Organic compound, mixture, composition, organic light-emitting device and display panel

Abstract

The invention relates to an organic compound, a mixture, a composition, an organic light-emitting device and a display panel, and the structural general formula of the organic compound is shown in the specification. The organic compound provided by the invention has good hole transport capability, is helpful for adjusting charge balance, can be applied to the organic light-emitting device as a light-emitting auxiliary material, and has good application prospects. The light-emitting efficiency of the organic light-emitting device is greatly improved, the service life of the organic light-emitting device is greatly prolonged, and meanwhile the organic light-emitting device keeps low driving voltage.

Description

Technical Field

[0001] The present application relates to the field of display technology, and in particular to an organic compound, a mixture, a composition, an organic light-emitting device and a display panel. Background Art

[0002] Organic electroluminescence (OEL) technology utilizes the photoelectric properties of organic materials to directly convert electrical energy into light. Organic light-emitting devices based on this technology typically consist of an anode, a cathode, and multiple organic functional layers, including a hole injection layer, a hole transport layer, a light-assisting layer, a light-emitting layer, an electron transport layer, and an electron injection layer. Each layer contains specific organic substances designed to enhance the overall performance of the device. When a voltage is applied between the anode and cathode, holes are injected from the anode and electrons from the cathode. The two combine to form excitons, which release light energy as they return to their ground state. As a representative example of OEL technology, organic light-emitting diodes (OLEDs) have made a significant splash in the flat-panel display and lighting sectors thanks to their numerous advantages, including self-luminescence, high brightness, high efficiency, low voltage, wide viewing angle, and high contrast. Their wide viewing angle, fast response, low voltage requirement, and ultra-thin design fully demonstrate the enormous potential and broad application prospects of OLED technology in the future.

[0003] The selection and design of luminescent auxiliary materials play a vital role in improving the luminous efficiency and extending the service life of OLED devices. Carefully designed luminescent auxiliary materials can effectively balance the carrier transport in OLED devices, effectively inhibit the reverse migration of electrons, and promote the recombination of electrons and holes mainly in the central area of ​​the light-emitting layer, reducing the non-radiative recombination of excitons, thereby improving the luminous efficiency and extending the service life. Therefore, the development of more efficient new luminescent auxiliary materials to further optimize the hole and electron transport balance within the device is the key to improving device efficiency and life and maintaining a low driving voltage. This problem is a topic that researchers in this field urgently need to overcome. Summary of the Invention

[0004] The embodiments of the present application provide an organic compound, a mixture, a composition, an organic light-emitting device, and a display panel. The organic compound has good hole transport capability, helps to regulate charge balance, and can be used as a light-emitting auxiliary material in an organic light-emitting device to significantly improve the luminous efficiency and service life of the organic light-emitting device, while allowing the organic light-emitting device to maintain a low driving voltage.

[0005] In order to achieve the above object, according to the first aspect of the present application, an organic compound is provided, the general structural formula of the organic compound is shown in formula (1):

[0006]

[0007] wherein X is selected from an oxygen atom or a sulfur atom;

[0008] L1 and L2 are selected from any one or more combinations of a single bond, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted dibenzothiophenyl group; the substituent group in the substituted or unsubstituted group is selected from a deuterium atom or a phenyl group;

[0009] Ar1 is selected from a hydrogen atom or any one of the following groups, and Ar2 is selected from a single bond or any one of the following groups:

[0010]

[0011]

[0012] “*” indicates the attachment site.

[0013] According to the second aspect of the present application, a mixture is provided, which contains at least one organic compound as described above and at least one organic functional material, and the organic functional material is selected from at least one of hole injection materials, hole transport materials, luminescence auxiliary materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, organic light-emitting guest materials and organic host materials.

[0014] According to the third aspect of the present application, a composition is further provided, comprising an organic solvent and at least one of the organic compounds described above, or comprising the organic solvent and the mixture described above.

[0015] According to a fourth aspect of the present application, an organic light-emitting device is further provided, comprising:

[0016] a first electrode;

[0017] an organic functional layer, disposed on one side of the first electrode;

[0018] a second electrode, disposed on a side of the organic functional layer away from the first electrode;

[0019] The material of the organic functional layer includes at least one of the organic compounds or the mixtures mentioned above, or the organic functional layer is made from the composition mentioned above.

[0020] According to a fifth aspect of the present application, a display panel is further provided, comprising the organic light-emitting device described above.

[0021] In the organic compounds, mixtures, compositions, organic light-emitting devices, and display panels of the embodiments of the present application, the organic compound is a triarylamine compound constructed by combining an adamantyl group, a naphthyl group, and a phenyl-substituted benzodibenzofuran group. This organic compound has excellent hole transport capabilities and has significant advantages as a hole-assisted transport material in organic light-emitting devices, helping to regulate charge balance. The introduction of the adamantyl group helps to increase the glass transition temperature of the organic compound. When this organic compound is used as a light-assisted material in an organic light-emitting device, it can significantly improve the luminous efficiency and service life of the organic light-emitting device while maintaining a low driving voltage for the organic light-emitting device.

[0022] Other features and advantages of the present application will be described in detail in the subsequent detailed description. BRIEF DESCRIPTION OF THE DRAWINGS

[0023] To more clearly illustrate the technical solutions in the embodiments of the present application, the following briefly introduces the drawings required for describing the embodiments. Obviously, the drawings described below are only some embodiments of the present application. Those skilled in the art can also derive other drawings based on these drawings without inventive effort.

