Organic compound, organic electronic device, and display panel

Abstract

The invention relates to an organic compound, an organic electronic device and a display panel, the structural general formula of the organic compound is as shown in the formula (1): # imgabs0 #. The organic compound provided by the invention can be used as a light extraction layer material to effectively improve the light extraction efficiency of the device, and the organic compound also can maintain good thermal stability; therefore, the long service life of the device can be realized.

Description

Technical Field

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

[0002] The organic light-emitting diode (OLED) technology, also known as organic electroluminescence technology, is an advanced self-luminous display technology. OLEDs generate 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. OLED technology is renowned for its advantages such as self-luminance, high brightness, high efficiency, high contrast ratio, and fast response time.

[0003] In recent years, the luminous efficiency of OLED devices has been significantly improved, and its internal quantum efficiency has approached the theoretical limit. Therefore, enhancing the light extraction efficiency has become the key to further improving 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 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 to enhance 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 using 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] For the above reasons, researchers have begun to explore organic compounds with high refractive indices in order to improve the light extraction efficiency in electroluminescent devices. An ideal organic compound should meet the following conditions: having a high extinction coefficient in the ultraviolet band (less than 400 nanometers) to protect 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 thermal stability. 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

[0005] Embodiments of this application provide an organic compound, an organic electronic device, and a display panel. The organic compound can effectively improve the light output efficiency of the device as a light extraction layer material, and the organic compound can also maintain good thermal stability, thereby contributing to the device achieving a good service life.

[0006] To achieve the above object, according to the first aspect of the present application, an organic compound is provided. The general structural formula of the organic compound is shown in Formula (1):

[0007]

[0008] Wherein, Ar1 and Ar2 are selected from any one or a combination of more than one of a hydrogen atom, a deuterium atom, a straight-chain alkyl group having 1 to 20 C atoms, an alkoxy group having 1 to 20 C atoms, a thioalkoxy group having 1 to 20 C atoms, a branched or cyclic alkyl group having 3 to 20 C atoms, an alkoxy group having 3 to 20 C atoms, a thioalkoxy group having 3 to 20 C atoms, a silyl group, a keto group having 1 to 20 C atoms, an alkoxycarbonyl group having 2 to 20 C atoms, an aryloxycarbonyl group having 7 to 20 C atoms, a cyano group, a carbamoyl group, a halocarbonyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, CF3, Cl, Br, F, a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, an aryloxy group having 5 to 60 ring atoms, and a heteroaryloxy group having 5 to 60 ring atoms.

[0009] According to the second aspect of the present application, an organic electronic device is provided. The organic electronic device includes:

[0010] A first electrode;

[0011] An organic functional layer disposed on one side of the first electrode;

[0012] A second electrode disposed on the side of the organic functional layer away from the first electrode;

[0013] A light extraction layer disposed on the side of the second electrode away from the first electrode;

[0014] Wherein, the material of the light extraction layer includes at least one of the above-mentioned organic compounds.

[0015] According to the third aspect of the present application, a display panel is further provided. The display panel includes the above-mentioned organic electronic device.

[0016] In the organic compound, organic electronic device, and display panel according to the embodiments of the present application, the organic compound represented by formula (1) is a compound containing a poly(p - xylylene) group. This organic compound has a high extinction coefficient in the ultraviolet band, a relatively small extinction coefficient in the visible light range, a high refractive index, and a high glass transition temperature. It can be used as a light extraction layer material for organic electronic devices, which can not only avoid damage to the internal materials of the organic electronic device by external high - energy light but also maintain good thermal stability and effectively improve the light extraction efficiency of the organic electronic device. Therefore, when the organic compound is used as a light extraction layer material in the light extraction layer of an organic electronic device, it can improve the light output efficiency of the organic electronic device and extend the service life of the organic electronic device.

[0017] Other features and advantages of the present application will be described in detail in the following specific embodiments section. BRIEF DESCRIPTION OF THE DRAWINGS

[0018] In order to more clearly illustrate the technical solutions in the embodiments of the present application, the following briefly introduces the drawings required for the description of the embodiments. Obviously, the drawings in the following description are only some embodiments of the present application. For those skilled in the art, without creative efforts, other drawings can be obtained based on these drawings.

[0019] In order to more completely understand the present application and its beneficial effects, the following description will be made in conjunction with the drawings, where the same reference numerals in the following description represent the same parts.

[0020] Figure 1 is a schematic structural diagram of an organic electronic device provided by an embodiment of the present application.

[0021] Description of the reference numerals: 1, substrate; 2, first electrode (anode); 3, organic functional layer; 3a, hole injection layer; 3b, hole transport layer; 3c, light - emitting layer; 3d, electron transport layer; 3e, electron injection layer; 4, second electrode (cathode); 5, light extraction layer. DETAILED DESCRIPTION OF THE EMBODIMENTS

[0022] The following will clearly and completely describe the technical solutions in the embodiments of the present application in conjunction with the drawings in the embodiments of the present application.

[0023] The present application provides an organic compound containing a poly(p - xylylene) group and its application in organic electronic devices, especially its application as a light extraction layer material for organic electroluminescent devices. To make the purpose, technical solutions, and effects of the present application clearer and more definite, the present application is further described in detail below. It should be understood that the specific embodiments described herein are only used to explain the present application and are not used to limit the present application.

[0024] In the present application, "substituted" means that a hydrogen atom in a substituent is replaced by a substituent group.

[0025] In the present application, "the number of ring atoms" means the number of atoms among the atoms constituting the ring itself of a structural compound obtained by bonding atoms in a ring (for example, a monocyclic compound, a fused-ring compound, a crosslinked compound, a carbocyclic compound, a heterocyclic compound). When the ring is substituted by a substituent group, the atoms contained in the substituent group are not included in the ring-forming atoms. The same applies to "the number of ring atoms" described below unless otherwise specified. For example, the number of ring atoms of a benzene ring is 6, the number of ring atoms of a naphthalene ring is 10, and the number of ring atoms of a thiophenyl group is 5.

[0026] In the present application, "adjacent groups" means that these groups are bonded to the same carbon atom or adjacent carbon atoms. These definitions apply correspondingly to "adjacent substituents".

[0027] In the present application, an aromatic group means a hydrocarbon group containing at least one aromatic ring. A heteroaromatic group means an aromatic hydrocarbon group containing at least one heteroatom. The heteroatom is preferably selected from Si, N, P, O, S, and / or Ge, and particularly preferably selected from Si, N, P, O, and / or S. A fused-ring aromatic group means that the ring of the aromatic group can have two or more rings, where two carbon atoms are shared by two adjacent rings, that is, a fused ring. A fused heteroaromatic group means a fused-ring aromatic hydrocarbon group containing at least one heteroatom. For the purposes of the present application, an aromatic group or a heteroaromatic group includes not only the system of aromatic rings but also non-aromatic ring systems. Therefore, systems such as pyridine, thiophene, pyrrole, pyrazole, triazole, imidazole, oxazole, oxadiazole, thiazole, tetrazole, pyrazine, pyridazine, pyrimidine, triazine, carbene, etc. are also considered aromatic groups or heteroaromatic groups for the purposes of this application. For the purposes of the present application, a fused-ring aromatic or fused heteroaromatic ring system includes not only the system of aromatic groups or heteroaromatic groups, but also, in which multiple aromatic groups or heteroaromatic groups can be interrupted by short non-aromatic units (<10% of non-H atoms, preferably less than 5% of non-H atoms, such as C, N, or O atoms). Therefore, systems such as 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamine, diaryl ether, etc. are also considered fused-ring aromatic ring systems for the purposes of this application.

[0028] Examples of the present application provide an organic compound, and the general structural formula of the organic compound is shown in Formula (1):

[0029]

[0030] Among them, Ar1 and Ar2 are selected from any one or more combinations of a hydrogen (H) atom, a deuterium (D) atom, a linear alkyl group having 1 to 20 C atoms, an alkoxy group having 1 to 20 C atoms, a thioalkoxy group having 1 to 20 C atoms, a branched or cyclic alkyl group having 3 to 20 C atoms, an alkoxy group having 3 to 20 C atoms, a thioalkoxy group having 3 to 20 C atoms, a silyl group, a keto group having 1 to 20 C atoms, an alkoxycarbonyl group having 2 to 20 C atoms, an aryloxycarbonyl group having 7 to 20 C atoms, a cyano group (-CN), a carbamoyl group (-C(=O)NH2), a halocarbonyl group, a formyl group (-C(=O)-H), an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, CF3, Cl, Br, F, a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, an aryloxy group having 5 to 60 ring atoms, and a heteroaryloxy group having 5 to 60 ring atoms.

