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

Abstract

The invention relates to an organic compound, a composition, an organic light-emitting device and a display panel. The organic compound has a structure as shown in a formula (1): # imgabs0 #, wherein X1 and X2 are selected from N or CH; y is selected from O or S; l1, L2 and L3 are respectively and independently selected from a single bond, a substituted or unsubstituted aryl group with the carbon atom number of 6 to 20, and a substituted or unsubstituted heteroaryl group with the carbon atom number of 4 to 20; r is selected from H, methyl or phenyl, and m is selected from any integer from 0 to 3; ar1 is selected from substituted or unsubstituted aryl with the carbon atom number of 6 to 20 and substituted or unsubstituted heteroaryl with the carbon atom number of 2 to 20; the organic compound provided by the embodiment of the invention has relatively high glass transition temperature and thermal stability; meanwhile, high extinction can be realized in an ultraviolet region, low extinction can be realized in a visible region, and a high refractive index is realized; the material can be used as a light extraction layer of the organic light-emitting device to protect the interior of the device from being damaged by harmful light and improve the light extraction efficiency of the organic light-emitting device.

Description

Technical Field

[0001] This application relates to the field of display technologies, and particularly to an organic compound, a composition, an organic light-emitting device, and a display panel. Background Art

[0002] An organic light-emitting diode (OLED) is an advanced self-emitting display technology. It generates excitons through the transfer and recombination of charge carriers between different functional layers, and these excitons emit light through organic compounds or metal complexes with high quantum efficiency. The OLED technology is known for its advantages such as self-emission, high brightness, high efficiency, high contrast, and fast response time.

[0003] In recent years, the luminous efficiency of OLEDs has been significantly improved, and its internal quantum efficiency has approached the theoretical limit. Therefore, improving the light extraction efficiency has become the key to further enhancing the device stability and current efficiency. For example, by optimizing the stacking of metal complexes in the emission layer and the refractive index matching between different 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 deposit an inorganic compound ZnSe with a high refractive index (n = 2.6) on the cathode to improve the light extraction efficiency by utilizing the difference in refractive indices between functional layers. However, due to the high evaporation temperature and slow evaporation rate of inorganic materials, the application of such compounds in OLED devices is limited.

[0004] In view of these challenges, researchers have begun to explore organic compounds with high refractive indices in order to improve the light extraction efficiency in electroluminescent devices. An ideal compound should meet the following conditions: having a high extinction coefficient in the ultraviolet band (less than 400 nanometers) to protect the device materials from harmful light; having an extinction coefficient close to zero in the visible light range (greater than 430 nanometers) to ensure high transmittance of visible light and reduce the impact on the light output efficiency; having a high refractive index and small variation in the visible light range to improve the light output efficiency and optimize the device structure; and having a relatively high glass transition temperature to enhance the thermal stability.

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

[0006] Embodiments of this application provide an organic compound, a composition, an organic light-emitting device, and a display panel, which have a relatively high refractive index. When used as the light extraction layer of an organic light-emitting device, they can effectively protect the internal structure of the device from harmful light damage, improve the light output efficiency, and optimize the device performance.

[0007] An embodiment of the present application provides an organic compound, and the organic compound has a structure shown in formula (1):

[0008]

[0009] Wherein, X 1 and X 2 are each independently selected from N or CH;

[0010] Y is selected from O or S;

[0011] L 1 、L 2 and L 3 are each independently selected from a single bond, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroaryl group having 4 to 20 carbon atoms;

[0012] R is selected from H, methyl or phenyl, and m is any integer from 0 to 3;

[0013] Ar 1 is selected from a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

[0014] In one embodiment of the present application, X 1 is selected from N, and X 2 is selected from N or CH.

[0015] In one embodiment of the present application, L 1 、L 2 and L 3 are each independently selected from a single bond, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, dibenzofuranyl or phenyl-substituted carbazolyl.

[0016] In one embodiment of the present application, Ar 1Selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted benzophenanthrene, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted furyl, substituted or unsubstituted naphthofuranophenyl, substituted or unsubstituted thienyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted dibenzofuryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted N-phenylcarbazolyl, substituted or unsubstituted N-biphenylcarbazolyl, substituted or unsubstituted N-naphthylcarbazolyl, substituted or unsubstituted N-dibenzofurylcarbazolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted cinnolinyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolinyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted naphthofuryl, substituted or unsubstituted naphthothienyl.

[0017] In one embodiment of the present application, Ar 1 is selected from phenyl, benzoxazolyl or benzothiazolyl.

[0018] In one embodiment of the present application, the structure of the organic compound is as shown in formula (2-1) or formula (2-2):

[0019]

[0020] In one embodiment of the present application, the structure of the organic compound is as shown in formula (3-1) or formula (3-2):

[0021]

[0022] For the above object of the embodiments of the present application, the embodiments of the present application further provide a composition, the composition includes at least one organic solvent and at least one of the organic compounds.

[0023] For the above object of the embodiments of the present application, the embodiments of the present application further provide an organic light-emitting device, the organic light-emitting device includes:

[0024] A first electrode;

[0025] An organic functional layer disposed on one side of the first electrode;

[0026] A second electrode, disposed on a side of the organic functional layer away from the first electrode;

[0027] A light extraction layer, disposed on a side of the second electrode away from the organic functional layer, wherein the material of the light extraction layer comprises at least one of the organic compounds, or the material of the light extraction layer comprises the composition.

[0028] For the above object of the embodiments of the present application, the embodiments of the present application further provide a display panel, and the display panel includes the organic light-emitting device.

[0029] The present application provides an organic compound, a composition, an organic light-emitting device and a display panel. The organic compound has a large nitrogen-containing conjugated plane feature, so that the organic compound has a high glass transition temperature and thermal stability; at the same time, it can have high extinction in the ultraviolet region and low extinction in the visible region, and has a high refractive index; when the organic compound is used as the light extraction layer of the organic light-emitting device, it can effectively protect the internal structure of the device from harmful light damage, and improve the light extraction efficiency of the organic light-emitting device, and optimize the device performance.

[0030] Other features and advantages of the present application will be described in detail in the subsequent specific implementation section. Description of the Drawings

[0031] In order to more clearly illustrate the technical solutions in the embodiments of the present application, the drawings required for the description of the embodiments will be briefly introduced below. Obviously, the drawings in the following description are only some embodiments of the present application, and those skilled in the art can obtain other drawings according to these drawings without creative efforts.

[0032] In order to more fully understand the present application and its beneficial effects, the following description will be made in conjunction with the drawings, where the same reference numerals represent the same parts in the following description.

[0033] Figure 1 FIG. is a schematic structural diagram of an organic light-emitting device provided by an embodiment of the present application.

[0034] Description of the Reference Numerals:

[0035] 10. Organic light-emitting device; 11. First electrode; 12. Second electrode; 20. Organic functional layer; 21. Hole injection layer; 22. Hole transport layer; 23. Light-emitting layer; 24. Electron transport layer; 25. Electron injection layer; 30. Light extraction layer. Detailed Description of the Embodiments

[0036] Next, the technical solutions in the embodiments of the present application will be clearly and completely described in conjunction with the accompanying drawings in the embodiments of the present application. Obviously, the described embodiments are only a part of the embodiments of the present application, rather than all the embodiments. Based on the embodiments in the present application, all other embodiments obtained by those skilled in the art without creative efforts fall within the protection scope of the present application.

[0037] In the embodiments of the present application, the aryl group having 6 to 20 carbon atoms refers to a monovalent group including a carbocyclic aromatic system having 6 to 30 carbon atoms as ring-forming atoms. Non-limiting examples of the aryl group having 6 to 20 carbon atoms may include phenyl, biphenyl, phenanthryl, terphenyl, naphthyl, phenanthryl, benzophenanthryl, etc.

