Arylamine compounds, mixtures, organic light-emitting devices and display panels

Abstract

The application discloses an arylamine compound, a mixture, an organic light-emitting device and a display panel. The arylamine compound is selected from the structural formula shown in any one of the drawings. The arylamine compound disclosed by the application contains a polyheterocyclic ring, i.e. benzo[k]oxo / thiaxanthene or benzo[4,5-bcd]furan / thiophene; the arylamine compound has a high refractive index in the visible light region; when the arylamine compound is applied to a light extraction layer of an electronic device, the light extraction efficiency can be significantly improved, so that the performance of the device is optimized.

Description

Technical Field

[0001] This application relates to the field of display technology, specifically to an aromatic amine compound, a mixture, an organic light-emitting device, and a display panel. Background Technology

[0002] Organic light-emitting diode (OLED) display devices are an advanced self-emissive display technology. They generate excitons through the transfer and recombination of charge carriers between different functional layers. These excitons then emit light through highly quantum-efficient organic compounds or metal complexes. OLED technology is renowned for its advantages such as self-emission, high brightness, high efficiency, high contrast, and fast response time.

[0003] In recent years, the luminous efficiency of OLED diodes has significantly improved, with their internal quantum efficiency approaching the theoretical limit. Therefore, improving light extraction efficiency has become crucial for further enhancing device stability and current efficiency. For example, optimizing the stacking of the emitter layer metal complex and the matching of refractive indices between functional layers can effectively improve light extraction efficiency. In 2001, Hung et al. coated the surface of a metal cathode with an organic or inorganic compound layer approximately 50 nanometers thick, enhancing device performance by precisely controlling the thickness and refractive index. In 2003, Riel et al. attempted to deposit a high-refractive-index (n=2.6) inorganic compound, ZnSe, onto the cathode, utilizing the difference in refractive index between functional layers to improve light extraction efficiency. However, the high evaporation temperature and slow evaporation rate of inorganic materials have limited their application in OLED devices.

[0004] Therefore, there is an urgent need to develop new light extraction layer materials to expand their application in OLEDs. Summary of the Invention

[0005] This application provides an aromatic amine compound, a mixture thereof, an organic light-emitting device, and a display panel. The aromatic amine compound of this application exhibits a low extinction coefficient and a high refractive index in the visible light region. When the aromatic amine compound of this application is applied to the light extraction layer of an electronic device, the light extraction efficiency can be significantly improved, thereby optimizing the device performance.

[0006] This application provides an aromatic amine compound, wherein the compound is a compound represented by any one of the structural formulas (1) to (3):

[0007]

[0008] Ar1 is selected from ;

[0009] In this context, Z may appear the same or different each time, and Z is selected from CH or nitrogen atoms, while X and Y are independently selected from oxygen atoms or sulfur atoms;

[0010] L1, L2 and L3 are independently selected from one or more combinations of single bonds, substituted or unsubstituted aromatic groups having 6 to 25 ring atoms, and substituted or unsubstituted heteroaromatic groups having 5 to 25 ring atoms;

[0011] Ar2 is selected from one or more combinations of hydrogen atoms, substituted or unsubstituted aromatic groups having 6 to 25 ring atoms, and substituted or unsubstituted heteroaromatic groups having 5 to 25 ring atoms;

[0012] When the aromatic group and / or the heteroaromatic group is substituted, the substituent is selected from one or more combinations of aromatic groups having 6 to 25 ring atoms and heteroaromatic groups having 5 to 25 ring atoms;

[0013] When the aromatic amine compound contains a heteroaromatic group, the heteroatom in the heteroaromatic group is selected from one or more combinations of nitrogen atom, oxygen atom, and sulfur atom;

[0014] Indicates the connection site.

[0015] A second aspect of this application provides a mixture comprising at least one of the above-mentioned aromatic amine compounds and an organic functional material, wherein the organic functional material is selected from at least one of hole injection materials, hole transport materials, light-emitting auxiliary materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, organic light-emitting guest materials, and organic host materials.

[0016] A third aspect of this application provides an organic light-emitting device, the organic light-emitting device comprising:

[0017] anode;

[0018] The cathode is disposed opposite to the anode;

[0019] An organic functional layer is located between the anode and the cathode, and the organic functional layer includes a light-emitting layer; and,

[0020] A light extraction layer, the light extraction layer being located on the side of the cathode away from the organic functional layer, the light extraction layer comprising the aforementioned aromatic amine compound, or the light extraction layer comprising the aforementioned mixture.

[0021] A fourth aspect of this application provides a display panel, the display panel including the above-described organic light-emitting device.

[0022] This invention provides an aromatic amine compound, a mixture thereof, an organic light-emitting device, and a display panel. The aromatic amine compound of this application contains a multi-component fused heterocycle, namely benzo[k]oxy / thioxanthracene or benzo[4,5-bcd]furan / thiophene; it possesses a high first singlet excited state energy level, which avoids absorption of light emitted by the device. Furthermore, due to its large conjugated planar structure containing oxygen or sulfur atoms, it exhibits a high refractive index. Therefore, when the aromatic amine compound of this application is used in the light extraction layer of an electronic device, it not only avoids absorption of light emitted by the device but also significantly improves the light extraction efficiency, thereby optimizing device performance. Attached Figure Description

[0023] To more clearly illustrate the technical solutions in the embodiments of this application, the accompanying drawings used in the description of the embodiments will be briefly introduced below. Obviously, the accompanying drawings described below are only some embodiments of this application. For those skilled in the art, other drawings can be obtained based on these drawings without creative effort.

[0024] Figure 1 This is a schematic diagram of the organic light-emitting device structure provided in the embodiments of this application.