[0031] In some embodiments, Ar1 and Ar2 are selected from any one or more combinations of the following groups:

[0032]

[0033] Among them, the dashed line represents the connection bond between two groups. For example, the dashed line represents the bond connecting Ar1 and Ar2 to the parent parylene group, and the connection site of the connection bond represented by the dashed line can have multiple choices within the selectable range;

[0034] R2 to R5 are selected from any one or more combinations of a hydrogen atom, a deuterium atom, a linear alkyl group having 1 to 20 C atoms, an alkoxy group having 1 to 20 C atoms, a thioalkoxy group having 1 to 20 C atoms, a branched or cyclic alkyl group having 3 to 20 C atoms, an alkoxy group having 3 to 20 C atoms, a thioalkoxy group having 3 to 20 C atoms, a silyl group, a keto group having 1 to 20 C atoms, an alkoxycarbonyl group having 2 to 20 C atoms, an aryloxycarbonyl group having 7 to 20 C atoms, a cyano group, a carbamoyl group, a halocarbonyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, CF3, Cl, Br, F, a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, an aryloxy group having 5 to 60 ring atoms, and a heteroaryloxy group having 5 to 60 ring atoms; among R2 to R5, two or more adjacent groups do not form a ring or form an aliphatic, aromatic or heteroaromatic ring system having a single ring or multiple rings.

[0035] The hydrogen atoms on the cyclic Ar1 and Ar2 groups listed above can be further substituted by R7, and each occurrence of R7 is independently selected from a deuterium atom, a straight-chain alkyl group having 1 to 20 C atoms, an alkoxy group having 1 to 20 C atoms, a thioalkoxy group having 1 to 20 C atoms, a branched or cyclic alkyl group having 3 to 20 C atoms, an alkoxy group having 3 to 20 C atoms, a thioalkoxy group having 3 to 20 C atoms, a silyl group, a keto group having 1 to 20 C atoms, an alkoxycarbonyl group having 2 to 20 C atoms, an aryloxycarbonyl group having 7 to 20 C atoms, a cyano group, a carbamoyl group, a halocarbonyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, CF3, Cl, Br, F, a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, an aryloxy group having 5 to 60 ring atoms, a heteroaryloxy group having 5 to 60 ring atoms, or any one or more combinations thereof; two or more adjacent R7 groups do not form a ring or form an aliphatic, aromatic or heteroaromatic ring system having a single ring or multiple rings.

[0036] In some embodiments, Ar1 and Ar2 are selected from any one or more combinations of the following groups:

[0037]

[0038]

[0039] In some embodiments, Ar1 and Ar2 are selected from any one or more combinations of the following groups:

[0040]

[0041] In some embodiments, Ar1 and Ar2 are selected from any one or more combinations of the following groups:

[0042]

[0043] In a preferred embodiment, Ar1 and Ar2 are selected from any one or more combinations of the following groups:

[0044]

[0045] In some embodiments, R2 to R5 are selected from a single bond or one or more combinations of the following groups:

[0046]

[0047] Wherein, W is selected from N or CR8;

[0048] X1 is selected from O, S, NR9, CR 10 R 11 ;

[0049] R8 to R 11 are each independently selected from a hydrogen atom, a deuterium atom, a linear alkyl group having 1 to 20 C atoms, an alkoxy group having 1 to 20 C atoms, a thioalkoxy group having 1 to 20 C atoms, a branched or cyclic alkyl group having 3 to 20 C atoms, an alkoxy group having 3 to 20 C atoms, a thioalkoxy group having 3 to 20 C atoms, a silyl group, a keto group having 1 to 20 C atoms, an alkoxycarbonyl group having 2 to 20 C atoms, an aryloxycarbonyl group having 7 to 20 C atoms, a cyano group, a carbamoyl group, a halocarbonyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, CF3, Cl, Br, F, a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, an aryloxy group having 5 to 60 ring atoms, a heteroaryloxy group having 5 to 60 ring atoms, or any combination of one or more thereof; among R8 to R 11 two or more adjacent groups do not form a ring or form an aliphatic, aromatic or heteroaromatic ring system having a monocyclic or polycyclic structure.

[0050] In a preferred embodiment, R2 to R5 are each independently selected from a hydrogen atom, CF3, or a phenyl group substituted with at least one CF3.

[0051] In some embodiments, the organic compound is selected from any one of the compounds represented by Formulae 2-1 to 2-12:

[0052]

[0053]

[0054]

[0055] In other embodiments, the organic compound is selected from any one of the compounds represented by Formulae 3-1 to 3-12:

[0056]

[0057]

[0058] In some preferred embodiments, the organic compound is selected from any one of the compounds represented by Formulae 3-1 to 3-8.

[0059] In some embodiments, R2 is selected from a hydrogen atom, CF3, or a phenyl group substituted with at least one CF3.

[0060] In a preferred embodiment, R2 is selected from a hydrogen atom, CF3 or * indicates the attachment site.

[0061] In some embodiments, the organic compound includes any one of the following compounds:

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081] Examples of the organic compound represented by the general formula (1) of the embodiments of the present application are listed above, but are not limited thereto. Moreover, H in the structural formulas listed above can be further arbitrarily substituted, especially deuterated, and deuteration can improve the service life of the device to a certain extent.

[0082] In some embodiments, the above-mentioned organic compound provided by the embodiments of the present application has a relatively high glass transition temperature, which is beneficial to improving its thermal stability. In some embodiments, the glass transition temperature Tg of the organic compound is greater than or equal to 100 °C; in some preferred embodiments, Tg is greater than or equal to 120 °C; in a more preferred embodiment, Tg is greater than or equal to 140 °C; in a more preferred embodiment, Tg is greater than or equal to 160 °C; in a most preferred embodiment, Tg is greater than or equal to 180 °C.

[0083] In some embodiments, the refractive index of the organic compound for light with a wavelength of 630 nanometers is greater than 1.7. In some preferred embodiments, the refractive index of the organic compound for light with a wavelength of 630 nanometers is greater than 1.78. In some more preferred embodiments, the refractive index of the organic compound for light with a wavelength of 630 nanometers is greater than 1.83. Therefore, the organic compound has a high refractive index in the visible light range.

[0084] In some embodiments, the energy of the first excited singlet state (S1) of the organic compound is greater than 2.7 eV. In some preferred embodiments, the energy of the first excited singlet state (S1) of the organic compound is greater than 2.8 eV. In some more preferred embodiments, the energy of the first excited singlet state (S1) of the organic compound is greater than 2.85 eV.

[0085] In some embodiments, the organic compound has a small extinction coefficient. For example, the extinction coefficient of the organic compound for light with a wavelength of 430 nanometers is less than 0.1. In a preferred embodiment, the extinction coefficient of the organic compound for light with a wavelength of 430 nanometers is less than 0.003. In some more preferred embodiments, the extinction coefficient of the organic compound for light with a wavelength of 430 nanometers is less than 0.001. Therefore, the organic compound has a high transmittance for visible light, which can reduce the impact on the light output efficiency of the device.

[0086] In some embodiments, the organic compound has a large extinction coefficient in the wavelength range less than or equal to 400 nm. In some embodiments, the extinction coefficient of the organic compound for light with a wavelength of 350 nm is greater than or equal to 0.3. In some preferred embodiments, the extinction coefficient of the organic compound for light with a wavelength of 350 nm is greater than or equal to 0.5. In some more preferred embodiments, the extinction coefficient of the organic compound for light with a wavelength of 350 nm is greater than or equal to 0.7. In some more preferred embodiments, the extinction coefficient of the organic compound for light with a wavelength of 350 nm is greater than or equal to 1.0. Therefore, the organic compound has a high extinction coefficient in the ultraviolet band, which can protect the device material from the influence of harmful light.

