Organic compound, composition, electronic device, and display panel

Abstract

The invention discloses an organic compound, a composition, an electronic device and a display panel. The organic compound has a structure as shown in formula (1): (1); the organic compound provided by the invention is an arylamine compound taking dibenzofuran or dibenzothiophene substituted by a heterocyclic group containing a nitrogen atom, an oxygen atom or a sulfur atom as a core structure, and can have a relatively high refractive index; when the organic compound provided by the invention is used in a covering layer of an electronic device, the refractive index of the covering layer can be effectively improved, so that the luminous efficiency of the electronic device is improved, and the electronic device with excellent performance can be realized.

Description

Technical Field

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

[0002] Organic Light Emitting Display (OLED) displays are an advanced self-luminous display technology. They generate excitons through the transfer and recombination of charge carriers between different functional layers. These excitons emit light through high-quantum-efficiency organic compounds or metal complexes. OLED technology is known for its advantages such as self-luminescence, high brightness, high efficiency, high contrast, and fast response time.

[0003] In recent years, the luminous efficiency of OLED diodes has increased significantly, and their internal quantum efficiency has approached the theoretical limit. Therefore, improving the light extraction efficiency has become the key to further improving device stability and current efficiency. For example, by optimizing the stacking of metal complexes in the emission layer and the matching of the refractive index between the functional layers, the light extraction efficiency can be effectively improved. In 2001, researchers such as Hung covered the surface of the metal cathode with an organic or inorganic compound layer about 50 nanometers thick, and enhanced the device performance by precisely controlling the thickness and refractive index. In 2003, Riel et al. attempted to evaporate the 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] Given these challenges, researchers have begun exploring organic compounds with high refractive indices to improve light extraction efficiency in electroluminescent devices. Ideal compounds should meet the following requirements: a high extinction coefficient in the ultraviolet (less than 400 nanometers) to protect device materials from harmful light; a near-zero extinction coefficient in the visible (greater than 430 nanometers) to ensure high transmittance and minimize the impact on light extraction efficiency; a high refractive index with minimal variation in the visible range to improve light extraction efficiency and optimize device structure; and a high glass transition temperature to enhance thermal stability.

[0005] Therefore, developing a new generation of materials that can improve the light extraction efficiency of OLED devices, namely covering layer materials, has become a research focus. Summary of the Invention

[0006] The present application provides an organic compound, a composition, an electronic device and a display panel, which can obtain an organic compound with a high refractive index, so that the covering layer in the electronic device has a high refractive index, thereby improving the luminous efficiency of the electronic device.

[0007] The present application provides an organic compound having a structure as shown in formula (1): (1); wherein X, Y and Z are the same or different and are independently selected from oxygen atoms or sulfur atoms; W and V are the same or different and are independently selected from CH or a nitrogen atom; L1 and L2 are the same or different and are independently selected from at least one of a single bond, a substituted or unsubstituted aromatic group having 6 to 25 carbon atoms, and a substituted or unsubstituted heteroaromatic group having 5 to 25 carbon atoms; Ar is selected from at least one of a hydrogen atom, a substituted or unsubstituted aromatic group having 6 to 25 carbon atoms, and a substituted or unsubstituted heteroaromatic group having 5 to 25 carbon atoms; The substituents in the substituted or unsubstituted L1, L2 and Ar are at least one selected from an aromatic group having 6 to 25 carbon atoms and a heteroaromatic group having 5 to 25 carbon atoms; The heteroatom of the heteroaryl group in L1, L2 and Ar is at least one selected from a nitrogen atom, an oxygen atom and a sulfur atom.

[0008] In accordance with the above-mentioned purpose of the present application, an embodiment of the present application further provides a composition comprising at least one organic solvent and at least one organic compound as described above.

[0009] In accordance with the above-mentioned purpose of the present application, an embodiment of the present application further provides an electronic device, comprising: a first electrode; an organic functional layer, disposed on one side of the first electrode; a second electrode, disposed on a side of the organic functional layer away from the first electrode; The covering layer is arranged on a side of the second electrode away from the organic functional layer. The material of the covering layer includes at least one organic compound as described above, or the covering layer is made of the composition as described above.

[0010] According to the above-mentioned purpose of the present application, an embodiment of the present application further provides a display panel, which includes the electronic device as described above.

[0011] The present application provides an organic compound, a composition, an electronic device, and a display panel. The organic compound is an aromatic amine compound having a core structure of dibenzofuran or dibenzothiophene substituted by a heterocyclic group containing nitrogen atoms, oxygen atoms, or sulfur atoms, and can have a relatively high refractive index. When the organic compound provided by the present application is used in a covering layer of an electronic device, the refractive index of the covering layer can be effectively increased, thereby increasing the light extraction efficiency of the electronic device, and realizing an electronic device with excellent performance. BRIEF DESCRIPTION OF THE DRAWINGS

[0012] In order to more clearly illustrate the technical solutions in the embodiments of the present application, the following briefly introduces the drawings required for use in the description of the embodiments. Obviously, the drawings described below are only some embodiments of the present application. For those skilled in the art, other drawings can be obtained based on these drawings without creative work.

[0013] Figure 1 A schematic diagram of the structure of an electronic device provided in an embodiment of the present application; Figure 2 This is a hydrogen spectrum data diagram of the organic compound M3 provided in the examples of this application. DETAILED DESCRIPTION

[0014] The technical solutions of the present application will be further described in detail below with reference to specific embodiments. The present application can be implemented in many different forms and is not limited to the embodiments described herein. On the contrary, the purpose of providing these embodiments is to provide a more thorough and comprehensive understanding of the disclosure of the present application.

[0015] Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art.

[0016] As used herein, the term "and / or" includes any and all combinations of one or more of the associated listed items.

[0017] In the present application, "substituted" means that a hydrogen atom in a substituted group is replaced by a substituent.

[0018] In this application, hydrogen atoms include isotopes having different numbers of neutrons, namely protium, deuterium and tritium.

[0019] In this application, "substituted or unsubstituted" means that the defined group may be substituted or unsubstituted. When the defined group is substituted, it should be understood that it is optionally substituted by groups acceptable in the art, including but not limited to: deuterium atoms, cyano groups, isocyano groups, nitro groups, halogen atoms, C 1-10 Alkyl, C 1-10 Alkoxy, C 1-10 Alkylthio, C 6-30Aryl, C 6-30 Aryloxy, C 6-30 Arylthio, C 3-30 Heteroaryl, C 1-30 Silane group, C 2-10 Alkylamino, C 6-30 arylamine group, or a combination of the above groups, etc.

[0020] "Aryl or aromatic group" refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removing a hydrogen atom. It can be a monocyclic aromatic group, a condensed aromatic group, or a polycyclic aromatic group. For polycyclic rings, at least one is an aromatic ring system. For example, "substituted or unsubstituted C6~25 aromatic group" refers to an aromatic group containing 6 to 25 carbon atoms, and the aromatic group is optionally further substituted; suitable examples include, but are not limited to: benzene, biphenyl, terphenyl, naphthalene, anthracene, fluoranthene, phenanthrene, triphenylene, perylene, tetracene, pyrene, benzopyrene, acenaphthene, fluorene and its derivatives. It is understood that multiple aromatic groups can also be interrupted by short non-aromatic units (e.g., <10% non-H atoms, such as C, N or O atoms), such as acenaphthene, fluorene, or 9,9-diarylfluorene, triarylamine, diaryl ether system should also be included in the definition of aromatic group.

[0021] As used herein, the “substituted or unsubstituted C5-25 heteroaromatic group” refers to a monovalent group comprising a carbocyclic heteroaromatic system having at least one heteroatom selected from a nitrogen atom, an oxygen atom, a phosphorus atom, a sulfur atom or a silicon atom as a ring atom and 5 to 25 carbon atoms. Non-limiting examples of heteroaromatic groups containing 5 to 25 carbon atoms can include furanyl, thienyl, 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, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl, 1,3 ,5-triazinyl, benzofuranyl, benzisofuranyl, benzothiophenyl, benzisothiophenyl, indolyl, isoindolyl, indazolyl, benzimidazolyl, benzoxazolyl, benzisoxazolyl, benzothiazolyl, 2,1,3-benzoxadiazole, quinolyl, isoquinolyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, benzotriazinyl, benzoxazinyl, purinyl, pteridinyl, indolizinyl, benzothiazinyl, acridinyl, phenanthrazinyl, phenathiazinyl, phenoxazinyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, naphthofuranyl, quinolyl, isoquinolyl, indole[1,2-f]phenanthridinyl, imidazo[2,1-a]isoquinolyl, 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, etc., also include aromatic combination groups with heteroatoms, but are not limited thereto.