[0038] In the embodiments of the present application, the heteroaryl group having 2 to 20 carbon atoms refers to a monovalent group including a carbocyclic aromatic system having at least one heteroatom selected from N, O, P, and S as ring-forming atoms and 2 to 20 carbon atoms. Non-limiting examples of the heteroaryl group having 2 to 20 carbon atoms may include pyridyl, oxadiazolyl, triazinyl, pyrimidinyl, furyl, dibenzofuranyl, dibenzothiophenyl, benzoxazolyl, bisbenzoxazolyl, carbazolyl, N-phenylcarbazolyl, quinolinyl, isoquinolinyl, naphthofuranyl, phenyl-substituted naphthofuranyl, etc.

[0039] The embodiments of the present application provide an organic compound having a structure shown in formula (1):

[0040]

[0041] Wherein, X 1 and X 2 are each independently selected from N or CH;

[0042] Y is selected from O or S;

[0043] L 1 、L 2 and L 3 are each independently selected from a single bond, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroaryl group having 4 to 20 carbon atoms;

[0044] R is selected from H, methyl or phenyl, and m is selected from any integer from 0 to 3;

[0045] Ar 1 is selected from a substituted or unsubstituted aryl group having 6 to 20 carbon atoms and a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

[0046] In the implementation and application process, the organic compound has a large nitrogen-containing conjugated planar feature, making the organic compound have a high glass transition temperature and thermal stability; at the same time, it can have high extinction in the ultraviolet region, low extinction in the visible region, and a high refractive index; when the organic compound is used as the light extraction layer of an organic light-emitting device, it can effectively protect the internal structure of the device from harmful light damage and improve the light extraction efficiency of the organic light-emitting device, optimizing the device performance.

[0047] It should be noted that in the general formula provided in the embodiments of the present application, the expression of the ring structure crossed by "—" indicates that the connection site can be any position on the ring structure where bonding can occur.

[0048] Specifically, in some embodiments, X 1 is selected from N, X 2 is selected from N or CH.

[0049] In some embodiments, L 1 、L 2 and L 3 are each independently selected from a single bond, phenyl, biphenylyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, dibenzofuranyl or phenyl-substituted carbazolyl.

[0050] Furthermore, in some embodiments, L 1 、L 2 and L 3 are each independently selected from a single bond, phenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, dibenzofuranyl or phenyl-substituted carbazolyl.

[0051] In some embodiments, Ar 1Selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted benzophenanthrene, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted furyl, substituted or unsubstituted naphthofurobiphenyl, substituted or unsubstituted thienyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted dibenzofuryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted N-phenylcarbazolyl, substituted or unsubstituted N-biphenylcarbazolyl, substituted or unsubstituted N-naphthylcarbazolyl, substituted or unsubstituted N-dibenzofurylcarbazolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted cinnolinyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolinyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted naphthofuryl, substituted or unsubstituted naphthothienyl.

[0052] Wherein, the substituents in the "substituted or unsubstituted" can be selected from one or more of phenyl, naphthyl, biphenyl, terphenyl, fluorenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, quinoxalinyl, quinazolinyl, cinnolinyl, naphthyridinyl, fluorenyl, dibenzofuryl, N-phenylcarbazolyl, dibenzothienyl, naphthofuryl, naphthothienyl.

[0053] In some embodiments, Ar 1 is selected from phenyl, benzoxazolyl or benzothiazolyl.

[0054] In some embodiments, the structure of the organic compound is shown in formula (2-1) or formula (2-2):

[0055]

[0056] It can be understood that in formula (2-1) and formula (2-1), Ar 1 , L 1 , L 2 , L 3 , R, Y and m have the same meanings as described in the above embodiments.

[0057] In some embodiments, the structure of the organic compound is shown in formula (3-1) or formula (3-2):

[0058]

[0059]

[0060] It is understood that the meanings of L 1 、L 2 、L 3 、R, Y and m are the same as those described in the above embodiments. In some embodiments, the organic compound is selected from any one of the following compounds:

[0061]

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078] It should be noted that for the examples of the organic compounds provided in the embodiments of the present application listed above, H in the structural formula can be further arbitrarily substituted, especially deuterated.

[0079] The organic compound provided by the embodiment of the present application has a relatively high glass transition temperature, which can improve the thermal stability of the organic compound. In some embodiments, the glass transition temperature T g is greater than or equal to 100 °C. In a preferred embodiment, T g is greater than or equal to 120 °C. In a more preferred embodiment, T g is greater than or equal to 140 °C. In a still more preferred embodiment, T g is greater than or equal to 160 °C. In a most preferred embodiment, T g is greater than or equal to 180 °C.

[0080] In some embodiments, the refractive index of the organic compound provided by the embodiment of the present application at a wavelength of 630 nm is greater than 1.7; preferably, the refractive index of the organic compound at a wavelength of 630 nm is greater than 1.78; more preferably, the refractive index of the organic compound at a wavelength of 630 nm is greater than 1.83.

[0081] 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.

[0082] In some embodiments, the organic compound has a small 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. The organic compound has a high transmittance to visible light, reducing the impact on the light output efficiency of the device.

[0083] In some embodiments, the organic compound has a large extinction coefficient in the wavelength range of less than or equal to 400 nm; preferably, the extinction coefficient of the organic compound at a wavelength of 350 nm is greater than or equal to 0.3; more preferably, the extinction coefficient of the organic compound at a wavelength of 350 nm is greater than or equal to 0.5; still more preferably, the extinction coefficient of the organic compound at a wavelength of 350 nm is greater than or equal to 0.7; most preferably, the extinction coefficient of the organic compound at a wavelength of 350 nm is greater than or equal to 1.0. An object of the embodiment of the present application is to provide a material solution for evaporation-type OLEDs.

[0084] 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, very 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.

[0085] Another object of the embodiments of the present application is to provide a material solution for printed OLEDs.

[0086] 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.

[0087] In some other embodiments, at 25 °C, the solubility of the organic compound in toluene is greater than or equal to 2 mg / ml, preferably greater than or equal to 3 mg / ml, more preferably greater than or equal to 4 mg / ml, and most preferably greater than or equal to 5 mg / ml.

[0088] The embodiments of the present application also provide a composition, comprising at least one organic solvent and at least one organic compound as described in the above embodiments; at least one of the organic solvents is selected from aromatic or heteroaromatic, esters, aromatic ketones or aromatic ethers, aliphatic ketones or aliphatic ethers, cycloaliphatic or olefinic compounds, or borate or phosphate compounds, or a mixture of two or more solvents.

[0089] In some embodiments, at least one of the organic solvents is selected from aromatic or heteroaromatic-based solvents, especially aliphatic chain / ring-substituted aromatic solvents, or aromatic ketone solvents, or aromatic ether solvents.

[0090] In some embodiments, the organic solvent includes, but is not limited to: aromatic or heteroaromatic-based solvents: p-diisopropylbenzene, amylbenzene, tetralin, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylcumene, dipentylbenzene, tripentylbenzene, amyltoluene, 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-methylcumene, 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-(phenyloxiranyl)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-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-ethylbenzyl ethyl ether, 1,2,4-trimethoxybenzene, 4-(1-propenyl)-1,2-dimethoxybenzene, 1,3-dimethoxybenzene, glycidyl phenyl ether, dibenzyl ether, 4-tert-butylanisole, trans-p-propenylanisole, 1,2-dimethoxybenzene, 1-methoxynaphthalene, diphenyl ether, 2-phenoxymethyl ether, 2-phenoxytetrahydrofuran, ethyl-2-naphthyl ether, pentyl 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, alkanolactone, alkyl oleate, etc.

[0091] In some embodiments, the organic solvent includes aliphatic ketones, such as 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, such as pentyl ether, hexyl ether, dioctyl ether, ethylene glycol dibutyl ether, diethylene glycol diethyl ether, diethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, triethylene glycol ethyl methyl ether, triethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, etc.

[0092] In other embodiments, the organic solvent may further include: 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, tetralin, decalin, indene, and / or mixtures thereof.

[0093] In a preferred embodiment, the composition is a solution.

[0094] In another preferred embodiment, the composition is a suspension.

