Organic compounds, mixtures, compositions, organic light emitting devices and display devices

Abstract

The present application relates to an organic compound, mixture, composition, organic light-emitting device and display device, the organic compound has the structure represented by general formula (1): (1); the organic compound of general formula (1) of the present application can be applied to organic light-emitting device as auxiliary hole transport material, can significantly improve the luminous efficiency and lifetime of organic light-emitting device, while maintaining a lower driving voltage.

Description

Technical Field

[0001] This application relates to the field of display technology, and more particularly to an organic compound, mixture, composition, organic light-emitting device, and display apparatus. Background Technology

[0002] Organic electroluminescence (OEL) technology utilizes the photoelectric properties of organic materials to directly convert electrical energy into light energy. OEL-based devices typically consist of an anode, a cathode, and multiple layers of organic functional layers. These layers include hole injection layers, hole transport layers, auxiliary functional layers, light-emitting layers, electron transport layers, and electron injection layers, each containing specific organic materials designed to enhance the overall performance of the device. When a voltage is applied between the electrodes, holes are injected into the anode, and electrons are injected into the cathode. These combine to form excitons, which release light energy as they return to their ground state. As a typical representative of OEL technology, organic light-emitting diodes (OLEDs) have achieved remarkable success in flat panel displays and lighting due to their self-emissive nature, high brightness, high efficiency, low voltage, wide viewing angle, and high contrast. Their wide viewing angle, fast response, low voltage requirements, 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 materials for the auxiliary functional layer play a crucial role in improving the luminous efficiency and extending the lifespan of OLED devices. Carefully designed auxiliary materials can effectively balance carrier transport in OLED devices, strongly suppress electron back migration, and promote electron-hole recombination primarily in the central region of the emissive layer, reducing non-radiative exciton recombination, thereby improving luminous efficiency and extending lifespan. Therefore, developing more efficient novel auxiliary materials to further optimize the balance of hole and electron transport within the device is a pressing issue for those skilled in the art, aimed at improving device efficiency and lifespan while maintaining a low driving voltage. Summary of the Invention

[0004] This application provides an organic compound, mixture, composition, organic light-emitting device, and display device. The organic compound can be used as an auxiliary hole transport material in the organic light-emitting device to improve the luminous efficiency and lifespan of the device while maintaining a low driving voltage.

[0005] A first aspect of this application provides an organic compound having the structure represented by general formula (1): General formula (1); in: Ar1 is selected from C1, whether substituted or unsubstituted. 6-15 Aromatic groups; L is selected from C, whether substituted or unsubstituted. 6-30 Aromatic groups, substituted or unsubstituted C 5-30 One or a combination of at least two of the heteroaromatic groups; Ar2 is selected from C that has been substituted or not substituted. 6-30 Aromatic groups, substituted or unsubstituted C 5-30 One or a combination of at least two of the heteroaromatic groups.

[0006] A second aspect of this application provides a mixture comprising at least one organic functional material and at least one organic compound as described above, wherein the organic functional material is selected from hole injection materials, hole transport materials, auxiliary hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, organic light-emitting guest materials, or organic host materials.

[0007] A third aspect of this application provides a composition comprising at least one organic solvent and at least one organic compound as described above, or the composition comprising at least one of the organic solvents and a mixture as described above.

[0008] A fourth aspect of this application provides an organic light-emitting device, the organic light-emitting device comprising: First electrode; The second electrode is disposed opposite to the first electrode; and An organic functional layer is located between the first electrode and the second electrode; The organic functional layer is made of at least one organic compound as described above, or the organic functional layer is made of a mixture as described above, or the organic functional layer is prepared from a composition as described above.

[0009] A fifth aspect of this application provides a display device comprising the organic light-emitting device described above.

[0010] This application provides an organic compound, mixture, composition, organic light-emitting device, and display device. The organic compound of this application is an aromatic amine compound constructed with benzo[a]carbazole and dibenzo[a]furan as its core components. Benzo[a]carbazole extends the conjugated plane through fused aromatic rings, exhibiting stronger molecular rigidity compared to ordinary carbazole. This rigid structure can suppress vibrational relaxation during nonradiative transitions, reduce molecular thermal motion, and improve material stability. Furthermore, the COC bond in dibenzo[a]furan has high bond energy, further ensuring molecular structural stability. Simultaneously, the oxygen-containing dibenzo[a]furan possesses a certain electron affinity, effectively blocking electron leakage from the light-emitting layer and reducing exciton quenching. Therefore, when this organic compound is used as an auxiliary hole transport material in an organic light-emitting device, it can significantly improve the luminous efficiency and lifespan of the device while maintaining a low driving voltage. Attached Figure Description

[0011] Figure 1 This is a schematic diagram of the structure of an organic light-emitting device provided in an embodiment of this application.