[0024] In order to more completely understand the present application and its beneficial effects, the following description will be given in conjunction with the accompanying drawings, wherein the same drawing numbers represent the same parts in the following description.

[0025] Figure 1 This is a schematic structural diagram of an organic light-emitting device provided in an embodiment of the present application.

[0026] Figure numerals: 100, organic light-emitting device; 1, substrate; 11, first electrode; 12, hole injection layer; 13, hole transport layer; 14, light-emitting auxiliary layer; 15, organic light-emitting layer; 16, electron transport layer; 17, electron injection layer; 18, second electrode. DETAILED DESCRIPTION

[0027] The technical solutions in the embodiments of the present application will be described clearly and completely below in conjunction with the drawings in the embodiments of the present application.

[0028] In the present application, "substituted" means that a hydrogen atom in a substituted group is replaced by a substituent.

[0029] In this application, hydrogen atoms include isotopes having different numbers of neutrons, namely protium, deuterium and tritium.

[0030] In the present application, "substituted or unsubstituted" means that the defined group may be substituted or unsubstituted. When the defined group is substituted, it should be understood that it is optionally substituted by the groups defined in the present application.

[0031] In this application, "*" connected to a single bond indicates a connection or fusion site.

[0032] In the present application, when a linking site is not specified in a group, it means that an optional linking site in the group can be used as the linking site.

[0033] In the present application, the single bond to which the substituent is connected runs through the corresponding ring, indicating that the substituent can be attached to any position of the ring, for example R is connected to any substitutable position of the benzene ring.

[0034] The present invention provides an organic compound, the general structural formula of which is shown in Formula (1):

[0035]

[0036] wherein X is selected from an oxygen atom or a sulfur atom;

[0037] L1 and L2 are selected from any one or more combinations of a single bond, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted dibenzothiophenyl group; the substituent group in the substituted or unsubstituted group is selected from a deuterium atom or a phenyl group;

[0038] Ar1 is selected from a hydrogen atom or any one of the following groups, and Ar2 is selected from a single bond or any one of the following groups:

[0039]

[0040]

[0041] “*” indicates the attachment site.

[0042] It can be understood that the above expression of “—” crossing a structure indicates that the connection site is any position on the structure that can form a bond.

[0043] In some embodiments, the general structural formula of the organic compound is as shown in Formula (1-1) or Formula (1-2):

[0044]

[0045] In some embodiments, L1 and L2 are selected from any one of a single bond, a phenyl group which is substituted or unsubstituted with a deuterium atom, an unsubstituted biphenyl group, an unsubstituted naphthyl group, an unsubstituted fluorenyl group, and an unsubstituted dibenzofuranyl group.

[0046] In a specific embodiment, the organic compound is selected from any one of the following compounds:

[0047]

[0048]

[0049]

[0050]

[0051]

[0052]

[0053]

[0054]

[0055]

[0056]

[0057]

[0058]

[0059]

[0060]

[0061]

[0062] In some embodiments, the above-mentioned organic compounds provided in the embodiments of the present application can be used as organic functional materials in electronic devices, in particular in OLED devices. Organic functional materials can be divided into hole injection materials (HIM), hole transport materials (HTM), luminescent auxiliary materials (Prime), electron transport materials (ETM), electron injection materials (EIM), electron blocking materials (EBM), hole blocking materials (HBM), luminescent guest materials (Guest Emitter) and host materials (Host Emitter). Among them, the host material can be divided into phosphorescent host materials, fluorescent host materials and host materials of thermally activated delayed fluorescence (TADF) luminescent materials. The above-mentioned organic compounds provided in the embodiments of the present application can be used as any one of them.

[0063] In a preferred embodiment, the organic compound represented by the above formula (1) provided in the embodiment of the present application can be used as a light-emitting auxiliary material.

[0064] In some embodiments, the glass transition temperature of the organic compound provided in the embodiments of the present application is Tg ≥ 100°C; in a preferred embodiment, Tg ≥ 120°C; in a more preferred embodiment, Tg ≥ 140°C; in a more preferred embodiment, Tg ≥ 160°C; in a most preferred embodiment, Tg ≥ 180°C.

[0065] The embodiment of the present application also provides a polymer, wherein the monomer of the polymer includes an organic compound represented by formula (1).

[0066] The present application also provides a mixture comprising at least one organic compound represented by formula (1) and at least one organic functional material, wherein the organic functional material is selected from at least one of a hole injection material, a hole transport material, a luminescence auxiliary material, an electron transport material, an electron injection material, an electron blocking material, a hole blocking material, an organic luminescent guest material, and an organic host material. For example, various organic functional materials are described in detail in WO2010135519A1, US20090134784A1, and WO2011110277A1. The entire contents of these three patent documents are hereby incorporated herein by reference. The organic functional material can be a small molecule or a polymer material.

