to fluorine, chlorine, bromine, and iodine.

[0025] The alkyl group described in this invention refers to a hydrocarbon group formed by removing one hydrogen atom from an alkane molecule. It can be a straight-chain alkyl group or a branched-chain alkyl group, preferably having 1 to 15 carbon atoms, more preferably 1 to 12 carbon atoms, and particularly preferably 1 to 6 carbon atoms. The straight-chain alkyl group includes methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl, etc., but is not limited thereto. The branched-chain alkyl group includes isopropyl, isobutyl, sec-butyl, tert-butyl, isomers of n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, etc., but is not limited thereto. The alkyl group is preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl.

[0026] The chain alkyl groups with more than three carbon atoms described in this invention include their isomers. For example, propyl includes n-propyl and isopropyl, and butyl includes n-butyl, sec-butyl, isobutyl, and tert-butyl. And so on.

[0027] The cycloalkyl group described in this invention refers to a hydrocarbon group formed by removing one hydrogen atom from a cycloalkane molecule, preferably having 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, and particularly preferably 3 to 6 carbon atoms. Examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, camphenyl, norbornyl, etc., but are not limited thereto. The cycloalkyl group is preferably cyclopentyl, cyclohexyl, 1-adamantyl, 2-adamantyl, or norbornyl.

[0028] The aryl group described in this invention refers to the general term for a monovalent group remaining after removing a hydrogen atom from the aromatic carbon atom of an aromatic compound molecule. It can be a monocyclic aryl, polycyclic aryl, or fused-ring aryl, preferably having 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 14 carbon atoms, and most preferably 6 to 12 carbon atoms. The monocyclic aryl refers to an aryl group with only one aromatic ring in the molecule, such as phenyl, but not limited thereto; the polycyclic aryl refers to an aryl group containing two or more independent aromatic rings in the molecule, such as biphenyl, terphenyl, etc., but not limited thereto; the fused-ring aryl refers to an aryl group containing two or more aromatic rings fused together by sharing two adjacent carbon atoms, such as naphthyl, anthracene, phenanthryl, pyrene, perylene, fluorene, benzo[a]fluorene, triphenylene, fluoranyl, spirodifluorene, etc., but not limited thereto. The aryl group is preferably phenyl, biphenyl, terphenyl, naphthyl (preferably 2-naphthyl), anthracene (preferably 2-anthrayl), phenanthryl, pyrene, peryl, fluorenyl, benzo[a]fluorenyl, triphenylene, or spirodifluorenyl.

[0029] The heteroaryl group described in this invention refers to the general term for groups obtained by replacing one or more aromatic carbon atoms in an aryl group with heteroatoms. The heteroatoms include, but are not limited to, oxygen, sulfur, nitrogen, or phosphorus atoms, preferably having 1 to 25 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 3 to 15 carbon atoms, and most preferably 3 to 12 carbon atoms. The linking site of the heteroaryl group can be located on a cyclic carbon atom or on a cyclic nitrogen atom. The heteroaryl group can be a monocyclic heteroaryl, a polycyclic heteroaryl, or a fused-ring heteroaryl. The monocyclic heteroaryl groups include, but are not limited to, pyridinyl, pyrimidinyl, triazinyl, furanyl, thiopheneyl, pyrroleyl, imidazolyl, etc.; the polycyclic heteroaryl groups include, but are not limited to, bipyridinyl, bipyrimidinyl, phenylpyridinyl, etc.; the fused-ring heteroaryl groups include, but are not limited to, quinolinyl, isoquinolinyl, indolyl, benzothiopheneyl, benzofuranyl, benzoxazolyl, benzoimidazolyl, benzothiazolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothiopheneyl, benzodibenzothiapheneyl, carbazolyl, benzocarbazolyl, acridinel, 9,10-dihydroacridinyl, phenoxazinyl, phenthiazinyl, phenoxthiazyl, etc., but are not limited to. The aforementioned heteroaryl groups are preferably pyridyl, pyrimidinyl, thiophene, furanyl, benzothiophene, benzofuranyl, benzooxazolyl, benzoimidazolyl, benzothiazolyl, dibenzofuranyl, dibenzothiophene, benzodibenzothiophene, benzodibenzofuranyl, carbazolyl, acridinel, phenoxazinyl, phenthiazinyl, and phenoxthialyl.

[0030] The fused ring of aromatic and aliphatic rings described in this invention refers to a molecule containing one or more aromatic rings and one or more aliphatic rings fused together by sharing two adjacent carbon atoms. The aromatic ring preferably has 6 to 30 carbon atoms, more preferably 6 to 18 carbon atoms, and most preferably 6 to 12 carbon atoms. The aliphatic ring preferably has 3 to 30 carbon atoms, more preferably 3 to 18 carbon atoms, more preferably 3 to 12 carbon atoms, and most preferably 3 to 7 carbon atoms. Examples include benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, naphthocyclopropane, naphthocyclobutane, naphthocyclopentane, naphthocyclohexane, naphthocyclopentenyl, naphthocyclohexenyl, etc., but are not limited thereto.

[0031] The arylene group referred to in this invention refers to the general term for the divalent group remaining after removing two hydrogen atoms from the aromatic carbon atom of an aromatic compound molecule. It can be a monocyclic arylene, a polycyclic arylene, or a fused-ring arylene, preferably having 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 14 carbon atoms, and most preferably 6 to 12 carbon atoms. The monocyclic arylene includes, but is not limited to, phenylene; the polycyclic arylene includes, but is not limited to, biphenylene, terphenylene; and the fused-ring arylene includes, but is not limited to, naphthylene, anthracene, phenanthrene, fluorene, pyrene, trimethyleneene, fluorene, and phenylfluorene. The aforementioned arylene groups are preferably phenylene, biphenylene, terphenylene, naphthyl, fluorene, or phenylfluorene.

[0032] The heteroaryl group described in this invention refers to the general term for groups obtained by replacing one or more aromatic carbon atoms in an aryl group with heteroatoms, wherein the heteroatoms include, but are not limited to, oxygen, sulfur, nitrogen, or phosphorus atoms. Preferably, it has 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 15 carbon atoms, and most preferably 3 to 12 carbon atoms. The linking site of the heteroaryl group can be located on a cyclic carbon atom or a cyclic nitrogen atom. The heteroaryl group can be a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a fused-ring heteroaryl group. The monocyclic heteroaryl group includes, but is not limited to, pyridinyl, pyrimidinyl, triazinyl, furanyl, and thiopheneyl; the polycyclic heteroaryl group includes, but is not limited to, bipyridinyl, bipyrimidinyl, and phenylpyridinyl; the fused-ring heteroaryl group includes, but is not limited to, quinolineyl, isoquinolineyl, indolyl, benzothiophene, benzofuranyl, benzoxazolyl, benzoimidazolyl, benzothiazolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothiaphene, benzodibenzothiaphene, carbazolyl, benzocarbazolyl, acridineyl, 9,10-dihydroacridinyl, phenoxazinyl, phenthiazinyl, and phenoxthiazolyl, but is not limited to. The aforementioned heteroaryl groups are preferably pyridinyl, pyrimidinyl, thiopheneyl, furanyl, benzothiopheneyl, benzofuranyl, benzoxazolyl, benzoimidazolyl, benzothiazolyl, dibenzofuranyl, dibenzothiopheneyl, benzodibenzothiopheneyl, benzodibenzofuranyl, carbazolyl, acridineyl, phenoxazinyl, phenoxazinyl, and phenoxthiazolyl.

[0033] The "unsubstituted..." in this invention, such as unsubstituted alkyl, unsubstituted cycloalkyl, unsubstituted aryl, unsubstituted heteroaryl, unsubstituted arylene, unsubstituted heteroaryl, etc., means that the "hydrogen" (H) in the group has not been replaced by other groups, including deuterium.

[0034] The term "substituted..." as used in this invention refers to substituted alkyl, substituted cycloalkyl, substituted aryl, substituted heteroaryl, substituted arylene, substituted heteroaryl, etc., meaning a group independently selected from, but not limited to, deuteryl, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C2-C15 heteroaryl, substituted or unsubstituted amino, etc., with mono- or poly-substituted groups, preferably selected from deuteryl, halogen, cyano, methyl, ethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, etc. The following groups are monosubstituted or polysubstituted: cyclohexyl, adamantyl, norbornel, camphenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, benzo[a]phenanthrene, perylene, pyrene, benzyl, tolyl, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, diphenylamino, dimethylamino, carbazole, 9-phenylcarbazole, acridine, furanyl, thiophene, benzofuranyl, benzothiophene, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, dibenzothiophene, phenothiazinyl, phenothiazinyl, and indole. Furthermore, the above substituents may also be substituted by one or more of the substituents described above, such as deuterium, halogen, cyano, alkyl, cycloalkyl, or aryl.