[0087] One object of the embodiments of the present application is to provide a material solution for vapor deposition type OLEDs, that is, the organic compound can be applied to vapor deposition type OLEDs. Correspondingly, in some embodiments, the molecular weight of the organic compound is less than or equal to 1200 g / mol; in some preferred embodiments, the molecular weight of the organic compound is less than or equal to 1100 g / mol; in some more preferred embodiments, the molecular weight of the organic compound is less than or equal to 1000 g / mol; in some even more preferred embodiments, the molecular weight of the organic compound is less than or equal to 950 g / mol; in some most preferred embodiments, the molecular weight of the organic compound is less than or equal to 900 g / mol.

[0088] Another object of the present application is to provide a material solution for printing type OLEDs, that is, the organic compound can be applied to printing type OLEDs. Correspondingly, in some embodiments, the molecular weight of the organic compound is greater than or equal to 800 g / mol; in some preferred embodiments, the molecular weight of the organic compound is greater than or equal to 900 g / mol; in some more preferred embodiments, the molecular weight of the organic compound is greater than or equal to 1000 g / mol; in some even more preferred embodiments, the molecular weight of the organic compound is greater than or equal to 1100 g / mol; in some most preferred embodiments, the molecular weight of the organic compound is greater than or equal to 1200 g / mol.

[0089] In some embodiments, at 25 °C, the solubility of the organic compound in toluene is greater than or equal to 2 mg / ml; in some preferred embodiments, at 25 °C, the solubility of the organic compound in toluene is greater than or equal to 3 mg / ml; in some more preferred embodiments, at 25 °C, the solubility of the organic compound in toluene is greater than or equal to 4 mg / ml; in some most preferred embodiments, at 25 °C, the solubility of the organic compound in toluene is greater than or equal to 5 mg / ml.

[0090] The embodiments of the present application also provide a composition, which comprises at least one organic compound as described above and at least one organic solvent. The organic solvent is selected from aromatic, heteroaromatic, esters, aromatic ketones or aromatic ethers, aliphatic ketones or aliphatic ethers, cycloaliphatic or olefinic compounds, borate or phosphate compounds, and mixtures of two or more solvents.

[0091] In some embodiments, the organic solvent is selected from aromatic or heteroaromatic based solvents, especially aliphatic chain / ring substituted aromatic solvents, aromatic ketone solvents or aromatic ether solvents.

[0092] Examples of organic solvents suitable for this application include, but are 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-(phenyloxirane)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, 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, 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.

[0093] Further, when the composition is an ink material applied in a printing process, the organic solvent can be selected from: aliphatic ketones, such as 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2,5-hexanedione, 2,6,8-trimethyl-4-nonanone, phorone, di-n-pentyl ketone, etc.; or aliphatic ethers, such as pentyl ether, hexyl ether, dioctyl ether, ethylene glycol dibutyl ether, diethylene glycol diethyl ether, diethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, triethylene glycol ethyl methyl ether, triethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, etc.

[0094] In some other embodiments, when the composition is an ink material applied in a printing process, the composition further comprises another organic solvent. Examples of the another organic solvent include (but are not limited to): 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.

[0095] In some embodiments, the composition is a solution. In some other embodiments, the composition is a suspension.

[0096] In some embodiments, the composition may include 0.01 wt% to 20 wt% of the organic compound. In a preferred embodiment, the content range of the organic compound in the composition is 0.1 wt% to 15 wt%. In a more preferred embodiment, the content range of the organic compound in the composition is 0.2 wt% to 10 wt%. In a most preferred embodiment, the content range of the organic compound in the composition is 0.25 wt% to 5 wt%.

[0097] For example, the mass fraction of the organic compound in the composition is 0.01%, 0.05%, 0.1%, 0.15%, 0.2%, 0.25%, 0.3%, 0.35%, 0.4%, 0.45%, 0.5%, 0.6%, 0.7%, 0.8%, 0.9%, 1%, 3%, 5%, 8%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 19% or 20%.

[0098] The composition provided by the present application can be used as a coating or printing ink for preparing organic electronic devices. Particularly preferably, the composition can be used as a coating or printing ink to prepare organic electronic devices by a preparation method of printing or coating.

[0099] Among them, suitable printing or coating techniques include (but are not limited to) inkjet printing, nozzle printing, relief printing, screen printing, dip coating, spin coating, blade coating, roller printing, reverse roller printing, lithography, flexography, rotary printing, spraying, brush coating or pad printing, slot die coating, etc. Gravure printing, nozzle printing and inkjet printing are preferred. The solution or suspension can 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 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.

[0100] The organic compound or the composition provided by the embodiments of the present application can be applied to organic electronic devices.

[0101] The embodiments of the present application also provide an organic electronic device. The material of the organic electronic device includes an organic compound represented by the general formula (1). The organic electronic device includes but is not limited to organic light-emitting diodes (OLEDs), organic photovoltaic cells (OPVs), organic light-emitting electrochemical cells (OLEECs), organic field-effect transistors (OFETs), organic light-emitting field-effect transistors (OLEFETs), organic lasers, organic spintronic devices, organic sensors, and organic plasmon emitting diodes (OPEDs), etc. Particularly preferably, the organic electronic device is an organic electroluminescent device, for example, the organic electronic device is an OLED.

[0102] In some embodiments, the organic compound can be used as a material for the electron transport layer, the host material of the light-emitting layer, or the light extraction layer of an organic electronic device.

[0103] In a preferred embodiment, the organic compound is a material for the light extraction layer of an organic electronic device.

[0104] As Figure 1 shown, the organic electronic device provided by the embodiment of the present application includes a substrate 1, a first electrode 2, an organic functional layer 3, a second electrode 4, and a light extraction layer 5. The first electrode 2 is disposed on one side of the substrate 1, and the organic functional layer 3 is disposed on the side of the first electrode 2 away from the substrate 1; the second electrode 4 is disposed on the side of the organic functional layer 3 away from the first electrode 2; the light extraction layer 5 is disposed on the side of the second electrode 4 away from the first electrode 2; wherein, the material of the light extraction layer 5 includes at least one organic compound represented by the general formula (1).

[0105] In some embodiments, the material of the light extraction layer 5 is selected from at least one of the compounds represented by Formula 2-1 to Formula 2-12.

[0106] In other embodiments, the material of the light extraction layer 5 is selected from at least one of the compounds represented by Formula 3-1 to Formula 3-12.

[0107] In a preferred embodiment, the material of the light extraction layer 5 is selected from at least one of the compounds represented by Formula 3-1 to Formula 3-8.

[0108] In some embodiments, the first electrode 2 is an anode, and the second electrode 4 is a cathode, that is, the light extraction layer 5 is located on the side of the cathode away from the organic functional layer 3.

[0109] Of course, in other embodiments, depending on the structure and light extraction mode of the device, the light extraction layer may also be located on the side of the anode away from the organic functional layer, and the present application does not limit this.

[0110] In some embodiments, the organic functional layer includes at least one of an electron injection layer, an electron transport layer, a hole injection layer, a hole transport layer, and a light-emitting layer, and the organic functional layer includes at least one of the light-emitting layers.

[0111] In a preferred embodiment, the organic electronic device is an OLED device. As Figure 1 shown, the organic functional layer 3 includes a hole injection layer 3a, a hole transport layer 3b, a light-emitting layer 3c, an electron transport layer 3d, and an electron injection layer 3e that are sequentially stacked on the side of the first electrode 2 away from the substrate 1.

[0112] In some embodiments, the light extraction layer 5 has a high glass transition temperature, which is beneficial to improving its thermal stability. In some embodiments, the glass transition temperature Tg of the organic compound is greater than or equal to 100 °C; in some preferred embodiments, Tg is greater than or equal to 120 °C; in a more preferred embodiment, Tg is greater than or equal to 140 °C; in a still more preferred embodiment, Tg is greater than or equal to 160 °C; in a most preferred embodiment, Tg is greater than or equal to 180 °C.