[0067] The organic compounds provided in the embodiments of the present application can be used in vapor-deposition OLED devices. For example, in some embodiments, the molecular weight of the organic compounds provided in the embodiments of the present application is ≤1100 g / mol; in a preferred embodiment, the molecular weight of the organic compounds provided in the embodiments of the present application is ≤1000 g / mol; in a more preferred embodiment, the molecular weight of the organic compounds provided in the embodiments of the present application is ≤950 g / mol; in a more preferred embodiment, the molecular weight of the organic compounds provided in the embodiments of the present application is ≤900 g / mol; and in a most preferred embodiment, the molecular weight of the organic compounds provided in the embodiments of the present application is ≤800 g / mol.

[0068] The organic compounds provided in the embodiments of this application can also be used in printed OLED devices. For example, in some embodiments, the molecular weight of the organic compounds provided in the embodiments of this application is ≥700 g / mol; in a more preferred embodiment, the molecular weight of the organic compounds provided in the embodiments of this application is ≥900 g / mol; in an even more preferred embodiment, the molecular weight of the organic compounds provided in the embodiments of this application is ≥1000 g / mol; and in a most preferred embodiment, the molecular weight of the organic compounds provided in the embodiments of this application is ≥1100 g / mol.

[0069] An embodiment of the present application also provides a composition, which comprises at least one organic solvent and at least one organic compound represented by formula (1), or the composition comprises at least one organic solvent and the mixture.

[0070] The organic solvent may be selected from any one or a mixture of two or more solvents selected from aromatic or heteroaromatic compounds, esters, aromatic ketones or aromatic ethers, aliphatic ketones or aliphatic ethers, alicyclic or olefinic compounds, borate esters or phosphate esters. Preferably, the organic solvent is selected from aromatic or heteroaromatic solvents.

[0071] Examples of aromatic or heteroaromatic solvents suitable for the present application include, but are not limited to: p-diisopropylbenzene, pentylbenzene, tetralin, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, dipentylbenzene, tripentylbenzene, pentyltoluene, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, 1,2,3,4-tetramethylbenzene, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, butylbenzene, dodecylbenzene, dihexylbenzene, dibutylbenzene, p-diisopropylbenzene, cyclohexylbenzene, benzylbutylbenzene, dimethylnaphthalene, 3-Isopropylbiphenyl, p-methylisopropylbenzene, 1-methylnaphthalene, 1,2,4-trichlorobenzene, 4,4-difluorodiphenylmethane, 1,2-dimethoxy-4-(1-propenyl)benzene, diphenylmethane, 2-phenylpyridine, 3-phenylpyridine, N-methyldiphenylamine, 4-isopropylbiphenyl, α,α-dichlorodiphenylmethane, 4-(3-phenylpropyl)pyridine, benzyl benzoate, 1,1-bis(3,4-dimethylphenyl)ethane, 2-isopropylnaphthalene, quinoline, isoquinoline, methyl 2-furoate, ethyl 2-furoate, etc.

[0072] Examples of aromatic ketone-based solvents suitable for the present application include, but are not limited to: 1-tetralone, 2-tetralone, 2-(phenylepoxy)tetralone, 6-(methoxy)tetralone, acetophenone, propiophenone, benzophenone and their derivatives, such as 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylpropiophenone, 3-methylpropiophenone, 2-methylpropiophenone, etc.

[0073] Examples of aromatic ether solvents suitable for the present application include, but are not limited to: 3-phenoxytoluene, butoxybenzene, p-anisaldehyde dimethyl acetal, tetrahydro-2-phenoxy-2H-pyran, 1,2-dimethoxy-4-(1-propenyl)benzene, 1,4-benzodioxane, 1,3-dipropylbenzene, 2,5-dimethoxytoluene, 4-ethyl acetate, 1,3-dipropoxybenzene, 1,2,4-trimethoxybenzene, 4-(1-propenyl)-1,2-dimethoxybenzene, 1,3-dimethoxybenzene, glycidyl phenyl ether, dibenzyl ether, 4-tert-butylanisole, trans-p-propenylanisole, 1,2-dimethoxybenzene, 1-methoxynaphthalene, diphenyl ether, 2-phenoxymethyl ether, 2-phenoxytetrahydrofuran, ethyl-2-naphthyl ether, and the like.

[0074] Examples of aliphatic ketone or aliphatic ether solvents suitable for the present application include, but are not limited to: 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2,5-hexanedione, 2,6,8-trimethyl-4-nonanone, fenchone, phorone, isophorone, di-n-amyl ketone, amyl ether, hexyl ether, dioctyl ether, ethylene glycol dibutyl ether, diethylene glycol diethyl ether, diethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, triethylene glycol ethyl methyl ether, triethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, etc.

[0075] Examples of borate or phosphate ester solvents suitable for the present application include, but are not limited to, alkyl octanoates, alkyl sebacates, alkyl stearates, alkyl benzoates, alkyl phenylacetates, alkyl cinnamates, alkyl oxalates, alkyl maleates, alkyl lactones, alkyl oleates, etc. Octyl octanoate, diethyl sebacate, diallyl phthalate, and isononyl isononanoate are particularly preferred.

[0076] In some preferred embodiments, the composition provided in the embodiments of the present application comprises at least one organic compound or polymer or mixture as described above, at least one organic solvent and at least one cosolvent. Examples of the cosolvent include (but are not limited to): methanol, ethanol, 2-methoxyethanol, dichloromethane, chloroform, chlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1,4-dioxane, acetone, methyl ethyl ketone, 1,2-dichloroethane, 3-phenoxytoluene, 1,1,1-trichloroethane, 1,1,2,2-tetrachloroethane, ethyl acetate, butyl acetate, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, tetralin, decalin, indene and / or mixtures thereof.

