Compound with helical structure, electron transport material and application

Abstract

This application discloses a spirofluorene compound, an electron transport material, and its applications, belonging to the field of organic electroluminescence technology. The compound's structure is shown in general formula I. The compound incorporates a pentacyclic structure into the spirofluorene ring, which not only modulates the HOMO energy level of the molecule but also further increases the degree of molecular twist, thereby effectively reducing intermolecular interactions, lowering the evaporation temperature of the compound, and improving its heat resistance. Simultaneously, substituting triazine groups and azole substituents at different positions of the spirofluorene ring not only modulates the LUMO energy level of the molecule but also improves the compound's electron mobility, enhances carrier transport balance, improves device efficiency, and extends its lifespan.

Description

Technical Field

[0001] This application relates to the field of organic electroluminescence technology, and in particular to a compound with a helical structure, an electron transport material, and its applications. Background Technology

[0002] Organic light-emitting diodes (OLEDs), also known as organic light-emitting diodes, are widely used in display and lighting applications. OLEDs consist of a cathode, an anode, and a light-emitting functional layer located between the cathode and anode. This light-emitting functional layer includes an electron transport layer. The materials used in the electron transport layer are designed to transport electrons and require high electron mobility, energy level matching the light-emitting layer, good thermal stability, and excellent film-forming properties.

[0003] In related technologies, the electron mobility of the materials used in the electron transport layer is much lower than that of the hole mobility, which leads to an increase in nonradiative recombination of charge carriers. In addition, the materials have insufficient thermal stability and are prone to degradation and crystallization during use, which leads to the destruction of the film morphology and reduces the efficiency and lifespan of the device. Summary of the Invention

[0004] This application provides a compound with a helical structure, an electron transport material, and its application. The compound exhibits high electron mobility and heat resistance, which can improve device efficiency and lifespan. The technical solution is as follows: On the one hand, this application provides a compound having a spirostructure, the structure of which is shown in general formula I: ; Among them, R1 to R 14 At least one of them has the structure shown in Formula II or Formula III, and the remaining groups are each independently represented as hydrogen atom, deuterium atom, halogen, cyano, nitro, C1-C8 alkyl, C1-C12 alkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 aryl containing at least one heteroatom, substituted or unsubstituted C2-C8 alkenyl, substituted or unsubstituted C2-C8 alkynyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, triaromatic amino, substituted or unsubstituted carbazolyl, (9,9-dialkyl)fluorenyl, (9,9-disubstituted or unsubstituted aryl)fluorenyl, 9,9-spirofluorenyl, substituted or unsubstituted C6-C60 dibenzothiophene, substituted or unsubstituted C6-C60 dibenzofuranyl; A is selected from O, S, Se, NAr, or CR. 15 R 16 Among them, Ar and R 15 To R 20Each of the following is independently selected from C1-C12 alkyl, C1-C8 alkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 aryl containing at least one heteroatom, substituted or unsubstituted C2-C8 alkenyl, substituted or unsubstituted C2-C8 alkynyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; Ar1 and Ar2 are each independently represented as a substituted or unsubstituted C6~C30 aryl group, or a substituted or unsubstituted C3~C30 aryl group containing at least one heteroatom; Z1 to Z3 are each independently represented as N or CH, and at least one of Z1 to Z3 is N; L represents a substituted or unsubstituted C6-C30 aryl group.

[0005] In one possible implementation, Ar1 and Ar2 are each independently represented as a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group: phenyl, deuterated phenyl, tolyl, naphthyl, phenanthryl, anthracene, perylyl, fluoranthyl, pyrene, phenylnaphthyl, naphthylphenyl, terphenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9,9-spirodifluorenyl, benzofuran. yl, benzothiophene, dibenzofuran, dibenzothiophene, benzophenanthrene, spiro[fluorene-9,9'-oxazonium], pyridyl, benzylnitrile, benzylnitrilephenyl, pyridylphenyl, indolyl, carbazoleindolyl, fluorenecarbazole, imidazolyl, oxazolyl, thiazolyl, thiadiazolyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, azadibenzofuran, azadibenzothiophene.

[0006] In another possible implementation, when the aryl or heteroaryl group is substituted, the substituent is a C1-C12 alkyl group.

[0007] In another possible implementation, L is selected from phenylene or biphenylene.

[0008] In another possible implementation, R1 to R 14 When at least one of the components has the structure shown in Formula III, the structure of the compound is as shown in general formulas I-1 to I-24:

[0009]

[0010]

[0011]

[0012]

[0013]

[0014] .

[0015] On the other hand, this application provides an electron transport material comprising any of the compounds described above.

[0016] In one possible implementation, the compound has a mass percentage of 100%.

[0017] In another possible implementation, the electron transport material further includes: a doped compound; The mass percentage of the doped compound is not greater than 70%, and the mass percentage of the compound is not less than 30%.

[0018] In another possible implementation, the doped compound is selected from at least one of 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.

[0019] On the other hand, this application provides an organic electroluminescent device, which includes an anode, a hole transport unit, a light-emitting layer, an electron transport unit, and a cathode arranged in sequence. The electronic transmission unit includes any of the electronic transmission materials described above.

[0020] In one possible implementation, the electron transport unit includes at least one of a hole blocking layer, an electron transport layer, and an electron injection layer; At least one of the hole blocking layer, the electron transport layer, and the electron injection layer includes the electron transport material.

[0021] In another possible implementation, the hole transport unit includes at least one of a hole injection layer, a hole transport layer, and an electron blocking layer.

[0022] On the other hand, this application provides a display device, which includes the organic electroluminescent device described in any of the above claims.

[0023] This application provides a compound with a spirofluorene structure, which incorporates a pentacyclic structure into the spirofluorene ring. This not only modulates the HOMO energy level of the molecule but also further increases the degree of molecular twist, thereby effectively reducing intermolecular interactions, lowering the evaporation temperature of the compound, and improving its heat resistance. Furthermore, substituting triazine groups and azole substituents at different positions of the spirofluorene ring not only modulates the LUMO energy level but also improves the electron mobility of the compound, enhances carrier transport balance, improves device efficiency, and extends lifespan. Attached Figure Description

[0024] Figure 1 This is a schematic diagram of the structure of an organic electroluminescent device provided in an embodiment of this application.