[0113] Specifically, the light extraction layer 5 has a high refractive index, which is beneficial to improving the light extraction efficiency of the organic electronic device, especially contributing to the improvement of the external light emission efficiency of the device. In some embodiments, the refractive index of the light extraction layer 5 for light with a wavelength of 630 nm is greater than 1.7. In some preferred embodiments, the refractive index of the light extraction layer 5 for light with a wavelength of 630 nm is greater than 1.78. In some more preferred embodiments, the refractive index of the light extraction layer 5 for light with a wavelength of 630 nm is greater than 1.83.

[0114] In some embodiments, the first excited singlet state energy (S1) of the light extraction layer 5 is greater than 2.7 eV. In some preferred embodiments, the first excited singlet state energy (S1) of the light extraction layer 5 is greater than 2.8 eV. In some more preferred embodiments, the first excited singlet state energy (S1) of the light extraction layer 5 is greater than 2.85 eV.

[0115] In some other embodiments, the singlet state energy (S1) of the light extraction layer 5 is less than or equal to 3.1 eV. Preferably, the singlet state energy (S1) of the light extraction layer 5 is less than or equal to 3.0 eV.

[0116] In some embodiments, the light extraction layer 5 has a small extinction coefficient. For example, the extinction coefficient of the light extraction layer 5 for light with a wavelength of 430 nm is less than 0.1. In a preferred embodiment, the extinction coefficient of the light extraction layer 5 for light with a wavelength of 430 nm is less than 0.003. In some more preferred embodiments, the extinction coefficient of the light extraction layer 5 for light with a wavelength of 430 nm is less than 0.001. Therefore, the light extraction layer 5 has a high transmittance for visible light, which can reduce the influence on the light extraction efficiency of the device.

[0117] In some embodiments, the organic electronic device is selected from an organic light-emitting diode (OLED), an organic light-emitting electrochemical cell (OLEEC), an organic field-effect transistor (OFET), an organic light-emitting field-effect transistor (OLEFET), but is not limited thereto.

[0118] The cathode, anode and light extraction layer of the organic electronic device will be specifically described below, but are not limited thereto.

[0119] The anode may comprise a conductive metal or metal oxide, or a conductive polymer. The anode can easily inject holes into the hole injection layer (HIL), or hole transport layer (HTL), or the light-emitting layer. In one embodiment, the absolute value of the difference between the work function of the anode and the HOMO level or valence band level of the light emitter in the light-emitting layer or a 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. Examples of anode materials include, but are not limited to: Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO, aluminum-doped zinc oxide (AZO), etc. Other suitable anode materials are known, and those of ordinary skill in the art can easily select and use them. The anode material can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), etc. In some embodiments, the anode is pattern-structured. Patterned ITO conductive substrates are commercially available and can be used to fabricate the organic electronic devices according to the present application.

[0120]

[0121] The cathode may comprise a conductive metal or metal oxide. The cathode can easily inject electrons into the electron injection layer (EIL), or electron transport layer (ETL), or directly into the light-emitting layer. In one embodiment, the absolute value of the difference between the work function of the cathode and the LUMO level or conduction band level of the light emitter in the light-emitting layer or an n-type semiconductor material serving as the electron injection layer (EIL), electron transport layer (ETL), or hole blocking layer (HBL) is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. In principle, all materials that can be used as the cathode of an OLED can potentially be used as the cathode material of the devices of the present application. Examples of cathode materials include, but are not limited to: Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloy, BaF2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO, etc. The cathode material can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), etc.The light extraction layer has a suitable energy level structure, has strong absorption in the wavelength band less than 400 nm, and has weak absorption or is close to zero in the visible light band with a wavelength greater than 400 nm, which can effectively avoid damage to the internal materials of the device caused by high-energy light irradiation in the subsequent process. At the same time, the light extraction layer has a high refractive index and can beneficially export the emission of visible light, which can effectively improve the light emission efficiency of the organic electronic device. And when the reflectivity of the interface between the light extraction layer and the adjacent electrode is large, the influence of the light interference effect is large. Therefore, the refractive index of the light extraction layer material is preferably greater than that of the adjacent electrode. The refractive index of the light extraction layer material is generally greater than 1.50 at the 630 nm light wave, more preferably greater than 1.70, and particularly preferably greater than 1.80.

[0122] In some embodiments, the thickness range of the light extraction layer 5 is from 10 nanometers to 200 nanometers. In a preferred embodiment, the thickness range of the light extraction layer 5 is from 20 nm to 150 nm. In a more preferred embodiment, the thickness range of the light extraction layer 5 is from 30 nm to 100 nm. In a still more preferred embodiment, the thickness range of the light extraction layer 5 is from 40 nm to 90 nm.

[0123] The organic electronic device provided by the embodiments of the present application can be applied to electronic devices, and the electronic devices include but are not limited to display devices, lighting devices, light sources, sensors, etc.

[0124] The embodiments of the present application also provide a display panel, and the display panel includes the above-mentioned organic electronic device.

[0125] The present application will be described below in conjunction with preferred embodiments, but the protection scope of the present application is not limited to the following embodiments. It should be understood that the appended claims define the protection 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 embodiments of the present application will be covered by the spirit and scope of the claims of the present application. Specific Embodiments

[0127] The organic compounds and their preparation methods of the present application will be further described in detail below in conjunction with specific embodiments. The raw materials used in the following embodiments are all commercially available products unless otherwise specified.

[0128] (1) Synthesis Examples of Organic Compounds

[0129] Example 1

[0130] The synthesis route of organic compound M1 is as follows:

[0131]

[0132] Synthesis of Organic Compound M1:

[0133] Dissolve Compound 1-1 (10 mmol) and Compound 1-2 (20 mmol) in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and add Pd(PPh3)4 (0.1) and potassium carbonate (30 mmol); under a nitrogen atmosphere, heat the reaction solution to 100 °C and stir for 6 hours (h); after the reaction solution cools, rotary evaporate to remove most of the solvent, then extract and wash with water and separate the layers, and subject the organic phase to column chromatography and recrystallization to obtain Organic Compound M1. The molar amount of Organic Compound M1 is 7.84 mmol, the yield of Organic Compound M1 is 78.4%, and the MS (ASAP) of Organic Compound M1 = 360.

[0134] Example 2

[0135] The synthesis route of Organic Compound M2 is as follows:

[0136]

[0137] Synthesis of Organic Compound M2:

[0138] Dissolve Compound 1-1 (10 mmol) and Compound 2-1 (20 mmol) in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and add Pd(PPh3)4 (0.1) and potassium carbonate (30 mmol); under a nitrogen atmosphere, heat the reaction solution to 100 °C and stir for 6 h; after the reaction solution cools, rotary evaporate to remove most of the solvent, then extract and wash with water and separate the layers, and subject the organic phase to column chromatography and recrystallization to obtain Organic Compound M2. The molar amount of Organic Compound M2 is 7.36 mmol, the yield of Organic Compound M2 is 73.6%, and the MS (ASAP) of Organic Compound M2 = 632.

[0139] Example 3

[0140] The synthesis route of Organic Compound M3 is as follows:

[0141]

[0142] Synthesis of Intermediate 3-2:

[0143] Dissolve compound 3-1 (10 mmol) and compound 2-1 (20 mmol) in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and add Pd(PPh3)4 (0.1) and potassium carbonate (30 mmol); under a nitrogen atmosphere, heat the reaction solution to 100 °C and stir for 6 h; after the reaction solution cools, rotary evaporate to remove most of the solvent, then extract and wash with water and separate the layers. The organic phase is purified by column chromatography and recrystallized to obtain intermediate 3-2. The molar amount of intermediate 3-2 is 8.31 mmol, the yield of intermediate 3-2 is 83.1%, and the MS (ASAP) of intermediate 3-2 = 539.

[0144] Synthesis of intermediate 3-3:

[0145] Dissolve compound 1-1 (10 mmol) and bis(pinacolato)diboron (40 mmol) in toluene (40 ml), and add Pd(OAc)2 (0.1) and potassium acetate (60 mmol); under a nitrogen atmosphere, heat the reaction solution to 100 °C and stir for 6 h; after the reaction solution cools, rotary evaporate to remove most of the solvent, then extract and wash with water and separate the layers. The organic phase is purified by column chromatography and recrystallized to obtain intermediate 3-3. The molar amount of intermediate 3-3 is 9.03 mmol, the yield of intermediate 3-3 is 90.3%, and the MS (ASAP) of intermediate 3-3 = 460.

