Heterocyclic compound and organic electroluminescent device thereof

Abstract

The application relates to the technical field of organic photoelectric materials, in particular to a heterocyclic compound and an organic electroluminescent device thereof. The application provides a heterocyclic compound which has a higher triplet energy level than a light-emitting substance, proper HOMO and LUMO and good electron migration capacity, can improve the light-emitting efficiency of a device, reduce the driving voltage of the device and prolong the service life of the device, and is a kind of excellent OLED material.

Description

Technical Field

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

[0002] Organic light-emitting diodes (OLEDs) have the characteristics of being thin and light, having a wide viewing angle, fast response, wide operating temperature range, low energy consumption, high efficiency, good color purity, high definition, and good flexibility. They have been widely used in the lighting and display fields and are considered by the industry to be one of the most promising display and lighting technologies.

[0003] Classic OLED devices have a "sandwich" structure, with an emissive layer sandwiched between two electrodes: a cathode and an anode. This emissive layer contains a luminescent material (guest material). When a specific operating voltage is applied between the two electrodes, holes and electrons are injected from the anode and cathode respectively, reaching the emissive layer. There, they recombine to generate excitons, releasing energy. Under the influence of an electric field, the excitons migrate, transferring energy to the luminescent material. Electrons in the luminescent material molecules transition from the ground state to an excited state, and then return from the unstable excited state to the stable ground state, releasing energy as light, thus producing luminescence. To improve device performance, more organic functional layers are placed between the anode and the emissive layer, and between the cathode and the emissive layer. Generally, the region between the anode and the emissive layer is a hole transport region, responsible for injecting and transporting holes, including hole injection layers, hole transport layers, luminescent auxiliary layers, and electron blocking layers. The region between the cathode and the emissive layer is an electron transport region, responsible for injecting and transporting electrons, including electron injection layers, electron transport layers, and hole blocking layers.

[0004] Generally, the luminescent layer includes not only the luminescent material but also the host material, which primarily transfers energy to the luminescent material. This requires the host material's T1 (triple-state energy level) to be higher than that of the luminescent material, typically greater than 2.75 eV. This ensures that the energy exchange between the host material and the luminescent material is exothermic, preventing the luminescent material from transferring energy back to the host material. Furthermore, the host material's highest occupied orbital (HOMO) and lowest unoccupied orbital (LUMO) levels must match those of other adjacent organic functional layers in the device to facilitate hole and electron injection. Simultaneously, the singlet and triplet energy levels of the molecules should be relatively close to reduce the driving voltage. The host material molecules also need to possess good carrier transport characteristics to allow for efficient recombination of holes and electrons. Other organic functional layers also generally require appropriate energy level matching and carrier transport capabilities. For example, the organic functional layers in the electron transport region need good energy level matching with adjacent organic functional layers and also require good electron transport capabilities.

[0005] To further improve the performance of OLED devices, such as driving voltage, luminous efficiency, color purity, and lifespan, it is still necessary to develop host materials and electron transport materials with superior performance. Summary of the Invention

[0006] To address the aforementioned technical problems, this invention provides a heterocyclic compound possessing appropriate triplet energy levels, HOMO and LUMO, excellent carrier transport capability, and good thermal and chemical stability. It can be used as a host material or electron transport material in OLED devices, thereby effectively improving the luminous efficiency, driving voltage, and lifespan of OLED devices. The compound has one of the structures shown in formulas (IA) to (IC).

[0007]

[0008] Wherein, X1 is selected from oxygen atom, sulfur atom or NR1, and R1 is selected from one of hydrogen atom, deuterium atom, substituted or unsubstituted C1 to C12 alkyl, substituted or unsubstituted C3 to C10 cycloalkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heteroaryl each time it appears;

[0009] The X2 is selected from oxygen atoms or sulfur atoms;

[0010] The A mentioned above is selected from one of the structures shown in formulas (A-1) to (A-10):

[0011]

[0012] In formulas (A-1) to (A-2), Y1 to Y6 are independently selected from CR2 or nitrogen atoms, and at most four are selected from nitrogen atoms; one of Y1 to Y6 is connected to L and is selected from carbon atoms; in formulas (A-3) to (A-8), Y1 to Y8 are independently selected from CR2 or nitrogen atoms, and at most four are selected from nitrogen atoms; one of Y1, Y2, Y5 to Y8 is connected to L and is selected from carbon atoms; in formulas (A-9) to (A-10), Y1 to Y6 are independently selected from CR2 or nitrogen atoms, and at most four are selected from nitrogen atoms; one of Y1, Y2, Y5 to Y8 is connected to L and is selected from carbon atoms; 10 The atoms are independently selected from CR2 or nitrogen atoms, and at most four are selected from nitrogen atoms, wherein Y1 to Y... 10 One of them is connected to L and is selected from carbon atoms; each time R2 appears, it is selected from one of hydrogen atoms, deuterium atoms, halogen atoms, cyano groups, substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C3-C10 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, and substituted or unsubstituted C2-C30 heteroaryl groups, either the same or different.

[0013] The Ar1 is selected from one of hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C6-C30 aryl group, and substituted or unsubstituted C2-C30 heteroaryl group;

[0014] The Ar2 is selected from one of the following: hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C10 cycloalkyl group, substituted or unsubstituted C6-C30 aryl group, and substituted or unsubstituted C2-C30 heteroaryl group.

[0015] The L is selected from one of substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C2-C30 heteroaryl groups; the substituent in "substituted or unsubstituted" is selected from one or more of the following: deuterium atom; cyano group; halogen atom; C1-C10 alkyl group substituted or unsubstituted by one or more of the group consisting of deuterium atom, cyano group, and halogen atom; C6-C12 aryl group substituted or unsubstituted by one or more of the group consisting of deuterium atom, cyano group, halogen atom, and C1-C4 alkyl group; C2-C10 heteroaryl group substituted or unsubstituted by one or more of the group consisting of deuterium atom, cyano group, halogen atom, and C1-C4 alkyl group.

[0016] The X3 is selected from CR3 or a nitrogen atom, and the R3 is selected from one of hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C10 cycloalkyl group, substituted or unsubstituted C6-C30 aryl group, and substituted or unsubstituted C2-C30 heteroaryl group.

[0017] The B mentioned is selected from one of the structures shown in formulas (B-1) to (B-11):

[0018]

[0019] In formula (B-1), Z1 to Z4 are independently selected from CR4 or nitrogen atoms, and at most three are selected from nitrogen atoms; in formula (IC), one of Z1 to Z4 is connected to L and is selected from carbon atoms; in formulas (B-2) to (B-3), Z1 to Z6 are independently selected from CR4 or nitrogen atoms, and at most four are selected from nitrogen atoms; in formula (IC), one of Z3 to Z6 is connected to L and is selected from carbon atoms; in formulas (B-4) to (B-9), Z1 to Z8 are independently selected from CR4 or nitrogen atoms, and at most four are selected from nitrogen atoms; in formula (IC), one of Z3 to Z8 is connected to L and is selected from carbon atoms; in formulas (B-10) to (B-11), Z1 to Z6 are independently selected from CR4 or nitrogen atoms, and at most four are selected from nitrogen atoms; in formula (IC), one of Z3 to Z8 is connected to L and is selected from carbon atoms; in formulas (B-10) to (B-11), Z1 to Z6 are independently selected from CR4 or nitrogen atoms, and at most three ... 10 Independently selected from CR4 or nitrogen atoms, and at most four selected from nitrogen atoms, in formula (IC), Z3 to Z... 10 One of them is connected to L and is selected from carbon atoms; each time R4 appears, it is selected from one of hydrogen atoms, deuterium atoms, halogen atoms, cyano groups, substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C3-C10 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, and substituted or unsubstituted C2-C30 heteroaryl groups, either the same or different.

[0020] The present invention also provides an organic electroluminescent device, comprising an anode, a cathode, and an organic layer, wherein the organic layer comprises at least one of a hole transport region between the anode and the cathode, a light-emitting layer, an electron transport region, and a capping layer on the side of the cathode opposite to the anode, and the organic layer contains one or more of the heterocyclic compounds described in the present invention.

[0021] Beneficial effects:

[0022] The heterocyclic compounds represented by formulas (IA) to (IC) provided by this invention have higher triplet energy levels than the luminescent material. When used as host materials in OLED devices, they facilitate the transfer of energy from the host material to the luminescent material without the phenomenon of energy returning from the guest material to the host material. They also possess appropriate HOMO and LUMO properties, enabling them to match well with adjacent organic functional layers, effectively reducing energy loss, thereby improving the luminous efficiency of the device, reducing the driving voltage, and extending the device's lifespan. Furthermore, the heterocyclic compounds exhibit excellent electron mobility. When used as host materials or electron transport materials, combined with appropriate hole transport materials or other host materials, they can improve electron transport efficiency and promote the recombination of electrons and holes in the luminescent layer, further enhancing the device's luminous efficiency. The heterocyclic compounds also exhibit excellent thermal and chemical stability, delaying device aging and further extending the device's lifespan even under high-temperature and corrosive gas operating environments.

[0023] In summary, the heterocyclic compounds provided by the invention are a class of high-performance OLED materials. Detailed Implementation

[0024] The technical solutions of this invention will be clearly and completely described below with reference to specific embodiments. Obviously, the described embodiments are only some embodiments of this invention, and not all embodiments. Based on the embodiments of this invention, all other embodiments obtained by those skilled in the art without creative effort are within the protection scope of this invention.

[0025] 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.

[0026] The halogen atom mentioned in this invention refers to fluorine, chlorine, bromine, and iodine atoms.

[0027] 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.

[0028] 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 5 to 10 carbon atoms. Examples may include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane, etc., but are not limited thereto. The aforementioned cycloalkyl group is preferably cyclopentane, cyclohexane, cyclopentenyl, 1-adamantane, 2-adamantane, or norbornane.

[0029] The cycloalkenyl group described in this invention refers to a hydrocarbon group formed by removing one hydrogen atom from a cycloalkene molecule, preferably having 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, and particularly preferably 5 to 10 carbon atoms. Examples may include cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, etc., but are not limited thereto. The aforementioned cycloalkyl groups are preferably cyclopentenyl or cyclohexenyl.

[0030] The heterocyclic alkyl group described in this invention refers to a group formed by removing one hydrogen atom from a heterocyclic molecule that contains at least one heteroatom in addition to carbon atoms. Heteroatoms include nitrogen, oxygen, sulfur, silicon, selenium, and phosphorus atoms, preferably nitrogen, oxygen, or sulfur. It is preferable to contain 1 to 3 heteroatoms, more preferably 1 to 2 heteroatoms, and particularly preferably 1 heteroatom. It is preferable to have 3 to 15 ring atoms, more preferably 3 to 12 ring atoms, and particularly preferably 5 to 6 ring atoms. Examples may include ethylene oxide, cyclothioethylene, propylidinyl, tetrahydropyrrolyl, piperidinyl, morpholinyl, thiomorpholinyl, piperazine, etc., but are not limited thereto. The aforementioned heterocyclic groups are preferably tetrahydropyrrolyl, piperidinyl, morpholinyl, thiomorpholinyl, or piperazine.