[0095] The composition in the embodiments of the present application may include 0.01 to 20 wt% of the organic compound, preferably the mass ratio range of the organic compound is 0.1 to 15 wt%, more preferably the mass ratio range of the organic compound is 0.2 to 10 wt%, and most preferably the mass ratio range of the organic compound is 0.25 to 5 wt%.

[0096] The embodiments of the present application also relate to the use of the composition as a coating or printing ink in the preparation of organic light-emitting devices, and particularly preferably the preparation method by printing or coating.

[0097] Among them, suitable printing or coating techniques include (but are not limited to) inkjet printing, nozzle printing, letterpress printing, screen printing, dip coating, spin coating, blade coating, roller printing, reverse roll printing, lithographic printing, flexographic printing, rotary printing, spraying, brush coating, pad printing, slot die coating, etc. Gravure printing, nozzle printing, and inkjet printing are preferred. The solution or suspension may additionally include one or more components such as surface active compounds, lubricants, wetting agents, dispersants, water repellents, adhesives, etc., for adjusting viscosity, film-forming properties, improving adhesion, etc. For detailed information on printing techniques and their related requirements for the relevant solutions, such as solvents and concentrations, viscosities, etc., please refer to "Handbook of Print Media: Technologies and Production Methods" edited by Helmut Kipphan, ISBN 3-540-67326-1.

[0098] In addition, please refer to Figure 1 Furthermore, an organic light-emitting device 10 is provided in an embodiment of the present application. The organic light-emitting device 10 includes a first electrode 11, an organic functional layer 20, a second electrode 12, and a light extraction layer 30.

[0099] Among them, the organic functional layer 20 is disposed on one side of the first electrode 11, the second electrode 12 is disposed on the side of the organic functional layer 20 away from the first electrode 11, the light extraction layer 30 is disposed on the side of the second electrode 12 away from the organic functional layer 20, and the material of the light extraction layer 30 includes at least one of the organic compounds described in the above embodiments, or the material of the light extraction layer 30 includes the composition.

[0100] In some embodiments, the organic light-emitting device 10 may include an organic light-emitting diode, an organic photovoltaic cell, an organic light-emitting battery, 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 plasmonic emission diode, etc. An organic light-emitting diode is particularly preferred.

[0101] In some embodiments, the organic functional layer 20 includes a hole injection layer 21 disposed between the first electrode 11 and the second electrode 12, a hole transport layer 22 disposed between the hole injection layer 21 and the second electrode 12, a light-emitting layer 23 disposed between the hole transport layer 22 and the second electrode 12, an electron transport layer 24 disposed between the light-emitting layer 23 and the second electrode 12, and an electron injection layer 25 disposed between the electron transport layer 24 and the second electrode 12.

[0102] In some embodiments, the organic compound provided in the embodiments of the present application can be used as a material for the electron transport layer 24, or a host material for the light-emitting layer 23, or a material for the light extraction layer 30 of the organic light-emitting device 10.

[0103] In some embodiments, one of the first electrode 11 and the second electrode 12 is an anode, and the other of the first electrode 11 and the second electrode 12 is a cathode; that is, the second electrode 12 can be an anode or a cathode. Then, the light extraction layer 30 can be located on the side of the anode away from the organic functional layer 20, or the light extraction layer 30 can be located on the side of the cathode away from the organic functional layer 20. In the embodiments of the present application, the case where the first electrode 11 is an anode and the second electrode 12 is a cathode is taken as an example for illustration.

[0104] In the organic light-emitting device 10, the material of the light extraction layer 30 includes the organic compound. Therefore, the material of the light extraction layer 30 has a high glass transition temperature, which can improve the thermal stability of the material.

[0105] In some embodiments, the glass transition temperature T of the organic compound g is greater than or equal to 100 °C. In a preferred embodiment, the glass transition temperature T of the organic compound g is greater than or equal to 120 °C. In a more preferred embodiment, the glass transition temperature T of the organic compound g is greater than or equal to 140 °C. In a still more preferred embodiment, the glass transition temperature T of the organic compound g is greater than or equal to 160 °C. In a most preferred embodiment, the glass transition temperature T of the organic compound g is greater than or equal to 180 °C.

[0106] Since the organic compound has a high refractive index, the light extraction layer 30 also has a high refractive index, which can help improve the light efficiency of the organic light-emitting device 10, especially help improve the external light-emitting efficiency. It is required that the refractive index of the light extraction layer 30 at a wavelength of 630 nm is greater than or equal to 1.7; preferably, the refractive index of the light extraction layer 30 at a wavelength of 630 nm is greater than or equal to 1.78; more preferably, the refractive index of the light extraction layer 30 at a wavelength of 630 nm is greater than or equal to 1.83.

[0107] In some embodiments, the singlet energy (S1) of the material of the light extraction 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.

[0108] In some embodiments, the singlet energy (S1) of the material of the light extraction layer 30 is less than or equal to 3.1 eV; preferably, less than or equal to 3.0 eV.

[0109] The material of the light extraction layer 30 requires a small extinction coefficient. Therefore, 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. The light extraction layer 30 has a high transmittance to visible light, reducing the impact on the light extraction efficiency of the device.

[0110] In other embodiments of the present application, the organic light-emitting device 10 may include at least one of the light-emitting layers 23, and the organic light-emitting layer 10 may include at least one of a hole injection layer 21, a hole transport layer 22, an electron transport layer 24, and an electron injection layer 25.

[0111] In some embodiments, the organic light-emitting device 10 may be selected from an organic light-emitting diode (OLED), an organic light-emitting electrochemical cell (OLEEC), an organic field-effect transistor (OFET), and an organic light-emitting field-effect transistor.

[0112] In some embodiments, the first electrode 11 may be an anode, and the first electrode 11 may comprise a conductive metal or metal oxide, or a conductive polymer. The first electrode 11 can easily inject holes into the hole injection layer 21, or the hole transport layer 22, or the light-emitting layer 23. In some embodiments, the absolute value of the difference between the work function of the first electrode 11 and the HOMO energy level or valence band energy level of the light-emitting body in the light-emitting layer 23 or the p-type semiconductor material serving as the hole injection layer 21, or the hole transport layer 22, or the electron blocking layer is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. Examples of materials for the first electrode 11 include but are not limited to: Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO, aluminum-doped zinc oxide (AZO), etc. Other suitable anode materials are known, and those of ordinary skill in the art can easily select and use them. The material of the first electrode 11 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 certain embodiments, the anode is pattern-structured. Patterned ITO conductive substrates are commercially available and can be used to fabricate the devices according to the present invention.

[0113] In some embodiments, the second electrode 12 may be a cathode, and the second electrode 12 may comprise a conductive metal or metal oxide. The second electrode 12 can easily inject electrons into the electron transport layer 24, or the electron injection layer 25, or directly into the light-emitting layer 23. In some embodiments, the absolute value of the difference between the work function of the second electrode 12 and the LUMO energy level or conduction band energy level of the light-emitting body in the light-emitting layer or the n-type semiconductor material serving as the electron injection layer 25, or the electron transport layer 24, or the 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 that can be used as the cathode of an OLED can potentially be used as the cathode material of the devices in the embodiments of the present application. Examples of materials for the second electrode 12 include but are not limited to: Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloy, BaF 2 / 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.

[0114] In some embodiments, the material of the light extraction layer 30 has a suitable energy level structure. The material of the light extraction layer 30 has strong absorption in the region with a wavelength less than 400 nm, and weak or nearly zero absorption in the visible light region with a wavelength greater than 400 nm, so as to avoid damage to the internal materials of the organic light-emitting device 10 caused by high-energy light irradiation in the subsequent process. At the same time, the light extraction layer 30 has a high refractive index, which can beneficially extract the emission of visible light and improve the light-emitting efficiency of the organic light-emitting device 10. When the reflectivity of the interface between the light extraction layer 30 and the adjacent second electrode 12 is large, the influence of light interference is large. Therefore, the refractive index of the material constituting the light extraction layer 30 is preferably greater than the refractive index of the second electrode 12. The refractive index of the material of the light extraction layer 30 is generally 1.50 or more at 630 nm, more preferably 1.70 or more, and particularly preferably 1.80 or more.

