An organic compound and application thereof, and an organic electroluminescence device comprising the same

Abstract

The application provides an organic compound and application thereof, and an organic electroluminescent device containing the same. The organic compound has a structure as shown in formula I. Through design of a molecular structure, charge transmission is facilitated, a molecular HOMO energy level is improved, and charge injection is facilitated. Meanwhile, the organic compound has good stability, is helpful to thermal stability after film formation of the molecule, and exhibits excellent hole transport performance. The organic compound has excellent hole migration efficiency and injection capacity. When the organic compound is used in an organic electroluminescent device, especially in a hole transport layer material, an electron blocking layer material or a hole injection layer material, the working voltage of the device can be effectively reduced, the efficiency of the device is improved, the demand for continuously improved photoelectric performance of an OLED device is further met, and the demand for energy saving of a mobile electronic device is met.

Description

Technical Field

[0001] This invention belongs to the field of organic electroluminescent materials technology, specifically relating to an organic compound and its applications, and organic electroluminescent devices containing the same. Background Technology

[0002] In recent years, optoelectronic devices based on organic materials have developed rapidly and have gradually become a research hotspot in the field. These organic optoelectronic devices include organic light-emitting diodes (OLEDs), organic field-effect transistors, organic photovoltaic cells, and organic sensors. Among them, OLEDs can provide highly saturated red, green, and blue colors. Full-color display devices made with OLEDs do not require an additional backlight and have advantages such as vibrant colors, thinness, flexibility, high contrast, and low power consumption. Therefore, their development has been particularly rapid, and they have already achieved commercial success in the field of information display.

[0003] The core of OLED devices is a multilayer thin-film structure containing various organic functional materials. Common organic functional materials include: hole injection materials, hole transport materials, hole blocking materials, electron injection materials, electron transport materials, electron blocking materials, host light-emitting materials, and guest light-emitting materials (dyes). When an electric current is applied, electrons and holes are injected and transported to the light-emitting region, where they recombine, thereby generating excitons and emitting light.

[0004] Common fluorescent emitters primarily utilize singlet excitons generated when electrons and holes combine to emit light, and are still widely used in various OLED products. Some metal complexes (such as iridium complexes) can simultaneously utilize both triplet and singlet excitons to emit light, and are called phosphorescent emitters, with energy conversion efficiencies up to four times higher than traditional fluorescent emitters. Thermally excited delayed fluorescence (TADF) technology promotes the conversion of triplet excitons to singlet excitons, achieving high luminous efficiency without the use of metal complexes, while still effectively utilizing triplet excitons. Thermally excited sensitized fluorescence (TASF) technology uses materials with TADF properties to sensitize the emitter through energy transfer, also achieving high luminous efficiency.

[0005] Hole transport materials have a significant impact on device performance. On the one hand, hole transport materials need suitable HOMO energy levels, and a suitable bandgap between the hole material and the anode facilitates hole injection, which can help reduce operating voltage. On the other hand, hole transport materials regulate the carrier transport balance within the device; improving the carrier mobility of the hole transport material can increase luminous efficiency and delay device decay. Although products using OLED display technology are already commercialized, there are still requirements for further improvement in device efficiency and lifespan.

[0006] Therefore, developing a wider variety of higher-performance organic materials to improve the luminous efficiency and lifespan of organic electroluminescent devices and reduce driving voltage is an urgent problem to be solved in this field. Summary of the Invention

[0007] In response to the shortcomings of existing technologies feet The purpose of this invention is to provide an organic compound and its application, and an organic electroluminescent device containing the organic compound. The organic compound has high hole injection capability, high mobility and excellent charge transport capability, and is suitable as a hole transport material. When applied to an organic electroluminescent device, it can improve the luminous efficiency of the device and reduce the driving voltage.

[0008] To achieve this objective, the present invention adopts the following technical solution:

[0009] One object of the present invention is to provide an organic compound having the structure shown in Formula I:

[0010]

[0011] In Formula I, L is selected from any one of substituted or unsubstituted C6-C60 arylene or substituted or unsubstituted C3-C60 heteroarylene.

[0012] In Formula I, Ar1, Ar2, Ar3, and Ar4 are each independently selected from any one of substituted or unsubstituted C6-C60 aryl groups or substituted or unsubstituted C3-C60 heteroaryl groups.

[0013] In Formula I, R1 and R2 are each independently selected from any one of the following: halogen, cyano, nitro, hydroxyl, amino, aldehyde, ester, substituted or unsubstituted C1-C30 straight-chain or branched alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C1-C30 thioalkoxy, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C2-C30 heterocycloalkyl, substituted or unsubstituted C1-C30 alkylsilyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C3-C60 heteroaryl, substituted or unsubstituted C6-C60 arylamino, and substituted or unsubstituted C3-C60 heteroarylamino.

[0014] In Formula I, a and b are each independently selected from integers from 0 to 4, for example, they can be 0, 1, 2, 3 or 4.

[0015] Wherein, when a > 1, the plurality of (at least 2) R1s are the same or different groups; when b > 1, the plurality of (at least 2) R2s are the same or different groups. When a and b are each independently > 1, the plurality of (at least 2) R1s and the plurality of (at least 2) R2s are independently not connected, or can be connected to form a ring through chemical bonds.

[0016] The substituents described in L, Ar1, Ar2, Ar3, Ar4, R1, and R2 are each independently selected from at least one of the following: C1-C20 straight-chain or branched alkyl, C1-C20 alkoxy, C1-C20 thioalkoxy, C3-C20 cycloalkyl, C2-C20 heterocycloalkyl, C1-C20 alkylsilyl, C6-C30 aryl, C6-C30 aryloxy, C3-C30 heteroaryl, C6-C30 arylamino, or C3-C30 heteroarylamino.

