Organic compounds, mixtures, compositions, organic light-emitting devices, and display panels

Abstract

This application discloses an organic compound, a mixture, a composition, an organic light-emitting device, and a display panel. The general formula of the organic compound is as follows; the molecular structure of the organic compound consists of two of the following: an electrophilically hybridized nitrogen atom combined with a fluorenyl structure, a dibenzofuran structure, and a dibenzothiophene structure. This gives the organic compound sufficiently strong hole transport and stability. When the organic compound of this application is applied to the light-emitting auxiliary layer, it can effectively block excitons and suppress exciton reverse transport, which is beneficial to improving the luminous efficiency and lifetime of the organic light-emitting device.

Description

Technical Field

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

[0002] Currently, organic electroluminescent devices (OLEDs) typically consist of an anode, a cathode, and an organic functional layer between them. The organic material in the organic layer converts electrical energy into light energy, thus achieving organic electroluminescence. To improve the luminous efficiency and lifespan of OLEDs, the organic functional layer often includes a light-emitting layer. When an OLED operates, a voltage is applied between the anode and cathode. The anode injects holes into the organic layer, and the cathode injects electrons. The injected holes and electrons meet to form excitons, which emit light when they radiatively transition back to the ground state. With its self-emissive nature, high brightness, high efficiency, low voltage drive, wide viewing angle, high contrast, and high response, organic electroluminescent devices have broad application prospects and great development potential.

[0003] In the light-emitting functional layer, the exciton energy in the excited state is higher than that in the ground state. Without obstruction, these excited excitons will diffuse into adjacent functional layers, leading to decreased device efficiency and lifetime. Therefore, the development of materials for the light-emitting auxiliary layer is crucial. By employing light-emitting auxiliary materials with suitable carrier transport capabilities and excited-state energy levels, organic electroluminescent devices can achieve a balance in carrier transport and block excitons in the light-emitting functional layer. This allows electrons and holes to recombine in the central region of the light-emitting functional layer, thereby reducing exciton quenching and effectively improving luminous efficiency and device lifetime.

[0004] However, existing organic electroluminescent auxiliary materials have insufficient transport properties and low stability, which can easily lead to the inability of the device's voltage, efficiency, and lifespan to meet the requirements, severely limiting the application of organic electroluminescent elements.

[0005] Therefore, there is an urgent need to develop new luminescent auxiliary materials to overcome the above-mentioned defects. Summary of the Invention

[0006] This application provides an organic compound, mixture, composition, organic light-emitting device, and display panel. When the organic compound of this application is applied to the light-emitting auxiliary layer, it can achieve effective exciton blocking and suppress exciton reverse transport, which is beneficial to improving the luminous efficiency and lifespan of the organic light-emitting device.

[0007] The first aspect of this application provides an organic compound, which is shown in general formula (1):

[0008]

[0009] X1 and X2 are independently selected from CR1R2, O or S, and at least one of X1 and X2 is selected from O or S;

[0010] L1 and L2 are each independently selected from single bonds or phenylene compounds;

[0011] Ar 1 ~Ar 4 Each is independently selected from one or more combinations of aromatic groups having 6 to 30 substituted or unsubstituted ring atoms and heteroaromatic groups having 5 to 30 substituted or unsubstituted ring atoms;

[0012] R1 and R2 are each independently selected from one or more combinations of hydrogen, deuterium, straight-chain alkyl groups having 1 to 20 carbon atoms, branched alkyl groups having 3 to 20 carbon atoms, and substituted or unsubstituted aromatic groups having 6 to 12 ring atoms.

[0013] A second aspect of this application provides a mixture comprising at least one organic functional material and at least one of the aforementioned organic compounds, wherein the organic functional material is selected from at least one of hole injection materials, hole transport materials, electron injection materials, electron transport materials, light-emitting auxiliary materials, hole blocking materials, guest materials, host materials, and quantum dot materials.

[0014] A third aspect of this application provides a composition comprising at least one organic solvent and at least one of the aforementioned organic compounds, or the composition comprising at least one of the aforementioned organic solvents and a mixture thereof.