[0031] The aryl group mentioned in this invention refers to the general term for the 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, fused-ring aryl, or a fused group of aryl and aliphatic ring. It preferably has 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 group refers to an aryl group with only one aromatic ring in the molecule, such as phenyl, but not limited to this; the polycyclic aryl group refers to an aryl group with two or more independent aromatic rings in the molecule, such as biphenyl, terphenyl, etc., but not limited to this; the fused-ring aryl group refers to an aryl group with two or more aromatic rings in the molecule that are fused together by sharing two adjacent carbon atoms, such as naphthyl, anthracene, phenanthryl, pyrene, peryl, fluorenyl, benzo[a]fluorenyl, triphenylene, fluoranyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-adamantyl-fluorenyl, spiro-cyclopentenyl-fluorenyl, spiro-cyclohexenyl-fluorenyl, etc., but not limited to this. The aryl group is preferably phenyl, biphenyl, terphenyl, 1-naphthyl, 2-naphthyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-adamantyl-fluorenyl, spiro-cyclopentenyl-fluorenyl, or spiro-cyclohexenyl-fluorenyl.

[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. The heteroatoms include, but are not limited to, oxygen, sulfur, nitrogen, silicon, selenium, 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.

[0033] In this invention, the term arylene refers to an aryl group having two bonding sites, i.e., a divalent group. The above description of aryl groups can be applied to it, the difference being that arylene is a divalent group.

[0034] In this invention, the term "hybrid aryl" refers to a heteroaryl group having two bonding sites, i.e., a divalent group. The above description of heteroaryl groups can be applied to it, the difference being that the hybrid aryl group is a divalent group.

[0035] The term "substitution" as used in this invention refers to the replacement of a hydrogen atom in certain functional groups by another atom or functional group (i.e., a substituent), and the position of substitution is not limited, as long as the position is where the hydrogen atom is substituted. Furthermore, when two or more are substituted, the two or more substituents may be the same as or different from each other.

[0036] In this invention, "substituted or unsubstituted" means either unsubstituted or substituted by one or more substituents selected from the group consisting of: deuterium, halogen, amino, cyano, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 cycloalkenyl, substituted or unsubstituted C3-C30 heterocyclic, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C2-C60 heteroaryl, silyl, preferably deuterium, halogen, cyano, nitro, C1-C12 alkyl, C3-C12 alkyl, halogen, cycloalkyl ... Cycloalkyl, C3-C12 cycloalkenyl, C3-C12 heterocyclic, C6-C30 aryl, C3-C30 heteroaryl, silyl, when substituted with multiple substituents, the multiple substituents may be the same or different from each other; preferably, it means unsubstituted or substituted with one or more substituents selected from the group consisting of: deuterium, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, trifluoromethyl, deuterated methyl, ethyl, deuterated ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, deuterated tert-butyl, cyclopropane, methyl-substituted cyclopropane, ethyl-substituted cyclopropane, deuterated cyclopropane, cyclobutane, methyl-substituted cyclobutane, ethyl-substituted cyclobutane Alkyl, deuterated cyclobutyl, cyclopentyl, methyl-substituted cyclopentyl, ethyl-substituted cyclopentyl, deuterated cyclopentyl, cyclohexyl, methyl-substituted cyclohexyl, ethyl-substituted cyclohexyl, n-propyl-substituted cyclohexyl, n-butyl-substituted cyclohexyl, cyclohexane-substituted cyclohexyl, deuterated cyclohexyl, cycloheptyl, cyclopentenyl, methyl-substituted cyclopentenyl, ethyl-substituted cyclopentenyl, cyclohexenyl, cycloheptenyl, adamantyl, methyl-substituted adamantyl, ethyl-substituted adamantyl, deuterated adamantyl, norbornyl, methyl-substituted norbornyl, ethyl-substituted norbornyl, deuterated norbornyl, tetrahydropyrrolyl, piperidinyl, morpholinyl, thiomorpholinyl, methyl-substituted piperazineyl, Ethyl-substituted piperazine, phenyl-substituted piperazine, naphthyl-substituted piperazine, methoxy, ethoxy, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, anthracene, deuterated anthracene, phenanthrene, deuterated phenanthrene, triphenylene, pyrene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-adamantyl-fluorenyl, spiro-cyclopentenyl-fluorenyl, spiro-cyclohexenyl-fluorenyl, pyridyl, pyrimidinyl, triazine, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, N-phenylcarbazoyl, dibenzofuranyl, dibenzothiopheneyl, trimethylsilyl, triphenylsilyl, where the multiple substituents are the same or different from each other.

[0037] In this specification, when the position of a substituent or linking site on the aromatic ring is not fixed, it means that it can be linked to any of the optional sites on the aromatic ring. For example, Can represent And so on.

[0038] In this specification, when a substituent or linking site lies within a bond that extends through two or more rings, it indicates that the substituent or linking site can be linked to any one of the two or more rings, specifically to any one of the corresponding optional sites within the rings. For example, Can represent Can represent And so on.

[0039] The linked ring structure described in this invention (e.g., forming saturated or unsaturated C3-C10 carbon rings, forming substituted or unsubstituted saturated or unsaturated C3-C6 carbon rings) refers to the individual groups being connected to each other by chemical bonds, optionally forming double / triple bonds, and can constitute aromatic groups, as shown in the following examples:

[0040]

[0041] This invention provides a heterocyclic compound having one of the structures shown in formulas (IA) to (IC):

[0042]

[0043] Wherein, X1 is selected from oxygen atom, sulfur atom or NR1, and R1, each time it appears, is selected from one of hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C10 cycloalkyl group, substituted or unsubstituted C6-C30 aryl group or substituted or unsubstituted C2-C30 heteroaryl group;

[0044] The X2 is selected from oxygen atoms or sulfur atoms;

[0045] Wherein, X1 is selected from oxygen atom, sulfur atom or NR1, and R1, each time it appears, is selected from one of hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C10 cycloalkyl group, substituted or unsubstituted C6-C30 aryl group or substituted or unsubstituted C2-C30 heteroaryl group;

[0046] The X2 is selected from oxygen atoms or sulfur atoms;

[0047] The A mentioned above is selected from one of the structures shown in formulas (A-1) to (A-10):

[0048]

[0049] In formulas (A-1) to (A-2), Y1 to Y6 are independently selected from CR2 or nitrogen atoms, and at most four are selected from nitrogen atoms; one of Y1 to Y6 is connected to L and is selected from carbon atoms; in formulas (A-3) to (A-8), Y1 to Y8 are independently selected from CR2 or nitrogen atoms, and at most four are selected from nitrogen atoms; one of Y1, Y2, Y5 to Y8 is connected to L and is selected from carbon atoms; in formulas (A-9) to (A-10), Y1 to Y6 are independently selected from CR2 or nitrogen atoms, and at most four are selected from nitrogen atoms; one of Y1, Y2, Y5 to Y8 is connected to L and is selected from carbon atoms; 10 The atoms are independently selected from CR2 or nitrogen atoms, and at most four are selected from nitrogen atoms, wherein Y1 to Y... 10 One of them is connected to L and is selected from carbon atoms; each time R2 appears, it is selected from one of hydrogen atoms, deuterium atoms, halogen atoms, cyano groups, substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C3-C10 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, and substituted or unsubstituted C2-C30 heteroaryl groups, either the same or different.

[0050] The Ar1 is selected from one of hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C6-C30 aryl group, and substituted or unsubstituted C2-C30 heteroaryl group;

[0051] The Ar2 is selected from one of the following: hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C10 cycloalkyl group, substituted or unsubstituted C6-C30 aryl group, and substituted or unsubstituted C2-C30 heteroaryl group.

[0052] The L is selected from one of substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C2-C30 heteroaryl groups; the substituent in "substituted or unsubstituted" is selected from one or more of the following: deuterium atom; cyano group; halogen atom; C1-C10 alkyl group substituted or unsubstituted by one or more of the group consisting of deuterium atom, cyano group, and halogen atom; C6-C12 aryl group substituted or unsubstituted by one or more of the group consisting of deuterium atom, cyano group, halogen atom, and C1-C4 alkyl group; C2-C10 heteroaryl group substituted or unsubstituted by one or more of the group consisting of deuterium atom, cyano group, halogen atom, and C1-C4 alkyl group.

[0053] The X3 is selected from CR3 or a nitrogen atom, and the R3 is selected from one of hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C10 cycloalkyl group, substituted or unsubstituted C6-C30 aryl group, and substituted or unsubstituted C2-C30 heteroaryl group.

[0054] The B mentioned is selected from one of the structures shown in formulas (B-1) to (B-11):

[0055]

[0056] In formula (B-1), Z1 to Z4 are independently selected from CR4 or nitrogen atoms, and at most three are selected from nitrogen atoms; in formula (IC), one of Z1 to Z4 is connected to L and is selected from carbon atoms; in formulas (B-2) to (B-3), Z1 to Z6 are independently selected from CR4 or nitrogen atoms, and at most four are selected from nitrogen atoms; in formula (IC), one of Z3 to Z6 is connected to L and is selected from carbon atoms; in formulas (B-4) to (B-9), Z1 to Z8 are independently selected from CR4 or nitrogen atoms, and at most four are selected from nitrogen atoms; in formula (IC), one of Z3 to Z8 is connected to L and is selected from carbon atoms; in formulas (B-10) to (B-11), Z1 to Z6 are independently selected from CR4 or nitrogen atoms, and at most four are selected from nitrogen atoms; in formula (IC), one of Z3 to Z8 is connected to L and is selected from carbon atoms; in formulas (B-10) to (B-11), Z1 to Z6 are independently selected from CR4 or nitrogen atoms, and at most three ... 10 Independently selected from CR4 or nitrogen atoms, and at most four selected from nitrogen atoms, in formula (IC), Z3 to Z... 10 One of them is connected to L and is selected from carbon atoms; each time R4 appears, it is selected from one of hydrogen atoms, deuterium atoms, halogen atoms, cyano groups, substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C3-C10 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, and substituted or unsubstituted C2-C30 heteroaryl groups, either the same or different.

[0057] Preferably, the substituent in "substituted or unsubstituted" is selected from deuterium atom; halogen atom; cyano group; C1-C12 alkyl group substituted or unsubstituted by one or more of the group consisting of deuterium atom, halogen atom, cyano group, C1-C4 alkyl group, C6-C20 aryl group, and C2-C20 heteroaryl group; or C1-C12 alkyl group substituted or unsubstituted by one or more of the group consisting of deuterium atom, halogen atom, cyano group, C1-C4 alkyl group, C6-C20 aryl group, and C2-C20 heteroaryl group. Substituted C3-C12 cycloalkyl groups; C3-C12 cycloalkenyl groups substituted or unsubstituted with one or more of the following groups: deuterium atom, halogen atom, cyano group, C1-C4 alkyl group, C6-C20 aryl group, and C2-C20 heteroaryl group; heterocyclic alkyl groups with 3 to 12 ring atoms substituted or unsubstituted with one or more of the following groups: deuterium atom, halogen atom, cyano group, C1-C4 alkyl group, C6-C20 aryl group, and C2-C20 heteroaryl group; A C6-C30 aryl group substituted or unsubstituted with one or more of the following groups: deuterium atom, halogen atom, cyano group, C1-C4 alkyl group, C6-C20 aryl group, and C2-C20 heteroaryl group; a C3-C30 heteroaryl group substituted or unsubstituted with one or more of the following groups: deuterium atom, halogen atom, cyano group, C1-C4 alkyl group, C6-C20 aryl group, and C2-C20 heteroaryl group; a C3-C30 heteroaryl group substituted or unsubstituted with one or more of the following groups: deuterium atom, halogen atom, cyano group, C1-C4 alkyl group, C6-C20 aryl group, and C2-C20 heteroaryl group; The alkyl group comprises one or more substituted or unsubstituted silyl groups from the group consisting of 6-C20 aryl groups and C2-C20 heteroaryl groups, wherein the heterocyclic alkyl or heteroaryl group contains at least one of O, S, N, Si, Se, and P, and the substituent is one or more. When there are multiple substituents, the multiple substituents may be the same or different. When multiple substituents are present, two adjacent substituents may optionally be linked to form a saturated or unsaturated C3-C10 carbon ring.