[0017] The organic compound provided by this invention has the structure shown in Formula I, which is a compound with a diarylamine structure constructed using a triphenylene ring as the parent core; wherein, the triphenylene ring is a fused ring structure with a large conjugated plane, and the delocalized distribution of the π electron cloud can enhance electron mobility, with one end connected to the aromatic amine structure. Direct connection facilitates charge transport and increases the HOMO energy level of the molecule, which is beneficial for charge injection. Simultaneously, the conjugated fused-ring structure of triphenylene exhibits good stability, contributing to the thermal stability of the molecule after film formation. In the triphenylene structure... The introduction of aromatic amine groups at the 1- and 4-positions enhances charge transport capability. This is because when the aromatic amine substituent is in the para position, the electron cloud density at the para position is high due to the electron-donating properties of the amine group. Furthermore, the introduction of the unilateral bridging group L further expands the delocalized (delocalized) range of electrons in the triphenylene structure, thus improving the overall charge transport capability of the molecule and exhibiting excellent hole transport performance. These structural characteristics enable the organic compound provided by this invention to possess excellent hole migration efficiency and injection capability. When applied to organic electroluminescent devices, it can effectively reduce the operating voltage of the device and improve its efficiency.

[0018] It should be noted that, for ease of explanation, the possible effects of each group / feature have been described separately in this invention, but this does not mean that these groups / features act in isolation. In fact, the reason for achieving good performance is essentially the optimized combination of the entire molecule, the result of the synergistic effect between various groups, rather than the effect of a single group.

[0019] In this invention, the halogen can be fluorine, chlorine, bromine, or iodine. The same descriptions used below have the same meaning.

[0020] In the present invention, the "substituted or unsubstituted" group may be substituted with one substituent or multiple substituents. When there are multiple substituents (at least two), they may be the same or different substituents. When the following text involves the same expression, it has the same meaning, and the selection range of the substituents is as shown above, and will not be elaborated one by one.

[0021] In the present invention, for the description of chemical elements, if there is no special explanation, it includes the concept of isotopes with the same chemical properties. For example, hydrogen (H) includes

[0022] , , ,

[0028] ,

[0027] , 13 , 3 , , 12 , 1 ,

[0026] , 2 , ,

[0025] , ,

[0024] , ,

[0023] , H (protium), 2 H (deuterium, D), 3 H (tritium, T), etc.; carbon (C) includes 12 C, 13 C, etc.

[0022] In the present invention, the heteroatoms of the heteroaryl group are selected from atoms or atomic groups of N, O, S, P, B, Si or Se, preferably N, O, S. <​​​​​​​​​​​​​​​C1 to C30 can all be C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C22, C24, C26, or C28, etc.

[0029] C3 to C30 can all be C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C22, C24, C26, or C28, etc.

[0030] C2 to C30 can all be C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C22, C24, C26, or C28, etc.

[0031] C1 to C20 can all be C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.

[0032] C3 to C20 can all be C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, or C19, etc.

[0033] C2 to C20 can all be C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, or C19, etc.

[0034] C6 to C30 can all be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, or C28, etc.

[0035] C3 to C30 can all be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, or C28, etc.

[0036] In this invention, the C6-C60 aryl group, preferably C6-C30 aryl group, and more preferably C6-C20 aryl group, includes monocyclic aryl and fused-ring aryl groups; the monocyclic aryl group means that the group contains at least one phenyl group, and when it contains at least two phenyl groups, the phenyl groups are linked by single bonds, including but not limited to: phenyl, biphenyl, terphenyl, etc.; the fused-ring aryl group means that the group contains at least two aromatic rings, and the aromatic rings share two adjacent rings. Groups in which carbon atoms are fused together, exemplary including but not limited to: naphthyl, anthraceneyl, phenanthryl, indeneyl, fluorenyl and their derivatives (9,9-dimethylfluorenyl, 9,9-diethylfluorenyl, 9,9-dipropylfluorenyl, 9,9-dibutylfluorenyl, 9,9-dipentylfluorenyl, 9,9-dihexylfluorenyl, 9,9-diphenylfluorenyl, 9,9-dinaphthylfluorenyl, spirodifluorenyl, benzo[a]fluorenyl, etc.), fluoranthyl, triphenylene, pyrene, perylene, Benzyl or tetraphenyl, etc.

[0037] The C3-C60 heteroaryl group, preferably C3-C30 heteroaryl group, more preferably C4-C20 heteroaryl group, and even more preferably C5-C12 heteroaryl group, includes monocyclic heteroaryl groups or fused-ring heteroaryl groups. A monocyclic heteroaryl group means that the molecule contains at least one heteroaryl group. When the molecule contains one heteroaryl group and other groups (such as aryl, heteroaryl, alkyl, etc.), the heteroaryl group and other groups are connected by a single bond, exemplarily including but not limited to: furanyl, thiophene, pyrrole, pyridyl, etc. The term "fused-ring heteroaryl" refers to a molecule containing at least one aromatic heterocycle and one aromatic ring (aromatic heterocycle or aromatic ring), and the two share two adjacent atoms fused together in a group. Examples include, but are not limited to: benzofuranyl, benzothiophenyl, isobenzofuranyl, isobenzothiophenyl, indolyl, dibenzofuranyl, dibenzothiophenyl, carbazoleyl and its derivatives (N-phenylcarbazoleyl, N-naphthylcarbazoleyl, benzocarbazoleyl, dibenzocarbazoleyl, indolocarbazoleyl, azacarbazoleyl, etc.), acridineyl, phenazinyl, phenothiazinyl, phenotoxazinyl, hydrogenated acridineyl, etc.

[0038] Specific examples of aryl groups in this invention can be exemplified by removing one hydrogen atom from the aforementioned aryl examples to obtain a divalent group. Specific examples of heteroaryl groups in this invention can be exemplified by removing one hydrogen atom from the aforementioned heteroaryl examples to obtain a divalent group.