[0035] The cyclic structure formed by bonding as described in this invention refers to two groups being linked together by chemical bonds and optionally aromatized. Examples are shown below:

[0036]

[0037] In this invention, the ring formed by the connection can be a five-membered ring, a six-membered ring, or a fused ring, such as benzene, naphthalene, fluorene, cyclopentene, cyclohexene, cyclopentane, cyclohexane, cyclohexane, benzobenzene, quinoline, isoquinoline, dibenzothiophene, phenanthrene, or pyrene, but is not limited thereto.

[0038] The present invention provides an organic light-emitting device, comprising an anode, a cathode, and an organic layer, wherein the organic layer is located between the anode and the cathode or outside one or more electrodes of the anode and the cathode, and the organic layer contains any one or a combination of at least two of the structures shown in Formula I.

[0039] Preferably, the organic layer is located between the anode and the cathode, and the organic layer includes a hole transport region, a light-emitting layer, and an electron transport region, wherein the hole transport region and / or the light-emitting layer contains any one or a combination of at least two of the structures shown in Formula I.

[0040] Preferably, the organic layer includes a hole transport region located between the anode and the light-emitting layer, and the hole transport region contains any one or a combination of at least two of the structures shown in Formula I.

[0041] Preferably, the organic layer includes a light-emitting layer located between the hole transport region and the electron transport region, and the light-emitting layer contains any one or a combination of at least two of the structures shown in Formula I.

[0042] Preferably, the light-emitting layer comprises a host material and / or a dopant material, wherein the host material contains any one or a combination of at least two of the structures shown in Formula I.

[0043] More preferably, the organic layer is located outside either the anode or the cathode electrode, and the organic layer includes a capping layer containing any one or a combination of at least two of the structures shown in Formula I.

[0044] This invention provides an organic light-emitting device, wherein the organic layer contains the structure shown in Formula I:

[0045]

[0046] X is selected from O or S;

[0047] The L0 is selected from one of the following groups:

[0048]

[0049] The R p Selected from any one of hydrogen, deuterium, cyano, trifluoromethyl, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; or any two adjacent Rs. p Groups can bond together to form rings;

[0050] The V values ​​may be the same or different, and each is independently selected from CR. b Or N, and at least one V is selected from N; when V is bonded to other groups, the V is selected from C;

[0051] The R b Selected from any one of hydrogen, deuterium, cyano, trifluoromethyl, halogen, methyl, ethyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, adamantyl, phenyl, biphenyl, naphthyl, deuterated phenyl, deuterated biphenyl, deuterated naphthyl, pyridyl, pyrimidinyl, or two adjacent R groups. b They connect to form substituted or unsubstituted benzene rings;

[0052] p1 is selected from 0, 1, 2, 3 or 4;

[0053] The R aWhether identical or different, each is independently selected from one of hydrogen, deuterium, cyano, trifluoromethyl, halogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C20 heteroaryl, or optionally two adjacent R groups. a Groups can bond together to form rings;

[0054] The 'a' is selected from 0, 1, 2, 3, 4, or 5;

[0055] Ar1 and Ar2 may be the same as or different from each other, and are each independently selected from one of the following: substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring.

[0056] L1 and L2 are independently selected from one of the following: single bond, substituted or unsubstituted C6-C25 arylene, and substituted or unsubstituted C2-C20 heteroarylene.

[0057] Preferably, Formula I is selected from any one of the following structures:

[0058]

[0059] Preferably, the L0 is selected from one of the following groups:

[0060]

[0061]

[0062] Wherein, the R b The substituents, whether identical or different, are each independently selected from hydrogen, deuterium, cyano, trifluoromethyl, halogen, or substituted or unsubstituted groups of the following: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrimidinyl; wherein the substituents in "substituted or unsubstituted" are selected from one or more of deuterium, cyano, trifluoromethyl, halogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, deuterated phenyl, deuterated biphenyl, deuterated naphthyl, pyridyl, pyrimidinyl, and when substituted by multiple substituents, the multiple substituents are identical or different from each other;

[0063] b1 is selected from 0, 1, 2, or 3; b2 is selected from 0, 1, or 2; b3 is selected from 0 or 1; b4 is selected from 0, 1, 2, 3, 4, or 5; b5 is selected from 0, 1, 2, 3, or 4; when b1, b2, b4, and b5 are greater than 1, two or more R... b They are the same or different from each other.

[0064] Most preferably, the L0 is selected from one of the following groups:

[0065]

[0066]

[0067] Wherein, R' is selected from any one of hydrogen, deuterium, cyano, trifluoromethyl, halogen, methyl, ethyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, adamantyl, phenyl, biphenyl, naphthyl, deuterated phenyl, deuterated biphenyl, deuterated naphthyl, pyridyl, and pyrimidinyl.

[0068] Preferably, the R a The same or different, each independently selected from hydrogen, deuterium, cyano, trifluoromethyl, halogen, substituted or unsubstituted methyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, or optionally two adjacent R groups. a Groups can bond together to form benzene rings or naphthalene rings;

[0069] The value of 'a' is selected from 0, 1, 2, 3, 4, or 5.

[0070] More preferably, in Formula I Selected from one of the following groups:

[0071]

[0072]

[0073] X is selected from O or S.

[0074] Preferably, Ar1 and Ar2 are the same or different from each other, and each is independently selected from one of the following groups:

[0075]

[0076] In formula a, R1 is selected from one of hydrogen, deuterium, cyano, trifluoromethyl, halogen, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, and substituted or unsubstituted C3-C25 heteroaryl.

[0077] The n1 is selected from 0, 1, 2, 3, 4 or 5; when n1 is greater than 1, each R1 is the same or different, and two adjacent R1 groups can be bonded together to form a substituted or unsubstituted cyclic structure.

[0078] In formula b, X is selected from O, S, C(R) c (R) d Any one of N(R);

[0079] The R c R d Whether identical or different, each is independently selected from any one of hydrogen, deuterium, cyano, trifluoromethyl, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or R c R d They can combine to form substituted or unsubstituted spirorings; or R c R d Either of them can be directly bonded to L1 or L2;

[0080] R is selected from any one of deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or R can be directly bonded to L1 or L2.

[0081] R2 and R3 may be the same or different, and each is independently selected from any one of hydrogen, deuterium, cyano, trifluoromethyl, halogen, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, and substituted or unsubstituted C6-C25 aryl.

[0082] The n2 is selected from 0, 1, 2, 3 or 4; when n2 is greater than 1, each R2 is the same or different, and two adjacent R2 groups can be bonded together to form a substituted or unsubstituted cyclic structure; the n3 is selected from 0, 1, 2, 3 or 4; when n3 is greater than 1, each R3 is the same or different, and two adjacent R3 groups can be bonded together to form a substituted or unsubstituted cyclic structure.

[0083] In formula c, the z that are the same or different are selected from CR. zOr N, and 1-4 z are selected from N; when z is bonded to other groups, z is selected from C;

[0084] The R z They may be the same or different, and are each independently selected from any one of hydrogen, deuterium, cyano, trifluoromethyl, halogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, and substituted or unsubstituted pyridazinyl.

[0085] The n4 is selected from 0, 1, 2, 3 or 4; when n4 is greater than 1, each R4 is the same or different, and two adjacent R4 groups can bond together to form a substituted or unsubstituted cyclic structure.

[0086] More preferably, Ar1 and Ar2 may be the same as or different from each other, and each is independently selected from one of the following groups:

[0087]

[0088] R1 is selected from one of hydrogen, deuterium, cyano, trifluoromethyl, halogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, and substituted or unsubstituted naphthyl.

[0089] R2 and R3 are independently selected from one of hydrogen, deuterium, cyano, trifluoromethyl, halogen, methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornel, phenyl, naphthyl, tolyl, biphenyl, terphenyl, anthracene, phenanthrene, phenylenetriethylene, spirofluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, dibenzofuranyl, dibenzothiopheneyl, 9-phenylcarbazoyl, and carbazoyl. Furthermore, R2 and R3 can also be replaced by deuterium, cyano, trifluoromethyl, or halogen. The benzene ring is substituted with one or more of the following: methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, tolyl, biphenyl, deuterated biphenyl, terphenyl, anthracene, phenanthrene, and triphenylene; in the case of multiple substituents, the multiple substituents are the same or different from each other; or any two adjacent R2s combine with each other to form a substituted or unsubstituted benzene ring or naphthalene ring; or any two adjacent R3s combine with each other to form a substituted or unsubstituted benzene ring or naphthalene ring.

[0090] The R c R dR5 is independently selected from hydrogen, deuterium, cyano, trifluoromethyl, halogen, and any one of the following groups, substituted or unsubstituted: C1-C6 alkyl, C3-C6 cycloalkyl, adamantyl, norbornel, C6-C12 aryl, and C2-C12 heteroaryl; wherein the "substituted or unsubstituted" substituent is any one or more of deuterium, C1-C12 alkyl, and C3-C12 cycloalkyl.

