Compounds and their applications

Abstract

This invention discloses a compound and its applications, belonging to the field of display technology. The chemical structural formula of the compound is as follows: at least one of Z1-Z6 is N, and the remainder is CH; L1, L2, and L3 are single bonds, C6-C30 arylene, or C3-C30 heteroarylene; Ar1-Ar4 are C6-C30 aryl or C3-C30 heteroaryl, and at least one of Ar1-Ar4 is the following chemical structural formula a: R1-R6 are one of hydrogen, deuterium, fluorine, or C1-C10 alkyl; one of B1-B4 is a linking site, and the remainder are one of hydrogen, deuterium, fluorine, methoxy, C1-C10 alkyl, C6-C30 aryl, or C3-C30 heteroaryl; n is an integer from 0 to 4. This compound is advantageous as an electron transport material and hole blocking material to improve the voltage, efficiency, and cycle life of OLED devices.

Description

Technical Field

[0001] This invention relates to the field of display technology, and in particular to compounds and their applications. Background Technology

[0002] Organic light-emitting devices (OLEDs), also known as organic light-emitting diodes, have advantages such as self-illumination, low power consumption, wide viewing angle, light weight, thinness, fast response, high contrast, low driving voltage, and flexibility, and are widely used in the fields of displays and lighting.

[0003] Typically, OLED devices include a cathode, an anode, and an electron transport layer, an emissive layer, and a hole transport layer stacked between the cathode and anode. The electron transport layer usually includes an electron transport layer (ETL) and a hole blocking layer (HBL). The electron transport material for the ETL typically requires high electron mobility, an energy level matching the emissive layer, good thermal stability, and excellent film-forming properties. The hole blocking material for the HBL requires deep HOMO energy levels to effectively block holes, a high triplet energy level, a suitable energy level, and good thermal stability.

[0004] However, there is still room for improvement in electron transport materials and hole blocking materials to enhance the operating voltage, efficiency, and lifespan of OLED devices. Summary of the Invention

[0005] In view of this, the present invention provides a compound and its application, which can solve the technical problems existing in related technologies. Specifically, it includes the following technical solutions: On the one hand, a compound is provided, the chemical structural formula of which is shown below:

[0006] Among them, at least one of Z1-Z6 is N, and the rest are CH; L1, L2, and L3 are each independently one of a single bond, a substituted or unsubstituted C6-C30 arylene, or a substituted or unsubstituted C3-C30 heteroarylene; Ar1-Ar4 are each independently one of a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C3-C30 heteroaryl group, and at least one of Ar1-Ar4 has the following chemical structural formula a: Chemical structural formula a R1-R6 are each independently one of hydrogen, deuterium, fluorine, or C1-C10 alkyl groups; One of B1-B4 is the linking site, and the others are each independently one of hydrogen, deuterium, fluorine, methoxy, C1-C10 alkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C3-C30 heteroaryl. n is an integer between 0 and 4.

[0007] In some possible implementations, two of L1, L2, and L3 are single bonds, and the remainder are substituted or unsubstituted C6-C30 arylene or substituted or unsubstituted C3-C30 heteroarylene. Alternatively, one of L1, L2, and L3 is a single bond, and the remaining two are independently substituted or unsubstituted C6-C30 arylene or substituted or unsubstituted C3-C30 heteroarylene. Alternatively, L1, L2, and L3 can each be independently a substituted or unsubstituted C6-C30 arylene or a substituted or unsubstituted C3-C30 heteroarylene.

[0008] In some possible implementations, the substituted or unsubstituted C6-C30 arylene and the substituted or unsubstituted C3-C30 heteroarylene include phenylene, biphenylene, naphthylene, fluorene, dibenzofuranyl, dibenzothiophene, phenanthrene, or benzonitrile. Optionally, when the C6-C30 arylene or the C3-C30 heteroarylene contains a substituent, the substituent includes deuterium.

[0009] In some possible implementations, at least one of Ar1-Ar4 has the chemical structural formula a; Alternatively, both Ar1 and Ar2 have the chemical structural formula a, and both Ar3 and Ar4 are substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C30 heteroaryl. Alternatively, Ar1 and Ar2 are both substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C30 heteroaryl, and both Ar3 and Ar4 are chemical structural formula a; Alternatively, one of Ar1 and Ar2 and one of Ar3 and Ar4 are chemical structures of formula a, and the remainder are substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C30 heteroaryl.

[0010] In some possible implementations, the substituted or unsubstituted C6-C30 aryl group and the substituted or unsubstituted C3-C30 heteroaryl group include phenyl, biphenyl, naphthyl, fluorenyl, dibenzofuranyl, dibenzothiopheneyl, phenanthryl or benzonitrile; Optionally, when the C6-C30 aryl or the C3-C30 heteroaryl contains a substituent, the substituent includes deuterium.

[0011] On the other hand, the application of any of the above compounds in organic electroluminescent devices, organic solar cells, organic thin-film transistors, organic photodetectors, organic field-effect transistors, organic integrated circuits, and organic photosensors is provided.

[0012] In another aspect, an electronic functional layer material is provided, which is an electron transport material or a hole blocking material, and the electronic functional layer material includes the above-mentioned compounds.

[0013] In some possible implementations, the electronic functional layer material is an electron transport material, which further includes a dopant compound with a mass percentage of less than or equal to 70 wt%. The doped compound is selected from at least one of the following: oxaoxazole compounds, thiazole compounds, triazole compounds, triazine compounds, triazabenzene compounds, oxalool compounds, diazanthracene compounds, silicon-containing heterocyclic compounds, quinoline compounds, phenanthroline compounds, metal chelates, fluorinated benzene compounds, and benzimidazole compounds; Optionally, the metal chelate is at least one of lithium hydroxyquinoline and its derivatives.

[0014] In another aspect, a light-emitting layer material is provided, the light-emitting layer material comprising a host material and a guest material, the host material comprising the aforementioned compound.

[0015] In another aspect, an organic electroluminescent device is provided, the organic electroluminescent device comprising: a first electrode, a second electrode, an electron transport functional layer, a light-emitting layer, and a hole transport functional layer stacked between the first electrode and the second electrode; At least one of the electron transport functional layer and the light-emitting layer includes the aforementioned compound.

[0016] In some possible implementations, the electron transport functional layer includes at least one of an electron injection layer, an electron transport layer, and a hole blocking layer, wherein at least one of the electron transport layer and the hole blocking layer includes the compound.