[0025] The reference numerals in the attached figures represent: 110 - Glass substrate, 120 - Anode, 130 - Hole injection layer, 140 - Hole transport layer, 150 - Electron blocking layer 160 - Emissive layer, 170 - Hole blocking layer, 180 - Electron transport layer, 190 - Electron injection layer, 200 - Cathode 210-Optical extraction layer. Detailed Implementation

[0026] To make the technical solution and advantages of this application clearer, the embodiments of this application will be described in further detail below.

[0027] The terms "first," "second," "third," and "fourth," etc., used in the specification, claims, and accompanying drawings of this application are used to distinguish different objects, not to describe a specific order. Furthermore, the terms "comprising" and "having," and any variations thereof, are intended to cover non-exclusive inclusion. For example, a process, method, system, product, or apparatus that includes a series of steps or units is not limited to the listed steps or units, but may optionally include steps or units not listed, or may optionally include other steps or units inherent to these processes, methods, products, or apparatuses.

[0028] The technical features described in this application in an open-ended manner include both closed technical solutions consisting of the listed features and open technical solutions that include the listed features.

[0029] This application involves numerical ranges. Unless otherwise specified, the numerical ranges mentioned above are considered continuous and include the maximum and minimum values ​​of the range, as well as every value between the maximum and minimum values. Furthermore, when the range refers to integers, it includes every integer between the maximum and minimum values ​​of the range. In addition, when multiple ranges are provided to describe features or characteristics, the ranges may be merged. In other words, unless otherwise specified, all ranges disclosed in this application should be understood to include any and all subranges included therein.

[0030] Unless otherwise specified, all percentage concentrations mentioned in this application refer to final concentrations. A final concentration indicates the percentage of the added component in the system after its addition.

[0031] Unless otherwise specified, the temperature parameters in this application allow for isothermal processing or processing within a certain temperature range. Isothermal processing allows temperature fluctuations within the precision range controlled by the instrument. Room temperature in this application generally refers to 4℃~30℃, and optionally, room temperature refers to 15℃~25℃.

[0032] On one hand, embodiments of this application provide a compound having a spirostructure, the structure of which is shown in general formula I: ; Among them, R1 to R 14 At least one of them has the structure shown in Formula II or Formula III, and the remaining groups are each independently represented as a hydrogen atom, a deuterium atom, a halogen, a cyano group, a nitro group, a C1-C8 alkyl group, a C1-C12 alkoxy group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 aryl group containing at least one heteroatom, a substituted or unsubstituted C2-C8 alkenyl group, a substituted or unsubstituted C2-C8 alkynyl group, etc. Substituted or unsubstituted C6~C60 aryl, substituted or unsubstituted C3~C60 heteroaryl, triaromatic (C6~C60)amino, substituted or unsubstituted carbazolyl (C6~C30), (9,9-dialkyl)fluorenyl, (9,9-disubstituted or unsubstituted aryl)fluorenyl, 9,9-spirofluorenyl, substituted or unsubstituted C6~C60 dibenzothiophene, substituted or unsubstituted C6~C60 dibenzofuranyl; A is selected from O, S, Se, NAr, or CR. 15 R 16 Among them, Ar and R 15 To R 20Each of the following is independently selected from C1-C12 alkyl, C1-C8 alkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 aryl containing at least one heteroatom, substituted or unsubstituted C2-C8 alkenyl, substituted or unsubstituted C2-C8 alkynyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; Ar1 and Ar2 are each independently represented as a substituted or unsubstituted C6~C30 aryl group, or a substituted or unsubstituted C3~C30 aryl group containing at least one heteroatom; Z1 to Z3 are each independently represented as N or CH, and at least one of Z1 to Z3 is N; L represents a substituted or unsubstituted C6-C30 aryl group.

[0033] This application provides a compound with a spiro structure containing a pentacyclic spirofluorene structure. The introduction of the spirofluorene structure can effectively reduce intermolecular interactions, significantly lower the evaporation temperature of the compound, and thus improve its heat resistance. Simultaneously, the compound also exhibits significantly improved electron mobility, which can enhance carrier transport balance, thereby improving device efficiency and lifetime.

[0034] In one possible implementation, Ar1 and Ar2 are each independently represented as a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group: phenyl, deuterated phenyl, tolyl, naphthyl, phenanthryl, anthracene, perylyl, fluoranthyl, pyrene, phenylnaphthyl, naphthylphenyl, terphenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9,9-spirodifluorenyl, benzofuran. yl, benzothiophene, dibenzofuran, dibenzothiophene, benzophenanthrene, spiro[fluorene-9,9'-oxazonium], pyridyl, benzylnitrile, benzylnitrilephenyl, pyridylphenyl, indolyl, carbazoleindolyl, fluorenecarbazole, imidazolyl, oxazolyl, thiazolyl, thiadiazolyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, azadibenzofuran, azadibenzothiophene.

[0035] In the embodiments of this application, Ar1 and Ar2 are each independently represented by the aforementioned substituted or unsubstituted aryl and heteroaryl groups, which helps to improve the electron affinity of the compound, reduce the electron injection barrier, and enhance electron transport capability. Furthermore, groups such as naphthyl, phenanthryl, anthracene, and perylene are beneficial for expanding the π-conjugated system, facilitating electron delocalization, and improving electron mobility. Additionally, groups such as 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9,9-spirodifluorenyl, and spiro[fluoren-9,9'-oxazanthracene] have rigid three-dimensional structures, which help to provide steric hindrance, increase the glass transition temperature of the compound, and thus improve its thermal stability. Moreover, groups such as dibenzofuranyl, dibenzothiopheneyl, and carbazoleyl are high triplet energy level groups, which help to prevent exciton quenching and protect the exciton energy of the luminescent layer.

[0036] When the above-mentioned aryl or heteroaryl groups are substituted, the substituents can be C1 to C12 alkyl groups.