[0091] The R is selected from deuterium, cyano, trifluoromethyl, halogen, or substituted or unsubstituted groups of the following: methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornel, phenyl, naphthyl, anthracene, phenanthrene, triphenylene, dibenzofuranyl, dibenzothiophene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirofluorenyl, and 9-phenylcarbazoyl.

[0092] The R4 is selected from one of hydrogen, deuterium, cyano, trifluoromethyl, halogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, and substituted or unsubstituted naphthyl.

[0093] The m1 is selected from 0, 1, 2, 3, 4 or 5; the m2 is selected from 0, 1, 2, 3 or 4; the m3 is selected from 0, 1, 2 or 3; the m4 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the m5 is selected from 0, 1 or 2; the m6 is selected from 0, 1, 2, 3, 4, 5 or 6; the m7 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; the m8 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; the m9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12 or 13.

[0094] More preferably, the Ar1 and Ar2 are the same as or different from each other, and each is independently selected from one of the following groups:

[0095]

[0096]

[0097] R1, R2, R3, R4, and R6 may be the same as or different from each other, and are independently selected from hydrogen, deuterium, cyano, trifluoromethyl, halogen, or substituted or unsubstituted groups of the following: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, and stilbeneyl; wherein the substituents in "substituted or unsubstituted" are selected from one or more of deuterium, cyano, trifluoromethyl, halogen, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, phenyl, biphenyl, and naphthyl, and in the case of being substituted by multiple substituents, the multiple substituents may be the same as or different from each other;

[0098] The R is selected from deuterium, methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornel, phenyl, naphthyl, anthracene, phenanthrene, triphenylene, dibenzofuranyl, dibenzothiophene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirofluorenyl, 9-phenylcarbazoleyl, and the above groups can also be replaced by deuterium, cyano, trifluoromethyl, halogen, methyl One or more of the following: alkyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornel, phenyl, naphthyl, tolyl, biphenyl, terphenyl, deuterated isopropyl, deuterated tert-butyl, deuterated cyclohexyl, deuterated cyclopentyl, deuterated cyclobutyl, deuterated cyclopropyl, deuterated adamantyl, deuterated norbornel, deuterated phenyl, deuterated naphthyl, and deuterated biphenyl;

[0099] The m1 is selected from 0, 1, 2, 3, 4 or 5; the m2 is selected from 0, 1, 2, 3 or 4; the m3 is selected from 0, 1, 2 or 3; the m4 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the m5 is selected from 0, 1 or 2; the m6 is selected from 0, 1, 2, 3, 4, 5 or 6; and the m7 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9.

[0100] Most preferably, Ar1 and Ar2 are the same or different from each other, and each is independently selected from one of the following groups:

[0101]

[0102]

[0103]

[0104]

[0105]

[0106] Preferably, L1 and L2 are independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted anthraceneylene, substituted or unsubstituted phenanthylene, substituted or unsubstituted trimethyleneene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothiopheneylene, substituted or unsubstituted benzofuranylene, substituted or unsubstituted benzothiopheneylene, substituted or unsubstituted fluoreneylene, substituted or unsubstituted carbazolylene, and substituted or unsubstituted pyridylene. The following are substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazineyl, substituted or unsubstituted pyridazineyl, substituted or unsubstituted pyrazineyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted phthalazineyl, substituted or unsubstituted naphthinyl, substituted or unsubstituted benzocyclopentyl, substituted or unsubstituted benzocyclohexyl, substituted or unsubstituted benzocyclopentenyl, substituted or unsubstituted benzocyclohexenyl, or any combination thereof.

[0107] More preferably, L1 and L2 are independently selected from single bonds or one of the following groups:

[0108]

[0109] The R q It is selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C25 aryl, and substituted or unsubstituted C2-C30 heteroaryl;

[0110] The same or different Y groups are selected from CR' or N, and at least one Y group is selected from N; when Y is bonded to other groups, the Y group is selected from C;

[0111] R' is selected from any one of hydrogen, deuterium, methyl, ethyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, biphenyl, naphthyl, deuterated phenyl, deuterated biphenyl, and deuterated naphthyl;

[0112] The q0 is selected from 0, 1, 2 or 3; the q1 is selected from 0, 1, 2, 3 or 4; the q2 is selected from 0, 1, 2, 3, 4, 5 or 6; the q3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; and the q4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.

[0113] More preferably, L1 and L2 are independently selected from single bonds or one of the following groups:

[0114]

[0115] The bridging L1 and L2 groups can be further replaced by one or more of the following: deuterium, cyano, fluoro, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, biphenyl, naphthyl, deuterated phenyl, deuterated biphenyl, deuterated naphthyl, pyridine, and pyrimidine.

[0116] R' is selected from any one of hydrogen, deuterium, methyl, ethyl, isopropyl, tert-butyl, phenyl, biphenyl, naphthyl, deuterated phenyl, deuterated biphenyl, and deuterated naphthyl.

[0117] Most preferably, the structure represented by Formula I is selected from any one of the following chemical structures:

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143] The heterocyclic derivatives of Formula I of this invention can be prepared by conventional coupling reactions in the art, for example, by the following synthetic route, but this invention is not limited thereto:

[0144] Preparation of intermediate B:

[0145]

[0146] Preparation of compound I:

[0147]

[0148] Among them, Xa, Xb, Xc, and Xd are independently selected from Cl, Br, or I; the restrictions on Ar1 to Ar2 and L0 to L2 are the same as those mentioned above.

[0149] The present invention does not impose any particular restrictions on the source of the raw materials used in the above-mentioned reactions, and commercially available raw materials or preparation methods known to those skilled in the art can be used.

[0150] Based on the direction of emitted light, the organic light-emitting diode provided by this invention can be made into any one of top-emitter devices, bottom-emitter devices, and double-sided emitting devices; based on the substrate, the organic light-emitting diode provided by this invention can be made into a device with a rigid glass substrate or a device with a flexible substrate.

[0151] The organic light-emitting device of the present invention is a top-emitting structure light-emitting device, which, for example, sequentially includes an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a transparent or semi-transparent cathode on a substrate.

[0152] The anode can be made of a high-power function electrode material, which can be a single-layer structure or a multi-layer composite structure. For example, the anode can be made of transparent materials such as indium tin oxide (ITO) or indium zinc oxide (IZO), or it can be made of a metal material with good conductivity sandwiched between two layers of indium tin oxide (ITO). The metal material can be any one of aluminum (Al), silver (Ag), titanium (Ti), molybdenum (Mo), or an alloy of any of the above.

[0153] The cathode can be made of metallic materials. For example, the cathode can be any one of lithium (Li), aluminum (Al), magnesium (Mg), silver (Ag), or an alloy of any of the above materials.

[0154] The hole transport region may include at least one selected from a hole injection layer, a hole transport layer, a hole buffer layer, and an electron blocking layer. The hole transport region may have a single-layer structure (such as a hole injection layer and / or a hole transport layer) or a single layer formed using a hole injection material and a hole transport material. In some embodiments, the hole transport region may have, but is not limited to, a single layer formed using a variety of different materials, or a multilayer laminated structure of hole injection layer / hole transport layer, hole injection layer / hole transport layer / hole buffer layer, hole injection layer / hole buffer layer, hole transport layer / hole buffer layer, or hole injection layer / hole transport layer / electron blocking layer laminated from the anode (e.g., on or above the anode). The thickness of the hole transport region may be from about 100 nm to about 150 nm.

[0155] Hole injection materials are preferably those with the highest occupied molecular orbital (HOMO) falling between the work function of the anolyte material and the HOMO of the surrounding organic material layer, as these materials advantageously receive holes from the anolyte at low voltages. Specific examples of hole injection materials include, but are not limited to, metalloporphyrins, oligothiophenes, arylamine-based organic materials, hexanitrile-based hexaazatriphenylene organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinones, and conductive polymers based on polyaniline and polythiophene.

[0156] Hole transport materials, which possess high hole mobility, are suitable for receiving holes from the anode or hole injection layer and transporting them to the emissive layer. Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers possessing both conjugated and non-conjugated portions. An electron blocking layer is a layer that prevents holes injected from the hole injection layer from passing through the emissive layer into the electron injection layer, thereby improving device lifespan and efficiency. Where necessary, a suitable portion can be formed between the emissive layer and the electron injection layer using known materials.

[0157] The luminescent material in the luminescent layer is a material capable of receiving and combining holes and electrons from the hole transport layer and electron transport layer, respectively, to emit light in the visible light region. Preferably, it is a material with high quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxyquinoline aluminum complexes (Alq3); carbazole compounds; dipolystyrene compounds; BAlq; 10-hydroxybenzoquinoline metal compounds; benzoazole, benzothiazole, and benzimidazole compounds; poly(p-phenylenevinylene) polymers; spirocyclic compounds; polyfluorene, fluorene, etc., but are not limited to these.