[0012] Explanation of reference numerals in the attached figures: 100 - Organic light-emitting device; 110 - Substrate; 120 - First electrode; 130 - Organic functional layer; 131 - Hole injection layer; 132 - Hole transport layer; 133 - Auxiliary hole transport layer; 134 - Light-emitting layer; 135 - Electron transport layer; 136 - Electron injection layer; 140 - Second electrode. Detailed Implementation

[0013] The technical solution of this application will be further described in detail below with reference to specific embodiments. This application can be implemented in many different forms and is not limited to the embodiments described herein. Rather, these embodiments are provided to provide a more thorough and complete understanding of the disclosure of this application.

[0014] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by those skilled in the art.

[0015] The term “and / or” as used in this application includes any and all combinations of one or more of the associated listed items.

[0016] In this application, hydrogen atoms include isotopes with different numbers of neutrons, namely protium, deuterium, and tritium.

[0017] In this application, "substitution" means that the hydrogen atom in the substituent is replaced by the substituent.

[0018] In this application, "substituted or unsubstituted" means that the defined group may or may not be substituted. When the defined group is substituted, it should be understood that it may be substituted by a group acceptable in the art, including but not limited to: deuterium atom, cyano, isocyano, nitro, halogen atom, C 1-10 alkyl, C 1-10 alkoxy, C 1-10 alkylthio group, C 6-30 aryl, C 6-30 aryloxy group, C 6-30 aryl thiols, C 3-30 heteroaryl, C 1-30 silane, C 2-10 alkylamine group, C 6-30 Aromatic amino groups, or combinations thereof, etc.

[0019] In this application, "alkyl" can mean straight-chain, branched, and / or cyclic alkyl. The number of carbon atoms in an alkyl group can be 1 to 15. Phrases containing this term, such as "C 1-9 "Alkyl" refers to an alkyl group containing 1 to 9 carbon atoms, and each time it appears, it can independently be C1 alkyl, C2 alkyl, C3 alkyl, C4 alkyl, C5 alkyl, C6 alkyl, C7 alkyl, C8 alkyl, or C9 alkyl. Non-limiting examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, adamantane, etc.

[0020] In this application, "aryl or aromatic group" refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removing one hydrogen atom. This group can be monocyclic aryl, fused-ring aryl, or polycyclic aryl; for polycyclic rings, at least one is an aromatic ring system. For example, "substituted or unsubstituted C..." 6~30 "Aryl group" refers to an aryl group containing 6 to 30 carbon atoms, with optional further substitutions; suitable examples include, but are not limited to: benzene, biphenyl, terphenyl, naphthalene, anthracene, fluoranthene, phenanthrene, benzo[a]phenanthrene, dinaphthalene-based phenylene, tetraphenyl, pyrene, benzo[a]pyrene, acenaphthene, fluorene, and their derivatives. Understandably, multiple aryl groups may also be interrupted by short non-aromatic units (e.g., <10% non-H atoms, such as C, N, or O atoms), specifically acenaphthene, fluorene, or 9,9-diarylfluorene, triarylamines, and diaryl ether systems should also be included in the definition of aryl.

[0021] In this application, the term "substituted or unsubstituted C" is used. 5~30"Heteroaromatic group" refers to a monovalent group comprising a carbocyclic heteroaromatic system having at least one heteroatom selected from nitrogen, oxygen, phosphorus, sulfur, or silicon as a cyclic atom and 5 to 30 carbon atoms. Non-limiting examples of heteroaromatic groups containing 5 to 30 carbon atoms may include furanyl, thiophene, pyrrole, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,3 Oxadiazolyl, 1,2,4 Oxadiazolyl, 1,3,4 Oxadiazolyl, 1,2,5 Oxadiazolyl, 1,2,3 Thiadiazolyl, 1,2,4 Thiadiazolyl, 1,3,4 Thiadiazolyl, 1,2,5 Thiadiazolyl, tetrazolyl, pyridinyl, pyrimidinyl, pyridazinyl, 1,2,3 Triazine, 1,2,4 Triazine, 1,3,5 Triazinyl, benzofuranyl, benzoisofuranyl, benzothiophenyl, benzoisothiophenyl, indoleyl, isoyindoleyl, indazoleyl, benzimidazolyl, benzoxazolyl, benzoisoxazolyl, benzothiazolyl, 2,1,3 Benzoxadiazole, quinolinyl, isoquinolinyl, terolinyl, phthalazinyl, quinazolinyl, quinolinyl, naphridinyl, benzotriazinyl, benzooxazinyl, purine, pteridinyl, indazinyl, benzothiazinyl, acridineyl, benazinyl, benazinyl, benazinyl, dibenzofuranyl, dibenzothiopheneyl, carbazoleyl, naphridinyl, quinolinyl, isoquinolinyl, indole [1,2] f]Phenyridyl, imidazo[2,1] a] Isoquinolinyl, imidazo[1,2] a] Quinolinyl, benzo[4,5]imidazo[1,2] a]pyridyl, imidazo[1,2] a]pyridyl, benzofuran [3,2] c] Quinolinyl, naphtho[1,2] b]Benzofuranyl, Naphtho[2,3] b] Benzofuranyl and other aromatic composite groups with heteroatoms, but not limited thereto.

