Benzopentacyclic compound and application thereof

Abstract

The invention discloses a benzo pentacyclic compound and application thereof, and belongs to the technical field of display. The chemical structural formula of the compound is shown in the specification, wherein Ar, R1 to R6 are respectively and independently hydrogen, deuterium, halogen, cyano, nitro, alkyl of C1-C18, alkoxy of C1-C12, substituted or unsubstituted aryl of C6-C30 or substituted or unsubstituted heteroaryl of C3-C30, and R1 to R6 are respectively and independently selected from hydrogen, deuterium, halogen, cyano, nitro, alkyl of C1-C18, alkoxy of C1-C12, substituted or unsubstituted aryl of C6-C30 or substituted or unsubstituted heteroaryl of C3-C30; ar1 and Ar2 are respectively and independently a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C3-C30 heteroaryl group; each of L1 to L3 independently represents a single bond, a substituted or unsubstituted C6-C60 arylene group, or a substituted or unsubstituted C3-C30 heteroarylene group; at least one of Z1 to Z3 is N, and the balance is CH; a is O, S, Se or CR7R8. The compound has excellent electron transmission performance, and is beneficial to improving the voltage, efficiency and service life of a device.

Description

Technical Field

[0001] This invention relates to the field of display technology, and in particular to compounds containing benzopentane 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, an OLED device includes a cathode, an anode, and an electron transport layer, an emissive layer, and a hole transport layer stacked between the cathode and the anode. The electron transport layer is fabricated using electron transport materials.

[0004] Currently, there is still a need to improve the electron mobility and thermal stability of electron transport materials in order to further improve the voltage, efficiency and cycle life of OLED devices. Summary of the Invention

[0005] In view of this, the present invention provides a benzopentane-containing compound and its application, which can solve the technical problems existing in related technologies. Specifically, it includes the following technical solutions: In a first aspect, a benzopentane-containing compound is provided, the chemical structural formula of which is shown below: ; Ar, R1 to R6 are each independently one of hydrogen, deuterium, halogen, cyano, nitro, C1 to C18 alkyl, C1 to C12 alkoxy, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C3 to C30 heteroaryl. Ar1 and Ar2 are each independently one of a substituted or unsubstituted C6~C30 aryl group or a substituted or unsubstituted C3~C30 heteroaryl group; L1 to L3 are each independently one of a single bond, a substituted or unsubstituted C6~C60 arylene, or a substituted or unsubstituted C3~C30 heteroarylene; At least one of Z1 to Z3 is N, and the rest are CH; A is one of O, S, Se, CR7R8, and R7 and R8 are each independently one of C1~C12 alkyl, C1~C8 alkoxy, substituted or unsubstituted C2~C8 enyl, substituted or unsubstituted C2~C8 alkynyl, substituted or unsubstituted C6~C60 aryl, or substituted or unsubstituted C3~C60 heteroaryl.

[0006] In some possible implementations, Ar is selected from one of cyano, triazine, spirofluorene, or nitrogen-containing heteroaryl groups.

[0007] In some possible implementations, the chemical structural formula of the spirofluorene group is shown below: ; The chemical structural formula of the triazine group is shown below: ; The chemical structural formula of the nitrogen-containing heteroaryl group is shown below: ; Ar3 to Ar6 are each independently one of substituted or unsubstituted C6~C30 arylene or substituted or unsubstituted C3~C30 heteroarylene; L4 to L5 are each independently represented by a single bond, O, S, Se, and CR9R. 10 one of; B represents O, S, Se, NR. 11 ; At least one of Z4 to Z6 is N, and the rest are CH; Z7 to Z 10 Each is independently N or CR 12 ; Ar7 to Ar9, R9 to R 12 Each of them independently consists of one of hydrogen, deuterium, halogen, cyano, nitro, C1-C18 alkyl, C1-C12 alkoxy, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C3-C30 heteroaryl.

[0008] In some possible implementations, L1 to L3 are each independently one of a single bond, phenylene, biphenylene, cyanobiphenyl, benzonitrile, phenylnaphthyl, phenylanthryl, spiro[cyclopentane-1,9'-fluorene]yl, 9,9-dimethylfluoreneyl, and phenyl-9,9-dimethylfluoreneyl.

[0009] In some possible implementations, two of Z1 to Z3 are N, and the other is CH; Alternatively, Z1 to Z3 are all N.

[0010] In some possible implementations, R1 to R2 are each independently one of hydrogen, deuterium, and methyl. R3 to R6 are each independently one of hydrogen, deuterium, cyano, phenyl, benzonitrile, or pyridinyl.

[0011] In some possible implementations, Ar1 and Ar2 are each independently one of phenyl, biphenyl, cyanobiphenyl, adamantylphenyl, pyridylphenyl, dibenzofuranyl, benzonitrile, dibenzothiophene, 9,9-dimethylfluorenyl, and phenanthrene.

[0012] Secondly, the invention provides an application of a benzopentane-containing compound in organic electroluminescent devices, organic solar cells, organic thin-film transistors, organic photodetectors, organic field-effect transistors, organic integrated circuits, and organic photosensors.

[0013] Thirdly, an electron transport material is provided, the electron transport material comprising any of the benzopentane-containing compounds involved in the first aspect of the present invention.

[0014] In some possible implementations, the electron transport material further includes a dopant compound, wherein the mass percentage of the dopant 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.

[0015] Fourthly, a light-emitting layer material is provided, the light-emitting layer material comprising a host material and a guest material, wherein the host material comprises any of the benzopentane-containing compounds involved in the first aspect of the present invention.

[0016] In some possible implementations, the host material further includes a luminescent host compound, wherein the luminescent host compound comprises 1% to 20% by mass. The luminescent host compound is selected from at least one of the following: naphthalene compounds, pyrene compounds, fluorene compounds, phenanthrene compounds, chrysopraseene 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.

[0017] Fifthly, 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 any benzopentane-containing compound involved in the first aspect of the present invention.

[0018] 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 benzopentane-containing compound.

[0019] In a sixth aspect, a display device is provided, characterized in that the display device includes the organic electroluminescent device according to the fifth aspect of the present invention.