[0158] The luminescent layer can comprise a host material and dopant materials. The host material can be an aromatic fused-ring derivative or a heterocyclic compound. Specifically, aromatic fused-ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentanebenzene derivatives, phenanthrene compounds, and fluoranthene compounds; heterocyclic compounds include carbazole derivatives and dibenzofuran derivatives, but are not limited to these. The host material can be a single structure composed of a single substance, or a single-layer or multi-layer structure formed by different substances. The host material can include a single layer, or a luminescent layer composed of a first host material, a second host material, or more materials.

[0159] Dopant materials include aromatic amine derivatives, styrene-based heterocyclic derivatives, boron complexes, fluoranthene compounds, and metal complexes. Specifically, aromatic amine derivatives are aromatic fused-ring derivatives with substituted or unsubstituted arylamine groups, such as pyrene, anthracene, and diindronepyrene. Styrene-based heterocyclic derivatives are compounds in which at least one aryl vinyl group is substituted on a substituted or unsubstituted arylamine, and is substituted or unsubstituted by one or more substituents selected from aryl, silyl, alkyl, cycloalkyl, and arylamine groups. Specifically, examples include styrene-based amines, styrene-based diamines, styrene-based triamines, and styrene-based tetraamines, but are not limited to these. Furthermore, metal complexes include iridium complexes and platinum complexes, but are not limited to these. Dopant materials can be a single structure composed of a single substance, or a single-layer or multi-layer structure formed from different substances.

[0160] The electron transport region may include at least one of the following: an electron injection layer, an electron transport layer, a buffer layer, and a hole blocking layer. It can be a single structure composed of a single material, or a single-layer or multi-layer structure formed from different materials. The electron transport layer may be a single layer, or it may include a first electron transport layer, a second electron transport layer, or more layers. The type of electron transport region may be an electron injection layer / electron transport layer structure, an electron injection layer / electron transport layer / buffer layer structure, an electron injection layer / buffer layer structure, an electron transport layer / buffer layer structure, or an electron injection layer / electron transport layer / hole blocking layer structure, wherein the layers of each structure are stacked sequentially from the cathode in the order described, but the structure of the electron transport region is not limited to this.

[0161] Electron transport materials, which are materials with high electron mobility, are suitable as materials for advantageously receiving electrons from the cathode and transporting them to the light-emitting layer. Specific examples include, but are not limited to, Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, hydroxyflavonoid-metal complexes, etc.

[0162] The electron injection layer is a layer that injects electrons from the electrode. Preferably, it comprises compounds that possess electron transport capabilities, exhibit electron injection effects from the cathode, demonstrate excellent electron injection effects for the light-emitting layer or light-emitting material, prevent excitons generated in the light-emitting layer from migrating to the hole injection layer, and possess excellent thin film formation capabilities. Specifically, it includes fluorenones, anthraquinone dimethane, biphenylquinone, azoles, diazoles, triazoles, imidazoles, perylenetetracarboxylic acid, fluorenemethane, anthrones, and their derivatives, metal complexes, and nitrogen-containing 5-membered ring derivatives, but is not limited to these. Metal complexes include lithium 8-hydroxyquinoline, bis(8-hydroxyquinoline)zinc, bis(8-hydroxyquinoline)copper, bis(8-hydroxyquinoline)manganese, tris(8-hydroxyquinoline)aluminum, tris(2-methyl-8-hydroxyquinoline)aluminum, tris(8-hydroxyquinoline)gallium, bis(10-hydroxybenzo[h]quinoline)beryllium, bis(10-hydroxybenzo[h]quinoline)zinc, bis(2-methyl-8-quinoline)gallium chloride, bis(2-methyl-8-quinoline)(o-cresol)gallium, bis(2-methyl-8-quinoline)(1-naphthol)aluminum, etc., but are not limited to these.

[0163] The coating layer can be selected from Alq3, TPBi, or other known materials suitable for the coating layer, or the structure shown in Formula I of this invention.

[0164] There are no particular restrictions on the fabrication methods of each layer in organic light-emitting devices. They can be formed by vacuum evaporation, spin coating, vapor deposition, blade coating, inkjet printing, laser printing, and laser-induced thermal imaging (LITI).

[0165] The organic light-emitting device described in this invention can be widely used in panel displays, lighting sources, flexible OLEDs, electronic paper, organic solar cells, organic photosensitive materials or organic thin-film transistors, signs, signal lights and other fields.

[0166] The invention is explained in more detail through the following examples, but is not intended to limit the invention. Based on this description, those skilled in the art will be able to practice the invention and prepare other compounds and devices according to the invention within the entire scope disclosed without inventive effort.

[0167] Description of raw materials, reagents, and characterization equipment:

[0168] 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.

[0169] Mass spectrometry was performed using a Waters G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer, with chloroform as the solvent.

[0170] Elemental analysis was performed using a Vario EL cube organic elemental analyzer from Elementar GmbH, Germany, with sample masses ranging from 5 to 10 mg.

[0171] Preparation of intermediate B-6:

[0172]

[0173] Preparation of intermediate M-6:

[0174] Under nitrogen protection, starting material m-6 (19.24 g, 100.00 mmol), pinacol diboronate (27.93 g, 110.00 mmol), K2CO3 (41.46 g, 300.00 mmol), and Pd(PPh3)4 (3.47 g, 3.00 mmol) were added to DMF (470 mL). The mixture of the above reactants was heated under reflux for 3 h. After the reaction was completed, the reaction mixture was cooled to room temperature, distilled water was added, and the mixture was extracted with dichloromethane. After standing and separation, the organic layer was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. The obtained solid was recrystallized from ethyl acetate and dried to obtain intermediate M-6 (21.08 g, yield 88%). HPLC purity ≥ 98.81%. Mass spectrometry m / z: 239.0871 (theoretical value: 239.0884).

[0175] Preparation of intermediate B-6:

[0176] Under nitrogen protection, starting material b'-6 (14.78 g, 75.00 mmol), intermediate M-6 (19.16 g, 80.00 mmol), K2CO3 (20.73 g, 150.00 mmol), and Pd(PPh3)4 (1.73 g, 1.50 mmol) were added to 300 mL of toluene, 100 mL of ethanol, and 100 mL of water. The mixture of the above reactants was heated under reflux for 3 h. After the reaction was completed, the mixture was cooled to room temperature and filtered to obtain a filter cake. The filter cake was recrystallized from toluene / ethanol at a ratio of 4:1 to obtain starting material B-6 (15.07 g, yield 82%). The HPLC purity was ≥99.87%. Mass spectrometry m / z: 229.0282 (theoretical value: 229.0294).

[0177] By substituting the raw materials accordingly, intermediate B can be prepared according to the preparation method of intermediate B-6. The raw materials are shown in the table below:

[0178]

[0179]

[0180]

[0181] Synthesis Example 1: Preparation of Compound 6

[0182]

[0183] Synthetic intermediate A-6

[0184] Under nitrogen protection, B-6 (12.63 g, 55.00 mmol), b-6 (12.06 g, 55.00 mmol), and NaOt-Bu (8.65 g, 90.00 mmol) were dissolved in 450 mL of toluene. Pd(OAc)₂ (0.17 g, 0.75 mmol) and P(t-Bu)₃ (1.50 mL of 0.5 M toluene solution, 0.75 mmol) were added with stirring. The mixture of the above reactants was heated under reflux for 5 h. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallization from toluene / methanol (v / v 10:1) yielded intermediate A-6 (18.15 g, 80% yield), with a solid purity ≥99.90% as determined by HPLC. Mass spectrometry m / z: 412.1591 (theoretical value: 412.1576).

[0185] Synthetic compound 6

[0186] Under nitrogen protection, intermediates A-6 (16.50 g, 40.00 mmol), c-6 (8.28 g, 40.00 mmol), and NaOt-Bu (6.73 g, 70.00 mmol) were dissolved in 350 mL of toluene. Pd₂(dba)₃ (0.55 g, 0.60 mmol) and X-Phos (0.29 g, 0.60 mmol) were added with stirring. The mixture of the above reactants was heated under reflux for 7 h. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallization from toluene gave compound 6 (16.81 g, 78% yield). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 538.2061 (theoretical value: 538.2045). Theoretical elemental content (%) C 39 H 26 N₂O: C, 86.96; H, 4.87; N, 5.20. Measured elemental content (%): C, 87.00; H, 4.84; N, 5.23.

[0187] Synthesis Example 2: Preparation of Compound 9

[0188]

[0189] Following the same preparation method as in Synthesis Example 1, B-6 was replaced with an equimolar amount of B-9, b-6 with an equimolar amount of b-9, and c-6 with an equimolar amount of c-9 to obtain compound 9 (17.95 g). HPLC analysis showed a solid purity ≥99.99%. Mass spectrometry m / z: 614.2375 (theoretical value: 614.2358). Theoretical elemental content (%) C 45 H 30 N₂O: C, 87.92; H, 4.92; N, 4.56. Measured elemental content (%): C, 87.96; H, 4.89; N, 4.61.