[0058] Preferably, the substituents in "substituted or unsubstituted" are selected from the group consisting of deuterium atom; fluorine atom; cyano; methyl; trifluoromethyl; deuterated methyl; ethyl; deuterated ethyl; n-propyl; isopropyl; deuterated isopropyl; n-butyl; sec-butyl; isobutyl; tert-butyl; deuterated tert-butyl; cyclopropane groups substituted or unsubstituted by one or more of the group consisting of deuterium atom, fluorine atom, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, phenyl, deuterated phenyl, pentafluorophenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl; and cyclopropane groups substituted or unsubstituted by one of the group consisting of deuterium atom, fluorine atom, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, phenyl, deuterated phenyl, pentafluorophenyl, and deuterated biphenyl. Cyclobutyl groups substituted or unsubstituted with one or more of the groups consisting of fluorophenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl; cyclobutyl groups substituted or unsubstituted with one or more of the groups consisting of deuterium, fluorine, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, phenyl, deuterated phenyl, pentafluorophenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl; cyclohex ... with one or more of the groups consisting of deuterium, Cyclopropene group substituted or unsubstituted with one or more of the group consisting of fluorine atom, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, phenyl, deuterated phenyl, pentafluorophenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl; cyclobutenyl group substituted or unsubstituted with one or more of the group consisting of deuterium atom, fluorine atom, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, phenyl, deuterated phenyl, pentafluorophenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl; cyclobutenyl group substituted or unsubstituted with one or more of the group consisting of deuterium atom, fluorine atom, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, phenyl, and deuterated... Cyclopentenyl groups substituted or unsubstituted with one or more of the group consisting of phenyl, pentafluorophenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl; cyclohexenyl groups substituted or unsubstituted with one or more of the group consisting of deuterium, fluorine, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, phenyl, deuterated phenyl, pentafluorophenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl; adamantyl groups substituted or unsubstituted with one or more of the group consisting of deuterium, fluorine, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, phenyl, deuterated phenyl, pentafluorophenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl;The norborneol alkyl group substituted or unsubstituted by one or more of the group consisting of deuterium atom, fluorine atom, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, phenyl, deuterated phenyl, pentafluorophenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl; the tetrahydropyrrole group substituted or unsubstituted by one or more of the group consisting of deuterium atom, fluorine atom, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, phenyl, deuterated phenyl, pentafluorophenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl; the tetrahydropyrrole group substituted or unsubstituted by one of the group consisting of deuterium atom, fluorine atom, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, and deuterated tert-butyl. Piperidinyl groups substituted or unsubstituted with one or more of the group consisting of methyl, phenyl, deuterated phenyl, pentafluorophenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl; morpholinyl groups substituted or unsubstituted with one or more of the group consisting of deuterium, fluorine, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, phenyl, deuterated phenyl, pentafluorophenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl; sulfur groups substituted or unsubstituted with one or more of the group consisting of deuterium, fluorine, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, phenyl, deuterated phenyl, pentafluorophenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl. The following are substituted or unsubstituted piperazine groups: morpholinoyl; substituted or unsubstituted piperazine groups: ... Naphthyl groups substituted or unsubstituted with one or more of the group consisting of methyl, phenyl, deuterated phenyl, pentafluorophenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl; anthracene groups substituted or unsubstituted with one or more of the group consisting of deuterium, fluorine, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, phenyl, deuterated phenyl, pentafluorophenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl; phenanthrene groups substituted or unsubstituted with one or more of the group consisting of deuterium, fluorine, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, phenyl, deuterated phenyl, pentafluorophenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl;A triphenylene group substituted or unsubstituted with one or more of the following groups: deuterium atom, fluorine atom, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, phenyl, deuterated phenyl, pentafluorophenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl; a fluorene group substituted or unsubstituted with one or more of the following groups: deuterium atom, fluorine atom, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, phenyl, deuterated phenyl, pentafluorophenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl; a fluorene group substituted or unsubstituted with one or more of the following groups: deuterium atom, fluorine atom, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, isopropyl, Spirodifluorenyl groups substituted or unsubstituted with one or more of the following groups: deuterated isopropyl, tert-butyl, deuterated tert-butyl, phenyl, deuterated phenyl, pentafluorophenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl; spiro-cyclopentyl-fluorenyl groups substituted or unsubstituted with one or more of the following groups: deuterium atom, fluorine atom, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, phenyl, deuterated phenyl, pentafluorophenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl; spiro-cyclopentyl-fluorenyl groups substituted or unsubstituted with one or more of the following groups: deuterium atom, fluorine atom, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, phenyl, deuterated phenyl, and pentafluorophenyl. Spiro-cyclohexyl-fluorene group substituted or unsubstituted with one or more of the following groups: phenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl; spiro-adamantyl-fluorene group substituted or unsubstituted with one or more of the following groups: deuterium atom, fluorine atom, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, phenyl, deuterated phenyl, pentafluorophenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl; spiro-adamantyl-fluorene group substituted or unsubstituted with one or more of the following groups: deuterium atom, fluorine atom, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, phenyl, deuterated phenyl, pentafluorophenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl. Spiro-cyclopentenyl-fluorenyl group substituted or unsubstituted with one or more of the following groups: deuterium atom, fluorine atom, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, phenyl, deuterated phenyl, pentafluorophenyl, naphthyl, deuterated naphthyl, biphenyl, deuterated biphenyl; carbazolyl group substituted or unsubstituted with one or more of the following groups: deuterium atom, fluorine atom, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, phenyl, deuterated phenyl, pentafluorophenyl, naphthyl, deuterated naphthyl, biphenyl, deuterated biphenyl;A furanyl group substituted or unsubstituted by one or more of the group consisting of deuterium, fluorine, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, phenyl, deuterated phenyl, pentafluorophenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl; The thiophene group substituted or unsubstituted with one or more of the following groups: methyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, phenyl, deuterated phenyl, pentafluorophenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl; substituted with one or more of the following groups: deuterium, fluorine, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, phenyl, deuterium Benzofuranyl group substituted or unsubstituted with one or more of the group consisting of phenyl, pentafluorophenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl; benzothiophene group substituted or unsubstituted with one or more of the group consisting of deuterium, fluorine, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, phenyl, deuterated phenyl, pentafluorophenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl; dibenzofuran group substituted or unsubstituted with one or more of the group consisting of deuterium, fluorine, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, phenyl, deuterated phenyl, pentafluorophenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl. The following are substituted or unsubstituted dibenzothiophene groups: dibenzothiophene group substituted or unsubstituted by one or more of the group consisting of deuterium, fluorine, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, phenyl, deuterated phenyl, pentafluorophenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl; pyridyl group substituted or unsubstituted by one or more of the group consisting of deuterium, fluorine, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, phenyl, deuterated phenyl, pentafluorophenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl; pyridyl group substituted or unsubstituted by one or more of the group consisting of deuterium, fluorine, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, and deuterated tert-butyl. A pyrimidinyl group substituted or unsubstituted with one or more of the group consisting of phenyl, deuterated phenyl, pentafluorophenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl; a triazine group substituted or unsubstituted with one or more of the group consisting of deuterium, fluorine, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, phenyl, deuterated phenyl, pentafluorophenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl; a pyrazinyl group substituted or unsubstituted with one or more of the group consisting of deuterium, fluorine, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, phenyl, deuterated phenyl, pentafluorophenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl;A pyridazinyl group substituted or unsubstituted by one or more of the group consisting of deuterium, fluorine, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, phenyl, deuterated phenyl, pentafluorophenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl; Quinolinyl groups substituted or unsubstituted with one or more of the groups consisting of phenyl and deuterated biphenyl; isoquinolinyl groups substituted or unsubstituted with one or more of the groups consisting of deuterium, fluorine, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, phenyl, deuterated phenyl, pentafluorophenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl; and isoquinolinyl groups substituted or unsubstituted with one or more of the groups consisting of deuterium, fluorine, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, isopropyl, deuterated isopropyl, and tert-butyl. The following are quinoxalinyl groups substituted or unsubstituted with one or more of the following groups: deuterated tert-butyl, phenyl, deuterated phenyl, pentafluorophenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl; quinoxalinyl groups substituted or unsubstituted with one or more of the following groups: deuterium atom, fluorine atom, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, phenyl, deuterated phenyl, pentafluorophenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl; quinoxalinyl groups substituted or unsubstituted with one or more of the following groups: deuterium atom, fluorine atom, cyano The methyl, trifluoromethyl, deuterated methyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, phenyl, deuterated phenyl, pentafluorophenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl groups are substituted or unsubstituted silyl groups, wherein the substituents are one or more, and when there are multiple substituents, the multiple substituents may be the same or different. When multiple substituents are present, adjacent substituents may optionally be linked to form a saturated or unsaturated C3-C10 carbon ring.

[0059] Preferably, each time R1 appears, it is selected from the same or different groups of substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted n-propyl, substituted or unsubstituted isopropyl, substituted or unsubstituted n-butyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopropane, substituted or unsubstituted cyclobutane, substituted or unsubstituted cyclopentane, substituted or unsubstituted cyclohexane, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracene, substituted or unsubstituted One of the following: phenanthrene, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted carbazolyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazine, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinoxalinyl, or substituted or unsubstituted quinazolinyl.

[0060] Preferably, each time R1 appears, it is selected from one of methyl, deuterated methyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, biphenyl, deuterated biphenyl, terphenyl, deuterated terphenyl, naphthylphenyl, deuterated naphthylphenyl, phenylnaphthyl, deuterated phenylnaphthyl, methyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, and adamantyl-substituted phenyl.

[0061] Preferably, in formulas (A-1) to (A-2), at most three of Y1 to Y6 are selected from nitrogen atoms, and one of them is connected to L and is selected from carbon atoms; in formulas (A-3) to (A-8), at most three of Y1 to Y8 are selected from nitrogen atoms, and one of Y1, Y2, Y5 to Y8 is connected to L and is selected from carbon atoms; in formulas (A-9) to (A-10), the three of Y1 to Y6 are selected from nitrogen atoms, and one of Y1, Y2, Y5 to Y8 is connected to L and is selected from carbon atoms; 10 At most three of them are selected from nitrogen atoms, and one of them is connected to L and is selected from carbon atoms.

[0062] Preferably, in formulas (A-1) to (A-2), at most two of Y1 to Y6 are selected from nitrogen atoms, and one of them is connected to L and is selected from carbon atoms; in formulas (A-3) to (A-8), at most two of Y1 to Y8 are selected from nitrogen atoms, and one of Y1, Y2, Y5 to Y8 is connected to L and is selected from carbon atoms; in formulas (A-9) to (A-10), the Y1 to Y6... 10At most two of them are selected from nitrogen atoms, and one of them is connected to L and is selected from carbon atoms.

[0063] Preferably, in formulas (A-1) to (A-2), at most one of Y1 to Y6 is selected from nitrogen atoms, and one of them is connected to L and is selected from carbon atoms; in formulas (A-3) to (A-8), at most one of Y1 to Y8 is selected from nitrogen atoms, and one of Y1, Y2, Y5 to Y8 is connected to L and is selected from carbon atoms; in formulas (A-9) to (A-10), the Y1 to Y6... 10 At most one of them is selected from nitrogen atoms, and one of them is connected to L and is selected from carbon atoms.