[0020] The benzopentacyclic compounds provided in this invention are triazine-based nitrogen-containing six-membered heterocycles and benzopentacyclic rings formed through specific sites. The introduction of the benzopentacyclic ring effectively reduces intermolecular interactions, significantly lowering the deposition temperature of the compound and thus improving its heat resistance. Furthermore, the introduction of the benzopentacyclic ring facilitates the formation of amorphous films, which is beneficial for improving device lifetime. In addition, the introduction of the nitrogen-containing six-membered heterocycle effectively modulates the HOMO and LUMO energy levels of the compound and enhances its electron mobility, helping to reduce the operating voltage of the device. Attached Figure Description

[0021] Figure 1 This is a schematic diagram of the structure of an organic electroluminescent device provided in an embodiment of the present invention.

[0022] 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 - Photoextraction layer. Detailed Implementation

[0023] 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.

[0024] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention pertains. The terminology used in this specification is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention.

[0025] In this article, "one or more" refers to any one, two or more of the listed items.

[0026] In this embodiment of the invention, terms such as "first aspect," "second aspect," "third aspect," and "fourth aspect" are used for descriptive purposes only and should not be construed as indicating or implying relative importance or quantity, nor should they be construed as implicitly indicating the importance or quantity of the indicated technical features. Moreover, terms such as "first," "second," "third," and "fourth" serve only as a non-exhaustive enumeration and should be understood not to constitute a closed limitation on the quantity.

[0027] In the embodiments of the present invention, the technical features described in an open-ended manner include both closed technical solutions composed of the listed features and open technical solutions that include the listed features.

[0028] 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.

[0029] 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.

[0030] 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℃.

[0031] There is still a need to improve the electron mobility and thermal stability of electron transport materials in current related technologies, in order to further improve the driving voltage, luminous efficiency and cycle life of OLED devices.

[0032] The first aspect of this invention provides a benzopentane-containing compound, the chemical structural formula of which is shown below: .

[0033] Ar, R1 to R6 are each independently one of hydrogen, deuterium, halogen, cyano, nitro, C1 to C18 alkyl, C1 to C12 alkoxy, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C3 to C30 heteroaryl.

[0034] Ar1 and Ar2 are each independently one of a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C3-C30 heteroaryl group.

[0035] L1 to L3 are each independently one of a single bond, a substituted or unsubstituted C6-C60 arylene, or a substituted or unsubstituted C3-C30 heteroarylene.

[0036] At least one of Z1 to Z3 is N, and the rest are CH.

[0037] A is one of O, S, Se, CR7R8, and R7 and R8 are each independently one of C1~C12 alkyl, C1~C8 alkoxy, substituted or unsubstituted C2~C8 enyl, substituted or unsubstituted C2~C8 alkynyl, substituted or unsubstituted C6~C60 aryl, or substituted or unsubstituted C3~C60 heteroaryl.

[0038] 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.

[0039] Examples of chain alkyl groups include, for example, 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.

[0040] In the embodiments of this invention, "olefinic alkyl" refers to a straight-chain or branched unsaturated hydrocarbon. The olefinic alkyl can be a chain-like olefinic alkyl or a cyclic olefinic alkyl.

[0041] Examples of chain-like alkenyl groups include, for example, vinyl, 1-propenyl, isopropenyl, 2-butenyl, 3-methyl-2-butenyl, 1-pentenyl, 2-methyl-2-butenyl, hexenyl, heptenyl, octenyl, etc.

[0042] In the embodiments of this invention, "alkynyl group" refers to a straight-chain or branched unsaturated hydrocarbon. This alkynyl group can be either a chain-like or cyclic alkynyl group.

[0043] Examples of chain-like alkynyl groups include, for example, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-methyl-1-butynyl, 1-pentynyl, tert-pentynyl, hexynyl, heptynyl, octyynyl, etc.

[0044] 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 C6, C7, C8, C9, C10, 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.

[0045] "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.

[0046] 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.

[0047] "Sub-heteroaryl" refers to the subunit of a heteroaryl group. For the meaning and explanation of the heteroaryl groups involved, please refer to the relevant explanations of heteroaryl groups mentioned above.

[0048] Hydrogen includes isotopes with different numbers of neutrons, namely protium, deuterium, and tritium.

[0049] The benzopentacyclic compounds provided in this invention are triazine-based nitrogen-containing six-membered heterocycles and benzopentacyclic rings formed through specific sites. The introduction of the benzopentacyclic ring effectively reduces intermolecular interactions, significantly lowering the deposition temperature of the compound and thus improving its heat resistance. Furthermore, the introduction of the benzopentacyclic ring facilitates the formation of amorphous films, which is beneficial for improving device lifetime. In addition, the introduction of the nitrogen-containing six-membered heterocycle effectively modulates the HOMO and LUMO energy levels of the compound and enhances its electron mobility, helping to reduce the operating voltage of the device.

[0050] In some examples, Ar is selected from one of cyano, triazine, spirofluorene, or nitrogen-containing heteroaryl groups.

[0051] The cyano group is a strong electron-withdrawing group. When Ar is selected from the cyano group, it can significantly lower the LUMO energy level of the compound, improve the electron mobility, and help reduce the driving voltage of the device. When Ar is selected from the triazine group, it can expand the conjugated electron-deficient system of the compound, which helps to improve the electron mobility. The spirocyclic structure of spirofluorene groups can disrupt the molecular planarity, reduce intermolecular π-π stacking, and lower the evaporation temperature of the compound. Nitrogen-containing heteroaryl groups can lower the electron injection barrier and improve the electron injection efficiency.

[0052] In some examples, the chemical structural formulas of spirofluorene groups are shown below: .

[0053] The chemical structural formula of the triazine group is shown below: .

[0054] The chemical structural formula of the nitrogen-containing heteroaryl group is shown below: .

[0055] Ar3 to Ar6 are each independently one of a substituted or unsubstituted C6-C30 arylene or a substituted or unsubstituted C3-C30 heteroarylene.

[0056] L4 to L5 are each independently represented by a single bond, O, S, Se, and CR9R. 10 one of them.

[0057] B represents O, S, Se, NR. 11 .

[0058] At least one of Z4 to Z6 is N, and the rest are CH.

[0059] Z7 to Z 10 Each is independently N or CR 12 .

[0060] Ar7 to Ar9, R9 to R 12 Each of them independently consists of one of hydrogen, deuterium, halogen, cyano, nitro, C1-C18 alkyl, C1-C12 alkoxy, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C3-C30 heteroaryl.

[0061] By imposing the above restrictions on Ar, the compound exhibits advantages such as good thermal stability and good electron mobility.

[0062] The substituted or unsubstituted C6~C60 aryl groups mentioned above can be substituted or unsubstituted C6~C30 aryl groups, and the substituted or unsubstituted C3~C60 heteroaryl groups can be substituted or unsubstituted C3~C30 heteroaryl groups.