[0077] In some embodiments, solvents particularly suitable for the present application are solvents having a Hansen solubility parameter within the following range: δd (dispersion force) between 17.0 and 23.2 MPa. 1 / 2 range, especially in the range of 18.5~21.0MPa 1 / 2 range; δp (polar force) is 0.2~12.5MPa 1 / 2 range, especially in the range of 2.0~6.0MPa 1 / 2 range; δh (hydrogen bond force) is 0.9~14.2MPa 1 / 2 range, especially in the range of 2.0~6.0MPa 1 / 2 range.

[0078] In the compositions provided in the examples of this application, the boiling point parameters of the organic solvent should be considered when selecting. In this application, the boiling point of the organic solvent is ≥150°C; preferably, the boiling point of the organic solvent is ≥180°C; more preferably, the boiling point of the organic solvent is ≥200°C; more preferably, the boiling point of the organic solvent is ≥250°C; most preferably, the boiling point of the organic solvent is ≥275°C or ≥300°C. Boiling points within these ranges are beneficial for preventing clogging of the nozzles of the inkjet print head. The organic solvent can evaporate from the solvent system to form a film containing the organic functional material.

[0079] In some embodiments, the composition provided in the examples of the present application is a solution. In another embodiment, the composition provided in the examples of the present application is a suspension.

[0080] The compositions provided in the embodiments of the present application may include 0.01 wt % to 10 wt % of the organic compound or the mixture. Preferably, the mass fraction of the organic compound or the mixture in the composition ranges from 0.1 wt % to 15 wt %. More preferably, the mass fraction of the organic compound or the mixture in the composition ranges from 0.2 wt % to 5 wt %. Most preferably, the mass fraction of the organic compound or the mixture in the composition ranges from 0.25 wt % to 3 wt %.

[0081] In some embodiments, the mass fraction of the organic compound or the mixture in the composition is 0.01%, 0.05%, 0.1%, 0.15%, 0.2%, 0.25%, 0.3%, 0.35%, 0.4%, 0.45%, 0.5%, 0.6%, 0.7%, 0.8%, 0.9%, 1%, 3%, 5%, 8%, 10%, 12% or 15%.

[0082] The present application also provides an embodiment of the use of the composition as a coating or printing ink in the preparation of an organic electronic device. A particularly preferred use is to use the composition as a coating or printing ink and prepare an organic electronic device by a printing or coating preparation method.

[0083] Suitable printing or coating techniques include, but are not limited to, inkjet printing, nozzle printing, letterpress printing, screen printing, dip coating, spin coating, blade coating, roller printing, twist roller printing, lithographic printing, flexographic printing, rotary printing, spray coating, brush coating, pad printing, and slot extrusion coating. Gravure printing, nozzle printing, and inkjet printing are preferred. The solution or suspension may further include one or more components, such as surfactants, lubricants, wetting agents, dispersants, hydrophobic agents, and adhesives, to adjust viscosity, film-forming properties, and enhance adhesion. Relevant printing techniques and their associated requirements for the relevant solutions, such as solvent, concentration, and viscosity, are discussed in detail.

[0084] The organic compound, the mixture or the composition provided in this application can be applied in organic electronic devices.

[0085] The organic electronic devices include, but are not limited to, organic light-emitting diodes (OLEDs), organic photovoltaic cells (OPVs), organic light-emitting cells (OLEECs), organic field-effect transistors (OFETs), organic light-emitting field-effect transistors (OLEFETs), organic lasers, organic spintronic devices, organic sensors, and organic plasmon emitting diodes (OPEDs). Particularly preferably, the organic electronic device is an organic electroluminescent device, such as an OLED, an OLEEC, or an OLEFET.

[0086] In the embodiment of the present application, the organic compound is preferably applied to the light-emitting auxiliary layer of an OLED device.

[0087] like Figure 1 As shown, an embodiment of the present application further provides an organic light-emitting device 100, which is an organic electronic device, and the organic light-emitting device 100 includes a first electrode 11, a second electrode 18 arranged opposite to the first electrode 11, and an organic functional layer located between the first electrode 11 and the second electrode 18, wherein the material of the organic functional layer includes at least one of the organic compounds represented by the above formula (1), or the material of the organic functional layer includes the mixture described above, or the organic functional layer is prepared by using the organic compound, mixture or composition described above.

[0088] In one embodiment, the first electrode 11 is an anode, and the second electrode 18 is a cathode.

[0089] Specifically, the organic functional layer is selected from at least one of a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, a luminescence auxiliary layer, and an organic light-emitting layer. Preferably, the organic functional layer comprises at least a stacked luminescence auxiliary layer and an organic light-emitting layer.

[0090] Specifically, the organic light-emitting device 100 further includes a substrate 1 , and the first electrode 11 is disposed on the substrate 1 .

[0091] In one embodiment, the organic functional layer includes a hole injection layer 12, a hole transport layer 13, a luminescence auxiliary layer 14, an organic light-emitting layer 15, an electron transport layer 16, and an electron injection layer 17, which are sequentially stacked on the first electrode 11. The material of the luminescence auxiliary layer 14 includes at least one organic compound represented by formula (1).