[0022] In this application, "*" connected to a single bond indicates a connection or fusion site.

[0023] In this application, when the linking site is not specified in the group, it means that any linking site in the group can be used as the linking site; In the present application, the single bond to which the substituent is connected runs through the corresponding ring, indicating that the substituent can be connected to any position of the ring, for example R is connected to any substitutable position of the benzene ring.

[0024] The present invention provides an organic compound having a structure as shown in formula (1): (1); wherein X, Y and Z are the same or different and are independently selected from oxygen atoms or sulfur atoms; W and V are the same or different and are independently selected from CH or a nitrogen atom; L1 and L2 are the same or different and are independently selected from at least one of a single bond, a substituted or unsubstituted aromatic group having 6 to 25 carbon atoms, and a substituted or unsubstituted heteroaromatic group having 5 to 25 carbon atoms; Ar is selected from at least one of a hydrogen atom, a substituted or unsubstituted aromatic group having 6 to 25 carbon atoms, and a substituted or unsubstituted heteroaromatic group having 5 to 25 carbon atoms; The substituents in the substituted or unsubstituted L1, L2 and Ar are at least one selected from an aromatic group having 6 to 25 carbon atoms and a heteroaromatic group having 5 to 25 carbon atoms; The heteroatom of the heteroaryl group in L1, L2 and Ar is at least one selected from a nitrogen atom, an oxygen atom and a sulfur atom.

[0025] It can be understood that the expression of a ring structure crossed out by “—” indicates that the connection site is any position on the ring structure that can form a bond.

[0026] During the implementation and application process, the organic compound provided in the embodiment of the present application is an aromatic amine compound with a core structure of dibenzofuran or dibenzothiophene substituted by a heterocyclic group containing nitrogen atoms, oxygen atoms or sulfur atoms, and can have a higher refractive index; when the organic compound provided in the present application is used in the covering layer of an electronic device, the refractive index of the covering layer can be effectively improved, thereby improving the light extraction efficiency of the electronic device, and an electronic device with excellent performance can be realized.

[0027] Specifically, in some embodiments, the substituted or unsubstituted substituents in L1, L2 and Ar are selected from at least one of phenyl, pyridyl, benzoxazolyl, benzothiazolyl, quinolyl, isoquinolyl and quinoxalinyl.

[0028] In some embodiments, L1 and L2 are both divalent groups.

[0029] In some embodiments, L1 and L2 are the same or different and are independently selected from at least one of a single bond, a phenyl group, a naphthyl group, a biphenyl group, a pyridyl group, a pyrazinyl group, a carbazolyl group, a phenanthrenyl group, a triphenylene group, an o-phenanthroline group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzoxazolyl group, a benzothiazolyl group, a naphthofuranyl group, a naphthothiophenyl group, a benzo[k]xanthenyl group, a benzo[4,5-bcd]furanyl group, a benzo[k]thioanthenyl group, and a benzo[4,5-bcd]thiophenyl group.

[0030] In some embodiments, L1 and L2 are the same or different and are independently selected from a single bond, a phenyl group, a dibenzofuranyl group, or a benzoxazolyl group.

[0031] In some embodiments, L1 is selected from phenyl.

[0032] In some embodiments, L2 is selected from a single bond, phenyl, dibenzofuranyl, or benzoxazolyl.

[0033] In some embodiments, Ar is selected from at least one of a hydrogen atom, a phenyl group, a benzoxazolyl group, a benzothiazolyl group, a phenanthryl group, a pyrene group, a triphenylene group, a phenanthroline group, a dibenzofuranyl group, a dibenzothiophenyl group, an N-phenylcarbazolyl group, a quinolyl group, an isoquinolyl group, a quinoxalinyl group, a naphthobenzofuranyl group, a naphthobenzothiophenyl group, a phenanthrobenzofuranyl group, and a triphenylene group.

[0034] In some embodiments, Ar is selected from benzoxazolyl, benzothiazolyl, triphenylene, phenyl, naphthobenzofuranyl, phenanthrobenzofuranyl, or phenanthrenyl.

[0035] In some embodiments, all W are selected from CH, or at least one W is selected from a nitrogen atom; further, all W are selected from CH, or one W is selected from a nitrogen atom.

[0036] In some embodiments, all V are selected from CH, or at least one W is selected from a nitrogen atom; further, all V are selected from CH, or one V is selected from a nitrogen atom.

[0037] In some embodiments, the organic compound is selected from any one of the following compounds:

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[0158] The organic compounds provided in the embodiments of the present application have a higher glass transition temperature and thus have higher stability; in some embodiments, the glass transition temperature T g Greater than or equal to 100°C. In a preferred embodiment, T g Greater than or equal to 120°C. In a preferred embodiment, T g Greater than or equal to 140°C. In a more preferred embodiment, T g Greater than or equal to 160°C. In a most preferred embodiment, T g Greater than or equal to 180°C.

[0159] In some embodiments, the refractive index of the organic compound for light with a wavelength of 620 nm is greater than 1.75; preferably, the refractive index of the organic compound for light with a wavelength of 620 nm is greater than 1.8; more preferably, the refractive index of the organic compound for light with a wavelength of 620 nm is greater than 1.85.

[0160] 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.

[0161] The organic compounds provided in the embodiments of this application have a low extinction coefficient. 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. Furthermore, the organic compounds provided in the embodiments of this application have a high transmittance for visible light, reducing the impact on the light extraction efficiency of the device.

[0162] In some embodiments, the organic compound provided in the embodiments of the present application has a large extinction coefficient for light within a wavelength range less than or equal to 400 nm; preferably, 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.

[0163] In some embodiments, the organic compound can be formed into a film layer in an OLED device using an evaporation process.

[0164] In some embodiments, 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, further preferably the molecular weight of the organic compound is less than or equal to 1000 g / mol, more preferably the molecular weight of the organic compound is less than or equal to 950 g / mol, and most preferably the molecular weight of the organic compound is less than or equal to 900 g / mol.

[0165] In some embodiments, the organic compound can be formed into a film layer in an OLED device using a printing process.

[0166] In some embodiments, 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, very preferably the molecular weight of the organic compound is greater than or equal to 1000 g / mol, 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.

[0167] 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.

[0168] In addition, the present application also provides a composition comprising at least one organic solvent and at least one organic compound as described in the above embodiments.

[0169] In some embodiments, the organic solvent is selected from a mixture of one or more of aromatic, heteroaromatic, ester, aromatic ketone, aromatic ether, aliphatic ketone, aliphatic ether, alicyclic, olefinic compounds, boric acid esters, and phosphate esters.

[0170] In some embodiments, in the composition provided by the embodiments of the present application, the organic solvent is selected from aromatic or heteroaromatic solvents, for example, aromatic solvents substituted with aliphatic chains and / or aliphatic rings, or aromatic ketone solvents, or aromatic ether solvents.