[0037] In the embodiments of this application, the C1-C8 alkyl and C1-C12 alkyl groups mentioned above can be selected from methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, etc.; The aryl groups of C6~C30 and C6~C60 can be selected from phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, fentanyl, fluorene, pyrene, perylene, azulene, etc. The C2~C8 alkenyl groups can be selected from vinyl, propenyl, butenyl, etc.; The C2~C8 alkyl group can be selected from ethynyl, propynyl, butynyl, etc.; The C3-C60 heteroaryl group can be selected from dibenzothiophene, dibenzofuran, dibenzoselenene, furan, thiophene, benzofuran, benzothiophene, benzoselenene, carbazole, indolocarbazole, pyridinylindole, pyrrolodipyridine, pyrazole, imidazole, triazole. Oxazole, thiazole, oxadiazole, oxtriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxthiazine, oxadiazine, indole, benzimidazole, indazole, inoxazine, benzoxazole, benziisoxazole, benzothiazazole, quinoline, isoquinoline, cinnamoline, quinazoline, quinoxaline, naphthidine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenothiazine, benzofuran-pyridine, furan-dipyridine, benzothiophene-pyridine, thiophene-dipyridine, benzoselenophene-pyridine, selenophene-dipyridine, etc. Optionally, the heteroaryl group of C3 to C60 is selected from dibenzothiophene, dibenzofuran, dibenzoselenene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azaborane, 1,3-azaborane, 1,4-azaborane, boronazynylene and their aza analogs.

[0038] An aryl group with C3 to C30 and containing at least one heteroatom can be selected from furan, thiophene, selenophene, benzofuran, benzothiophene, benzoselenophene, dibenzofuran, dibenzothiophene, dibenzoselenophene, pyridine, pyrazine, pyridazine, pyrimidine, 1,3,5-triazine, etc.

[0039] The C6~C60 dibenzothiophene group can be selected from 1-dibenzothiophene, 2-dibenzothiophene, 3-dibenzothiophene, 4-dibenzothiophene, etc.

[0040] The C6~C60 dibenzofuran group can be selected from 1-dibenzofuran, 2-dibenzofuran, 3-dibenzofuran, 4-dibenzofuran, etc.

[0041] The C6~C30 arylene groups can be selected from phenylene, biphenylene, naphthylene, phenanthrene, anthracene, pyridylene, pyrimidinylene, dibenzofuranylene, dibenzothiophene, etc.

[0042] In one possible implementation, L is selected from phenylene or biphenylene.

[0043] In the embodiments of this application, both phenylene and biphenylene exhibit good thermal stability. L, as a bridging group connecting the spirostructure and the functional groups Ar1 / Ar2, helps improve the heat resistance of the compound when selected from phenylene or biphenylene. Furthermore, phenylene and biphenylene are excellent charge transport units, contributing to the provision of rapid electron transport pathways.

[0044] In one possible implementation, R1 to R 14 When at least one of the components has the structure shown in Formula III, the structures of the above compounds are shown in general formulas I-1 to I-24:

[0045]

[0046]

[0047]

[0048]

[0049] .

[0050] In the embodiments of this application, O has a strong electron-withdrawing effect, which can significantly reduce the LUMO energy level and greatly improve the electron injection efficiency; S can enhance spin-orbit coupling and improve exciton utilization; NAr can provide p-type doping sites, form bipolar transport, balance the charge recombination region, and suppress exciton quenching. Therefore, when A is selected from O, S, and NAr, it helps to improve device performance.

[0051] Examples of compounds with helical structures in the embodiments of this application are shown in Table 1.

[0052]

[0053]

[0054] On the other hand, embodiments of this application provide an electronic transport material, which includes any of the compounds mentioned above.

[0055] The electron transport material provided in this application embodiment has all the advantages of the above-mentioned compounds.

[0056] In one possible implementation, the electron transport material comprises only the compound, in which case the mass percentage of the compound is 100%.

[0057] In the embodiments of this application, the aforementioned electron transport material can be used in either an electron transport layer or a hole blocking layer. That is, when the electron transport material is used in an electron transport layer, only the aforementioned compounds with helical structures can be used. Similarly, when the electron transport material is used in a hole blocking layer, only the aforementioned compounds with helical structures can be used.

[0058] In another possible implementation, the electron transport material further includes: a doped compound; The mass percentage of the doped compound is not greater than 70%, and the mass percentage of the compound is not less than 30%.

[0059] In this implementation, the mass percentage of the doped compound can be 1% to 70%, and correspondingly, the mass percentage of the compound can be 30% to 99%.

[0060] For example, the mass percentage of the doped compound includes, but is not limited to, one or any two of the following values ​​in a range: 1%, 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. Optionally, the mass percentage of the doped compound can be 20% to 70%.

[0061] The mass percentage of this compound includes, but is not limited to, one or any two of the following values ​​within a range: 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. Optionally, the mass percentage of this compound can be between 30% and 80%.

[0062] In the embodiments of this application, when the electron transport material is used in the electron transport layer, the doping compound may be 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.

[0063] The metal chelate can be selected from at least one of lithium hydroxyquinoline and its derivatives. Specifically, lithium hydroxyquinoline can be 8-hydroxyquinoline lithium.

[0064] When electron transport materials are used in hole blocking layers, the doping compound can be selected from at least one of oxaoxazole compounds, thiazole compounds, triazole compounds, and triazine compounds.

[0065] In the embodiments of this application, the doped compound has suitable electron affinity and excellent electron transport characteristics. By compounding the doped compound with the compound having a helical structure, the doped compound and the compound having a helical structure work synergistically, which is beneficial to further improve the electron injection efficiency and transport rate, thereby reducing the operating voltage of the OLED device and improving the luminous efficiency of the device.

[0066] In the embodiments of this application, when the electron transport material of any of the above implementations is used in the electron transport layer, the OLED device can possess both high luminous efficiency, low operating voltage, and strong thermal stability. When used in the hole blocking layer, it can effectively block holes from entering the electron transport layer, increase electron recombination in the light-emitting layer, and improve the luminous efficiency of the device.

[0067] On the other hand, embodiments of this application provide a light-emitting layer material, which includes any of the compounds mentioned above.

[0068] The light-emitting layer material provided in this application embodiment possesses all the advantages of the aforementioned compounds. When this light-emitting layer material is applied to the light-emitting layer, 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 the OLED device.