[0015] A fourth aspect of this application provides an organic light-emitting device, the organic light-emitting device comprising:

[0016] First electrode;

[0017] The second electrode is disposed opposite to the first electrode;

[0018] An organic functional layer is located between the first electrode and the second electrode. The material of the organic functional layer includes at least one of the above-mentioned organic compounds, or the material of the organic functional layer includes the above-mentioned mixtures, or the organic functional layer is made of the above-mentioned composition.

[0019] The fifth aspect of this application provides a display panel, the display panel including the above-described organic light-emitting device.

[0020] This application provides an organic compound, mixture, composition, organic light-emitting device, and display panel. The organic compound's molecular structure consists of two of the following: electrophilic hybridized nitrogen atoms combined with fluorenyl, dibenzofuran, and dibenzothiophene structures. This gives the organic compound sufficiently strong hole transport and stability. When the organic compound is applied to the light-emitting auxiliary layer, it can effectively block excitons and suppress exciton reverse transport, which is beneficial to improving the luminous efficiency and lifespan of the organic light-emitting device. Attached Figure Description

[0021] To more clearly illustrate the technical solutions in the embodiments of this application, the accompanying drawings used in the description of the embodiments will be briefly introduced below. Obviously, the accompanying drawings described below are only some embodiments of this application. For those skilled in the art, other drawings can be obtained based on these drawings without creative effort.

[0022] Figure 1 This is a schematic diagram of the structure of the organic light-emitting device provided in the embodiments of this application;

[0023] Figure 2 This is a molecular model diagram of the general formula of this application;

[0024] Explanation of reference numerals in the attached figures:

[0025] 100. Organic light-emitting device; 1. Substrate; 10. Organic functional layer; 11. First electrode; 12. Hole injection layer; 13. Hole transport layer; 14. Light-emitting auxiliary layer; 15. Light-emitting functional layer; 16. Electron transport layer; 17. Electron injection layer; 18. Second electrode; a, X 1 Atoms; b, X 2 Atoms; c and N atoms. Detailed Implementation

[0026] The technical solutions of the embodiments of this application will be clearly and completely described below with reference to the accompanying drawings. Obviously, the described embodiments are only some embodiments of this application, and not all embodiments. Based on the embodiments of this application, all other embodiments obtained by those skilled in the art without creative effort are within the scope of protection of this application.

[0027] This application provides an organic compound, mixture, composition, organic light-emitting device, and display panel. These are described in detail below. It should be noted that the order of description of the following embodiments is not intended to limit the preferred order of the embodiments. Furthermore, in the description of this application, the term "comprising" means "including but not limited to". The terms first, second, third, etc., are used merely as illustrative and do not impose numerical requirements or establish an order. Various embodiments of the present invention may exist in a range format; it should be understood that the description in a range format is merely for convenience and brevity and should not be construed as a rigid limitation on the scope of the invention; therefore, it should be considered that the range description has specifically disclosed all possible sub-ranges and single numerical values ​​within that range. For example, it should be considered that a range description from 1 to 6 has specifically disclosed sub-ranges, such as from 1 to 3, from 1 to 4, from 1 to 5, from 2 to 4, from 2 to 6, from 3 to 6, etc., and single numbers within the range, such as 1, 2, 3, 4, 5, and 6, regardless of the range. Additionally, whenever a numerical range is indicated herein, it means including any referenced number (fraction or integer) within the indicated range.

[0028] In this application, aromatic groups, aromatic families, and aromatic ring systems have the same meaning and can be used interchangeably.

[0029] In this application, heteroaromatic groups, heteroaromatic families, and heteroaromatic ring systems have the same meaning and can be used interchangeably.

[0030] In this application, "substitution" means that the hydrogen atom in the substituent is replaced by the substituent.

[0031] In this application, when the same substituent appears multiple times, it can be independently selected from different groups. If the general formula contains multiple R, then R can be independently selected from different groups.