[0146] Synthesis of organic compound M3:

[0147] Dissolve intermediate 3-3 (10 mmol) and intermediate 3-2 (20 mmol) in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and add Pd(PPh3)4 (0.1) and potassium carbonate (30 mmol); under a nitrogen atmosphere, heat the reaction solution to 100 °C and stir for 6 h; after the reaction solution cools, rotary evaporate to remove most of the solvent, then extract and wash with water and separate the layers. The organic phase is purified by column chromatography and recrystallized to obtain organic compound M3. The molar amount of organic compound M3 is 8.64 mmol, the yield of organic compound M3 is 86.4%, and the MS (ASAP) of organic compound M3 = 1214.

[0148] Example 4

[0149] The synthetic route of organic compound M4 is as follows:

[0150]

[0151] Synthesis of intermediate 4-2:

[0152] Dissolve compound 4-1 (10 mmol) and compound 2-1 (10 mmol) in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and add Pd(PPh3)4 (0.1) and potassium carbonate (30 mmol); under a nitrogen atmosphere, heat the reaction solution to 100 °C and stir for 6 h; after the reaction solution cools, rotary evaporate to remove most of the solvent, then extract and wash with water and separate the liquid. The organic phase is subjected to column chromatography and recrystallization to obtain intermediate 4-2. The molar amount of intermediate 4-2 is 8.79 mmol, the yield of intermediate 4-2 is 87.9%, and the MS(ASAP) of intermediate 4-2 = 374.

[0153] Synthesis of organic compound M4:

[0154] Dissolve intermediate 3-3 (10 mmol) and intermediate 4-2 (20 mmol) in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and add Pd(PPh3)4 (0.1) and potassium carbonate (30 mmol); under a nitrogen atmosphere, heat the reaction solution to 100 °C and stir for 6 h; after the reaction solution cools, rotary evaporate to remove most of the solvent, then extract and wash with water and separate the liquid. The organic phase is subjected to column chromatography and recrystallization to obtain organic compound M4. The molar amount of organic compound M4 is 8.96 mmol, the yield of organic compound M4 is 89.6%, and the MS(ASAP) of organic compound M4 = 884.

[0155] Example 5

[0156] The synthetic route of organic compound M5 is as follows:

[0157]

[0158] Synthesis of intermediate 5-2:

[0159] Dissolve compound 5-1 (10 mmol) and compound 2-1 (10 mmol) in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and add Pd(PPh3)4 (0.1) and potassium carbonate (30 mmol); under a nitrogen atmosphere, heat the reaction solution to 100 °C and stir for 6 h; after the reaction solution cools, rotary evaporate to remove most of the solvent, then extract and wash with water and separate the liquid. The organic phase is subjected to column chromatography and recrystallization to obtain intermediate 5-2. The molar amount of intermediate 5-2 is 8.13 mmol, the yield of intermediate 5-2 is 81.3%, and the MS(ASAP) of intermediate 5-2 = 324.

[0160] Synthesis of organic compound M5:

[0161] Intermediate 3-3 (10 mmol) and intermediate 5-2 (20 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1) and potassium carbonate (30 mmol) were added. Under a nitrogen atmosphere, the reaction solution was heated to 100 °C and stirred for 6 h. After the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then extraction and washing with water were carried out for liquid separation. The organic phase was subjected to column chromatography and recrystallization to obtain organic compound M5. The molar amount of organic compound M5 was 6.78 mmol, the yield of organic compound M5 was 67.8%, and the MS (ASAP) of organic compound M5 was 784.

[0162] Example 6

[0163] The synthetic route of organic compound M6 is as follows:

[0164]

[0165] Synthesis of intermediate 6-2:

[0166] Compound 6-1 (10 mmol) and compound 2-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1) and potassium carbonate (30 mmol) were added; under a nitrogen atmosphere, the reaction solution was heated to 100 °C and stirred for 6 h; after the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then extraction and washing with water were carried out for liquid separation. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 6-2. The molar amount of intermediate 6-2 was 7.34 mmol, the yield of intermediate 6-2 was 73.4%, and the MS (ASAP) of intermediate 6-2 was 324.

[0167] Synthesis of organic compound M6:

[0168] Intermediate 3-3 (10 mmol) and intermediate 6-2 (20 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1) and potassium carbonate (30 mmol) were added; under a nitrogen atmosphere, the reaction solution was heated to 100 °C and stirred for 6 h; after the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then extraction and washing with water were carried out for liquid separation. The organic phase was subjected to column chromatography and recrystallization to obtain organic compound M6. The molar amount of organic compound M6 was 6.15 mmol, the yield of organic compound M6 was 61.5%, and the MS (ASAP) of organic compound M6 was 784.

[0169] Example 7

[0170] The synthetic route of organic compound M7 is as follows:

[0171]

[0172] Synthesis of Intermediate 7-2:

[0173] Dissolve Compound 7-1 (10 mmol) and Compound 2-1 (10 mmol) in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and add Pd(PPh3)4 (0.1) and potassium carbonate (30 mmol); under a nitrogen atmosphere, heat the reaction solution to 100 °C and stir for 6 h; after the reaction solution cools, rotary evaporate to remove most of the solvent, then extract and wash with water and separate the layers. The organic phase is purified by column chromatography and recrystallized to obtain Intermediate 7-2. The molar amount of Intermediate 7-2 is 7.57 mmol, the yield of Intermediate 7-2 is 75.7%, and the MS (ASAP) of Intermediate 7-2 = 324.

[0174] Synthesis of Organic Compound M7:

[0175] Dissolve Intermediate 3-3 (10 mmol) and Intermediate 7-2 (20 mmol) in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and add Pd(PPh3)4 (0.1) and potassium carbonate (30 mmol); under a nitrogen atmosphere, heat the reaction solution to 100 °C and stir for 6 h; after the reaction solution cools, rotary evaporate to remove most of the solvent, then extract and wash with water and separate the layers. The organic phase is purified by column chromatography and recrystallized to obtain Organic Compound M7. The molar amount of Organic Compound M7 is 6.85 mmol, the yield of Organic Compound M7 is 68.5%, and the MS (ASAP) of Organic Compound M7 = 784.

[0176] Example 8

[0177] The synthetic route of Organic Compound M8 is as follows:

[0178]

[0179] Synthesis of Intermediate 8-2:

[0180] Dissolve Intermediate 5-2 (10 mmol) and Compound 8-1 (10 mmol) in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and add Pd(PPh3)4 (0.1) and potassium carbonate (30 mmol); under a nitrogen atmosphere, heat the reaction solution to 100 °C and stir for 6 h; after the reaction solution cools, rotary evaporate to remove most of the solvent, then extract and wash with water and separate the layers. The organic phase is purified by column chromatography and recrystallized to obtain Intermediate 8-2. The molar amount of Intermediate 8-2 is 8.56 mmol, the yield of Intermediate 8-2 is 85.6%, and the MS (ASAP) of Intermediate 8-2 = 400.

[0181] Synthesis of Organic Compound M8:

[0182] Dissolve intermediate 3-3 (10 mmol) and intermediate 8-2 (20 mmol) in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and add Pd(PPh3)4 (0.1) and potassium carbonate (30 mmol); under a nitrogen atmosphere, heat the reaction solution to 100 °C and stir for 6 h; after the reaction solution cools, rotary evaporate to remove most of the solvent, then extract and wash with water and separate the layers, and subject the organic phase to column chromatography and recrystallization to obtain organic compound M8. The molar amount of organic compound M8 is 7.56 mmol, the yield of organic compound M8 is 75.6%, and the MS (ASAP) of organic compound M8 = 936.

[0183] Example 9

[0184] The synthetic route of organic compound M9 is as follows:

[0185]

[0186] Synthesis of intermediate 9-2:

[0187] Dissolve intermediate 5-2 (10 mmol) and compound 9-1 (10 mmol) in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and add Pd(PPh3)4 (0.1) and potassium carbonate (30 mmol); under a nitrogen atmosphere, heat the reaction solution to 100 °C and stir for 6 h; after the reaction solution cools, rotary evaporate to remove most of the solvent, then extract and wash with water and separate the layers, and subject the organic phase to column chromatography and recrystallization to obtain intermediate 9-2. The molar amount of intermediate 9-2 is 8.24 mmol, the yield of intermediate 9-2 is 82.4%, and the MS (ASAP) of intermediate 9-2 = 400.