[0171] In some embodiments, the organic solvent may include aromatic or heteroaromatic solvents: p-diisopropylbenzene, pentylbenzene, tetralin, 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-tetralone, 2-tetralone, 2-(phenylepoxy)tetralone, 6-(methoxy)tetralone, acetophenone, propiophenone, benzophenone, and their derivatives, such as 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylpropiophenone, 3-methylpropiophenone, 2-methylpropiophenone, isophorone, 2,6,8-trimethyl-4-nonanone, fenchone, 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2,5-hexanedione, phorone, di-n-amyl ketone; Aromatic ether solvents: 3-phenoxytoluene, butoxybenzene, benzylbutylbenzene, p-anisaldehyde dimethyl acetal, tetrahydro-2-phenoxy-2H-pyran, 1,2-dimethoxy-4-(1-propenyl)benzene, 1,4-benzodioxane, 1,3-dipropylbenzene, 2,5-dimethoxytoluene, 4-ethyl acetate, 1,2,4-trimethoxybenzene, 4-(1-propenyl)-1,2-dimethoxybenzene, 1,3-dimethoxybenzene, glycidylphenyl Ether, dibenzyl ether, 4-tert-butylanisole, trans-p-propenylanisole, 1,2-dimethoxybenzene, 1-methoxynaphthalene, diphenyl ether, 2-phenoxymethyl ether, 2-phenoxytetrahydrofuran, ethyl-2-naphthyl ether, amyl ether, c-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.

[0172] In some embodiments, when the composition provided in the embodiments of the present application is an ink, the organic solvent in the composition can be selected from: aliphatic ketones; for example, the organic solvent can be selected from 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2,5-hexanedione, 2,6,8-trimethyl-4-nonanone, phorone, di-n-amyl ketone, etc.; or aliphatic ethers, for example, amyl ether, hexyl ether, dioctyl ether, ethylene glycol dibutyl ether, diethylene glycol diethyl ether, diethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, triethylene glycol ethyl methyl ether, triethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, etc.

[0173] In some embodiments, when the composition provided in the embodiments of the present application is a printing ink, the composition may further include another organic solvent. The other organic solvent may include: methanol, ethanol, 2-methoxyethanol, dichloromethane, chloroform, chlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1,4-dioxane, acetone, methyl ethyl ketone, 1,2-dichloroethane, 3-phenoxytoluene, 1,1,1-trichloroethane, 1,1,2,2-tetrachloroethane, ethyl acetate, butyl acetate, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, tetralin, decalin, indene and / or mixtures thereof.

[0174] In some embodiments, the composition provided in the embodiments of the present application may be a solution.

[0175] In other embodiments, the composition provided in the embodiments of the present application may be a suspension.

[0176] In the composition provided in the embodiments of the present application, the mass content of the organic compound in the composition is greater than or equal to 0.01% and less than or equal to 20%. 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%.

[0177] In some embodiments, the content of the organic compound in the composition ranges from 0.1 to 15 wt %, more preferably, the content of the organic compound in the composition ranges from 0.2 to 10 wt %, and most preferably, the content of the organic compound in the composition ranges from 0.25 to 5 wt %.

[0178] In some embodiments, the composition provided in the embodiments of the present application can also be used as a coating or printing ink, and can be used to prepare organic electronic devices, and the preparation method by printing or coating is particularly preferred.

[0179] Suitable printing or coating techniques include (but are not limited to) inkjet printing, nozzle printing, letterpress printing, screen printing, dip coating, spin coating, doctor blade coating, roller printing, twist roll printing, lithographic printing, flexographic printing, rotary printing, spray coating, brush or pad printing, and slot die coating. Gravure printing, nozzle printing, and inkjet printing are preferred. The solution or suspension may further include one or more components, such as surfactants, lubricants, wetting agents, dispersants, hydrophobic agents, and adhesives, to adjust viscosity, film-forming properties, and enhance adhesion. For detailed information on printing techniques and their requirements for related 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.

[0180] Please refer to Figure 1 The embodiment of the present application further provides an electronic device 12 , which includes a first electrode 21 , a second electrode 22 , an organic functional layer 23 and a covering layer 30 .

[0181] The organic functional layer 23 is disposed on one side of the first electrode 21 , and the second electrode 22 is located on a side of the organic functional layer 23 away from the first electrode 21 . The cover layer 30 is disposed on a side of the second electrode 22 away from the organic functional layer 23 .

[0182] In an embodiment of the present application, the material of the covering layer 30 includes at least one of the organic compounds described in the above embodiments, or the covering layer 30 is made of the composition described in the above embodiments; it can be understood that the organic compound provided in the embodiment of the present application is an aromatic amine compound with a core structure of dibenzofuran or dibenzothiophene substituted by a heterocyclic group containing nitrogen atoms, oxygen atoms or sulfur atoms, and can have a higher refractive index; when the organic compound provided by the present application is used in the covering layer of an electronic device, the refractive index of the covering layer can be effectively improved, thereby improving the light extraction efficiency of the electronic device, and realizing an electronic device with excellent performance.

[0183] In some embodiments, the electronic device 12 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 spin electronic device, an organic sensor, and an organic plasmon emitting diode, etc., with an organic light emitting diode being particularly preferred.

[0184] In some embodiments, the first electrode 21 can be one of the anode and the cathode, and the second electrode 22 can be the other of the anode and the cathode; therefore, the covering layer 30 can be located on the side of the anode away from the organic functional layer 23, or the covering layer 30 can be located on the side of the anode away from the organic functional layer 23.

[0185] It is understandable that in the embodiment of the present application, the first electrode 21 can be used as an anode and the second electrode 22 can be used as a cathode for illustration; correspondingly, the covering layer 30 is located on the side of the second electrode 22 away from the organic functional layer 23.

[0186] In some embodiments, the organic functional layer 23 includes at least one light-emitting layer 233 and a light-emitting auxiliary layer stacked with the light-emitting layer 233; wherein, taking the number of the light-emitting layer 233 as one layer as an example, the light-emitting auxiliary layer may include at least one of a hole injection layer 231, a hole transport layer 232, an electron transport layer 234 and an electron injection layer 235; specifically, the hole injection layer 231 is arranged between the first electrode 21 and the second electrode 22, the hole transport layer 232 is arranged between the hole injection layer 231 and the second electrode 22, the light-emitting layer 233 is arranged between the hole transport layer 232 and the second electrode 22, the electron transport layer 234 is arranged between the light-emitting layer 233 and the second electrode 22, and the electron injection layer 235 is arranged between the electron transport layer 234 and the second electrode 22.

[0187] In some embodiments, the organic compound provided in the embodiments of the present application can be used as the material of the covering layer 30 of the electronic device 12. Furthermore, in other embodiments of the present application, the organic compound can also be used as the material of the electron transport layer 233 of the electronic device 12 or the main material in the light-emitting layer 233.

[0188] In some embodiments, since the cover layer 30 contains the organic compound, the organic compound has a higher glass transition temperature to improve the thermal stability of the organic compound. In some preferred embodiments, the glass transition temperature T g Greater than or equal to 100°C. In a preferred embodiment, the glass transition temperature T g Greater than or equal to 120°C. In a preferred embodiment, the glass transition temperature T g Greater than or equal to 140°C. In a more preferred embodiment, the glass transition temperature T g Greater than or equal to 160 ° C. In a most preferred embodiment, the glass transition temperature T g Greater than or equal to 180°C.

[0189] In some embodiments, the material of the covering layer 30 includes the organic compound having a higher refractive index. Therefore, the refractive index of the covering layer 30 is also higher, which can help improve the light efficiency of the electronic device 12, especially help improve the external luminous efficiency; wherein, the refractive index of the covering layer 30 for light with a wavelength of 620nm is greater than or equal to 1.75; preferably, the refractive index of the covering layer 30 for light with a wavelength of 620nm is greater than or equal to 1.8; more preferably, the refractive index of the covering layer 30 for light with a wavelength of 620nm is greater than or equal to 1.85.

[0190] In some embodiments, the singlet energy (S1) of the material of the cover layer 30 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.

[0191] In other embodiments, the singlet state energy (S1) of the capping layer 30 is less than or equal to 3.1 eV; preferably, less than or equal to 3.0 eV.

[0192] In some embodiments, the material of the cover layer 30 includes the organic compound having a relatively low extinction coefficient, 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 cover layer 30 to have a relatively high transmittance for visible light, thereby reducing the impact on the light extraction efficiency of the electronic device 12.

[0193] In some embodiments, the electronic device 12 can be selected from an organic light emitting diode (OLED), an organic light-emitting cell (OLEEC), an organic field-effect transistor (OFET), or an organic light-emitting field-effect transistor.

[0194] The electronic device 12 may be disposed on a substrate 11 , and the first electrode 21 (anode), the second electrode 22 (cathode), and the cover layer 30 in the device structure of the electronic device 12 are described below, but are not limited thereto.

