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

Abstract

The invention relates to an organic compound, a composition, an optical film, an organic light-emitting device and a display panel. The organic compound has a structure represented by a general formula (1), the organic compound represented by the formula (1) has a high refractive index, and can effectively improve the luminous efficiency of the organic light-emitting device when applied to a covering layer of the organic light-emitting device.

Description

TECHNICAL FIELD

[0001] The present application relates to the technical field of display, in particular to an organic compound, a composition, an optical film, an organic light-emitting device and a display panel. BACKGROUND

[0002] Organic light-emitting display (OLED) is an advanced self-luminous display technology, which produces excitons through the transfer and recombination of carriers between different functional layers, and the excitons emit light through high quantum efficiency organic compounds or metal complexes. OLED technology is well-known for its self-luminous, high brightness, high efficiency, high contrast and fast response time.

[0003] In recent years, the light-emitting efficiency of OLED devices has been significantly improved, and the internal quantum efficiency has approached the theoretical limit. Therefore, improving the light extraction efficiency has become the key to further improving the stability and current efficiency of the device. For example, by optimizing the accumulation of the emitting layer metal complex and the matching of the refractive index between the functional layers, the light extraction efficiency can be effectively improved. In 2001, researchers Hung et al. coated a layer of about 50 nanometer thick organic or inorganic compound on the surface of the metal cathode, and improved the device performance by precisely controlling the thickness and refractive index. In 2003, Riel et al. tried to evaporate an inorganic compound ZnSe with a high refractive index (n = 2.6) on the cathode, and used the difference in refractive index between the functional layers to improve the light extraction efficiency. However, due to the high evaporation temperature and slow evaporation rate of inorganic materials, the application of such compounds in OLED devices has been limited.

[0004] In view of these challenges, researchers have begun to explore organic compounds as cover layer materials, but the existing organic compounds have low refractive index, which limits their application in organic light-emitting devices.

[0005] Therefore, it is urgent to develop new organic cover layer materials to solve the above problems. SUMMARY

[0006] The present application provides an organic compound, a composition, an optical film, an organic light-emitting device and a display panel, the organic compound of the present application has a high refractive index, and when applied to the cover layer of an organic light-emitting device, it can effectively improve the light-emitting efficiency of the organic light-emitting device.

[0007] The present application provides an organic compound, the organic compound has a structure represented by general formula (1): (1); wherein, X is selected from O or S; Y is selected from at least one of CH and N; L1 is selected from at least one of single bond, phenyl, biphenyl, naphthyl, benzofuranyl, benzothiophenyl, and pyridyl; L2 is selected from at least one of single bond, phenyl, biphenyl, naphthyl, benzofuranyl, benzothiopheneyl, and pyridyl, wherein L2 is associated with a group They are either independent of each other or overlapped with each other; L3 is selected from at least one of a single bond, an aromatic group having 6 to 30 carbon atoms, and a heteroaromatic group having 5 to 30 carbon atoms; Ar1 is selected from at least one of hydrogen atoms, aromatic groups having 6 to 30 carbon atoms, and heteroaromatic groups having 5 to 30 carbon atoms.

[0008] Accordingly, this application also provides a composition comprising at least one organic solvent and at least one organic compound as described above.

[0009] Accordingly, this application also provides an optical film, the material of which includes at least one organic compound as described above, or is prepared from a composition as described above.

[0010] Accordingly, this application also provides an organic light-emitting device, the organic light-emitting device comprising: First electrode; An organic functional layer is disposed on one side of the first electrode; The second electrode is disposed on the side of the organic functional layer away from the first electrode; A capping layer is disposed on the side of the second electrode away from the organic functional layer. The material of the capping layer includes at least one organic compound as described above, or the capping layer is prepared from the composition as described above, or the capping layer includes an optical film as described above.

[0011] Accordingly, this application also provides a display panel, which includes the organic light-emitting device as described above.

[0012] This application provides an organic compound, composition, optical film, organic light-emitting device, and display panel. The organic compound provided in this application is an aromatic amine compound with pyrene and thiophene / furan fused-ring groups as its core structure. First, the introduction of pyrene, with its highly conjugated planar skeleton, effectively promotes intermolecular π-π stacking, improving the rigidity and close packing of the material structure, thereby achieving high polarizability and higher refractive index. Furthermore, the electron-rich pyrene and thiophene / furan fused-ring groups can also reduce the introduction of electron-withdrawing groups such as those containing thiazole / oxazole heterocycles to a certain extent, effectively regulating intramolecular charge transport effects and avoiding significant absorption in the visible light region, thus affecting light extraction efficiency. Therefore, when the aromatic amine compound provided in this application is used as a capping layer in a light-emitting device, it not only effectively improves the refractive index of the capping layer but also reduces absorption in the visible light region, thereby improving the light extraction efficiency of the electronic device and achieving an electronic device with excellent performance. Attached Figure Description

[0013] 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.

[0014] Figure 1 This is a schematic diagram of a light-emitting device structure provided in an embodiment of this application; Figure 2 This is a schematic diagram of the structure of a display panel provided in an embodiment of this application; Figure 3 This is the 1H NMR spectrum of compound M3 synthesized in the embodiments of this application; Figure 4 This is the 1H NMR spectrum of compound M4 synthesized in the embodiments of this application.

[0015] Explanation of reference numerals in the attached figures: 100. Display panel; 10. Light-emitting device; 1. Substrate; 2. First electrode; 3. Organic functional layer; 31. Hole injection layer; 32. Hole transport layer; 33. Light-emitting layer; 34. Electron transport layer; 35. Electron injection layer; 4. Second electrode; 5. Cover layer; 20. Array substrate; 30. Encapsulation layer; 40. Cover plate; 50. Optical film. Detailed Implementation

[0016] 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.

[0017] In this application, hydrogen atoms include isotopes with different numbers of neutrons, namely protium, deuterium, and tritium.

[0018] In this application, aromatic groups, aromatic families, and aromatic ring systems have the same meaning and can be used interchangeably.

[0019] In this application, heteroaromatic groups, heteroaromatic families, and heteroaromatic ring systems have the same meaning and can be used interchangeably.

[0020] In this application, "substitution" means that the hydrogen atom in the substituent is replaced by the substituent.

[0021] In this application, when the same substituent appears multiple times, it can be independently selected from different groups. If the general formula contains multiple R, then R can be independently selected from different groups.