[0025] Explanation of reference numerals in the attached figures:

[0026] 1. Substrate; 2. Anode; 3. Organic functional layer; 3a. Hole injection layer; 3b. Hole transport layer; 3c. Light-emitting layer; 3d. Electron transport layer; 3e. Electron injection layer; 4. Cathode; 5. Light extraction layer. Detailed Implementation

[0027] The technical solutions of the embodiments of this application will be clearly and completely described below with reference to the accompanying drawings. Obviously, the described embodiments are only some embodiments of this application, and not all embodiments. Based on the embodiments of this application, all other embodiments obtained by those skilled in the art without creative effort are within the scope of protection of this application.

[0028] This application provides an aromatic amine compound, a mixture, an organic light-emitting device, and a display panel. These are described in detail below. It should be noted that the order of description of the following embodiments is not intended to limit the preferred order of the embodiments. Furthermore, in the description of this application, the term "comprising" means "including but not limited to". For example, it should be considered that the description of a range from 1 to 6 specifically discloses sub-ranges, such as from 1 to 3, from 1 to 4, from 1 to 5, from 2 to 4, from 2 to 6, from 3 to 6, etc., as well as single numbers within the range, such as 1, 2, 3, 4, 5, and 6, regardless of the range. Additionally, whenever a numerical range is indicated herein, it means including any referenced number (fraction or integer) within the indicated range.

[0029] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by those skilled in the art.

[0030] As used herein, the term "and / or" includes any and all combinations of one or more of the related listed items.

[0031] In this application, "substitution" means that the hydrogen atom in the substituent is replaced by the substituent.

[0032] In this application, hydrogen atoms include isotopes with different numbers of neutrons, namely protium, deuterium, and tritium.

[0033] 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.

[0034] In this application, "ring atom number" refers to the number of atoms in the ring itself of a structural compound obtained by atomic bonding to form a ring (e.g., monocyclic compound, fused ring compound, cross-linked compound, carbocyclic compound, heterocyclic compound). When the ring is substituted by a substituent, the atoms contained in the substituent are not included in the ring-forming atoms. The same applies to the "ring atom number" described below unless otherwise specified. For example, a benzene ring has 6 ring atoms, a naphthalene ring has 10 ring atoms, and a thiophene group has 5 ring atoms.

[0035] "Aryl or aromatic group" refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removing one hydrogen atom. It can be a monocyclic aryl, a fused-ring aryl, or a polycyclic aryl; for polycyclic rings, at least one must be an aromatic ring system. For example, "substituted or unsubstituted aryl with 5 to 25 ring atoms" refers to an aryl group containing 5 to 25 ring atoms, optionally further substituted; suitable examples include, but are not limited to: benzene, biphenyl, terphenyl, naphthalene, anthracene, fluoranthene, phenanthrene, benzo[a]phenanthrene, dinaphthalene, tetraphenyl, pyrene, benzo[a]pyrene, acenaphthene, fluorene, and their derivatives. Understandably, multiple aryl groups can also be interrupted by short non-aromatic units (e.g., <10% non-H atoms, such as C, N, or O atoms), specifically acenaphthene, fluorene, or 9,9-diarylfluorene, triarylamines, and diaryl ether systems should also be included in the definition of aryl.

[0036] In this application, the heteroaromatic group with 5 to 25 ring atoms refers to a monovalent group comprising a carbocyclic aromatic system having at least one heteroatom selected from nitrogen, oxygen, phosphorus, sulfur or silicon as a cyclic atom and 5 to 25 ring atoms. Non-limiting examples of heteroaromatic groups with 5 to 25 ring atoms may include furanyl, thiopheneyl, pyrrolyl, 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, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl, 1,3 ,5-triazinyl, benzofuranyl, benzoisofuranyl, benzothiophenyl, benzoisothiophenyl, indoleyl, isoindoleyl, indazoleyl, benzimidazolyl, benzoxazolyl, benzoisoxazolyl, benzothiazolyl, 2,1,3-benzoxadiazole, quinolinyl, isoquinolinyl, terpineyl, phthalazinyl, quinazolinyl, quinolinyl, naphthidyl, benzotriazinyl, benzoxazinyl, purineyl, pteridinyl, indazinyl, benzothiazinyl, acridineyl, phenazinyl, phenthiazinyl, phenoxazinyl, dibenzofuranyl, dibenzothiaphenyl, carbazoleyl, naphthiofuranyl, 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.

[0037] In this application, the single key is connected This indicates a connection site or fusion site.

[0038] In this application, when no linking site is specified in the group, it means that any linkable site in the group can be selected as the linking site;

[0039] In this application, the single bonds connecting the substituents extend through the corresponding ring, indicating that the substituent can be connected to any position on the ring, for example... R is attached to any substituted site on the benzene ring.

[0040] Most existing light extraction layer materials are inorganic materials, but the high evaporation temperature and slow evaporation rate of inorganic materials limit their application in OLED devices.

[0041] To solve the above-mentioned technical problems, this application provides an aromatic amine compound, wherein the aromatic amine compound is selected from any compound represented by any one of the structural formulas (1) to (3):

[0042]

[0043] Ar1 is selected from ;

[0044] In this context, Z may appear the same or different each time, and Z is selected from CH or nitrogen atoms, while X and Y are independently selected from oxygen atoms or sulfur atoms;

[0045] L1, L2 and L3 are independently selected from one or more combinations of single bonds, substituted or unsubstituted aromatic groups having 6 to 25 ring atoms, and substituted or unsubstituted heteroaromatic groups having 5 to 25 ring atoms;

[0046] Ar2 is selected from one or more combinations of hydrogen atoms, substituted or unsubstituted aromatic groups having 6 to 25 ring atoms, and substituted or unsubstituted heteroaromatic groups having 5 to 25 ring atoms;

[0047] When the aromatic group and / or the heteroaromatic group is substituted, the substituent is selected from one or more combinations of aromatic groups having 6 to 25 ring atoms and heteroaromatic groups having 5 to 25 ring atoms;

[0048] When the aromatic amine compound contains a heteroaromatic group, the heteroatom in the heteroaromatic group is selected from one or more combinations of nitrogen atom, oxygen atom, and sulfur atom;

[0049] Indicates the connection site.