[0092] In some embodiments, the organic light-emitting device 100 includes any one of a red organic light-emitting device, a blue organic light-emitting device, and a green organic light-emitting device. In other words, the organic compound represented by formula (1) provided in the embodiments of the present application can be used as a red light-emitting auxiliary material, a blue light-emitting auxiliary material, and a green light-emitting auxiliary material.

[0093] It can be understood that the red organic light emitting device emits red light, the blue organic light emitting device emits blue light, and the green organic light emitting device emits green light.

[0094] In a preferred embodiment, the organic compound represented by formula (1) is a blue light emitting auxiliary material. Therefore, the organic compound represented by formula (1) can be used in a blue light organic light emitting device.

[0095] Specifically, the organic light-emitting device 100 includes but is not limited to an organic light-emitting diode (OLED), an organic photovoltaic cell (OPV), an organic light-emitting cell (OLEEC), an organic field-effect transistor (OFET), an organic light-emitting field-effect transistor (OLEFET), an organic laser, an organic spintronic device, an organic sensor, and an organic plasmon emission diode (OPED), etc., and particularly preferred are organic electroluminescent devices such as OLED, OLEEC, or OLEFET.

[0096] The anode may comprise a conductive metal or metal oxide, or a conductive polymer. The anode can readily inject holes into the hole injection layer (HIL) or hole transport layer (HTL) or light-emitting layer. In some embodiments, the absolute value of the difference between the work function of the anode and the HOMO energy level or valence band energy level of the light-emitting material in the light-emitting layer or the p-type semiconductor material serving as the HIL or HTL or electron blocking layer (EBL) is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. Examples of anode materials include, but are not limited to, Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO, aluminum-doped zinc oxide (AZO), and the like. Other suitable anode materials are known and can be readily selected for use by one of ordinary skill in the art. The anode material can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), and the like. In certain embodiments, the anode is patterned. Patterned ITO conductive substrates are commercially available and can be used to prepare devices according to the present application.

[0097] The cathode may comprise a conductive metal or metal oxide. The cathode can readily inject electrons into the EIL or ETL or directly into the light-emitting layer. In some embodiments, the absolute value of the difference between the work function of the cathode and the LUMO energy level or conduction band energy level of the light-emitting body in the light-emitting layer or the n-type semiconductor material serving as the electron injection layer (EIL) or electron transport layer (ETL) or hole blocking layer (HBL) is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. In principle, all materials that can be used as cathodes for OLEDs may be used as cathode materials for the devices of the present application. Examples of cathode materials include, but are not limited to, Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloy, BaF2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO, and the like. The cathode material may be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), and the like.

[0098] In some embodiments, the light-emitting material in the light-emitting layer of the organic light-emitting device 100 provided in the embodiments of the present application is selected from a singlet light-emitting body, a triplet light-emitting body or a TADF material.

[0099] In some embodiments, the thickness of the organic functional layer in the organic light-emitting device 100 provided in the embodiments of the present application ranges from 10 nm to 200 nm, preferably from 20 nm to 150 nm, more preferably from 30 nm to 100 nm, and most preferably from 40 nm to 90 nm.

[0100] The organic light-emitting device 100 provided in the embodiment of the present application can be applied to various electronic devices, including but not limited to display devices, lighting devices, light sources, sensors, etc.

[0101] An embodiment of the present application further provides an electronic device, which includes the organic electronic device 100 provided in an embodiment of the present application. The electronic device includes but is not limited to a display device, a lighting device, a light source, a sensor, and the like.

[0102] An embodiment of the present application further provides a display panel, which includes the organic light-emitting device 100 described above.

[0103] The present application will be described below in conjunction with preferred embodiments, but the scope of protection of the present application is not limited to the following embodiments. It should be understood that the attached claims summarize the scope of protection of the present application. Under the guidance of the concept of the present invention, those skilled in the art should realize that certain changes made to the various embodiments of the present application will be covered by the spirit and scope of the claims of the present application.

[0104] (1) Specific Synthesis Example

[0105] The organic compounds and their preparation methods of the present invention are further described in detail below with reference to specific synthesis examples. Unless otherwise specified, the raw materials used in the following examples are all commercially available products.

[0106] (1) The synthetic route of intermediate A is as follows:

[0107]

[0108] Synthesis of intermediate b-1:

[0109] Compound a-1 (10 mmol), diboronic acid pinacol ester (20 mmol), Pd(dppf)3Cl2 (0.1 mmol), and potassium acetate (30 mmol) were dissolved in 1,4-dioxane, and the reaction solution was heated to 100°C and stirred for 6 hours under a nitrogen atmosphere; the reaction solution was cooled to room temperature, and a portion of the solvent was removed by rotary evaporation using a rotary evaporator, and then extracted three times with dichloromethane and water; after the extracted solution was separated, the organic phase was dried to obtain a crude product; the crude product was purified by column chromatography to obtain intermediate b-1 with a yield of 60-85%. The mass spectrometry result was m / z [H + ]=344.

[0110] Synthesis of intermediate A:

[0111] Intermediate b-1 (10 mmol), compound c (10 mmol), Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were dissolved in a mixed solvent of toluene, ethanol and water. The reaction solution was heated to 100°C and stirred for 6 hours under a nitrogen atmosphere. After the reaction, the reaction solution was cooled to room temperature, a portion of the solvent was removed by a rotary evaporator, and then extracted three times with dichloromethane and water. After the extracted solution was separated, the organic phase was dried to obtain a crude product. The crude product was purified by column chromatography to obtain intermediate A with a yield of 70-90%. The mass spectrum m / z [H + ]=378.