[0069] In one possible implementation, the luminescent layer material comprises a host material and a guest material, wherein the host material comprises the compound.

[0070] The guest material can be any of the guest materials currently used in OLED devices, and the selection can be made adaptively according to the actual light emission requirements, without any specific restrictions.

[0071] In one possible implementation, the host material also includes a host compound, which has a mass percentage of 1% to 20%.

[0072] For example, the mass percentage of the main compound includes, but is not limited to, any one of the following values ​​or a range of any two values: 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 19%, 20%, etc.

[0073] Accordingly, the mass percentage of the compound with a helical structure in the main material is 80% to 99%. For example, the mass percentage of the compound includes, but is not limited to, any one of the following values ​​or a range consisting of any two of the following values: 80%, 81%, 82%, 83%, 84%, 85%, 86%, 87%, 88%, 89%, 90%, 91%, 92%, 93%, 94%, 95%, 96%, 97%, 98%, 99%, etc.

[0074] In the embodiments of this application, the main compound may be selected from at least one of 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.

[0075] For example, the 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. The organometallic phosphorescent complexes may contain elements such as Ir, Pt, Os, Cu, or Au.

[0076] In this embodiment, the aforementioned host compound and a compound with a helical structure are used as the host material. This allows the host compound and the helical compound to work synergistically, ensuring the luminous efficiency of the OLED device while also optimizing charge transport balance, reducing non-radiative losses, and improving device stability. Furthermore, it facilitates the control of exciton distribution in the emissive layer, suppresses exciton quenching, and broadens the luminous adaptability. In addition, the helical compound is suitable for tandem blue light-emitting materials, significantly improving the overall performance of the device.

[0077] On the other hand, embodiments of this application provide an organic electroluminescent device, which includes an anode, a hole transport unit, a light-emitting layer, an electron transport unit, and a cathode arranged in sequence. The light-emitting layer includes any of the light-emitting layer materials mentioned above; The electronic transmission unit includes any of the electronic transmission materials mentioned above.

[0078] The organic electroluminescent device provided in this application has all the advantages of the above-mentioned compounds. For example, the organic electroluminescent device has high luminous efficiency, low operating voltage, and strong thermal stability.

[0079] In one possible implementation, the electron transport unit includes at least one of a hole blocking layer, an electron transport layer, and an electron injection layer; At least one of the hole blocking layer, electron transport layer, and electron injection layer includes the electron transport material mentioned above.

[0080] For example, the electron transport unit includes an electron transport layer, and correspondingly, the anode, hole transport unit, light-emitting layer, electron transport layer, and cathode are stacked in sequence. The electron transport layer includes the electron transport material mentioned above.

[0081] For example, the electron transport unit includes an electron transport layer and an electron injection layer, and correspondingly, the anode, hole transport unit, light-emitting layer, electron transport layer, electron injection layer, and cathode are stacked in sequence. At least one of the electron transport layer and electron injection layer includes the aforementioned electron transport material.

[0082] For example, the electron transport unit includes an electron transport layer and a hole blocking layer. Correspondingly, the anode, hole transport unit, light-emitting layer, hole blocking layer, electron transport layer, and cathode are stacked in sequence. At least one of the electron transport layer and hole blocking layer includes the electron transport material mentioned above.

[0083] For example, the electron transport unit includes an electron transport layer, a hole blocking layer, and an electron injection layer. Correspondingly, the anode, hole transport unit, light-emitting layer, hole blocking layer, electron transport layer, electron injection layer, and cathode are stacked in sequence. At least one of the hole blocking layer, electron transport layer, and electron injection layer includes the aforementioned electron transport material.

[0084] In one possible implementation, the hole transport unit includes at least one of a hole injection layer, a hole transport layer, and an electron blocking layer.

[0085] For example, a hole transport unit includes a hole injection layer and a hole transport layer, and correspondingly, the anode, hole injection layer, hole transport layer, light-emitting layer, electron transport unit, and cathode are stacked in sequence.

[0086] For example, a hole transport unit includes a hole transport layer and an electron blocking layer. Correspondingly, the anode, hole transport layer, electron blocking layer, light-emitting layer, electron transport unit, and cathode are stacked in sequence.

[0087] For example, a hole transport unit includes a hole transport layer, an electron blocking layer, and a hole injection layer. Correspondingly, the anode, hole injection layer, hole transport layer, electron blocking layer, light-emitting layer, electron transport unit, and cathode are stacked in sequence.

[0088] In the embodiments of this application, the materials used for the hole transport layer and the electron blocking layer may be selected from at least one of carbazole compounds, triaromatic amine compounds, benzidine diamine compounds, fluorene compounds, phthalocyanine compounds, polythiophene, polyethylene, polybenzene sulfonic acid, quinone compounds, and hexacyanohexatribenzene.

[0089] For example, the materials used for the hole transport layer and the electron blocking layer are each independently selected from at least one of the following compounds:

[0090]

[0091]

[0092]

[0093]

[0094] .

[0095] The material used for the hole injection layer can be at least one of the following compounds: .

[0096] In one possible implementation, the total thickness of the light-emitting functional layer, which consists of hole transport units, a light-emitting layer, and electron transport units, is 1 nm to 1000 nm.

[0097] For example, the total thickness of the light-emitting functional layer includes, but is not limited to, any one of the following values ​​or a range consisting of any two of the following values: 1nm, 30nm, 50nm, 100nm, 150nm, 200nm, 300nm, 400nm, 500nm, 550nm, 600nm, 700nm, 750nm, 800nm, 850nm, 900nm, 950nm, and 1000nm.

[0098] Optionally, the total thickness of the light-emitting functional layer can be 50nm to 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.

[0099] It should be noted that the total thickness of the light-emitting functional layer and the thickness of each functional layer within the light-emitting functional layer can be adjusted according to actual needs, and no specific limitations are imposed on this.

[0100] In one possible implementation, the fabrication method for each functional layer in the light-emitting functional layer includes: vacuum evaporation, molecular beam evaporation, solvent-based dip coating, spin coating, rod coating, or inkjet printing. For the metal electrodes, they can be prepared by evaporation or sputtering.