[0195] In some embodiments, the first electrode 21 may comprise a conductive metal, metal oxide, or conductive polymer. The first electrode 21 can easily inject holes into the hole injection layer 231 (HIL), hole transport layer 232 (HTL), or light-emitting layer 233. In one embodiment, the absolute difference between the work function of the first electrode 21 and the HOMO energy level or valence band energy level of the emitter in the light-emitting layer 233 is less than 0.5 eV. Alternatively, the absolute difference between the work function of the first electrode 21 and the HOMO energy level or valence band energy level of the p-type semiconductor material serving as the 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. The material of the first electrode 21 may include, but is not limited to, Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO, aluminum-doped zinc oxide (AZO), and the like. Other suitable materials for the first electrode 21 are known and can be readily selected by one of ordinary skill in the art. The material for the first electrode 21 can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, and electron beam (e-beam). In some embodiments, the first electrode 21 is patterned. For example, it can be a patterned ITO conductive substrate, which is commercially available and can be used to prepare the electronic device 12 according to the embodiments of the present application.

[0196] The second electrode 22 may comprise a conductive metal or metal oxide. The second electrode 22 can easily inject electrons into the electron injection layer 235 (EIL), the electron transport layer 234 (ETL), or directly into the light-emitting layer 233. In one embodiment, the absolute difference between the work function of the second electrode 22 and the LUMO energy level or conduction band energy level of the emitter in the light-emitting layer 233 is less than 0.5 eV. Alternatively, the absolute difference between the work function of the second electrode 22 and the LUMO energy level or conduction band energy level of the n-type semiconductor material serving as the electron injection layer 234 (EIL), electron transport layer 234 (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, any material that can be used as a cathode in an OLED can be used as the material for the second electrode 22 of the electronic device 12 in the embodiments of the present application. Examples of materials for the second electrode 22 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 material for the second electrode 22 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.

[0197] It should be noted that the material of the cover layer 30 has a suitable energy level structure, so that the cover layer 30 can strongly absorb light with a wavelength less than 400nm, while weakly absorbing or approaching zero absorption of visible light with a wavelength greater than 400nm, thereby preventing the material inside the electronic device 12 from being damaged by high-energy light in subsequent processes. At the same time, the cover layer 30 has a high refractive index, which can beneficially guide the emission of visible light and improve the luminous efficiency of the electronic device 12. When the interface reflectivity between the cover layer 30 and the adjacent electrode is large, the influence of light interference is large. Therefore, the refractive index of the material constituting the cover layer 30 is preferably greater than the refractive index of the adjacent electrode. The refractive index of the cover layer 30 for light with a wavelength of 620nm is generally greater than 1.75, more preferably, the refractive index of the cover layer 30 for light with a wavelength of 620nm is greater than 1.8, and particularly preferably, the refractive index of the cover layer 30 for light with a wavelength of 620nm is greater than 1.85.

[0198] In some embodiments, the thickness of the covering layer 30 is 10nm to 200nm, the thickness of the covering layer 30 is preferably 20nm to 150nm, the thickness of the covering layer 30 is more preferably 30nm to 100nm, and the thickness of the covering layer 30 is most preferably 40nm to 90nm.

[0199] The electronic device 12 can be used in various electronic devices, such as display devices, lighting devices, light sources, sensors, and the like.

[0200] The organic compounds provided in the embodiments of the present application will be described below in conjunction with preferred embodiments. However, the embodiments of the present application are not limited to the following embodiments. It should be understood that the attached claims summarize the scope of the present application. Under the guidance of the concept of the present application, those skilled in the art should realize that certain changes made to the various embodiments of the present application will be covered by the spirit and scope of the claims of the present application. Specific embodiments The following examples illustrate the synthesis methods of the organic compounds provided in the examples of the present application, but the present application is not limited to the following examples.

[0202] Synthesis of organic compound M1:

[0203] Synthesis of intermediate 1-2 Compound 1-1 (10 mmol), pinacol diboronate (10 mmol), Pd(dppf)3Cl2 (0.1 mmol), and potassium acetate (30 mmol) were dissolved in 1,4-dioxane and stirred at 100°C for 6 h under a nitrogen atmosphere. The reaction mixture was cooled to room temperature and partially evaporated using a rotary evaporator. The mixture was then extracted three times with dichloromethane and water. After separation, the organic phase was dried to obtain a crude product. The crude product was purified by column chromatography to obtain intermediate 1-2 in an 86% yield. The mass spectrum of the product was m / z [H + ]=328.

[0204] Synthesis of intermediates 1-4 Intermediate 1-2 (10 mmol), compound 1-3 (10 mmol), Pd(PPh3)4 (0.1 mmol), and potassium carbonate (30 mmol) were dissolved in a mixture of toluene, ethanol, and water and stirred at 100°C for 12 hours under a nitrogen atmosphere. The reaction mixture was cooled to room temperature, and the solvent was partially removed using a rotary evaporator. The mixture was then extracted three times with dichloromethane and water. After separation, the organic phase was dried to obtain a crude product. The crude product was purified by column chromatography to obtain intermediate 1-4 in a 35% yield. The mass spectrum of the product was m / z [H + ]=319.

[0205] Synthesis of organic compound M1: Intermediate 1-4 (10 mmol), compound 1-5 (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 3 h under a nitrogen atmosphere. After the reaction system cooled, the xylene solvent was partially removed by rotary evaporation, and the mixture was extracted and separated with dichloromethane and water. The resulting organic phase was dried on a rotary evaporator to obtain a crude product. The crude product was stirred with toluene solvent at 100°C overnight, filtered, and dried to obtain organic compound M1 with a yield of 82%. The mass spectrum of the product was m / z [H + ]=686. Elemental analysis: Calculated values: C, 78.71; H, 3.82; N, 8.16; O, 9.32; Found values: C, 78.75; H, 3.87; N, 8.13; O, 9.37.

[0206] Synthesis of organic compound M2:

[0207] The synthesis of organic compound M2 was carried out according to the synthesis method of organic compound M1, with a yield of 85%. The mass spectrum of the product was m / z [H + ]=718. Elemental analysis of the product: calculated values: C, 75.19; H, 3.65; N, 7.79; O,4.45; S, 8.92; found values: C, 75.25; H, 3.67; N, 7.73; O, 4.45; S, 8.96.

[0208] It should be noted that the synthesis process of some organic compounds in the embodiments of the present application is described with reference to the synthesis method of other organic compounds or intermediates, which means that the corresponding reactants can be replaced, and the molar amount of the reactants and other conditions are the same.

[0209] Synthesis of organic compound M3:

[0210] The synthesis of intermediate 3-2 was carried out according to the above-mentioned synthesis method of intermediate 3-2, with a yield of 65% and a mass spectrum of m / z [H + ]=335.

[0211] The synthesis of organic compound M3 was carried out according to the synthesis method of organic compound M1, with a yield of 85%. The mass spectrum of the product was m / z [H +]=702. Elemental analysis of the product revealed calculated values: C, 76.91; H, 3.73; N, 7.97; O, 6.83; S, 4.56; measured values: C, 76.96; H, 3.75; N, 7.91; O, 6.86; S, 4.58. The hydrogen spectrum data of organic compound M3 are attached. Figure 2 .

[0212] Synthesis of organic compound M4:

[0213] The synthesis of organic compound M4 was carried out according to the synthesis method of organic compound M1, with a yield of 87%. The mass spectrum of the product was m / z [H + ]=734. Elemental analysis of the product: calculated values: C, 73.55; H, 3.57; N, 7.62; O,2.18; S, 13.09; found values: C, 73.51; H, 3.52; N, 7.69; O, 2.28; S, 13.19.

[0214] Synthesis of organic compound M5:

[0215] The synthesis of intermediate 5-2 was carried out according to the synthesis method of intermediate 1-2, with a yield of 84%. The mass spectrum of the product was m / z [H + ]=344.

[0216] The synthesis of intermediate 5-4 was carried out according to the synthesis method of intermediate 1-4, with a yield of 32%. The mass spectrum of the product was m / z [H + ]=335.