[0063] The substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C3-C30 heteroaryl groups mentioned above can be the following substituted or unsubstituted aryl and heteroaryl groups: Phenyl, deuterated phenyl, tolyl, naphthyl, phenanthryl, anthracene, perylyl, fluoranthyl, pyrene, 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, carbazoleindolyl, fluorencarbazole, imidazolyl, oxazolyl, thiazolyl, thiadiazolyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl, azadibenzofuranyl, azadibenzothiopheneyl.

[0064] Optionally, when aryl and heteroaryl groups are substituted, the substituents are C1-C12 alkyl groups.

[0065] In some examples, L1 to L3 are each independently one of a single bond, phenylene, biphenylene, cyanobiphenyl, benzonitrile, phenylnaphthyl, phenylanthryl, spiro[cyclopentane-1,9'-fluorene]yl, 9,9-dimethylfluoreneyl, and phenyl-9,9-dimethylfluoreneyl.

[0066] Single bonds allow phenyl groups to form the shortest conjugated chains with triazine groups, benzo[a]-5-membered ring groups, and Ar groups, maintaining the rigid planar structure of the molecule. Phenylidene, biphenylene, phenylnaphthyl, and phenylanthrayl groups can appropriately lengthen the conjugated system, improving the electron mobility of the compound. Cyanobiphenyl and benzonitrile groups have strong electron-withdrawing properties, which can lower the LUMO energy level of the compound and improve its electron mobility. Spiro[cyclopentane-1,9'-fluorene] groups have a three-dimensional rigid structure, which can lower the evaporation temperature of the compound. 9,9-dimethylfluorene groups can generate three-dimensional steric hindrance, improving the film-forming properties of the compound, which is beneficial for improving device lifetime. Phenyl-9,9-dimethylfluorene groups can both generate three-dimensional steric hindrance and lengthen the conjugated system, improving the electron mobility of the compound and its film-forming properties. Therefore, by limiting L1 to L3 as described above, it not only helps to reduce the vapor deposition temperature of the compound and improve its heat resistance, but also improves its film-forming properties. At the same time, it can also adjust the LUMO energy level of the compound and improve its electron mobility, which is beneficial for improving the device's lifetime and luminous efficiency, and reducing the device's operating voltage.

[0067] In some examples, two of Z1 to Z3 are N and the other is CH; or, all of Z1 to Z3 are N.

[0068] When two of Z1 to Z3 are N and the other is CH, the corresponding group is pyrimidinyl. When all of Z1 to Z3 are N, the corresponding group is triazineyl. Pyrimidinyl and triazineyl groups have strong electron-withdrawing properties, which can significantly reduce the LUMO energy level of the compound and improve the electron mobility of the compound, which is beneficial for reducing the operating voltage of the device.

[0069] In some examples, R1 to R2 are each independently one of hydrogen, deuterium, and methyl.

[0070] R3 to R6 are each independently one of hydrogen, deuterium, cyano, phenyl, benzonitrile, or pyridinyl.

[0071] By limiting R1 to R2 as described above, molecular planarity can be maintained, the conjugated system can be maximized, and the electron mobility of the compound can be improved.

[0072] For R3 to R6, hydrogen and deuterium can maintain molecular planarity, maximize the conjugated system, and ensure electron transport capability. The cyano group has strong electron-withdrawing properties, which can lower the LUMO level of the compound. The phenyl group can extend the conjugated system, the benzonitrile group can both extend the conjugated system and has strong electron-withdrawing properties, and the pyridyl group can coordinate with the metal electrode, which helps improve electron injection. Therefore, by limiting R3 to R6 as described above, it is helpful to lower the LUMO level of the compound and improve its electron mobility.

[0073] In some examples, Ar1 and Ar2 are each independently one of phenyl, biphenyl, cyanobiphenyl, adamantylphenyl, pyridylphenyl, dibenzofuranyl, benzonitrile, dibenzothiophene, 9,9-dimethylfluorenyl, and phenanthrene.

[0074] By limiting Ar1 and Ar2 as described above, it is helpful to reduce the LUMO energy level of the compound, improve the electron mobility of the compound, and reduce the evaporation temperature of the compound.

[0075] In summary, the benzopentane-containing compounds provided in this invention possess suitable HOMO and LUMO energy levels, enabling excellent carrier injection capability and a balance between carrier injection and transport; the benzopentane-containing compounds have high triplet energy levels (T1 > 2.3 eV), effectively limiting exciton diffusion and thus improving energy utilization efficiency; the benzopentane-containing compounds have high glass transition temperatures (Tg > 150 °C), ensuring excellent thermal stability of the thin film material and extending device lifetime; the benzopentane-containing compounds have excellent electron mobility (~10⁻¹⁰ eV). -5 cm 2 The luminous efficiency ( / V·s) can promote electron transport, reduce the operating voltage of the device, and significantly improve the device efficiency. The synergistic effect of these characteristics enables overall optimization of key performance indicators such as driving voltage, luminous efficiency, device lifetime, and stability under high current density.

[0076] Regarding the benzopentane-containing compounds mentioned above, some examples of these compounds are listed below, see Compound 1-Compound 904.

[0077]

[0078] Secondly, embodiments of the present invention provide the application of any of the above-mentioned benzopentane-containing compounds in organic electroluminescent devices, organic solar cells, organic thin-film transistors, organic photodetectors, organic field-effect transistors, organic integrated circuits, or organic photoreceptors.

[0079] Thirdly, embodiments of the present invention provide an electron transport material, which includes any of the benzopentane-containing compounds mentioned in the first aspect above.

[0080] The electron transport material provided in this embodiment of the invention has all the advantages of the benzopentane-containing compounds involved in this embodiment of the invention.

[0081] The electron transport material provided in this invention, when applied to organic electroluminescent devices, can be used to prepare the electron transport layer of the organic electroluminescent device, so that the organic electroluminescent device has both high luminous efficiency, low operating voltage and strong thermal stability.

[0082] The electron transport material provided in this embodiment of the invention, when applied to organic electroluminescent devices, can be used to prepare hole blocking layers for organic electroluminescent devices, effectively blocking holes from entering the electron transport layer, increasing electron recombination in the light-emitting layer, and improving luminous efficiency.

[0083] In some examples, the mass percentage of any benzopentane-containing compound involved in the first aspect of the present invention in the electron transport material is 30wt%-100wt%, including but not limited to the range of 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%, 100%, etc.