[0115] In some embodiments, the thickness range of the light extraction layer 30 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.

[0116] The organic light-emitting device 10 provided by the embodiments of the present application can also be used in display devices, lighting devices, light sources, sensors, and the like.

[0117] The embodiments of the present application will be described below in conjunction with preferred embodiments. However, the present application is not limited to the following embodiments. It should be understood that the appended claims define the scope of the embodiments of the present application. Under the guidance of the inventive concept of the present application, those skilled in the art should realize that certain changes made to the embodiments of the present application will be covered by the spirit and scope of the present application.

[0118] The synthesis route of organic compound M1 is as follows:

[0119]

[0120] Synthesis of intermediate 1-3:

[0121] Compound 1-1 (10 mmol) and compound 1-2 (10 mmol) were added to a two-necked round-bottom flask, and then a mixed solvent of chloroform and acetic acid (1:1) was added. Then the above system was heated to 60 °C and reacted overnight. After the reaction was complete, the system was cooled to room temperature, and the reaction system was added to a beaker containing methanol and stirred for 1 h. Then, suction filtration was carried out using a Buchner funnel to obtain a crude product. Further, the obtained crude product was stirred overnight with toluene solvent, suction filtered and dried to obtain intermediate 1-3, with a molar amount of 9.45 mmol and a yield of 94.5%, and the mass spectrum m / z [H + = 358.

[0122] Synthesis of organic compound M1:

[0123] Intermediate 1-3 (15 mmol), compound 1-4 (10 mmol), Pd 2 (dba) 3 (0.1mmol), TTBP (tri-tert-butylphosphine, 0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in xylene and stirred at 140°C for 6h under nitrogen atmosphere; after the reaction system was cooled, part of the xylene solvent was removed by rotary evaporation, and dichloromethane and water were used for extraction and separation. The obtained organic phase was dried by rotary evaporation to obtain a crude product. The obtained crude product was stirred with toluene solvent at 100°C overnight, filtered, and dried to obtain an organic compound M1 with a molar weight of 9.12mmol, a yield of 91.2%, and a mass spectrum of m / z [H + ]=681.

[0124] The synthetic route of organic compound M2 is as follows:

[0125]

[0126] Synthesis of organic compound M2:

[0127] Intermediate 1-3 (15 mmol), compound 2-1 (10 mmol), Pd 2 (dba) 3 (0.1mmol), TTBP (tri-tert-butylphosphine, 0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in xylene and stirred at 140°C for 6h under nitrogen atmosphere; after the reaction system was cooled, part of the xylene solvent was removed by rotary evaporation, and dichloromethane and water were used for extraction and separation. The obtained organic phase was dried by rotary evaporation to obtain a crude product. The obtained crude product was stirred with toluene solvent at 100°C overnight, filtered, and dried to obtain an organic compound M2 with a molar weight of 9.25mmol, a yield of 92.5%, and a mass spectrum of m / z [H + ]=713.

[0128] Synthesis of organic compound M3:

[0129]

[0130] Synthesis of intermediate 3-2:

[0131] Compound 1-3 (10 mmol), compound 3-1 (10 mmol) and Pd(PPh 3 ) 4(0.1mmol) was dissolved in a mixed solvent of toluene, ethanol and water, and stirred at 100°C for 6h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, and the separated liquid was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 3-2 with a molar weight of 9.17mmol and a yield of 91.7%. The mass spectrum was m / z [H + ]=390.

[0132] Synthesis of organic compound M3:

[0133] Intermediate 3-2 (10 mmol), compound 1-4 (10 mmol), Pd 2 (dba) 3 The mixture was dissolved in xylene and stirred at 140°C for 6 h under nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation. The organic phase was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain an organic compound M3 with a molar weight of 9.11 mmol and a yield of 91.1%. The mass spectrum was m / z [H + ]=757.

[0134] The synthetic route of organic compound M4 is as follows:

[0135]

[0136] Synthesis of organic compound M4:

[0137] Intermediate 3-2 (10 mmol), compound 2-1 (10 mmol), Pd 2 (dba) 3 The mixture was dissolved in xylene and stirred at 140°C for 6 h under nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation. The organic phase was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain an organic compound M4 with a molar weight of 9.08 mmol and a yield of 90.8%. The mass spectrum was m / z [H + ]=789.

[0138] The synthetic route of organic compound M5 is as follows:

[0139]

[0140] Synthesis of intermediate 5-2:

[0141] Compound 1-3 (10 mmol), compound 5-1 (10 mmol) and Pd(PPh 3 ) 4(0.1mmol) was dissolved in a mixed solvent of toluene, ethanol and water, and stirred at 100°C for 6h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, and the liquid was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 5-2 with a molar weight of 9.45mmol and a yield of 94.5%. The mass spectrum was m / z [H + ]=391.

[0142] Synthesis of organic compound M5:

[0143] Intermediate 5-2 (10 mmol), compound 1-4 (10 mmol), Pd 2 (dba) 3 The mixture was dissolved in xylene and stirred at 140°C for 6 h under nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation. The organic phase was subjected to column chromatography and recrystallization to obtain an organic compound M5 with a molar weight of 9.32 mmol and a yield of 93.2%. The mass spectrum was m / z [H + ]=758.

[0144] The synthetic route of organic compound M6 is as follows:

[0145]

[0146] Synthesis of organic compound M6:

[0147] Intermediate 5-2 (10 mmol), compound 2-1 (10 mmol), Pd 2 (dba) 3 The mixture was dissolved in xylene and stirred at 140°C for 6 h under nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation. The organic phase was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain an organic compound M6 with a molar weight of 9.10 mmol and a yield of 91.0%. The mass spectrum was m / z [H + ]=790.

[0148] The synthetic route of organic compound M7 is as follows:

[0149]

[0150] Synthesis of intermediate 7-2:

[0151] Compound 1-3 (10 mmol), compound 7-1 (10 mmol) and Pd(PPh 3 ) 4(0.1mmol) was dissolved in a mixed solvent of toluene, ethanol and water, and stirred at 100°C for 6h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, and the liquid was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 5-2 with a molar weight of 9.25mmol and a yield of 92.5%. The mass spectrum was m / z [H + ]=392.

[0152] Synthesis of organic compound M7:

[0153] Intermediate 7-2 (10 mmol), compound 1-4 (10 mmol), Pd 2 (dba) 3 The mixture was dissolved in xylene and stirred at 140°C for 6 h under nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation. The organic phase was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain an organic compound M7 with a molar weight of 9.22 mmol and a yield of 92.2%. The mass spectrum was m / z [H + ]=759.

[0154] The synthetic route of organic compound M8 is as follows:

[0155]

[0156] Synthesis of organic compound M8:

[0157] Intermediate 7-2 (10 mmol), compound 2-1 (10 mmol), Pd 2 (dba) 3 The mixture was dissolved in xylene and stirred at 140°C for 6 h under nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation. The organic phase was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain an organic compound M8 with a molar weight of 9.27 mmol and a yield of 92.7%. The mass spectrum was m / z [H + ]=791.

[0158] The synthetic route of organic compound M9 is as follows:

[0159]

[0160] Synthesis of intermediate 9-3:

[0161] Compound 9-1 (10 mmol) and compound 1-2 (10 mmol) were added to a two-necked round-bottom flask, and then a mixed solvent of chloroform and acetic acid (1:1) was added. Then the above system was heated to 60 °C and reacted overnight. After the reaction was complete, the system was cooled to room temperature, and the reaction system was added to a beaker containing methanol and stirred for 1 h. Then, suction filtration was carried out using a Buchner funnel to obtain a crude product. Further, the obtained crude product was stirred overnight with toluene solvent, suction filtered and dried to obtain intermediate 9-2, with a molar amount of 9.55 mmol and a yield of 95.5%, and the mass spectrum m / z [H + = 361.