[0101] In one possible implementation, the metal electrode of the organic electroluminescent device is prepared by either vapor deposition or sputtering.

[0102] In addition to organic electroluminescent devices, the organometallic complexes provided in this application can also be used in organic solar cells, organic thin-film transistors, organic photodetectors, organic field-effect transistors, organic integrated circuits, and organic photosensors.

[0103] On the other hand, embodiments of this application provide a display device that includes any of the organic electroluminescent devices mentioned above.

[0104] The display devices provided in this application have all the advantages of organic electroluminescent devices. Exemplary examples include, but are not limited to: OLED TVs, mobile phones, tablets, laptops, in-vehicle displays, MP3 players, smartwatches, fitness trackers, virtual reality (VR) headsets, augmented reality (AR) glasses, etc.

[0105] Exemplary embodiments of this application will now be described in more detail. While exemplary embodiments of this application are described below, it should be understood that this application may be implemented in various forms and should not be limited to the embodiments set forth herein.

[0106] It should be noted that the synthesis of the aforementioned compounds with spirostructures is not limited to the synthetic methods and raw materials used in this application. Those skilled in the art can also select other methods or routes to obtain the compounds with spirostructures proposed in this application. Compounds with spirostructures synthesized by those skilled in the art using other methods also fall within the scope of protection of this application.

[0107] The compounds, solvents, and reagents used in the synthesis methods not mentioned in this application are all commercially available raw material products that can be purchased from the domestic chemical market or prepared in-house using known methods.

[0108] The following synthesis examples involve the synthesis of compounds with spiro structures, and the synthesis of intermediate compounds (hereinafter referred to as intermediates) is also involved in the synthesis process. These compounds with spiro structures and intermediates are separated by column chromatography and characterized by elemental analysis and high-resolution mass spectrometry (1HRMS).

[0109] Synthesis example Step 1: Synthesis of intermediate C1

[0110] Raw material A1 (20.0 g, 70.69 mmol), raw material B1 (11.32 g, 63.59 mmol), and potassium carbonate (14.66 g, 106.07 mmol) were added to a three-necked flask, followed by toluene (200 mL), ethanol (100 mL), and deionized water (100 mL). Under nitrogen protection, Pd(PPh3)4 (1.0 g, 0.86 mmol) was added, and the mixture was refluxed and stirred for 10 h. After the reaction was completed, the liquid was separated, the organic phase was concentrated to dryness, and the crude product was separated by column chromatography using petroleum ether as the eluent to give 10.2 g of white solid, with a yield of 50%.

[0111] HRMS (ESI, m / z): [M+H] + Theoretical value: C 14 H 10 BrS, 288.9681, experimental value: 288.9678. Elemental analysis: theoretical value: C: 58.15; H: 3.14; Br: 27.63; S: 11.09; experimental value: C: 58.06; H: 3.18; Br: 27.58; S: 11.18.

[0112] Step 2: Synthesis of intermediate E1

[0113] Intermediate C1 (10.0 g, 34.58 mmol), anhydrous tetrahydrofuran (50 mL), magnesium shavings (0.84 g, 34.55 mmol), and one iodine grain were added to a three-necked flask. The mixture was heated to vigorous reflux under nitrogen protection to initiate the reaction. After the color of the iodine faded, the mixture was refluxed for another 3 hours until all the magnesium shavings disappeared. The starting material D1 (7.0 g, 27.02 mmol) was added in portions. After reacting for 2 hours, the reaction of the starting material D1 was complete. Most of the tetrahydrofuran was distilled off while hot. After cooling, dilute hydrochloric acid solution was added dropwise until the pH was weakly acidic. The reaction mixture was then extracted twice with dichloromethane. Combine the organic phases, concentrate to dryness, add glacial acetic acid (50 mL) and concentrated hydrochloric acid (5 mL), reflux for 5 h. After the reaction is complete, cool, concentrate the solvent to dryness, dissolve in dichloromethane, wash the organic phase with sodium bicarbonate aqueous solution until neutral, dry, and separate the organic phase by column chromatography using petroleum ether / dichloromethane (20 / 1, v / v) as eluent to give 8.5 g of white solid, yield 70%.

[0114] HRMS (ESI, m / z): [M+H] + Theoretical value: C 27 H 16 BrS, 451.0151, Experimental value: 451.0155. Elemental analysis: Theoretical values: C: 71.85; H: 3.35; Br: 17.70; S: 7.10; Experimental values: C: 71.89; H: 3.38; Br: 17.59; S: 7.13.

[0115] Step 3: Synthesis of intermediate G1

[0116] Intermediate E1 (8.0 g, 17.72 mmol), anhydrous potassium acetate (3.48 g, 35.46 mmol), starting material F1 (5.4 g, 21.26 mmol), and anhydrous toluene (80 mL) were added to a three-necked flask. Under nitrogen protection, 0.37 g, 0.53 mmol of diphenylphosphine palladium chloride was added. The mixture was refluxed for 8 h until the reaction was complete. The inorganic salts were filtered off, and the filtrate was evaporated to dryness. The crude product was separated by column chromatography using petroleum ether / dichloromethane (3 / 1, v / v) as the eluent to give 8.1 g of a white solid, with a yield of 92%.

[0117] HRMS (ESI, m / z): [M+H] + Theoretical value: C 33 H 28BO₂S, 499.1898, experimental value: 499.1895. Elemental analysis: Theoretical values: C: 79.52; H: 5.46; B: 2.17; O: 6.42; S: 6.43; Experimental values: C: 79.45; H: 5.49; B: 2.19; O: 6.48; S: 6.39.

[0118] Step 4: Synthesis of Compound 3

[0119] The starting material H1 (0.5 g, 1.87 mmol), intermediate G1 (0.97 g, 1.95 mmol), and potassium carbonate (0.39 g, 2.82 mmol) were added to a three-necked flask, followed by toluene (10 mL), dioxane (5 mL), and deionized water (5 mL). Under nitrogen protection, Pd(PPh3)4 (0.05 g, 0.043 mmol) was added, and the mixture was refluxed and stirred for 10 h. After the reaction was completed, the mixture was separated into liquid and liquid phases, concentrated to dry organic phase, and the crude product was separated by column chromatography using petroleum ether as the eluent to give 0.72 g of white solid, with a yield of 63%.