[0017] The beneficial effects of the technical solutions provided in the embodiments of the present invention include at least the following: The compound provided in this invention includes two sets of nitrogen-containing cyclic groups (e.g., triazine groups), at least one of which is connected to a benzocycloalkyl group as shown in chemical formula a. The introduction of the benzocycloalkyl group can effectively reduce the intermolecular interaction of the compound, significantly reduce the vapor deposition temperature of the molecule, improve the heat resistance of the compound molecule, and facilitate the formation of a stable and heat-resistant amorphous film, which is more beneficial for improving the glass transition temperature of the compound. The synergistic effect of the various groups in the compound makes this type of compound applicable as an electron transport material or hole blocking material in OLED devices, and exhibits the following advantages: (1) It has a high electron mobility, which is conducive to enhancing the balance of charge carrier transport, helping to reduce the voltage of the OLED device and improve its current efficiency. (2) It has a deep HOMO energy level and a suitable LUMO energy level, which can reduce the injection barrier of charge carriers, reduce the voltage of the OLED device and improve the device efficiency. The deep HOMO energy level is conducive to blocking holes migrating from the anode direction, reducing the leakage current of the OLED device. (3) It has a high T1 energy level, which can be used as an electron transport material to ensure the energy transfer efficiency between the host material and the guest light-emitting material, suppress energy loss, and improve the efficiency of exciton conversion luminescence. (4) It has a high glass transition temperature, which is beneficial to improving the phase stability and high temperature stability of the film made of the compound, and thus beneficial to improving the lifetime of OLED devices (including high temperature lifetime). Detailed Implementation

[0018] The technical solutions in the embodiments of the present invention will be clearly and completely described below. Obviously, the described embodiments are only some, not all, of the embodiments of the present invention. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without creative effort are within the scope of protection of the present invention.

[0019] In this embodiment of the invention, numerical ranges are involved. Unless otherwise specified, the numerical ranges are considered continuous and include the minimum and maximum values ​​of the range, as well as every value between the minimum and maximum values. Further, when the range refers to an integer, it includes every integer between the minimum and maximum values ​​of the range. Moreover, when multiple ranges are provided to describe features or characteristics, the ranges can be merged. In other words, unless otherwise specified, all ranges disclosed herein should be understood to include any and all subranges to which they are included.

[0020] Unless otherwise specified, the percentage concentrations mentioned in the embodiments of this invention refer to the final concentration. The final concentration refers to the proportion of the added component in the system after the addition of that component.

[0021] Unless otherwise specified, the temperature parameters in the embodiments of the present invention can be either constant temperature treatment or treatment within a certain temperature range. The constant temperature treatment allows temperature fluctuations within the precision range controlled by the instrument. The room temperature in the embodiments of the present invention generally refers to 4℃~30℃, preferably 20±5℃.

[0022] In a first aspect, embodiments of the present invention provide a compound, the chemical structural formula of which is shown below:

[0023] Among them, at least one of Z1-Z6 is N, and the rest are CH.

[0024] L1, L2, and L3 are each independently one of a single bond, a substituted or unsubstituted C6-C30 arylene, or a substituted or unsubstituted C3-C30 heteroarylene.

[0025] Ar1-Ar4 are each independently one of a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C3-C30 heteroaryl group, and at least one of Ar1-Ar4 has the following chemical structural formula a: Chemical structural formula a R1-R6 are each independently one of hydrogen, deuterium, fluorine, or C1-C10 alkyl groups.

[0026] One of B1-B4 is the linking site, and the others are each independently one of hydrogen, deuterium, fluorine, methoxy, C1-C10 alkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C3-C30 heteroaryl.

[0027] n is an integer between 0 and 4, meaning it can be 0, 1, 2, 3, or 4.

[0028] It should be noted that the "alkyl" involved in the embodiments of the present invention refers to a straight-chain or branched saturated hydrocarbon. The alkyl group can be a chain alkyl group or a cyclic alkyl group. Examples of chain alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, n-pentyl, isopentyl, neopentyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 4-methylhexyl, 5-methylhexyl, etc.

[0029] In this invention, the term "aryl" refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removing one hydrogen atom. This can be a monocyclic aryl, a fused-ring aryl, or a polycyclic aryl. For polycyclic compounds, at least one ring must be an aromatic ring system. For example, "C6-C30 aryl" refers to an aryl group containing 6-30 carbon atoms. Each occurrence can be independently C5, C6, C7, C8, C9, C10, C12, C14, C18, C20, C25, or C30 aryl. Suitable examples include, but are not limited to, benzene, biphenyl, naphthalene, anthracene, phenanthrene, dinaphthalene, triphenylene oxide, and their derivatives. Understandably, multiple aryl groups can also be interrupted by short non-aromatic units (e.g., <10% non-H atoms, such as C, N, or O atoms), specifically acenaphthene, fluorene, or 9,9-diarylfluorene, triarylamine, and diaryl ether systems should also be included in the definition of aryl.

[0030] "Aryl subunit" refers to the subunit of an aryl group. For the meaning and explanation of the aryl groups involved, please refer to the relevant explanations of aryl groups mentioned above.

[0031] In the embodiments of this invention, "heteroaryl" refers to an aryl group in which at least one carbon atom is replaced by a non-carbon atom, which can be an N atom, an O atom, an S atom, etc. For example, "C3~C30 heteroaryl" refers to a heteroaryl group containing 3 to 30 carbon atoms, and each occurrence can be independently C3 heteroaryl, C4 heteroaryl, C5 heteroaryl, C6 heteroaryl, C7 heteroaryl, C8 heteroaryl, C9 heteroaryl, C10 heteroaryl, C11 heteroaryl, C12 heteroaryl, C14 heteroaryl, C18 heteroaryl, C20 heteroaryl, C25 heteroaryl, and C30 heteroaryl. Suitable examples include, but are not limited to: furan, benzofuran, thiophene, benzothiophene, pyrrole, pyrazole, triazole, imidazole, oxazole, oxadiazole, thiazole, tetraazole, indole, carbazole, pyrroloimidazole, pyrrolopyrrole, thienopyrrole, thienothiophene, furanolopyrrole, furanolofuran, thienofuran, benzoisoxazole, benzoisothiazolium, benzimazole, pyridine, pyrazine, pyrimidine, triazine, quinoline, isoquinoline, o-diazonyl, quinoxaline, phenanthridine, primidine, quinazoline, and quinazolineone. Understandably, "azaaryl" refers to a heteroaryl group whose non-carbon atom is an nitrogen atom.