[0022] 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 the defined group can be substituted by one or more substituents R, wherein R is selected from, but is not limited to: deuterium, cyano, isocyano, nitro or halogen, alkyl containing 1-20 carbon atoms, heterocyclic group containing 3-20 ring atoms, aromatic group containing 6-20 ring atoms, heteroaromatic group containing 5-20 ring atoms, -NR'R'', silyl, carbonyl, alkoxycarbonyl, aryloxycarbonyl, carbamoyl, halocarbamoyl, etc. Formyl, isocyanate, thiocyanate, isothiocyanate, hydroxyl, trifluoromethyl, and the above groups may be further substituted by substituents acceptable in the art; it is understood that R' and R'' in -NR'R'' are independently selected from, but not limited to: H, deuterium, cyano, isocyano, nitro or halogen, alkyl containing 1-10 carbon atoms, heterocyclic group containing 3-20 ring atoms, aromatic group containing 6-20 ring atoms, and heteroaromatic group containing 5-20 ring atoms. Preferably, R is selected from, but not limited to: deuterium, cyano, isocyano, nitro or halogen, alkyl containing 1-10 carbon atoms, heterocyclic group containing 3-10 ring atoms, aromatic group containing 6-20 ring atoms, heteroaromatic group containing 5-20 ring atoms, silyl, carbonyl, alkoxycarbonyl, aryloxycarbonyl, carbamoyl, halocarbamoyl, formyl, isocyanate group, thiocyanate group, isothiocyanate group, hydroxyl, trifluoromethyl, and the above groups may also be further substituted with substituents acceptable in the art.

[0023] 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, the benzene ring has 6 ring atoms, the naphthalene ring has 10 ring atoms, and the thiophene group has 5 ring atoms.

[0024] In this application, "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, and for polycyclic rings, at least one of them is an aromatic ring system. For example, "substituted or unsubstituted aryl having 6 to 40 ring atoms" refers to an aryl containing 6 to 40 ring atoms, preferably a substituted or unsubstituted aryl having 6 to 30 ring atoms, more preferably a substituted or unsubstituted aryl having 6 to 18 ring atoms, and particularly preferably a substituted or unsubstituted aryl having 6 to 14 ring atoms, and optionally further substituted on the aryl group; suitable examples include, but are not limited to: phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, fluoranyl, triphenylene, pyrene, perylene, tetraphenyl, fluorenyl, dinaphthylphenyl, acenaphthyl and their derivatives. It is understandable that multiple aryl groups can also be interrupted by short non-aromatic units (e.g., <10% non-H atoms, such as C, N or O atoms), specifically acenaphthene, fluorene, or 9,9'-diarylfluorene, triarylamine, and diaryl ether systems should also be included in the definition of aryl.

[0025] In this application, "heteroaryl or heteroaromatic group" refers to an aryl group in which at least one carbon atom is replaced by a non-carbon atom, which can be an N atom, an O atom, an S atom, etc. For example, "substituted or unsubstituted heteroaryl group having 5 to 40 ring atoms" refers to a heteroaryl group having 5 to 40 ring atoms, preferably a substituted or unsubstituted heteroaryl group having 6 to 30 ring atoms, more preferably a substituted or unsubstituted heteroaryl group having 6 to 18 ring atoms, and particularly preferably a substituted or unsubstituted heteroaryl group having 6 to 14 ring atoms. The heteroaryl group may optionally be further substituted, and suitable examples include, but are not limited to, thiophene, furanyl, pyrrole, imidazolyl, diazolyl, triazolyl, imidazolyl, pyridyl, bipyridyl, and pyrimidine. Triazinyl, acridineyl, pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridinylpyrimidinyl, pyridinylpyrazinyl, benzothiopheneyl, benzofuranyl, indolyl, pyrroloimidazolyl, pyrrolopyrrolyl, thienopyrrolyl, thienopyrrolyl, furanolyl, furanolyl, thienofuranyl, benzoisoxazolyl, benzoisothiazolyl, benzoimidazolyl, o-diazonyl, phenanthridineyl, primidyl, quinazolinoneyl, dibenzothiopheneyl, dibenzofuranyl, carbazoleyl and their derivatives.

[0026] 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 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. 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-butyl... Pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, 3 7-Dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl, n-undecyl, n-dodecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, n-tridecyl, n-tetradecyl, n-pentadecanyl, n-hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, n-hepta ...

[0027] In this application, "amino group" refers to an amine derivative having the structural feature of the formula -N(X)2, wherein each "X" is independently H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, etc. Non-limiting types of amino groups include -NH2, -N(alkyl)2, -NH(alkyl), -N(cycloalkyl)2, -NH(cycloalkyl), -N(heterocyclic)2, -NH(heterocyclic), -N(aryl)2, -NH(aryl), -N(alkyl)(aryl), -N(alkyl)(heterocyclic), -N(cycloalkyl)(heterocyclic), -N(aryl)(heteroaryl), -N(alkyl)(heteroaryl), etc.

[0028] In this application, unless otherwise defined, hydroxyl refers to -OH, carboxyl refers to -COOH, carbonyl refers to -C(=O)-, amino refers to -NH2, formyl refers to -C(=O)H, haloformyl refers to -C(=O)Z (where Z represents halogen), carbamoyl refers to -C(=O)NH2, isocyanate refers to -NCO, and isothiocyanate refers to -NCS.

[0029] In this application, the term "alkoxy" refers to a group with the structure "-O-alkyl", that is, an alkyl group as defined above that is attached to other groups via an oxygen atom. Suitable examples of phrases containing this term include, but are not limited to: methoxy (-O-CH3 or -OMe), ethoxy (-O-CH2CH3 or -OEt), and tert-butoxy (-OC(CH3)3 or -OtBu).

[0030] In this application, the "*" connected to a single bond indicates a connection or fusion site.

[0031] 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.

[0032] In this application, when no fusion site is specified in the group, it means that any fusionable site in the group is selected as the fusion site, preferably two or more sites in the adjacent position of the group are fusion sites.

[0033] In this application, when the same group contains multiple substituents with the same symbol, the substituents can be the same as or different from each other, for example... The six Rs on the benzene ring can be the same or different from each other.

[0034] In this application, the single bonds connecting the substituents extend 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; such as express Can be with A fused ring can be formed at any position on the benzene ring.

[0035] The terms cycloalkyl or cycloalkyl as used in this application have the same meaning and are interchangeable.