[0217] The synthesis of organic compound M5 was carried out according to the synthesis method of organic compound M1, with a yield of 87%. The mass spectrum of the product was m / z [H + ] = 702. Elemental analysis of the product: calculated values: C, 76.91; H, 3.73; N, 7.97; O, 6.83; S, 4.56; found values: C, 76.95; H, 3.71; N, 7.94; O, 6.87; S, 4.59.

[0218] Synthesis of organic compound M6:

[0219] The synthesis of organic compound M6 was carried out according to the synthesis method of organic compound M1, with a yield of 82%. The mass spectrum of the product was m / z [H +]=734. Elemental analysis of the product: calculated values: C, 73.55; H, 3.57; N, 7.62; O,2.18; S, 13.09; found values: C, 73.52; H, 3.58; N, 7.68; O, 2.23; S, 13.13.

[0220] Synthesis of organic compound M7:

[0221] The synthesis of intermediate 7-3 was carried out according to the synthesis method of intermediate 1-4, with a yield of 39% and a mass spectrum of m / z [H+] = 351.

[0222] The synthesis of organic compound M7 was carried out according to the synthesis method of organic compound M1, with a yield of 84%. The mass spectrum of the product was m / z [H + ]=718. Elemental analysis of the product: calculated values: C, 75.19; H, 3.65; N, 7.79; O,4.45; S, 8.92; found values: C, 75.25; H, 3.67; N, 7.84; O, 4.41; S, 8.89.

[0223] Synthesis of organic compound M8:

[0224] The synthesis of organic compound M8 was carried out according to the synthesis method of organic compound M1, with a yield of 88%. The mass spectrum of the product was m / z [H + ] = 750. Elemental analysis of the product: calculated values: C, 71.97; H, 3.49; N, 7.46; S, 17.08; found values: C, 71.93; H, 3.45; N, 7.48; S, 17.12.

[0225] Synthesis of organic compound M9:

[0226] The synthesis of intermediate 9-2 was carried out according to the synthesis method of intermediate 1-2, with a yield of 83% and a mass spectrum of m / z [H+] = 328.

[0227] The synthesis of intermediate 9-4 was carried out according to the synthesis method of intermediate 1-4, with a yield of 39% and a mass spectrum of m / z [H+] = 319.

[0228] The synthesis of organic compound M9 was carried out according to the synthesis method of organic compound M1, with a yield of 84%. The mass spectrum of the product was m / z [H + ] = 686. Elemental analysis of the product: calculated values: C, 78.71; H, 3.82; N, 8.16; O, 9.32; found values: C, 78.74; H, 3.86; N, 8.12; O, 9.30.

[0229] Synthesis of organic compound M10:

[0230] The synthesis of organic compound M10 was carried out according to the synthesis method of organic compound M1, with a yield of 83%. The mass spectrum of the product was m / z [H + ]=718. Elemental analysis of the product: calculated values: C, 75.19; H, 3.65; N, 7.79; O, 4.45; S, 8.92; found values: C, 75.25; H, 3.68; N, 7.75; O, 4.48; S, 8.98.

[0231] Synthesis of organic compound M11:

[0232] The synthesis of intermediate 11-2 was carried out according to the synthesis method of intermediate 1-2, with a yield of 81% and a mass spectrum of m / z [H+] = 344.

[0233] The synthesis of intermediate 11-4 was carried out according to the synthesis method of intermediate 1-4, with a yield of 31% and a mass spectrum of m / z [H+] = 335.

[0234] The synthesis of organic compound M11 was carried out according to the synthesis method of organic compound M1, with a yield of 84%. The mass spectrum of the product was m / z [H + ]=702. Elemental analysis of the product: calculated values: C, 76.91; H, 3.73; N, 7.97; O, 6.83; S, 4.56; found values: C, 76.94; H, 3.71; N, 7.92; O, 6.81; S, 4.59.

[0235] Synthesis of organic compound M12:

[0236] The synthesis of organic compound M12 was carried out according to the synthesis method of organic compound M1, with a yield of 81%. The mass spectrum of the product was m / z [H +]=734. Elemental analysis of the product: calculated values: C, 73.55; H, 3.57; N, 7.62; O, 2.18; S, 13.09; found values: C, 73.59; H, 3.52; N, 7.67; O, 2.26; S, 13.13.

[0237] Synthesis of organic compound M13

[0238] The synthesis of intermediate 13-3 was carried out according to the synthesis method of intermediate 1-4, with a yield of 61% and a mass spectrum of m / z [H+] = 335.

[0239] The synthesis of organic compound M13 was carried out according to the synthesis method of organic compound M1, with a yield of 84%. The mass spectrum of the product was m / z [H + ]=702. Elemental analysis of the product: calculated values: C, 76.91; H, 3.73; N, 7.97; O, 6.83; S, 4.56; found values: C, 76.95; H, 3.77; N, 7.92; O, 6.85; S, 4.52.

[0240] Synthesis of organic compound M14

[0241] The synthesis of organic compound M14 was carried out according to the synthesis method of organic compound M1, with a yield of 80%. The mass spectrum of the product was m / z [H + ]=734. Elemental analysis of the product: calculated values: C, 73.55; H, 3.57; N, 7.62; O, 2.18; S, 13.09; found values: C, 73.58; H, 3.55; N, 7.66; O, 2.16; S, 13.13.

[0242] Synthesis of organic compound M15

[0243] The synthesis of intermediate 15-3 was carried out according to the synthesis method of intermediate 1-4. The yield was 62% and the mass spectrum of the product was m / z [H+] = 351.

[0244] The synthesis of organic compound M15 was carried out according to the synthesis method of organic compound M1, with a yield of 80%. The mass spectrum of the product was m / z [H +]=718. Elemental analysis of the product: calculated values: C, 75.19; H, 3.65; N, 7.79; O, 4.45; S, 8.92; found values: C, 75.12; H, 3.61; N, 7.77; O, 4.49; S, 8.99.

[0245] Synthesis of organic compound M16

[0246] The synthesis of organic compound M16 was carried out according to the synthesis method of organic compound M1, with a yield of 82%. The mass spectrum of the product was m / z [H + ] = 750. Elemental analysis of the product: calculated values: C, 71.97; H, 3.49; N, 7.46; S, 17.08; found values: C, 71.97; H, 3.49; N, 7.46; S, 17.08.

[0247] Synthesis of organic compound M17

[0248] The synthesis of intermediate 17-2 was carried out according to the synthesis method of intermediate 1-2, with a yield of 88% and a mass spectrum of m / z [H+] = 328.

[0249] The synthesis of intermediate 17-4 was carried out according to the synthesis method of intermediate 1-4, with a yield of 41% and a mass spectrum of m / z [H+] = 319.

[0250] The synthesis of organic compound M17 was carried out according to the synthesis method of organic compound M1, with a yield of 86%. The mass spectrum of the product was m / z [H + ]=686. Elemental analysis of the product: calculated values: C, 78.71; H, 3.82; N, 8.16; O, 9.32; found values: C, 78.76 H, 3.85 N, 8.12 O, 9.31.

[0251] Synthesis of organic compound M18

[0252] The synthesis of organic compound M18 was carried out according to the synthesis method of organic compound M1, with a yield of 84%. The mass spectrum of the product was m / z [H +]=718. Elemental analysis of the product: calculated values: C, 75.19; H, 3.65; N, 7.79; O, 4.45; S, 8.92; found values: C, 75.24; H, 3.62; N, 7.83; O, 4.47; S, 8.98.

[0253] Synthesis of organic compound M19

[0254] The synthesis of intermediate 19-3 was carried out according to the synthesis method of intermediate 1-4, with a yield of 64% and a mass spectrum of m / z [H+] = 335.

[0255] The synthesis of organic compound M19 was carried out according to the synthesis method of organic compound M1, with a yield of 83%. The mass spectrum of the product was m / z [H + ]=702. Elemental analysis of the product: calculated values: C, 76.91; H, 3.73; N, 7.97; O, 6.83; S, 4.56; found values: C, 76.95; H, 3.75; N, 7.92; O, 6.86; S, 4.58.