[0032] Regarding the linking bonds involved in the above compounds, one exemplary approach is that two of L1, L2, and L3 are single bonds, and the remaining bonds are substituted or unsubstituted C6-C30 arylene or substituted or unsubstituted C3-C30 heteroarylene. Another exemplary approach is that one of L1, L2, and L3 is a single bond, and the remaining two are each independently substituted or unsubstituted C6-C30 arylene or substituted or unsubstituted C3-C30 heteroarylene. Yet another exemplary approach is that all three bonds (L1, L2, and L3) are each independently substituted or unsubstituted C6-C30 arylene or substituted or unsubstituted C3-C30 heteroarylene.

[0033] By imposing the above constraints on L1, L2, and L3, it is beneficial to adjust the planarity and conjugation of the molecular structure, and to improve the film-forming properties of the molecule and regulate the carrier mobility.

[0034] Furthermore, the substituted or unsubstituted C6-C30 arylene groups and the substituted or unsubstituted C3-C30 heteroarylene groups involved in L1, L2, and L3 above include phenylene, biphenylene, naphthylene, fluorene, dibenzofuranyl, dibenzothiophene, phenanthrene, or benzonitrile. These groups, while satisfying the aforementioned effects, also facilitate the simplification of the compound's structure and preparation process.

[0035] Furthermore, when the above-mentioned C6-C30 arylene or C3-C30 heteroarylene contains a substituent, the substituent includes deuterium. By deuterating the above-mentioned group, it has the advantage of mitigating energy loss caused by high-frequency stretching vibration of CH and improving the lifespan and efficiency of the device.

[0036] For the aryl Ar1-Ar4 involved in the above compounds, an exemplary approach is that at least one of Ar1-Ar4 has the chemical structural formula a.

[0037] Another exemplary scheme is that both Ar1 and Ar2 are chemical structures of formula a, and both Ar3 and Ar4 are substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C30 heteroaryl.

[0038] Another exemplary scheme is that Ar1 and Ar2 are both substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C30 heteroaryl, and both Ar3 and Ar4 are chemical structural formula a.

[0039] Another exemplary scheme is that one of Ar1 and Ar2 and one of Ar3 and Ar4 are chemical structures of formula a, and the remainder are substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C30 heteroaryl.

[0040] When Ar1-Ar4 adopts the above-mentioned schemes, the HOMO / LUMO energy level and triplet energy level of the molecule can be further modified to meet the requirements of the carrier transport layer in different light-emitting (red, green, blue) devices.

[0041] Furthermore, the substituted or unsubstituted C6-C30 aryl groups and the substituted or unsubstituted C3-C30 heteroaryl groups involved in Ar1-Ar4 include phenyl, biphenyl, naphthyl, fluorenyl, dibenzofuranyl, dibenzothiophene, phenanthryl or benzonitrile. In addition to satisfying the above-mentioned effects, these groups also help to simplify the structure and preparation process of the compound.

[0042] Furthermore, when C6-C30 aryl or C3-C30 heteroaryl contains substituents, such substituents include deuterium. By deuterating the above groups, it has the advantage of mitigating energy loss caused by high-frequency stretching vibrations of CH and improving the lifespan and efficiency of the device.

[0043] Regarding the compounds mentioned above, some examples of these compounds are listed below, see compounds 1-436.

[0044]

[0045] Secondly, embodiments of the present invention provide the application of any of the above-mentioned compounds in organic electroluminescent devices, organic solar cells, organic thin-film transistors, organic photodetectors, organic field-effect transistors, organic integrated circuits, or organic photoreceptors.

[0046] When the compound is applied to an organic electroluminescent device, it can be used to form the light-emitting layer, hole-blocking layer, or electron transport layer of the organic electroluminescent device.

[0047] In some embodiments of the present invention, the compound can be used to form the electron transport layer of an organic electroluminescent device, thereby enabling the organic electroluminescent device to have both high luminous efficiency, low operating voltage and strong thermal stability.

[0048] In some embodiments of the present invention, the compound can be used to form a hole blocking layer in an organic electroluminescent device, which can effectively block holes from entering the electron transport layer, increase electron recombination in the light-emitting layer, and improve luminous efficiency.

[0049] In some embodiments of the present invention, the compound can be used to form the light-emitting layer of an organic electroluminescent device, particularly as the host material of the light-emitting layer, which facilitates the injection of electrons from the electron transport layer into the light-emitting layer, improves the balance of electrons and holes in the light-emitting layer, and enhances the luminous efficiency.

[0050] Thirdly, embodiments of the present invention provide an electronic functional layer material, which is an electron transport material or a hole blocking material, and the electronic functional layer material includes any of the compounds involved in the first aspect above.

[0051] The electronic functional layer material provided in the embodiments of the present invention has all the advantages of the compounds involved in the embodiments of the present invention.

[0052] The electronic functional layer material provided in this invention can be used as an electron transport material and to prepare the electron transport layer of an organic electroluminescent device when applied to an organic electroluminescent device, so that the organic electroluminescent device has both high luminous efficiency, low operating voltage and strong thermal stability.

[0053] The electronic functional layer material provided in this invention can be used as a hole blocking material in organic electroluminescent devices and can be used to prepare the hole blocking layer of organic electroluminescent devices. It can effectively block holes from entering the electron transport layer, increase the recombination of electrons in the light-emitting layer, and improve the luminous efficiency.

[0054] In some examples, the mass percentage of any compound involved in the first aspect of the present invention in the electronic functional layer material is 100%.

[0055] For example, when this electronic functional layer material is used to prepare an electron transport layer or a hole blocking layer, the compound can be used alone.

[0056] In other examples, the electronic functional layer material provided in the embodiments of the present invention is an electron transport material, which includes any of the compounds and doped compounds involved in the first aspect, wherein the mass percentage of the doped compound is less than or equal to 70 wt%, for example, 1 wt%-70 wt%, including but not limited to the range of one or any two of the following values: 2%, 4%, 6%, 8%, 10%, 12%, 14%, 16%, 18%, 20%, 22%, 24%, 26%, 28%, 29%, 30%, 32%, 34%, 36%, 38%, 40%, 42%, 44%, 46%, 48%, 50%, 52%, 54%, 56%, 58%, 60%, 62%, 64%, 66%, 68%, 69%, 70%, etc.

[0057] For this example, the compound has a mass percentage in the electron transport material greater than or equal to 30 wt%, for example, 30 wt% to 99 wt%, including but not limited to one or any two of the following values: 30%, 32%, 34%, 36%, 38%, 40%, 42%, 44%, 46%, 48%, 50%, 52%, 54%, 56%, 58%, 60%, 62%, 64%, 66%, 68%, 69%, 70%, 72%, 74%, 76%, 78%, 80%, 82%, 84%, 86%, 88%, 90%, 92%, 94%, 96%, 98%, 99%, etc.