[0188] Synthesis of organic compound M9:

[0189] Dissolve intermediate 3-3 (10 mmol) and intermediate 9-2 (20 mmol) in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and add Pd(PPh3)4 (0.1) and potassium carbonate (30 mmol); under a nitrogen atmosphere, heat the reaction solution to 100 °C and stir for 6 h; after the reaction solution cools, rotary evaporate to remove most of the solvent, then extract and wash with water and separate the layers, and subject the organic phase to column chromatography and recrystallization to obtain organic compound M9. The molar amount of organic compound M9 is 5.69 mmol, the yield of organic compound M9 is 56.9%, and the MS (ASAP) of organic compound M9 = 936.

[0190] Example 10

[0191] The synthetic route of organic compound M10 is as follows:

[0192]

[0193] Synthesis of Intermediate 10-2:

[0194] Dissolve Intermediate 5-2 (10 mmol) and Compound 10-1 (10 mmol) in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and add Pd(PPh3)4 (0.1) and potassium carbonate (30 mmol); under a nitrogen atmosphere, heat the reaction solution to 100 °C and stir for 6 h; after the reaction solution cools, rotary evaporate to remove most of the solvent, then extract and wash with water and separate the layers. The organic phase is subjected to column chromatography and recrystallization to obtain Intermediate 9-2. The molar amount of Intermediate 9-2 is 7.38 mmol, the yield of Intermediate 9-2 is 73.8%, and the MS (ASAP) of Intermediate 9-2 = 400.

[0195] Synthesis of Organic Compound M10:

[0196] Dissolve Intermediate 3-3 (10 mmol) and Intermediate 10-2 (20 mmol) in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and add Pd(PPh3)4 (0.1) and potassium carbonate (30 mmol); under a nitrogen atmosphere, heat the reaction solution to 100 °C and stir for 6 h; after the reaction solution cools, rotary evaporate to remove most of the solvent, then extract and wash with water and separate the layers. The organic phase is subjected to column chromatography and recrystallization to obtain Organic Compound M10. The molar amount of Organic Compound M10 is 5.22 mmol, the yield of Organic Compound M10 is 52.2%, and the MS (ASAP) of Organic Compound M10 = 936.

[0197] Example 11

[0198] The synthetic route of Organic Compound M11 is as follows:

[0199]

[0200] Synthesis of Intermediate 11-1:

[0201] Dissolve Intermediate 6-2 (10 mmol) and Compound 8-1 (10 mmol) in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and add Pd(PPh3)4 (0.1) and potassium carbonate (30 mmol); under a nitrogen atmosphere, heat the reaction solution to 100 °C and stir for 6 h; after the reaction solution cools, rotary evaporate to remove most of the solvent, then extract and wash with water and separate the layers. The organic phase is subjected to column chromatography and recrystallization to obtain Intermediate 11-1. The molar amount of Intermediate 11-1 is 7.03 mmol, the yield of Intermediate 11-1 is 70.3%, and the MS (ASAP) of Intermediate 11-1 = 400.

[0202] Synthesis of Organic Compound M11:

[0203] Dissolve intermediate 3-3 (10 mmol) and intermediate 11-1 (20 mmol) in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and add Pd(PPh3)4 (0.1) and potassium carbonate (30 mmol). Under a nitrogen atmosphere, heat the reaction solution to 100 °C and stir for 6 h. After the reaction solution cools, rotary evaporate to remove most of the solvent, then extract, wash, and separate the layers. The organic phase is subjected to column chromatography and recrystallization to obtain organic compound M11. The molar amount of organic compound M11 is 6.06 mmol, the yield of organic compound M11 is 60.6%, and the MS (ASAP) of organic compound M11 = 936.

[0204] Example 12

[0205] The synthesis route of organic compound M12 is as follows:

[0206]

[0207] Synthesis of intermediate 12-1:

[0208] Dissolve intermediate 6-2 (10 mmol) and compound 9-1 (10 mmol) in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and add Pd(PPh3)4 (0.1) and potassium carbonate (30 mmol). Under a nitrogen atmosphere, heat the reaction solution to 100 °C and stir for 6 h. After the reaction solution cools, rotary evaporate to remove most of the solvent, then extract, wash, and separate the layers. The organic phase is subjected to column chromatography and recrystallization to obtain intermediate 12-1. The molar amount of intermediate 12-1 is 7.49 mmol, the yield of intermediate 12-1 is 74.9%, and the MS (ASAP) of intermediate 12-1 = 400.

[0209] Synthesis of organic compound M12:

[0210] Dissolve intermediate 3-3 (10 mmol) and intermediate 12-1 (20 mmol) in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and add Pd(PPh3)4 (0.1) and potassium carbonate (30 mmol). Under a nitrogen atmosphere, heat the reaction solution to 100 °C and stir for 6 h. After the reaction solution cools, rotary evaporate to remove most of the solvent, then extract, wash, and separate the layers. The organic phase is subjected to column chromatography and recrystallization to obtain organic compound M12. The molar amount of organic compound M12 is 6.37 mmol, the yield of organic compound M12 is 63.7%, and the MS (ASAP) of organic compound M12 = 936.

[0211] Example 13

[0212] The synthetic route of organic compound M13 is as follows:

[0213]

[0214] Synthesis of intermediate 13-1:

[0215] Dissolve intermediate 6-2 (10 mmol) and compound 10-1 (10 mmol) in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and add Pd(PPh3)4 (0.1) and potassium carbonate (30 mmol); under a nitrogen atmosphere, heat the reaction solution to 100 °C and stir for 6 h; after the reaction solution cools, rotary evaporate to remove most of the solvent, then extract and wash with water and separate the layers. The organic phase is subjected to column chromatography and recrystallization to obtain intermediate 13-1. The molar amount of intermediate 13-1 is 7.15 mmol, the yield of intermediate 13-1 is 71.5%, and the MS (ASAP) of intermediate 13-1 = 400.

[0216] Synthesis of organic compound M13:

[0217] Dissolve intermediate 3-3 (10 mmol) and intermediate 13-1 (20 mmol) in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and add Pd(PPh3)4 (0.1) and potassium carbonate (30 mmol); under a nitrogen atmosphere, heat the reaction solution to 100 °C and stir for 6 h; after the reaction solution cools, rotary evaporate to remove most of the solvent, then extract and wash with water and separate the layers. The organic phase is subjected to column chromatography and recrystallization to obtain organic compound M13. The molar amount of organic compound M13 is 5.06 mmol, the yield of organic compound M13 is 50.6%, and the MS (ASAP) of organic compound M13 = 936.

[0218] Example 14

[0219] The synthetic route of organic compound M14 is as follows:

[0220]

[0221] Synthesis of intermediate 14-1:

[0222] Dissolve intermediate 7-2 (10 mmol) and compound 8-1 (10 mmol) in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and add Pd(PPh3)4 (0.1) and potassium carbonate (30 mmol); under a nitrogen atmosphere, heat the reaction solution to 100 °C and stir for 6 h; after the reaction solution cools, rotary evaporate to remove most of the solvent, then extract and wash with water and separate the liquid. The organic phase is subjected to column chromatography and recrystallization to obtain intermediate 14-1. The molar amount of intermediate 14-1 is 7.17 mmol, the yield of intermediate 14-1 is 71.7%, and the MS(ASAP) of intermediate 14-1 = 400.

[0223] Synthesis of organic compound M14:

[0224] Dissolve intermediate 3-3 (10 mmol) and intermediate 14-1 (20 mmol) in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and add Pd(PPh3)4 (0.1) and potassium carbonate (30 mmol). Under a nitrogen atmosphere, heat the reaction solution to 100 °C and stir for 6 h. After the reaction solution cools, rotary evaporate to remove most of the solvent, then extract and wash with water and separate the liquid. The organic phase is subjected to column chromatography and recrystallization to obtain organic compound M14. The molar amount of organic compound M14 is 6.38 mmol, the yield of organic compound M14 is 63.8%, and the MS(ASAP) of organic compound M14 = 936.