[0036] This application provides an organic compound having the structure shown in general formula (1): (1); in, X is selected from O or S; Y is selected from at least one of CH and N, and multiple Ys are selected from the same or different groups; L1 is selected from at least one of single bond, phenyl, biphenyl, naphthyl, benzofuranyl, benzothiophenyl, and pyridyl; L2 is selected from at least one of single bond, phenyl, biphenyl, naphthyl, benzofuranyl, benzothiophenyl, and pyridyl, wherein in the structure of formula (1), L2 and the group attached thereto... They can be independent of each other or overlapped with each other; L3 is selected from at least one of a single bond, an aromatic group having 6 to 30 carbon atoms, and a heteroaromatic group having 5 to 30 carbon atoms; Ar1 is selected from at least one of hydrogen atoms, aromatic groups having 6 to 30 carbon atoms, and heteroaromatic groups having 5 to 30 carbon atoms.

[0037] In some embodiments, L3 is selected from at least one of single bond, phenyl, biphenyl, naphthyl, and pyridyl.

[0038] In some embodiments, Ar1 is selected from at least one of hydrogen atom, pyridyl, naphthyl, benzofuranyl, benzothiophene, benzooxazolyl, benzothiazolyl, oxazolopyridyl, thiazopyridyl, furan-pyridyl, thiophene-pyridyl, phenanthryl, anthracene, benzophenanthryl, o-phenanthrolinel, dibenzofuranyl, dibenzothiophene, quinolinyl, quinoxalinyl, naphthobenzofuranyl, naphthobenzothiophene, phenanthrylbenzofuranyl, and triphenylene.

[0039] In some embodiments, the organic compound is selected from any of the following structures:

[0040]

[0041]

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[0097] ; It is understood that the organic compounds in the embodiments of this application include, but are not limited to, the examples given above.

[0098] The organic compounds provided in this application are aromatic amine compounds with pyrene and thiophene / furan fused-ring groups as their core structures. Firstly, the introduction of pyrene, with its highly conjugated planar framework, effectively promotes intermolecular π-π stacking, enhancing the rigidity and close packing of the material structure, thereby achieving high polarizability and a higher refractive index. Furthermore, the electron-rich pyrene and thiophene / furan fused-ring groups can also reduce the introduction of electron-withdrawing groups such as those containing thiazole / oxazole heterocycles, effectively regulating intramolecular charge transport effects and preventing significant absorption in the visible light region, which would affect light extraction efficiency. Therefore, when the aromatic amine compounds provided in this application are used as a capping layer in light-emitting devices, they not only effectively increase the refractive index of the capping layer but also reduce absorption in the visible light region, thereby improving the light extraction efficiency of electronic devices and achieving electronic devices with excellent performance.

[0099] In some embodiments, the organic compounds provided in this application have a high glass transition temperature, and thus high stability. 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.

[0100] In some embodiments, the refractive index of the organic compound for light with a wavelength of 620 nm is greater than or equal to 1.75; preferably, the refractive index of the organic compound for light with a wavelength of 620 nm is greater than or equal to 1.8; more preferably, the refractive index of the organic compound for light with a wavelength of 620 nm is greater than or equal to 1.85.

[0101] In this embodiment of the application, the method for testing the refractive index of the organic compound is as follows: the compound is deposited on a single crystal silicon by vacuum evaporation to form a 60 nm thin film. The single crystal silicon is placed on the sample stage of an ellipsometer (ES-01) with an incident angle of 70°. The test is conducted in an atmospheric environment. The refractive index (n) test result of the organic compound is obtained from the ellipsometer.

[0102] In some embodiments, the singlet energy (S1) of the organic compound is greater than or equal to 2.7 eV; preferably, the singlet energy (S1) of the organic compound is greater than or equal to 2.8 eV; more preferably, the singlet energy (S1) of the organic compound is greater than or equal to 2.85 eV.

[0103] In some embodiments, the organic compounds provided in this application have a small extinction coefficient for light with wavelengths greater than or equal to 430 nm, and a large extinction coefficient for light with wavelengths less than or equal to 400 nm. The organic compounds of this application have high transmittance for visible light, thereby reducing the impact on the light output efficiency of the device.

[0104] In some embodiments, the extinction coefficient of the organic compound for light with a wavelength of 430 nm is less than 0.1; preferably, the extinction coefficient of the organic compound for light with a wavelength of 430 nm is less than 0.003; more preferably, the extinction coefficient of the organic compound for light with a wavelength of 430 nm is less than 0.001.

[0105] In some embodiments, the extinction coefficient of the organic compound for light with a wavelength of 350 nm is greater than or equal to 0.3; preferably, the extinction coefficient of the organic compound for light with a wavelength of 350 nm is greater than or equal to 0.5; more preferably, the extinction coefficient of the organic compound for light with a wavelength of 350 nm is greater than or equal to 0.7; and most preferably, the extinction coefficient of the organic compound for light with a wavelength of 350 nm is greater than or equal to 1.0.

[0106] In some embodiments, the organic compound can be formed into a film layer for use in OLED devices via a vapor deposition process.

[0107] Wherein, the molecular weight of the organic compound is less than or equal to 1200 g / mol; preferably, the molecular weight of the organic compound is less than or equal to 1100 g / mol; more preferably, the molecular weight of the organic compound is less than or equal to 1000 g / mol; even more preferably, the molecular weight of the organic compound is less than or equal to 950 g / mol; most preferably, the molecular weight of the organic compound is less than or equal to 900 g / mol.

[0108] In some embodiments, the organic compound can be formed into a film layer for use in OLED devices through a printing process.

[0109] Wherein, the molecular weight of the organic compound is greater than or equal to 800 g / mol; preferably, the molecular weight of the organic compound is greater than or equal to 900 g / mol; more preferably, the molecular weight of the organic compound is greater than or equal to 1000 g / mol; even more preferably, the molecular weight of the organic compound is greater than or equal to 1100 g / mol; and most preferably, the molecular weight of the organic compound is greater than or equal to 1200 g / mol.

[0110] In some embodiments, at 25°C, the solubility of the organic compound in toluene is greater than or equal to 2 mg / ml; preferably, the solubility of the organic compound in toluene is greater than or equal to 3 mg / ml; more preferably, the solubility of the organic compound in toluene is greater than or equal to 4 mg / ml; and most preferably, the solubility of the organic compound in toluene is greater than or equal to 5 mg / ml.

[0111] This application also provides a composition comprising at least one organic solvent and at least one organic compound as described in the above embodiments.

[0112] In some embodiments, the organic solvent is selected from one or more of aromatic, heteroaromatic, ester, aromatic ketone, aromatic ether, aliphatic ketone, aliphatic ether, alicyclic, olefinic, borate ester and phosphate ester compounds.

[0113] In some embodiments, the organic solvent is selected from aromatic or heteroaromatic solvents, such as aromatic solvents with aliphatic chain and / or aliphatic ring substitution, aromatic ketone solvents, or aromatic ether solvents.