[0058] Furthermore, for this type of electron transport material, the mass percentage of the doped compound is 20wt%-70wt%, and the mass percentage of the compound in the electron transport material is 30wt%-80wt%.

[0059] Some suitable doping compounds are selected from at least one of the following: oxaoxazole compounds, thiazole compounds, triazole compounds, triazine compounds, triazabenzene compounds, oxalool compounds, diazanthracene compounds, silicon-containing heterocyclic compounds, quinoline compounds, phenanthroline compounds, metal chelates, fluorinated benzene compounds, and benzimidazole compounds.

[0060] Furthermore, the metal chelate is selected from at least one of lithium hydroxyquinoline and its derivatives, and further, the lithium hydroxyquinoline is 8-hydroxyquinoline lithium.

[0061] The aforementioned doping compounds possess suitable electron affinity and excellent electron transport properties. By enabling the doping compounds to work synergistically with the aforementioned compounds, it is beneficial to further improve the electron injection efficiency and transport rate, thereby reducing the operating voltage of OLED devices and improving the luminous efficiency of the devices.

[0062] For further examples, when the aforementioned electron transport material is used to prepare a hole-blocking layer, the doping compound used can be an oxaoxazole compound, a thiazole compound, a triazole compound, or a triazine compound. Furthermore, the hole-blocking material is typically used alone.

[0063] Fourthly, embodiments of the present invention provide a light-emitting layer material, which includes a host material and a guest material, wherein the host material includes the compound involved in the first aspect of the present invention.

[0064] The light-emitting layer material provided in this embodiment of the invention possesses all the advantages of the compounds involved in this embodiment. Specifically, it facilitates the injection of electrons from the electron transport layer into the light-emitting layer, resulting in a more balanced distribution of electrons and holes in the light-emitting layer, thereby improving the luminous efficiency of OLED devices.

[0065] In some examples, the host material also includes at least one of the following luminescent host compounds: naphthalene compounds, pyrene compounds, fluorene compounds, phenanthrene compounds, chrysene compounds, fluoranthene compounds, anthracene compounds, pentanebenzene compounds, perylene compounds, diarylethene compounds, triphenylamine ethylene compounds, amine compounds, carbazole compounds, benzimidazole compounds, furan compounds, organometallic fluorescent complexes, organometallic phosphorescent complexes, boron nitrogen compounds, polyvinylcarbazole, polyorganosilicon compounds, and polythiophene. Further, the organometallic phosphorescent complex may contain elements such as Ir, Pt, Os, Cu, or Au.

[0066] The mass percentage of the luminescent host compound in the host material can be 1%-20%, and the mass percentage of the luminescent host compound includes, but is not limited to, any one of the following values ​​or a range consisting of any two of the following values: 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 19%, 20%.

[0067] By employing the synergistic effect of the aforementioned host luminescent compound and the target compound provided in the embodiments of this invention, while ensuring the luminous efficiency of the OLED light-emitting device, it is also beneficial to optimize charge transport balance, reduce non-radiative losses, and improve device stability. Furthermore, it facilitates the regulation of exciton distribution in the luminescent layer, suppresses exciton quenching, and broadens luminous adaptability.

[0068] Furthermore, the luminescent host compound may be selected from at least one of pyrene compounds, chrysene compounds, diarylethene compounds, organometallic fluorescent complexes, organometallic phosphorescent complexes, and boron nitrogen compounds.

[0069] The guest material can be any of the guest materials currently used in OLED devices. This invention does not specifically limit it and can be selected adaptively according to actual light emission requirements.

[0070] Fifthly, embodiments of the present invention provide an organic electroluminescent device, the organic electroluminescent device comprising: a first electrode, a second electrode, an electron transport functional layer, an emissive layer, and a hole transport functional layer stacked between the first electrode and the second electrode; wherein at least one of the electron transport functional layer and the emissive layer comprises the compound involved in the first aspect of the present invention.

[0071] Specifically, the electron transport functional layer includes the electron transport material involved in the third aspect of the present invention. The light-emitting layer may include the light-emitting layer material involved in the fourth aspect of the present invention.

[0072] The organic electroluminescent device provided in this embodiment of the invention possesses all the advantages of the compounds involved in this embodiment. For example, the organic electroluminescent device combines high luminous efficiency, low operating voltage, and strong thermal stability.

[0073] In some examples, the electron transport functional layer includes at least one of an electron injection layer, an electron transport layer, and a hole blocking layer, wherein at least one of the electron transport layer and the hole blocking layer includes the electron transport material involved in the third aspect of the present invention.

[0074] The following examples illustrate this point.

[0075] As an example, the electron transport functional layer includes an electron transport layer, wherein the cathode, electron transport layer, light-emitting layer, and hole transport functional layer are stacked in sequence.

[0076] As another example, the electron transport functional layer includes an electron transport layer and an electron injection layer, wherein the cathode, electron injection layer, electron transport layer, light-emitting layer, and hole transport functional layer are stacked in sequence.

[0077] As another example, the electron transport functional layer includes an electron transport layer and a hole blocking layer, wherein the cathode, electron transport layer, hole blocking layer, light-emitting layer, and hole transport functional layer are stacked in sequence.

[0078] As another example, the electron transport functional layer includes an electron transport layer, a hole blocking layer, and an electron injection layer, wherein the cathode, electron injection layer, electron transport layer, hole blocking layer, light-emitting layer, and hole transport functional layer are stacked in sequence.

[0079] In the various examples mentioned above, at least one of the electron transport layer and the hole blocking layer includes the compounds involved in the embodiments of the present invention. Specifically, both the electron transport layer and the hole blocking layer can be made of the electron transport material involved in the third aspect of the embodiments of the present invention.

[0080] For the aforementioned electron injection layer, the electron injection materials used include, but are not limited to, alkali metals, alkali metal-containing compounds, alkaline earth metals, alkaline earth metal-containing compounds, and alkaline earth metal-containing complexes. Further, the electron injection layer materials include, but are not limited to: alkali metals, alkaline earth metals, rare earth metals, oxides or halides of alkali metals, oxides or halides of alkaline earth metals, oxides or halides of rare earth metals, and organic complexes of alkali metals or alkaline earth metals. Even further, the electron injection layer materials include, but are not limited to: lithium, lithium fluoride, lithium oxide, lithium nitride, lithium 8-hydroxyquinoline, cesium, cesium carbonate, cesium 8-hydroxyquinoline, calcium, calcium fluoride, calcium oxide, magnesium, magnesium fluoride, magnesium carbonate, and magnesium oxide.