[0190] Synthesis Example 3: Preparation of Compound 38

[0191]

[0192] Following the same preparation method as in Synthesis Example 1, B-6 was replaced with an equimolar amount of B-38, b-6 with an equimolar amount of b-38, and c-6 with an equimolar amount of c-38, yielding compound 38 (17.24 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 615.2324 (theoretical value: 615.2311). Theoretical elemental content (%) C 44 H 29N3O: C, 85.83; H, 4.75; N, 6.82. Measured elemental content (%): C, 85.87; H, 4.70; N, 6.85.

[0193] Synthesis Example 4: Preparation of Compound 50

[0194]

[0195] Following the same preparation method as in Synthesis Example 1, B-6 was replaced with an equimolar amount of B-50, b-6 with an equimolar amount of b-50, and c-6 with an equimolar amount of c-50, yielding compound 50 (15.08 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 489.1855 (theoretical value: 489.1841). Theoretical elemental content (%) C 34 H 23 N3O: C, 83.41; H, 4.74; N, 8.58. Measured elemental content (%): C, 83.44; H, 4.70; N, 8.60.

[0196] Synthesis Example 5: Preparation of Compound 53

[0197]

[0198] Following the same preparation method as in Synthesis Example 1, B-6 was replaced with an equimolar amount of B-9, b-6 with an equimolar amount of b-9, and c-6 with an equimolar amount of B-9, yielding compound 53 (17.44 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 605.2120 (theoretical value: 605.2103). Theoretical elemental content (%) C 42 H 27 N3O2: C, 83.29; H, 4.49; N, 6.94. Measured elemental content (%): C, 83.25; H, 4.52; N, 6.91.

[0199] Synthesis Example 6: Preparation of Compound 58

[0200]

[0201] Following the same preparation method as in Synthesis Example 1, B-6 was replaced with an equimolar amount of B-9, b-6 with an equimolar amount of b-58, and c-6 with an equimolar amount of B-9, yielding compound 58 (16.93 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 631.2272 (theoretical value: 631.2260). Theoretical elemental content (%) C 44 H 29N3O2: C, 83.66; H, 4.63; N, 6.65. Measured elemental content (%): C, 83.70; H, 4.60; N, 6.66.

[0202] Synthesis Example 7: Preparation of Compound 66

[0203]

[0204] Following the same preparation method as in Synthesis Example 1, B-6 was replaced with an equimolar amount of B-9, b-6 with an equimolar amount of b-66, and c-6 with an equimolar amount of B-9, yielding compound 66 (17.42 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 596.1860 (theoretical value: 596.1848). Theoretical elemental content (%) C 39 H 24 N4O3: C, 78.51; H, 4.05; N, 9.39. Measured elemental content (%): C, 78.55; H, 4.02; N, 9.40.

[0205] Synthesis Example 8: Preparation of Compound 106

[0206]

[0207] Following the same preparation method as in Synthesis Example 1, B-6 was replaced with an equimolar amount of B-106, b-6 with an equimolar amount of b-106, and c-6 with an equimolar amount of c-106, yielding compound 106 (15.71 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 530.1830 (theoretical value: 530.1817). Theoretical elemental content (%) C 37 H 26 N2S: C, 83.74; H, 4.94; N, 5.28. Measured elemental content (%): C, 83.76; H, 4.90; N, 5.31.

[0208] Synthesis Example 9: Preparation of Compound 122

[0209]

[0210] Following the same preparation method as in Synthesis Example 1, B-6 was replaced with an equimolar amount of B-122, b-6 with an equimolar amount of b-122, and c-6 with an equimolar amount of c-122, yielding compound 122 (16.82 g). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 656.2275 (theoretical value: 656.2286). Theoretical elemental content (%) C 47 H 32N2S: C, 85.94; H, 4.91; N, 4.26. Measured elemental content (%): C, 85.97; H, 4.87; N, 4.30.

[0211] Synthesis Example 10: Preparation of Compound 167

[0212]

[0213] Following the same preparation method as in Synthesis Example 1, B-6 was replaced with an equimolar amount of B-106, b-6 with an equimolar amount of b-167, and c-6 with an equimolar amount of B-106, yielding compound 167 (19.34 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 644.1177 (theoretical value: 644.1163). Theoretical elemental content (%) C 39 H 24 N4S3: C, 72.64; H, 3.75; N, 8.69. Measured elemental content (%): C, 72.69; H, 3.71; N, 8.72.

[0214] Synthesis Example 11: Preparation of Compound 192

[0215]

[0216] Following the same preparation method as in Synthesis Example 1, B-6 was replaced with an equimolar amount of B-192, and c-6 was replaced with an equimolar amount of B-192 to obtain compound 192 (18.63 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 705.2430 (theoretical value: 705.2416). Theoretical elemental content (%) C 50 H 31 N3O2: C, 85.09; H, 4.43; N, 5.95. Measured elemental content (%): C, 85.13; H, 4.40; N, 5.99.

[0217] Synthesis Example 12: Preparation of Compound 265

[0218]

[0219] Following the same preparation method as in Synthesis Example 1, B-6 was replaced with an equimolar amount of B-265, b-6 with an equimolar amount of b-265, and c-6 with an equimolar amount of B-265, yielding compound 265 (17.88 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 647.2277 (theoretical value: 647.2290). Theoretical elemental content (%) C 43 H 25D2N5O2: C, 79.74; H, 4.51; N, 10.81. Measured elemental content (%): C, 79.79; H, 4.48; N, 10.85.

[0220] Synthetic Example 13: Preparation of Compound 318

[0221]

[0222] Following the same preparation method as in Synthesis Example 1, B-6 was replaced with an equimolar amount of B-318, b-6 with an equimolar amount of b-318, and c-6 with an equimolar amount of B-318, yielding compound 318 (20.01 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 793.2540 (theoretical value: 793.2523). Theoretical elemental content (%) C 54 H 31 D4N3S2: C, 81.68; H, 4.95; N, 5.29. Measured elemental content (%): C, 81.72; H, 4.91; N, 5.32.

[0223] Synthesis Example 14: Preparation of Compound 333

[0224]

[0225] Following the same preparation method as in Synthesis Example 1, B-6 was replaced with an equimolar amount of B-333, b-6 with an equimolar amount of b-333, and c-6 with an equimolar amount of c-333, yielding compound 333 (16.15 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 568.2501 (theoretical value: 568.2515). Theoretical elemental content (%) C 41 H 32 N₂O: C, 86.59; H, 5.67; N, 4.93. Measured elemental content (%): C, 86.55; H, 5.63; N, 4.95.

[0226] Synthesis Example 15: Preparation of Compound 339

[0227]

[0228] Following the same preparation method as in Synthesis Example 1, B-6 was replaced with an equimolar amount of B-339, and c-6 was replaced with an equimolar amount of B-339 to obtain compound 339 (19.24 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 739.1852 (theoretical value: 739.1864). Theoretical elemental content (%) C 48 H 29N5S2: C, 77.92; H, 3.95; N, 9.47. Measured elemental content (%): C, 77.95; H, 3.91; N, 9.50.

[0229] Synthesis Example 16: Preparation of Compound 352

[0230]

[0231] Following the same preparation method as in Synthesis Example 1, B-6 was replaced with an equimolar amount of B-352, b-6 with an equimolar amount of b-352, and c-6 with an equimolar amount of c-352, yielding compound 352 (19.75 g). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 725.3469 (theoretical value: 725.3454). Theoretical elemental content (%) C 53 H 35 D5N2O: C, 87.69; H, 6.25; N, 3.86. Measured elemental content (%): C, 87.73; H, 6.21; N, 3.89.

[0232] Synthesis Example 17: Preparation of Compound 366

[0233]

[0234] Following the same preparation method as in Synthesis Example 1, B-6 was replaced with an equimolar amount of B-366, b-6 with an equimolar amount of b-366, and c-6 with an equimolar amount of c-366, yielding compound 366 (16.49 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 588.3130 (theoretical value: 588.3141). Theoretical elemental content (%) C 42 H 40 N₂O: C, 85.68; H, 6.85; N, 4.76. Measured elemental content (%): C, 85.72; H, 6.83; N, 4.79.

[0235] Synthesis Example 18: Preparation of Compound 375

[0236]

[0237] Following the same preparation method as in Synthesis Example 1, B-6 was replaced with an equimolar amount of B-9, b-6 with an equimolar amount of b-106, and c-6 with an equimolar amount of c-375, yielding compound 375 (18.44 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 622.2971 (theoretical value: 622.2984). Theoretical elemental content (%) C 45 H 38N₂O: C, 86.78; H, 6.15; N, 4.50. Measured elemental content (%): C, 86.81; H, 6.19; N, 4.52.