[0112] (2) The synthetic routes of intermediates B, C, and D are as follows:

[0113]

[0114] The synthesis process of intermediates b-2, b-3 and b-4 is the same as that of intermediate b-1, and the synthesis process of intermediates B, C, and D is the same as that of intermediate A. Only the reactants are different. Therefore, the synthesis process of intermediates b-2, b-3 and b-4 refers to the synthesis process of intermediate b-1, and the synthesis process of intermediates B, C, and D refers to the synthesis process of intermediate A, which will not be repeated here.

[0115] It can be understood that the difference between reactants a-1, a-2, a-3 and a-4 lies in the different connection sites between the Br atom and the benzene ring, the difference between intermediates b-1, b-2, b-3 and b-4 lies in the different connection sites between the boronic acid pinacol ester group and the benzene ring, and the difference between intermediates A, B, C and D lies in the different connection sites between the monochloro-substituted naphthyl group and the benzene ring.

[0116] (3) The synthetic route of intermediates E to H is as follows:

[0117]

[0118] The synthesis processes of intermediates E to H can refer to the synthesis processes of intermediates A to D, respectively, and will not be repeated here.

[0119] It can be understood that the difference between intermediates E, F, G and H lies in the different connection points of the monochloro-substituted naphthyl group and the benzene ring.

[0120] (4) The synthetic routes of intermediates I and J are as follows:

[0121]

[0122] The synthesis process of intermediates I and J can refer to the synthesis process of intermediate A, which will not be repeated here.

[0123] Example 1

[0124] The synthetic route of organic compound M1 is as follows:

[0125]

[0126] Synthesis of organic compound M1:

[0127] Intermediate A (10 mmol), compound 2-1 (10 mmol), Pd2(dba)3 (0.1 mmol), X-Phos (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, and the reaction solution was heated to 100°C and stirred for 6 h under a nitrogen atmosphere. After the reaction, the reaction solution was cooled to room temperature and a portion of the solvent was removed by rotary evaporation using a rotary evaporator. Then, the reaction solution was extracted three times with dichloromethane and water. The organic phase was dried to obtain a crude product. The crude product was further purified by column chromatography to obtain an organic compound M1 with a yield of 83%. The mass spectrometry result was m / z [H + ]=721, elemental analysis test values ​​are C, 89.87; H, 6.10; N, 1.91; O, 2.18.

[0128] Examples 2 to 23 were prepared using the same method as Example 1 to obtain organic compounds M2 to M23. Therefore, the synthesis process of organic compounds M2 to M23 can be referenced to the synthesis process of organic compound M1 and is not further described here. The structural formulas of the organic compounds, intermediates, and compounds corresponding to Examples 2 to 23, as well as the yields and structural characterization data of the products, are reported in Table 1.

[0129] Table 1

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137] The synthetic route of compound 2-9 in Example 9 is as follows:

[0138]

[0139] Specifically, since the synthesis of compound 2-9 and the synthesis of organic compound M1 are both carbon-nitrogen coupling reactions, the reaction mechanism and synthesis process of the two are the same, so the synthesis process of compound 2-9 can refer to the synthesis process of organic compound M1, which will not be repeated here. The yield of the product obtained by preparing compound 2-9 with reference to the synthesis process of organic compound M1 is 85%, and the mass spectrometry results do not show m / z [H + ]=479.

[0140] The synthetic route of compound 2-12 in Example 21 is as follows:

[0141]

[0142] Specifically, since the synthesis of compound 2-12 and the synthesis of organic compound M1 are both carbon-nitrogen coupling reactions, the reaction mechanism and synthesis process of the two are the same, so the synthesis process of compound 2-12 can refer to the synthesis process of organic compound M1, which will not be repeated here. The yield of the product obtained by preparing compound 2-12 with reference to the synthesis process of organic compound M1 is 81%, and the mass spectrum result is m / z [H + ]=443.

[0143] The synthetic route of compound 2-13 in Example 22 is as follows:

[0144]

[0145] Specifically, since the synthesis of compound 2-13 and the synthesis of organic compound M1 are both carbon-nitrogen coupling reactions, the reaction mechanism and synthesis process of the two are the same, so the synthesis process of compound 2-13 can refer to the synthesis process of organic compound M1, which will not be repeated here. The yield of the product obtained by preparing compound 2-13 with reference to the synthesis process of organic compound M1 is 83%, and the mass spectrum result is m / z [H + ]=417.

[0146] The synthetic route of compound 2-14 in Example 23 is as follows:

[0147]

[0148] Specifically, since the synthesis of compound 2-14 and the synthesis of organic compound M1 are both carbon-nitrogen coupling reactions, the reaction mechanism and synthesis process of the two are the same, so the synthesis process of compound 2-14 can refer to the synthesis process of organic compound M1, which will not be repeated here. The yield of the product obtained by preparing compound 2-14 with reference to the synthesis process of organic compound M1 is 85%, and the mass spectrum result is m / z [H + ]=433.