[0114] In some embodiments, the organic solvent includes 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-methylbenzene, etc. Oxynaphthalene, 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, glycidyl phenyl ether, dibenzyl ether, 4-tert-butylanisole, trans-p-propenylanisole, 1,2-dimethyl... Oxybenzene, 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 solvent: at least one of alkyl octanoate, alkyl sebacate, alkyl stearate, alkyl benzoate, alkyl phenylacetate, alkyl cinnamate, alkyl oxalate, alkyl maleate, alkyl lactone, and alkyl oleate.

[0115] In some embodiments, when the composition provided in this application is an ink, the organic solvent in the composition may be selected from: aliphatic ketones, for example, 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, for example, 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.; In some embodiments, when the composition provided in this application is a printing ink, the at least one organic solvent further includes at least one of the following: 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.

[0116] In some embodiments, the composition provided in this application may be a suspension.

[0117] In some embodiments, the composition provided in this application may be a solution.

[0118] In the compositions provided in the embodiments of this application, the organic compound accounts for a mass percentage greater than or equal to 0.01% and less than or equal to 20% of the composition. For example, the mass content of the organic compound in the composition is 0.01%, 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 19%, or 20%.

[0119] In some embodiments, the organic compound is present in a content ranging from 0.1 wt% to 15 wt% in the composition; preferably, the organic compound is present in a content ranging from 0.2 wt% to 10 wt% in the composition; more preferably, the organic compound is present in a content ranging from 0.25 wt% to 5 wt% in the composition.

[0120] In some embodiments, the compositions provided in this application can also be used as coatings or printing inks and can be used to prepare organic light-emitting devices, particularly preferably by printing or coating methods.

[0121] The printing or coating technologies in this application include inkjet printing, nozzle printing, letterpress printing, screen printing, dip coating, spin coating, doctor blade coating, roller printing, torsional roller printing, offset printing, flexographic printing, rotary printing, spraying, brushing, pad printing, and slot extrusion coating. Gravure printing, nozzle printing, and inkjet printing are preferred. When the composition is a solution or suspension, the composition may further include one or more components, such as at least one of surfactants, lubricants, wetting agents, dispersants, hydrophobic agents, and adhesives, to adjust the viscosity, film-forming properties, and improve adhesion of the composition.

[0122] For details regarding printing technology and its requirements for solutions, such as solvent, concentration, and viscosity, please refer to "Handbook of Print Media: Technologies and Production Methods" edited by Helmut Kipphan, ISBN 3-540-67326-1.

[0123] This application also provides an optical film, the material of which includes the organic compounds described in the foregoing embodiments, or the optical film is prepared from the compositions described in the foregoing embodiments. The optical film has a high refractive index and can be used as a capping layer in organic light-emitting devices to improve the light extraction efficiency of the organic light-emitting devices.

[0124] In some embodiments, the optical film has a refractive index of 1.75 or greater than or equal to 1.75 for light with a wavelength of 620 nm; preferably, the optical film has a refractive index of 1.8 or greater than or equal to 1.85 for light with a wavelength of 620 nm; more preferably, the optical film has a refractive index of 1.85 or greater than or equal to 1.85 for light with a wavelength of 620 nm.

[0125] In some embodiments, the optical film has a small extinction coefficient for light with wavelengths greater than or equal to 430 nm, and a large extinction coefficient for light with wavelengths less than or equal to 400 nm. The optical film of this application has high transmittance for visible light, thereby reducing the impact on the light output efficiency of the device.

[0126] In some embodiments, the extinction coefficient of the optical film for light with a wavelength of 430 nm is less than 0.1; preferably, the extinction coefficient of the optical film for light with a wavelength of 430 nm is less than 0.003; more preferably, the extinction coefficient of the optical film for light with a wavelength of 430 nm is less than 0.001.

[0127] In some embodiments, the extinction coefficient of the optical film for light with a wavelength of 350 nm is greater than or equal to 0.3; preferably, the extinction coefficient of the optical film for light with a wavelength of 350 nm is greater than or equal to 0.5; more preferably, the extinction coefficient of the optical film for light with a wavelength of 350 nm is greater than or equal to 0.7; and most preferably, the extinction coefficient of the optical film for light with a wavelength of 350 nm is greater than or equal to 1.0.

[0128] Please refer to Figure 1 This application also provides an organic light-emitting device 10, comprising: a first electrode 2; an organic functional layer 3 disposed on one side of the first electrode 2; a second electrode 4 disposed on the side of the organic functional layer 3 away from the first electrode 2; and a capping layer 5 disposed on the side of the second electrode 4 away from the organic functional layer 3. The material of the capping layer 5 includes the organic compounds described in the foregoing embodiments, or the capping layer 5 is prepared from the compositions described in the foregoing embodiments, or the capping layer 5 includes the optical film described in the foregoing embodiments.

[0129] In some embodiments, the organic functional layer 3 includes a light-emitting layer 33 and at least one functional layer selected from at least one of a hole injection layer 31, a hole transport layer 32, an electron blocking layer, a hole blocking layer, an electron transport layer 34, and an electron injection layer 35.

[0130] In some embodiments, the hole injection layer 31, the hole transport layer 32, and the electron blocking layer are located between the first electrode 2 and the light-emitting layer 33; the hole blocking layer, the electron transport layer 34, and the electron injection layer 35 are located between the light-emitting layer 33 and the second electrode 4.

[0131] In some embodiments, the organic functional layer 3 includes a hole injection layer 31, a hole transport layer 32, a light-emitting layer 33, an electron transport layer 34, and an electron injection layer 35 stacked sequentially, and the hole injection layer 31 is located between the first electrode 2 and the hole transport layer 32.

[0132] In some embodiments, the organic light-emitting device 10 may include an organic light-emitting diode (OLED), an organic photovoltaic cell, an organic light-emitting cell, an organic field-effect transistor, an organic light-emitting field-effect transistor, an organic laser, an organic spintronic device, an organic sensor, and an organic plasmon emitting diode, etc., and is particularly preferably an organic light-emitting diode.

[0133] It is understood that in the embodiments of this application, one of the first electrode 2 and the second electrode 4 can be the anode and the other can be the cathode. That is, the capping layer 5 can be located on the side of the cathode away from the organic functional layer or on the side of the anode away from the organic functional layer.

[0134] In some embodiments, the first electrode 2 is the anode and the second electrode 4 is the cathode. Correspondingly, the capping layer 5 is located on the side of the second electrode 4 away from the organic functional layer 3.