[0064] Preferably, A is selected from one of the following structures:

[0065]

[0066]

[0067] Wherein, the a 11 Each time it appears, it is selected from 0, 1, 2, 3, or 4, either identically or differently; the b mentioned 11 Each time it appears, it is selected from 0, 1, or 2, either identically or differently; the c mentioned 11 Each time it appears, it is selected from 0 or 1, either identically or differently; the d mentioned 11 Each time it appears, it is selected from 0, 1, 2 or 3, either the same or different;

[0068] The R mentioned 11 Each time it appears, it is selected from one of the following groups, either identically or differently: hydrogen atom, deuterium atom, fluorine atom, cyano group, methyl group, deuterated methyl group, trifluoromethyl group, ethyl group, deuterated ethyl group, n-propyl group, isopropyl group, deuterated isopropyl group, n-butyl group, tert-butyl group, deuterated tert-butyl group, cyclopentyl group, deuterated cyclopentyl group, cyclohexyl group, deuterated cyclohexyl group, phenyl group, deuterated phenyl group, pyridyl group, deuterated pyridyl group, pyrimidinyl group, deuterated pyrimidinyl group, triazinyl group, deuterated triazinyl group, pyrazinyl group, deuterated pyrazinyl group, pyridazinyl group, deuterated pyridazinyl group.

[0069] Preferably, the Ar1 is selected from hydrogen atom, deuterium atom, cyano group, halogen atom or one of the following structures:

[0070]

[0071] Wherein, the a 21 Each time it appears, it is selected from 0, 1, 2, 3, 4, or 5, either identically or differently; the b mentioned 21 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, or 7, either identically or differently; c 21Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9, either identically or differently; the d mentioned 21 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or different.

[0072] 11; the e mentioned above 21 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, or 15, either identically or differently; the f 21 Each time it appears, it is selected from 0, 1, 2, or 3, either identically or differently; the g mentioned 21 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8, either identically or differently; the h mentioned 21 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, either identically or differently; the i 21 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, either the same or different.

[0073] 13 or 14; the j mentioned 21 Each time it appears, it is selected from 0, 1, 2, 3, or 4, either identically or differently; the k mentioned 21 Each time it appears, it is selected from 0, 1, or 2, either identically or differently; the l mentioned 21 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, or 6, either the same or different.

[0074] The R mentioned 21 Each time it appears, it is selected from the same or different groups: hydrogen atom, deuterium atom, fluorine atom, cyano, methyl, deuterated methyl, trifluoromethyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, cyclopentyl, deuterated cyclopentyl, cyclohexyl, deuterated cyclohexyl, adamantyl, norbornel, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, anthracene, deuterated anthracene, phenanthrene, deuterated phenanthrene, triphenylene, deuterated triphenylene, biphenyl, deuterated biphenyl, indene, deuterated One of the following: indanthyl, tetrahydronaphthyl, deuterated tetrahydronaphthyl, furanyl, thiopheneyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, pyridyl, deuterated pyridyl, pyrimidinyl, deuterated pyrimidinyl, triazinyl, deuterated triazinyl, pyrazinyl, deuterated pyrazinyl, pyridazinyl, deuterated pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, isoquinazolinyl, benzoquinolinyl, and o-phenanthrolinel.

[0075] Preferably, the Ar1 is selected from hydrogen atom, deuterium atom, cyano group, fluorine atom, or one of the following structures:

[0076]

[0077]

[0078] Wherein, the a 31 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9, either identically or differently; the b mentioned 31 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11, either identically or differently; c 31 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, or 15, either identically or differently; the d mentioned 31 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, or 7, either identically or differently; the e mentioned 31 Each time it appears, it is selected from 0, 1, 2, 3, 4, or 5, either identically or differently; the f mentioned 31 Each time it appears, it is selected from 0, 1, 2, 3, or 4, either identically or differently; the g mentioned 31 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, or 6, either identically or differently; the h mentioned 31 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8, either identically or differently; the i 31 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, either identically or differently; j 31 Each time it appears, it is selected from 0, 1, 2, or 3, either identically or differently; the k mentioned 31 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14, either the same or different.

[0079] Preferably, the Ar2 is selected from hydrogen atom, deuterium atom, methyl, deuterated methyl, ethyl, deuterated ethyl, n-propyl, isopropyl, deuterated isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, deuterated tert-butyl, cyano, halogen atom, or one of the following structures:

[0080]

[0081] Wherein, the a 21 b 21 c 21 d 21 e 21 f 21 g 21 h 21 i 21 j 21 k 21 l21 R 21 All are as described in this invention.

[0082] Preferably, the Ar2 is selected from hydrogen atom, deuterium atom, methyl, deuterated methyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, cyano, fluorine atom, or one of the following structures:

[0083]

[0084]

[0085] Wherein, the a 31 b 31 c 31 d 31 e 31 f 31 g 31 h 31 i 31 j 31 k 31 All are as described in this invention.

[0086] Preferably, the L is selected from one of the following structures:

[0087]

[0088] Wherein, the a 41 Each time it appears, it is selected from 0, 1, 2, 3, or 4, either identically or differently; the b mentioned 41 Each time it appears, it is selected from 0, 1, 2, or 3, either identically or differently; the c mentioned 41 Each time it appears, it is selected from 0, 1, or 2, either identically or differently; the d mentioned 41 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, or 6, either identically or differently; the e 41 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8, either identically or differently; the f mentioned 41 Each time it appears, it is selected from 0, 1, 2, 3, 4, or 5, either identically or differently; the g mentioned 41 Each time it appears, it is selected from 0 or 1, either the same or different.

[0089] The R mentioned 41Each time it appears, it is selected from the same or different groups of hydrogen atom, deuterium atom, cyano group, fluorine atom, methyl group, deuterated methyl group, trifluoromethyl group, ethyl group, isopropyl group, deuterated isopropyl group, tert-butyl group, deuterated tert-butyl group, cyclopentyl group, deuterated cyclopentyl group, cyclohexyl group, deuterated cyclohexyl group, adamantyl group, norbornel group, phenyl group, deuterated phenyl group, naphthyl group, deuterated naphthyl group, biphenyl group, deuterated biphenyl group, pyridyl group, deuterated pyridyl group, triazinyl group, deuterated triazinyl group, pyrazinyl group, deuterated pyrazinyl group, pyridazinyl group, deuterated pyridazinyl group, quinolinyl group, deuterated quinolinyl group, isoquinolinyl group, deuterated isoquinolinyl group, quinoxalyl group, deuterated quinoxalyl group, quinazolinyl group, deuterated quinazolinyl group.

[0090] Preferably, the L is selected from one of the following structures:

[0091]

[0092]

[0093] Wherein, the a 51 Each time it appears, it is selected from 1, 2, 3, or 4, either identically or differently; the b mentioned above 51 Each time it appears, it is selected from 1, 2, or 3, either identically or differently; the c mentioned above 51 Each time it appears, it is selected from 1 or 2, either identically or differently; the d mentioned 51 Each time it appears, it is selected from 1, 2, 3, 4, 5, or 6, either identically or differently; the e mentioned 51 Each time it appears, it is selected from 1, 2, 3, 4, or 5, either identically or differently; the f mentioned 51 Each time it appears, it is selected from 1, 2, 3, 4, 5, 6, 7, or 8, either identically or differently; the g mentioned 51 Each time it appears, it is selected from 1, 2, 3, 4, 5, 6 or 7, either the same or different.

[0094] The R mentioned 51 It is selected from one of the following: hydrogen atom, deuterium atom, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl.

[0095] Preferably, B is selected from one of the following structures:

[0096]

[0097]

[0098] in, In formulas (IA) and (IB), it represents none; in formula (IC), it represents a connection bond with L; the a 11 b 11 c 11 d11 R 11 All are as described in this invention.

[0099] Preferably, the heterocyclic compound is selected from one of the following structures:

[0100]

[0101] Wherein, A, B, Ar1, Ar2, R1, R3, and L are as described in this invention. Preferably, the heterocyclic compound is selected from one of the following structures:

[0102]

[0103] Wherein, A, B, Ar1, Ar2, R1, and L are as described in this invention.

[0104] Preferably, the heterocyclic compound is selected from one of the following structures:

[0105]

[0106] Wherein, A, B, Ar1, Ar2, R1, R3, and L are as described in this invention. Most preferably, the heterocyclic compound is selected from one of the following compounds:

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129] The above only lists some specific structural forms of heterocyclic compounds represented by formulas (IA) to (IC), but the present invention is not limited to these chemical structures. Any chemical structure based on formulas (IA) to (IC) with substituents as defined in the present invention should be included.

[0130] The heterocyclic compounds represented by formulas (IA) to (IC) of this invention can be prepared by one of the following synthetic routes:

[0131]

[0132]

[0133] Wherein, x is selected from The y is selected from chlorine atoms, bromine atoms, or iodine atoms;

[0134] A, B, X1, X2, X3, Ar1, Ar2, and L are all as described in this invention.

[0135] In the above synthetic routes, compounds Y (i.e., compounds YA to YL) and Z (i.e., compounds ZA to ZD) can be coupled via a Suzuki reaction to obtain the target compounds (IA) to (IC).

[0136] All the above reaction routes employ commonly used reaction types in organic synthesis, and there are no particular restrictions on reaction conditions (e.g., the selection, amount, order, and method of addition of reaction solvents, catalysts, ligands, bases, etc.). The above preparation methods utilize readily available raw materials, have simple processes, and yield excellent results. The compounds represented by formulas (IA) to (IC) provided by this invention can also be synthesized using other conventional reaction types in organic synthesis without particular limitations; the above are merely examples of synthetic routes.

[0137] The present invention also provides an organic electroluminescent device, comprising an anode, a cathode, and an organic layer, wherein the organic layer comprises at least one of a hole transport region between the anode and the cathode, a light-emitting layer, an electron transport region, and a capping layer on the side of the cathode opposite to the anode, and the organic layer contains one or more of the heterocyclic compounds described in the present invention.

[0138] Preferably, the organic layer includes a hole transport region, a light-emitting layer, and an electron transport region between the anode and the cathode, wherein at least one of the light-emitting layer and the electron transport region contains one or more of the heterocyclic compounds described in this invention; more preferably, the light-emitting layer contains one or more of the heterocyclic compounds described in this invention.

[0139] Preferably, the organic layer includes a hole transport region between the anode and the cathode, a light-emitting layer, an electron transport region, and a capping layer on the side of the cathode facing away from the anode, wherein at least one of the light-emitting layer, the electron transport region, and the capping layer contains one or more of the heterocyclic compounds described in this invention; more preferably, the light-emitting layer or the electron transport region contains one or more of the heterocyclic compounds described in this invention; even more preferably, the light-emitting layer contains one or more of the heterocyclic compounds described in this invention.

[0140] The hole transport region of the present invention includes at least one of a hole injection layer, a hole transport layer, and a light emission assist layer.

[0141] Preferably, the hole transport region includes at least two of the following: a hole injection layer, a hole transport layer, and a light-emitting auxiliary layer; more preferably, the hole transport region includes a hole injection layer and a hole transport layer.

[0142] Preferably, the hole transport region includes a hole injection layer, a hole transport layer, and a light-emitting auxiliary layer.

[0143] The hole injection layer described in this invention can be a monolayer structure composed of a single substance, or a monolayer or multilayer structure composed of different substances. Triarylamine compounds, porphyrin compounds, styrene compounds, polythiophene and its derivatives, phthalocyanine derivatives, axialene compounds, and other substances with high hole injection properties can be used, such as 4,4',4”-tris[2-naphthylphenylamino]triphenylamine (2-TNATA), 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazabenzenephenanthrene (HATCN), copper phthalocyanine (CuPC), 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanodimethyl-p-benzoquinone (F4-TCNQ), poly(3,4-ethylenedioxythiophene)-poly(styrenesulfonic acid) (PEDOT / PSS), compounds HT-1 to HT-19, and compounds p-1 to p-3, but not limited to these.