[0149] Comparative Example

[0150] This application also provides Comparative Example 1 and Comparative Example 2. The comparative compounds provided in Comparative Example 1 and Comparative Example 2 are respectively denoted as "Ref-01" and "Ref-02", and their chemical structures are shown below:

[0151]

[0152] (2) Glass transition temperature test

[0153] The organic compounds M1 to M23 provided in the examples of the present application and the comparative compounds Ref-01 and Ref-02 provided in the comparative examples were tested using a thermogravimetric analyzer (TGA) and a differential scanning calorimeter (DSC) to determine their glass transition temperatures (Tg). The test results are shown in Table 2.

[0154] Table 2

[0155] Material Tg(℃) Material Tg(℃) Organic compound M1 127 Organic Compound M14 129 Organic compound M2 129 Organic Compound M15 128 Organic Compound M3 131 Organic Compound M16 131 Organic Compound M4 130 Organic Compound M17 129 Organic Compound M5 128 Organic Compound M18 131 Organic Compound M6 128 Organic Compound M19 128 Organic Compound M7 126 Organic Compound M20 129 Organic Compound M8 129 Organic Compound M21 133 Organic Compound M9 132 Organic Compound M22 131 Organic Compound M10 133 Organic Compound M23 128 Organic Compound M11 128 Comparative compound Ref-01 115 Organic Compound M12 128 Comparative compound Ref-02 117 Organic Compound M13 132

[0156] As shown in Table 2, the introduction of adamantyl and benzene-substituted benzodibenzofuran groups in the organic compounds M1 to M23 provided in the Examples of the present application results in higher glass transition temperatures (Tg) compared to the comparative compounds Ref-01 and Ref-02. When any one or more of the organic compounds M1 to M23 are used in the preparation of organic light-emitting devices, their higher Tg values ​​help enhance the stability and durability of the devices during use, significantly improving their service life.

[0157] (3) Preparation and performance characterization of OLED devices

[0158] The following detailed description of the method and process for preparing OLED devices using the organic compounds of this application is provided through specific device examples. In the following method for preparing OLED devices, ITO conductive glass is used as the anode substrate, PD is used as the hole injection material, HT is used as the hole transport material, BH is used as the host material of the light-emitting layer, BD is used as the dopant material of the light-emitting layer, ET and Liq are used as electron transport materials, Liq is used as the electron injection material, and Al is used as the cathode material. In addition, organic compounds M1 to M23 from the aforementioned synthesis examples are used as auxiliary luminescent materials to prepare corresponding OLED devices. The chemical structures of PD, HT, BH, BD, ET, and Liq are shown below:

[0159]

[0160] The following describes in detail the preparation process of an OLED device using the above-mentioned materials through a specific embodiment. Taking the preparation method of an OLED device using organic compound M1 as the auxiliary luminescent material as an example, the resulting OLED device is referred to as "OLED-1 device." In this embodiment, the structure of the OLED-1 device is: ITO / PD:HT (3:97, 10nm) / HT (130nm) / organic compound M1 (90nm) / BH:BD (3%, 40nm) / ET:Liq (5:5, 30nm) / Liq (1nm) / Al (100nm). The preparation method of the OLED-1 device includes steps a through c.

[0161] a. Cleaning of ITO conductive glass: Use chloroform, ketone, and isopropyl alcohol for cleaning, and then perform UV ozone plasma treatment.

[0162] b. Preparation of organic functional layer: First, ITO conductive glass was moved into vacuum vapor deposition equipment and placed in high vacuum (1×10 -6 mbar), using resistance heating evaporation to The hole injection materials PD and HT were evaporated on the ITO conductive glass at an evaporation rate of 3:97 to obtain a hole injection layer with a thickness of 10 nm. The hole transport material HT was evaporated on the hole injection layer at a deposition rate of 100 nm to obtain a hole transport layer with a thickness of 130 nm. The organic compound M1 provided in the above embodiment was evaporated on the hole transport layer at a deposition rate of 100 nm to obtain a light-emitting auxiliary layer with a thickness of 90 nm; BH and BD were evaporated on the light-emitting auxiliary layer at a rate of 97:3, and a light-emitting layer with a thickness of 40 nm was obtained. Subsequently, the electron transport materials ET and Liq were placed in different evaporation crucibles in a vacuum chamber and heated in a high vacuum environment (1×10 -6 ET and Liq were co-deposited at a weight ratio of 5:5 under 30 mbar to form an electron transport layer with a thickness of 30 nm on the light-emitting layer; The electron injection material Liq was evaporated on the electron transport layer at a deposition rate of 1 nm to obtain an electron injection layer with a thickness of 1 nm; The cathode material Al was evaporated on the electron injection layer at an evaporation rate of to obtain a cathode with a thickness of 100 nm.

[0163] c. Encapsulation: The device was placed in a nitrogen glove box and encapsulated with UV-curable resin to obtain the OLED-1 device.

[0164] Referring to the preparation method for OLED-1, organic compounds M2 through M23 provided in the aforementioned synthesis examples were selected as auxiliary luminescent materials for the OLED devices, respectively, to produce OLED-2 through OLED-23 devices. It will be appreciated that, in the preparation methods for OLED-1 through OLED-23, other experimental conditions were identical, except for the auxiliary luminescent materials.