[0050] It can be understood that, in the embodiments of this application, when L1, L2 and L3 are not single bonds, L1, L2 and L3 are divalent groups.

[0051] In some embodiments, the Ar1 is selected from any of the following groups:

[0052] .

[0053] In some embodiments, L1, L2, and L3 are independently selected from one or more combinations of single bonds, divalent phenyl, divalent naphthyl, divalent diphenyl, divalent pyridyl, divalent pyrazinyl, divalent carbazole, divalent phenanthryl, divalent benzophenanthrene, divalent o-phenanthroline, divalent dibenzofuranyl, divalent dibenzothiophene, divalent benzooxazolyl, divalent benzothiazolyl, divalent naphthiofuranyl, and divalent naphthiophene.

[0054] In some embodiments, L1, L2, and L3 are independently selected from single bonds or any of the following groups:

[0055] .

[0056] In some specific embodiments, L1, L2, and L3 are independently selected from single bonds or any of the following groups:

[0057] .

[0058] In some embodiments, the Ar2 is selected from hydrogen atom, phenyl, benzoxazolyl, benzothiazolyl, phenanthrene, benzophenanthrene, o-phenanthrolinel, dibenzofuranyl, dibenzothiophene, N A combination of one or more of the following: phenylcarbazolyl, quinolinyl, isoquinolinyl, quinoxalinyl, naphthobenzofuranyl, naphthobenzothiophenyl, and phenanthrenebenzofuranyl.

[0059] In some embodiments, the Ar2 is selected from any of the following groups:

[0060] .

[0061] In some specific embodiments, the Ar2 is selected from any of the following groups:

[0062] .

[0063] In some embodiments, the aromatic amine compound is selected from any one of the following compounds:

[0064] .

[0065] It is understood that the aromatic amine compounds in the embodiments of this application are not limited to the examples above.

[0066] In some embodiments, the glass transition temperature Tg is ≥100°C; in a preferred embodiment, Tg is ≥20°C; in a more preferred embodiment, Tg is ≥140°C; in a more preferred embodiment, Tg is ≥160°C; and in a most preferred embodiment, Tg is ≥180°C.

[0067] The aromatic amine compounds described in this application have high glass transition temperatures, which can improve the thermal stability of the compounds.

[0068] In some embodiments, the aromatic amine compound has a refractive index greater than 1.7 at a wavelength of 630 nm; preferably, greater than 1.78; more preferably, greater than 1.83.

[0069] In some embodiments, its singlet energy (S1) is greater than or equal to 2.7 eV; preferably, greater than or equal to 2.8 eV; more preferably, greater than or equal to 2.85 eV.

[0070] In some embodiments, the extinction coefficient at a wavelength of 430 nm is less than 0.1; preferably, less than 0.003; more preferably, less than 0.001. This results in high transmittance of visible light, reducing the impact on the light output efficiency of the device.

[0071] In some preferred embodiments, the aromatic amine compound has a large extinction coefficient in the wavelength range of ≤400 nm; preferably, the extinction coefficient at a wavelength of 350 nm is ≥0.3; more preferably ≥0.5, even more preferably ≥0.7, and most preferably ≥1.0. This meets the requirements of vapor-deposited OLED materials.

[0072] In some embodiments, the molecular weight of the aromatic amine compound is ≤1200 g / mol, preferably ≤100 g / mol, very preferably ≤1000 g / mol, more preferably ≤950 g / mol, and most preferably ≤900 g / mol.

[0073] In other embodiments, the aromatic amine compound has a molecular weight ≥800 g / mol, preferably ≥900 g / mol, very preferably ≥1000 g / mol, more preferably ≥1100 g / mol, and most preferably ≥1200 g / mol. This is to meet the requirements of the printing process in OLEDs.

[0074] In other embodiments, the aromatic amine compound has a solubility in toluene of ≥2 mg / ml at 25°C, preferably ≥3 mg / ml, more preferably ≥4 mg / ml, and most preferably ≥5 mg / ml.

[0075] The aromatic amine compounds of this application contain multiple fused heterocycles, namely benzo[k]oxy / thioxanthracene or benzo[4,5-bcd]furan / thiophene; they possess high first singlet excitation energy levels, which can avoid absorption of light emitted by the device. Furthermore, due to their large conjugated planar structure containing oxygen or sulfur atoms, they exhibit high refractive indices. Therefore, when the aromatic amine compounds of this application are applied to the light extraction layer of electronic devices, not only can absorption of light emitted by the device be avoided, but the light extraction efficiency can also be significantly improved, thereby optimizing device performance. This application also provides a mixture comprising at least one of the above-mentioned aromatic amine compounds and an organic functional material, wherein the organic functional material is selected from at least one of hole injection materials, hole transport materials, light-emitting auxiliary materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, organic light-emitting guest materials, and organic host materials.

[0076] This application also provides a composition comprising at least one compound as described above, and at least one organic solvent; wherein the at least one organic solvent is selected from 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 mixtures of two or more solvents.

[0077] In some embodiments, the at least one organic solvent is selected from at least one of aromatic or heteroaromatic solvents.

[0078] In some embodiments, the at least one organic solvent is selected from at least one of aliphatic chain / ring substituted aromatic solvents, aromatic ketone solvents, and aromatic ether solvents.