[0162] Synthesis of organic compound M9:

[0163] Intermediate 9-2 (15 mmol), compound 1-4 (10 mmol), Pd 2 (dba) 3 (0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in xylene and stirred at 140 °C for 6 h under a nitrogen atmosphere; after the reaction system was cooled, part of the xylene solvent was removed by rotary evaporation, and extraction and liquid separation were carried out with dichloromethane and water. The obtained organic phase was dried by rotary evaporation to obtain a crude product. The obtained crude product was stirred overnight with toluene solvent at 100 °C, suction filtered, and dried to obtain organic compound M9, with a molar amount of 9.02 mmol and a yield of 90.2%, and the mass spectrum m / z [H + = 683.

[0164] The synthetic route of organic compound M10 is as follows:

[0165]

[0166] Synthesis of organic compound M10:

[0167] Intermediate 9-2 (15 mmol), compound 2-1 (10 mmol), Pd 2 (dba) 3 (0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in xylene and stirred at 140 °C for 6 h under a nitrogen atmosphere; after the reaction system was cooled, part of the xylene solvent was removed by rotary evaporation, and extraction and liquid separation were carried out with dichloromethane and water. The obtained organic phase was dried by rotary evaporation to obtain a crude product. The obtained crude product was stirred overnight with toluene solvent at 100 °C, suction filtered, and dried to obtain organic compound M10, with a molar amount of 9.31 mmol and a yield of 93.1%, and the mass spectrum m / z [H + = 715.

[0168] The synthetic route of organic compound M11 is as follows:

[0169]

[0170] Synthesis of intermediate 11-2:

[0171] Dissolve compound 1-3 (10 mmol), compound 3-1 (10 mmol) and Pd(PPh 3 ) 4 (0.1 mmol) in a mixed solvent of toluene, ethanol and water, stir at 100 °C for 6 h under a nitrogen atmosphere; after cooling, rotary evaporate to remove the solvent, extract and wash with water and separate the layers, and subject the organic phase to column chromatography and recrystallization to obtain intermediate 11-2 with a molar amount of 9.07 mmol and a yield of 90.7%, and the mass spectrum m / z[H + =392.

[0172] Synthesis of organic compound M11:

[0173] Dissolve intermediate 11-2 (10 mmol), compound 1-4 (10 mmol), Pd 2 (dba) 3 (0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) in xylene, stir at 140 °C for 6 h under a nitrogen atmosphere; after cooling, rotary evaporate to remove the solvent, extract and wash with water and separate the layers, and subject the organic phase to column chromatography and recrystallization to obtain organic compound M11 with a molar amount of 9.19 mmol and a yield of 91.9%, and the mass spectrum m / z[H + =759.

[0174] The synthetic route of organic compound M12 is as follows:

[0175]

[0176] Synthesis of organic compound M12:

[0177] Dissolve intermediate 11-2 (10 mmol), compound 2-1 (10 mmol), Pd 2 (dba) 3 (0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) in xylene, stir at 140 °C for 6 h under a nitrogen atmosphere; after cooling, rotary evaporate to remove the solvent, extract and wash with water and separate the layers, and subject the organic phase to column chromatography and recrystallization to obtain organic compound M12 with a molar amount of 9.09 mmol and a yield of 90.9%, and the mass spectrum m / z[H + =791.

[0178] The synthetic route of organic compound M13 is as follows:

[0179]

[0180] Synthesis of Intermediate 13-2:

[0181] Dissolve Compound 9-2 (10 mmol), Compound 13-1 (10 mmol) and Pd(PPh 3 ) 4 (0.1 mmol) in a mixed solvent of toluene, ethanol and water, stir at 100 °C for 6 h under a nitrogen atmosphere; after cooling, rotary evaporate to remove the solvent, extract and wash with water and separate the layers, and subject the organic phase to column chromatography and recrystallization to obtain Intermediate 13-2, with a molar amount of 9.25 mmol and a yield of 92.5%, and the mass spectrum m / z [H + = 393.

[0182] Synthesis of Organic Compound M13:

[0183] Dissolve Intermediate 13-2 (10 mmol), Compound 1-4 (10 mmol), Pd 2 (dba) 3 (0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) in xylene, stir at 140 °C for 6 h under a nitrogen atmosphere; after cooling, rotary evaporate to remove the solvent, extract and wash with water and separate the layers, and subject the organic phase to column chromatography and recrystallization to obtain Organic Compound M13, with a molar amount of 9.12 mmol and a yield of 91.2%, and the mass spectrum m / z [H + = 760.

[0184] The synthetic route of Organic Compound M14 is as follows:

[0185]

[0186] Synthesis of Organic Compound M14:

[0187] Dissolve Intermediate 13-2 (10 mmol), Compound 2-1 (10 mmol), Pd 2 (dba) 3 (0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) in xylene, stir at 140 °C for 6 h under a nitrogen atmosphere; after cooling, rotary evaporate to remove the solvent, extract and wash with water and separate the layers, and subject the organic phase to column chromatography and recrystallization to obtain Organic Compound M14, with a molar amount of 9.22 mmol and a yield of 92.2%, and the mass spectrum m / z [H + = 792.

[0188] The synthetic route of Organic Compound M15 is as follows:

[0189]

[0190] Synthesis of Intermediate 15-2:

[0191] Dissolve Compound 9-2 (10 mmol), Compound 15-1 (10 mmol) and Pd(PPh 3 ) 4 (0.1 mmol) in a mixed solvent of toluene, ethanol and water, stir at 100 °C for 6 h under a nitrogen atmosphere; after cooling, rotary evaporate to remove the solvent, extract and wash with water and separate the layers, and subject the organic phase to column chromatography and recrystallization to obtain Intermediate 15-2, with a molar amount of 9.12 mmol and a yield of 91.2%, and the mass spectrum m / z [H + = 394.

[0192] Synthesis of Organic Compound M15:

[0193] Dissolve Intermediate 15-2 (10 mmol), Compound 1-4 (10 mmol), Pd 2 (dba) 3 (0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) in xylene, stir at 140 °C for 6 h under a nitrogen atmosphere; after cooling, rotary evaporate to remove the solvent, extract and wash with water and separate the layers, and subject the organic phase to column chromatography and recrystallization to obtain Organic Compound M15, with a molar amount of 9.32 mmol and a yield of 93.2%, and the mass spectrum m / z [H + = 761.

[0194] The synthetic route of Organic Compound M16 is as follows:

[0195]

[0196] Synthesis of Organic Compound M16:

[0197] Dissolve Intermediate 15-2 (10 mmol), Compound 2-1 (10 mmol), Pd 2 (dba) 3 (0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) in xylene, stir at 140 °C for 6 h under a nitrogen atmosphere; after cooling, rotary evaporate to remove the solvent, extract and wash with water and separate the layers, and subject the organic phase to column chromatography and recrystallization to obtain Organic Compound M16, with a molar amount of 9.33 mmol and a yield of 93.3%, and the mass spectrum m / z [H + = 793.

[0198] The synthetic route of Organic Compound M17 is as follows:

[0199]

[0200] Synthesis of intermediate 17-2:

[0201] Compound 1-3 (10 mmol), compound 17-1 (20 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. After the system was cooled to room temperature, a portion of the solvent was removed by rotary evaporation using a rotary evaporator, and then extracted with dichloromethane and water for 3 times. After separation, the organic phase was dried to obtain a crude product. The crude product was purified by column chromatography and recrystallized to obtain intermediate 7-2, with a molar weight of 9.16 mmol and a yield of 91.6%. Mass spectrum m / z [H + ]=406.

[0202] Synthesis of intermediate 17-4:

[0203] Compound 17-2 (10 mmol), compound 17-3 (10 mmol) and Pd(PPh 3 ) 4 (0.1mmol) was dissolved in a mixed solvent of toluene, ethanol and water, and stirred at 100°C for 6h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, and the liquid was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 17-4 with a molar weight of 8.91mmol and a yield of 89.1%. The mass spectrum was m / z [H + ]=437.