[0238] Synthesis Example 19: Preparation of Compound 376

[0239]

[0240] Following the same preparation method as in Synthesis Example 1, B-6 was replaced with an equimolar amount of B-9, b-6 with an equimolar amount of b-9, and c-6 with an equimolar amount of c-376, yielding compound 376 (18.17 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 698.3287 (theoretical value: 698.3297). Theoretical elemental content (%) C 51 H 42 N2O: C, 87.65; H, 6.06; N, 4.01. Measured elemental content (%): C, 87.69; H, 6.04; N, 4.05.

[0241] Synthesis Example 20: Preparation of Compound 387

[0242]

[0243] Following the same preparation method as in Synthesis Example 1, B-6 was replaced with an equimolar amount of B-387, b-6 with an equimolar amount of b-122, and c-6 with an equimolar amount of c-387, yielding compound 387 (17.01 g). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 574.2731 (theoretical value: 574.2719). Theoretical elemental content (%) C 40 H 18 D9N3O: C, 83.59; H, 6.31; N, 7.31. Measured elemental content (%): C, 83.55; H, 6.34; N, 7.29.

[0244] Synthesis Example 21: Preparation of Compound 406

[0245]

[0246] Following the same preparation method as in Synthesis Example 1, B-6 was replaced with an equimolar amount of B-406, b-6 with an equimolar amount of b-406, and c-6 with an equimolar amount of c-406, yielding compound 406 (18.28 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 702.3413 (theoretical value: 702.3424). Theoretical elemental content (%) C 51 H 22 D12 N₂O: C, 87.15; H, 6.59; N, 3.99. Measured elemental content (%): C, 87.19; H, 6.56; N, 4.01.

[0247] Synthesis Example 22: Preparation of Compound 416

[0248]

[0249] Following the same preparation method as in Synthesis Example 1, B-6 was replaced with an equimolar amount of B-416, b-6 with an equimolar amount of b-416, and c-6 with an equimolar amount of c-416, yielding compound 416 (19.12 g). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 746.3285 (theoretical value: 746.3297). Theoretical elemental content (%) C 55 H 42 N₂O: C, 88.44; H, 5.67; N, 3.75. Measured elemental content (%): C, 88.49; H, 5.64; N, 3.73.

[0250] Synthesis Example 23: Preparation of Compound 422

[0251]

[0252] Following the same preparation method as in Synthesis Example 1, B-6 was replaced with an equimolar amount of B-422, b-6 with an equimolar amount of b-422, and c-6 with an equimolar amount of c-422, yielding compound 422 (19.02 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 766.2971 (theoretical value: 766.2984). Theoretical elemental content (%) C 57 H 38 N₂O: C, 89.27; H, 4.99; N, 3.65. Measured elemental content (%): C, 89.30; H, 4.96; N, 3.66.

[0253] Synthesis Example 24: Preparation of Compound 424

[0254]

[0255] Following the same preparation method as in Synthesis Example 1, B-6 was replaced with an equimolar amount of B-424, b-6 with an equimolar amount of b-424, and c-6 with an equimolar amount of c-424, yielding compound 424 (18.90 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 694.3154 (theoretical value: 694.3165). Theoretical elemental content (%) C 49 H18 D 14 N₂S: C, 84.69; H, 6.67; N, 4.03. Measured elemental content (%): C, 84.67; H, 6.70; N, 4.07.

[0256] Synthesis Example 25: Preparation of Compound 431

[0257]

[0258] Following the same preparation method as in Synthesis Example 1, B-6 was replaced with an equimolar amount of B-9, b-6 with an equimolar amount of b-431, and c-6 with an equimolar amount of c-431, yielding compound 431 (17.74 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 642.1957 (theoretical value: 642.1943). Theoretical elemental content (%) C 45 H 26 N2O3: C, 84.10; H, 4.08; N, 4.36. Measured elemental content (%): C, 84.13; H, 4.04; N, 4.40.

[0259] Synthesis Example 26: Preparation of Compound 438

[0260]

[0261] Following the same preparation method as in Synthesis Example 1, B-6 was replaced with an equimolar amount of B-438, b-6 with an equimolar amount of b-431, and c-6 with an equimolar amount of c-438, yielding compound 438 (19.26 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 718.2270 (theoretical value: 718.2256). Theoretical elemental content (%) C 51 H 30 N2O3: C, 85.22; H, 4.21; N, 3.90. Measured elemental content (%): C, 85.24; H, 4.18; N, 3.94.

[0262] Synthesis Example 27: Preparation of Compound 467

[0263]

[0264] Following the same preparation method as in Synthesis Example 1, B-6 was replaced with an equimolar amount of B-9, b-6 with an equimolar amount of b-467, and c-6 with an equimolar amount of c-467, yielding compound 467 (18.51 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 642.1933 (theoretical value: 642.1943). Theoretical elemental content (%) C45 H 26 N2O3: C, 84.10; H, 4.08; N, 4.36. Measured elemental content (%): C, 84.14; H, 4.05; N, 4.40.

[0265] Synthesis Example 28: Preparation of Compound 544

[0266]

[0267] Following the same preparation method as in Synthesis Example 1, B-6 was replaced with an equimolar amount of B-544, b-6 with an equimolar amount of b-544, and c-6 with an equimolar amount of c-544, yielding compound 544 (17.70 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 650.2380 (theoretical value: 650.2392). Theoretical elemental content (%) C 45 H 34 N₂OS: C, 83.05; H, 5.27; N, 4.30. Measured elemental content (%): C, 83.08; H, 5.24; N, 4.33.

[0268] Synthesis Example 29: Preparation of Compound 585

[0269]

[0270] Following the same preparation method as in Synthesis Example 1, B-6 was replaced with an equimolar amount of B-585, b-6 with an equimolar amount of b-585, and c-6 with an equimolar amount of c-585, yielding compound 585 (17.84 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 675.1454 (theoretical value: 675.1439). Theoretical elemental content (%) C 44 H 25 N3OS2: C, 78.20; H, 3.73; N, 6.22. Measured elemental content (%): C, 78.23; H, 3.70; N, 6.26.

[0271] Synthesis Example 30: Preparation of Compound 630

[0272]

[0273] Following the same preparation method as in Synthesis Example 1, B-6 was replaced with an equimolar amount of B-9, b-6 with an equimolar amount of b-630, and c-6 with an equimolar amount of c-630, yielding compound 630 (15.84 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 542.1647 (theoretical value: 542.1630). Theoretical elemental content (%) C37 H 22 N2O3: C, 81.90; H, 4.09; N, 5.16. Measured elemental content (%): C, 81.93; H, 4.06; N, 5.20.

[0274] Synthesis Example 31: Preparation of Compound 641

[0275]

[0276] Following the same preparation method as in Synthesis Example 1, B-6 was replaced with an equimolar amount of B-9, b-6 with an equimolar amount of b-641, and c-6 with an equimolar amount of c-641, yielding compound 641 (18.06 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 694.2270 (theoretical value: 694.2256). Theoretical elemental content (%) C 49 H 30 N2O3: C, 84.71; H, 4.35; N, 4.03. Measured elemental content (%): C, 84.74; H, 4.31; N, 4.05.

[0277] Synthesis Example 32: Preparation of Compound 665

[0278]

[0279] Following the same preparation method as in Synthesis Example 1, b-6 was replaced with an equimolar amount of b-665, and c-6 was replaced with an equimolar amount of c-665, yielding compound 665 (16.03 g). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 556.2523 (theoretical value: 556.2509). Theoretical elemental content (%) C 37 H8D 14 N2O3: C, 79.83; H, 6.51; N, 5.03. Measured elemental content (%): C, 79.80; H, 6.54; N, 4.98.

[0280] Synthesis Example 33: Preparation of Compound 703

[0281]

[0282] Following the same preparation method as in Synthesis Example 1, B-6 was replaced with an equimolar amount of B-703, b-6 with an equimolar amount of b-703, and c-6 with an equimolar amount of c-703, yielding compound 703 (18.05 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 727.1764 (theoretical value: 727.1752). Theoretical elemental content (%) C 48 H29 N3OS2: C, 79.20; H, 4.02; N, 5.77. Measured elemental content (%): C, 79.23; H, 3.98; N, 5.81.

[0283] Synthesis Example 34: Preparation of Compound 723

[0284]

[0285] Following the same preparation method as in Synthesis Example 1, B-6 was replaced with an equimolar amount of B-9, b-6 with an equimolar amount of b-723, and c-6 with an equimolar amount of c-723, yielding compound 723 (19.28 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 764.3050 (theoretical value: 764.3039). Theoretical elemental content (%) C 54 H 40 N2O3: C, 84.79; H, 5.27; N, 3.66. Measured elemental content (%): C, 84.76; H, 5.31; N, 3.63.