[0079] Solvents suitable for embodiments of this application include, but are not limited to: aromatic or heteroaromatic solvents: p-diisopropylbenzene, pentobenzene, tetrahydronaphthalene, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, dipentylbenzene, tripentylbenzene, pentyltoluene, o-xylene, m-xylene, p-xylene, 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, 1-methoxynaphthalene, cyclohexylbenzene Dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, 1-methylnaphthalene, 1,2,4-trichlorobenzene, 1,3-dipropoxybenzene, 4,4-difluorodiphenylmethane, 1,2-dimethoxy-4-(1-propenyl)benzene, diphenylmethane, 2-phenylpyridine, 3-phenylpyridine, N-methyldiphenylamine, 4-isopropylbiphenyl, 4-(3-phenylpropyl)pyridine, benzyl benzoate, 1,1-bis(3,4-dimethylphenyl)ethane, 2-isopropylnaphthalene, dibenzyl ether, etc. Ketone-based solvents: 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, isophorone, 2,6,8-trimethyl-4-nonanone, fentanyl, 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2,5-hexanedione, phorone, di-n-pentyl ketone; Aromatic ether solvents: 3-phenoxytoluene, butoxybenzene, benzyl butylbenzene, 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, 1,2,4-trimethoxybenzene, 4-(1-propenyl)-1,2-dimethoxybenzene, 1,3-dimethoxybenzene, glycidylphenyl Ethers, dibenzyl ether, 4-tert-butylanisole, trans-p-propenylanisole, 1,2-dimethoxybenzene, 1-methoxynaphthalene, diphenyl ether, 2-phenoxymethyl ether, 2-phenoxytetrahydrofuran, ethyl-2-naphthyl ether, pentanyl 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; Ester solvents: alkyl octanoate, alkyl sebacate, alkyl stearate, alkyl benzoate, alkyl phenylacetate, alkyl cinnamate, alkyl oxalate, alkyl maleate, alkyl lactone, alkyl oleate, etc.

[0080] The compositions in the embodiments of this application are coatings or printing inks.

[0081] In some implementations, when the composition of the present application examples is a printing ink, the solvent of at least one of the solvents may be selected from: aliphatic ketones, such as 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2,5-hexanedione, 2,6,8-trimethyl-4-nonanone, phorone, di-n-pentyl ketone, etc.; or aliphatic ethers, such as pentyl 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.

[0082] In other embodiments, when the composition of this application is a printing ink, the composition contains another organic solvent. This other organic solvent includes (but is not limited to): 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, at least one of these.

[0083] In a preferred embodiment, the composition is a solution.

[0084] In another preferred embodiment, the composition is a suspension.

[0085] The compositions in the embodiments of this application include 0.01 to 20 wt% of the aromatic amine compounds of the aforementioned embodiments, preferably 0.1 to 15 wt%, more preferably 0.2 to 10 wt%, and most preferably 0.25 to 5 wt%.

[0086] This application also relates to the use of the composition as a coating or printing ink in the preparation of organic light-emitting devices, particularly preferably by a preparation method of printing or coating.

[0087] Suitable printing or coating technologies 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 techniques are preferred.

[0088] When the composition is a solution or suspension, it may additionally include one or more components, such as: surfactants, lubricants, wetting agents, dispersants, hydrophobic agents, adhesives, etc., and the components have functions such as adjusting viscosity, film-forming properties, and improving adhesion.

[0089] For details regarding printing technology and its requirements when the composition is a solution, such as solvent and concentration, viscosity, etc., please refer to "Handbook of Print Media: Technologies and Production Methods" edited by Helmut Kipphan, ISBN 3-540-67326-1.

[0090] This application also provides an organic light-emitting device 100, the organic light-emitting device 100 comprising:

[0091] Anode 2; cathode 4 disposed opposite to anode 2; organic functional layer 3 located between anode 2 and cathode 4, wherein organic functional layer 3 includes light-emitting layer 3c; and light extraction layer 5 located on the side of cathode 4 away from organic functional layer 3, wherein light extraction layer 5 includes an aromatic amine compound of the foregoing embodiments, or, wherein light extraction layer 5 includes a mixture of the foregoing embodiments, or, wherein light extraction layer 5 is prepared from the composition of the foregoing embodiments.

[0092] In some embodiments, the glass transition temperature Tg of the light extraction layer 5 is ≥100°C, in a preferred embodiment Tg is ≥120°C, in a more preferred embodiment Tg is ≥140°C, in a more preferred embodiment Tg is ≥160°C, and in a most preferred embodiment Tg is ≥180°C.

[0093] In this embodiment, when the light extraction layer 5 has a high glass transition temperature, the organic light-emitting device 100 has good stability.

[0094] In some embodiments, the light extraction layer 5 has a refractive index greater than or equal to 1.7 at a wavelength of 630 nm; preferably, greater than or equal to 1.78; more preferably, greater than or equal to 1.83.

[0095] According to the organic light-emitting device 100 in the embodiments of this application, the light extraction layer 5 has a high refractive index, which can help improve the light efficiency of the organic light-emitting device 100, especially the external light-emitting efficiency.

[0096] In some preferred embodiments, the singlet energy (S1) contained in the light extraction layer 5 is greater than or equal to 2.7 eV; preferably, greater than or equal to 2.8 eV; more preferably, greater than or equal to 2.85 eV.

[0097] In some other preferred embodiments, the singlet energy (S1) contained in the light extraction layer 5 is less than or equal to 3.1 eV; preferably, it is less than or equal to 3.0 eV.

[0098] In some embodiments, the material of the light extraction layer 5 needs to have a small extinction coefficient in visible light, specifically less than 0.1 at a wavelength of 430 nm; preferably, less than 0.003; more preferably, less than 0.001. This results in high transmittance of visible light, reducing the impact on the light extraction efficiency of the device.