[0204] Synthesis of organic compound M17:

[0205] Intermediate 17-4 (10 mmol), compound 1-4 (10 mmol), Pd 2 (dba) 3 The mixture was dissolved in xylene and stirred at 140°C for 6 h under nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation. The organic phase was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain organic compound M17 with a molar weight of 9.21 mmol and a yield of 92.1%. The mass spectrum was m / z [H + ]=775.

[0206] The synthetic route of organic compound M18 is as follows:

[0207]

[0208] Synthesis of organic compound M18:

[0209] Intermediate 17-4 (10 mmol), compound 2-1 (10 mmol), Pd2 (dba) 3 (0.1 mmol), TTBP (tri - tert - butylphosphine, 0.2 mmol) and sodium tert - butoxide (30 mmol) were dissolved in xylene, and stirred at 140 °C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, extracted and washed with water for liquid separation. The organic phase was purified by column chromatography and recrystallized to obtain organic compound M18, with a molar amount of 9.32 mmol and a yield of 93.2%. Mass spectrometry m / z [H + = 791.

[0210] The synthetic route of organic compound M19 is as follows:

[0211]

[0212] Synthesis of intermediate 19 - 2:

[0213] Compound 9 - 2 (10 mmol), compound 19 - 1 (20 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. After the reaction system was cooled to room temperature, a part of the solvent was removed by rotary evaporation using a rotary evaporator, and then extracted 3 times with dichloromethane and water. After liquid separation, the organic phase was dried by rotary evaporation to obtain a crude product. The crude product was purified by column chromatography separation method and recrystallized to obtain intermediate 19 - 2, with a molar amount of 9.08 mmol and a yield of 90.8%. Mass spectrometry m / z [H + = 408.

[0214] Synthesis of intermediate 19 - 3:

[0215] Compound 19 - 2 (10 mmol), compound 17 - 3 (10 mmol) and Pd(PPh 3 ) 4 (0.1 mmol) was dissolved in a mixed solvent of toluene, ethanol and water, and stirred at 100 °C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, extracted and washed with water for liquid separation. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 19 - 3, with a molar amount of 8.82 mmol and a yield of 88.2%. Mass spectrometry m / z [H + = 439.

[0216] Synthesis of organic compound M19:

[0217] Intermediate 19 - 3 (10 mmol), compound 1 - 4 (10 mmol), Pd 2 (dba) 3(0.1 mmol), TTBP (tri - tert - butylphosphine, 0.2 mmol) and sodium tert - butoxide (30 mmol) were dissolved in xylene and stirred at 140 °C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, extracted and washed with water for liquid - liquid separation, and the organic phase was purified by column chromatography and recrystallized to obtain organic compound M19, with a molar amount of 9.21 mmol and a yield of 92.1%, and the mass spectrometry m / z [H + = 761.

[0218] The synthetic route of organic compound M20 is as follows:

[0219]

[0220] Synthesis of organic compound M20:

[0221] Intermediate 19 - 3 (10 mmol), compound 2 - 1 (10 mmol), Pd 2 (dba) 3 (0.1 mmol), TTBP (tri - tert - butylphosphine, 0.2 mmol) and sodium tert - butoxide (30 mmol) were dissolved in xylene and stirred at 140 °C for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, extracted and washed with water for liquid - liquid separation, and the organic phase was purified by column chromatography and recrystallized to obtain organic compound M20, with a molar amount of 9.21 mmol and a yield of 91.1%, and the mass spectrometry m / z [H + = 793.

[0222] The synthetic route of organic compound M21 is as follows:

[0223]

[0224] Synthesis of intermediate 21 - 3:

[0225] Compound 21 - 1 (10 mmol) and compound 21 - 2 (10 mmol) were added to a two - necked round - bottom flask, and then a mixed solvent of chloroform and acetic acid (1:1) was added. Then the above system was heated to 60 °C and reacted overnight. After the reaction was complete, the system was cooled to room temperature, and the reaction mixture was added to a beaker containing methanol and stirred for 1 h. Then, it was filtered by Buchner funnel to obtain the crude product. Further, the obtained crude product was stirred with toluene solvent overnight and filtered and dried to obtain intermediate 21 - 3, with a molar amount of 9.16 mmol and a yield of 91.6%, and the mass spectrometry m / z [H + = 373.

[0226] Synthesis of organic compound M21:

[0227] Intermediate 21 - 3 (15 mmol), compound 21 - 4 (10 mmol), Pd 2 (dba)3 (0.1 mmol), TTBP (tri - tert - butylphosphine, 0.2 mmol) and sodium tert - butoxide (30 mmol) were dissolved in xylene and stirred at 140 °C for 6 h under a nitrogen atmosphere; after the reaction system was cooled, part of the xylene solvent was removed by rotary evaporation, and the mixture was extracted and separated with dichloromethane and water. The obtained organic phase was dried by rotary evaporation to obtain a crude product. The obtained crude product was stirred overnight in toluene solvent at 100 °C, filtered by suction, and dried to obtain organic compound M21, with a molar amount of 9.05 mmol and a yield of 90.5%, and the mass spectrum m / z [H + = 695.

[0228] The synthetic route of organic compound M22 is as follows:

[0229]

[0230] Synthesis of intermediate 22 - 3:

[0231] Compound 22 - 1 (10 mmol) and compound 22 - 2 (10 mmol) were added to a two - necked round - bottom flask, and then a mixed solvent of chloroform and acetic acid (1:1) was added. Then the above system was heated to 60 °C and reacted overnight. After the reaction was complete, the system was cooled to room temperature, and the reaction system was added to a beaker containing methanol and stirred for 1 h. Then, it was filtered by suction with a Buchner funnel to obtain a crude product. Further, the obtained crude product was stirred overnight in toluene solvent, filtered by suction, and dried to obtain intermediate 22 - 3, with a molar amount of 9.25 mmol and a yield of 92.5%, and the mass spectrum m / z [H + = 358.

[0232] Synthesis of intermediate 22 - 6:

[0233] Intermediate 22 - 4 (15 mmol), compound 22 - 5 (10 mmol), Pd 2 (dba) 3 (0.1 mmol), TTBP (tri - tert - butylphosphine, 0.2 mmol) and sodium tert - butoxide (30 mmol) were dissolved in toluene and stirred at 120 °C for 5 h under a nitrogen atmosphere; after the reaction system was cooled, part of the toluene solvent was removed by rotary evaporation, and the mixture was extracted and separated with dichloromethane and water. The obtained organic phase was dried by rotary evaporation to obtain a crude product. The obtained crude product was stirred overnight in toluene solvent, filtered by suction, and dried to obtain intermediate 22 - 6, with a molar amount of 9.45 mmol and a yield of 94.5%, and the mass spectrum m / z [H + = 503.

[0234] Synthesis of organic compound M22:

[0235] Intermediate 22-3 (15 mmol), compound 22-6 (10 mmol), Pd 2 (dba) 3 (0.1mmol), TTBP (tri-tert-butylphosphine, 0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in xylene and stirred at 140°C for 6h under nitrogen atmosphere; after the reaction system was cooled, part of the xylene solvent was removed by rotary evaporation, and dichloromethane and water were used for extraction and separation. The obtained organic phase was dried by rotary evaporation to obtain a crude product. The obtained crude product was stirred with toluene solvent at 100°C overnight, filtered, and dried to obtain an organic compound M22 with a molar weight of 9.05mmol, a yield of 90.5%, and a mass spectrum of m / z [H + ]=781.