[0032] In this application, "substituted or unsubstituted" means that the defined group may or may not be substituted. When the defined group is substituted, it should be understood that the defined group can be substituted by one or more substituents R, wherein R is selected from, but is not limited to: deuterium, cyano, isocyano, nitro or halogen, alkyl containing 1-20 carbon atoms, heterocyclic group containing 3-20 ring atoms, aromatic group containing 6-20 ring atoms, heteroaromatic group containing 5-20 ring atoms, -NR'R'', silyl, carbonyl, alkoxycarbonyl, aryloxycarbonyl, carbamoyl, halocarbamoyl, etc. Formyl, isocyanate, thiocyanate, isothiocyanate, hydroxyl, trifluoromethyl, and the above groups may be further substituted by substituents acceptable in the art; it is understood that R' and R'' in -NR'R'' are independently selected from, but not limited to: H, deuterium, cyano, isocyano, nitro or halogen, alkyl containing 1-10 carbon atoms, heterocyclic group containing 3-20 ring atoms, aromatic group containing 6-20 ring atoms, and heteroaromatic group containing 5-20 ring atoms. Preferably, R is selected from, but not limited to: deuterium, cyano, isocyano, nitro or halogen, alkyl containing 1-10 carbon atoms, heterocyclic group containing 3-10 ring atoms, aromatic group containing 6-20 ring atoms, heteroaromatic group containing 5-20 ring atoms, silyl, carbonyl, alkoxycarbonyl, aryloxycarbonyl, carbamoyl, halocarbamoyl, formyl, isocyanate group, thiocyanate group, isothiocyanate group, hydroxyl, trifluoromethyl, and the above groups may also be further substituted with substituents acceptable in the art.

[0033] In this application, "ring atom number" refers to the number of atoms in the ring itself of a structural compound obtained by atomic bonding to form a ring (e.g., monocyclic compound, fused ring compound, cross-linked compound, carbocyclic compound, heterocyclic compound). When the ring is substituted by a substituent, the atoms contained in the substituent are not included in the ring-forming atoms. The same applies to the "ring atom number" described below unless otherwise specified. For example, the benzene ring has 6 ring atoms, the naphthalene ring has 10 ring atoms, and the thiophene group has 5 ring atoms.

[0034] In this application, "aryl or aromatic group" refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removing one hydrogen atom. It can be a monocyclic aryl, a fused-ring aryl, or a polycyclic aryl, and for polycyclic rings, at least one of them is an aromatic ring system. For example, "substituted or unsubstituted aryl having 6 to 40 ring atoms" refers to an aryl containing 6 to 40 ring atoms, preferably a substituted or unsubstituted aryl having 6 to 30 ring atoms, more preferably a substituted or unsubstituted aryl having 6 to 18 ring atoms, and particularly preferably a substituted or unsubstituted aryl having 6 to 14 ring atoms, and optionally further substituted on the aryl group; suitable examples include, but are not limited to: phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, fluoranyl, triphenylene, pyrene, perylene, tetraphenyl, fluorenyl, dinaphthylphenyl, acenaphthyl and their derivatives. It is understandable that multiple aryl groups can also be interrupted by short non-aromatic units (e.g., <10% non-H atoms, such as C, N or O atoms), specifically acenaphthene, fluorene, or 9,9'-diarylfluorene, triarylamine, and diaryl ether systems should also be included in the definition of aryl.

[0035] In this application, "heteroaryl or heteroaromatic group" refers to an aryl group in which at least one carbon atom is replaced by a non-carbon atom, which can be an N atom, an O atom, an S atom, etc. For example, "substituted or unsubstituted heteroaryl group having 5 to 40 ring atoms" refers to a heteroaryl group having 5 to 40 ring atoms, preferably a substituted or unsubstituted heteroaryl group having 6 to 30 ring atoms, more preferably a substituted or unsubstituted heteroaryl group having 6 to 18 ring atoms, and particularly preferably a substituted or unsubstituted heteroaryl group having 6 to 14 ring atoms. The heteroaryl group may optionally be further substituted, and suitable examples include, but are not limited to, thiophene, furanyl, pyrrole, imidazolyl, diazolyl, triazolyl, imidazolyl, pyridyl, bipyridyl, and pyrimidine. Triazinyl, acridineyl, pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridinylpyrimidinyl, pyridinylpyrazinyl, benzothiopheneyl, benzofuranyl, indolyl, pyrroloimidazolyl, pyrrolopyrrolyl, thienopyrrolyl, thienopyrrolyl, furanolyl, furanolyl, thienofuranyl, benzoisoxazolyl, benzoisothiazolyl, benzoimidazolyl, o-diazonyl, phenanthridineyl, primidyl, quinazolinoneyl, dibenzothiopheneyl, dibenzofuranyl, carbazoleyl and their derivatives.