[0081] For a hole transport functional layer, in some examples, the hole transport functional layer includes at least one of a hole injection layer, a hole transport layer, and an electron blocking layer.

[0082] The following examples illustrate this point.

[0083] As an example, the hole transport functional layer includes a hole injection layer and a hole transport layer, wherein the anode, hole injection layer, hole transport layer, light emission layer, and electron transport functional layer are stacked in sequence.

[0084] As another example, the hole transport functional layer includes a hole transport layer and an electron blocking layer, wherein the anode, hole transport layer, electron blocking layer and light-emitting layer are stacked in sequence.

[0085] As another example, the hole transport functional layer includes a hole transport layer, an electron blocking layer, and a hole injection layer, wherein the anode, hole injection layer, hole transport layer, electron blocking layer, light-emitting layer, and electron transport functional layer are stacked in sequence.

[0086] The hole transport functional material used in the hole transport functional layer can be selected from at least one of carbazole compounds, triaromatic amine compounds, benzene diamine compounds, fluorene compounds, phthalocyanine compounds, polythiophene, polyethylene, polybenzene sulfonic acid, quinone compounds (e.g., 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanodimethyl-p-benzoquinone (F4-TCNQ)), and hexacyanohexatribenzene. For example, this could be a triaromatic amine compound, benzene diamine compound, carbazole compound, polyvinylcarbazole, etc.

[0087] For any of the organic electroluminescent devices mentioned above, the total thickness of the organic layer (i.e., electron transport functional layer + light-emitting layer + hole transport functional layer) between the cathode and anode can be 1nm-1000nm, including but not limited to any of the following values ​​or a range consisting of any two values: 1nm, 30nm, 50nm, 100nm, 150nm, 200nm, 300nm, 400nm, 500nm, 550nm, 600nm, 700nm, 750nm, 800nm, 850nm, 900nm, 950nm, 1000nm, etc.

[0088] Furthermore, the total thickness of the organic layer can be 50nm-500nm, including but not limited to any of the following values ​​or a range consisting of any two values: 50nm, 100nm, 150nm, 200nm, 250nm, 300nm, 350nm, 400nm, 450nm, and 500nm.

[0089] In some embodiments of the present invention, the preparation method for each functional layer of the organic layer of the organic electroluminescent device includes: vacuum evaporation, molecular beam evaporation, solvent-based dip coating, spin coating, bar coating, or inkjet printing.

[0090] It should be noted that the organic layers in the organic electroluminescent devices involved in the embodiments of the present invention can be prepared by vacuum evaporation, molecular beam evaporation, solvent-based dip coating, spin coating, rod coating, or inkjet printing. Metal electrodes can be prepared by evaporation or sputtering.

[0091] In a sixth aspect, embodiments of the present invention also provide a display device, which includes the organic electroluminescent device provided in the fifth aspect of embodiments of the present invention.

[0092] The display device provided in this embodiment of the invention uses the organic electroluminescent device mentioned above, which helps to reduce power consumption and extend its lifespan.

[0093] For example, the display device may be a mobile phone, tablet, laptop, wearable device, television, electronic screen, vehicle display, special display device, etc.

[0094] The specific embodiments of the present invention will now be described in more detail. While specific embodiments of the present invention are described below, it should be understood that the present invention can be implemented in various forms and should not be limited to the embodiments set forth herein. Where specific techniques or conditions are not specified in the embodiments, they are performed in accordance with the techniques or conditions described in the literature in the art or according to the product instructions. Reagents or instruments whose manufacturers are not specified are all conventional products that can be obtained commercially.

[0095] It should be noted that the serial numbers of the compounds provided in the following embodiments are the same as the compounds with the same serial numbers among the aforementioned compounds 1-436.

[0096] The following examples involve the synthesis of compounds, including intermediate compounds (hereinafter referred to as intermediates). These compounds and intermediates were separated by column chromatography and characterized by molecular structure using a 1HRMS (1-resolution mass spectrometer).

[0097] Intermediate Synthesis Examples Synthetic intermediate C1:

[0098] Starting materials A1 (10.0 g, 44.24 mmol), B1 (19.26 g, 42.02 mmol), and potassium carbonate (9.17 g, 66.35 mmol) were added to a three-necked flask, followed by toluene (60 mL), ethanol (30 mL), and deionized water (30 mL). Under nitrogen protection, 0.2 g (0.28 mmol) of di-triphenylphosphine palladium chloride was added, and the mixture was refluxed for 10 h. After the reaction was complete, the mixture was separated, the solvent was concentrated, and the crude product was separated by column chromatography using dichloromethane:petroleum ether (v / v = 2:1) as the eluent, yielding a white product, which was intermediate C1, with a yield of 13.16 g and a yield of 57%. The relevant characterization is shown below: HRMS (ESI, m / z): [M+H] + calcdfor: C 34 H 21 ClN3O, 522.1368, found, 522.1372. Anal.: calcd: C, 78.23; H, 3.86; Cl, ​​6.79; N, 8.05; O, 3.06; found: C, 78.11; O,3.13.

[0099] Synthetic intermediate E1:

[0100] The synthesis method of intermediate E1 is the same as that of intermediate C1, except that intermediate B2 is 1.05 eq. Relevant characterization is shown below: HRMS (ESI, m / z): [M+H] + calcd for: C 28 H 27 ClN3, 440.1888, found, 440.1896.Anal.: calcd: C, 76.44; H, 5.96; Cl, ​​8.06; N, 9.55;

[0101] Synthetic intermediate G1:

[0102] Intermediate E1 (6.0 g, 13.64 mmol), starting material F1 (4.16 g, 16.36 mmol), potassium acetate (2.68 g, 27.27 mmol), and anhydrous toluene (60 mL) were added to a three-necked flask. Under nitrogen protection, Pd2(dba)3 (0.06 g, 0.066 mmol) and X-phos (0.12 g, 0.168 mmol) were added, and the mixture was refluxed for 7 h. TLC showed complete reaction. The mixture was then filtered through a thin layer of silica gel while hot to remove inorganic salts. The filtrate was concentrated to approximately 10 mL, cooled, stirred to induce crystallization, and washed with a small amount of toluene. After drying, a white solid powder was obtained, which was intermediate G1, with a yield of 5.72 g and a yield of 79%. The relevant characterization is shown below: HRMS (ESI, m / z): [M+H] + calcd for: C 34 H 39 BN3O2, 532.3130, found, 532.3124. Anal.: calcd: C,76.83; H, 7.21; B, 2.03; N, 7.91; O, 6.02; found: C, 76.76; 6.08.

[0103] Synthetic intermediate J1:

[0104] The synthesis method of intermediate J1 is the same as that of intermediate C1, except that intermediate H1 is 1.1eq.