[0099] In some embodiments, the organic functional layer 3 further includes at least one of an electron injection layer 3e, an electron transport layer 3d, a hole injection layer 3a, and a hole transport layer 3b.

[0100] In some embodiments, the organic light-emitting device 100 further includes a substrate 1 located on the side of the anode 2 away from the organic functional layer 3.

[0101] In some embodiments, the organic light-emitting device 100 is selected from one of organic light-emitting diodes (OLEDs), organic photovoltaic cells, organic light-emitting cells, organic field-effect transistors, organic light-emitting field-effect transistors, organic lasers, organic spintronic devices, organic sensors, and organic plasmon emission diodes.

[0102] It is understood that the organic light-emitting device 100 in the embodiments of this application is not limited to the examples above.

[0103] In some embodiments, the organic light-emitting device 100 is selected from OLEDs.

[0104] In one specific embodiment, the organic light-emitting device 100 includes a substrate 1, an anode 2, a hole injection layer 3a, a hole transport layer 3b, a light-emitting layer 3c, an electron transport layer 3d, an electron injection layer 3e, a cathode 4, and a light extraction layer 5, which are stacked sequentially.

[0105] The following describes the device structure of the electroluminescent device, including the cathode 4, anode 2, and light extraction layer 5, but is not limited to this description.

[0106] Anode 2 may comprise a conductive metal or metal oxide, or a conductive polymer. Holes can be readily injected into hole injection layer 3a (HIL), hole transport layer 3b (HTL), or light-emitting layer 3c. In one embodiment, the absolute value of the difference between the work function of anode 2 and the HOMO level or valence band level of the light emitter in light-emitting layer 3c, or the p-type semiconductor material serving as HIL, 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 2 materials include, but are not limited to, Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO, aluminum-doped zinc oxide (AZO), etc. Other suitable anode 2 materials are known and can be readily selected by those skilled in the art. Anode 2 materials 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 2 is patterned. The patterned ITO conductive substrate 1 is commercially available and can be used to fabricate devices according to the present invention.

[0107] The cathode 4 may comprise a conductive metal or metal oxide. Electrons can be readily injected into the EIL or ETL or directly into the light-emitting layer. In one embodiment, the absolute value of the difference between the work function of the cathode 4 and the LUMO level or conduction band level of the luminescent material in the light-emitting layer, or the n-type semiconductor material serving as the electron injection layer 3e (EIL), electron transport layer 3d (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 suitable for use as the cathode 4 in an OLED can be used as the cathode 4 material in the device of the present invention. Examples of cathode 4 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, etc. The cathode 4 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.

[0108] The light extraction layer 5 has a suitable energy level structure, exhibiting strong absorption in the region with wavelengths less than 400 nm, while showing weak or near-zero absorption for visible light with wavelengths greater than 400 nm. This prevents damage to the internal materials of the device from high-energy light irradiation during subsequent processes. Simultaneously, the light extraction layer 5 possesses a high refractive index, enabling beneficial extraction of visible light emission and improving the luminous efficiency of the organic light-emitting device. When the reflectivity of the interface between the light extraction layer 5 and adjacent electrodes is high, the influence of light interference is significant. Therefore, the refractive index of the material constituting the light extraction layer 5 is preferably greater than that of the adjacent electrodes, typically above 1.50 at 630 nm, more preferably above 1.70, and particularly preferably above 1.80.

[0109] In some embodiments, the thickness of the light extraction layer 5 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.

[0110] The organic light-emitting device 100 provided in this application contains a light extraction layer 5 of the aromatic amine compound described in the aforementioned embodiments. The aromatic amine compound contains a multi-component fused heterocycle, namely benzo[k]oxy / thioxanthracene or benzo[4,5-bcd]furan / thiophene. This aromatic amine compound has a high first singlet excitation energy level, and because it has a large conjugated planar structure containing oxygen or sulfur atoms, it exhibits a high refractive index. Therefore, when the aromatic amine compound of this application is applied to the light extraction layer 5 of the electronic device, it can not only avoid over-absorption of light emitted by the device, but also significantly improve the light extraction efficiency, thereby optimizing the performance of the organic light-emitting device 100.

[0111] This application also relates to the application of the organic light-emitting device 100 according to this application in various electronic devices, including, but not limited to, display devices, lighting devices, light sources, sensors, etc.

[0112] This application also provides a display panel, which includes the organic light-emitting device 100 of the foregoing embodiments.

[0113] In some embodiments, the display panel further includes an array substrate and an encapsulation layer, wherein the organic light-emitting device 100 is located on the array substrate and electrically connected to the array substrate, and the encapsulation layer covers the array substrate and the encapsulation layer.

[0114] It is understood that the array substrate is used to drive the organic light-emitting device 100, and the encapsulation layer is used to protect the organic light-emitting device 100.

[0115] In some embodiments, the display panel further includes a cover plate and an optical film, the optical film being located between the encapsulation layer and the cover plate; wherein the optical film includes at least one of a polarizer, a light conversion layer, and a color filter.

[0116] The display panel provided in this application embodiment includes the organic light-emitting device 100 of the aforementioned embodiment, which contains a light extraction layer 5 comprising the aforementioned aromatic amine compound. Because the first singlet excited state energy level of the aromatic amine compound used to prepare the light extraction layer is high, it can effectively prevent light emitted by the device. Furthermore, due to its large conjugated planar structure containing oxygen or sulfur atoms, it exhibits a high refractive index. Therefore, when the aromatic amine compound of this application is applied to the light extraction layer 5 of the organic light-emitting device 100, the organic light-emitting device 100 has high luminous efficiency, thereby improving the performance of the display panel of this application.