[0022] In this application, the "linked to single key" "" indicates a connection or fusion site.

[0023] In this application, when no linking site is specified in the group, it means that any linkable site in the group is selected as the linking site.

[0024] In this application, the single bond connecting the substituents extends through the corresponding ring, indicating that the substituent can be attached to any position on the ring, for example... R is attached to any substituted site on the benzene ring.

[0025] This application provides an organic compound having the structure represented by general formula (1): General formula (1); in: Ar1 is selected from C1, whether substituted or unsubstituted. 6-15 Aromatic groups; L is selected from C, whether substituted or unsubstituted. 6-30 Aromatic groups, substituted or unsubstituted C 5-30 One or a combination of at least two of the heteroaromatic groups; Ar2 is selected from C that has been substituted or not substituted. 6-30 Aromatic groups, substituted or unsubstituted C 5-30 One or a combination of at least two of the heteroaromatic groups; The substituted or unsubstituted substituents mentioned above are selected from deuterium atoms, C atoms, and C atoms. 1-15 alkyl, C 6-30 Aromatic groups, C 5-30 One or a combination of at least two of the heteroaromatic groups; The heteroatoms in the aforementioned heteroaromatic groups are selected from one or more of nitrogen (N), oxygen (O), and sulfur (S); In general formula (1), the ring structure crossed by “—” indicates that the connection point is located at any position on the ring structure where bonding can occur.

[0026] In some embodiments, the substituted or unsubstituted substituents are selected from deuterium atoms, C atoms, and C atoms. 1-15 Alkyl, phenyl, biphenyl or naphthyl groups.

[0027] In some embodiments, Ar1 is selected from phenyl.

[0028] In some embodiments, L is selected from one or a combination of at least two of phenylene, biphenylene, naphthylene, fluorene, dibenzofuranyl, and dibenzothiopheneyl.

[0029] In some embodiments, Ar2 is selected from any of the following groups:

[0030]

[0031] ; in, Indicates the connection site.

[0032] In some embodiments, the organic compound is selected from any of the following structures, but is not limited to the following structures:

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[0070] .

[0071] In this application, the organic compound represented by general formula (1) is an aromatic amine compound constructed with benzo[carbazole] and dibenzo[furan] as the core. Benzo[carbazole] extends the conjugated plane through fused aromatic rings (such as benzene rings), and has stronger molecular rigidity than ordinary carbazole. This rigid structure can suppress the vibrational relaxation of molecules in nonradiative transitions, reduce molecular thermal motion, and improve the stability of the material. In addition, the COC bond in dibenzo[furan] has a high bond energy, which further ensures the stability of the molecular structure. At the same time, the oxygen-containing dibenzo[furan] has a certain electron affinity, which can effectively block electrons from leaking backward from the light-emitting layer and reduce exciton quenching. When this organic compound is used as an auxiliary hole transport material in organic light-emitting devices, it can significantly improve the luminous efficiency and lifespan of organic light-emitting devices while maintaining a low driving voltage.

[0072] In some embodiments, the organic compound can be used as an organic functional material in organic light-emitting devices, such as OLED organic light-emitting devices. The aforementioned organic functional material can be one or more of the following: hole injection material (HIM), hole transport material (HTM), auxiliary hole transport material, electron transport material (ETM), electron injection material (EIM), electron blocking material (EBM), hole blocking material (HBM), organic light-emitting guest material, or organic host material.

[0073] In some embodiments, the organic compound can be used as an auxiliary hole transport material in the auxiliary hole transport layer to improve hole transport efficiency, while effectively blocking electrons from leaking backward from the light-emitting layer and reducing exciton quenching, thereby improving the luminous efficiency and lifespan of the organic light-emitting device.

[0074] In some embodiments, the glass transition temperature (Tg) of the organic compound is greater than or equal to 100°C; preferably, Tg is greater than or equal to 120°C; more preferably, Tg is greater than or equal to 140°C; even more preferably, Tg is greater than or equal to 160°C; and most preferably, Tg is greater than or equal to 180°C.

[0075] This application also provides a mixture comprising at least one organic compound as described above, and at least one organic functional material. The organic functional material is selected from hole injection materials, hole transport materials, auxiliary hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, organic light-emitting guest materials, organic host materials, or inorganic quantum dot materials. 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.

[0076] In some embodiments, the organic compound may be used as an organic functional material for vapor-deposited OLEDs or as an organic functional material for printed OLEDs.