[0135] In some embodiments, since the capping layer 5 contains the organic compound described in the foregoing embodiments, the organic compound has a high glass transition temperature to improve the thermal stability of the capping layer 5. The glass transition temperature Tg of the organic compound is greater than or equal to 100°C; preferably, the glass transition temperature Tg of the organic compound is greater than or equal to 120°C; more preferably, the glass transition temperature Tg of the organic compound is greater than or equal to 140°C; even more preferably, the glass transition temperature Tg of the organic compound is greater than or equal to 160°C; and most preferably, the glass transition temperature Tg of the organic compound is greater than or equal to 180°C.

[0136] In some embodiments, the material of the capping layer 5 includes the organic compound having a high refractive index. Therefore, the capping layer 5 also has a high refractive index, which helps to improve the light efficiency of the organic light-emitting device 10, especially the external light-emitting efficiency. The capping layer 5 has a refractive index greater than or equal to 1.75 for light with a wavelength of 620 nm. Preferably, the capping layer 5 has a refractive index greater than or equal to 1.8 for light with a wavelength of 620 nm. More preferably, the capping layer 5 has a refractive index greater than or equal to 1.85 for light with a wavelength of 620 nm.

[0137] In some embodiments, the singlet energy (S1) of the material of the capping 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.

[0138] In other embodiments, the singlet energy (S1) contained in the capping layer 5 is less than or equal to 3.1 eV; preferably, less than or equal to 3.0 eV.

[0139] In some embodiments, the material of the capping layer 5 includes an organic compound having a small extinction coefficient for light greater than or equal to 430 nm, and the extinction coefficient of the organic compound at a wavelength of 430 nm is less than 0.1; preferably, the extinction coefficient of the organic compound at a wavelength of 430 nm is less than 0.003; more preferably, the extinction coefficient of the organic compound at a wavelength of 430 nm is less than 0.001. This allows the capping layer 5 to have high transmittance to visible light, thereby reducing the impact on the light extraction efficiency of the organic light-emitting device 10.

[0140] In some embodiments, the organic light-emitting device 10 further includes a substrate 1 located on the side of the first electrode 2 away from the organic functional layer 3.

[0141] In some embodiments, the anode may comprise a conductive metal, a metal oxide, or a conductive polymer. The anode can readily inject holes into the hole injection layer 31, the hole transport layer 32, or the light-emitting layer 33. In one embodiment, the absolute value of the difference between the work function of the anode and the HOMO level or valence band level of the light-emitting layer 33 is less than 0.5 eV, or the absolute value of the difference between the work function of the anode and the HOMO level or valence band level of the p-type semiconductor material serving as a HIL, HTL, or electron blocking layer is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. The anode material may include, but is not limited to, Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO, aluminum-doped zinc oxide (AZO), etc. Other suitable anode materials are known and 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 is patterned. For example, it can be a patterned ITO conductive substrate, and patterned ITO conductive substrates are commercially available and can be used to fabricate the organic light-emitting device 10 according to the embodiments of this application.

[0142] The cathode may comprise a conductive metal or metal oxide. Electrons can be readily injected into the electron injection layer 35, the electron transport layer 34, or directly into the light-emitting layer 33. In one embodiment, the absolute value of the difference between the work function of the cathode and the LUMO level or conduction band level of the light emitter in the light-emitting layer 33 is less than 0.5 eV; or, the absolute value of the difference between the work function of the cathode and the LUMO level or conduction band level of the n-type semiconductor material serving as the electron injection layer (35), electron transport layer (34), or hole blocking layer 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 cathodes in OLEDs can be used as the cathode material of the organic light-emitting device 10 in this embodiment. Examples of cathode materials include, but are not limited to: Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloy, BaF2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO, etc. The cathode 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.

[0143] It should be noted that the material of the capping layer 5 has a suitable energy level structure, thus enabling the capping layer 5 to strongly absorb light with wavelengths less than 400 nm, while its absorption of visible light with wavelengths greater than 400 nm is weak or close to zero. This prevents damage to the materials inside the organic light-emitting device 10 caused by high-energy light irradiation in subsequent processes. Simultaneously, the capping layer 5 has a high refractive index, which can beneficially guide the emission of visible light, improving the luminous efficiency of the organic light-emitting device 10. When the interface reflectivity between the capping layer 5 and adjacent electrodes is high, the influence of light interference is significant. Therefore, the refractive index of the material constituting the capping layer 5 is preferably greater than that of the adjacent electrodes. The refractive index of the capping layer 5 for light with a wavelength of 620 nm is generally 1.75 or higher, more preferably 1.8 or higher, and particularly preferably 1.85 or higher.

[0144] In some embodiments, the thickness of the cover 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.

[0145] The cover layer 5 of the organic light-emitting device 10 provided in this application embodiment contains the organic compound of the aforementioned embodiment. Since the organic compound has a high refractive index, when it is applied to the cover layer 5 in the organic light-emitting device 10, the refractive index of the cover layer 5 can be effectively improved, thereby improving the luminous efficiency of the organic light-emitting device 10.

[0146] This application also relates to the application of the organic light-emitting device 10 in various electronic devices, such as display devices, lighting devices, light sources, and sensors.

[0147] Please refer to Figure 2 This application also provides a display panel 100, which includes the organic light-emitting device 10 described in the foregoing embodiments.

[0148] In some embodiments, the display panel 100 further includes an array substrate 20 and an encapsulation layer 30, wherein the organic light-emitting device 10 is located on the array substrate 20 and electrically connected to the array substrate 20, and the encapsulation layer 30 covers the array substrate 20 and the organic light-emitting device 10.

[0149] It is understood that the array substrate 20 is used to drive the organic light-emitting device 10, and the encapsulation layer 30 is used to protect the organic light-emitting device 10.

[0150] In some embodiments, the display panel 100 further includes a cover plate 40 and an optical film 50, wherein the optical film 50 is located between the encapsulation layer 30 and the cover plate 40; wherein the optical film 50 includes at least one of a polarizer, a light conversion layer and a color filter.

[0151] The present application provides that the cover layer 5 of the organic light-emitting device 10 of the display panel 100 contains the organic compound described in the foregoing embodiments. Since the organic compound has a high refractive index and weak visible light absorption, when it is applied to the cover layer 5 in the organic light-emitting device 10, the refractive index of the cover layer 5 can be effectively increased and the light absorption in the visible light region can be reduced, thereby improving the luminous efficiency of the organic light-emitting device 10 and thus improving the performance of the display panel 100.