[0117] The organic compounds provided in this application will be described below with reference to preferred embodiments. However, the organic compounds provided in this application are not limited to the following embodiments. It should be understood that the appended claims summarize the scope of this application. Under the guidance of the concept of this application, those skilled in the art should realize that any changes made to the various embodiments of this application will be covered by the spirit and scope of the claims of this application. Specific Implementation

[0119] It is understood that the compounds of this application are synthesized according to the synthesis methods of the following embodiments, but the compounds of this application are not limited to the following embodiments.

[0120] Example 1

[0121] This embodiment provides a method for synthesizing compound M1, and the synthetic route is shown below:

[0122]

[0123] Synthesis of compound M1:

[0124] Compound 1-1 (10 mmol), compound 1-2 (10 mmol), Pd2(dba)3 (0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in xylene and stirred at 140 °C for 6 h under a nitrogen atmosphere. After the reaction system cooled, some of the xylene solvent was removed by rotary evaporation, and the mixture was extracted with dichloromethane and water and separated. The resulting organic phase was dried by rotary evaporation to obtain the crude product. The crude product was stirred overnight at 100 °C with toluene solvent, filtered, and dried to obtain compound M1 in 87% yield. The mass spectrometry was [m / z [H]]. += 619. Elemental analysis: Calculated values: C, 81.41; H, 4.07; N, 6.78; O, 7.75; Test values: C, 81.55; H, 4.17; N, 6.68; O, 7.67.

[0125] Example 2

[0126] This embodiment provides a method for synthesizing compound M2, and the synthetic route is shown below:

[0127]

[0128] Compound M2 was synthesized using the same method as compound M1 described above, with a yield of 84% and a mass spectrometry result of m / z [H]. + =651. Elemental analysis: Calculated values: C, 77.39; H, 3.87; N, 6.45; O, 2.45; S, 9.84; Test values: C, 77.29; H, 3.67; N, 6.58; O, 2.65; S, 9.80.

[0129] Example 3

[0130] This embodiment provides a method for synthesizing compound M3, and the synthetic route is shown below:

[0131]

[0132] Compound M3 was synthesized using the same method as compound M1 described above, with a yield of 84% and a mass spectrometry result of m / z [H]. + =635. Elemental analysis: Calculated values: C, 79.35; H, 3.96; N, 6.61; O, 5.03; S, 5.04; Test values: C, 79.30; H, 3.92; N, 6.65; O, 5.08; S, 5.02.

[0133] Example 4

[0134] This embodiment provides a method for synthesizing compound M4, and the synthetic route is shown below:

[0135]

[0136] Compound M4 was synthesized using the same method as compound M1 described above, with a yield of 86% and a mass spectrometry value of m / z [H]. +=593. Elemental analysis: Calculated values: C, 80.93; H, 3.91; N, 7.08; O, 8.09; Test values: C, 80.83; H, 3.96; N, 7.18; O, 8.02.

[0137] Example 5

[0138] This embodiment provides a method for synthesizing compound M5, and the synthetic route is shown below:

[0139]

[0140] Synthesis of intermediate 5-3:

[0141] Compounds 5-1 (10 mmol), 5-2 (10 mmol), and Pd(PPh3)4 (0.1 mmol) were dissolved in a mixed solvent of toluene, ethanol, and water, and stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted, washed with water, and separated. The organic phase was then subjected to column chromatography and recrystallized to give intermediate 5-3 in 81% yield. The mass spectrometry result was [m / z] [H]. + = 328.

[0142] Compound M5 was synthesized using the same method as compound M1 described above, with a yield of 84% and a mass spectrometry result of m / z [H]. + =695. Elemental analysis: Calculated values: C, 82.86; H, 4.20; N, 6.04; O, 6.90; Test values: C, 82.81; H, 4.25; N, 6.02; O, 6.80.

[0143] Example 6

[0144] This embodiment provides a method for synthesizing compound M6, and the synthetic route is shown below:

[0145]

[0146] Compound M6 was synthesized using the same method as compound M1 described above, with a yield of 83% and a mass spectrometry result of m / z [H]. + =727. Elemental analysis: Calculated values: C, 79.20; H, 4.02; N, 5.77; O, 2.20; S, 8.81; Test values: C, 79.25; H, 4.07; N, 5.72; O, 2.15; S, 8.87.

[0147] Example 7

[0148] This embodiment provides a method for synthesizing compound M7, and the synthetic route is shown below:

[0149]

[0150] Intermediate 7-3 was synthesized using the same method as intermediate 5-3 described above, with a yield of 81% and a mass spectrometry result of m / z [H]. + =329.

[0151] Compound M7 was synthesized using the same method as compound M1 described above, with a yield of 82% and a mass spectrometry value of m / z [H]. + =696. Elemental analysis: Calculated values: C, 81.02; H, 4.05; N, 8.04; O, 6.89; Test values: C, 81.11; H, 4.12; N, 8.03; O, 6.79.

[0152] Example 8

[0153] This embodiment provides a method for synthesizing compound M8, and the synthetic route is shown below:

[0154]

[0155] Compound M8 was synthesized using the same method as compound M1 described above, with a yield of 82% and a mass spectrometry result of m / z [H]. + =621. Elemental analysis: Calculated values: C, 77.28; H, 3.73; N, 11.27; O, 7.72; Test values: C, 77.22; H, 3.77; N, 11.22; O, 7.71.

[0156] Example 9

[0157] This embodiment provides a method for synthesizing compound M9, and the synthetic route is shown below:

[0158]

[0159] Compound M9 was synthesized using the same method as compound M1 described above, with a yield of 85% and a mass spectrometry result of m / z [H]. + =619. Elemental analysis: Calculated values: C, 81.41; H, 4.07; N, 6.78; O, 7.75; Test values: C, 81.31; H, 4.15; N, 6.72; O, 7.65.