[0077] In some embodiments, when the organic compound is used as an organic functional material for vapor-deposited OLEDs, the molecular weight of the organic compound is less than or equal to 1100 g / mol, preferably less than or equal to 1000 g / mol, more preferably less than or equal to 950 g / mol, even more preferably less than or equal to 900 g / mol, and most preferably less than or equal to 800 g / mol.

[0078] In some embodiments, when the organic compound is used as an organic functional material for a printed OLED, the molecular weight of the organic compound is greater than or equal to 500 g / mol, preferably greater than or equal to 700 g / mol, more preferably greater than or equal to 900 g / mol, and most preferably greater than or equal to 1000 g / mol.

[0079] This application also provides a composition comprising at least one organic compound as described above and at least one organic solvent, or the composition comprising a mixture as described above and at least one organic solvent.

[0080] In some embodiments, the organic solvent may be any one of aromatic or heteroaromatic compounds, esters, aromatic ketones or aromatic ethers, aliphatic ketones or aliphatic ethers, alicyclic or olefinic compounds, or borate esters or phosphate esters, or a mixture of two or more solvents. Preferably, the organic solvent is selected from aromatic or heteroaromatic solvents.

[0081] In some embodiments, aromatic or heteroaromatic solvents include, but are not limited to: p-diisopropylbenzene, pentamene, tetrahydronaphthalene, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, dipentene, tripentene, pentamethylenetetramine, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, 1,2,3,4-tetramethylbenzene, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, butanediol, 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-furanoate, ethyl 2-furanoate, etc.

[0082] In some embodiments, the aromatic ketone-based solvents include, but are not limited to: 1-tetrahydronaphthone, 2-tetrahydronaphthone, 2-(phenylepoxy)tetrahydronaphthone, 6-(methoxy)tetrahydronaphthone, acetophenone, phenylacetone, benzophenone, and their derivatives, such as 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylphenylacetone, 3-methylphenylacetone, 2-methylphenylacetone, etc.

[0083] In some embodiments, the aromatic ether-based solvents 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-ethylbenzene, 1,3-dipropoxybenzene, 1,2,4-trimethoxybenzene, 4-(1-propenyl)-1,2-dimethoxybenzene, 1,3-dimethoxybenzene, glycidylphenyl 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, etc.

[0084] In some embodiments, solvents based on aliphatic ketones or aliphatic ethers include, but are not limited to: 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2,5-hexanedione, 2,6,8-trimethyl-4-nonanone, frankinc, forlone, isophorone, di-n-pentyl ketone, pentanyl ether, hexane 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.

[0085] In some embodiments, the solvent based on borate esters or phosphate esters includes, but is not limited to: alkyl octanoate, alkyl sebacate, alkyl stearate, alkyl benzoate, alkyl phenylacetate, alkyl cinnamate, alkyl oxalate, alkyl maleate, alkyl lactone, alkyl oleate, etc. Particularly preferred are octyl octanoate, diethyl sebacate, diallyl phthalate, and isononyl isononanoate.

[0086] In some embodiments, the composition further includes a co-solvent, which includes, but is not limited to, at least one of: methanol, ethanol, 2-methoxyethanol, dichloromethane, trichloromethane, 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, tetrahydronaphthalene, naphthane, and indene.

[0087] In some embodiments, the Hansen solubility parameter of the organic solvent is in the following range: δd (dispersion force) is 17.0~23.2 MPa. 1 / 2 The preferred range is 18.5~21.0 MPa. 1 / 2 The range; δp (polar force) is 0.2~12.5MPa. 1 / 2 The preferred range is 2.0~6.0 MPa. 1 / 2 The range; δh (hydrogen bond force) is 0.9~14.2 MPa. 1 / 2 The preferred range is 2.0~6.0 MPa. 1 / 2 The range.

[0088] In some embodiments, the boiling point of the organic solvent must be considered when selecting it. In this application, the boiling point of the organic solvent is greater than or equal to 150°C; preferably greater than or equal to 180°C; more preferably greater than or equal to 200°C; even more preferably greater than or equal to 250°C; most preferably greater than or equal to 275°C, or greater than or equal to 300°C. Having the boiling point of the organic solvent within the above range is beneficial in preventing nozzle clogging of the inkjet printhead.

[0089] It should be noted that the organic solvent can evaporate from the solvent system to form a thin film containing organic functional materials.

[0090] In some embodiments, the composition may be a solution.

[0091] In some embodiments, the composition may also be a suspension.

[0092] In some embodiments, the organic compound or the mixture in the composition is present in a mass percentage of 0.01 wt% to 15 wt%, preferably 0.1 wt% to 10 wt%, more preferably 0.2 wt% to 5 wt%, and most preferably 0.25 wt% to 3 wt%.

[0093] In some embodiments, the composition can be used as a coating or printing ink to prepare organic light-emitting devices, for example, by printing or coating methods.