[0036] In this application, "alkyl" can mean straight-chain, branched, and / or cyclic alkyl. The number of carbon atoms in an alkyl group can be 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Phrases containing this term, such as "C1-9 alkyl," refer to alkyl groups containing 1 to 9 carbon atoms, and each time it appears, it can independently be C1 alkyl, C2 alkyl, C3 alkyl, C4 alkyl, C5 alkyl, C6 alkyl, C7 alkyl, C8 alkyl, or C9 alkyl. Non-limiting examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, 3 7-Dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl, n-undecyl, n-dodecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, n-tridecyl, n-tetradecyl, n-pentadecanyl, n-hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, n-hepta ...

[0037] In this application, "amino group" refers to an amine derivative having the structural feature of the formula -N(X)2, wherein each "X" is independently H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, etc. Non-limiting types of amino groups include -NH2, -N(alkyl)2, -NH(alkyl), -N(cycloalkyl)2, -NH(cycloalkyl), -N(heterocyclic)2, -NH(heterocyclic), -N(aryl)2, -NH(aryl), -N(alkyl)(aryl), -N(alkyl)(heterocyclic), -N(cycloalkyl)(heterocyclic), -N(aryl)(heteroaryl), -N(alkyl)(heteroaryl), etc.

[0038] In this application, unless otherwise defined, hydroxyl refers to -OH, carboxyl refers to -COOH, carbonyl refers to -C(=O)-, amino refers to -NH2, formyl refers to -C(=O)H, haloformyl refers to -C(=O)Z (where Z represents halogen), carbamoyl refers to -C(=O)NH2, isocyanate refers to -NCO, and isothiocyanate refers to -NCS.

[0039] In this application, the term "alkoxy" refers to a group with the structure "-O-alkyl", that is, an alkyl group as defined above that is attached to other groups via an oxygen atom. Suitable examples of phrases containing this term include, but are not limited to: methoxy (-O-CH3 or -OMe), ethoxy (-O-CH2CH3 or -OEt), and tert-butoxy (-OC(CH3)3 or -OtBu).

[0040] In this application, the "*" connected to a single bond indicates a connection or fusion site.

[0041] In this application, when no linking site is specified in the group, it means that any linkable site in the group is selected as the linking site.

[0042] In this application, when no fusion site is specified in the group, it means that any fusionable site in the group is selected as the fusion site, preferably two or more sites in the adjacent position of the group are fusion sites.

[0043] In this application, when the same group contains multiple substituents with the same symbol, the substituents can be the same as or different from each other, for example... The six Rs on the benzene ring can be the same or different from each other.

[0044] In this application, the single bonds connecting the substituents extend through the corresponding ring, indicating that the substituent can be attached to any position on the ring, for example... R is attached to any substituted site on the benzene ring; such as express Can be with A fused ring can be formed at any position on the benzene ring.

[0045] The terms cycloalkyl or cycloalkyl as used in this application have the same meaning and are interchangeable.

[0046] Organic electroluminescent auxiliary materials have insufficient transport properties and low stability, which can easily lead to the inability of devices to meet the requirements for voltage, efficiency and lifespan, severely limiting the application of organic electroluminescent elements.

[0047] To solve the above-mentioned technical problems, the first aspect of this application provides the organic compound as shown in general formula (1):

[0048] ,

[0049] X1 and X2 are independently selected from CR1R2, O or S, and at least one of X1 and X2 is selected from O or S;

[0050] L1 and L2 are each independently selected from single bonds or phenylene compounds;

[0051] Ar 1 ~Ar 4 Each is independently selected from one or more combinations of aromatic groups having 6 to 30 substituted or unsubstituted ring atoms and heteroaromatic groups having 5 to 30 substituted or unsubstituted ring atoms;

[0052] R1 and R2 are each independently selected from one or more combinations of hydrogen, deuterium, straight-chain alkyl groups having 1 to 20 carbon atoms, branched alkyl groups having 3 to 20 carbon atoms, and substituted or unsubstituted aromatic groups having 6 to 12 ring atoms.