[0105] The relevant characterization is shown below: HRMS (ESI, m / z): [M+H] + calcd for: C 27 H 17 ClN3O, 434.1055, found, 434.1049. Anal.: calcd: C, 74.74; H, 3.72; Cl, ​​8.17; N, 9.68; O, 3.69; found: C, 74.82;

[0106] Other intermediates C were prepared using the same synthetic method as intermediate C1, except that the raw materials were different. The relevant information is shown in Table 1.

[0107]

[0108] Other intermediates E were prepared using the same synthesis method as intermediate E1, except that the raw materials were different. The relevant information is shown in Table 2.

[0109]

[0110] Other intermediates G were prepared using the same synthetic method as intermediate G1, except that the raw materials were different. The relevant information is shown in Table 3.

[0111]

[0112] Other intermediates J were prepared using the same synthesis method as intermediate J1, except that the raw materials were different. The relevant information is shown in Table 4.

[0113]

[0114] Compound Synthesis Examples Example 1 Example 1 provides compound 22, the synthetic route of which is shown below:

[0115] The synthetic method for compound 22 can be found in the synthetic method for intermediate E1. The relevant characterization of compound 22 is shown below: HRMS (ESI, m / z): [M+H] + calcd for: C 62 H 47 N6O, 891.3806, found, 891.3811.Anal.: calcd: C, 83.57; H, 5.20; N, 9.43; O, 1.80;

[0116] Example 2 Example 2 provides compound 81, the synthetic route and method of which are shown below:

[0117] Intermediate E3 (4.0 g, 10.44 mmol), intermediate G4 (5.88 g, 10.96 mmol), and potassium carbonate (2.16 g, 15.66 mmol) were added to a three-necked flask, followed by toluene (24 mL), ethanol (12 mL), and deionized water (12 mL). Under nitrogen protection, palladium acetate (0.08 g, 0.356 mmol) and X-phos (0.16 g, 0.224 mmol) were added, and the mixture was refluxed for 6 h. After the reaction was complete, the mixture was separated, the solvent was concentrated, and the crude product was separated by column chromatography using dichloromethane:petroleum ether (v / v = 2:1) as the eluent to obtain a white product, which was compound 81, with a yield of 6.00 g and a yield of 76%. The relevant characterization of compound 81 is shown below: HRMS (ESI, m / z): [M+H] + calcd for: C 52 H 36 N7, 758.3027, found, 758.3032. Anal.: calcd:C, 82.41; H, 4.65; N, 12.94; found: C, 82.48; H, 4.62; N, 12.90.

[0118] Example 3 Example 3 provides compound 113, the synthetic route of which is shown below:

[0119] The synthesis method of compound 113 is the same as that of intermediate C1, except that intermediate G5 is 2.1 eq. The relevant characterization of compound 113 is shown below: HRMS (ESI, m / z): [M+H] + calcd for: C 55 H 40 N7, 798.3340, found,798.3344. Anal.: calcd: C, 82.79; H, 4.93; N, 12.29; found: C, 82.84; H, 4.92; N, 12.24.

[0120] Other compounds were synthesized using the same synthetic method as compound 22, with the difference being the different starting materials. Relevant information is shown in Table 5.

[0121]

[0122] Other compounds were prepared using the same synthetic method as compound 81, except that the raw materials were different. The relevant information is shown in Table 6.

[0123]

[0124] Other compounds were prepared using the same synthetic method as compound 113, except for the different starting materials. Relevant information is shown in Table 7.

[0125]

[0126] Test case The physical and photoelectric properties of the compounds prepared in the above embodiments of the present invention were tested, and the test results are shown in Table 8.

[0127] It should be noted that the triplet energy level T1 is derived from Horiba's Fluorolog. The material was tested using a 3-series fluorescence spectrometer. The test sample was a 0.00002 mol / L toluene solution.

[0128] The glass transition temperature Tg was obtained by differential scanning calorimetry (Pyris Diamond (DSC 2920) differential scanning calorimeter) under nitrogen protection, with heating and cooling rates of 10 °C / min.

[0129] The highest occupied molecular orbital (HOMO) energy level was measured by the ionization energy testing system (AC-2) in an atmospheric environment.

[0130] LUMO = HOMO + Eg, where Eg was measured using a dual-beam UV-Vis spectrophotometer (model: Hatachi U2900).

[0131] The LUMO energy levels of each compound in a vacuum environment were measured using an AC-2 photoelectron spectrometer. The specific testing method is as follows: Each compound was deposited on an ITO substrate to form a thin film. The AC-2 testing conditions were 50 nW - step 0.05 nW, and the LUMO energy levels of each compound were measured. The band gap (Eg) of the material was measured using a UV spectrophotometer, and the HOMO energy levels of the compounds were calculated from the LUMO energy levels and Eg.

[0132] Electron mobility was measured as follows: Single-charge devices were fabricated using various compounds and LiQ as electron transport materials, and the results were measured using the space-charge-limited current (SCLC) method. The single-charge device consisted of a substrate / anode, a hole injection layer, an electron transport layer, an electron injection layer, and a cathode, stacked sequentially.

[0133] The fabrication method for a single electronic device is as follows: Substrate / Anode: The glass substrate with an ITO (Indium Tin Oxide)-Ag-ITO (Indium Tin Oxide) surface layer was cleaned twice with distilled water, ultrasonically cleaned for 30 minutes in a commercial cleaning agent, and then repeatedly cleaned twice with distilled water and ultrasonically cleaned for 10 minutes. After cleaning, it was ultrasonically cleaned sequentially with ethanol, acetone, and isopropanol (5 minutes each time), and dried. Then it was transferred to a plasma cleaner for 5 minutes, baked in a clean environment until all moisture was removed, cleaned with ultraviolet photosynthetic ozone, treated with oxygen plasma for 30 seconds, and then sent to the vacuum chamber of an evaporation deposition machine for evaporation. Using this substrate as the anode, other functional layers were sequentially deposited on it.

[0134] Hole injection layer: LiQ (10 nm thick) was deposited on the ITO surface as a hole injection layer at a deposition rate of 0.1 nm / s.

[0135] Electron transport layer: The above-mentioned compounds and LiQ (thickness of 60 nm) are vapor-deposited on the surface of the hole injection layer as an electron transport layer, wherein the mass percentage of the compounds and lithium 8-hydroxyquinoline (LiQ) is 50% each, and the two are combined to form an electron transport material. The vapor deposition rate of both is 0.05 nm / s.

[0136] Electron injection layer: Yb (1 nm thick) is deposited on the surface of the electron transport layer as an electron injection layer at a deposition rate of 0.1 nm / s.