[0094] The printing or coating methods include, but are not limited to: inkjet printing, nozzle printing, letterpress printing, screen printing, dip coating, spin coating, knife coating, roller printing, torsional roller printing, offset printing, flexographic printing, rotary printing, spraying, brushing or pad printing, slot extrusion coating, etc. Gravure printing, inkjet printing, and other similar methods are preferred.

[0095] Furthermore, the composition may also include one or more other components, such as surfactants, lubricants, wetting agents, dispersants, hydrophobic agents, adhesives, etc., to adjust viscosity, film-forming properties, and improve adhesion, etc., to meet the requirements of relevant printing technologies for the solutions, such as solvent, concentration, viscosity, etc.

[0096] This application also provides an organic light-emitting device 100, please refer to... Figure 1 The organic light-emitting device 100 includes: a first electrode 120, an organic functional layer 130, and a second electrode 140, wherein the organic functional layer 130 is located between the first electrode 120 and the second electrode 140; wherein the material of the organic functional layer 130 includes at least one organic compound as described above, or the material of the organic functional layer 130 includes a mixture as described above, or the organic functional layer 130 is prepared from a composition as described above.

[0097] In some embodiments, please refer to Figure 1 One of the first electrode 120 and the second electrode 140 is the anode, and the other is the cathode.

[0098] The anode is the electrode for injecting holes, and it can inject holes into an organic functional layer, such as a hole injection layer, a hole transport layer, or a light-emitting layer. The anode may include at least one of a conductive metal, a conductive metal oxide, or a conductive polymer. Preferably, the absolute value of the difference between the work function of the anode and the highest occupied molecular orbital (HOMO) level or valence band level of the light-emitting material in the light-emitting layer, or the p-type semiconductor material in the hole injection layer, hole transport layer, or electron blocking layer, is less than 0.5 eV, more preferably less than 0.3 eV, and more preferably less than 0.2 eV. The anode material includes, but is not limited to, at least one of Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, indium tin oxide (ITO), aluminum-doped zinc oxide (AZO), or other suitable and known anode materials, which can be readily selected by those skilled 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), etc. In some embodiments, the anode can be patterned, for example, patterned ITO conductive substrates are commercially available and can be used to fabricate the organic light-emitting device of this application.

[0099] The cathode is the electrode for injecting electrons, and it can inject electrons into organic functional layers, such as electron injection layers, electron transport layers, or light-emitting layers. The cathode may include at least one of a conductive metal or a conductive metal oxide. Preferably, the absolute value of the difference between the work function of the cathode and the lowest unoccupied molecular orbital (LUMO) level or conduction band level of the light-emitting material in the light-emitting layer, or the n-type semiconductor material serving as the electron injection layer, electron transport layer, or hole blocking layer, is less than 0.5 eV, preferably less than 0.3 eV, and more preferably less than 0.2 eV. All materials suitable for use as cathodes in organic electronic devices may be used as cathode materials for the devices of this application. Cathode materials include, but are not limited to, at least one of Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloy, BaF2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, and ITO. The cathode material can be deposited using any suitable technique, such as appropriate physical vapor deposition methods, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), etc.

[0100] In some embodiments, please refer to Figure 1 The organic functional layer 130 may include one or more functional film layers. For example, the organic functional layer 130 may include at least one of a hole injection layer 131, a hole transport layer 132, an auxiliary hole transport layer 133, a light-emitting layer 134, an electron transport layer 135, and an electron injection layer 136. Further, the organic functional layer 130 may also include at least one of an electron blocking layer and a hole blocking layer. Materials suitable for these functional film layers are as described above and will not be repeated here.

[0101] In some embodiments, please refer to Figure 1 The organic functional layer 130 includes at least a light-emitting layer 134 and a hole transport layer 132, wherein the hole transport layer 132 is located between the first electrode 120 and the light-emitting layer 134; wherein the material of the hole transport layer 132 includes at least one organic compound as described above.

[0102] In some embodiments, please refer to Figure 1 The organic functional layer 130 includes at least a light-emitting layer 134, a hole transport layer 132, and an auxiliary hole transport layer 133; the hole transport layer 132 is located on the side of the first electrode 120 facing the second electrode 140, the auxiliary hole transport layer 133 is located on the side of the hole transport layer 132 away from the first electrode 120, and the light-emitting layer 134 is located on the side of the auxiliary hole transport layer 133 away from the hole transport layer 132; wherein, the material of the auxiliary hole transport layer 133 includes at least one organic compound as described above.

[0103] This application adds an auxiliary hole transport layer 133 formed of an organic compound represented by the general formula (1) as described above between the hole transport layer 132 and the light-emitting layer 134. On the one hand, it can effectively improve the hole transport efficiency, and on the other hand, it can effectively block electrons from leaking backward from the light-emitting layer, reduce exciton quenching, effectively reduce energy consumption, improve the recombination efficiency of charge carriers in the light-emitting layer 134, thereby improving the luminous efficiency and lifetime of the organic light-emitting device 100, while maintaining a low driving voltage.