[0053] In some embodiments, the organic compound is selected from any one of formulas (A), (B), (C), (D), and (E):

[0054]

[0055]

[0056] .

[0057] In some embodiments, the Ar 1 ~Ar 4 Each is independently selected from at least one of the following structures:

[0058] .

[0059] In some specific embodiments, the Ar 1 ~Ar 4 Each is independently selected from at least one of the following structures:

[0060] .

[0061] In some embodiments, the organic compound is selected from any of the following structures:

[0062] .

[0063] It is understood that the organic compounds in the embodiments of this application are not limited to the examples above.

[0064] The organic compounds described in this application can be used as functional materials in the organic functional layers of electronic devices. The organic functional layers include a hole injection layer (HIL), a hole transport layer (HTL), an electron transport layer (ETL), an electron injection layer (EIL), a hole blocking layer (HBL), a prime layer, and an emission material layer (EML).

[0065] In some embodiments, the organic compound described in this application is used in the light-emitting auxiliary layer.

[0066] This application provides an organic compound whose molecular structure consists of an electrophilically hybridized nitrogen atom combined with one of the following structures: fluorenyl, dibenzofuran, or dibenzothiophene. This gives the organic compound sufficiently strong hole transport and stability. When the organic compound of this application is applied to the light-emitting auxiliary layer, it can effectively block excitons and suppress exciton reverse transport, which is beneficial to improving the luminous efficiency and lifetime of organic light-emitting devices.

[0067] Accordingly, this application also provides a mixture comprising at least one organic functional material and at least the above-mentioned organic compound, wherein the organic functional material is selected from at least one of hole injection materials, hole transport materials, electron injection materials, electron transport materials, light-emitting auxiliary materials, hole blocking materials, guest materials, host materials and quantum dot materials.

[0068] In some embodiments, the quantum dot material includes inorganic quantum dot materials.

[0069] This application also provides a composition comprising at least one organic solvent and at least one of the above-described organic compounds, or, the composition comprising at least one of the above-described organic solvents and the above-described mixture.

[0070] In some embodiments, the organic solvent is selected from at least one of aromatic or heteroaromatic compounds, esters, aromatic ketones or aromatic ethers, aliphatic ketones or aliphatic ethers, alicyclic or olefinic compounds, and borate esters or phosphate esters.

[0071] Examples of aromatic or heteroaromatic organic solvents suitable for this application include, but are not limited to: p-diisopropylbenzene, pentobenzene, tetrahydronaphthalene, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, dipentylbenzene, tripentylbenzene, pentylene, 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, cyclohexylbenzene, benzylbutylbenzene Benzene, dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, 1-methylnaphthalene, 1,2,4-trichlorobenzene, 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, quinoline, isoquinoline, methyl 2-furanoate, ethyl 2-furanoate, etc.

[0072] Examples of aromatic ketone-based organic solvents suitable for this application include, but are not limited to: 1-tetrahydronaphthone, 2-tetrahydronaphthone, 2-(phenylepoxy)tetrahydronaphthone, 6-(methoxy)tetrahydronaphthone, acetophenone, phenylacetone, benzophenone, and their derivatives, such as 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylphenylacetone, 3-methylphenylacetone, 2-methylphenylacetone, etc.

[0073] Examples of aromatic ether-based organic solvents suitable for this application include, but are not limited to: 3-phenoxytoluene, butoxybenzene, p-anisaldehyde dimethyl acetal, tetrahydro-2-phenoxy-2H-pyran, 1,2-dimethoxy-4-(1-propenyl)benzene, 1,4-benzodioxane, 1,3-dipropylbenzene, 2,5-dimethoxytoluene, 4-ethylbenzene, 1,3-dipropoxybenzene, 1,2,4-trimethoxybenzene, 4-(1-propenyl)-1,2-dimethoxybenzene, 1,3-dimethoxybenzene, glycidylphenyl ether, dibenzyl ether, 4-tert-butylanisole, trans-p-propenylanisole, 1,2-dimethoxybenzene, 1-methoxynaphthalene, diphenyl ether, 2-phenoxymethyl ether, 2-phenoxytetrahydrofuran, ethyl-2-naphthyl ether.