[0039] Specific examples of aryl groups in this invention include the monovalent groups formed by the aryl group and oxygen.

[0040] The C6-C60 arylamino groups include, but are not limited to, phenylamino, methylphenylamino, naphthylamino, anthraceneylamino, phenanthreneamino, and biphenylamino.

[0041] The C3-C60 heteroarylamino group includes, but is not limited to, pyridinylamino, pyrimidinylamino, and dibenzofuranylamino.

[0042] The C1-C30 straight-chain or branched alkyl group, preferably C1-C20 straight-chain or branched alkyl group, more preferably C1-C16 straight-chain or branched alkyl group, and even more preferably C1-C10 straight-chain or branched alkyl group, includes, but is not limited to: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-octyl, n-heptyl, n-nonyl, n-decyl, etc.

[0043] The C3 to C30 cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and adamantyl.

[0044] Preferably, a and b are each independently 0 or 1.

[0045] Preferably, the organic compound has a structure as shown in Formula II:

[0046]

[0047] In Equation II, L, Ar1, Ar2, Ar3, and Ar4 have the same range of limitation as in Equation I.

[0048] Preferably, L is selected from any one of substituted or unsubstituted C6-C20 arylene or substituted or unsubstituted C3-C20 heteroarylene.

[0049] Preferably, L is selected from any one of the following groups, whether substituted or unsubstituted: phenylene, biphenylene, terphenylene, naphthylene, triphenylene, fluoreneanthylene, anthracene, fluorene, spirofluorene, carbazolyl, dibenzofuranyl, dibenzothiophene.

[0050] Preferably, the L is selected from any one of the following groups, whether substituted or unsubstituted:

[0051]

[0052] In this context, the dashed lines represent the connection sites of functional groups.

[0053] Preferably, Ar1, Ar2, Ar3, and Ar4 are each independently selected from any one of the following substituted or unsubstituted groups: phenyl, naphthyl, anthracene, benzo[a]anthrayl, phenanthryl, benzo[a]phenanthryl, pyrene, fulvinyl, peryl, fluoranthyl, benzo[a]fluoranthyl, tetraphenyl, pentaphenyl, benzo[a]pyrene, biphenyl, diphenylidene, terphenyl, tetraphenyl, triphenylene, triphenylidene, fluorenyl, spirodifluorenyl, dihydrophenanthryl, dihydropyrene, tetrahydropyrene, etc. cis or trans indofluorenyl, cis or trans monobenzoindofluorenyl, cis or trans dibenzoindofluorenyl, trimerinyl, isotrimerindo, spirotrimerindo, spiroisotrimerindo, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thiopheneyl, benzothiopheneyl, isobenzothiopheneyl, dibenzothiopheneyl, pyrroleyl, indolyl, isoindolyl, carbazoyl, indolocarbazoyl, indocarbazoyl, acridineyl, phenoxazinyl, dibenzo-p-dioxinyl.

[0054] Preferably, Ar1, Ar2, Ar3, and Ar4 are each independently selected from any one of substituted or unsubstituted C6-C20 aryl groups and substituted or unsubstituted C3-C20 heteroaryl groups.

[0055] Preferably, Ar1, Ar2, Ar3, and Ar4 are each independently selected from any one of the following substituted or unsubstituted groups:

[0056]

[0057] In this context, the dashed lines represent the connection sites of functional groups;

[0058] Y1 is selected from O, S, NR 11 or CR 12 R 13 ;

[0059] R 11 R 12 R 13 Each is independently selected from any one of hydrogen, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C3-C30 heteroaryl;

[0060] R 12 and R 13 They can be either not connected or linked together by chemical bonds to form a ring.

[0061] Preferably, the R 11 R 12 R 13 Each is independently selected from any one of methyl, ethyl, n-propyl, isopropyl, phenyl, methylphenyl, biphenyl, naphthyl, or terphenyl.

[0062] Preferably, Ar1, Ar2, Ar3, and Ar4 are each independently selected from any one of the following substituted or unsubstituted groups:

[0063]

[0064]

[0065] In this context, the dashed lines represent the connection sites of functional groups.

[0066] When a substituent group is present in the "substituted or unsubstituted" mentioned above in this invention, each substituent group is independently selected from C1-C10 (e.g., C1, C2, C3, C4, C5, C6, C7, C8, C9, C10) straight-chain or branched alkyl groups, C3-C10 (e.g., C3, C4, C5, C6, C7, C8, C9, C10) cycloalkyl groups, C2-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10) heterocyclic alkyl groups, C1-C10 (e.g., C1, C2, C3, C4, C5, C6, C7, C8, C9, C10) alkoxy groups, C1-C10 (e.g., C1, C2, C3, C4, C5, C6, C7, C8, C9, C10) thioalkoxy groups, C6-C30 (e.g., C6, C10 ... 9. C10, C12, C14, C15, C16, C18, C20, C22, C24, C26 or C28, etc.) arylamino, C3-C30 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26 or C28, etc.) heteroarylamino, C6-C30 ( For example, at least one of the following: aryl groups (e.g., C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, or C28); or at least one of the following: C3-C30 heteroaryl groups (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, or C28).

[0067] Preferably, the organic compound has any one of the following structures from C1 to C128:

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075] A second objective of this invention is to provide an application of the organic compound as described in one objective, wherein the organic compound is used in an organic electroluminescent device.

[0076] Preferably, the organic compound serves as an electron blocking layer material and / or a hole transport layer material in an organic electroluminescent device.

[0077] Preferably, the organic compound is used as a hole injection layer material in an organic electroluminescent device.