[0104] For details, please refer to Figure 1 The organic light-emitting device 100 includes a substrate 110, a first electrode 120, an organic functional layer 130, and a second electrode 140. The organic functional layer 130 includes a hole injection layer 131, a hole transport layer 132, an auxiliary hole transport layer 133, a light-emitting layer 134, an electron transport layer 135, and an electron injection layer 136. The first electrode 120 is located on the substrate 110. The hole injection layer 131 is located on the side of the first electrode 120 away from the substrate 110. The hole transport layer 132 is located on the side of the hole injection layer 131 away from the first electrode 120. The auxiliary hole transport layer 133 is located on the side of the hole transport layer 132 away from the hole injection layer 131. The light-emitting layer 134 is located on the side of the auxiliary hole transport layer 133 away from the hole transport layer 132. The electron transport layer 135 is located on the side of the light-emitting layer 134 away from the auxiliary hole transport layer 133. The electron injection layer 136 is located between the electron transport layer 135 and the second electrode 140. The first electrode 120 can be an anode, and the second electrode 140 can be a cathode.

[0105] In some embodiments, the luminescent material of the luminescent layer 134 is selected from at least one of a singlet luminescent material, a triplet luminescent material, or a delayed fluorescence (TADF) material.

[0106] In some embodiments, the light-emitting layer 134 includes a host material and a guest material.

[0107] In some embodiments, the thickness of the organic functional layer 130 is 10 nm to 200 nm, preferably 20 nm to 150 nm, more preferably 30 nm to 100 nm, and most preferably 40 nm to 90 nm.

[0108] In some embodiments, the organic light-emitting device 100 may be, but is not limited to, organic light-emitting diodes (OLEDs), organic photovoltaic cells (OPVs), organic light-emitting electrochemical 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 (OLEFETs). Preferably, it is an organic light-emitting diode, an organic light-emitting cell, or an organic light-emitting field-effect transistor.

[0109] In some embodiments, the organic light-emitting device 100 can be applied to a variety of electronic devices, such as display devices, lighting devices, light sources, sensors, etc.

[0110] This application also provides a display device, which includes the organic light-emitting device 100 as described above. This display device can be used in fields such as smartphones, tablets, smart wearable devices, televisions, virtual reality (VR), microdisplays, and automotive displays, but is not limited thereto.

[0111] The present application will be further described below with reference to specific embodiments. However, the present application is not limited to the following embodiments. It should be understood that the appended claims summarize the scope of the present application. Under the guidance of the concept of the present application, those skilled in the art should realize that any 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.

[0112] I. Synthesis of Organic Compounds Synthesis of intermediate A:

[0113] Synthetic steps of intermediate A: Intermediate a (10 mmol), compound b (10 mmol), and cesium carbonate (20 mmol) were dissolved in DMF solvent and stirred at 140 °C for 6 h under a nitrogen atmosphere. After cooling the reaction system to room temperature, a portion of the solvent was removed using a rotary evaporator, followed by extraction three times with dichloromethane and water. After separation, the organic phase was evaporated to dryness to obtain the crude product. The crude product was purified by column chromatography to obtain intermediate A in 85% yield. The mass spectrometry result of intermediate A was m / z [H+] = 452.

[0114] Synthesis of intermediate B:

[0115] The synthesis steps for intermediate B were the same as those for intermediate A, with a yield of 81%. The mass spectrometry results for intermediate B are m / z [H]. + =528.

[0116] Synthesis of intermediate C:

[0117] The synthesis of intermediate C followed the same steps as intermediate A, with a yield of 75%. The mass spectrometry results for intermediate C are m / z [H]. + =502.

[0118] Synthesis of intermediate D:

[0119] The synthesis steps for intermediate D were the same as those for intermediate A, with a yield of 70%. The mass spectrometry results for intermediate D are m / z [H]. + =542.

[0120] Example 1 Synthesis of Compound M1

[0121] Synthesis of intermediates 1-2: Intermediate A (10 mmol), intermediate 1-1 (10 mmol), Pd132 (0.1 mmol), X-Phos (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in xylene and stirred at 120 °C for 12 h under a nitrogen atmosphere. After cooling the reaction system to room temperature, a portion of the solvent was removed by rotary evaporation. The mixture was then extracted three times with dichloromethane and water. The organic phase was evaporated to dryness to obtain the crude product. Further purification by column chromatography yielded intermediate 1-2 in 88% yield. The mass spectrometry results for intermediate 1-2 were [m / z [H]]. + = 474.

[0122] Synthesis of compound M1: Intermediates 1-2 (10 mmol), 1-3 (10 mmol), Pd132 (0.1 mmol), X-Phos (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in xylene and stirred at 140 °C for 12 h under a nitrogen atmosphere. After cooling the reaction mixture to room temperature, a portion of the solvent was removed by rotary evaporation. The mixture was then extracted three times with dichloromethane and water. The organic phase was evaporated to dryness to obtain the crude product. Further purification by column chromatography yielded compound M1 in 84% yield. The mass spectrometry results for compound M1 are m / z [H]. + = 626. Elemental analysis results show C, 88.16; H, 4.85; N, 4.46; O, 2.53.