[0256] Synthesis of organic compound M20

[0257] The synthesis of organic compound M20 was carried out according to the synthesis method of organic compound M1, with a yield of 83%. The mass spectrum of the product was m / z [H + ]=734. Elemental analysis of the product: calculated values: C, 73.55; H, 3.57; N, 7.62; O, 2.18; S, 13.09; found values: C, 73.58; H, 3.59; N, 7.65; O, 2.19; S, 13.15.

[0258] Synthesis of organic compound M21

[0259] The synthesis of intermediate 21-2 was carried out according to the synthesis method of intermediate 1-2, with a yield of 87%. The mass spectrum of the product was m / z [H + ]=344.

[0260] The synthesis of intermediate 21-4 was carried out according to the synthesis method of intermediate 1-4, with a yield of 42%. The mass spectrum of the product was m / z [H + ]=335.

[0261] The synthesis of organic compound M21 was carried out according to the synthesis method of organic compound M1, with a yield of 82%. The mass spectrum of the product was m / z [H + ]=702. Elemental analysis of the product: calculated values: C, 76.91; H, 3.73; N, 7.97; O, 6.83; S, 4.56; found values: C, 76.97; H, 3.76; N, 7.99; O, 6.85; S, 4.66.

[0262] Synthesis of organic compound M22:

[0263] The synthesis of intermediate 22-3 was carried out according to the synthesis method of compound M1, with a yield of 81% and a mass spectrum of m / z [H + ] = 509.

[0264] The synthesis of organic compound M22 was carried out according to the synthesis method of organic compound M1, with a yield of 83%. The mass spectrum of the product was m / z [H + ]=735. Elemental analysis of the product: calculated values: C, 81.61; H, 3.97; N, 5.71; O, 4.35; S, 4.36; found values: C, 81.67; H, 3.96; N, 5.77; O, 4.38; S, 4.38.

[0265] Synthesis of organic compound M23

[0266] The synthesis of organic compound M23 was carried out according to the synthesis method of organic compound M1, with a yield of 83%. The mass spectrum of the product was m / z [H + ]=734. Elemental analysis of the product: calculated values: C, 73.55; H, 3.57; N, 7.62; O, 2.18; S, 13.09; found values: C, 73.58; H, 3.53; N, 7.65; O, 2.15; S, 13.15.

[0267] Synthesis of organic compound M24

[0268] The synthesis of intermediate 24-3 was carried out by referring to the synthesis method of intermediate 1-4 above, with a yield of 67%. The mass spectrum of the product was m / z [H + ]=350.

[0269] The synthesis of organic compound M24 was carried out according to the synthesis method of organic compound M1, with a yield of 81%. The mass spectrum of the product was m / z [H + ]=718. Elemental analysis of the product: calculated values: C, 73.55; H, 3.57; N, 7.62; O, 2.18; S, 13.09; found values: C, 73.58; H, 3.59; N, 7.64; O, 2.23; S, 13.14.

[0270] Synthesis of organic compound M25

[0271] The synthesis of organic compound M25 was carried out according to the synthesis method of organic compound M1, with a yield of 82%. The mass spectrum of the product was m / z [H + ] = 750. Elemental analysis of the product: calculated values: C, 71.97; H, 3.49; N, 7.46; S, 17.08; found values: C, 71.94; H, 3.55; N, 7.48; S, 17.15.

[0272] Synthesis of organic compound M26

[0273] The synthesis of organic compound M26 was carried out according to the synthesis method of organic compound M1, with a yield of 73%. The mass spectrum of the product was m / z [H + ]=808. Elemental analysis of the product: calculated values: C, 75.72; H, 3.49; N, 6.93; O, 5.93; S, 7.93; found values: C, 75.75; H, 3.54; N, 6.98; O, 5.95; S, 7.91.

[0274] Synthesis of organic compound M27

[0275] The synthesis of organic compound M27 was carried out according to the synthesis method of organic compound M1, with a yield of 77%. The mass spectrum of the product was m / z [H + ]=825. Elemental analysis of the product: calculated values: C, 74.25; H, 3.42; N, 6.79; O, 3.88; S, 11.66; found values: C, 74.29; H, 3.46; N, 6.83; O, 3.84; S, 11.69.

[0276] Synthesis of organic compound M28

[0277] The synthesis of organic compound M28 was carried out according to the synthesis method of organic compound M1, with a yield of 73%. The mass spectrum of the product was m / z [H + ]=808. Elemental analysis of the product: calculated values: C, 75.72; H, 3.49; N, 6.93; O, 5.93; S, 7.93; found values: C, 75.73; H, 3.52; N, 6.94; O, 5.96; S, 7.96.

[0278] Synthesis of organic compound M29

[0279] The synthesis of organic compound M29 was carried out according to the synthesis method of organic compound M1, with a yield of 77%. The mass spectrum of the product was m / z [H + ]=825. Elemental analysis of the product: calculated values: C, 74.25; H, 3.42; N, 6.79; O, 3.88; S, 11.66; found values: C, 74.24; H, 3.44; N, 6.89; O, 3.86; S, 11.75.

[0280] Synthesis of organic compound M30:

[0281] The synthesis of organic compound M30 was carried out according to the synthesis method of organic compound M1, with a yield of 85%. The mass spectrum of the product was m / z [H + ]=734. Elemental analysis of the product: calculated values: C, 73.55; H, 3.57; N, 7.62; O, 2.18; S, 13.09; found values: C, 73.57; H, 3.56; N, 7.64; O, 2.15; S, 13.13.

[0282] Synthesis of organic compound M31:

[0283] The synthesis of organic compound M31 was carried out according to the synthesis method of organic compound M1, with a yield of 80%. The mass spectrum of the product was m / z [H +]=702. Elemental analysis of the product: calculated values: C, 76.91; H, 3.73; N, 7.97; O, 6.83; S, 4.56; found values: C, 76.95; H, 3.77; N, 7.95; O, 6.88; S, 4.59.

[0284] Synthesis of organic compound M32:

[0285] The synthesis of intermediate 32-3 was carried out according to the synthesis method of compound M1, with a yield of 73%. The mass spectrum of the product was m / z [H + ]=509.

[0286] The synthesis of organic compound M32 was carried out according to the synthesis method of organic compound M1, with a yield of 81%. The mass spectrum of the product was m / z [H + ]=725. Elemental analysis of the product: calculated values: C, 79.43; H, 3.75; N, 5.79; O, 6.61; S, 4.42; found values: C, 79.47; H, 3.71; N, 5.84; O, 6.65; S, 4.45.

[0287] Synthesis of organic compound M33:

[0288] The synthesis of intermediate 33-3 was carried out according to the synthesis method of compound M1, with a yield of 77%. The mass spectrum of the product was m / z [H + ]=509.

[0289] The synthesis of organic compound M33 was carried out according to the synthesis method of organic compound M1, with a yield of 85%. The mass spectrum of the product was m / z [H + ]=725. Elemental analysis of the product: calculated values: C, 79.43; H, 3.75; N, 5.79; O, 6.61; S, 4.42; found values: C, 79.48; H, 3.75; N, 5.82; O, 6.63; S, 4.49.

[0290] Synthesis of organic compound M34:

[0291] The synthesis of intermediate 34-3 was carried out according to the synthesis method of compound M1, with a yield of 76%. The mass spectrum of the product was m / z [H + ]=525.

[0292] The synthesis of organic compound M34 was carried out according to the synthesis method of organic compound M1, with a yield of 81%. The mass spectrum of the product was m / z [H + ]=791. Elemental analysis of the product: calculated values: C, 78.87; H, 3.69; N, 5.31; O, 4.04; S, 8.10; found values: C, 78.89; H, 3.63; N, 5.35; O, 4.08; S, 8.15.

[0293] Synthesis of organic compound M35:

[0294] The synthesis of intermediate 35-3 was carried out according to the synthesis method of compound M1, with a yield of 73%. The mass spectrum of the product was m / z [H + ]=525.