[0137] Cathode: Ag: 10wt% Mg (thickness 14nm) was vapor-deposited on the surface of the electron injection layer as the cathode. The vapor deposition rate of Ag was 0.09nm / s and the vapor deposition rate of Mg was 0.01nm / s.

[0138] Table 8 shows the electron mobility of the electron transport layer corresponding to each electron transport material at a thickness of 60 nm. The electron mobility in Table 8 is expressed in scientific notation. In this embodiment of the invention, the value aE-b described in scientific notation is equivalent to a × 10⁻⁶. b For example, 1×10 5 It can be recorded as 1E-05.

[0139] As shown in Table 8, all compounds provided in the embodiments of the present invention have high glass transition temperatures (Tg), all above 150°C, and even as high as 160°C, exhibiting excellent thermal stability. This is beneficial for improving the phase stability and high-temperature stability of the films made from them, thereby enhancing the lifespan and luminous stability of organic electroluminescent devices.

[0140] The compounds provided in the embodiments of this invention all possess deep HOMO energy levels and suitable LUMO energy levels. Deeper HOMO energy levels are beneficial for blocking holes migrating from the anode direction, reducing leakage current in OLED devices, and improving device current efficiency. Furthermore, deeper HOMO energy levels also help reduce the number of holes leaving the emissive layer, increasing the recombination probability of electrons and holes in the emissive layer, making these compounds suitable as hole-blocking materials. Moreover, the deep HOMO energy levels and suitable LUMO energy levels of the compounds also help reduce the carrier injection barrier, lower device voltage, and improve device efficiency, making these compounds suitable as electron transport materials.

[0141] The compounds provided in the embodiments of this invention possess high triplet energy levels (T1 levels). When used as electron transport materials, they can ensure efficient energy transfer between host and guest electrons and suppress energy loss. Furthermore, the high triplet energy levels also help reduce the number of excitons leaving the luminescent layer, thereby improving the efficiency of exciton conversion luminescence.

[0142] The compounds provided in the embodiments of the present invention also have high electron mobility, which helps to improve the voltage and current efficiency of OLED devices, especially the turn-on voltage.

[0143] Application Examples The following examples, Application Examples 1-31 and Comparative Examples 1-8, further illustrate the application effects of the compounds provided in the above examples in OLED devices. The OLED devices involved in Application Examples 1-31 and Comparative Examples 1-8 have the same fabrication process, use the same substrate material and electrode material, and the film thickness of the electrode material is also consistent. The difference lies in the electron transport layer or hole blocking layer of the different OLED devices.

[0144] OLED devices consist of the following layers stacked sequentially: anode / substrate - hole injection layer - hole transport layer - electron blocking layer - light-emitting layer - hole blocking layer - electron transport layer - electron injection layer - cathode.

[0145] The fabrication method of OLED devices is as follows: The transparent conductive ITO glass substrate (with an anode) (China Southern Glass Group Co., Ltd.) was ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, and then sequentially washed with ethanol, acetone, and deionized water. It was then baked in a clean environment until all moisture was removed, cleaned with ultraviolet photosynthetic ozone, and treated with oxygen plasma for 30 seconds. The anode-bearing glass substrate was then placed in a vacuum chamber and evacuated.

[0146] Hole injection layer: Compound HT and P-dopant (P-dopant doping concentration of 3%) were deposited on ITO as hole injection layer with a thickness of 10 nm and a deposition rate of 0.1 nm / s.

[0147] Hole transport layer: Compound HT is deposited on the hole injection layer to form a 120 nm thick hole transport layer at a deposition rate of 0.1 nm / s.

[0148] Electron blocking layer: Compound EB was deposited on the surface of the hole transport layer to form a 10 nm thick electron blocking layer. The deposition rate was 0.1 nm / s.

[0149] Emitting layer: A 20nm thick emitting layer is deposited on the electron blocking layer. The emitting layer includes compound BH and guest material BD. BH is the host emitting material and BD is the phosphorescent dopant guest material with a doping mass percentage of 2% and a deposition rate of 0.1nm / s.

[0150] Hole blocking layer: Compound HB or the test compound is deposited on the surface of the light-emitting layer to form a 5 nm thick hole blocking layer at a deposition rate of 0.1 nm / s.

[0151] Electron transport layer: The test compound (or compound ET-1):LiQ (both with a mass percentage of 50%) was deposited on the surface of the hole blocking layer as the electron transport layer. LiQ is lithium 8-hydroxyquinoline. The deposition rate was 0.1 nm / s and the thickness was 30 nm.

[0152] Electron injection layer: A 1 nm thick LiQ layer is deposited on the surface of the electron transport layer as the electron injection layer.

[0153] Cathode: A cathode with a thickness of 120 nm and made of Al was fabricated on the surface of the electron injection layer.

[0154] The composition of the hole blocking layer and electron transport monolayer of the fabricated OLED device is shown in Table 9 below.

[0155]

[0156] The raw material compounds involved in the fabrication of the aforementioned OLED devices are shown below:

[0157]

[0158]

[0159]

[0160]

[0161] The performance of each OLED device listed in Table 9 was tested. During the test, a known driving circuit was used to connect the anode and cathode. The test items are shown below.

[0162] The performance of the OLED devices provided in Application Examples 1-31 and Comparative Examples 1-8 was tested. During the test, a known driving circuit was used to connect the anode and cathode. The test items and results are shown below.

[0163] (1) Driving voltage, efficiency, and color coordinates: The device was analyzed at 1000 cd / cm² using a Photo Research PR655 spectrometer. 2 Drive voltage, efficiency, and color coordinates at luminance. The unit for drive voltage is V, the unit for current efficiency is cd / A, and the unit for external quantum efficiency (EQE) is %.

[0164] (2) Device lifetime at room temperature: The time it takes for the brightness of the device to decay to 95% of its initial brightness at a current density of 20 mA / cm² and at room temperature (LT95). The lifetime testing system is the M6400 OLED device lifetime tester from MCSCIENCE, South Korea. The unit of device lifetime is Hr.

[0165] (3) High-temperature lifespan of the device (also known as 85°C lifespan): The time it takes for the brightness of the device to decay to 95% of its initial brightness when the current density is 20mA / cm² and the temperature is 85°C. The unit of high-temperature lifespan is Hr.

[0166] (4) Start-up voltage: The driving voltage when the brightness of the test device is 1 nit. The unit of start-up voltage is V.

[0167] (5) Power efficiency: Tested under a current density of 10mA / cm², where the unit of power efficiency is lm / W.