[0144]

[0145] The hole transport layer described in this invention can be a monolayer structure composed of a single material, or a monolayer or multilayer structure composed of different materials. Triarylamine compounds can be used, or other compounds with a hole mobility of 10... -6 cm 2 Substances with a concentration of / Vs or higher, such as N,N'-diphenyl-N,N'-di(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), 4,4'4"-tris(N,N-diphenylamino)triphenylamine (TDATA), and compounds HT-1 to HT-19 as shown above, but not limited thereto.

[0146] The light-emitting auxiliary layer described in this invention can be a single-layer structure composed of a single material, or a single-layer or multi-layer structure composed of different materials. Triarylamine compounds, spirofluorene derivatives, dibenzofuran derivatives, or other substances with suitable HOMO and T1 energy levels can be used. Examples include TPD, NPB, N4,N4-bis([1,1'-biphenyl]-4-yl)-N4'-phenylN4'-[1,1':4',1”-terphenyl]-4-yl-[1,1'-biphenyl]-4,4'-diamine, N-([1,1'-diphenyl]-4-yl)-N-(9,9-dimethyl-9H-furan-2-yl)-9,9'-spirodifluorene-2-amine, N,N-bis([1,1'-biphenyl]-4-yl)-3'-(dibenzo[b,d]furan-4-yl)-[1,1'-biphenyl]-4-amine, and compounds HT-1 to HT-19 as shown above, but are not limited to these.

[0147] The luminescent layer of the present invention comprises a guest material and a host material, and a dual host material formed by two host materials can be used. The guest material can be a fluorescent compound, such as pyrene derivatives, fluoranthene derivatives, aromatic amine derivatives, etc. Examples include 10-(2-benzothiazolyl)-2,3,6,7-tetrahydro-1,1,7,7-tetramethyl-1H,5H,11H-[1]benzopyran[6,7,8-ij]quinolinazine-11-one (C545T), 4,4'-bis(9-ethyl-3-carbazolevinyl)-1,1'-biphenyl (BCzVBi), 4, 4'-Bis[4-(di-p-tolylamino)styryl]biphenyl (DPAVBi) and other materials can also be used, such as phosphorescent materials, metal complexes such as iridium complexes, osmium complexes, and platinum complexes. Examples include bis(4,6-difluorophenylpyridine-N,C2)pyridineformyliridium (FIrpic), tris(2-phenylpyridine)iridium (Ir(ppy)3), and bis(2-phenylpyridine)iridium acetylacetonate (Ir(ppy)2(acac)). The host material is preferably a substance with a higher LUMO and a lower HOMO than the guest material, such as metal complexes like aluminum or zinc complexes, heterocyclic compounds like oxadiazole derivatives, benzoxazole derivatives, benzothiazole derivatives, or benzimidazole derivatives, fused aromatic compounds like carbazole or anthracene derivatives, and aromatic amine compounds like triaromatic amine derivatives or fused polycyclic aromatic amine derivatives. Examples include Alq3, BAlq, TPBI, TPD, 4,4'-bis(9-carbazole)biphenyl (CBP), 4,4',4”-tris(carbazole-9-yl)triphenylamine (TCTA), 9,10-bis(2-naphthyl)anthracene (ADN), and heterocyclic compounds described in this invention, but not limited thereto. Preferably, the host material contains one or more of the heterocyclic compounds described in this invention.

[0148] Preferably, the host material contains at least two different compounds, and at least one is selected from the heterocyclic compounds described in this invention. More preferably, the host material contains two different compounds, with the heterocyclic compound described in this invention serving as the n-type host and the other compound serving as the p-type host. The p-type host can be a fused aromatic compound such as a carbazole derivative or anthracene derivative, an aromatic amine compound such as a triarylamine derivative or a fused polycyclic aromatic amine derivative, etc., preferably a carbazole derivative, specifically listed as compounds H-1 to H-17 as shown below, but not limited thereto. Even more preferably, the mass ratio of the heterocyclic compound (n-type host) to the p-type host used in combination is between 1:10 and 10:1. Most preferably, the mass ratio of the heterocyclic compound (n-type host) to the p-type host used in combination is between 1:5 and 5:1.

[0149]

[0150]

[0151] The electron transport region of the present invention includes at least one of an electron injection layer, an electron transport layer, and a hole blocking layer.

[0152] Preferably, the electron transport region includes at least two of the following: an electron injection layer, an electron transport layer, and a hole blocking layer; more preferably, the electron transport region includes an electron injection layer and an electron transport layer.

[0153] Preferably, the electron transport region includes an electron injection layer, an electron transport layer, and a hole blocking layer.

[0154] The electron injection layer described in this invention can be a monolayer structure composed of a single substance, or a monolayer or multilayer structure composed of different substances. It can be one or more of the following substances: alkali metals, alkaline earth metals, alkali metal halides, alkaline earth metal halides, alkali metal oxides, alkaline earth metal oxides, alkali metal salts, alkaline earth metal salts, and other substances with high electron injection properties. Examples include Li, Ca, Sr, LiF, CsF, CaF2, BaO, Li2CO3, CaCO3, Li2C2O4, Cs2C2O4, CsAlF4, LiOx, Yb, Tb, etc., but are not limited to these.

[0155] The electron transport layer described in this invention can be a single-layer structure composed of a single substance, or a single-layer or multi-layer structure composed of different substances. It can use aluminum complexes, lithium complexes, beryllium complexes, zinc complexes, oxazole derivatives, benzoxazole derivatives, thiazole derivatives, benzothiazole derivatives, imidazole derivatives, benzimidazole derivatives, carbazole derivatives, phenanthroline derivatives, polymeric compounds, etc. Examples include 8-hydroxyquinoline aluminum (Alq3), bis(10-hydroxybenzo[h]quinoline) beryllium (BeBq2), bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), 2-(4-biphenyl)-5-phenyloxadiazole (PBD), heterocyclic compounds described in this invention, etc., but are not limited thereto.

[0156] The hole-blocking layer described in this invention can be a single-layer structure composed of a single material, or a single-layer or multi-layer structure composed of different materials. The selected material must have a T1 energy level higher than that of the emissive layer to prevent energy loss from the emissive layer. Furthermore, the HOMO energy level of the selected material must be lower than that of the main material of the emissive layer to effectively block holes. Further, the electron mobility of the hole-blocking layer material used is 10.-6 cm 2 A value of / Vs or higher facilitates electron transport. One or more of the following substances can be selected: aluminum complexes, lithium complexes, beryllium complexes, oxazole derivatives, benzoxazole derivatives, thiazole derivatives, benzothiazole derivatives, imidazole derivatives, benzimidazole derivatives, phenanthroline derivatives, polymers, etc. Examples include 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene (TPBI), BAlq, and the heterocyclic compounds described in this invention, but are not limited thereto. Preferably, the hole-blocking layer contains the heterocyclic compounds described in this invention.

[0157] The anode described in this invention can be a reflective anode, such as a reflective film formed of silver (Ag), magnesium (Mg), aluminum (Al), gold (Au), nickel (Ni), chromium (Cr), ytterbium (Yb), or their alloys. It can also be a layered structure with a high work function that is transparent or semi-transparent, such as a layered structure formed of indium tin oxide (ITO), indium zinc oxide (ZnO), zinc oxide (ZnO), aluminum zinc oxide (AZO), indium gallium oxide (IGO), indium oxide (In2O3), or tin oxide (SnO2). The specific anode depends on the type of device to be fabricated. For example, if the device to be fabricated is a bottom-emitting device (emitting light from the anode side), a transparent or semi-transparent anode needs to be fabricated. If the device to be fabricated is a top-emitting device (emitting light from the cathode side), a reflective anode needs to be fabricated.

[0158] The cathode described in this invention can be a thin film with a low work function made of lithium, calcium, lithium fluoride / calcium, lithium fluoride / aluminum, aluminum, silver, magnesium, magnesium-silver alloy, etc. The thickness of the film can be adjusted to make a reflective electrode, a transparent electrode, or a semi-transparent electrode. If a bottom-emitting device is to be made, a reflective cathode needs to be made. If a top-emitting device is to be made, a transparent or semi-transparent cathode needs to be made.

[0159] The capping layer described in this invention can be a single-layer structure composed of a single substance, or a single-layer or multi-layer structure composed of different substances. The capping layer material can be an organic or inorganic substance with an appropriate refractive index, such as metal halides, oxides, nitrides, nitrogen oxides, sulfides, selenides, aromatic compounds, heteroaromatic compounds, aromatic amine compounds, etc. Examples include LiF, CsF, MgF2, CaF2, CsCl, CuI, V2O5, WO3, MoO3, TiO2, ZrO, ZnO, SiO2, SiN, ZnS, Alq3, compound CP-1, compound CP-2, compound CP-3, compound CP-4, and the heterocyclic compounds described in this invention, but are not limited thereto.

[0160]

[0161] The aforementioned organic layers, cathode, anode, and capping layer can be prepared using any of the following methods: vacuum evaporation, inkjet printing, sputtering, plasma deposition, ion plating, spin coating, impregnation, or screen printing. There are no particular limitations on the thickness of each layer, as long as good device performance is achieved. Preferably, the aforementioned organic layers are prepared using vacuum evaporation, inkjet printing, or spin coating.

[0162] The thickness of each of the aforementioned organic layers and capping layers is typically between 5 nm and 100 μm, preferably between 10 nm and 200 nm. The thickness of the anode and cathode is adjusted according to the required transparency.

[0163] The organic electroluminescent device provided by this invention can be applied to lighting and display fields, specifically including smartphone displays, tablet displays, smart wearable device displays, large-size displays such as televisions, VR, and car taillights.

[0164] The technical solutions and effects of the present invention will be further described below with reference to embodiments and comparative examples.

[0165] The mass spectrometry of the compounds of this invention was performed using a G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer from Waters Instruments Ltd., UK, with chloroform as the solvent.

[0166] 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.

[0167] Synthesis Example 1: Synthesis of Compound 6

[0168]

[0169] Preparation of intermediate bb-6:

[0170] Under nitrogen protection, aa-6 (23.76 g, 120.00 mmol), pinacol diboronate (33.52 g, 132.00 mmol), CH3COOK (15.31 g, 156.00 mmol), Pd(dppf)Cl2 (0.44 g, 0.60 mmol), and 900 mL of THF were added to the reaction flask, and the mixture was reacted under reflux for 7 hours. After the reaction was completed, the mixture was cooled to room temperature, water was added, and the mixture was filtered to obtain a filter cake, which was then dried in a vacuum oven. The crude product was purified by silica gel column chromatography (n-hexane:ethyl acetate = 1:1) to obtain intermediate bb-6 (24.12 g, yield 82%); HPLC purity ≥99.78%. Mass spectrometry m / z: 245.1235 (theoretical value: 245.1223).

[0171] Preparation of intermediate dd-6:

[0172] Under nitrogen protection, bb-6 (19.61 g, 80.00 mmol), cc-6 (28.72 g, 80.00 mmol), Na₂CO₃ (12.72 g, 120.00 mmol), Pd(PPh₃)₄ (0.92 g, 0.80 mmol), and 320 mL of 1,4-dioxane were added to a reaction flask, and the mixture was reacted under reflux for 8.5 hours. 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 MgSO₄, the solvent was removed under reduced pressure, and the mixture was recrystallized from toluene / petroleum ether at a ratio of 4:1 to give intermediate dd-6 (21.29 g, yield 76%); HPLC purity ≥99.70%. Mass spectrometry m / z: 349.0120 (theoretical value: 349.0102).