[0165] Referring to the preparation method of the OLED-1 device example, comparative compounds Ref-01 and Ref-02 were used as luminescence-assisting materials in the OLED device to prepare OLED-Ref-01 and OLED-Ref-02 devices, respectively. It can be understood that, compared to the preparation method of the OLED-1 device, the preparation methods of the OLED-Ref-01 and OLED-Ref-02 devices, except for the different luminescence-assisting materials, all other experimental conditions were identical.

[0166] In this application, the current-voltage (JV) characteristics of OLED-1 to OLED-23 devices, OLED-Ref-01 and OLED-Ref-02 devices were characterized, and important parameters such as luminous efficiency and service life were recorded. The results are shown in Table 3. Among them, the luminous efficiency is the current density of 10mA·cm -2 The service life (LT95) is the value obtained when the current density is 10mA·cm -2 The time it takes for the brightness to drop to 95% of the initial brightness.

[0167] Table 3

[0168]

[0169]

[0170] As shown in Table 3, compared to the OLED-Ref-01 and OLED-Ref-02 devices, the OLED-1 to OLED-23 devices prepared using the organic compounds M1 to M23 provided in Examples 1 to 23 of this application as blue-light luminescence auxiliary materials, respectively, exhibited significant improvements in luminous efficiency and service life. Furthermore, the OLED-1 to OLED-23 devices can maintain a relatively low driving voltage. This demonstrates that the triarylamine-based blue-light luminescence auxiliary materials containing adamantyl and benzene-substituted benzodibenzofuran groups provided herein exhibit excellent overall performance and possess significant application prospects.

[0171] Therefore, the organic compound provided in the embodiments of the present application is a triarylamine compound constructed from an adamantyl group, a naphthyl group, and a phenyl-substituted benzodibenzofuran group. It has excellent hole transport capabilities and offers significant advantages as a hole-assisted transport material in organic light-emitting devices, helping to regulate charge balance. The introduction of the adamantyl group helps to increase the glass transition temperature of the organic compound. When used as a light-assisted material in an organic light-emitting device, this organic compound can significantly improve the luminous efficiency and service life of the organic light-emitting device while maintaining a low driving voltage.

[0172] In the description of this application, the terms "first" and "second" are used for descriptive purposes only and should not be understood to indicate or imply relative importance or implicitly specify the number of technical features indicated. Therefore, a feature defined as "first" or "second" may explicitly or implicitly include one or more features. In the description of this application, "plurality" means two or more, unless otherwise specifically defined.

[0173] In the above embodiments, the description of each embodiment has its own focus. For parts not described in detail in one embodiment, please refer to the relevant description of other embodiments. The embodiments, implementation methods and related technical features of this application can be combined and replaced with each other without conflict.

[0174] The above are merely preferred embodiments of the present application and do not constitute any form of limitation to the present application. However, any simple modifications, equivalent changes, and modifications made to the above embodiments based on the technical essence of the present application without departing from the content of the technical solution of the present application are still within the scope of the technical solution of the present application.

Claims

1. An organic compound, characterized in that The general structural formula of the organic compound is shown in formula (1): wherein X is selected from an oxygen atom or a sulfur atom; L1 and L2 are selected from any one or more combinations of a single bond, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted dibenzothiophenyl group; the substituent group in the substituted or unsubstituted group is selected from a deuterium atom or a phenyl group; Ar1 is selected from a hydrogen atom or any one of the following groups, and Ar2 is selected from a single bond or any one of the following groups: "*" indicates the attachment site.

2. The organic compound according to claim 1, characterized in that The general structural formula of the organic compound is shown in Formula (1-1) or Formula (1-2):

3. The organic compound according to claim 1 or 2, characterized in that L1 and L2 are selected from any one of a single bond, a phenyl group which may be substituted by a deuterium atom, an unsubstituted biphenyl group, an unsubstituted naphthyl group, an unsubstituted fluorenyl group, and an unsubstituted dibenzofuranyl group.

4. The organic compound according to claim 1, characterized in that The organic compound is selected from any one of the following compounds:

5. A mixture, characterized in that The mixture comprises at least one organic compound according to any one of claims 1 to 4 and at least one organic functional material, wherein the organic functional material is selected from at least one of a hole injection material, a hole transport material, a luminescence auxiliary material, an electron transport material, an electron injection material, an electron blocking material, a hole blocking material, an organic light-emitting guest material and an organic host material.

6. A composition, characterized in that The composition comprises an organic solvent and at least one organic compound according to any one of claims 1 to 4 , or the composition comprises the organic solvent and the mixture according to claim 5 .

7. An organic light-emitting device, characterized in that: The organic light emitting device comprises: a first electrode; an organic functional layer, disposed on one side of the first electrode; a second electrode, disposed on a side of the organic functional layer away from the first electrode; The material of the organic functional layer includes at least one organic compound according to any one of claims 1 to 4 or the mixture according to claim 5, or the organic functional layer is made from the composition according to claim 6.

8. The organic light-emitting device according to claim 7, characterized in that: The organic functional layer includes a light-emitting auxiliary layer and an organic light-emitting layer that are stacked, and the material of the light-emitting auxiliary layer includes at least one of the organic compounds.

9. The organic light-emitting device according to claim 8, characterized in that: The organic light emitting device emits blue light.

10. A display panel, characterized in that: An organic light-emitting device comprising the organic light-emitting device according to any one of claims 7 to 9.

Images