[0120] HRMS (ESI, m / z): [M+H] + Theoretical value: C 42 H 26 N3S, 604.1842; Experimental value: 604.1846. Elemental analysis: Theoretical values: C: 83.56; H: 4.17; N: 6.96; S: ​​5.31; Experimental values: C: 83.48; H: 4.21; N: 6.91; S: 5.40.

[0121] This application uses the same synthesis method as intermediate C1 to synthesize other intermediates, the difference being the different raw materials, which are shown in Table 2.

[0122]

[0123]

[0124] This application uses the same synthesis method as intermediate E1 to synthesize other intermediates, the difference being the different raw materials, which are shown in Table 3.

[0125]

[0126]

[0127] This application uses the same synthesis method as intermediate G1 to synthesize other intermediates, the difference being the different raw materials, which are shown in Table 4.

[0128]

[0129]

[0130] Synthesis of intermediate L1

[0131] Raw material J1 (5.0 g, 16.55 mmol), raw material K1 (3.68 g, 17.36 mmol), and potassium carbonate (3.43 g, 24.82 mmol) were added to a three-necked flask, followed by toluene (100 mL), dioxane (50 mL), and deionized water (50 mL). Under nitrogen protection, Pd(PPh3)4 (0.5 g, 0.43 mmol) was added, and the mixture was refluxed and stirred for 10 h. After the reaction was completed, the liquid was separated, the organic phase was concentrated to dryness, and the crude product was separated by column chromatography using petroleum ether / dichloromethane (10 / 1~5 / 1, v / v) as the eluent to give 6.2 g of white solid, with a yield of 86%.

[0132] HRMS (ESI, m / z): [M+H] + Theoretical value: C 27 H 17 ClN3O, 434.1055; Experimental value: 434.1058. Elemental analysis: Theoretical values: C: 74.74; H: 3.72; Cl: 8.17; N: 9.68; O: 3.69; Experimental values: C: 74.81; H: 3.68; Cl: 8.09; N: 9.76; O: 3.65.

[0133] This application uses the same synthesis method as intermediate L1 to synthesize other intermediates, the difference being the different raw materials, which are shown in Table 5.

[0134]

[0135]

[0136] This application uses the same synthetic method as compound 3 to synthesize other compounds, the difference being the different raw materials, which are shown in Table 6.

[0137]

[0138]

[0139] Based on the series of compounds synthesized above, this application systematically evaluates their physical properties and photoelectric performance. The relevant test items are as follows: (1) Triplet level (T1): using the Horiba Fluorolog 3 series fluorescence spectrometer, at 2×10 -5 Determined in mol / L toluene solution.

[0140] (2) Glass transition temperature (Tg): The temperature was tested using a differential scanning calorimeter Pyris Diamond (DSC2920) under a nitrogen atmosphere at a heating and cooling rate of 10℃ / min.

[0141] (3) HOMO level: obtained by the AC-2 ionization energy testing system under atmospheric conditions.

[0142] (4) LUMO level: derived from E LUMO =E HOMO +Eg was calculated, where the band gap Eg was measured using a Hitachi U2900 dual-beam UV-Vis spectrophotometer.

[0143] (5) Electron mobility: The compound synthesized in the example of this application was made into a single-electron device and the space charge confined current (SCLC) method was used to measure the electron mobility based on the single-electron device structure.

[0144] The single-electron device comprises a substrate / anode, a hole injection layer, an electron transport layer, an electron injection layer, and a cathode arranged in sequence, and its fabrication method is as follows: Substrate / Anode: The ITO (Indium Tin Oxide)-Ag-ITO (Indium Tin Oxide) glass substrate was cleaned twice in distilled water, ultrasonically cleaned for 30 minutes in a commercial cleaning agent, and then repeatedly cleaned twice with distilled water, ultrasonically cleaned for 10 minutes each time. After cleaning, it was ultrasonically cleaned sequentially with ethanol, acetone, and isopropanol (5 minutes each time), dried, and then transferred to a plasma cleaner for 5 minutes. It was then baked in a clean environment until all moisture was removed, cleaned with ultraviolet photosynthetic ozone, and then treated with oxygen plasma for 30 seconds. Finally, it was sent to the vacuum chamber of the vapor deposition machine and evacuated. Using this substrate as the anode, other functional layers were sequentially vapor-deposited on it.

[0145] Hole injection layer: LiQ (10nm) was deposited on ITO as a hole injection layer at a deposition rate of 0.1nm / s.

[0146] Electron transport layer: Compound 3: 50% LiQ (60nm) was deposited on the hole injection layer as an electron transport layer, wherein compound 3 is the electron transport material and the deposition rate is 0.05nm / s. 8-hydroxyquinoline lithium (LiQ) with a mass ratio of 50% was doped and the deposition rate was 0.05nm / s.

[0147] Electron injection layer: Yb (1 nm) is deposited on the electron transport layer as an electron injection layer at a deposition rate of 0.1 nm / s.

[0148] Cathode: Ag was deposited on the electron injection layer: 10% Mg (14nm) was used as the cathode, the deposition rate of Ag was 0.09nm / s, and the deposition rate of Mg was 0.01nm / s.

[0149] The electron mobility of various electron transport materials at a thickness of 60 nm is shown in Table 7, where the electron mobility is expressed in scientific notation. In the embodiments of this application, the numerical value aEb described in scientific notation is equivalent to a × 10⁻⁶. b For example, 1×10 4 It can be written as 1E4.

[0150] The test results for other test items are also shown in Table 7, which covers the highest occupied molecular orbital (HOMO) energy level, the lowest unoccupied molecular orbital (LUMO) energy level, the triplet excitation energy (T1), the glass transition temperature (Tg), and the electron mobility of the compound.

[0151]

[0152]

[0153] As can be seen from Table 7, the glass transition temperatures of the compounds provided in this application are all higher than 150℃, which is significantly better than that of conventional organic materials. This indicates that they have excellent phase stability and high temperature resistance after film formation, which is beneficial to extending the service life of OLED devices and improving luminous stability.