[0074] Examples of aliphatic ketone-based organic solvents suitable for this application include, but are not limited to: 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2,5-hexanedione, 2,6,8-trimethyl-4-nonanone, frankinc, phorone, isophorone, 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.

[0075] Examples of ester-based organic solvents suitable for this application include, but are not limited to: alkyl octanoate, alkyl sebacate, alkyl stearate, alkyl benzoate, alkyl phenylacetate, alkyl cinnamate, alkyl oxalate, alkyl maleate, alkyl lactone, alkyl oleate, etc. Octyl octanoate, diethyl sebacate, diallyl phthalate, and isononyl isononanoate are particularly preferred.

[0076] In some embodiments, at least one of the organic solvents includes one or more of aromatic or heteroaromatic organic solvents.

[0077] In some embodiments, at least one of the organic solvents further includes at least one of methanol, ethanol, 2-methoxyethanol, dichloromethane, trichloromethane, chlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1,4-dioxane, acetone, methyl ethyl ketone, 1,2-dichloroethane, 3-phenoxytoluene, 1,1,1-trichloroethane, 1,1,2,2-tetrachloroethane, ethyl acetate, butyl acetate, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, tetrahydronaphthalene, naphthane, and indene.

[0078] In some embodiments, organic solvents particularly suitable for this application are solvents with Hansen solubility parameters within the following ranges:

[0079] δd (dispersion force) is in the range of 17.0 to 23.2 MPa1 / 2, especially in the range of 18.5 to 21.0 MPa1 / 2;

[0080] δp (polar force) is in the range of 0.2 to 12.5 MPa1 / 2, especially in the range of 2.0 to 6.0 MPa1 / 2;

[0081] δh (hydrogen bond force) is in the range of 0.9 to 14.2 MPa1 / 2, especially in the range of 2.0 to 6.0 MPa1 / 2.

[0082] In the compositions provided in this application, the boiling point of the organic solvent must be considered when selecting it. In this application, the boiling point of the organic solvent is ≥150°C; preferably ≥180°C; more preferably ≥200°C; even more preferably ≥250°C; and most preferably ≥275°C or ≥300°C. Boiling points within these ranges are beneficial for preventing nozzle clogging of the inkjet printhead. The organic solvent can evaporate from the solvent system to form a thin film containing functional materials.

[0083] In some embodiments, the composition provided in this application is a solution.

[0084] In other embodiments, the composition provided in this application is a suspension.

[0085] In the embodiments of this application, the composition may include 0.01 wt% to 20 wt% of the organic compound or the mixture. Further, the organic compound or the mixture may be 0.1 wt% to 15 wt% of the composition. Preferably, the organic compound or the mixture may be 0.2 wt% to 10 wt% of the composition. This application also relates to the use of the composition as a coating or printing ink in the preparation of organic light-emitting devices, particularly preferably by a preparation method involving printing or coating.

[0086] Suitable printing or coating technologies include (but are not limited to) inkjet printing, nozzle printing, letterpress printing, screen printing, dip coating, spin coating, doctor blade coating, roller printing, torsional roller printing, offset printing, flexographic printing, rotary printing, spraying, brushing or pad printing, slot extrusion coating, etc. Gravure printing, inkjet printing, and other similar techniques are preferred. The solution or suspension may further include one or more components such as surfactants, lubricants, wetting agents, dispersants, hydrophobic agents, adhesives, etc., to adjust viscosity, improve film-forming properties, and enhance adhesion.

[0087] This application also provides an organic light-emitting device 100, the organic light-emitting device 100 comprising: a first electrode 11; a second electrode 18 disposed opposite to the first electrode 11; and an organic functional layer 10 located between the first electrode 11 and the second electrode 18; the material of the organic functional layer 10 comprises at least one of the above-mentioned organic compounds, or the material of the organic functional layer 10 comprises the above-mentioned mixtures, or the organic functional layer 10 is made of the above-mentioned composition.

[0088] In some embodiments, the organic functional layer 10 includes a light-emitting auxiliary layer 14, the material of which includes at least one of the organic compounds.