[0173] Preparation of intermediate ee-6:

[0174] Under nitrogen protection, dd-6 (17.51 ​​g, 50.00 mmol), pinacol diborate (13.97 g, 55.00 mmol), K₂CO₃ (8.98 g, 65.00 mmol), Pd(dppf)Cl₂ (0.18 g, 0.25 mmol), and 435 mL THF were added to a reaction flask, and the mixture was reacted under reflux for 6.5 hours. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was filtered to obtain a filter cake. The cake was recrystallized from toluene / n-hexane at a ratio of 5:1 to give intermediate ee-6 (15.49 g, yield 78%); HPLC purity ≥99.80%. Mass spectrometry m / z: 397.1840 (theoretical value: 397.1849).

[0175] Preparation of compound 6:

[0176] Under nitrogen protection, ee-6 (11.92 g, 30.00 mmol), ff-6 (9.89 g, 30.00 mmol), Na₂CO₃ (4.77 g, 45.00 mmol), Pd(OAc)₂ (0.07 g, 0.30 mmol), P(t-Bu)₃ (0.06 g, 0.30 mmol), and 120 mL of THF were added to a reaction flask, and the mixture was reacted under reflux for 8 hours. After the reaction was completed, the mixture was cooled to room temperature, water was added, and the mixture was extracted with chloroform. The organic layer was dried over anhydrous MgSO₄, the solvent was removed under reduced pressure, and the mixture was recrystallized from toluene to give compound 6 (12.54 g, yield 74%); HPLC purity ≥99.92%. Mass spectrometry m / z: 564.1827 (theoretical value: 564.1838). Theoretical elemental content (%) C 40 H 24N2O2: C, 85.09; H, 4.28; N, 4.96. Measured elemental content (%): C, 85.06; H, 4.24; N, 4.99.

[0177] Synthesis Example 2: Synthesis of Compound 51

[0178]

[0179] Following the same preparation method as in Synthesis Example 1, dd-6 and ff-6 were replaced with equimolar amounts of dd-51 and ff-51, respectively, to obtain compound 51 (11.51 g, yield 76%). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 504.1283 (theoretical value: 504.1296). Theoretical elemental content (%) C 34 H 20 N₂OS: C, 80.93; H, 4.00; N, 5.55. Analyzed elemental composition (%): C, 80.97; H, 4.03; N, 5.52. Synthesis Example 3: Synthesis of Compound 57

[0180]

[0181] Following the same preparation method as in Synthesis Example 1, cc-6 and ff-6 were replaced with equimolar amounts of cc-57 and ff-57, respectively, to obtain compound 57 (12.56 g, yield 72%). HPLC analysis showed a solid purity ≥99.90%. Mass spectrometry m / z: 581.1573 (theoretical value: 581.1562). Theoretical elemental content (%) C 39 H 23 N3OS: C, 80.53; H, 3.99; N, 7.22. Measured elemental composition (%): C, 80.50; H, 3.95; N, 7.26. Synthesis Example 4: Synthesis of Compound 118

[0182]

[0183] Following the same preparation method as in Synthesis Example 1, dd-6 and ff-6 were replaced with equimolar amounts of dd-118 and ff-118, respectively, to obtain compound 118 (12.89 g, yield 74%). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 580.1621 (theoretical value: 580.1609). Theoretical elemental content (%) C 40 H 24 N₂OS: C, 82.73; H, 4.17; N, 4.82. Measured elemental content (%): C, 82.76; H, 4.12; N, 4.86.

[0184] Synthesis Example 5: Synthesis of Compound 142

[0185]

[0186] Following the same preparation method as in Synthesis Example 1, aa-6, cc-6, and ff-6 were replaced with equimolar amounts of aa-142, cc-142, and ff-142 to obtain compound 142 (11.60 g, yield 73%). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 529.1642 (theoretical value: 529.1633). Theoretical elemental content (%) C 34 H 11 D9N2S2: C, 77.09; H, 5.52; N, 5.29. Measured elemental content (%): C, 77.13; H, 5.49; N, 5.33.

[0187] Synthesis Example 6: Synthesis of Compound 290

[0188]

[0189] Following the same preparation method as in Synthesis Example 1, aa-6, cc-6, and ff-6 were replaced with equimolar amounts of aa-290, aa-6, and ff-290, respectively, to obtain compound 290 (11.14 g, yield 72%). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 515.1622 (theoretical value: 515.1634). Theoretical elemental content (%) C 35 H 21 N3O2: C, 81.54; H, 4.11; N, 8.15. Measured elemental content (%): C, 81.51; H, 4.16; N, 8.18.

[0190] Synthesis Example 7: Synthesis of Compound 292

[0191]

[0192] Following the same preparation method as in Synthesis Example 1, aa-6, cc-6, and ff-6 were replaced with equimolar amounts of aa-290, aa-6, and ff-292, respectively, to obtain compound 292 (12.70 g, yield 75%). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 564.1825 (theoretical value: 564.1838). Theoretical elemental content (%) C 40 H 24 N2O2: C, 85.09; H, 4.28; N, 4.96. Measured elemental content (%): C, 85.12; H, 4.23; N, 4.93.

[0193] Synthesis Example 8: Synthesis of Compound 293

[0194]

[0195] Following the same preparation method as in Synthesis Example 1, aa-6, cc-6, and ff-6 were replaced with equimolar amounts of aa-293, cc-142, and ff-6, respectively, to obtain compound 293 (12.37 g, yield 71%). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 580.1623 (theoretical value: 580.1609). Theoretical elemental content (%) C 40 H 24 N₂OS: C, 82.73; H, 4.17; N, 4.82. Measured elemental content (%): C, 82.70; H, 4.13; N, 4.86.

[0196] Synthesis Example 9: Synthesis of Compound 316

[0197]

[0198] Following the same preparation method as in Synthesis Example 1, aa-6, cc-6, and ff-6 were replaced with equimolar amounts of dd-118, cc-316, and ff-316, respectively, to obtain compound 316 (12.87 g, yield 68%). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 630.1526 (theoretical value: 630.1514). Theoretical elemental content (%) C 42 H 22 N4OS: C, 79.98; H, 3.52; N, 8.88. Measured elemental content (%): C, 79.93; H, 3.55; N, 8.84.

[0199] Synthesis Example 10: Synthesis of Compound 325

[0200]

[0201] Following the same preparation method as in Synthesis Example 1, aa-6, cc-6, and ff-6 were replaced with equimolar amounts of aa-290, cc-325, and ff-292, respectively, to obtain compound 325 (12.51 g, yield 74%). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 563.1876 (theoretical value: 563.1885). Theoretical elemental content (%) C 41 H 25 NO2: C, 87.37; H, 4.47; N, 2.49. Measured elemental content (%): C, 87.33; H, 4.44; N, 2.52.

[0202] Synthesis Example 11: Synthesis of Compound 339

[0203]

[0204] Following the same preparation method as in Synthesis Example 1, aa-6, cc-6, and ff-6 were replaced with equimolar amounts of aa-339, cc-339, and ff-339, respectively, to obtain compound 339 (13.12 g, yield 70%). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 624.1431 (theoretical value: 624.1442). Theoretical elemental content (%) C 40 H 24 N4S2: C, 76.90; H, 3.87; N, 8.97. Measured elemental content (%): C, 76.94; H, 3.84; N, 8.95.

[0205] Synthesis Example 12: Synthesis of Compound 353

[0206]

[0207] Following the same preparation method as in Synthesis Example 1, aa-6, cc-6, and ff-6 were replaced with equimolar amounts of aa-142, cc-353, and ff-353, respectively, to obtain compound 353 (15.08 g, yield 73%). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 668.2420 (theoretical value: 668.2402). Theoretical elemental content (%) C 48 H 24 D4N2O2: C, 86.20; H, 4.82; N, 4.19. Measured elemental content (%): C, 86.23; H, 4.86; N, 4.14.

[0208] Synthesis Example 13: Synthesis of Compound 356

[0209]

[0210] Following the same preparation method as in Synthesis Example 1, aa-6, cc-6, and ff-6 were replaced with equimolar amounts of aa-339, aa-6, and ff-356, respectively, to obtain compound 356 (12.75 g, yield 75%). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 564.1849 (theoretical value: 564.1838). Theoretical elemental content (%) C 40 H 24 N2O2: C, 85.09; H, 4.28; N, 4.96. Measured elemental content (%): C, 85.05; H, 4.31; N, 4.98.

[0211] Synthesis Example 14: Synthesis of Compound 366

[0212]

[0213] Following the same preparation method as in Synthesis Example 1, aa-6, cc-6, and ff-6 were replaced with equimolar amounts of aa-293, aa-6, and ff-366, respectively, to obtain compound 366 (17.15 g, yield 71%). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 804.2790 (theoretical value: 804.2777). Theoretical elemental content (%) C 59 H 36 N2O2: C, 88.04; H, 4.51; N, 3.48. Measured elemental content (%): C, 88.08; H, 4.54; N, 3.44.

[0214] Synthesis Example 15: Synthesis of Compound 379

[0215]

[0216] Following the same preparation method as in Synthesis Example 1, aa-6, cc-6, and ff-6 were replaced with equimolar amounts of aa-293, cc-379, and ff-379, respectively, to obtain compound 379 (14.51 g, yield 72%). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 671.1729 (theoretical value: 671.1741). Theoretical elemental content (%) C 47 H 29 NS2: C, 84.02; H, 4.35; N, 2.08. Measured elemental content (%): C, 84.06; H, 4.38; N, 2.03.

[0217] Synthesis Example 16: Synthesis of Compound 401

[0218]

[0219] Following the same preparation method as in Synthesis Example 1, aa-6, cc-6, and ff-6 were replaced with equimolar amounts of aa-401, aa-339, and ff-401, respectively, to obtain compound 401 (12.62 g, yield 74%). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 568.2073 (theoretical value: 568.2089). Theoretical elemental content (%) C 40 H 20 D4N2O2: C, 84.49; H, 4.96; N, 4.93. Measured elemental content (%): C, 84.52; H, 4.92; N, 4.97.

[0220] Synthesis Example 17: Synthesis of Compound 432

[0221]

[0222] Following the same preparation method as in Synthesis Example 1, aa-6, cc-6, and ff-6 were replaced with equimolar amounts of aa-432, aa-6, and ff-353, respectively, to obtain compound 432 (12.70 g, yield 75%). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 564.1850 (theoretical value: 564.1838). Theoretical elemental content (%) C 40 H 24 N2O2: C, 85.09; H, 4.28; N, 4.96. Measured elemental content (%): C, 85.04; H, 4.25; N, 4.92.

[0223] Synthesis Example 18: Synthesis of Compound 441

[0224]

[0225] Following the same preparation method as in Synthesis Example 1, aa-6, cc-6, and ff-6 were replaced with equimolar amounts of aa-142, cc-441, and ff-441, respectively, to obtain compound 441 (13.90 g, yield 73%). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 634.2032 (theoretical value: 634.2017). Theoretical elemental content (%) C 44 H 22 D4N2OS: C, 83.25; H, 4.76; N, 4.41. Measured elemental content (%): C, 83.21; H, 4.73; N, 4.45.

[0226] Synthesis Example 19: Synthesis of Compound 449

[0227]

[0228] Following the same preparation method as in Synthesis Example 1, aa-6, cc-6, and ff-6 were replaced with equimolar amounts of aa-449, aa-6, and ff-449, respectively, to obtain compound 449 (13.42 g, yield 68%). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 657.2203 (theoretical value: 657.2216). Theoretical elemental content (%) C 46 H 28 FN3O: C, 84.00; H, 4.29; N, 6.39. Measured elemental content (%): C, 84.03; H, 4.26; N, 6.34.