[0078] In addition to organic electroluminescent devices, the organic compounds of this invention can also be used in lighting elements, organic thin-film transistors, organic field-effect transistors, organic thin-film solar cells, information tags, electronic artificial skin sheets, sheet-type scanners, or electronic paper.

[0079] A third objective of this invention is to provide an organic electroluminescent device, the organic electroluminescent device comprising a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode; the organic layer comprising at least one organic compound as described in one objective.

[0080] Preferably, the organic layer comprises at least one organic compound with a structure as shown in C1 to C128 as described in one of the objectives.

[0081] Preferably, the organic layer includes a hole transport layer, wherein the hole transport layer includes at least one organic compound as described in any one of the objectives.

[0082] Preferably, the organic layer comprises an electron blocking layer, wherein the electron blocking layer comprises at least one organic compound as described in one of the objectives.

[0083] Preferably, the organic layer includes a hole injection layer, wherein the hole injection layer includes at least one organic compound as described in one of the objectives.

[0084] The organic compounds provided by this invention are suitable for use as hole transport materials in organic electroluminescent devices. When used as any one or a combination of at least two of electron blocking layer materials, hole transport layer materials, or hole injection layer materials, they significantly improve the luminous efficiency of organic electroluminescent devices, reduce driving voltage, reduce energy consumption, and enable the devices to have better overall performance.

[0085] In one specific embodiment, the organic electroluminescent device includes a substrate, and a first electrode, a plurality of light-emitting functional layers (organic layers), and a second electrode sequentially disposed on the substrate; the light-emitting functional layers include any one or a combination of at least two of the following: a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, or an electron injection layer; wherein the light-emitting functional layer (organic layer, such as a hole transport layer, an electron blocking layer, or a hole injection layer) includes at least one compound having the structure shown in Formula I, and more preferably includes at least one organic compound with the structure shown in C1 to C128.

[0086] An OLED includes a first electrode and a second electrode, and an organic layer located between the electrodes. This organic layer can be further divided into multiple regions, such as a hole transport region, a light-emitting layer, and an electron transport region.

[0087] In specific embodiments, a substrate can be used below the first electrode or above the second electrode. The substrate is typically made of glass or polymer material with excellent mechanical strength, thermal stability, water resistance, and transparency. Furthermore, thin-film transistors (TFTs) can also be incorporated into the substrate used for displays.

[0088] The first electrode can be formed by sputtering or depositing the material to be used as the first electrode on a substrate. When the first electrode is used as the anode, it can be a transparent conductive oxide material such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), zinc oxide (ZnO), or any combination thereof. When the first electrode is used as the cathode, it can be a metal or alloy such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), ytterbium (Yb), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof.

[0089] Organic layers can be formed on electrodes using methods such as vacuum thermal evaporation, spin coating, and printing. The compounds used as organic layers can be small organic molecules, large organic molecules, or polymers, as well as combinations thereof.

[0090] The hole transport region is located between the anode and the light-emitting layer. The hole transport region can be a single-layer hole transport layer (HTL), including a single-layer hole transport layer containing only one compound and a single-layer hole transport layer containing multiple compounds. The hole transport region can also be a multilayer structure including at least one of a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL); wherein the HIL is located between the anode and the HTL, and the EBL is located between the HTL and the light-emitting layer; the hole transport region (HIL, HTL, or EBL) contains at least one compound having the structure of Formula I, and more preferably contains at least one organic compound with the structure shown in C1 to C128.

[0091] The material for the hole transport region may also be selected from, but is not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylene ethylene, polyaniline / dodecylbenzenesulfonic acid (Pani / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (Pani / CSA), polyaniline / poly(4-styrenesulfonate) (Pani / PSS), aromatic amine derivatives; wherein, aromatic amine derivatives include compounds shown below HT-1 to HT-51; or any combination thereof.

[0092]

[0093]

[0094]

[0095] The hole injection layer is located between the anode and the hole transport layer. The hole injection layer can be a single compound material or a combination of multiple compounds. For example, the hole injection layer can be an organic compound with the structure shown in Formula I provided by the present invention, one or more compounds of HT-1 to HT-51 mentioned above, or one or more compounds of HI-1 to HI-3 mentioned below; it can also be an organic compound with the structure shown in Formula I provided by the present invention, one or more compounds of HT-1 to HT-51, doped with one or more compounds of HI-1 to HI-3 mentioned below.

[0096]

[0097] The emissive layer includes luminescent dyes (i.e., dopants) that can emit different wavelengths of light, and may also include a host material. The emissive layer can be a monochromatic emissive layer emitting a single color such as red, green, or blue. Multiple monochromatic emissive layers of different colors can be arranged in a planar pattern according to pixel design, or they can be stacked together to form a colored emissive layer. When different colored emissive layers are stacked together, they can be separated from each other or connected to each other. The emissive layer can also be a single colored emissive layer that can simultaneously emit different colors such as red, green, and blue.

[0098] Depending on the technology used, the light-emitting layer material can be various, including fluorescent electroluminescent materials, phosphorescent electroluminescent materials, and thermally activated delayed fluorescence materials. An OLED device can employ a single light-emitting technology or a combination of different technologies. These different light-emitting materials, categorized by technology, can emit light of the same color or different colors.

[0099] In one aspect of the invention, the light-emitting layer employs fluorescent electroluminescence technology. The fluorescent host material of the light-emitting layer may be selected from, but is not limited to, one or more combinations of BFH-1 to BFH-17 listed below.

[0100]

[0101] In one aspect of the invention, the light-emitting layer employs fluorescent electroluminescence technology. The fluorescent dopant of the light-emitting layer may be selected from, but not limited to, one or more combinations of BFD-1 to BFD-24 listed below.

[0102]

[0103]

[0104] In one aspect of the invention, the light-emitting layer employs phosphorescent photoluminescence technology. The main material of the light-emitting layer is selected from, but not limited to, one or more combinations of pH-1 to pH-85.