[0295] The synthesis of organic compound M35 was carried out according to the synthesis method of organic compound M1, with a yield of 81%. The mass spectrum of the product was m / z [H + ]=791. Elemental analysis of the product: calculated values: C, 78.87; H, 3.69; N, 5.31; O, 4.04; S, 8.10; found values: C, 78.83; H, 3.64; N, 5.35; O, 4.07; S, 8.15.

[0296] Synthesis of organic compound M36:

[0297] The synthesis of organic compound M36 was carried out according to the synthesis method of organic compound M1, with a yield of 81%. The mass spectrum of the product was m / z [H + ]=791. Elemental analysis of the product: calculated values: C, 80.56; H, 3.97; N, 6.13; O, 4.67; S, 4.67; found values: C, 80.58; H, 3.96; N, 6.16; O, 4.63; S, 4.69.

[0298] Synthesis of organic compound M37:

[0299] The synthesis of intermediate 37-2 was carried out according to the synthesis method of intermediate 1-2, with a yield of 87%. The mass spectrum of the product was m / z [H + ]=320.

[0300] The synthesis of intermediate 37-4 was carried out according to the synthesis method of intermediate 1-4, with a yield of 65%. The mass spectrum of the product was m / z [H + ]=367.

[0301] The synthesis of organic compound M37 was carried out according to the synthesis method of organic compound M1, with a yield of 87%. The mass spectrum of the product was m / z [H + ]=702. Elemental analysis of the product: calculated values: C, 76.91; H, 3.73; N, 7.97; O, 6.83; S, 4.56; found values: C, 76.95; H, 3.78; N, 7.96; O, 6.86; S, 4.58.

[0302] Synthesis of organic compound M38:

[0303] The synthesis of intermediate 38-2 was carried out according to the synthesis method of intermediate 1-2, with a yield of 81%. The mass spectrum of the product was m / z [H + ]=320.

[0304] The synthesis of intermediate 38-4 was carried out according to the synthesis method of intermediate 1-4, with a yield of 56%. The mass spectrum of the product was m / z [H + ]=367.

[0305] The synthesis of organic compound M38 was carried out according to the synthesis method of organic compound M1, with a yield of 81%. The mass spectrum of the product was m / z [H + ]=702. Elemental analysis of the product: calculated values: C, 76.91; H, 3.73; N, 7.97; O, 6.83; S, 4.56; found values: C, 76.92; H, 3.73; N, 7.99; O, 6.88; S, 4.65.

[0306] Synthesis of organic compound M39:

[0307] The synthesis of intermediate 39-2 was carried out according to the synthesis method of intermediate 1-2, with a yield of 82%. The mass spectrum of the product was m / z [H + ]=320.

[0308] The synthesis of intermediate 39-4 was carried out according to the synthesis method of intermediate 1-4, with a yield of 61%. The mass spectrum of the product was m / z [H + ]=367.

[0309] The synthesis of organic compound M39 was carried out according to the synthesis method of organic compound M1, with a yield of 79%. The mass spectrum of the product was m / z [H + ]=702. Elemental analysis of the product: calculated values: C, 76.91; H, 3.73; N, 7.97; O, 6.83; S, 4.56; found values: C, 76.95; H, 3.78; N, 7.96; O, 6.86; S, 4.58.

[0310] Synthesis of organic compound M40:

[0311] The synthesis of intermediate 40-2 was carried out according to the synthesis method of intermediate 1-2, with a yield of 78%. The mass spectrum of the product was m / z [H + ]=320.

[0312] The synthesis of intermediate 40-4 was carried out according to the synthesis method of intermediate 1-4, with a yield of 54%. The mass spectrum of the product was m / z [H + ]=367.

[0313] The synthesis of organic compound M40 was carried out according to the synthesis method of organic compound M1, with a yield of 74%. The mass spectrum of the product was m / z [H + ]=702. Elemental analysis of the product: calculated values: C, 76.91; H, 3.73; N, 7.97; O, 6.83; S, 4.56; found values: C, 76.88; H, 3.79; N, 7.94; O, 6.86; S, 4.64.

[0314] Synthesis of organic compound M41:

[0315] The synthesis of intermediate 41-2 was carried out according to the synthesis method of intermediate 1-2, with a yield of 74%. The mass spectrum of the product was m / z [H + ]=320.

[0316] The synthesis of intermediate 41-4 was carried out according to the synthesis method of intermediate 1-4, with a yield of 52%. The mass spectrum of the product was m / z [H + ]=367.

[0317] The synthesis of organic compound M41 was carried out according to the synthesis method of organic compound M1, with a yield of 77%. The mass spectrum of the product was m / z [H +]=702. Elemental analysis of the product: calculated values: C, 76.91; H, 3.73; N, 7.97; O, 6.83; S, 4.56; found values: C, 76.95; H, 3.75; N, 7.96; O, 6.87; S, 4.62.

[0318] Synthesis of organic compound M42:

[0319] The synthesis of intermediate 42-3 was carried out according to the synthesis method of intermediate 1-4, with a yield of 38%. The mass spectrum of the product was m / z [H + ]=320.

[0320] The synthesis of organic compound M42 was carried out according to the synthesis method of organic compound M1, with a yield of 84%. The mass spectrum of the product was m / z [H + ] = 687. Elemental analysis of the product: calculated values: C, 76.85; H, 3.66; N, 10.18; O, 9.31; found values: C, 76.89; H, 3.69; N, 10.14; O, 9.36.

[0321] Synthesis of organic compound M43:

[0322] The synthesis of intermediate 43-3 was carried out by referring to the synthesis method of intermediate 1-4 above, with a yield of 61%. The mass spectrum of the product was m / z [H + ]=336.

[0323] The synthesis of organic compound M43 was carried out according to the synthesis method of organic compound M1, with a yield of 81%. The mass spectrum of the product was m / z [H + ]=703. Elemental analysis of the product: calculated values: C, 75.09; H, 3.58; N, 9.95; O, 6.82; S, 4.56; found values: C, 75.14; H, 3.54; N, 9.98; O, 6.89; S, 4.58.

[0324] Synthesis of organic compound M44:

[0325] The synthesis of organic compound M44 was carried out according to the synthesis method of organic compound M1, with a yield of 82%. The mass spectrum of the product was m / z [H +]=704. Elemental analysis of the product: calculated values: C, 73.28; H, 3.43; N, 11.92; O, 6.81; S, 4.55; found values: C, 73.22; H, 3.47; N, 11.95; O, 6.84; S, 4.58.

[0326] Comparative Example This application also provides a comparative example, which is recorded as "Ref-01", and its chemical structure is shown below:

[0327] Refractive index of organic compounds The compound was vacuum-deposited onto single-crystal silicon to form a 60 nm thin film. The single-crystal silicon was placed on the sample stage of an ellipsometer (ES-01) with an incident angle of 70° and the test was conducted in an atmospheric environment. The refractive index (n) of the compound was measured using the ellipsometer. The refractive index n values ​​of the compound at different wavelengths are shown in Tables 1-1 and 1-2: Table 1-1

[0328] Table 1-2

[0329] From the data analysis in Table 1-1 and Table 1-2, it can be seen that the refractive index of the organic compounds M1 to M44 provided in the embodiments of the present application in each wavelength region is significantly higher than the refractive index of the organic compound Ref-01 in Comparative Example 1, which will greatly help improve the light extraction efficiency of the electronic device 12.