[0229] Synthesis Example 20: Synthesis of Compound 476

[0230]

[0231] Following the same preparation method as in Synthesis Example 1, aa-6, cc-6, and ff-6 were replaced with equimolar amounts of aa-339, cc-476, and ff-57, respectively, to obtain compound 476 (14.38 g, yield 73%). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 656.1906 (theoretical value: 656.1922). Theoretical elemental content (%) C 46 H 28 N₂OS: C, 84.12; H, 4.30; N, 4.27. Measured elemental content (%): C, 84.08; H, 4.27; N, 4.31.

[0232] Synthesis Example 21: Synthesis of Compound 488

[0233]

[0234] Following the same preparation method as in Synthesis Example 1, aa-6, cc-6, and ff-6 were replaced with equimolar amounts of aa-488, cc-488, and ff-488, respectively, to obtain compound 488 (14.51 g, yield 70%). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 690.2572 (theoretical value: 690.2581). Theoretical elemental content (%) C 48 H 22 D8N2OS: C, 83.45; H, 5.54; N, 4.05. Measured elemental content (%): C, 83.48; H, 5.58; N, 4.01.

[0235] Synthesis Example 22: Synthesis of Compound 506

[0236]

[0237] Following the same preparation method as in Synthesis Example 1, aa-6, cc-6, and ff-6 were replaced with equimolar amounts of aa-506, cc-506, and ff-449, respectively, to obtain compound 506 (14.41 g, yield 67%). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 716.2590 (theoretical value: 716.2576). Theoretical elemental content (%) C 51 H 32 N4O: C, 85.45; H, 4.50; N, 7.82. Measured elemental content (%): C, 85.49; H, 4.53; N, 7.85.

[0238] Synthesis Example 23: Synthesis of Compound 518

[0239]

[0240] Following the same preparation method as in Synthesis Example 1, aa-6, cc-6, and ff-6 were replaced with equimolar amounts of aa-401, cc-518, and ff-292, respectively, to obtain compound 518 (13.93 g, yield 72%). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 644.2416 (theoretical value: 644.2402). Theoretical elemental content (%) C 46 H 24 D4N2O2: C, 85.69; H, 5.00; N, 4.34. Measured elemental content (%): C, 85.64; H, 5.03; N, 4.38.

[0241] Synthesis Example 24: Synthesis of Compound 605

[0242]

[0243] Following the same preparation method as in Synthesis Example 1, aa-6, cc-6, and ff-6 were replaced with equimolar amounts of aa-605, cc-605, and ff-6, respectively, to obtain compound 605 (14.01 g, yield 73%). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 639.1932 (theoretical value: 639.1947). Theoretical elemental content (%) C 45 H 25 N3O2: C, 84.49; H, 3.94; N, 6.57. Measured elemental content (%): C, 84.45; H, 3.91; N, 6.53.

[0244] Synthesis Example 25: Synthesis of Compound 615

[0245]

[0246] Following the same preparation method as in Synthesis Example 1, dd-6 and ff-6 were replaced with equimolar amounts of dd-615 and ff-615, respectively, to obtain compound 615 (12.20 g, yield 67%). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 606.2316 (theoretical value: 606.2307). Theoretical elemental content (%) C 43 H 30 N2O2: C, 85.12; H, 4.98; N, 4.62. Measured elemental content (%): C, 85.16; H, 4.95; N, 4.67.

[0247] Synthesis Example 26: Synthesis of Compound 633

[0248]

[0249] Following the same preparation method as in Synthesis Example 1, aa-6, cc-6, and ff-6 were replaced with equimolar amounts of aa-633, cc-633, and ff-6, respectively, to obtain compound 633 (14.90 g, yield 72%). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 689.2369 (theoretical value: 689.2355). Theoretical elemental content (%) C 51 H 31 NO2: C, 88.80; H, 4.53; N, 2.03. Measured elemental content (%): C, 88.85; H, 4.50; N, 2.07.

[0250] Synthesis Example 27: Synthesis of Compound 685

[0251]

[0252] Following the same preparation method as in Synthesis Example 1, aa-6, cc-6, and ff-6 were replaced with equimolar amounts of cc-142, cc-685, and ff-57, respectively, to obtain compound 685 (12.67 g, yield 74%). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 570.1216 (theoretical value: 570.1224). Theoretical elemental content (%) C 38 H 22 N2S2: C, 79.97; H, 3.89; N, 4.91. Measured elemental content (%): C, 79.93; H, 3.85; N, 4.95.

[0253] Synthesis Example 28: Synthesis of Compound 748

[0254]

[0255] Following the same preparation method as in Synthesis Example 1, aa-6, cc-6, and ff-6 were replaced with equimolar amounts of aa-748, cc-441, and ff-748, respectively, to obtain compound 748 (13.56 g, yield 70%). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 645.1862 (theoretical value: 645.1875). Theoretical elemental content (%) C 44 H 27 N3OS: C, 81.84; H, 4.21; N, 6.51. Measured elemental content (%): C, 81.80; H, 4.24; N, 6.53.

[0256] Synthesis Example 29: Synthesis of Compound 749

[0257]

[0258] Following the same preparation method as in Synthesis Example 1, aa-6, cc-6, and ff-6 were replaced with equimolar amounts of aa-749, cc-749, and ff-749, respectively, to obtain compound 749 (15.13 g, yield 68%). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 741.2406 (theoretical value: 741.2416). Theoretical elemental content (%) C 53 H 31 N3O2: C, 85.81; H, 4.21; N, 5.66. Measured elemental content (%): C, 85.85; H, 4.17; N, 5.69.

[0259] Synthesis Example 30: Synthesis of Compound 752

[0260]

[0261] Following the same preparation method as in Synthesis Example 1, aa-6, cc-6, and ff-6 were replaced with equimolar amounts of aa-752, aa-6, and ff-353, respectively, to obtain compound 752 (12.71 g, yield 71%). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 596.2351 (theoretical value: 596.2340). Theoretical elemental content (%) C 42 H 16 D8N2O2: C, 84.54; H, 5.40; N, 4.69. Measured elemental content (%): C, 84.57; H, 5.44; N, 4.64.

[0262] Synthesis Example 31: Synthesis of Compound 769

[0263]

[0264] Following the same preparation method as in Synthesis Example 1, aa-6, cc-6, and ff-6 were replaced with equimolar amounts of aa-769, cc-769, and ff-769, respectively, to obtain compound 769 (12.72 g, yield 67%). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 632.1683 (theoretical value: 632.1671). Theoretical elemental content (%) C 42 H 24N4OS: C, 79.73; H, 3.82; N, 8.85. Measured elemental content (%): C, 79.78; H, 3.85; N, 8.81.

[0265] Synthesis Example 32: Synthesis of Compound 790

[0266]

[0267] Following the same preparation method as in Synthesis Example 1, dd-6 and ff-6 were replaced with equimolar amounts of dd-790 and ff-476, respectively, to obtain compound 790 (12.52 g, yield 69%). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 604.1625 (theoretical value: 604.1609). Theoretical elemental content (%) C 42 H 24 N₂OS: C, 83.42; H, 4.00; N, 4.63. Measured elemental content (%): C, 83.46; H, 4.03; N, 4.59.

[0268] Synthesis Example 33: Synthesis of Compound 866

[0269]

[0270] Following the same preparation method as in Synthesis Example 1, aa-6, cc-6, and ff-6 were replaced with equimolar amounts of aa-866, cc-142, and ff-292, respectively, to obtain compound 866 (13.74 g, yield 75%). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 610.1159 (theoretical value: 610.1174). Theoretical elemental content (%) C 40 H 22 N₂OS₂: C, 78.66; H, 3.63; N, 4.59. Measured elemental content (%): C, 78.62; H, 3.66; N, 4.54.

[0271] Synthesis Example 34: Synthesis of Compound 868

[0272]

[0273] Following the same preparation method as in Synthesis Example 1, dd-6 was replaced with an equimolar amount of dd-868 to obtain compound 868 (13.95 g, yield 71%). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 654.2320 (theoretical value: 654.2307). Theoretical elemental content (%) C 47 H 30N2O2: C, 86.22; H, 4.62; N, 4.28. Measured elemental content (%): C, 86.26; H, 4.65; N, 4.23.

[0274] Synthesis Example 35: Synthesis of Compound 896

[0275]

[0276] Following the same preparation method as in Synthesis Example 1, aa-6, cc-6, and ff-6 were replaced with equimolar amounts of cc-142, cc-896, and ff-292, respectively, to obtain compound 896 (12.00 g, yield 72%). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 555.1415 (theoretical value: 555.1405). Theoretical elemental content (%) C 37 H 21 N3OS: C, 79.98; H, 3.81; N, 7.56. Measured elemental content (%): C, 79.93; H, 3.85; N, 7.53.

[0277] Synthesis Example 36: Synthesis of Compound 897

[0278]

[0279] Following the same preparation method as in Synthesis Example 1, aa-6, cc-6, and ff-6 were replaced with equimolar amounts of ff-292, cc-897, and ff-897, respectively, to obtain compound 897 (13.10 g, yield 69%). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 632.1660 (theoretical value: 632.1671). Theoretical elemental content (%) C 42 H 24 N4OS: C, 79.73; H, 3.82; N, 8.85. Measured elemental content (%): C, 79.70; H, 3.85; N, 8.81.

[0280] Synthesis Example 37: Synthesis of Compound 898

[0281]

[0282] Following the same preparation method as in Synthesis Example 1, cc-6 and ff-6 were replaced with equimolar amounts of cc-898 and ff-57, respectively, to obtain compound 898 (12.74 g, yield 73%). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 581.1578 (theoretical value: 581.1562). Theoretical elemental content (%) C 39 H 23N3OS: C, 80.53; H, 3.99; N, 7.22. Measured elemental content (%): C, 80.57; H, 3.96; N, 7.25.

[0283] Synthesis Example 38: Synthesis of Compound 899

[0284]

[0285] Following the same preparation method as in Synthesis Example 1, aa-6, cc-6, and ff-6 were replaced with equimolar amounts of aa-899, cc-142, and ff-292, respectively, to obtain compound 899 (12.72 g, yield 70%). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 605.1576 (theoretical value: 605.1562). Theoretical elemental content (%) C 41 H 23 N3OS: C, 81.30; H, 3.83; N, 6.94. Measured elemental content (%): C, 81.26; H, 3.86; N, 6.97.

[0286] Synthesis Example 39: Synthesis of Compound 900

[0287]

[0288] Following the same preparation method as in Synthesis Example 1, aa-6, cc-6, and ff-6 were replaced with equimolar amounts of aa-900, cc-900, and cc-142, respectively, to obtain compound 900 (12.89 g, yield 69%). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 622.1273 (theoretical value: 622.1286). Theoretical elemental content (%) C 40 H 22 N4S2: C, 77.15; H, 3.56; N, 9.00. Measured elemental content (%): C, 77.11; H, 3.53; N, 9.03.

[0289] Synthesis Example 40: Synthesis of Compound 901

[0290]

[0291] Following the same preparation method as in Synthesis Example 1, aa-6, cc-6, and ff-6 were replaced with equimolar amounts of aa-901, cc-379, and ff-6, respectively, to obtain compound 901 (14.33 g, yield 65%). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 734.2155 (theoretical value: 734.2140). Theoretical elemental content (%) C 50 H 30N4OS: C, 81.72; H, 4.11; N, 7.62. Measured elemental content (%): C, 81.68; H, 4.14; N, 7.66.