[0105]

[0106]

[0107]

[0108]

[0109] In one aspect of the invention, the light-emitting layer employs phosphorescent photoluminescence technology. The phosphorescent dopant of the light-emitting layer may be selected from, but not limited to, one or more combinations of GPD-1 to GPD-47 listed below.

[0110]

[0111]

[0112] In one aspect of the invention, the light-emitting layer employs phosphorescent photoluminescence technology. The phosphorescent dopant of the light-emitting layer may be selected from, but not limited to, one or more combinations of RPD-1 to RPD-28 listed below.

[0113]

[0114]

[0115] In one aspect of the invention, the light-emitting layer employs phosphorescent photoluminescence technology. The phosphorescent dopant of the light-emitting layer may be selected from, but is not limited to, one or more combinations of YPD-1 to YPD-11 listed below.

[0116]

[0117] The organic layer of an OLED may also include an electron transport region between the light-emitting layer and the cathode. The electron transport region can be a single-layer electron transport layer (ETL), including single-layer electron transport layers containing only one compound and single-layer electron transport layers containing multiple compounds. Alternatively, the electron transport region can be a multilayer structure including at least one of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0118] In one aspect of the present invention, the electron transport layer material may be selected from, but not limited to, one or more combinations of ET-1 to ET-73 listed below.

[0119]

[0120]

[0121]

[0122]

[0123] In one aspect of the present invention, a hole blocking layer (HBL) is located between the electron transport layer and the light-emitting layer. The hole blocking layer may employ, but is not limited to, one or more compounds of ET-1 to ET-73, or one or more compounds of PH-1 to PH-46; or a mixture of one or more compounds of ET-1 to ET-73 and one or more compounds of PH-1 to PH-46 may be employed.

[0124] The device may also include an electron injection layer located between the electron transport layer and the cathode. The electron injection layer material includes, but is not limited to, one or more combinations of the following: LiQ, LiF, NaCl, CsF, Li2O, Cs2CO3, BaO, Na, Yb, Li or Ca.

[0125] The present invention also provides a display screen or display panel, wherein the display screen or display panel employs the organic electroluminescent device as described above; preferably, the display screen or display panel is an OLED display.

[0126] The present invention also provides an electronic device having a display screen or display panel, wherein the display screen or display panel employs an organic electroluminescent device as described above.

[0127] Compared with the prior art, the present invention has the following beneficial effects:

[0128] The organic compound provided by this invention has the structure shown in Formula I. It is a compound with a diarylamine structure constructed using a triphenylene ring as the parent core. The triphenylene ring has a fused ring structure with a large conjugated plane, which is beneficial for charge transport and increases the HOMO energy level of the molecule, facilitating charge injection. Simultaneously, the conjugated fused ring structure of triphenylene exhibits good stability, contributing to the thermal stability of the molecule after film formation. Introducing aromatic amine groups at the 1- and 4-positions of the triphenylene structure results in a high electron cloud density at the para position, enhancing charge transport capability. Furthermore, the introduction of a unilateral bridging group L further expands the nonlocalized range of electrons in the triphenylene structure, comprehensively improving the molecule's charge transport capability and exhibiting excellent hole transport performance. Through its specially designed molecular structure, this organic compound possesses excellent hole migration efficiency and injection capability. When applied to organic electroluminescent devices, it is particularly suitable as a hole transport layer material, electron blocking layer material, or hole injection layer material. It can effectively reduce the operating voltage of the device, improve device efficiency and lifespan, further meeting the ever-increasing demands for photoelectric performance in OLED devices and the energy-saving requirements of mobile electronic devices. Detailed Implementation

[0129] The technical solution of the present invention will be further illustrated below through specific embodiments. Those skilled in the art should understand that the embodiments described are merely illustrative of the present invention and should not be construed as limiting the invention.

[0130] In one specific embodiment, the organic compound can be prepared by the following synthetic route, wherein Ar1, Ar2, Ar3, Ar4, R1, R2, L, a, and b in the synthetic route have the same defined range as in Formula I.

[0131] Route 1:

[0132]

[0133] Where U1 is a halogen (e.g., chlorine, bromine, or iodine); X1 is... (* represents the linking site of a functional group.)

[0134] Route 2:

[0135]

[0136] U2 and U3 are each independently selected from halogens (such as chlorine, bromine or iodine).

[0137] Route 3:

[0138]

[0139] The specific preparation methods of the organic compounds described in this invention will be detailed below using several synthetic examples, but the preparation methods of this invention are not limited to these synthetic examples.

[0140] It should be noted that obtaining the organic compounds is not limited to the synthetic methods and raw materials used in this invention. Those skilled in the art can also select other methods or routes to obtain the organic compounds provided by this invention. Compounds for which synthetic methods are not mentioned in this invention are all raw material products obtained through commercial means, or self-made using these raw material products according to known methods.

[0141] The mass spectrometry characterization data of the intermediates and organic compounds in this invention were obtained by testing with a ZAB-HS mass spectrometer manufactured by Micromass, UK.

[0142] Synthesis Example 1: Organic compound C1

[0143]

[0144] In a 500 mL three-necked flask, add 17.0 g (50.0 mmol) 1-bromo-4-chlorotriphenylene, 9.4 g (60.0 mmol) p-chlorophenylboronic acid, 0.6 g (0.500 mmol) tetratetraphenylphosphine palladium Pd(PPh3)4, 200 mL toluene, 60 mL ethanol, 50 mL water, and 9.7 g (70.0 mmol) potassium carbonate (K2CO3). The mixture is evacuated under nitrogen three times, and the reaction is heated to 60 °C for 7 h. After the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction mixture, concentrate the organic phase, and purify the crude product by column chromatography (petroleum ether / dichloromethane, 1 / 20) to obtain 13 g of white powder C1-1, m / z measured value: 373.1 (M+H).