[0084] Furthermore, the mass percentage of any benzopentane-containing compound involved in the first aspect of the present invention in the electron transport material is 100 wt%. For example, when the electron transport material is used to prepare an electron transport layer, the benzopentane-containing compound can be used alone.

[0085] In other examples, the electron transport material provided in the embodiments of the present invention includes any of the benzopentane-containing 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% to 70 wt%, including but not limited to the range of one or any two of the following values: 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.

[0086] In this example, the benzopentane-containing 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.

[0087] Furthermore, for this type of electron transport material, the mass percentage of the doped compound is 20wt%-70wt%, and the mass percentage of the benzopentane-containing compound in the electron transport material is 30wt%-80wt%.

[0088] 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.

[0089] 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.

[0090] The aforementioned doped compounds possess suitable electron affinity and excellent electron transport properties. By enabling the doped compounds to synergistically interact with the aforementioned benzopentane-containing compounds, it is beneficial to further improve electron injection efficiency and transport rate, thereby reducing the operating voltage of OLED devices and improving device luminous efficiency.

[0091] To further illustrate, when the aforementioned electron transport materials are used to prepare hole-blocking layers, the doping compounds used can be oxaoxazole compounds, thiazole compounds, triazole compounds, or triazine compounds. Furthermore, hole-blocking materials are typically used alone.

[0092] 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 benzopentane-containing compound involved in the first aspect of the present invention.

[0093] The light-emitting layer material provided in this embodiment of the invention possesses all the advantages of the benzopentane-containing 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 electron-hole ratio in the light-emitting layer and thus improving the luminous efficiency of the OLED device.

[0094] 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.

[0095] The mass percentage of the luminescent host compound in the host material is 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%.

[0096] By employing the synergistic effect of the aforementioned host luminescent compound and a benzopentane-containing compound, the luminous efficiency of OLED devices is ensured while also optimizing charge transport balance, reducing non-radiative losses, and improving device stability. Furthermore, it facilitates the regulation of exciton distribution in the luminescent layer, suppresses exciton quenching, and broadens luminous adaptability.

[0097] 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.

[0098] 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.

[0099] In some examples, the benzopentane-containing compound is suitable for tandem blue light materials, which can significantly improve the overall performance of the device.

[0100] 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 a benzopentane-containing compound as described in the first aspect of the present invention.

[0101] 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.

[0102] The organic electroluminescent device provided in this embodiment of the invention possesses all the advantages of the benzopentane-containing compounds involved in this embodiment. For example, the organic electroluminescent device combines high luminous efficiency, low operating voltage, and strong thermal stability.

[0103] 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.

[0104] The following examples illustrate this point.

[0105] 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.

[0106] 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.

[0107] 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.

[0108] 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.

[0109] In the various examples mentioned above, at least one of the electron injection layer, electron transport layer, and hole blocking layer includes the benzopentane-containing compound 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.

[0110] In some examples, the electron injection layer materials used in the electron injection layer include, but are not limited to: benzopentane-containing compounds, alkali metals, alkali metal-containing compounds, alkaline earth metals, alkaline earth metal-containing compounds, and alkaline earth metal-containing complexes involved in the embodiments of the present invention.

[0111] Furthermore, the electron injection layer material includes, but is not limited to: benzopentane-containing compounds, 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 involved in the embodiments of the present invention.

[0112] Furthermore, the electron injection layer material includes, but is not limited to: benzopentane-containing compounds involved in the embodiments of the present invention, 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.

[0113] 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.

[0114] The following examples illustrate this point.

[0115] 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.

[0116] 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.

[0117] 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.

[0118] 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 compounds, fluorene compounds, phthalocyanine compounds, polythiophene, polyethylene, polybenzenesulfonic acid, quinone compounds, and hexacyanohexatribenzene.

[0119] For example, the materials involved in the hole transport layer and the electron blocking layer can be any of the following compounds.

[0120]

[0121] For example, the material involved in the hole injection layer can be any of the following compounds.

[0122]

[0123] 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.

[0124] 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.

[0125] 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.

[0126] 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.

[0127] 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.

[0128] 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.

[0129] For example, the display device may be a mobile phone, tablet, laptop, wearable device, television, electronic screen, vehicle display, special display device, etc.

[0130] 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.

[0131] 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 1-904.

[0132] The following examples involve the synthesis of compounds containing benzopentanes. The synthesis process involves the synthesis of intermediate compounds (hereinafter referred to as intermediates). These compounds and intermediates containing benzopentanes are separated by column chromatography and their molecular structures are characterized by elemental analysis and high-resolution mass spectrometry (1HRMS).

[0133] Example 1 Example 1 provides compound 1, the synthetic route and method of which are shown below:

[0134] Step 1: Synthesis of Intermediate 1-1 2-(3-bromo-4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine, benzothiophene-5-borate pinacol ester (1.1 equivalents), 1,1'-bis(diphenylphosphine)ferrocene palladium dichloride (2% equivalents), and potassium carbonate (2.0 equivalents) were dissolved in a 0.2 M dioxane:water mixture at a ratio of 5:1 (v / v) and added to a three-necked flask. The reaction mixture was then heated to reflux under N2 protection and stirred for 5 h. After the reaction was complete, the mixture was cooled to room temperature. Extraction and washing were performed using dichloromethane and a saturated sodium chloride aqueous solution, followed by drying the organic phase with sodium sulfate. The mixture was filtered, the solvent was concentrated to dryness, and the crude product was purified by column chromatography (dichloromethane:n-hexane v / v = 1:10) to obtain the target compound 1-1 in 70% yield.

[0135] Step 2: Synthesis of Compound 1 Intermediate 1-1, spiro[9H-fluorene-9,9′-[9H]oxanthracene]-2′-borate pinacol ester (1.1 equivalents), palladium acetate (0.02 equivalents), xPhos (0.04 equivalents), and potassium carbonate (2.0 equivalents) were dissolved in a 0.2M dioxane:water mixture at a ratio of 5:1 (v / v) and added to a three-necked flask. The reaction mixture was then heated to reflux under N2 protection and stirred for 6 h. After the reaction was complete, the mixture was cooled to room temperature. Extraction and washing were performed using dichloromethane and a saturated sodium chloride aqueous solution, followed by drying of the organic phase with sodium sulfate. The mixture was filtered, the solvent was concentrated to dryness, and the crude product was purified by column chromatography (dichloromethane to n-hexane v / v = 1:6) to obtain target compound 1 in 58% yield.