[0154] The compounds provided in this application generally have deep HOMO levels (-6.00 eV to -6.30 eV) and moderate LUMO levels, which can effectively reduce the carrier injection barrier, thereby reducing the driving voltage and improving device efficiency. Especially for hole blocking layer materials, the deeper HOMO levels can effectively suppress holes from crossing the light-emitting layer from the anode side, reduce leakage current, and increase the probability of electron-hole recombination in the light-emitting layer.

[0155] The compounds provided in this application all have triplet energy levels (T1) higher than 2.3 eV, with some even exceeding 2.5 eV. This characteristic is particularly important for blue phosphorescent OLEDs. High triplet energy levels can reduce the number of excitons leaving the emissive layer, effectively preventing excitons from diffusing back from the emissive layer to the transport layer, improving the efficiency of exciton conversion luminescence, ensuring the energy transfer efficiency between host and guest components, suppressing energy loss caused by non-radiative transitions, and thus improving the current efficiency and lifetime of the device.

[0156] The compounds provided in this application also have high electron mobility, which helps to improve device voltage, especially turn-on voltage and current efficiency.

[0157] The structure and performance of organic electroluminescent devices prepared using the compounds provided in this application will be further described in detail below through Examples 1-24 and Comparative Examples 1-4.

[0158] See the structure of organic electroluminescent devices. Figure 1 It includes a glass substrate 110, an anode 120, a hole injection layer 130, a hole transport layer 140, an electron blocking layer 150, a light-emitting layer 160, a hole blocking layer 170, an electron transport layer 180, an electron injection layer 190, a cathode 200, and a light extraction layer 210 arranged in sequence. The specific structure is: glass / anode (ITO) / hole injection layer (HIL) / hole transport layer (HTL) / electron blocking layer (EBL) / light-emitting layer (EML, main material: blue light-emitting material) / hole blocking layer (HBL) / electron transport layer (ETL, electron transport material: lithium 8-hydroxyquinoline) / electron injection layer (EIL) / cathode / light extraction layer (CPL).

[0159] Example 1 A transparent conductive ITO glass substrate 110 (with an anode 120) (China Southern Glass Holding 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.

[0160] Hole injection layer: Compound HT and p-dopant (mass ratio of 97:3, thickness of 10 nm) were vapor-deposited on ITO as hole injection layer 130 at a deposition rate of 0.1 nm / s.

[0161] Hole transport layer: Compound HT is deposited on the hole injection layer to form a 100 nm thick hole transport layer 140, with a deposition rate of 0.1 nm / s.

[0162] Electron blocking layer: EB was deposited by vapor deposition to form a 10 nm thick electron blocking layer 150. The deposition rate was 0.1 nm / s.

[0163] Light-emitting layer: A 30nm thick light-emitting layer 160 is deposited on the electron blocking layer, wherein BH is the main light-emitting material, and BD is used as the blue light-emitting material at a weight ratio of 3%, and the deposition rate is 0.1nm / s.

[0164] Hole blocking layer: Compound HB-1 is deposited on the light-emitting layer to form a 5 nm thick hole blocking layer 170, with a deposition rate of 0.1 nm / s.

[0165] Electron transport layer: Compound 3:LiQ (weight ratio 5:5) with a thickness of 35 nm was deposited as electron transport layer 180. LiQ is lithium 8-hydroxyquinoline, and the deposition rate was 0.1 nm / s.

[0166] Electron injection layer: A 1nm thick LiQ layer is deposited as the electron injection layer 190.

[0167] Cathode: A 15nm Mg:Ag electrode layer is deposited by vapor deposition, with a Mg to Ag mass ratio of 1:9 as the device cathode 200.

[0168] Light extraction layer: An 80nm CPL is vacuum-deposited on the cathode layer 200 as the light extraction layer 210.

[0169] The methods for preparing organic electroluminescent devices in Examples 2-24 and Comparative Examples 1-4 can be found in Example 1, and will not be repeated here. The difference is that the materials used for the electron transport layer and the hole blocking layer are different, as shown in Table 8.

[0170] The materials used for the remaining layers are shown below:

[0171]

[0172]

[0173]

[0174]

[0175]

[0176] .

[0177]

[0178]

[0179]

[0180] The devices prepared in Examples 1-24 and Comparative Examples 1-4 were subjected to performance tests. The device performance was tested using a Photo Research PR655 spectrometer, and the results were measured at 1000 cd / cm². 2 Operating voltage, on-time voltage @1 nit, current efficiency (Index), and color coordinates at various brightness levels were measured. Room temperature and high temperature lifespan tests were conducted using a Jinghe D3000-96CH lifespan meter, measured at 20 mA / cm². 2 The time (LT95) for the brightness to become 95% of the initial brightness in environments with normal temperature (27℃) and high temperature (85℃) under current density is shown in Table 9.

[0181]

[0182]

[0183] As can be seen from Table 9, the overall performance of the devices prepared in Examples 1-24 is significantly better than that of Comparative Examples 1-4, mainly in the following aspects: First, the driving voltage, i.e., the operating voltage, of the devices prepared in Examples 1-24 is between 3.42V and 3.59V, all lower than 3.60V, while the driving voltage of the devices prepared in Comparative Examples 1-4 is as high as 3.72V to 3.90V. It is evident that the devices prepared in Examples 1-24 have lower driving voltages.

[0184] Furthermore, the turn-on voltages of the devices prepared in Examples 1-24 are generally between 2.61V and 2.80V, while the turn-on voltages of the devices prepared in Comparative Examples 1-4 are between 2.93V and 3.09V. This indicates that the devices prepared in Examples 1-24 also have relatively low turn-on voltages.

[0185] This demonstrates that the devices prepared from the compounds provided in this application have lower driving voltage and turn-on voltage, which can significantly improve device energy efficiency and reduce device power consumption.

[0186] Secondly, the current efficiencies (Index column, unit: cd / A) of the devices prepared in Examples 1-24 are all in the range of 220.18-239.59, while the current efficiencies of the devices prepared in Comparative Examples 1-4 are in the range of 187.72-200.14. This shows that the current efficiencies of the devices prepared in Examples 1-24 are significantly higher than those in Comparative Examples 1-4. This demonstrates that the devices prepared from the compounds provided in this application have higher luminous efficiency and more efficient energy conversion, making them suitable for high-brightness, low-power display and lighting applications.