[0145] In a 250 mL single-necked flask, 10.0 g (26.9 mmol) of intermediate C1-1, 10.0 g (59.1 mmol) of diphenylamine, 460 mg (0.4 mmol) of tris(dibenzylacetone)dipalladium(O)Pd2(dba)3, 0.2 mL of tri-tert-butylphosphine in xylene solution, 6.5 g (67.3 mmol) of sodium tert-butoxide (NaOBu-t), and 150 mL of toluene were added. The mixture was evacuated under vacuum and purged with nitrogen three times. The reaction was then heated to 120 °C and reacted for 16 h. After the reaction was complete, it was stopped. The mixture was cooled to room temperature, passed through a short silica gel column, and washed with toluene until no product was obtained. The toluene was concentrated to obtain a yellow solid. Methanol was added and stirred, and the solid slowly precipitated. The solid was recrystallized from toluene and ethanol, and filtered to obtain 7.0 g of pale yellow powder compound C1, with a measured m / z value of 639.3 (M+H).

[0146] Synthesis Example 2: Organic compound C2

[0147]

[0148] In a 250 mL single-necked flask, 17.0 g (50.0 mmol) of 1-bromo-4-chlorotriphenylene, 8.4 g (50.0 mmol) of diphenylamine, 460 mg (0.5 mmol) of tris(dibenzylacetone)dipalladium(O), 411 mg (1.0 mmol) of 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl, 5.7 g (60.0 mmol) of sodium tert-butoxide, and 200 mL of toluene were added. The mixture was evacuated under nitrogen three times, and the reaction was heated to 120 °C for 6 h. After the reaction was complete, the reaction was stopped. The mixture was cooled to room temperature, passed through a short silica gel column, and washed with toluene until no product was obtained. The toluene was concentrated to give a yellow solid. Methanol was added and stirred, and the solid slowly precipitated. The solid was recrystallized from toluene and ethanol, and filtered to give 18.0 g of a pale yellow powder compound C2-1, with a measured m / z of 430.1 (M+H).

[0149] In a 250 mL three-necked flask, add 15.0 g (35.0 mmol) C2-1, 5.5 g (40.0 mmol) m-aminophenylboronic acid, 0.4 g (0.300 mmol) tetrakis(triphenylphosphine)palladium, 200 mL toluene, 60 mL ethanol, 50 mL water, and 6.3 g (45.0 mmol) potassium carbonate. The mixture is evacuated under nitrogen three times, and the reaction is heated to 60 °C for 7 h. After the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction mixture, concentrate the organic phase, and stir with n-hexane to obtain 12 g of white powder C2-2, with a measured m / z value of 487.2 (M+H).

[0150] In a 250 mL single-necked flask, 10.0 g (20.6 mmol) C2-2, 7.1 g (45.3 mmol) bromobenzene, 400 mg (0.4 mmol) tris(dibenzylacetone)dipalladium(O), 411 mg (1.0 mmol) 2-biscyclohexylphosphine-2',6'-dimethoxybiphenyl, 7.1 g (51.5 mmol) sodium tert-butoxide, and 200 mL toluene were added. The mixture was evacuated under nitrogen three times, and the reaction was heated to 120 °C for 7 h. After the reaction was complete, the reaction was stopped. The mixture was cooled to room temperature, passed through a short silica gel column, and washed with toluene until no product was obtained. The toluene was concentrated to give a yellow solid. Methanol was added and stirred, and the solid slowly precipitated. The solid was recrystallized from toluene and ethanol, and filtered to give 18.0 g of pale yellow powder compound C2, with an measured m / z value of 639.2 (M+H).

[0151] Synthesis Example 3: Organic compound C16

[0152]

[0153] The synthesis of C16-2 is based on the synthesis of C2-2 in Synthesis Example 2, except that m-aminophenylboronic acid is replaced with p-aminophenylboronic acid to obtain C16-2. The measured m / z value is 487.2 (M+H).

[0154] The synthesis of C16 can refer to the synthesis of C2 in Synthesis Example 2. Replace C2-2 with C16-2 and replace bromobenzene with 4-bromobiphenyl to obtain C16. The measured m / z value is 791.3 (M+H).

[0155] Synthesis Example 4: Organic compound C18

[0156]

[0157] The synthesis method of C18-1 can refer to the synthesis of C2-1 in Synthesis Example 2. Replace diphenylamine with bis(4-biphenyl)amine to obtain C18-1. The measured m / z value is 582.2 (M+H).

[0158] The synthesis method of C18-2 can refer to the synthesis of C2-2 in Synthesis Example 2. Replace C2-1 with C18-1 and replace m-aminophenylboronic acid with p-aminophenylboronic acid to obtain C18-2. The measured m / z value is 639.3 (M+H).

[0159] The synthesis of C18 can refer to the synthesis of C2 in Synthesis Example 2. Replace C2-2 with C18-2 and replace bromobenzene with 4-bromobiphenyl to obtain C18. The measured m / z value is 943.4 (M+H).

[0160] Synthesis Example 5: Organic compound C24

[0161]

[0162] The synthesis of C24 can be referenced from the synthesis of C1 in Synthesis Example 1. The diphenylamine is replaced with N-phenyl-1-naphthylamine to obtain C24, with an actual m / z value of 739.3 (M+H).

[0163] Synthesis Example 6: Organic compound C52

[0164]

[0165] The synthesis of C52-1 can refer to the synthesis of C2-1 in Synthesis Example 2. The diphenylamine is replaced with bis(9,9-dimethylfluorene-2-yl)amine to obtain C52-1, with an actual m / z value of 662.3 (M+H).