[0136] Example 2 Example 2 provides compound 4, the synthetic route and method of which are shown below:

[0137] Synthesis of Compound 4 The synthesis method of compound 4 is the same as that of compound 1, with a yield of 65%.

[0138] Example 3 Example 3 provides compound 8, the synthetic route and method of which are shown below:

[0139] Synthesis of Compound 8 The synthesis method of compound 8 is the same as that of compound 1, with a yield of 62%.

[0140] Example 4 Example 4 provides compound 12, the synthetic route and method of which are shown below:

[0141] Synthesis of Compound 12 The synthesis method of compound 12 is the same as that of compound 1, with a yield of 64%.

[0142] Example 5 Example 5 provides compound 34, the synthetic route and method of which are shown below:

[0143] Step 1: Synthesis of intermediate 34-1 The synthesis method of intermediate 34-1 is the same as that of compound 1-1, with a yield of 76%.

[0144] Step 2: Synthesis of Compound 34 The synthesis method of compound 34 is the same as that of compound 1, with a yield of 74%.

[0145] Example 6 Example 6 provides compound 215, the synthetic route and method of which are shown below:

[0146] Synthesis of Compound 215 The synthesis method of compound 215 is the same as that of compound 1, with a yield of 75%.

[0147] Example 7 Example 7 provides compound 197, the synthetic route and method of which are shown below:

[0148] Step 1: Synthesis of intermediate 197-1 The synthesis method of intermediate 197-1 is the same as that of intermediate 1-1, with a yield of 78%.

[0149] Step 2: Synthesis of Compound 197 The synthesis method of compound 197 is the same as that of compound 1, with a yield of 45%.

[0150] Example 8 Example 8 provides compound 218, the synthetic route and method of which are shown below:

[0151] Synthesis of Compound 218 The synthesis method of compound 218 is the same as that of compound 1, with a yield of 80%.

[0152] Example 9 Example 9 provides compound 224, the synthetic route and method of which are shown below:

[0153] Step 1: Synthesis of intermediate 224-1 The synthesis method of intermediate 224-1 is the same as that of intermediate 1-1, with a yield of 81%.

[0154] Step 2: Synthesis of Compound 224 The synthesis method of compound 224 is the same as that of compound 1, with a yield of 85%.

[0155] Example 10 Example 10 provides compound 249, the synthetic route and method of which are shown below:

[0156] Step 1: Synthesis of intermediate 249-1 The synthesis method of intermediate 249-1 is the same as that of intermediate 1-1, with a yield of 72%.

[0157] Step 2: Synthesis of Compound 249 The synthesis method of compound 249 is the same as that of compound 1, with a yield of 63%.

[0158] Example 11 Example 11 provides compound 262, the synthetic route and method of which are shown below:

[0159] Step 1: Synthesis of intermediate 262-1 The synthesis method of intermediate 262-1 is the same as that of intermediate 1-1, with a yield of 75%.

[0160] Step 2: Synthesis of Compound 262 The synthesis method of compound 262 is the same as that of compound 1, with a yield of 67%.

[0161] Example 12 Example 12 provides compound 266, the synthetic route and method of which are shown below:

[0162] Synthesis of Compound 266 The synthesis method of compound 266 is the same as that of compound 1, with a yield of 66%.

[0163] Example 13 Example 13 provides compound 269, the synthetic route and method of which are shown below:

[0164] Step 1: Synthesis of intermediate 269-1 The synthesis method of intermediate 269-1 is described in compound 1-1, with a yield of 80%.

[0165] Step 2: Synthesis of Compound 269 The synthesis method of compound 269 is the same as that of compound 1, with a yield of 78%.

[0166] Example 14 Example 14 provides compound 270, the synthetic route and method of which are shown below:

[0167] Synthesis of Compound 270 The synthesis method of compound 270 is the same as that of compound 1, with a yield of 77%.

[0168] Example 15 Example 15 provides compound 271, the synthetic route and method of which are shown below:

[0169] Synthesis of Compound 271 The synthesis method of compound 271 is the same as that of compound 1, with a yield of 82%.

[0170] Example 16 Example 16 provides compound 409, the synthetic route and method of which are shown below:

[0171] Synthesis of Compound 409 The synthesis method of compound 409 is the same as that of compound 1, with a yield of 68%.

[0172] Example 17 Example 17 provides compound 447, the synthetic route and method of which are shown below:

[0173] Step 1: Synthesis of intermediate 447-1 The synthesis method of intermediate 447-1 is described in compound 1-1, with a yield of 80%.

[0174] Step 2: Synthesis of Compound 447 The synthesis method of compound 447 is the same as that of compound 1, with a yield of 71%.

[0175] Example 18 Example 18 provides compound 510, the synthetic route and method of which are shown below:

[0176] Step 1: Synthesis of intermediate 510-1 The synthesis method of intermediate 510-1 is described in compound 1-1, with a yield of 79%.

[0177] Step 2: Synthesis of Compound 510 The synthesis method of compound 510 is the same as that of compound 1, with a yield of 73%.

[0178] Example 19 Example 19 provides compound 453, the synthetic route and method of which are shown below:

[0179] Synthesis of Compound 453 The synthesis method of compound 453 is the same as that of compound 1, with a yield of 64%.

[0180] Example 20 Example 20 provides compound 569, the synthetic route and method of which are shown below:

[0181] Step 1: Synthesis of intermediate 569-1 The synthesis method of intermediate 569-1 is described in compound 1-1, with a yield of 70%.

[0182] Step 2: Synthesis of Compound 569 The synthesis method of compound 569 is the same as that of compound 1, with a yield of 67%.

[0183] Example 21 Example 21 provides compound 590, the synthetic route and method of which are shown below:

[0184] Synthesis of Compound 590 The synthesis method of compound 590 is the same as that of compound 1, with a yield of 76%.

[0185] Example 22 Example 22 provides compound 593, the synthetic route and method of which are shown below:

[0186] Step 1: Synthesis of intermediate 593-1 The synthesis method of intermediate 593-1 is described in compound 1-1, with a yield of 81%.

[0187] Step 2: Synthesis of Compound 593-2 Intermediate 593-1 (1.0 equivalent), pinacol diborate (1.2 equivalent), and dried potassium acetate (1.5 equivalent) were dissolved in 0.3 M dried toluene and added to a three-necked flask. The reaction mixture was then heated to reflux under N2 protection and stirred for 4 h. After the reaction was complete, the mixture was cooled to room temperature. Extraction and washing were performed using dichloromethane and a saturated aqueous sodium chloride solution, followed by drying the organic phase with sodium sulfate. The mixture was filtered, the solvent was concentrated to dryness, and the crude product was purified by column chromatography (ethyl acetate and n-hexane = 1:10) to obtain the target compound 593-2 in 68% yield.