[0152] 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. Guided by 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. It can be noted that the compounds involved in the embodiments of this application, unless otherwise stated, are commercially available or can be prepared using existing preparation methods. Specific Implementation The following are examples illustrating the synthesis methods of organic compounds provided in the embodiments of this application, but this application is not limited to the following embodiments.

[0154] Example 1 This embodiment provides a method for preparing compound M1, wherein the synthetic route of compound M1 is shown below:

[0155] The synthesis procedure for compound M1 is shown below: Intermediate 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. The reaction mixture was heated to 140 °C and stirred for 2 h under a nitrogen atmosphere. After cooling, the reaction mixture was filtered to obtain the crude product. The crude product was then stirred overnight at 100 °C with toluene solvent, filtered, and dried to obtain compound M1. The yield of compound M1 was 84%, and the mass spectrometry results of the product were [m / z [H]]. + =677. Elemental analysis results: C, 88.64; H, 4.60; N, 2.03; O, 4.70.

[0156] Example 2 This embodiment provides a method for preparing compound M2, wherein the synthetic route of compound M2 is shown below:

[0157] The synthesis of compound M2 followed the same method as compound M1. The yield of compound M2 was 83%, and the mass spectrometry results of the product were [m / z [H]]. + =693. Elemental analysis of the product yielded the following values: C, 86.53; H, 4.52; N, 2.04; O, 2.30; S, 4.64.

[0158] It should be noted that the synthesis process of some compounds in the embodiments of this application is described by referring to the synthesis method of other compounds or intermediates. This means that the corresponding reactants can be replaced, while the molar amount of reactants and other conditions are the same.

[0159] Example 3 This embodiment provides a method for preparing compound M3, wherein the synthetic route of compound M3 is shown below:

[0160] Compound M3 was synthesized using the same method as compound M1 described above. The yield of compound M3 was 88%, and the mass spectrometry results of the product were [m / z [H]]. + =709. Elemental analysis of the product yielded the following values: C, 84.56; H, 4.43; N, 1.93; S, 9.07. The 1H NMR spectrum of compound M3 is attached. Figure 3 .

[0161] Example 4 This embodiment provides a method for preparing compound M4, wherein the synthetic route of compound M4 is shown below:

[0162] The synthesis procedure for compound M4 is shown below: Compound M4 was synthesized using the same method as compound M1 described above. The yield of compound M4 was 86%, and the mass spectrometry results of the product were [m / z [H]]. + =694. Elemental analysis of the product yielded the following values: C, 84.72; H, 4.37; N, 4.01; O, 2.32; S, 4.63. The 1H NMR spectrum of compound M4 is attached. Figure 4 .

[0163] Example 5 This embodiment provides a method for preparing compound M5, wherein the synthetic route of compound M5 is shown below:

[0164] The synthesis of intermediate 5-3 followed the same method as compound M1 described above. The yield of intermediate 5-3 was 87%, and the mass spectrometry results of the product were [m / z [H]]. + ]=501.

[0165] Compound M5 was synthesized using the same method as compound M1 described above. The yield of compound M5 was 85%, and the mass spectrometry results of the product were [m / z [H]]. + =667. Elemental analysis of the product yielded the following values: C, 86.30; H, 4.41; N, 2.12; O, 2.44; S, 4.75.

[0166] Example 6 This embodiment provides a method for preparing compound M6, wherein the synthetic route of compound M6 is shown below:

[0167] The synthesis of compound M6 followed the same method as compound M1 described above. The yield of compound M6 was 82%, and the mass spectrometry results of the product were [m / z [H]]. + =683. Elemental analysis of the product yielded the following values: C, 84.34; H, 4.25; N, 2.07; S, 9.36.

[0168] Example 7 This embodiment provides a method for preparing compound M7, wherein the synthetic route of compound M7 is shown below:

[0169] The synthesis of compound M7 followed the same method as compound M1 described above. The yield of compound M7 was 82%, and the mass spectrometry results of the product were [m / z [H]]. + =712. Elemental analysis of the product yielded the following values: C, 87.04; H, 4.37; N, 1.98; O, 2.25; S, 4.43.

[0170] Example 8 This embodiment provides a method for preparing compound M8, wherein the synthetic route of compound M8 is shown below:

[0171] The synthesis of compound M8 followed the same method as compound M1 described above. The yield of compound M8 was 85%, and the mass spectrometry results of the product were [m / z [H]]. +=767. Elemental analysis of the product yielded the following values: C, 87.57; H, 4.35; N, 1.83; O, 2.09; S, 4.15.

[0172] Example 9 This embodiment provides a method for preparing compound M9, wherein the synthetic route of compound M9 is shown below:

[0173] The synthesis of compound M9 followed the same method as compound M1 described above. The yield of compound M9 was 87%, and the mass spectrometry results of the product were [m / z [H]]. + =695. Elemental analysis of the product yielded the following values: C, 82.83; H, 4.23; N, 6.06; O, 2.32; S, 4.60.

[0174] Example 10 This embodiment provides a method for preparing compound M10, wherein the synthetic route of compound M10 is shown below:

[0175] Synthesis of intermediate 10⁻³: Intermediate 10⁻¹ (10 mmol), compound 10⁻² (10 mmol), Pd(PPh₃)₄ (0.1 mmol), and potassium carbonate (30 mmol) were dissolved in a mixed solvent of toluene, ethanol, and water. The mixture was stirred at 100 °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 10⁻³ in 89% yield. The mass spectrometry results of the product m / z [H + =362.

[0176] The synthesis of compound M10 followed the same method as that used for organic compound M1 described above. The yield of compound M10 was 87%, and the mass spectrometry results of the product were [m / z [H]]. + =727. Elemental analysis of the product yielded the following values: C, 89.13; H, 4.59; N, 1.93; O, 4.37.

[0177] Example 11 This embodiment provides a method for preparing compound M11, wherein the synthetic route of compound M11 is shown below:

[0178] The synthesis of compound M11 followed the same method as compound M1 described above. The yield of compound M11 was 85%, and the mass spectrometry results of the product were [m / z [H]]. + =769. Elemental analysis of the product yielded the following values: C, 87.36; H, 4.55; N, 1.83; O, 2.06; S, 4.21.

[0179] Example 12 This embodiment provides a method for preparing compound M12, wherein the synthetic route of compound M12 is shown below:

[0180] The synthesis of compound M12 followed the same method as that used for organic compound M1 described above. The yield of compound M12 was 81%, and the mass spectrometry results of the product were [m / z [H]]. + =743. Elemental analysis of the product yielded the following values: C, 87.22; H, 4.48; N, 1.86; O, 2.13; S, 4.35.