[0330] Preparation and characterization of OLED devices The following is a detailed description of the preparation method and process of the OLED device prepared by the compound of the present application through a specific device 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) / covering layer (60nm). In the following preparation method for preparing an OLED device, ITO conductive glass is used as the anode substrate, PD is used as a hole injection material, HT is used as a hole transport material, BH is used as the main material of the light-emitting layer 233, BD is used as the doping material of the light-emitting layer 233, ET and Liq are used as electron transport materials, Liq is used as an electron injection material, and Al is used as a cathode material. In addition, the organic compounds described in the aforementioned synthesis embodiment are used as the material of the covering layer 30 to prepare corresponding OLED devices. Among them, the chemical structures of PD, HT, BH, BD, ET and Liq are as follows:

[0331] The following is a detailed description of a method for preparing an OLED device using an organic compound M1 as the material for the cover layer 30. The prepared OLED device is referred to as "device 1." The preparation method of device 1 includes the following steps: a. Cleaning of the conductive glass substrate: using chloroform, ketone, isopropyl alcohol for cleaning, followed by UV ozone plasma treatment; b. Preparation of functional layer: First, the ITO substrate was moved into a vacuum vapor deposition device under high vacuum (1×10 -6 mbar), using resistive heating evaporation at 1 Å s -1 The hole injection materials PD and HT were evaporated on the ITO at a deposition rate of 3:97, and a hole injection layer 231 with a thickness of 10 nm was obtained. -1 The hole transport material HT was evaporated on the hole injection layer 231 at a deposition rate of 1 Å / s to obtain a hole transport layer 232 with a thickness of 130 nm. Next, BH and BD were evaporated on the hole transport layer 232 at a deposition rate of 1 Å / s, with a deposition rate ratio of 97:3, to obtain a light-emitting layer 233 with a thickness of 40 nm. Subsequently, the electron transport material ET and Liq were placed in different evaporation crucibles in a vacuum chamber and heated in a high vacuum environment (1×10 -6 ET and Liq were co-deposited at a weight ratio of 5:5 under 100 mbar to form an electron transport layer 234 with a thickness of 30 nm on the light emitting layer 233. -1The electron injection material Liq was evaporated on the electron transport layer 234 at a deposition rate of 1 Å s to obtain an electron injection layer 235 with a thickness of 1 nm. -1 The cathode material Al was evaporated on the electron injection layer 234 at a deposition rate of 100 nm to obtain a second electrode 22 with a thickness of 100 nm. On the second electrode 22, an organic compound M1 was vacuum evaporated to form a covering layer 30 with a thickness of 60 nm.

[0332] c. Packaging: The device is encapsulated with UV-curable resin in a nitrogen glove box to obtain an OLED device.

[0333] Referring to the preparation method of device 1, organic compounds M2 to M44 synthesized in the examples were selected as the materials for the cover layer 30 of the OLED devices, respectively, to produce devices 2 to 44. It will be appreciated that, in the preparation methods of devices 1 to 44, except for the materials for the cover layer 30, all other experimental conditions were the same.

[0334] Furthermore, referring to the preparation methods of the device examples, comparative compound Ref-01 was used as the material for cover layer 30 to prepare comparative device 1. Except for the material for cover layer 30, the other experimental conditions in the preparation method of comparative device 1 were the same as those of device 1.

[0335] In the embodiment of the present application, the current-voltage ( JV ) characteristics and record the luminous efficiency. The luminous efficiency is the current density of 10mA cm -2 The specific data are shown in Table 2.

[0336] Table 2

[0337] As can be seen from Table 2, compared with the comparative device 1, the electronic device 12 prepared by using the organic compound M1 to M44 provided in the embodiment of the present application and having a core structure of dibenzofuran or dibenzothiophene substituted by a heterocyclic group containing nitrogen atoms, oxygen atoms or sulfur atoms as the covering layer 30 can significantly improve the luminous efficiency; wherein, the organic compound provided in the embodiment of the present application has a core structure of dibenzofuran or dibenzothiophene substituted by a heterocyclic group containing nitrogen atoms, oxygen atoms or sulfur atoms, which can obtain a high electron cloud density and polarizability; wherein, the organic compound M1 to M4 ... Aromatic rings containing heteroatoms have lone pairs of electrons or electron-rich π systems, which increase the instantaneous dipole moment of organic compounds, significantly improving their electronic polarizability. The greater the polarizability, the higher the refractive index of the organic compound. Furthermore, organic compounds exhibit rigid planar and dense packing. Five- or six-membered heterocyclic rings in organic compounds inherently possess rigid planar structures that can be bridged with benzene rings, condensed aromatic hydrocarbons, or heteroaromatic hydrocarbons to form long-range conjugated planar skeletons, promoting intermolecular π-π stacking and increasing the density of the resulting film. Higher density translates to a greater unit volume polarizability, leading to a higher volume refractive index.

[0338] In addition, an embodiment of the present application further provides a display panel, which includes the electronic device described in the above embodiment.

[0339] It can be understood that, since the display panel includes the same electronic components as those in the above embodiment, the display panel has the same beneficial effects as the electronic components, which will not be described in detail here.

[0340] The above-described embodiments merely represent several implementation methods of the present application. While the descriptions are relatively specific and detailed, they should not be construed as limiting the scope of the patent application. It should be noted that a person of ordinary skill in the art may make various modifications and improvements without departing from the spirit of the present application, and these modifications and improvements fall within the scope of protection of the present application. Therefore, the scope of protection of the present patent application shall be determined by the appended claims.

Claims

1. An organic compound, characterized in that The organic compound has a structure as shown in formula (1): （1）； wherein X, Y and Z are the same or different and are independently selected from oxygen atoms or sulfur atoms; W and V are the same or different and are independently selected from CH or a nitrogen atom; L1 and L2 are the same or different and are independently selected from at least one of a single bond, a substituted or unsubstituted aromatic group having 6 to 25 carbon atoms, and a substituted or unsubstituted heteroaromatic group having 5 to 25 carbon atoms; Ar is selected from at least one of a hydrogen atom, a substituted or unsubstituted aromatic group having 6 to 25 carbon atoms, and a substituted or unsubstituted heteroaromatic group having 5 to 25 carbon atoms; The substituents in the substituted or unsubstituted L1, L2 and Ar are at least one selected from an aromatic group having 6 to 25 carbon atoms and a heteroaromatic group having 5 to 25 carbon atoms; The heteroatom of the heteroaryl group in L1, L2 and Ar is at least one selected from a nitrogen atom, an oxygen atom and a sulfur atom.

2. The organic compound according to claim 1, characterized in that L1 and L2 are the same or different and are independently selected from at least one of a single bond, a phenyl group, a naphthyl group, a biphenyl group, a pyridyl group, a pyrazinyl group, a carbazolyl group, a phenanthrenyl group, a triphenylene group, an o-phenanthroline group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzoxazolyl group, a benzothiazolyl group, a naphthofuranyl group, a naphthothiophenyl group, a benzo[k]xanthenyl group, a benzo[4,5-bcd]furanyl group, a benzo[k]thioanthenyl group and a benzo[4,5-bcd]thiophenyl group.

3. The organic compound according to claim 1, characterized in that Ar is selected from at least one of a hydrogen atom, a phenyl group, a benzoxazolyl group, a benzothiazolyl group, a phenanthryl group, a pyrene group, a triphenylene group, a phenanthroline group, a dibenzofuranyl group, a dibenzothiophenyl group, an N-phenylcarbazolyl group, a quinolyl group, an isoquinolyl group, a quinoxalinyl group, a naphthobenzofuranyl group, a naphthobenzothiophenyl group, a phenanthrobenzofuranyl group and a triphenylene group.

4. The organic compound according to claim 1, characterized in that The substituents in the substituted or unsubstituted groups of L1, L2 and Ar are at least one selected from the group consisting of phenyl, pyridyl, benzoxazolyl, benzothiazolyl, quinolyl, isoquinolyl and quinoxalinyl.

5. The organic compound according to claim 1, characterized in that The organic compound is selected from any one of the following compounds: 。 6. The organic compound according to any one of claims 1 to 5, characterized in that The refractive index of the organic compound for light with a wavelength of 620 nm is greater than 1.75; The extinction coefficient of the organic compound to light with a wavelength of 430 nm is less than 0.

1.

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

8. The composition according to claim 7, characterized in that The mass proportion of the organic compound in the composition is greater than or equal to 0.01% and less than or equal to 20%.

9. An electronic device, characterized in that: The electronic device comprises: a first electrode; an organic functional layer, disposed on one side of the first electrode; a second electrode, disposed on a side of the organic functional layer away from the first electrode; A covering layer is provided on a side of the second electrode away from the organic functional layer, wherein the material of the covering layer comprises at least one organic compound according to any one of claims 1 to 6, or the covering layer is made of the composition according to claim 7 or 8.

10. A display panel, characterized in that: The display panel includes the electronic device according to claim 9.

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