[0225] Example 15

[0226] The synthesis route of organic compound M15 is as follows:

[0227]

[0228] Synthesis of intermediate 15-1:

[0229] Dissolve intermediate 7-2 (10 mmol) and compound 9-1 (10 mmol) in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and add Pd(PPh3)4 (0.1) and potassium carbonate (30 mmol); under a nitrogen atmosphere, heat the reaction solution to 100 °C and stir for 6 h; after the reaction solution cools, rotary evaporate to remove most of the solvent, then extract and wash with water and separate the liquid. The organic phase is subjected to column chromatography and recrystallization to obtain intermediate 15-1. The molar amount of intermediate 15-1 is 8.46 mmol, the yield of intermediate 15-1 is 84.6%, and the MS(ASAP) of intermediate 15-1 = 400.

[0230] Synthesis of organic compound M15:

[0231] Intermediate 3-3 (10 mmol) and intermediate 15-1 (20 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1) and potassium carbonate (30 mmol) were added. Under a nitrogen atmosphere, the reaction solution was heated to 100 °C and stirred for 6 h. After the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then extracted and washed with water for liquid separation. The organic phase was subjected to column chromatography and recrystallization to obtain organic compound M15. The molar amount of organic compound M15 was 7.59 mmol, the yield of organic compound M15 was 75.9%, and the MS (ASAP) of organic compound M15 was 936.

[0232] Example 16

[0233] The synthetic route of organic compound M16 is as follows:

[0234]

[0235] Synthesis of intermediate 16-1:

[0236] Intermediate 7-2 (10 mmol) and compound 10-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1) and potassium carbonate (30 mmol) were added. Under a nitrogen atmosphere, the reaction solution was heated to 100 °C and stirred for 6 h. After the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then extracted and washed with water for liquid separation. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 16-1. The molar amount of intermediate 16-1 was 8.13 mmol, the yield of intermediate 16-1 was 81.3%, and the MS (ASAP) of intermediate 16-1 was 400.

[0237] Synthesis of organic compound M16:

[0238] Intermediate 3-3 (10 mmol) and intermediate 16-1 (20 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1) and potassium carbonate (30 mmol) were added. Under a nitrogen atmosphere, the reaction solution was heated to 100 °C and stirred for 6 h. After the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then extracted and washed with water for liquid separation. The organic phase was subjected to column chromatography and recrystallization to obtain organic compound M16. The molar amount of organic compound M16 was 7.38 mmol, the yield of organic compound M16 was 73.8%, and the MS (ASAP) of organic compound M16 was 936.

[0239] Example 17

[0240] The synthetic route of organic compound M17 is as follows:

[0241]

[0242] Synthesis of Intermediate 17-3:

[0243] Dissolve Intermediate 17-1 (20 mmol) and Compound 17-2 (10 mmol) in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and add Pd(PPh3)4 (0.1) and potassium carbonate (30 mmol); under a nitrogen atmosphere, heat the reaction solution to 100 °C and stir for 6 h; after the reaction solution is cooled, rotary evaporate to remove most of the solvent, then extract and wash with water and separate the layers, and subject the organic phase to column chromatography and recrystallization to obtain Intermediate 17-3. The molar amount of Intermediate 17-3 is 8.87 mmol, the yield of Intermediate 17-3 is 88.7%, and the MS (ASAP) of Intermediate 17-3 = 400.

[0244] Synthesis of Organic Compound M17:

[0245] Dissolve Intermediate 17-3 (20 mmol) and Intermediate 3-3 (10 mmol) in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and add Pd(PPh3)4 (0.1) and potassium carbonate (30 mmol); under a nitrogen atmosphere, heat the reaction solution to 100 °C and stir for 6 h; after the reaction solution is cooled, rotary evaporate to remove most of the solvent, then extract and wash with water and separate the layers, and subject the organic phase to column chromatography and recrystallization to obtain Organic Compound M17. The molar amount of Organic Compound M17 is 6.94 mmol, the yield of Organic Compound M17 is 69.4%, and the MS (ASAP) of Organic Compound M17 = 936.

[0246] Comparative Example

[0247] The comparative example of this application provides a comparative compound CBP, and its structural formula is shown as follows:

[0248]

[0249] (II) Energy Level, Extinction Coefficient and Refractive Index of Organic Compounds

[0250] The energy levels of organic compounds can be obtained by quantum calculations, such as using time-dependent density functional theory (TD-DFT) through Gaussian09W (Gaussian Inc.). For specific simulation methods, reference can be made to WO2011141110. First, the molecular geometry is optimized using the semi-empirical method "Ground State / DFT / Default Spin / B3LYP / 6-31G(d)" (Charge 0 / Spin Singlet). The energy structure of the organic molecule is calculated by the TD-DFT method "TD-SCF / DFT / Default Spin / B3PW91" and the basis set "6-31G(d)" (Charge 0 / Spin Singlet). The calculated results of the first excited singlet state energy (S1) of organic compounds M1 to M17 and the comparative compound CBP are shown in Table 1.

[0251] In addition, the organic compounds M1 to M17 provided in Examples 1 to 17 and the comparative compound CBP provided in the comparative example are respectively vapor-deposited on 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). The incident angle is adjusted to 70°. The test environment is an atmospheric environment. The test results of the extinction coefficient (k) and refractive index (n) of the organic compounds M1 to M17 and the comparative compound CBP are obtained by the ellipsometer, and the results are shown in Table 1:

[0252] Table 1

[0253]

[0254]

[0255] As can be seen from Table 1, the organic compounds M1 to M17 provided in the embodiments of the present application have weak absorption ability in the visible light band, but have high absorption performance in the ultraviolet band, which can improve the transmittance of visible light and effectively resist the possible damage to the inside of the device caused by external high-energy light. Moreover, compared with the comparative compound CBP, the organic compounds M1 to M17 provided in the embodiments of the present application have a higher refractive index, and the higher refractive index can ensure better light extraction effect.

[0256] (III) Preparation and Characterization of OLED Devices

[0257] The following is a detailed description of the preparation process of an OLED device adopting the above organic electronic device structure through specific preparation examples.

[0258] The structure of the OLED device is: ITO / Ag / ITO (anode) / HATCN / SFNFB / m-CP:Ir(p-ppy)3 / NaTzF2 / LiF / Mg:Ag / light extraction layer. The preparation steps of the OLED-1 device are as follows:

[0259] Clean the ITO conductive glass anode layer, ultrasonically clean it with deionized water, acetone, and isopropanol for 15 minutes, and then treat it in a plasma cleaner for 5 minutes to improve the electrode work function;

[0260] Deposit the hole injection layer material HATCN on the ITO anode layer by vacuum evaporation to form a hole injection layer with a thickness of 5 nm, and the evaporation rate

[0261] Deposit the hole transport material SFNFB on the hole injection layer by vacuum evaporation to form a hole transport layer with a thickness of 80 nm;

[0262] Deposit the light-emitting layer on the hole transport layer. Use m-CP as the host material and Ir(p-ppy)3 as the doping material. The mass ratio of Ir(p-ppy)3 to m-CP is 1:9 to form a light-emitting layer with a thickness of 30 nm;

[0263] Deposit the electron transport material NaTzF2 on the light-emitting layer by vacuum evaporation to form an electron transport layer with a thickness of 30 nm;

[0264] Deposit the electron injection layer LiF by vacuum evaporation on the electron transport layer to form an electron injection layer with a thickness of 1 nm;

[0265] Deposit the cathode Mg:Ag layer by vacuum evaporation on the electron injection layer. The doping ratio of Mg:Ag is 9:1 to form a cathode layer with a thickness of 15 nm;

[0266] Deposit the light extraction layer by vacuum evaporation on the cathode layer. The light extraction layer material is the organic compound M1 with a thickness of 60 nm.

[0267] Referring to the preparation method of the OLED-1 device, respectively select the organic compounds M-2 to M-17 synthesized in the examples of the present application as the light extraction layer materials of the OLED device, and correspondingly prepare the OLED-2 to OLED-17 devices. It can be understood that in the preparation methods of the above OLED-1 to OLED-17 devices, except for the different materials of the light extraction layer, other experimental conditions are the same.