[0187] Secondly, regarding the lifetime at room temperature (LT95): the devices prepared in Examples 1-24 all had a lifetime of ≥233 hours, most of which exceeded 245 hours, with the highest reaching 264 hours. In contrast, the devices prepared in Comparative Examples 1-4 had a lifetime in the range of 187-201 hours, which was significantly lower than that of Examples 1-24.

[0188] Regarding the 85℃ high-temperature lifetime (LT95): the devices prepared in Examples 1-24 all had a high-temperature lifetime of ≥167 hours, with most ranging from 175 hours to 183 hours. In contrast, the devices prepared in Comparative Examples 1-4 only had a lifetime of 107 hours to 124 hours, showing a significant difference.

[0189] Compared to ET-1, ET-2, ET-4, HB-1, HB-2, HB-3, and HB-4, the spirostructure of the compound in this application has a larger conjugated system, which can increase the charge mobility of the molecule and improve device performance. Compared to ET-3, although it also introduces an indole group, the connection method is different. The spirostructure of ET-3 introduces a phenyl group through the nitrogen atom of the indole, which causes distortion and has poor stability.

[0190] This demonstrates that the compounds provided in this application can significantly improve the thermal stability and long-term operational reliability of devices, with particularly prominent advantages in high-temperature environments.

[0191] Analysis suggests that the improved performance is attributable to the following key characteristics of the compound provided in this application: (1) Suitable HOMO / LUMO energy levels: are beneficial for achieving good carrier injection and balance; (2) High triplet energy level (T1 > 2.3 eV): effectively restricts exciton diffusion and improves energy utilization efficiency; (3) High glass transition temperature (Tg > 150℃): Ensures the thermal stability of the thin film and extends the device life; (4) Excellent electron mobility (~10) -5 cm 2 / (V·s): Promotes electron transport, reduces voltage, and improves efficiency.

[0192] In summary, the compounds provided in this application possess the aforementioned characteristics, and these characteristics work synergistically to enable the compounds provided in this application to exhibit excellent performance in OLED devices, including lower operating voltage, higher current efficiency and external quantum efficiency, and longer lifespan, achieving comprehensive optimization.

[0193] The above description is only for the purpose of enabling those skilled in the art to understand the technical solution of this application, and is not intended to limit this application. Any modifications, equivalent substitutions, improvements, etc., made within the spirit and principles of this application should be included within the protection scope of this application.

Claims

1. A compound having a spirostructure, characterized in that, The structure of the compound is shown in general formula I: ； Among them, R1 to R 14 At least one of them has the structure shown in Formula II or Formula III, and the remaining groups are each independently represented as hydrogen atom, deuterium atom, halogen, cyano, nitro, C1-C8 alkyl, C1-C12 alkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 aryl containing at least one heteroatom, substituted or unsubstituted C2-C8 alkenyl, substituted or unsubstituted C2-C8 alkynyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, triaromaticamine, substituted or unsubstituted carbazolyl, (9,9-dialkyl)fluorenyl, (9,9-disubstituted or unsubstituted aryl)fluorenyl, 9,9-spirofluorenyl, substituted or unsubstituted C6-C60 dibenzothiophene, substituted or unsubstituted C6-C60 dibenzofuranyl; A is selected from O, S, Se, NAr, or CR. 15 R 16 Among them, Ar and R 15 To R 20 Each of the following is independently selected from C1-C12 alkyl, C1-C8 alkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 aryl containing at least one heteroatom, substituted or unsubstituted C2-C8 alkenyl, substituted or unsubstituted C2-C8 alkynyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; Ar1 and Ar2 are each independently represented as a substituted or unsubstituted C6~C30 aryl group, or a substituted or unsubstituted C3~C30 aryl group containing at least one heteroatom; Z1 to Z3 are each independently represented as N or CH, and at least one of Z1 to Z3 is N; L represents a substituted or unsubstituted C6-C30 aryl group.

2. The compound according to claim 1, characterized in that, Ar1 and Ar2 are each independently represented by the following substituted or unsubstituted aryl groups, substituted or unsubstituted heteroaryl groups: phenyl, deuterated phenyl, tolyl, naphthyl, phenanthryl, anthracel, perylyl, fluoranthyl, pyrel, phenylnaphthyl, naphthylphenyl, terphenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9,9-spirodifluorenyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, spiro[fluorene-9,9'-oxazanthene], pyridyl, benzylnitrile, benzylnitrile phenyl, pyridylphenyl, indolyl, carbazolylindolyl, fluorenylcarbazolyl, imidazolyl, oxazolyl, thiazolyl, thiadiazolyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl, azadibenzofuranyl, azadibenzothiopheneyl.

3. The compound according to claim 2, characterized in that, When the aryl or heteroaryl group is substituted, the substituent is a C1-C12 alkyl group.

4. The compound according to claim 1, characterized in that, L is selected from phenylene or biphenylene.

5. The compound according to any one of claims 1 to 4, characterized in that, The structures of the compounds are shown in general formulas I-1 to I-24: 。 6. An electron transport material, characterized in that, The electron transport material includes the compound according to any one of claims 1 to 5.

7. The electron transport material according to claim 6, characterized in that, The compound has a mass percentage of 100%.

8. The electron transport material according to claim 6, characterized in that, The electron transport material further includes: a doped compound; The mass percentage of the doped compound is not greater than 70%, and the mass percentage of the compound is not less than 30%.

9. The electron transport material according to claim 8, characterized in that, 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.

10. An organic electroluminescent device, characterized in that, The organic electroluminescent device includes an anode, a hole transport unit, a light-emitting layer, an electron transport unit, and a cathode arranged in sequence. The electronic transmission unit comprises the electronic transmission material as described in any one of claims 6 to 9.

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

12. The organic electroluminescent device according to claim 10, characterized in that, The hole transport unit includes at least one of a hole injection layer, a hole transport layer, and an electron blocking layer.

13. A display device, characterized in that, The display device includes the organic electroluminescent device according to any one of claims 10 to 12.

Images