[0181] Example 13 This embodiment provides a method for preparing compound M13, wherein the synthetic route of compound M13 is shown below:

[0182] The synthesis of compound M13 followed the same method as compound M1 described above. The yield of compound M13 was 83%, and the mass spectrometry results of the product were [m / z [H]]. + =701. Elemental analysis of the product yielded the following values: C, 88.96; H, 4.47; N, 2.02; S, 4.59.

[0183] Example 14 This embodiment provides a method for preparing compound M14, wherein the synthetic route of compound M14 is shown below:

[0184] The synthesis of intermediate 14-3 followed the same method as intermediate 10-3 described above. The yield of intermediate 14-3 was 88%, and the mass spectrometry results of the product were [m / z]. + =388.

[0185] The synthesis of compound M14 followed the same method as that used for organic compound M1 described above. The yield of compound M14 was 83%, and the mass spectrometry results of the product were [m / z [H]]. + =753. Elemental analysis of the product yielded the following values: C, 89.25; H, 4.65; N, 1.84; O, 4.23.

[0186] Example 15 This embodiment provides a method for preparing compound M15, wherein the synthetic route of compound M15 is shown below:

[0187] The synthesis of intermediate 15-3 followed the same method as that used for organic compound M1 described above. The yield of intermediate 15-3 was 88%, and the mass spectrometry results of the product were [m / z]. + =475.

[0188] The synthesis of compound M15 followed the same method as that used for organic compound M1 described above. The yield of compound M15 was 85%, and the mass spectrometry results of the product were [m / z [H]]. + =657. Elemental analysis of the product yielded the following values: C, 83.93; H, 4.18; N, 2.12; S, 9.78.

[0189] Example 16 This embodiment provides a method for preparing compound M16, wherein the synthetic route of compound M16 is shown below:

[0190] The synthesis of intermediate 16-3 followed the same method as intermediate 10-3 described above. The yield of intermediate 16-3 was 83%, and the mass spectrometry results of the product were [m / z]. + =368.

[0191] The synthesis of compound M16 followed the same method as that used for organic compound M1 described above. The yield of compound M16 was 83%, and the mass spectrometry results of the product were [m / z [H]]. + =733. Elemental analysis of the product yielded the following values: C, 85.13; H, 4.23; N, 1.93; O, 4.32; S, 4.35.

[0192] Example 17 This embodiment provides a method for preparing compound M17, wherein the synthetic route of compound M17 is shown below:

[0193] The synthesis of intermediate 17-3 followed the same method as intermediate 10-3 described above. The yield of intermediate 17-3 was 84%, and the mass spectrometry results of the product were [m / z]. + =368.

[0194] The synthesis of compound M17 followed the same method as that used for organic compound M1 described above. The yield of compound M17 was 86%, and the mass spectrometry results of the product were [m / z [H]].+ =733. Elemental analysis of the product yielded the following values: C, 85.14; H, 4.24; N, 1.93; O, 4.38; S, 4.36.

[0195] Example 18 This embodiment provides a method for preparing compound M18, wherein the synthetic route of compound M18 is shown below:

[0196] The synthesis of intermediate 18-3 followed the same method as intermediate 10-3 described above. The yield of intermediate 18-3 was 85%, and the mass spectrometry results of the product were [m / z]. + =313.

[0197] The synthesis of compound M18 followed the same method as that used for organic compound M1 described above. The yield of compound M18 was 81%, and the mass spectrometry results of the product were [m / z [H]]. + =710. Elemental analysis of the product yielded the following values: C, 82.74; H, 4.27; N, 3.92; S, 9.05.

[0198] Example 19 This embodiment provides a method for preparing compound M19, wherein the synthetic route of compound M19 is shown below:

[0199] The synthesis of compound M19 followed the same method as that used for organic compound M1 described above. The yield of compound M19 was 81%, and the mass spectrometry results of the product were [m / z [H]]. + =679. Elemental analysis of the product yielded the following values: C, 84.82; H, 4.32; N, 6.19; O, 4.73.

[0200] Comparative Example Comparative Examples 1-5 of this application provide comparative compounds Ref-01, Ref-02, Ref-03, Ref-04, and Ref-05, with the following chemical structural formulas: .

[0201] Refractive index determination of organic compounds A 60 nm optical film of the test compound was deposited onto single-crystal silicon using vacuum evaporation. 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, and the refractive index (n) of the compound was obtained using the ellipsometer. The refractive index (n) values ​​of the compounds provided in Examples 1-19 and Comparative Examples 1-5 at different wavelengths are shown in Table 1. Table 1

[0202] Analysis of the data in Table 1 shows that the refractive indices of compounds M1 to M19 provided in the embodiments of this application are significantly higher than those of comparative compounds Ref-01 to Ref-05 in the same wavelength region. Furthermore, the absorption at 430 nm of compounds M1 to M19 provided in the embodiments of this application is significantly lower than that of comparative compounds Ref-01 to Ref-05, which is beneficial for reducing the absorption of light emitted by the light-emitting layer by the capping layer. Therefore, when compounds M1 to M19 provided in the embodiments of this application are applied to the capping layer of organic light-emitting devices, the increase in refractive index and the reduction in absorption synergistically promote the improvement of the light extraction efficiency of the organic light-emitting device.

[0203] Application of organic compounds in OLED devices according to this application Example 1 This application example provides the fabrication of OLED devices. The following specific device examples illustrate in detail the fabrication method and process of OLED devices using the organic compounds described in this application. Please refer to... Figure 1 In this embodiment, the structure of the OLED device is: ITO / PD:HT (3:97, 10nm) / HT (130nm) / BH:BD (3%, 40nm) / ET:Liq (5:5, 30nm) / Liq (1nm) / Al (100nm) / Capping layer 5 (60nm). In the following method for fabricating the OLED device, ITO conductive glass is used as the anode substrate, PD as the hole injection material, HT as the hole transport material, BH as the host material of the light-emitting layer 33, BD as the dopant material of the light-emitting layer 33, ET and Liq as electron transport materials, Liq as the electron injection material, and Al as the cathode material. Furthermore, compound M1 from the aforementioned synthesis example 1 is used as the material for capping layer 5 to prepare the corresponding OLED device. The chemical structural formulas of PD, HT, BH, BD, ET, and Liq are shown below: ; The fabricated OLED device is designated as "Device 01". The fabrication method of Device 01 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. Fabrication of the organic functional layer: First, the ITO substrate was 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 31 with a thickness of 10 nm. Then, at a deposition rate of 1.5 Å·s⁻¹, the hole implantation materials were deposited. -1 Hole transport material HT was deposited on hole injection layer 31 at a deposition rate of 1 Å / s to obtain hole transport layer 32 with a thickness of 130 nm. Next, BH and BD were deposited on hole transport layer 32 at a deposition rate of 1 Å / s, with a deposition rate ratio of 97:3, to obtain light-emitting layer 33 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⁻¹ to form an electron transport layer 34 with a thickness of 30 nm on the luminescent layer 33. Then, at 1 Å·s⁻¹, ET and Liq were co-deposited to form an electron transport layer 34 with a thickness of 30 nm on the luminescent layer 33. -1 Electron injection material Liq was deposited on electron transport layer 34 at a deposition rate of 1 Å·s⁻¹ to obtain electron injection layer 35 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 35 at a certain evaporation rate to obtain a second electrode 4 with a thickness of 100 nm. On the second electrode 4, a capping layer 5 with a thickness of 60 nm was formed by vacuum evaporation using an organic compound M1.