[0160] Example 10

[0161] This embodiment provides a method for synthesizing compound M10, and the synthetic route is shown below:

[0162]

[0163] Compound M10 was synthesized using the same method as compound M1 described above, with a yield of 82% and a mass spectrometry value of m / z [H]. + =593. Elemental analysis: Calculated values: C, 80.93; H, 3.91; N, 7.08; O, 8.09; Test values: C, 80.91; H, 3.81; N, 7.18; O, 8.14.

[0164] Example 11

[0165] This embodiment provides a method for synthesizing compound M11, and the synthetic route is shown below:

[0166]

[0167] Intermediate 11-3 was synthesized using the same method as compound M1 described above, with a yield of 84% and a mass spectrometry result of m / z [H]. + =426.

[0168] Compound M11 was synthesized using the same method as compound M1 described above, with a yield of 82% and a mass spectrometry value of m / z [H]. + =619. Elemental analysis: Calculated values: C, 81.41; H, 4.07; N, 6.78; O, 7.75; Test values: C, 81.35; H, 4.17; N, 6.73; O, 7.72.

[0169] Example 12

[0170] This embodiment provides a method for synthesizing compound M12, and the synthetic route is shown below:

[0171]

[0172] Compound M12 was synthesized using the same method as compound M1 described above, with a yield of 84% and a mass spectrometry value of m / z [H]. + =695. Elemental analysis: Calculated values: C, 82.86; H, 4.20; N, 6.04; O, 6.90; Test values: C, 82.56; H, 4.21; N, 6.14; O, 6.93.

[0173] Example 13

[0174] This embodiment provides a method for synthesizing compound M13, and the synthetic route is shown below:

[0175]

[0176] Compound M13 was synthesized using the same method as compound M1 described above, with a yield of 82% and a mass spectrometry value of m / z [H]. + =604. Elemental analysis: Calculated values: C, 81.44; H, 4.00; N, 9.27; O, 5.29; Test values: C, 81.40; H, 4.02; N, 9.22; O, 5.36.

[0177] Example 14

[0178] This embodiment provides a method for synthesizing compound M14, and the synthetic route is shown below:

[0179]

[0180] The synthesis of intermediate 14-3 was performed using the same method as intermediate 5-3 described above, with a yield of 81% and a mass spectrometry result of m / z[H+] = 319.

[0181] Compound M14 was synthesized using the same method as compound M1 described above, with a yield of 84% and a mass spectrometry value of m / z[H+] = 709. Elemental analysis: calculated values: C, 81.23; H, 3.83; N, 5.92; O, 9.02; measured values: C, 81.25; H, 3.87; N, 5.91; O, 9.12.

[0182] Example 15

[0183] This embodiment provides a method for synthesizing compound M15, and the synthetic route is shown below:

[0184]

[0185] Compound M15 was synthesized using the same method as compound M1 described above, with a yield of 84% and a mass spectrometry result of m / z [H]. + =642. Elemental analysis: Calculated values: C, 84.10; H, 4.08; N, 4.36; O, 7.47; Test values: C, 84.11; H, 4.06; N, 4.38; O, 7.49.

[0186] Example 16

[0187] This embodiment provides a method for synthesizing compound M16, and the synthetic route is shown below:

[0188]

[0189] Compound M16 was synthesized using the same method as compound M1 described above, with a yield of 81% and a mass spectrometry value of m / z [H]. +=692. Elemental analysis: Calculated values: C, 84.95; H, 4.07; N, 4.04; O, 6.93; Test values: C, 84.91; H, 4.17; N, 4.10; O, 6.89.

[0190] Example 17

[0191] This embodiment provides a method for synthesizing compound M17, and the synthetic route is shown below:

[0192]

[0193] Intermediate 17-2 was synthesized using the same method as intermediate 5-3 described above, with a yield of 83% and a mass spectrometry result of m / z [H]. + =352.

[0194] Compound M17 was synthesized using the same method as compound M1 described above, with a yield of 84% and a mass spectrometry value of m / z [H]. + =719. Elemental analysis: Calculated values: C, 83.43; H, 4.06; N, 5.84; O, 6.67; Test values: C, 83.41; H, 4.08; N, 5.88; O, 6.69.

[0195] Energy structures of organic compounds M1-M17

[0196] This application's embodiments test the extinction coefficient at 430 nm, the refractive index at 630 nm, and the singlet first excited state (S1) of compounds M1-M16 synthesized in Examples 1-17 and the comparative compound Ref-01. The chemical structure of Ref-01 is as follows:

[0197]

[0198] The energy levels of organic materials can be obtained through quantum computing, such as using TD-DFT (time-dependent density functional theory) via Gaussian09W (Gaussian Inc.). For specific simulation methods, please refer to WO2011141110. First, the molecular geometry is optimized using the semi-empirical method "Ground State / DFT / Default Spin / B3LYP / 6-31G(d)" (Charge 0 / Spin Singlet). The energy structure of the organic molecule is calculated by TD-DFT (time-dependent density functional theory) to obtain "TD-SCF / DFT / Default Spin / B3PW91" and basis set "6-31G(d)" (Charge 0 / Spin Singlet).

[0199] The compound was deposited onto single-crystal silicon by vacuum evaporation to form a 50 nm thin film. The single-crystal silicon was placed on the sample stage of an ellipsometer (ES-01) with an incident angle of 70°. The test was conducted in an atmospheric environment. The extinction coefficient (k) and refractive index (n) of the compound were obtained from the ellipsometer.

[0200] The results are shown in Table 1.

[0201] Table 1

[0202]

[0203] As can be seen from Table 1, the aromatic amine compounds containing multiple fused heterocycles involved in the embodiments of this application have a high S1, which can more effectively avoid absorbing the light emitted by the device.

[0204] Furthermore, compared to Ref-01, the compound of this application has a higher refractive index, which ensures better light extraction and optimizes device performance.