[0188] Step 3: Synthesis of intermediate 593-3 The synthesis method of intermediate 593-3 is the same as that of intermediate 1-1, with a yield of 78%.

[0189] Step 4: Synthesis of Compound 593 The synthesis method of compound 593 is the same as that of compound 1, with a yield of 65%.

[0190] Example 23 Example 23 provides compound 599, the synthetic route and method of which are shown below:

[0191] Synthesis of Compound 599 The synthesis method of compound 599 is the same as that of compound 1, with a yield of 79%.

[0192] Example 24 Example 24 provides compound 609, the synthetic route and method of which are shown below:

[0193] Step 1: Synthesis of intermediate 609-1 The synthesis method of intermediate 609-1 is described in compound 1-1, with a yield of 72%.

[0194] Step 2: Synthesis of Compound 609 The synthesis method of compound 609 is the same as that of compound 1, with a yield of 64%.

[0195] Example 25 Example 25 provides compound 616, the synthetic route and method of which are shown below:

[0196] Step 1: Synthesis of intermediate 616-1 The synthesis method of intermediate 616-1 is the same as that of intermediate 1-1, with a yield of 72%.

[0197] Step 2: Synthesis of intermediate 616-2 The synthesis method of intermediate 616-2 is the same as that of intermediate 593-2, with a yield of 70%.

[0198] Step 3: Synthesis of intermediate 616-3 The synthesis method of intermediate 616-3 is the same as that of intermediate 1-1, with a yield of 77%.

[0199] Step 4: Synthesis of intermediate 616 The synthesis method of intermediate 616 is the same as that of intermediate 1, with a yield of 73%.

[0200] Example 26 Example 26 provides compound 624, the synthetic route and method of which are shown below:

[0201] Step 1: Synthesis of intermediate 624-1 The synthesis method of intermediate 624-1 is the same as that of intermediate 1-1, with a yield of 75%.

[0202] Step 2: Synthesis of intermediate 624-2 The synthesis method of intermediate 624-2 is the same as that of intermediate 593-2, with a yield of 68%.

[0203] Step 3: Synthesis of intermediate 624-3 The synthesis method of intermediate 624-3 is the same as that of intermediate 1-1, with a yield of 75%.

[0204] Step 4: Synthesis of Compound 624 The synthesis method of compound 624 is the same as that of compound 1, with a yield of 71%.

[0205] Example 27 Example 27 provides compound 727, the synthetic route and method of which are shown below:

[0206] Step 1: Synthesis of intermediate 727-1 The synthesis method of intermediate 727-1 is the same as that of intermediate 1-1, with a yield of 73%.

[0207] Step 2: Synthesis of Compound 727 The synthesis method of compound 727 is the same as that of compound 1, with a yield of 65%.

[0208] Example 28 Example 28 provides compound 849, the synthetic route and method of which are shown below:

[0209] Step 1: Synthesis of intermediate 849-1 The synthesis method of intermediate 849-1 is the same as that of intermediate 1-1, with a yield of 78%.

[0210] Step 2: Synthesis of intermediate 849-2 The synthesis method of intermediate 849-2 is the same as that of intermediate 593-2, with a yield of 72%.

[0211] Step 3: Synthesis of Compound 849 The synthesis method of compound 849 is the same as that of compound 1, with a yield of 64%.

[0212] Example 29 Example 29 provides compound 886, the synthetic route and method of which are shown below:

[0213] Step 1: Synthesis of intermediate 886-1 The synthesis method of intermediate 886-1 is the same as that of intermediate 1-1, with a yield of 72%.

[0214] Step 2: Synthesis of intermediate 886-2 The synthesis method of intermediate 886-2 is the same as that of intermediate 593-2, with a yield of 78%.

[0215] Step 3: Synthesis of Compound 886 The synthesis method of compound 886 is the same as that of compound 1, with a yield of 60%.

[0216] Example 30 Example 30 provides compound 889, the synthetic route and method of which are shown below:

[0217] Step 1: Synthesis of intermediate 889-1 The synthesis method of intermediate 889-1 is the same as that of intermediate 1-1, with a yield of 86%.

[0218] Step 2: Synthesis of intermediate 889-2 The synthesis method of intermediate 889-2 is the same as that of intermediate 593-2, with a yield of 85%.

[0219] Step 3: Synthesis of intermediate 889-3 The synthesis method of intermediate 889-3 is the same as that of intermediate 1-1, with a yield of 76%.

[0220] Step 4: Synthesis of Compound 889 The synthesis method of compound 889 is the same as that of compound 1, with a yield of 63%.

[0221] Example 31 Example 31 provides compound 898, the synthetic route and method of which are shown below:

[0222] Step 1: Synthesis of intermediate 898-1 The synthesis method of intermediate 898-1 is the same as that of intermediate 1-1, with a yield of 76%.

[0223] Step 2: Synthesis of intermediate 898-2 The synthesis method of intermediate 898-2 is the same as that of intermediate 593-2, with a yield of 80%.

[0224] Step 3: Synthesis of intermediate 898-3 The synthesis method of intermediate 898-3 is the same as that of intermediate 1-1, with a yield of 82%.

[0225] Step 4: Synthesis of Compound 898 The synthesis method of compound 898 is the same as that of compound 1, with a yield of 73%.

[0226] Example 32 Example 32 provides compound 902, the synthetic route and method of which are shown below:

[0227] Step 1: Synthesis of intermediate 902-1 The synthesis method of intermediate 902-1 is the same as that of intermediate 1-1, with a yield of 80%.

[0228] Step 2: Synthesis of intermediate 902-2 The synthesis method of intermediate 902-2 is the same as that of intermediate 593-2, with a yield of 83%.

[0229] Step 3: Synthesis of intermediate 902-3 The synthesis method of intermediate 902-3 is the same as that of intermediate 1-1, with a yield of 63%.

[0230] Step 4: Synthesis of intermediate 902 The synthesis method of compound 902 is the same as that of compound 1, with a yield of 72%.

[0231] The calculated and measured MS-FAB values ​​of the compounds provided in Examples 1-32 and the intermediates in the synthesis process are shown in Table 1.

[0232]

[0233] The calculated and measured values ​​of the elemental analysis of the compounds provided in Examples 1-32 are shown in Table 2.