[0204] c. Packaging: The device is encapsulated in a nitrogen glove box using ultraviolet-cured resin to obtain device 01.

[0205] Examples 2 to 19 Referring to the preparation method of device 01, compounds M2 to M19 synthesized in the corresponding examples were selected as materials for the capping layer 5 of the OLED devices in Examples 2 to 19, respectively, to prepare devices 02 to 19. It can be understood that in the preparation methods of devices 01 to 19 above, except for the material of the capping layer 5, all other experimental conditions are the same.

[0206] Comparative Examples 1 to 5 Furthermore, referring to the preparation method of Application Example 1, comparative compounds Ref-01 to Ref-05 were used as materials for capping layer 5 to prepare comparative devices Ref-01 to Ref-05 respectively. Compared with the preparation method of device 01, the preparation methods of comparative devices Ref-01 to Ref-05 are the same except for the material of capping layer 5.

[0207] In the embodiments of this application, the current-voltage (current-voltage) of devices 01 to 19 and comparative devices Ref-01 to Ref-05 are... J-V The characteristics were characterized, and the luminous efficiency was recorded. Luminous efficiency is defined as the ratio of current density to 10 mA cm⁻¹. -2 The values ​​obtained at that time are shown in Table 2.

[0208] Table 2

[0209] As shown in Table 2, compared with comparative devices Ref-01 to Ref-05, the luminous efficiency of devices 01 to 19 in this application is significantly improved, proving that applying the organic compounds (M1 to M19) provided in this application to the capping layer of organic light-emitting devices can effectively improve the luminous efficiency of organic light-emitting devices. This is because the organic compounds provided in this application are aromatic amine compounds with pyrene and thiophene / furan fused-ring groups as their core structures. First, the introduction of pyrene, with its highly conjugated planar skeleton, effectively promotes intermolecular π-π stacking, improving the rigidity and close packing of the material structure, thereby achieving high polarizability and higher refractive index. Furthermore, the electron-rich pyrene and thiophene / furan fused-ring groups can also reduce the introduction of electron-withdrawing groups such as those containing thiazole / oxazole heterocycles to a certain extent, effectively regulating intramolecular charge transport effects and avoiding significant absorption in the visible light region, which would affect the light extraction efficiency. Therefore, when the aromatic amine compounds provided in this application are used as a capping layer in a light-emitting device, they can not only effectively improve the refractive index of the capping layer, but also reduce absorption in the visible light region, thereby improving the light extraction efficiency of the electronic device and realizing an electronic device with excellent performance, which has broad application prospects.

[0210] The organic compounds, compositions, optical films, organic light-emitting devices, and display panels provided in this application have been described in detail above. 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 organic compound, characterized in that, The organic compound has the structure represented by general formula (1): (1)； in, X is selected from O or S; Y is selected from at least one of CH and N; L1 is selected from at least one of single bond, phenyl, biphenyl, naphthyl, benzofuranyl, benzothiophenyl, and pyridyl; L2 is selected from at least one of single bond, phenyl, biphenyl, naphthyl, benzofuranyl, benzothiopheneyl, and pyridyl, wherein L2 is associated with a group They are either independent of each other or overlapped with each other; L3 is selected from at least one of a single bond, an aromatic group having 6 to 30 carbon atoms, and a heteroaromatic group having 5 to 30 carbon atoms; Ar1 is selected from at least one of hydrogen atoms, aromatic groups having 6 to 30 carbon atoms, and heteroaromatic groups having 5 to 30 carbon atoms.

2. The organic compound according to claim 1, characterized in that, The L3 is selected from at least one of single bond, phenyl, biphenyl, naphthyl, and pyridyl.

3. The organic compound according to claim 1, characterized in that, The Ar1 is selected from at least one of hydrogen atom, pyridyl, naphthyl, benzofuranyl, benzothiophene, benzooxazolyl, benzothiazolyl, oxazolopyridyl, thiazopyridyl, furan-pyridyl, thiophene-pyridyl, phenanthryl, anthracene, benzophenanthryl, o-phenanthrolinel, dibenzofuranyl, dibenzothiophene, quinolinyl, quinoxalinyl, naphthobenzofuranyl, naphthobenzothiophene, phenanthrylbenzofuranyl, and triphenylene.

4. The organic compound according to claim 1, characterized in that, The organic compound is selected from any of the following structures: 。 5. The organic compound according to any one of claims 1 to 4, characterized in that, The organic compound has a refractive index greater than 1.75 for light with a wavelength of 620 nm.

6. The organic compound according to any one of claims 1 to 4, characterized in that, The extinction coefficient of the organic compound for light with a wavelength greater than or equal to 430 nm is less than 0.1, and the extinction coefficient of the organic compound for light with a wavelength less than or equal to 400 nm is greater than or equal to 0.

3.

7. A composition, characterized in that, The composition comprises at least one organic solvent and at least one organic compound as described in any one of claims 1 to 6.

8. An optical film, characterized in that, The material of the optical film includes at least one organic compound as described in any one of claims 1 to 6, or is prepared from the composition as described in claim 7.

9. An organic light-emitting device, characterized in that, include: First electrode; An organic functional layer is disposed on one side of the first electrode; The second electrode is disposed on the side of the organic functional layer away from the first electrode; A capping layer is disposed on the side of the second electrode away from the organic functional layer, the material of the capping layer comprising at least one organic compound as described in any one of claims 1 to 6, or the capping layer is prepared from the composition as described in claim 7, or the capping layer comprises the optical film as described in claim 8.

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

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