[0166] In a 250 mL single-necked flask, 10.0 g (15.1 mmol) of C52-1, 5.7 g (19.6 mmol) of triphenylamine 2-boronic acid, 200 mg (0.2 mmol) of tris(dibenzylacetone)dipalladium(O), 165 mg (0.4 mmol) of 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl, 3.1 g (22.7 mmol) of potassium carbonate, and 150 mL of toluene were added. The mixture was evacuated under nitrogen three times, and the reaction was heated to 120 °C for 7 h. After the reaction was complete, the reaction was stopped. The mixture was cooled to room temperature, passed through a short silica gel column, and washed with toluene until no product was obtained. The toluene was concentrated to obtain a yellow solid. Methanol was added and stirred, and the solid slowly precipitated. The solid was recrystallized from toluene and ethanol, and filtered to obtain 6.0 g of pale yellow powder compound C52, with a measured m / z value of 871.4 (M+H).

[0167] Synthesis Example 7: Organic compound C66

[0168]

[0169] In a 500 mL three-necked flask, add 17.0 g (50.0 mmol) 1-bromo-4-chlorotriphenylene, 18.8 g (60.0 mmol) chlorobenzene 3-phenyl-4-pinacolborate, 450 mg (0.5 mmol) tris(dibenzylacetone)dipalladium(O), 400 mg (1.0 mmol) 2-bicyclohexylphosphine-2',6'-dimethoxybiphenyl, 250 mL dioxane, 50 mL water, and 9.7 g (70.0 mmol) potassium carbonate. The mixture is evacuated and purged with nitrogen three times. The reaction mixture is heated to 60 °C and reacted for 7 h. After the reaction is complete, the reaction is stopped. The mixture is cooled to room temperature, separated, and the organic phase is concentrated. The crude product is purified by column chromatography (petroleum ether / dichloromethane, 1 / 20) to obtain 10 g of white powder C66-1, m / z measured value: 449.1 (M+H).

[0170] In a 250 mL single-necked flask, 10.0 g (22.2 mmol) of intermediate C66-1, 12.5 g (51.1 mmol) of N-phenyl-4-benzidine, 460 mg (0.4 mmol) of tris(dibenzylacetone)dipalladium(O), 0.2 mL of a xylene solution of tri-tert-butylphosphine, 6.5 g (67.3 mmol) of sodium tert-butoxide, and 150 mL of toluene were added. The mixture was evacuated under vacuum and purged with nitrogen three times. The reaction was then heated to 120 °C and reacted for 16 h. After the reaction was complete, it was stopped. The mixture was cooled to room temperature, passed through a short silica gel column, and washed with toluene until no product was obtained. The toluene was concentrated to give a yellow solid. Methanol was added and stirred, and the solid slowly precipitated. The solid was recrystallized from toluene and ethanol, and filtered to give 5.8 g of a pale yellow powder compound C66, with an measured m / z of 867.4 (M+H).

[0171] Synthesis Example 8: Organic compound C87

[0172]

[0173] The synthesis method of C87-1 can refer to the synthesis of compound C1-1 in Synthesis Example 1. Replace p-chlorophenylboronic acid with 4-chloro-1-naphthoboronic acid to obtain C87-1. The measured m / z value is 422.1 (M+H).

[0174] The synthesis of C87 can refer to the synthesis of C1 in Synthesis Example 1, replacing C1-1 with C87-1 and replacing diphenylamine with 9,9-dimethyl-N-phenyl-9H-fluorene-2-amine to obtain C87, with an actual m / z value of 871.4 (M+H).

[0175] Synthesis Example 9: Organic compound C121

[0176]

[0177] The synthesis of C121-1 can be referenced from the synthesis of C2-1 in Synthesis Example 2. The diphenylamine is replaced with N-phenyl-dibenzofuran-4-amine to obtain C121-1, with an actual m / z value of 520.1 (M+H).

[0178] The synthesis of C121 can refer to the synthesis of C52 in Synthesis Example 6. Replace C52-1 with C121-1 and replace 2-boronic acid triphenylamine with intermediate A to obtain C121. The measured m / z value is 819.3 (M+H).

[0179] Synthesis Example 10: Organic compound C128

[0180]

[0181] The synthesis of C128 can refer to the synthesis of C52 in Synthesis Example 6. Replace C52-1 with C2-1 and replace 2-boronic acid triphenylamine with intermediate B to obtain C128. The measured m / z value is 791.3 (M+H).

[0182] Example 1

[0183] An organic electroluminescent device includes an anode (ITO), a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a cathode (Al) arranged sequentially.

[0184] The method for fabricating the organic electroluminescent device is as follows: a glass plate coated with an ITO transparent conductive layer is ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in a mixed solvent of acetone / ethanol, baked in a clean environment until all moisture is removed, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam; the glass substrate with the anode is placed in a vacuum chamber and evacuated to a vacuum level of <1×10⁻⁶. -5 Pa, on the above-mentioned anode film, in sequence, vacuum thermally evaporate 10 nm of compound C1:HI-3 (97 / 3, w / w) mixture as hole injection layer, 60 nm of the organic compound C1 provided by the present invention as hole transport layer, 5 nm of compound HT-14 as electron blocking layer; 20 nm of compound BFH-4:BFD-4 (100 / 3, w / w) mixture as light emission layer; 5 nm of ET-23 as hole blocking layer, 25 nm of compound ET-69:ET-57 (50 / 50, w / w) mixture as electron transport layer, 1 nm of LiF as electron injection layer, and 150 nm of metallic aluminum as cathode; the total evaporation rate of all organic layers and LiF is controlled at 0.1 nm / s, and the evaporation rate of the metal electrode is controlled at 1 nm / s.

[0185] Examples 2-9, Comparative Examples 1-3

[0186] An organic electroluminescent device, which differs from Example 1 only in that the organic compound C1 in the above device is replaced with the organic compounds in Table 1.