[0123] The following compounds were prepared using the same method as in Example 1. The compound structures, raw materials, and related data for each example are shown in Table 1: Table 1

[0124] Comparative Example This application also provides Comparative Example 1 and Comparative Example 2, where the organic compound of Comparative Example 1 is "Ref-01" and the organic compound of Comparative Example 2 is "Ref-02". The chemical structural formulas of Ref-01 and Ref-02 are shown below: .

[0125] II. Fabrication and Characterization of OLED Organic Light-Emitting Devices The following specific embodiments illustrate in detail the fabrication method and process of OLED organic light-emitting devices using the organic compounds of this application. In the following method for fabricating OLED organic light-emitting devices, ITO conductive glass is used as the anode substrate (including the substrate and the anode), 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 guest 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. Furthermore, compounds M1~M17 from the aforementioned synthesis examples and compounds Ref-01~Ref-02 from the comparative examples are used as auxiliary hole transport materials to prepare corresponding OLED organic light-emitting devices. The chemical structural formulas of PD, HT, BH, BD, ET, and Liq are shown below:

[0126] In this embodiment, the structure of the prepared OLED organic light-emitting device is: ITO / PD:HT (3:97, 10 nm) / HT (130 nm) / compound M1 (90 nm) / BH:BD (3%, 40 nm) / ET:Liq (5:5, 30 nm) / Liq (1 nm) / Al (100 nm). The structure of the OLED organic light-emitting device can be referred to... Figure 1 .

[0127] Taking the fabrication method of OLED organic light-emitting device using compound M1 as an auxiliary hole transport material as an example, the prepared OLED organic light-emitting device is denoted as "OLED-1". The fabrication method of organic light-emitting device OLED-1 includes the following steps: a. Cleaning of conductive glass substrate: Cleaning is performed using chloroform, ketone, and isopropanol, followed by ultraviolet ozone plasma treatment; b. Preparation of organic functional layer: First, the conductive glass substrate obtained in step a is transferred into a vacuum vapor deposition apparatus and deposited under high vacuum (1×10⁻⁶). -6 At millibars, resistance heating was used for evaporation at 1 Å s. -1 Hole implantation materials PD and HT were deposited on ITO at a deposition rate of 3:97, resulting in a hole implantation layer with a thickness of 10 nm. Then, at a deposition rate of 1.5 Å s⁻¹... -1 Hole transport material HT was deposited on the hole injection layer at a deposition rate of 1 Å s to obtain a hole transport layer with a thickness of 130 nm. Then, at a deposition rate of 1 Å s... -1 Compound M1, as described in Example 1, was deposited on the hole transport layer at a deposition rate of 1 Å / s to obtain an auxiliary hole transport layer with a thickness of 90 nm. Next, BH and BD were deposited on the auxiliary hole transport layer at a deposition rate of 1 Å / s, with a deposition rate ratio of 97:3, to obtain a light-emitting layer with a thickness of 40 nm. Subsequently, electron transport materials ET and Liq were placed in different evaporation crucibles in a vacuum chamber and subjected to high vacuum (1 × 10⁻⁶) conditions. -6 At a weight ratio of 5:5, ET and Liq were co-deposited at a density of 1 Å / s to form a 30 nm thick electron transport layer on the luminescent layer. Then, at 1 Å / s... -1 Electron injection material Liq was deposited on the electron transport layer at a deposition rate of 1 Å s⁻¹, resulting in an electron injection layer with a thickness of 1 nm. Then, at a deposition rate of 1 Å s⁻¹... -1 The cathode material Al was deposited on the electron injection layer at a certain evaporation rate to obtain a cathode with a thickness of 100 nm.

[0128] c. Encapsulation: The device obtained in step b is encapsulated in a nitrogen glove box using ultraviolet-cured resin to finally obtain the organic light-emitting device OLED-1.

[0129] Following the fabrication method of OLED-1, compounds M2 to M17 synthesized in the examples were selected as auxiliary hole transport materials to prepare OLED-2 to OLED-17. In the fabrication methods of OLED-1 to OLED-17, all experimental conditions were the same except for the auxiliary hole transport materials.

[0130] Following the fabrication method of OLED-1, comparative organic light-emitting devices OLED-Ref-01 and OLED-Ref-02 were prepared by using compounds Ref-01 and Ref-02 as auxiliary hole transport materials. The preparation methods for OLED-Ref-01 and OLED-Ref-02 were identical to those for OLED-1, except for the auxiliary hole transport materials.