[0236] The synthetic route of organic compound M23 is as follows:

[0237]

[0238] Synthesis of intermediate 23-3:

[0239] Compound 23-1 (10 mmol) and compound 23-2 (10 mmol) were added to a double-necked round-bottom flask, followed by a mixed solvent of chloroform and acetic acid (1:1). The system was then heated to 60°C and reacted overnight. After the reaction was complete, the system was cooled to room temperature, and the reacted system was added to a beaker containing methanol and stirred for 1 h. Then, the crude product was filtered with a Buchner funnel to obtain a crude product. Further, the obtained crude product was stirred with toluene solvent overnight, filtered and dried to obtain intermediate 23-3, with a molar weight of 9.15 mmol, a yield of 91.5%, and a mass spectrum of m / z [H + ]=358.

[0240] Synthesis of intermediate 23-6:

[0241] Intermediate 23-4 (15 mmol), compound 23-5 (10 mmol), Pd 2 (dba) 3 (0.1mmol), TTBP (tri-tert-butylphosphine, 0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene and stirred at 120°C for 5h under nitrogen atmosphere; after the reaction system was cooled, part of the toluene solvent was removed by rotary evaporation, and dichloromethane and water were used for extraction and separation. The obtained organic phase was dried by rotary evaporation to obtain a crude product. The obtained crude product was stirred with toluene solvent overnight, filtered, and dried to obtain intermediate 23-6, with a molar weight of 9.23mmol, a yield of 92.3%, and a mass spectrum of m / z [H + ]=502.

[0242] Synthesis of organic compound M23:

[0243] Intermediate 23-3 (15 mmol), compound 23-6 (10 mmol), Pd 2 (dba) 3 (0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in xylene, and stirred at 140 °C for 6 h under a nitrogen atmosphere; after the reaction system was cooled, part of the xylene solvent was removed by rotary evaporation, and the mixture was extracted and separated with dichloromethane and water. The obtained organic phase was dried by rotary evaporation to obtain a crude product. The obtained crude product was stirred overnight with toluene solvent at 100 °C, filtered by suction, and dried to obtain organic compound M23, with a molar amount of 9.25 mmol and a yield of 92.5%, and the mass spectrometry m / z [H + = 730.

[0244] The synthetic route of organic compound M24 is as follows:

[0245]

[0246] Synthesis of intermediate 24-3:

[0247] Compound 24-1 (10 mmol) and compound 24-2 (10 mmol) were added to a two-necked round-bottom flask, and then a mixed solvent of chloroform and acetic acid (1:1) was added. Then the above system was heated to 60 °C and reacted overnight. After the reaction was complete, the system was cooled to room temperature, and the reaction system was added to a beaker containing methanol and stirred for 1 h. Then, it was filtered by suction with a Buchner funnel to obtain a crude product. Further, the obtained crude product was stirred overnight with toluene solvent, filtered by suction and dried to obtain intermediate 24-3, with a molar amount of 9.41 mmol and a yield of 94.1%, and the mass spectrometry m / z [H + = 358.

[0248] Synthesis of intermediate 24-6:

[0249] Intermediate 24-4 (15 mmol), compound 24-5 (10 mmol), Pd 2 (dba) 3 (0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene, and stirred at 120 °C for 5 h under a nitrogen atmosphere; after the reaction system was cooled, part of the toluene solvent was removed by rotary evaporation, and the mixture was extracted and separated with dichloromethane and water. The obtained organic phase was dried by rotary evaporation to obtain a crude product. The obtained crude product was stirred overnight with toluene solvent, filtered by suction, and dried to obtain intermediate 24-6, with a molar amount of 9.15 mmol and a yield of 91.5%, and the mass spectrometry m / z [H + = 577.

[0250] Synthesis of organic compound M24:

[0251] Intermediate 24-3 (15 mmol), compound 24-6 (10 mmol), Pd 2 (dba) 3 (0.1mmol), TTBP (tri-tert-butylphosphine, 0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in xylene and stirred at 140°C for 6h under nitrogen atmosphere; after the reaction system was cooled, part of the xylene solvent was removed by rotary evaporation, and dichloromethane and water were used for extraction and separation. The obtained organic phase was dried by rotary evaporation to obtain a crude product. The obtained crude product was stirred with toluene solvent at 100°C overnight, filtered, and dried to obtain an organic compound M24 with a molar weight of 8.95mmol, a yield of 89.5%, and a mass spectrum of m / z [H + ]=805.

[0252] The synthetic route of organic compound M25 is as follows:

[0253]

[0254] Synthesis of intermediate 25-3:

[0255] Compound 25-1 (10 mmol) and compound 25-2 (10 mmol) were added to a double-necked round-bottom flask, followed by a mixed solvent of chloroform and acetic acid (1:1). The system was then heated to 60°C and reacted overnight. After the reaction was complete, the system was cooled to room temperature, and the reacted system was added to a beaker containing methanol and stirred for 1 h. Then, the crude product was filtered with a Buchner funnel to obtain a crude product. Further, the obtained crude product was stirred with toluene solvent overnight, filtered and dried to obtain intermediate 25-3, with a molar weight of 9.21 mmol, a yield of 92.1%, and a mass spectrum of m / z [H + ]=435.

[0256] Synthesis of organic compound M25:

[0257] Intermediate 25-3 (15 mmol), compound 25-4 (10 mmol), Pd 2 (dba) 3 (0.1mmol), TTBP (tri-tert-butylphosphine, 0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in xylene and stirred at 140°C for 6h under nitrogen atmosphere; after the reaction system was cooled, part of the xylene solvent was removed by rotary evaporation, and dichloromethane and water were used for extraction and separation. The obtained organic phase was dried by rotary evaporation to obtain a crude product. The obtained crude product was stirred with toluene solvent at 100°C overnight, filtered, and dried to obtain an organic compound M25 with a molar weight of 9.21mmol, a yield of 92.1%, and a mass spectrum of m / z [H+ = 757.

[0258] Energy Structure of Organic Compounds

[0259] The energy levels of organic materials can be obtained by quantum calculation. For example, using TD-DFT (Time-Dependent Density Functional Theory) through Gaussian09W (Gaussian Inc.). The specific simulation method can be referred to WO2011141110. First, use the semi-empirical method "Ground State / DFT / Default Spin / B3LYP / 6-31G(d)" (Charge 0 / Spin Singlet) to optimize the molecular geometry. The energy structure of the organic molecule is calculated by the TD-DFT (Time-Dependent Density Functional Theory) method "TD-SCF / DFT / Default Spin / B3PW91" and the basis set "6-31G(d)" (Charge 0 / Spin Singlet).

[0260] The compound is evaporated onto single-crystalline silicon by vacuum evaporation to form a 50-nm thin film. The single-crystalline silicon is placed on the sample stage of an ellipsometer (ES-01) with an incident angle of 70°. The test is carried out in an atmospheric environment. The extinction coefficient (k) and refractive index (n) test results of the compound are obtained by the ellipsometer. The results are shown in Table 1:

[0261] Table 1

[0262]

[0263]

[0264] According to the data in Table 1, it can be seen that the organic compound provided in the embodiment of the present application has weak absorption in the visible light band, while showing high absorption performance in the ultraviolet band. This enables the organic compound to effectively resist the damage caused by external high-energy light to the inside of the device. Compared with the control example Ref-01, the organic compound provided in the embodiment of the present application has a higher refractive index, and this characteristic ensures a better light extraction effect, thereby optimizing the overall performance of the device.

[0265] Among them, the control example Ref-01 can be seen in the subsequent embodiments.