[0168] (6) Efficiency attenuation coefficient , , This is expressed as the device's maximum current efficiency. This indicates a drive current of 50mA / cm. 2 At that time, the current efficiency of the device. The larger the value, the more severe the efficiency roll-off of the device; conversely, the smaller the value, the better the problem of rapid degradation of the device under high current density has been controlled.

[0169] The relevant test data are shown in Table 10:

[0170] As shown in Table 10, when the electron transport layer or hole blocking layer is prepared using the compounds provided in the embodiments of the present invention, the OLED devices exhibit a turn-on voltage of less than or equal to 2.8V, a driving voltage of less than or equal to 3.60V, a current efficiency greater than 6cd / A, an external quantum efficiency greater than or equal to 8%, a power efficiency greater than or equal to 5lm / W, a room temperature lifetime greater than 240 hours, and a high temperature lifetime greater than 160 hours. Compared with the comparative example OLED devices, the OLED devices provided in the application embodiments of the present invention all exhibit lower voltage, higher efficiency, and longer lifetime, with the improvement in lifetime being particularly significant.

[0171] In addition, Table 10 also shows that the OLED devices prepared using the compounds of the present invention have a smaller efficiency decay coefficient. It can be seen that the efficiency roll-off problem of these OLED devices at high current densities has been effectively controlled.

[0172] In summary, compared with the comparative examples, when the electron transport layer or hole blocking layer is prepared using compounds in the embodiments of the present invention, the OLED device exhibits improved device voltage, device efficiency, and device lifetime. These performance improvements are attributed to the high glass transition temperature, suitable HOMO and LUMO energy levels, high T1 energy level, and high electron mobility of the compounds. Furthermore, the above embodiments also demonstrate that the functional layers prepared using the compounds of the present invention are particularly suitable for tandem blue light-emitting materials, and can significantly improve the overall performance of OLED devices.

[0173] The above description is merely for the purpose of enabling those skilled in the art to understand the technical solution of the present invention and is not intended to limit the present invention. Any modifications, equivalent substitutions, improvements, etc., made within the spirit and principles of the present invention should be included within the protection scope of the present invention.

Claims

1. A compound, characterized in that, The chemical structural formula of the compound is shown below: Among them, at least one of Z1-Z6 is N, and the rest are CH; L1, L2, and L3 are each independently one of a single bond, a substituted or unsubstituted C6-C30 arylene, or a substituted or unsubstituted C3-C30 heteroarylene; Ar1-Ar4 are each independently one of a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C3-C30 heteroaryl group, and at least one of Ar1-Ar4 has the following chemical structural formula a: Chemical structural formula a R1-R6 are each independently one of hydrogen, deuterium, fluorine, or C1-C10 alkyl groups; One of B1-B4 is the linking site, and the others are each independently one of hydrogen, deuterium, fluorine, methoxy, C1-C10 alkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C3-C30 heteroaryl. n is an integer between 0 and 4.

2. The compound according to claim 1, characterized in that, Two of L1, L2, and L3 are single bonds, and the remainder are substituted or unsubstituted C6-C30 arylene or substituted or unsubstituted C3-C30 heteroarylene. Alternatively, one of L1, L2, and L3 is a single bond, and the remaining two are independently substituted or unsubstituted C6-C30 arylene or substituted or unsubstituted C3-C30 heteroarylene. Alternatively, L1, L2, and L3 can each be independently a substituted or unsubstituted C6-C30 arylene or a substituted or unsubstituted C3-C30 heteroarylene.

3. The compound according to claim 2, characterized in that, The substituted or unsubstituted C6-C30 arylene and the substituted or unsubstituted C3-C30 heteroarylene include phenylene, biphenylene, naphthylene, fluorene, dibenzofuranyl, dibenzothiophene, phenanthrene, or benzonitrile. Optionally, when the C6-C30 arylene or the C3-C30 heteroarylene contains a substituent, the substituent includes deuterium.

4. The compound according to claim 1, characterized in that, At least one of Ar1-Ar4 has the chemical structural formula a; Alternatively, both Ar1 and Ar2 have the chemical structural formula a, and both Ar3 and Ar4 are substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C30 heteroaryl. Alternatively, Ar1 and Ar2 are both substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C30 heteroaryl, and both Ar3 and Ar4 are chemical structural formula a; Alternatively, one of Ar1 and Ar2 and one of Ar3 and Ar4 are chemical structures of formula a, and the remainder are substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C30 heteroaryl.

5. The compound according to claim 4, characterized in that, The substituted or unsubstituted C6-C30 aryl groups and the substituted or unsubstituted C3-C30 heteroaryl groups include phenyl, biphenyl, naphthyl, fluorenyl, dibenzofuranyl, dibenzothiophene, phenanthryl, or benzonitrile; Optionally, when the C6-C30 aryl or the C3-C30 heteroaryl contains a substituent, the substituent includes deuterium.

6. The use of the compound according to any one of claims 1-5 in organic electroluminescent devices, organic solar cells, organic thin-film transistors, organic photodetectors, organic field-effect transistors, organic integrated circuits, and organic photoreceptors.

7. An electronic functional layer material, characterized in that, The electronic functional layer material is an electron transport material or a hole blocking material, and the electronic functional layer material includes the compound according to any one of claims 1-5.

8. The electronic functional layer material according to claim 7, characterized in that, The electronic functional layer material is an electron transport material, and the electron transport material further includes a doping compound, wherein the mass percentage of the doping compound is less than or equal to 70 wt%. The doped compound is selected from at least one of the following: oxaoxazole compounds, thiazole compounds, triazole compounds, triazine compounds, triazabenzene compounds, oxalool compounds, diazanthracene compounds, silicon-containing heterocyclic compounds, quinoline compounds, phenanthroline compounds, metal chelates, fluorinated benzene compounds, and benzimidazole compounds; Optionally, the metal chelate is at least one of lithium hydroxyquinoline and its derivatives.

9. A light-emitting layer material, characterized in that, The light-emitting layer material includes a host material and a guest material, wherein the host material includes the compound according to any one of claims 1-5.

10. An organic electroluminescent device, characterized in that, The organic electroluminescent device includes: a first electrode, a second electrode, an electron transport functional layer, a light-emitting layer, and a hole transport functional layer stacked between the first electrode and the second electrode; At least one of the electron transport functional layer and the light-emitting layer comprises the compound according to any one of claims 1-5.

11. The organic electroluminescent device according to claim 10, characterized in that, The electron transport functional layer includes at least one of an electron injection layer, an electron transport layer, and a hole blocking layer, wherein at least one of the electron transport layer and the hole blocking layer includes the compound.

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