[0268] Furthermore, referring to the preparation method of the OLED-1 device, the comparative compound CBP was used as the light extraction layer material, and the comparative example OLED-Ref device was correspondingly prepared. Compared with the preparation method of the OLED-1 device, in the preparation method of the OLED-Ref device, except for the different material of the light extraction layer, other experimental conditions were the same.

[0269] The structures of the compounds involved in the device preparation method are as follows:

[0270]

[0271] In the embodiments of the present application, the current-voltage (J-V) characteristics of OLED-1 to OLED-17 and the OLED-Ref device were characterized, and the luminous efficiency of the device was recorded at the same time. The results are shown in Table 2. Among them, the luminous efficiency is the data obtained when the current density is 10 mA·cm -2 .

[0272] Table 2

[0273] Organic electronic device Light extraction layer material Luminous efficiency (cd / A) OLED-1 Organic compound M1 109 OLED-2 Organic compound M2 129 OLED-3 Organic compound M3 131 OLED-4 Organic compound M4 122 OLED-5 Organic compound M5 111 OLED-6 Organic compound M6 116 OLED-7 Organic compound M7 119 OLED-8 Organic compound M8 121 OLED-9 Organic compound M9 114 OLED-10 Organic compound M10 108 OLED-11 Organic compound M11 110 OLED-12 Organic compound M12 117 OLED-13 Organic compound M13 115 OLED-14 Organic compound M14 113 OLED-15 Organic compound M15 111 OLED-16 Organic compound M16 113 OLED-17 Organic compound M17 125 OLED-Ref Comparative compound CBP 87

[0274] As can be seen from Table 2, compared with the comparative example device OLED-Ref, the organic compounds M1 to M17 provided in the embodiments of the present application as the light extraction layer of the OLED device can significantly improve the luminous efficiency of the device.

[0275] Compared with the light extraction layer material (comparative compound CBP) in the comparative example device OLED-Ref, the parent nucleus of the organic compound provided in the embodiments of the present application is a poly(p-xylene) group. By introducing aromatic groups or heteroaromatic groups at both ends of the poly(p-xylene) group, and introducing trifluoromethyl groups on the aromatic groups or heteroaromatic groups. Among them, the heteroaromatic group is selected from triazine groups, and the aromatic group is selected from phenyl, diphenyl, triphenyl, tetraphenyl, naphthylphenyl, phenanthrenylphenyl, naphthylnaphthyl, phenanthrenylnaphthyl, phenanthrenylphenanthryl or triphenylene groups. The combination of these groups improves the refractive index and glass transition temperature of the organic compound, so that when the organic compound is used as the light extraction layer material in the organic electronic device, it can effectively improve the refractive index and thermal stability of the light extraction layer, and thus is beneficial to improving the light extraction efficiency and service life of the organic electronic device.

[0276] It should be noted that the introduction of strong electron-withdrawing groups (such as trifluoromethyl groups) is beneficial to increasing the distance between organic compound molecules, and thus is beneficial to improving the refractive index of the organic compound material.

[0277] In the description of the present application, the terms "first" and "second" are used only for descriptive purposes and cannot be construed as indicating or implying relative importance or implicitly specifying the quantity of the indicated technical features. Thus, features defined with "first" and "second" may explicitly or implicitly include one or more features. In the description of the present application, the meaning of "a plurality" is two or more, unless otherwise specifically defined.

[0278] In the above embodiments, the descriptions of the respective embodiments have their own emphases. For parts not detailed in a certain embodiment, reference may be made to the relevant descriptions of other embodiments.

[0279] Among the embodiments, implementation manners and related technical features of the present application, they can be combined and replaced with each other without conflict.

[0280] 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 modifications 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 general structural formula of the organic compound is shown in Formula (1): Wherein, Ar1 and Ar2 are selected from any one or a combination of more than one of a hydrogen atom, a deuterium atom, a linear alkyl group having 1 to 20 C atoms, an alkoxy group having 1 to 20 C atoms, a thioalkoxy group having 1 to 20 C atoms, a branched or cyclic alkyl group having 3 to 20 C atoms, an alkoxy group having 3 to 20 C atoms, a thioalkoxy group having 3 to 20 C atoms, a silyl group, a keto group having 1 to 20 C atoms, an alkoxycarbonyl group having 2 to 20 C atoms, an aryloxycarbonyl group having 7 to 20 C atoms, a cyano group, a carbamoyl group, a halocarbonyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, CF3, Cl, Br, F, a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, an aryloxy group having 5 to 60 ring atoms, and a heteroaryloxy group having 5 to 60 ring atoms.

2. The organic compound according to claim 1, wherein Ar1 and Ar2 are selected from any one or a combination of more than one of the following groups: Wherein, the dashed line represents a connecting bond between two groups; R2 to R5 are selected from any one or a combination of more than one of a hydrogen atom, a deuterium atom, a linear alkyl group having 1 to 20 C atoms, an alkoxy group having 1 to 20 C atoms, a thioalkoxy group having 1 to 20 C atoms, a branched or cyclic alkyl group having 3 to 20 C atoms, an alkoxy group having 3 to 20 C atoms, a thioalkoxy group having 3 to 20 C atoms, a silyl group, a keto group having 1 to 20 C atoms, an alkoxycarbonyl group having 2 to 20 C atoms, an aryloxycarbonyl group having 7 to 20 C atoms, a cyano group, a carbamoyl group, a halocarbonyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, CF3, Cl, Br, F, a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, an aryloxy group having 5 to 60 ring atoms, and a heteroaryloxy group having 5 to 60 ring atoms; among R2 to R5, two or more adjacent groups do not form a ring or form an aliphatic, aromatic or heteroaromatic ring system with a single ring or multiple rings.

3. The organic compound according to claim 2, wherein, Ar1 and Ar2 are selected from any one or a combination of more than one of the following groups:

4. The organic compound according to claim 3, wherein Ar1 and Ar2 are selected from any one or a combination of more than one of the following groups:

5. The organic compound according to any one of claims 1 to 4, characterized in that, R2 to R5 are selected from a single bond or any one or a combination of more than one of the following groups: Wherein, W is selected from N or CR8; X1 is selected from O, S, NR9, CR 10 R 11 ; R8 to R 11 selected from any one or a combination of more of a hydrogen atom, a deuterium atom, a linear alkyl group having 1 to 20 C atoms, an alkoxy group having 1 to 20 C atoms, a thioalkoxy group having 1 to 20 C atoms, a branched or cyclic alkyl group having 3 to 20 C atoms, an alkoxy group having 3 to 20 C atoms, a thioalkoxy group having 3 to 20 C atoms, a silyl group, a keto group having 1 to 20 C atoms, an alkoxycarbonyl group having 2 to 20 C atoms, an aryloxycarbonyl group having 7 to 20 C atoms, a cyano group, a carbamoyl group, a halocarbonyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, CF3, Cl, Br, F, a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, an aryloxy group having 5 to 60 ring atoms, a heteroaryloxy group having 5 to 60 ring atoms; R8 to R 11 Among them, two or more adjacent groups do not form a ring or form an aliphatic, aromatic ring system or heteroaromatic ring system having a single ring or multiple rings.

6. The organic compound according to claim 2, wherein The organic compound is selected from any one of the compounds shown in Formula 2-1 to Formula 2-12:

7. The organic compound according to claim 2 or 6, characterized in that, R2 is selected from a hydrogen atom, CF3 or a phenyl group substituted by at least one CF3.

8. The organic compound according to claim 1, characterized in that, The refractive index of the organic compound for light with a wavelength of 630 nm is greater than 1.7; the extinction coefficient of the organic compound for light with a wavelength of 430 nm is less than 0.

1.

9. An organic electronic device, characterized in that, Including: 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 light extraction layer, disposed on a side of the second electrode away from the first electrode; Wherein, the material of the light extraction layer comprises at least one organic compound as described in any one of claims 1 to 8.

10. A display panel, characterized in that, An organic electronic device comprising the organic compound as claimed in claim 9.

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