[0286] Synthesis Example 35: Preparation of Compound 755

[0287]

[0288] Following the same preparation method as in Synthesis Example 1, B-6 was replaced with an equimolar amount of B-755, b-6 with an equimolar amount of b-431, and c-6 with an equimolar amount of c-585, yielding compound 755 (19.22 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 800.1943 (theoretical value: 800.1956). Theoretical elemental content (%) C 55 H 32 N₂OS₂: C, 82.47; H, 4.03; N, 3.50. Measured elemental content (%): C, 82.44; H, 4.07; N, 3.54.

[0289] Synthesis Example 36: Preparation of Compound 761

[0290]

[0291] Following the same preparation method as in Synthesis Example 1, B-6 was replaced with an equimolar amount of B-106, b-6 with an equimolar amount of b-66, and c-6 with an equimolar amount of c-761, yielding compound 761 (18.66 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 605.1523 (theoretical value: 605.1534). Theoretical elemental content (%) C 38 H19 D4N3OS2: C, 75.35; H, 4.49; N, 6.94. Measured elemental content (%): C, 75.39; H, 4.46; N, 6.98.

[0292] Synthesis Example 37: Preparation of Compound 770

[0293]

[0294] Following the same preparation method as in Synthesis Example 1, B-6 was replaced with an equimolar amount of B-9, b-6 with an equimolar amount of b-66, and c-6 with an equimolar amount of c-770, yielding compound 770 (17.82 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 645.2431 (theoretical value: 645.2416). Theoretical elemental content (%) C 45 H 31 N3O2: C, 83.70; H, 4.84; N, 6.51. Measured elemental content (%): C, 83.73; H, 4.80; N, 6.53.

[0295] Synthesis Example 38: Preparation of Compound 771

[0296]

[0297] Following the same preparation method as in Synthesis Example 1, B-6 was replaced with an equimolar amount of B-9, b-6 with an equimolar amount of b-771, and c-6 with an equimolar amount of c-771, yielding compound 771 (18.56 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 594.2658 (theoretical value: 594.2671). Theoretical elemental content (%) C 43 H 34 N₂O: C, 86.84; H, 5.76; N, 4.71. Measured elemental content (%): C, 86.88; H, 5.72; N, 4.75.

[0298] Synthesis Example 39: Preparation of Compound 772

[0299]

[0300] Following the same preparation method as in Synthesis Example 1, B-6 was replaced with an equimolar amount of B-106, b-6 with an equimolar amount of b-772, and c-6 with an equimolar amount of c-772, yielding compound 772 (20.86 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 854.2741 (theoretical value: 854.2756). Theoretical elemental content (%) C 63 H38 N2S: C, 88.49; H, 4.48; N, 3.28. Measured elemental content (%): C, 88.46; H, 4.52; N, 3.25.

[0301] Synthesis Exercise 40: Preparation of Compound 783

[0302]

[0303] Following the same preparation method as in Synthesis Example 1, B-6 was replaced with an equimolar amount of B-9, b-6 with an equimolar amount of b-66, and c-6 with an equimolar amount of c-783, yielding compound 783 (19.03 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 720.2542 (theoretical value: 720.2525). Theoretical elemental content (%) C 50 H 32 N4O2: C, 83.31; H, 4.47; N, 7.77. Measured elemental content (%): C, 83.28; H, 4.50; N, 7.81.

[0304] Synthetic Example 41: Preparation of Compound 785

[0305]

[0306] Following the same preparation method as in Synthesis Example 1, B-6 was replaced with an equimolar amount of B-9, b-6 with an equimolar amount of b-66, and c-6 with an equimolar amount of c-785, yielding compound 785 (17.79 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 694.2383 (theoretical value: 694.2369). Theoretical elemental content (%) C 48 H 30 N4O2: C, 82.98; H, 4.35; N, 8.06. Measured elemental content (%): C, 82.95; H, 4.40; N, 8.03.

[0307] Synthesis Example 42: Preparation of Compound 788

[0308]

[0309] Following the same preparation method as in Synthesis Example 1, B-6 was replaced with an equimolar amount of B-9, b-6 with an equimolar amount of b-9, and c-6 with an equimolar amount of c-788, yielding compound 788 (16.74 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 565.2167 (theoretical value: 565.2154). Theoretical elemental content (%) C 40 H 27N3O: C, 84.93; H, 4.81; N, 7.43. Measured elemental content (%): C, 84.97; H, 4.79; N, 7.46.

[0310] Synthesis Example 43: Preparation of Compound 795

[0311]

[0312] Following the same preparation method as in Synthesis Example 1, B-6 was replaced with an equimolar amount of B-9, b-6 with an equimolar amount of b-66, and c-6 with an equimolar amount of c-795, yielding compound 795 (17.17 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 557.1865 (theoretical value: 557.1852). Theoretical elemental content (%) C 36 H 23 N5O2: C, 77.54; H, 4.16; N, 12.56. Measured elemental content (%): C, 77.58; H, 4.12; N, 12.59.

[0313] Synthesis Example 44: Preparation of Compound 800

[0314]

[0315] Following the same preparation method as in Synthesis Example 1, B-6 was replaced with an equimolar amount of B-9, b-6 with an equimolar amount of b-800, and c-6 with an equimolar amount of c-800, yielding compound 800 (18.08 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 594.2683 (theoretical value: 594.2671). Theoretical elemental content (%) C 43 H 34 N₂O: C, 86.84; H, 5.76; N, 4.71. Measured elemental content (%): C, 86.87; H, 5.73; N, 4.72.

[0316] [Comparative Examples 1-3] Device Fabrication Examples:

[0317] Comparative Example 1: Fabrication of organic light-emitting devices using vacuum thermal evaporation. The experimental steps were as follows: ITO-Ag-ITO substrate was washed three times in distilled water, ultrasonically washed for 15 minutes, and after distilled water washing, it was ultrasonically washed in sequence with solvents such as isopropanol, acetone, and methanol, then dried at 120°C and sent to the evaporation machine.

[0318] On a prepared ITO-Ag-ITO transparent electrode, a hole injection layer HI / 50nm, a hole transport layer HT / 60nm, a light-emitting layer H₁₁ + Ir(piq)₂acac (96%:4% mass ratio) / 23nm were deposited by vacuum evaporation. Then, an electron transport layer TPBi:Liq (doping ratio 1:1 mass ratio) / 27nm, an electron injection layer LiF / 1nm, a cathode Mg-Ag / 18nm, and a capping layer CP₁ / 70nm were deposited on the cathode. The device was then sealed in a glove box, thus fabricating an organic light-emitting device. After completing the fabrication of the organic light-emitting device according to the above steps, the photoelectric performance of the device was measured. The molecular structural formulas of the relevant materials are shown below:

[0319]

[0320] Comparative Example 2: The capping material CP-1 in Comparative Example 1 was replaced with CP-2, and the organic light-emitting device of Comparative Example 2 was manufactured in the same manner as in Comparative Example 1.

[0321] Comparative Example 3: The capping material CP-1 in Comparative Example 1 was replaced with CP-3, and the organic light-emitting device of Comparative Example 3 was manufactured in the same manner as in Comparative Example 1.

[0322] [Application Examples 1-44]

[0323] Application Examples 1-43: The capping material CP-1 of the organic light-emitting device was sequentially replaced with compounds 6, 9, 38, 50, 53, 58, 66, 106, 122, 167, 192, 265, 318, 333, 339, 352, 366, 375, 376, 387, 406, 416, 422, 424, 431, 438, 467, 544, 585, 630, 641, 665, 703, 723, 755, 761, 770, 771, 772, 783, 785, 788, 795, and 800 of the present invention. All other steps were the same as in Comparative Example 1. The luminescence characteristics of the obtained organic light-emitting devices are shown in Table 1. Table 1 shows the luminescence characteristics of the light-emitting devices prepared with the compounds prepared in the examples of the present invention and the comparative substances.

[0324] [Table 1] Testing of the luminescent properties of light-emitting devices

[0325]

[0326]

[0327] Note: T97 refers to a current density of 10 mA / cm². 2Under these conditions, the time it takes for the device's brightness to decay to 97%;

[0328] As can be seen from the results in Table 1, the heterocyclic derivative of the present invention, when used as a capping material in organic light-emitting devices, can effectively improve the light extraction efficiency compared with comparative examples 1-3, thereby improving the luminous efficiency of organic light-emitting devices. In addition, it can also improve the lifetime of organic light-emitting devices, making it a high-performance capping material for organic light-emitting devices.

[0329] It should be noted that the present invention has been specifically described with reference to individual embodiments, but those skilled in the art can make various forms or details of improvements to the present invention without departing from the principles of the present invention, and these improvements also fall within the protection scope of the present invention.