[0205] Application Examples

[0206] Application Example 1

[0207] This application embodiment provides an organic light-emitting device 100, and the structure of the organic light-emitting device 100 is referenced. Figure 1 As shown, the structure includes a substrate 1, an anode 2, a hole injection layer 3a, a hole transport layer 3b, a light-emitting layer 3c, an electron transport layer 3d, an electron injection layer 3e, a cathode 4, and a light extraction layer 5, stacked sequentially. The specific structure is ITO / Ag / ITO (anode) / HATCN / HT / m-CP:Ir(p-ppy)3 / ET / LiF / Mg:Ag / light extraction layer, where the structural formulas of the compounds involved are shown below:

[0208]

[0209] This application embodiment also provides a method for fabricating the above-mentioned organic light-emitting device 100, including the following steps:

[0210] The ITO conductive glass anode layer was cleaned, followed by ultrasonic cleaning with deionized water, acetone, and isopropanol for 15 minutes, and then treated in a plasma cleaner for 5 minutes to improve the electrode work function. A hole injection layer material, HATCN, with a thickness of 5 nm was deposited on the ITO anode layer via vacuum evaporation at a deposition rate of 1 Å / s. A hole transport material, HT, with a thickness of 80 nm was deposited on the hole injection layer via vacuum evaporation. A light-emitting layer, using m-CP as the host material and Ir(p-ppy)3 as the dopant material at a mass ratio of 1:9, with a thickness of 30 nm, was deposited on top of the hole transport layer. An electron transport material, ET, with a thickness of 30 nm was deposited on top of the light-emitting layer via vacuum evaporation. An electron injection layer, LiF, with a thickness of 1 nm, was deposited on top of the electron transport layer via vacuum evaporation. Finally, a cathode Mg:Ag layer with a doping ratio of 9:1 and a thickness of 15 nm was deposited on top of the electron injection layer via vacuum evaporation. On top of the cathode layer, a light extraction layer compound M1 with a thickness of 60 nm was deposited by vacuum evaporation.

[0211] Application Examples 2-17

[0212] Application Examples 2-17 provide organic light-emitting devices 2-17, with the same structure and preparation method as Application Example 1. The difference is that the light extraction layer material is replaced as shown in Table 2.

[0213] Comparative Application Example 1

[0214] Comparative Application Example 1 provides an organic light-emitting device comparison device Ref-01, whose structure and fabrication method are the same as those in Application Example 1, except that the light extraction layer material is replaced with Ref-01.

[0215] The performance test results of organic light-emitting devices 1~17 and the comparative device Ref-01 are shown in Table 2.

[0216] Table 2

[0217]

[0218] It is understandable that the luminous efficiency in Table 2 is based on a current density of 10 mA / cm². 2 Data obtained at that time.

[0219] As shown in Tables 1 and 2, compared to the comparative device Ref-01, the organic light-emitting devices 1-17 use compounds M1-M17 as the light extraction layer materials. Compounds M1-M17 are aromatic amine compounds containing multiple fused heterocyclic rings, namely benzo[k]oxy / thioxanthracene or benzo[4,5-bcd]furan / thiophene. Because they possess a large first singlet excitation energy level, they avoid absorbing energy levels in organic light-emitting devices. Furthermore, due to their large conjugated planar structure containing oxygen or sulfur atoms, they exhibit a high refractive index. Therefore, when applied to organic light-emitting devices 1-17, the luminous efficiency reaches 115 cd / A or higher.

[0220] The foregoing has provided a detailed description of an aromatic amine compound, mixture, organic light-emitting device, and display panel provided in the embodiments of this application. Specific examples have been used to illustrate the principles and implementation methods of this application. The descriptions of the above embodiments are only for the purpose of helping to understand the methods and core ideas of this application. At the same time, for those skilled in the art, there will be changes in the specific implementation methods and application scope based on the ideas of this application. Therefore, the content of this specification should not be construed as a limitation of this application.

Claims

1. An aromatic amine compound, characterized in that, The aromatic amine compound is selected from any compound represented by any one of the structural formulas (1) to (2): X is selected from oxygen or sulfur atoms, and Ar1 is selected from any of the following groups: ， L1 is selected from one of single bond, divalent phenyl, and divalent pyridyl; L2 is selected from divalent phenyl; L3 is selected from one of single bond, divalent phenyl, divalent benzoxazolyl, and divalent diphenyl; Ar2 is selected from phenyl, benzoxazolyl, benzothiazolyl, and... One of o-phenanthroline, naphthobenzofuran, and phenanthrobenzofuran; Indicates the connection site.

2. The aromatic amine compound according to claim 1, characterized in that, The L3 is independently selected from a single bond or any of the following groups: 。 3. The aromatic amine compound according to claim 1, characterized in that, The Ar2 group is selected from any of the following groups: 。 4. An aromatic amine compound, characterized in that, The aromatic amine compound is selected from any one of the following compounds: 。 5. A mixture, characterized in that, It includes at least one aromatic amine compound as described in any one of claims 1 to 4, and an organic functional material, wherein the organic functional material is selected from at least one of hole injection materials, hole transport materials, light-emitting auxiliary materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, organic light-emitting guest materials, and organic host materials.

6. An organic light-emitting device, characterized in that, The organic light-emitting device includes: anode; The cathode is disposed opposite to the anode; An organic functional layer is located between the anode and the cathode, and the organic functional layer includes a light-emitting layer; and, A light extraction layer is located on the side of the cathode away from the organic functional layer, the light extraction layer comprising an aromatic amine compound as described in any one of claims 1 to 4, or the light extraction layer comprising a mixture as described in claim 5.

7. A display panel, characterized in that, The display panel includes the organic light-emitting device as described in claim 6.

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