[0234]

[0235] According to the test results in Tables 1 and 2, the compounds synthesized in Examples 1-32 have accurate structures and meet the purity standards.

[0236] 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 3.

[0237]

[0238] It should be noted that the triplet energy level T1 is derived from Horiba's Fluorolog. The results were obtained using a 3-series fluorescence spectrometer, with the material test sample being 2×10⁻⁶. 5 A mol / L toluene solution.

[0239] 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.

[0240] The highest occupied molecular orbital (HOMO) energy level was measured by the ionization energy testing system (AC-2) in an atmospheric environment.

[0241] LUMO = HOMO + Eg, where Eg was measured using a dual-beam UV-Vis spectrophotometer (model: Hatachi U2900).

[0242] 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.

[0243] 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.

[0244] 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.

[0245] 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.

[0246] Electron transport layer: The above-mentioned benzopentane-containing compounds and LiQ (thickness of 60 nm) are vapor-deposited on the surface of the hole injection layer as an electron transport layer. The mass percentage of the benzopentane-containing compounds and lithium 8-hydroxyquinoline (LiQ) is 50%, and the two are combined to form an electron transport material. The vapor deposition rate of both is 0.05 nm / s.

[0247] 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.

[0248] 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.

[0249] Table 3 shows the electron mobility of the electron transport layer for each electron transport material at a thickness of 60 nm. The electron mobility in Table 3 is expressed in scientific notation. In this embodiment of the invention, the value aE-b described in scientific notation is equivalent to a × 10⁻¹⁰. b For example, 1×10 4 It can be written as 1E4.

[0250] As shown in Table 3, 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 174°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 lifetime and luminous stability of organic electroluminescent devices.

[0251] The compounds provided in this invention all possess suitable HOMO and LUMO energy levels, which can reduce the carrier injection barrier, lower device voltage, and improve device efficiency. Specifically, the HOMO (highest occupied molecular orbital) of each compound is generally deep (-5.82 eV to -6.29 eV), which helps to block holes migrating from the anode direction, reducing device leakage current and thus improving device current efficiency. Furthermore, the higher HOMO energy level can also reduce the number of holes leaving the emissive layer, increasing the recombination probability of electrons and holes in the emissive layer.

[0252] The compounds provided in this invention possess high triplet energy levels (T1 levels). Specifically, the T1 of each compound is higher than 2.3 eV, with some even exceeding 2.5 eV. This characteristic is particularly important for blue phosphorescent OLEDs: a high T1 effectively prevents excitons from diffusing back from the emissive layer to the transport layer, ensuring efficient energy transfer between host and guest components and suppressing energy loss caused by non-radiative transitions. Furthermore, the high triplet energy level also helps reduce the number of excitons leaving the emissive layer, thereby improving the efficiency of exciton conversion luminescence.

[0253] 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 and current efficiency.

[0254] Application Examples The following examples, Application Examples 1-32 and Comparative Examples 1-16, further illustrate the application effects of the compounds provided in the above examples in OLED devices. The OLED devices involved in Examples 1-32 and Comparative Examples 1-16 are manufactured using the same process, employing the same substrate and electrode materials, and maintaining the same electrode film thickness. The difference lies in the electron transport layer or hole blocking layer of the different OLED devices.

[0255] See Figure 1 The OLED device comprises 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 luminescent material) / hole blocking layer (HBL) / electron transport layer (ETL) / electron injection layer (EIL) / cathode / light extraction layer (CPL).

[0256] The fabrication method of the OLED device corresponding to Application Example 1 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.

[0257] Hole injection layer: Compound HT and p-dopant (mass ratio of 97:3, thickness of 10nm) were deposited on ITO as hole injection layer at a deposition rate of 0.1nm / s.

[0258] 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.

[0259] Electron blocking layer: Compound EB is deposited on the surface of the hole transport layer to form a 10 nm thick electron blocking layer at a deposition rate of 0.1 nm / s.

[0260] 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.

[0261] Hole blocking layer: Compound 1 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.

[0262] Electron transport layer: A 30 nm thick compound ET-1:LiQ (weight ratio 5:5) was deposited on the surface of the hole blocking layer as an electron transport layer. LiQ is lithium 8-hydroxyquinoline, and the deposition rate was 0.1 nm / s.

[0263] Electron injection layer: A 1 nm thick LiQ layer is deposited on the surface of the electron transport layer as the electron injection layer.

[0264] Cathode: A cathode with a thickness of 15 nm was fabricated on the surface of the electron injection layer. The cathode was made of Mg and Ag with a mass ratio of 1:9.

[0265] Optical extraction layer: An 80nm thick CPL is deposited on the cathode surface as an optical extraction layer.

[0266] The OLED devices provided in Application Examples 2-32 and Comparative Examples 1-16 can be found in Application Example 1 in terms of their fabrication process, and their respective compositions can be found in Table 4 below.

[0267]

[0268] The raw material compounds involved in the fabrication of the aforementioned OLED devices are shown below: .

[0269] The performance of each OLED device listed in Table 4 was tested. During the testing process, a known driving circuit was used to connect the anode and cathode. The test items are as follows: Using a Photo Research PR655 spectrometer, at 1000 cd / cm 2 Under the specified brightness conditions, the driving voltage, turn-on voltage @1 nit, and current efficiency of each device were tested.

[0270] The room temperature and high temperature lifetimes of each device were tested using a Jinghe D3000-96CH lifetime meter under the following conditions: 20 mA / cm². 2 The time (LT95) for the brightness to return to 95% of its initial brightness under current density in both ambient (25°C) and high (85°C) environments is the unit of device lifetime, expressed in Hr.

[0271] The color coordinates of each device were tested using an IVL (current-voltage-luminance) testing system.

[0272] The relevant test data are shown in Table 5.

[0273]

[0274] As shown in Table 5, when electron transport layers or hole blocking layers are prepared using the benzopentane-containing compounds provided in the embodiments of the present invention, the driving voltage of the OLED devices is controlled between 3.40V and 3.60V, all lower than the upper limit of 3.60V. In contrast, the driving voltages of Comparative Examples 1-16 are as high as 3.74V to 3.90V, which is significantly higher.

[0275] When electron transport layers or hole blocking layers are prepared using the benzopentane-containing compounds provided in the embodiments of the present invention, the turn-on voltage of OLED devices is generally between 2.60V and 2.80V, while the turn-on voltages of Comparative Examples 1-16 are between 2.90V and 3.10V. This result indicates that the compounds used in the present invention can effectively reduce the turn-on voltage and driving voltage of the devices, thereby significantly improving the energy efficiency of the devices and reducing power consumption.