[0131] In this application, the current-voltage (ND) of OLED-1 to OLED-17 and OLED-Ref-01 to OLED-Ref-02 devices is described. JV The characteristics were characterized, and important parameters such as luminous efficiency and lifetime were recorded, as shown in Table 2. Luminous efficiency is defined as the current density at 10 mA cm⁻¹. -2 The value obtained at that time; lifetime (LT95) is at 10 mA cm -2 The time it takes for the brightness to drop to 95% of the initial brightness under the given current density.

[0132] Table 2

[0133] As can be seen from the data in Table 2, when the organic compounds M1 to M17 prepared in Examples 1 to 17 of this application are used as materials for the auxiliary hole transport layer, the luminous efficiency and lifetime of the prepared organic light-emitting devices OLED-1 to OLED-17 are significantly better than those of the control devices OLED-Ref-01 and OLED-Ref-02, and the driving voltage is lower. This is because, in the aromatic amine compound constructed with benzo[a]carbazole and dibenzo[a]furan as the core, benzo[a]carbazole extends the conjugated plane through fused benzene rings, exhibiting stronger molecular rigidity compared to ordinary carbazole. This rigid structure can suppress vibrational relaxation of molecules during nonradiative transitions, reduce molecular thermal motion, improve material stability, and lower energy consumption. Furthermore, the COC bond in dibenzo[a]furan has a high bond energy, further ensuring the stability of the molecular structure. At the same time, the oxygen-containing dibenzo[a]furan has a certain electron affinity, which can effectively block electrons from leaking backward from the light-emitting layer, reducing exciton quenching. When this organic compound is used as an auxiliary hole transport layer material for blue light devices in organic light-emitting devices, it can significantly improve the luminous efficiency and lifespan of organic light-emitting devices while maintaining a low driving voltage, achieving excellent comprehensive performance and possessing broad application prospects.

[0134] The technical features of the above embodiments can be combined in any way. For the sake of brevity, not all possible combinations of the technical features in the above embodiments are described. However, as long as there is no contradiction in the combination of these technical features, they should be considered to be within the scope of this specification.

[0135] The embodiments described above are merely illustrative of several implementation methods of this application, and while the descriptions are relatively specific and detailed, they should not be construed as limiting the scope of the patent application. It should be noted that those skilled in the art can make various modifications and improvements without departing from the concept of this application, and these all fall within the protection scope of this application. Therefore, the protection scope of this patent application should be determined by the appended claims.

Claims

1. An organic compound, characterized in that, The organic compound has the structure represented by general formula (1): General formula (1); in: Ar1 is selected from C1, whether substituted or unsubstituted. 6-15 Aromatic groups; L is selected from C, whether substituted or unsubstituted. 6-30 Aromatic groups, substituted or unsubstituted C 5-30 One or a combination of at least two of the heteroaromatic groups; Ar2 is selected from C that has been substituted or not substituted. 6-30 Aromatic groups, substituted or unsubstituted C 5-30 One or a combination of at least two of the heteroaromatic groups.

2. The organic compound according to claim 1, characterized in that, Ar1 is selected from phenyl.

3. The organic compound according to claim 1, characterized in that, L is selected from one or a combination of at least two of the following: phenylene, biphenylene, naphthylene, fluorene, dibenzofuranyl, and dibenzothiopheneyl.

4. The organic compound according to claim 1, characterized in that, Ar2 is selected from any of the following groups: ； in, Indicates the connection site.

5. The organic compound according to claim 1, characterized in that, The organic compound is selected from any of the following structures: 。 6. A mixture, characterized in that, The mixture includes at least one organic functional material and at least one organic compound as described in any one of claims 1 to 5, wherein the organic functional material is selected from hole injection materials, hole transport materials, auxiliary hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, organic light-emitting guest materials, or organic host materials.

7. A composition, characterized in that, The composition comprises at least one organic solvent and at least one organic compound as claimed in any one of claims 1 to 5, or the composition comprises at least one of the organic solvents and a mixture as claimed in claim 6.

8. An organic light-emitting device, characterized in that, include: First electrode; The second electrode is disposed opposite to the first electrode; as well as An organic functional layer is located between the first electrode and the second electrode; The organic functional layer is made of at least one organic compound as described in any one of claims 1 to 5, or the organic functional layer is made of a mixture as described in claim 6, or the organic functional layer is prepared from a composition as described in claim 7.

9. The organic light-emitting device according to claim 8, characterized in that, The organic functional layer includes: A hole transport layer is located on the side of the first electrode facing the second electrode; An auxiliary hole transport layer is located on the side of the hole transport layer away from the first electrode; The light-emitting layer is located on the side of the auxiliary hole transport layer away from the hole transport layer; The auxiliary hole transport layer is made of at least one organic compound as described in any one of claims 1 to 5, or the auxiliary hole transport layer is made of a mixture as described in claim 6, or the auxiliary hole transport layer is made of a composition as described in claim 7.

10. A display device, characterized in that, Including the organic light-emitting device as described in claim 8 or 9.

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