[0187] The structures of the hole transport layer materials in Comparative Examples 1-3 are as follows:

[0188]

[0189] The preparation of R-1 can refer to the existing technology KR1020100045587A, the preparation of R-2 can refer to the existing technology CN110606808A, and the preparation of R-3 can refer to the existing technology KR2013078749A.

[0190] The following performance tests were performed on the organic electroluminescent devices provided in Examples 1-9 and Comparative Examples 1-3:

[0191] Under the same brightness, the driving voltage and current efficiency of the organic electroluminescent device were measured as follows: the voltage was increased at a rate of 0.1V per second, and the efficiency was measured when the brightness of the organic electroluminescent device reached 1000 cd / m². 2 The voltage at that time is the driving voltage, and the current density at that time is measured simultaneously; the ratio of brightness to current density is the current efficiency. The test method for the LT98 lifespan is as follows: using a luminance meter at 1000 cd / m²... 2At a constant current, the brightness of the organic electroluminescent device decreased to 980 cd / m² under the specified brightness. 2 The time is measured in hours (h). The test results are shown in Table 1.

[0192] Table 1

[0193]

[0194] As can be seen from the results in Table 1, when the organic compound described in this invention is used as a hole transport material for devices, the current efficiency, driving voltage, and device lifetime are all significantly improved compared with the comparative compounds. This shows that the organic compound described in this invention is a high-performance hole transport material.

[0195] Comparing compound R-1 in Comparative Example 1 with the organic compound C18 described in this invention, in C18, only one side of the aromatic amine unit (nitrogen atom) is bridged to the triphenylene ring via a phenylene group, while in R-1, both sides of the triphenylene ring are bridged to the aromatic amine via benzene rings. For hole transport materials, the conjugated delocalization of π electrons in substituents has a significant impact on transport performance. When the amine group is connected to a group with a larger π electron delocalization, it is beneficial to enhance transport. The benzene rings on both sides of the triphenylene ring weaken the influence of the range of the triphenylene π electron cloud on the hole transport effect. The data results show that the organic compound C18 of this invention, as a hole transport material, has significant performance advantages in both voltage and efficiency. This indicates that the structure of Formula I of this invention can improve the charge transport performance of the material, facilitate charge injection, and has a strong hole carrier transport capability, which is beneficial to the charge transport balance of the device, thereby improving the device efficiency and reducing the operating voltage.

[0196] Similarly, compared with the organic compounds C1 and C2 described in this invention, in Comparative Example 2, compound R-2 has two aromatic amine groups attached to the para position of the triphenylene ring, and the aromatic amine unit (nitrogen atom) on one side is bridged to the triphenylene ring through the benzene ring. In contrast, R-2 has meta (1- and 3-position) substitution, and the two aromatic amine nitrogen atoms are directly connected to the triphenylene ring. The data shows that R-2 has a high voltage and low efficiency, indicating that the hole transport capability of this structure is poor in devices. The organic compounds C1 and C2 provided by this invention show obvious performance advantages.

[0197] Compound R-3 in Comparative Example 3 contains only one aromatic amine group. The device using this compound operates at a voltage of 5.8V and has an efficiency of 5.00 cd / A. In contrast, the organic compound with the structure of Formula I provided by this invention, as a hole transport material, results in a lower operating voltage and higher luminous efficiency. This demonstrates that the organic compound containing this special structure exhibits excellent hole transport performance and is a superior hole transport material.

[0198] In summary, the organic compound of the present invention has the structure shown in Formula I. Through the special design of the molecular structure, the HOMO energy level of the material can be improved, which is conducive to hole injection and thus reduces the operating voltage of the device; it improves the carrier transport capability, enhances the luminous efficiency of the device, and extends the service life, making it a high-performance hole transport material.

[0199] The applicant declares that this invention illustrates an organic compound and its application, as well as an organic electroluminescent device containing the above embodiments, through the above examples. However, this invention is not limited to the above embodiments, meaning that this invention does not necessarily rely on the above embodiments for implementation. Those skilled in the art should understand that any improvements to this invention, equivalent substitutions of raw materials for the products of this invention, additions of auxiliary components, and selection of specific methods all fall within the protection and disclosure scope of this invention.

Claims

1. An organic compound, characterized in that, The organic compound has the structure shown in Formula II: Formula II; Wherein, L is selected from any one of the following groups: , , , ; Ar1, Ar2, Ar3, and Ar4 are each independently selected from any one of the following groups: 、 、 、 、 、 、 、 、 、 、 ； In this context, the dashed lines represent the connection sites of functional groups.

2. The organic compound according to claim 1, characterized in that, The organic compound has any one of the following structures: 。 3. The application of an organic compound as described in claim 1 or 2, characterized in that, The organic compound is used in organic electroluminescent devices.

4. The application according to claim 3, characterized in that, The organic compound serves as an electron blocking layer material and / or a hole transport layer material in organic electroluminescent devices.

5. The application according to claim 3, characterized in that, The organic compound is used as a hole injection layer material in organic electroluminescent devices.

6. An organic electroluminescent device, characterized in that, The organic electroluminescent device includes a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode; the organic layer includes at least one organic compound as described in claim 1 or 2.

7. The organic electroluminescent device according to claim 6, characterized in that, The organic layer includes a hole transport layer, wherein the hole transport layer includes at least one organic compound as described in claim 1 or 2.

8. The organic electroluminescent device according to claim 6, characterized in that, The organic layer includes an electron blocking layer, wherein the electron blocking layer includes at least one organic compound as described in claim 1 or 2.

9. The organic electroluminescent device according to claim 6, characterized in that, The organic layer includes a hole injection layer, wherein the hole injection layer includes at least one organic compound as described in claim 1 or 2.

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