[0292] Synthesis Example 41: Synthesis of Compound 902

[0293]

[0294] Following the same preparation method as in Synthesis Example 1, aa-6, cc-6, and ff-6 were replaced with equimolar amounts of aa-902, cc-142, and ff-292, respectively, to obtain compound 902 (11.71 g, yield 67%). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 582.1528 (theoretical value: 582.1514). Theoretical elemental content (%) C 38 H 22 N4OS: C, 78.33; H, 3.81; N, 9.62. Measured elemental content (%): C, 78.30; H, 3.85; N, 9.66.

[0295] The organic materials used in the device fabrication examples were all purified by sublimation, with a purity of over 99.99%. The ITO glass substrates and ITO / Ag / ITO glass substrates used in the device fabrication examples were purchased commercially.

[0296] The following are other compounds besides the heterocyclic compounds described in this invention used in the device fabrication examples:

[0297]

[0298]

[0299] A combined IVL testing system was constructed, consisting of testing software, a computer, a Keithley K2400 digital source meter, and a Photo Research PR788 spectrophotometer. The device prepared according to this invention was tested at atmospheric pressure and room temperature at a current density of 15 mA / cm². 2 The luminous efficiency and driving voltage were measured. Using McScience's M6000 OLED lifetime testing system, the lifetime (brightness decay to 95% of initial brightness) of the device prepared in this invention was tested at atmospheric pressure and room temperature. The test results are shown in Tables 1 to 3. Comparative device fabrication example 1: Comparative device 1

[0300] First, the ITO / Ag / ITO glass substrate is ultrasonically cleaned twice with deionized water for 20 minutes each time. Then, it is ultrasonically cleaned sequentially with isopropanol, acetone and methanol for 20 minutes each. After that, it is exposed to ultraviolet light and ozone for 30 minutes. Finally, it is placed in a vacuum evaporation equipment for later use.

[0301] The following layers were deposited layer by layer on the aforementioned ITO / Ag / ITO glass substrate: a) 2-TNATA as a hole injection layer with a thickness of 60 nm; b) NPB as a hole transport layer with a thickness of 40 nm; c) HOST-1 and Ir(dpm)(piq)2 (mass ratio 96:4) as a light-emitting layer with a thickness of 35 nm; d) NBphen and Liq (mass ratio 5:4) as an electron transport layer with a thickness of 35 nm; e) LiF as an electron injection layer with a thickness of 0.2 nm; f) Mg and Ag (mass ratio 7:1) as a cathode with a thickness of 10 nm; g) CP-4 as a capping layer with a thickness of 100 nm.

[0302] Comparative device fabrication example 2: Comparative device 2

[0303] By replacing HOST-1 with HOST-2 in the light-emitting layer, and following the same steps as in Comparative Device Fabrication Example 1, Comparative Device 2 can be obtained. Device Fabrication Examples 1-41: Light-emitting Devices 1-41

[0304] By replacing HOST-1 in the light-emitting layer with the heterocyclic compounds of the present invention described in Synthetic Examples 1 to 41, and taking the same steps as in Comparative Device Preparation Example 1, light-emitting devices 1 to 41 can be obtained.

[0305] Table 1

[0306]

[0307]

[0308]

[0309] Comparative device fabrication example 3: Comparative device 3

[0310] First, the ITO / Ag / ITO glass substrate is ultrasonically cleaned twice with deionized water for 20 minutes each time. Then, it is ultrasonically cleaned sequentially with isopropanol, acetone and methanol for 20 minutes each. After that, it is exposed to ultraviolet light and ozone for 30 minutes. Finally, it is placed in a vacuum evaporation equipment for later use.

[0311] The following layers were deposited layer by layer on the aforementioned ITO / Ag / ITO glass substrate: a) HATCN as a hole injection layer with a thickness of 5 nm; b) HT-9 as a hole transport layer with a thickness of 40 nm; c) HOST-1, H-4, and Ir(ppy)2(m-bppy) (mass ratio 48:48:4) as a light-emitting layer with a thickness of 35 nm; d) BAlq as a hole blocking layer with a thickness of 35 nm; e) NBphen and Liq (mass ratio 3:1) as an electron transport layer with a thickness of 25 nm; f) LiF as an electron injection layer with a thickness of 0.2 nm; g) Mg and Ag (mass ratio 1:3) as a cathode with a thickness of 10 nm; h) CP-4 as a capping layer with a thickness of 100 nm.

[0312] Comparative device fabrication example 4: Comparative device 4

[0313] By replacing HOST-1 with HOST-2 in the light-emitting layer, and following the same steps as in Comparative Device Fabrication Example 3, Comparative Device 4 can be obtained. Device Fabrication Examples 42-82: Light-emitting Devices 42-82

[0314] By replacing HOST-1 in the light-emitting layer with the heterocyclic compounds described in the present invention in Synthesis Examples 1 to 41, and taking the same steps as in Comparative Device Preparation Example 3, light-emitting devices 42 to 82 can be obtained.

[0315] Table 2

[0316]

[0317]

[0318] Comparative device fabrication example 5: Comparative device 5

[0319] First, the ITO / Ag / ITO glass substrate is ultrasonically cleaned twice with deionized water for 20 minutes each time. Then, it is ultrasonically cleaned sequentially with isopropanol, acetone and methanol for 20 minutes each. After that, it is exposed to ultraviolet light and ozone for 30 minutes. Finally, it is placed in a vacuum evaporation equipment for later use.

[0320] The following layers were deposited layer by layer on the aforementioned ITO / Ag / ITO glass substrate: a) HT-3 and p-1 (mass ratio 100:3) as a hole injection layer with a thickness of 25 nm; b) HT-3 as a hole transport layer with a thickness of 35 nm; c) NPB as a light-emitting auxiliary layer with a thickness of 30 nm; d) BH and BD (mass ratio 97:3) as a light-emitting layer with a thickness of 35 nm; e) HOST-1 as a hole blocking layer with a thickness of 30 nm; f) NBphen and Liq (mass ratio 3:1) as an electron transport layer with a thickness of 25 nm; f) LiF as an electron injection layer with a thickness of 0.2 nm; g) Mg and Ag (mass ratio 5:1) as a cathode with a thickness of 10 nm; h) CP-4 as a capping layer with a thickness of 100 nm. Comparative device fabrication examples 6-7: Comparative devices 6-7

[0321] By replacing HOST-1 in the hole blocking layer with HOST-2 and HB-1 respectively, and following the same steps as in Comparative Device Preparation Example 5, Comparative Devices 6 and 7 can be obtained.

[0322] Device fabrication examples 83-123: Light-emitting devices 83-123

[0323] By replacing HOST-1 in the hole blocking layer with the heterocyclic compounds of the present invention described in Synthetic Examples 1 to 41, and following the same steps as in Comparative Device Preparation Example 5, light-emitting devices 83 to 123 can be obtained.

[0324] Table 3

[0325]

[0326]

[0327] The device data in Tables 1 to 3 show that when the heterocyclic compound described in this invention is used as the host material of the light-emitting layer and the hole blocking layer, the driving voltage, luminous efficiency and lifespan of the device are significantly improved. This indicates that the heterocyclic compound described in this invention is a class of high-performance OLED materials with good application prospects.

[0328] It should be noted that the present invention has been specifically described with reference to individual embodiments, but those skilled in the art can make various forms or details of improvements to the present invention without departing from the principles of the present invention, and these improvements also fall within the protection scope of the present invention.

Claims

1. A heterocyclic compound, characterized by, having a structure represented by formula (I-A): wherein X1 is selected from an oxygen atom, a sulfur atom, or NR1, and R1 is, at each occurrence, the same or different, selected from one of substituted or unsubstituted phenyl, or substituted or unsubstituted naphthyl; X2 is selected from an oxygen atom or a sulfur atom; A is selected from one of the following structures: wherein said b 11 at each occurrence, is selected from 0, 1 or 2; said d 11 at each occurrence, is selected from 0, 1, 2 or 3; R as described in A 11 at each occurrence, is selected from one of a hydrogen atom, a deuterium atom; Ar1 is selected from one of the following structures: wherein said a 21 at each occurrence, is selected from 0, 1, 2, 3, 4, or 5, the same or different; said b 21 at each occurrence, is selected from 0, 1, 2, 3, 4, 5, 6, or 7, the same or different; R is selected from the group consisting of hydrogen atom, deuterium atom, phenyl group, deuterated phenyl group; when R 21a at each occurrence, is selected from the group consisting of hydrogen atom, deuterium atom, phenyl group, deuterated phenyl group; when R 21a when R is selected from phenyl group, deuterated phenyl group, a 21 is selected from 1; R is selected from the group consisting of hydrogen atom, deuterium atom, and halogen atom; 21 each occurrence is selected, identically or differently, from one of a hydrogen atom, a deuterium atom; L is selected from a methyl-substituted fluorenylene group or one of the following structures: wherein said a 41 at each occurrence, is selected from 0, 1, 2, 3, or 4, the same or different; said b 41 at each occurrence, is selected from 0, 1, 2, or 3, the same or different; said c 41 at each occurrence, is selected from 0, 1, or 2, the same or different; said f 41 at each occurrence, is selected from 0, 1, 2, 3, 4, or 5, the same or different; said g 41 at each occurrence, is selected from 0 or 1, the same or different; R is selected from the group consisting of hydrogen atom, deuterium atom, fluorine atom; 41 each occurrence is selected, identically or differently, from one of a hydrogen atom, a deuterium atom, a fluorine atom; X3 is selected from CR3 or a nitrogen atom, and R3 is selected from one of a hydrogen atom or a deuterium atom; B is selected from one of the following structures: said a 11 each occurrence is the same or different selected from 0, 1, 2, 3, or 4; said b 11 each occurrence is the same or different selected from 0, 1, or 2; R as described in B 11 in each occurrence, is selected, identically or differently, from one of a hydrogen atom, a deuterium atom, a cyano group; The substituents in "substituted or unsubstituted" are selected from a deuterium atom.

2. The heterocyclic compound according to claim 1, characterized by R1 is, at each occurrence, selected from one of substituted or unsubstituted phenyl.

3. The heterocyclic compound according to claim 1, characterized by A is selected from one of the following structures:

4. The heterocyclic compound according to claim 1, characterized by Ar1is selected from one of the following structures:

5. The heterocyclic compound according to claim 1, characterized by L is selected from one of the following structures: R is selected from the group consisting of hydrogen atom, deuterium atom, and halogen atom. 41 each occurrence is selected from the group consisting of hydrogen atom, deuterium atom, and halogen atom.

6. The heterocyclic compound according to claim 1, characterized by B is selected from one of the following structures:

7. A heterocyclic compound, characterized by, The heterocyclic compound is selected from one of the following structures:

8. An organic electroluminescent device comprising an anode, a cathode, and an organic layer comprising at least one of a hole transport region between the anode and the cathode, a light emitting layer, an electron transport region, and a cover layer on the side of the cathode facing away from the anode, characterized in that The organic layer contains one or more of the heterocyclic compounds of claims 1 to 7.

9. The organic electroluminescent device according to claim 8, wherein the organic layer comprises a hole transport region, a light emitting layer and an electron transport region between the anode and the cathode. At least one of the light-emitting layer and the electron-transporting region contains one or more of the heterocyclic compounds of claims 1 to 7.

10. The organic electroluminescent device according to claim 8, wherein the organic layer comprises a hole transport region between the anode and the cathode, a light emitting layer, an electron transport region, and a cover layer on the side of the cathode facing away from the anode. At least one of the light-emitting layer, the electron-transporting region, and the capping layer contains one or more of the heterocyclic compounds of claims 1 to 7.

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