Claims

1. An organic light-emitting device, comprising an anode, a cathode, and an organic layer, wherein the organic layer is located between the anode and the cathode or outside one or more electrodes of the anode and the cathode, characterized in that, The organic layer contains the structure shown in Formula I: X is selected from O or S; The L0 is selected from one of the following groups: The R p Selected from any one of hydrogen, deuterium, cyano, trifluoromethyl, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; or any two adjacent Rs. p Groups can bond together to form rings; The V values ​​may be the same or different, and each is independently selected from CR. b Or N, and at least one V is selected from N; when V is bonded to other groups, the V is selected from C; The R b Selected from any one of hydrogen, deuterium, cyano, trifluoromethyl, halogen, methyl, ethyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, adamantyl, phenyl, biphenyl, naphthyl, deuterated phenyl, deuterated biphenyl, deuterated naphthyl, pyridyl, pyrimidinyl, or two adjacent R groups. b They connect to form substituted or unsubstituted benzene rings; p1 is selected from 0, 1, 2, 3 or 4; The R a Whether identical or different, each is independently selected from one of hydrogen, deuterium, cyano, trifluoromethyl, halogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C20 heteroaryl, or optionally two adjacent R groups. a Groups can bond together to form rings; The 'a' is selected from 0, 1, 2, 3, 4, or 5; Ar1 and Ar2 may be the same as or different from each other, and are each independently selected from one of the following: substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring. L1 and L2 are independently selected from one of the following: single bond, substituted or unsubstituted C6-C25 arylene, and substituted or unsubstituted C2-C20 heteroarylene.

2. The organic light-emitting device according to claim 1, characterized in that, Formula I is selected from any of the following structures:

3. An organic light-emitting device according to claim 1, characterized in that, The L0 is selected from one of the following groups: Wherein, the R b The substituents, whether identical or different, are each independently selected from hydrogen, deuterium, cyano, trifluoromethyl, halogen, or substituted or unsubstituted groups of the following: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrimidinyl; wherein the substituents in "substituted or unsubstituted" are selected from one or more of deuterium, cyano, trifluoromethyl, halogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, deuterated phenyl, deuterated biphenyl, deuterated naphthyl, pyridyl, pyrimidinyl, and when substituted by multiple substituents, the multiple substituents are identical or different from each other; b1 is selected from 0, 1, 2, or 3; b2 is selected from 0, 1, or 2; b3 is selected from 0 or 1; b4 is selected from 0, 1, 2, 3, 4, or 5; b5 is selected from 0, 1, 2, 3, or 4; when b1, b2, b4, and b5 are greater than 1, two or more R... b They are the same or different from each other.

4. An organic light-emitting device according to claim 1, wherein the R a The same or different, each independently selected from hydrogen, deuterium, cyano, trifluoromethyl, halogen, substituted or unsubstituted methyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, or optionally two adjacent R groups. a Groups can bond together to form benzene rings or naphthalene rings; The value of 'a' is selected from 0, 1, 2, 3, 4, or 5.

5. An organic light-emitting device according to claim 1, characterized in that, In formula I Selected from one of the following groups: X is selected from O or S.

6. The organic light-emitting device according to claim 1, wherein Ar1 and Ar2 are the same or different from each other, and each is independently selected from one of the following groups: In formula a, R1 is selected from one of hydrogen, deuterium, cyano, trifluoromethyl, halogen, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, and substituted or unsubstituted C3-C25 heteroaryl. The n1 is selected from 0, 1, 2, 3, 4 or 5; when n1 is greater than 1, each R1 is the same or different, and two adjacent R1 groups can be bonded together to form a substituted or unsubstituted cyclic structure. In formula b, X is selected from O, S, C(R) c (R) d Any one of N(R); The R c R d Whether identical or different, each is independently selected from any one of hydrogen, deuterium, cyano, trifluoromethyl, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or R c R d They can combine to form substituted or unsubstituted spirorings; or R c R d Either of them can be directly bonded to L1 or L2; R is selected from any one of deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or R can be directly bonded to L1 or L2. R2 and R3 may be the same or different, and each is independently selected from any one of hydrogen, deuterium, cyano, trifluoromethyl, halogen, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, and substituted or unsubstituted C6-C25 aryl. The n2 is selected from 0, 1, 2, 3 or 4; when n2 is greater than 1, each R2 is the same or different, and two adjacent R2 groups can be bonded together to form a substituted or unsubstituted cyclic structure; the n3 is selected from 0, 1, 2, 3 or 4; when n3 is greater than 1, each R3 is the same or different, and two adjacent R3 groups can be bonded together to form a substituted or unsubstituted cyclic structure. In formula c, the z that are the same or different are selected from CR. z Or N, and 1-4 z are selected from N; when z is bonded to other groups, z is selected from C; The R z They may be the same or different, and are each independently selected from any one of hydrogen, deuterium, cyano, trifluoromethyl, halogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, and substituted or unsubstituted pyridazinyl. The n4 is selected from 0, 1, 2, 3 or 4; when n4 is greater than 1, each R4 is the same or different, and two adjacent R4 groups can bond together to form a substituted or unsubstituted cyclic structure.

7. An organic light-emitting device according to claim 1, characterized in that, The Ar1 and Ar2 may be the same as or different from each other, and each is independently selected from one of the following groups: R1 is selected from one of hydrogen, deuterium, cyano, trifluoromethyl, halogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, and substituted or unsubstituted naphthyl. R2 and R3 are independently selected from one of hydrogen, deuterium, cyano, trifluoromethyl, halogen, methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornel, phenyl, naphthyl, tolyl, biphenyl, terphenyl, anthracene, phenanthrene, phenylenetriethylene, spirofluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, dibenzofuranyl, dibenzothiopheneyl, 9-phenylcarbazoyl, and carbazoyl. Furthermore, R2 and R3 can also be replaced by deuterium, cyano, trifluoromethyl, or halogen. The benzene ring is substituted with one or more of the following: methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, tolyl, biphenyl, deuterated biphenyl, terphenyl, anthracene, phenanthrene, and triphenylene; in the case of multiple substituents, the multiple substituents are the same or different from each other; or any two adjacent R2s combine with each other to form a substituted or unsubstituted benzene ring or naphthalene ring; or any two adjacent R3s combine with each other to form a substituted or unsubstituted benzene ring or naphthalene ring. The R c R d R5 is independently selected from hydrogen, deuterium, cyano, trifluoromethyl, halogen, and any one of the following groups, substituted or unsubstituted: C1-C6 alkyl, C3-C6 cycloalkyl, adamantyl, norbornel, C6-C12 aryl, and C2-C12 heteroaryl; wherein the "substituted or unsubstituted" substituent is any one or more of deuterium, C1-C12 alkyl, and C3-C12 cycloalkyl. The R is selected from deuterium, cyano, trifluoromethyl, halogen, or substituted or unsubstituted groups of the following: methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornel, phenyl, naphthyl, anthracene, phenanthrene, triphenylene, dibenzofuranyl, dibenzothiophene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirofluorenyl, and 9-phenylcarbazoyl. The R4 is selected from one of hydrogen, deuterium, cyano, trifluoromethyl, halogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, and substituted or unsubstituted naphthyl. The m1 is selected from 0, 1, 2, 3, 4 or 5; the m2 is selected from 0, 1, 2, 3 or 4; the m3 is selected from 0, 1, 2 or 3; the m4 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the m5 is selected from 0, 1 or 2; the m6 is selected from 0, 1, 2, 3, 4, 5 or 6; the m7 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; the m8 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; the m9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12 or 13.

8. An organic light-emitting device according to claim 1, characterized in that, L1 and L2 are independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted anthraceneylene, substituted or unsubstituted phenanthylene, substituted or unsubstituted terphenylene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothiopheneylene, substituted or unsubstituted benzofuranylene, substituted or unsubstituted benzothiopheneylene, substituted or unsubstituted fluoreneylene, substituted or unsubstituted carbazolylene, substituted or unsubstituted pyridylene, and so on. The substituted or unsubstituted pyrimidinyl group, the substituted or unsubstituted triazine group, the substituted or unsubstituted pyridazine group, the substituted or unsubstituted pyrazine group, the substituted or unsubstituted quinolinyl group, the substituted or unsubstituted isoquinolinyl group, the substituted or unsubstituted quinazolinyl group, the substituted or unsubstituted quinoxalinyl group, the substituted or unsubstituted phthalazine group, the substituted or unsubstituted naphthinyl group, the substituted or unsubstituted benzocyclopentyl group, the substituted or unsubstituted benzocyclohexyl group, the substituted or unsubstituted benzocyclopentenyl group, the substituted or unsubstituted benzocyclohexenyl group, or any combination thereof.

9. An organic light-emitting device according to claim 1, characterized in that, The structure represented by Formula I is selected from any one of the following chemical structures:

10. An organic light-emitting device according to claim 1, wherein the organic layer comprises a hole transport region, a light-emitting layer, an electron transport region, and a capping layer, characterized in that, The covering layer contains any one or a combination of at least two of the structures described in any one of claims 1 to 9.

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