[0276] Furthermore, when electron transport layers or hole blocking layers are prepared using the benzopentane-containing compounds provided in the embodiments of the present invention, the current efficiency of the OLED devices is consistently in the range of 220 cd / A to 240 cd / A, significantly higher than the current efficiencies of 180 cd / A to 205 cd / A in Comparative Examples 1-16. This result demonstrates that the compounds used in the present invention can significantly improve the luminous efficiency of the devices, making the energy conversion process more efficient and suitable for display and lighting applications requiring high brightness and low power consumption.

[0277] Furthermore, when electron transport layers or hole blocking layers are prepared using the benzopentane-containing compounds provided in the embodiments of the present invention, the room temperature lifetime (LT95) of the OLED devices is greater than or equal to 235 hours, with most exceeding 240 hours and reaching a maximum of 265 hours. In contrast, the room temperature lifetime of Comparative Examples 1-16 is only 180 to 205 hours.

[0278] When electron transport layers or hole blocking layers are prepared using the benzopentane-containing compounds provided in the embodiments of the present invention at a high temperature of 85°C, the high-temperature lifetime of the OLED devices is greater than or equal to 165 hours, with most devices having a lifetime between 170 and 190 hours. In contrast, the lifetimes of Comparative Examples 1-16 are only 100 to 128 hours, showing a significant difference.

[0279] The above results show that the compounds used in this invention significantly improve the thermal stability and long-term operational reliability of the device, especially under high-temperature operating conditions, where their advantages are even more prominent.

[0280] In summary, when the electron transport layer or hole blocking layer is prepared using the benzopentane-containing compound in the embodiments of the present invention, the organic electroluminescent device exhibits improvements in device voltage, device efficiency, and device lifetime, especially in the driving voltage and lifetime. These performance enhancements are attributed to the high glass transition temperature, suitable HOMO and LUMO energy levels, high T1 energy level, and high electron mobility of the benzopentane-containing compound.

[0281] The above description is merely for the purpose of enabling those skilled in the art to understand the technical solutions 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 containing a benzopentane ring, characterized in that, The chemical structural formula of the benzopentane-containing compound is shown below: ； Ar, R1 to R6 are each independently one of hydrogen, deuterium, halogen, cyano, nitro, C1 to C18 alkyl, C1 to C12 alkoxy, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C3 to C30 heteroaryl. Ar1 and Ar2 are each independently one of a substituted or unsubstituted C6~C30 aryl group or a substituted or unsubstituted C3~C30 heteroaryl group; L1 to L3 are each independently one of a single bond, a substituted or unsubstituted C6~C60 arylene, or a substituted or unsubstituted C3~C30 heteroarylene; At least one of Z1 to Z3 is N, and the rest are CH; A is one of O, S, Se, CR7R8, and R7 and R8 are each independently one of C1~C12 alkyl, C1~C8 alkoxy, substituted or unsubstituted C2~C8 enyl, substituted or unsubstituted C2~C8 alkynyl, substituted or unsubstituted C6~C60 aryl, or substituted or unsubstituted C3~C60 heteroaryl.

2. The benzopentane-containing compound according to claim 1, characterized in that, Ar is selected from one of the following: cyano, triazine, spirofluorene, or nitrogen-containing heteroaryl.

3. The benzopentane-containing compound according to claim 2, characterized in that, The chemical structural formula of the spirofluorene group is shown below: ； The chemical structural formula of the triazine group is shown below: ； The chemical structural formula of the nitrogen-containing heteroaryl group is shown below: ； Ar3 to Ar6 are each independently one of substituted or unsubstituted C6~C30 arylene or substituted or unsubstituted C3~C30 heteroarylene; L4 to L5 are each independently represented by a single bond, O, S, Se, and CR9R. 10 one of; B represents O, S, Se, NR. 11 ; At least one of Z4 to Z6 is N, and the rest are CH; Z7 to Z 10 Each is independently N or CR 12 ; Ar7 to Ar9, R9 to R 12 Each of them independently consists of one of hydrogen, deuterium, halogen, cyano, nitro, C1-C18 alkyl, C1-C12 alkoxy, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C3-C30 heteroaryl.

4. The benzopentane-containing compound according to claim 1, characterized in that, L1 to L3 are each independently one of the following: single bond, phenylene, biphenylene, cyanobiphenyl, benzonitrile, phenylnaphthyl, phenylanthrayl, spiro[cyclopentane-1,9'-fluorene]yl, 9,9-dimethylfluoreneyl, and phenyl-9,9-dimethylfluoreneyl.

5. The benzopentane-containing compound according to claim 1, characterized in that, Two of Z1 to Z3 are N, and the other is CH; Alternatively, Z1 to Z3 are all N.

6. The benzopentane-containing compound according to claim 1, characterized in that, R1 to R2 are each independently one of hydrogen, deuterium, and methyl; R3 to R6 are each independently one of hydrogen, deuterium, cyano, phenyl, benzonitrile, or pyridinyl.

7. The benzopentane-containing compound according to claim 1, characterized in that, Ar1 and Ar2 are each independently one of the following: phenyl, biphenyl, cyanobiphenyl, adamantylphenyl, pyridylphenyl, dibenzofuranyl, benzonitrile, dibenzothiophene, 9,9-dimethylfluorenyl, and phenanthrene.

8. The use of the benzopentane-containing compound according to any one of claims 1-7 in organic electroluminescent devices, organic solar cells, organic thin-film transistors, organic photodetectors, organic field-effect transistors, organic integrated circuits, and organic photosensors.

9. An electron transport material, characterized in that, The electron transport material includes the benzopentane-containing compound as described in any one of claims 1-7.

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

11. 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 benzopentane-containing compound as described in any one of claims 1-7.

12. The light-emitting layer material according to claim 11, characterized in that, The host material also includes a luminescent host compound, wherein the luminescent host compound has a mass percentage of 1% to 20%. The luminescent host compound is selected from at least one of the following: naphthalene compounds, pyrene compounds, fluorene compounds, phenanthrene compounds, chrysopraseene 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.

13. 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 includes the benzopentane-containing compound as described in any one of claims 1-7.

14. The organic electroluminescent device according to claim 13, 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 benzopentane-containing compound.

15. A display device, characterized in that, The display device includes the organic electroluminescent device according to any one of claims 13-14.

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