[0266] Preparation and Characterization of Organic Light-Emitting Devices

[0267] The following will specifically describe the preparation process of the above-mentioned organic light-emitting device 10 through specific embodiments. The structure of the OLED device is: ITO / Ag / ITO (anode) / HATCN / SFNFB / m-CP:Ir(p-ppy 3 / NaTzF 2 / LiF / Mg:Ag / Light extraction layer, the preparation steps are as follows:

[0268] Clean the ITO conductive glass anode layer, and then ultrasonically clean it with deionized water, acetone, and isopropyl alcohol for 15 minutes, and then treat it in a plasma cleaner for 5 minutes to improve the electrode work function to obtain the first electrode 11. On the first electrode 11, deposit the hole injection layer material HATCN by vacuum evaporation, with a thickness of 5 nm, and the evaporation rate On the hole injection layer 21, deposit the hole transport material SFNFB by vacuum evaporation, with a thickness of 80 nm. Deposit the light-emitting layer 23 on the hole transport layer 22, with m-CP as the host material and Ir(p-ppy) 3 as the doping material, and the mass ratio of Ir(p-ppy) 3 to m-CP is 1:9, with a thickness of 30 nm. On the light-emitting layer 23, deposit the electron transport material NaTzF 2 , with a thickness of 30 nm. On the electron transport layer 24, deposit the electron injection layer LiF by vacuum evaporation, with a thickness of 1 nm, and this layer is the electron injection layer 25. On the electron injection layer 25, deposit Mg:Ag by vacuum evaporation to obtain the second electrode 12, with a Mg:Ag doping ratio of 9:1 and a thickness of 15 nm. On the second electrode 12, deposit the organic compound M1 by vacuum evaporation to obtain the light extraction layer 30, with a thickness of 60 nm.

[0269] Device Example 2: The organic compound in the light extraction layer 30 of the organic light-emitting device 10 becomes M2.

[0270] Device Example 3: The organic compound in the light extraction layer 30 of the organic light-emitting device 10 becomes M3.

[0271] Device Example 4: The organic compound in the light extraction layer 30 of the organic light-emitting device 10 becomes M4.

[0272] Device Example 5: The organic compound in the light extraction layer 30 of the organic light-emitting device 10 becomes M5.

[0273] Device Example 6: The organic compound in the light extraction layer 30 of the organic light-emitting device 10 becomes M6.

[0274] Device Example 7: The organic compound in the light extraction layer 30 of the organic light-emitting device 10 becomes M7.

[0275] Device Example 8: The organic compound in the light extraction layer 30 of the organic light-emitting device 10 becomes M8.

[0276] Device Example 9: The organic compound in the light extraction layer 30 of the organic light-emitting device 10 becomes M9.

[0277] Device Example 10: The organic compound in the light extraction layer 30 of the organic light-emitting device 10 becomes M10.

[0278] Device Example 11: The organic compound in the light extraction layer 30 of the organic light-emitting device 10 becomes M11.

[0279] Device Example 12: The organic compound in the light extraction layer 30 of the organic light-emitting device 10 becomes M12.

[0280] Device Example 13: The organic compound in the light extraction layer 30 of the organic light-emitting device 10 becomes M13

[0281] Device Example 14: The organic compound in the light extraction layer 30 of the organic light-emitting device 10 becomes M14.

[0282] Device Example 15: The organic compound in the light extraction layer 30 of the organic light-emitting device 10 becomes M15.

[0283] Device Example 16: The organic compound in the light extraction layer 30 of the organic light-emitting device 10 becomes M16.

[0284] Device Example 17: The organic compound in the light extraction layer 30 of the organic light-emitting device 10 becomes M17.

[0285] Device Example 18: The organic compound in the light extraction layer 30 of the organic light-emitting device 10 becomes M18.

[0286] Device Example 19: The organic compound in the light extraction layer 30 of the organic light-emitting device 10 becomes M19.

[0287] Device Example 20: The organic compound in the light extraction layer 30 of the organic light-emitting device 10 becomes M20.

[0288] Device Example 21: The organic compound in the light extraction layer 30 of the organic light-emitting device 10 becomes M21.

[0289] Device Example 22: The organic compound in the light extraction layer 30 of the organic light-emitting device 10 becomes M22.

[0290] Device Example 23: The organic compound in the light extraction layer 30 of the organic light-emitting device 10 becomes M23.

[0291] Device Example 24: The organic compound in the light extraction layer 30 of the organic light-emitting device 10 becomes M24.

[0292] Device Example 25: The organic compound in the light extraction layer 30 of the organic light-emitting device 10 becomes M25.

[0293] Device Comparative Example 1: The organic compound in the light extraction layer 30 of the organic light-emitting device 10 becomes Ref-01.

[0294] The chemical structures of the compounds involved in the device are as follows:

[0295]

[0296] Table 2

[0297]

[0298]

[0299] The luminous efficiency in Table 2 is the data obtained when the current density is 10 mA / cm 2 at this time. It can be seen from Table 2 that compared with Device Comparative Example 1, when the organic compound provided in the embodiments of the present application is used as the material of the light extraction layer 30, the luminous efficiency of the organic light-emitting device 10 can be effectively improved.

[0300] In addition, the embodiments of the present application also provide a display panel, and the display panel includes the organic light-emitting device described in the above embodiments.

[0301] It can be understood that since the display panel has the same organic light-emitting device as in the above embodiments, therefore, the display panel has the same effects as the organic light-emitting device, which will not be elaborated here.

[0302] In the description of the present application, the terms "first" and "second" are only used for descriptive purposes, and cannot be understood as indicating or implying relative importance or implicitly specifying the quantity of the indicated technical features. Thus, the features defined with "first" and "second" may explicitly or implicitly include one or more features. In the description of the present application, "a plurality" means two or more, unless otherwise specifically defined.

[0303] In the above embodiments, the descriptions of the respective embodiments have their own emphases. For the parts not detailed in a certain embodiment, reference may be made to the relevant descriptions of other embodiments.

[0304] Among the embodiments, embodiments, and related technical features of the present application, they can be combined and replaced with each other without conflict.

[0305] The above are only the preferred embodiments of the present application, and do not impose any formal restrictions on the present application. However, any simple modifications, equivalent changes, and decorations made to the above embodiments based on the technical essence of the present application without departing from the content of the technical solution of the present application still fall within the scope of the technical solution of the present application.

Claims

1. An organic compound, characterized in that The organic compound has a structure as shown in formula (1): Wherein, X1 and X2 are selected from N or CH; Y is selected from O or S; L1, L2 and L3 are each independently selected from a single bond, a substituted or unsubstituted aromatic group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroaryl group having 4 to 20 carbon atoms; R is selected from H, methyl or phenyl, and m is selected from any integer from 0 to 3; Ar1 is selected from a substituted or unsubstituted aryl group having 6 to 20 carbon atoms and a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

2. The organic compound according to claim 1, characterized in that X1 is selected from N, and X2 is selected from N or CH.

3. The organic compound according to claim 1, characterized in that L1, L2 and L3 are each independently selected from a single bond, a phenyl group, a biphenyl group, a naphthyl group, a pyridyl group, a pyrimidyl group, a pyrazinyl group, a dibenzofuranyl group or a phenyl-substituted carbazolyl group.

4. The organic compound according to claim 1, characterized in that Ar1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted furanyl, substituted or unsubstituted naphthofuranophenyl, substituted or unsubstituted thienyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted N- phenylene; -phenylcarbazolyl, substituted or unsubstituted N-diphenylcarbazolyl, substituted or unsubstituted N-naphthylcarbazolyl, substituted or unsubstituted N-dibenzofuranylcarbazolyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinazoline, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted cinnolinyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazoline, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted naphthofuranyl, substituted or unsubstituted naphthothiophenyl.

5. The organic compound according to claim 4, characterized in that Ar1 is selected from phenyl, benzoxazolyl or benzothiazolyl.

6. The organic compound according to any one of claims 1 to 5, characterized in that The structure of the organic compound is shown in formula (2-1) or formula (2-2):

7. The organic compound according to any one of claims 1 to 5, characterized in that The structure of the organic compound is shown in formula (3-1) or formula (3-2):

8. 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 7.

9. An organic light-emitting device, characterized in that: The organic light emitting device comprises: a first electrode; An organic functional layer, disposed on one side of the first electrode; A second electrode is disposed on a side of the organic functional layer away from the first electrode; The light extraction layer is arranged on the side of the second electrode away from the organic functional layer. The material of the light extraction layer includes at least one organic compound as described in any one of claims 1 to 7, or the light extraction layer is made of the composition as described in claim 8.

10. A display panel, characterized in that: The display panel includes the organic light emitting device as claimed in claim 9.

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