[0089] In some embodiments, the organic functional layer 10 further includes a hole transport layer 13 and a light-emitting functional layer 15, wherein the light-emitting auxiliary layer 14 is located between the hole transport layer 13 and the light-emitting functional layer 15, and the hole transport layer 13 is located between the light-emitting auxiliary layer 14 and the first electrode 11.

[0090] In some embodiments, the first electrode 11 is the anode and the second electrode 18 is the cathode.

[0091] In some embodiments, the organic functional layer 10 further includes at least one of a hole injection layer 12, an electron transport layer 16, and an electron injection layer 17; wherein the hole injection layer 12 is located on the side of the hole input layer away from the light-emitting auxiliary layer 14, the electron transport layer 16 is located on the side of the light-emitting functional layer 15 away from the light-emitting auxiliary layer 14, and the electron injection layer 17 is located on the side of the electron transport layer 16 away from the light-emitting functional layer 15.

[0092] In some embodiments, the organic light-emitting device 100 further includes a substrate 1 located on the side of the first electrode 11 away from the organic functional layer 10.

[0093] In one specific embodiment, the organic light-emitting device 100 includes a substrate 1, a first electrode 11, a hole injection layer 12, a hole transport layer 13, a light-emitting auxiliary layer 14, a light-emitting functional layer 15, an electron transport layer 16, an electron injection layer 17, and a second electrode 18 stacked sequentially, wherein the first electrode 11 is an anode and the second electrode 18 is a cathode.

[0094] In some embodiments, the organic light-emitting device 100 is a green organic light-emitting device 100.

[0095] In some embodiments, the organic light-emitting device 100 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, with OLEDs, OLEECs, and OLEFETs being particularly preferred.

[0096] Substrate 1 can be opaque or transparent. A transparent substrate 1 can be used to fabricate a transparent light-emitting device. See, for example, Bulovic et al., Nature 1996, 380, p29, and Gu et al., Appl. Phys. Lett. 1996, 68, p2606. Substrate 1 can be rigid or flexible. The material of substrate 1 can be plastic, metal, semiconductor wafer, or glass. Preferably, substrate 1 has a smooth surface, and substrate 1 without surface defects is further preferred. In a preferred example, substrate 1 is flexible and can be selected from polymer films or plastics with a glass transition temperature Tg of 150°C or higher, preferably 200°C or higher, more preferably 250°C or higher, and most preferably 300°C or higher. Examples of suitable flexible substrates 1 are polyethylene terephthalate (PET) and polyethylene glycol (2,6-naphthalene) (PEN).

[0097] The first electrode 11 may comprise a conductive metal, metal oxide, or conductive polymer. Holes can be readily injected into the HIL, HTL, or EML. In one example, the absolute value of the difference between the work function of the first electrode 11 and the HOMO level or valence band level of the light emitter in the light-emitting functional layer 15 or the p-type semiconductor material of the HIL, HTL, or EBL 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, etc. Other suitable materials for the first electrode 11 are known and can be readily selected by those skilled in the art. 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 deposition, etc.

[0098] In some embodiments, the first electrode 11 is patterned. The patterned ITO conductive substrate 1 is commercially available and can be used to fabricate the device according to this application.

[0099] The second electrode 18 may comprise a conductive metal or metal oxide. The second electrode 18 can readily inject electrons into the EIL or ETL or directly into the light-emitting functional layer 15. In one embodiment, the absolute value of the difference between the work function of the second electrode 18 and the LUMO level or conduction band level of the light emitter or the n-type semiconductor material serving as the EIL, ETL, or HBL in the light-emitting functional layer 15 is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. In principle, all materials suitable for use as cathodes in OLEDs can potentially serve as the material for the second electrode 18 of the organic electronic device in this application. Examples of materials for the second electrode 18 include, but are not limited to: Al, Au, Ag, Ca, Ba, Mg, LiF / Al, magnesium-silver alloy, BaF2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO, etc. The material for the second electrode 18 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 deposition, etc.

[0100] In some embodiments, the emission wavelength of the organic light-emitting device 100 is between 300 and 1000 nm, preferably between 350 and 900 nm, and more preferably between 400 and 800 nm.

[0101] This application provides an organic light-emitting device 100, which includes a light-emitting auxiliary layer 14 prepared from the above-mentioned organic compound. The molecular structure of the organic compound consists of one of the following: an electrophilic hybridized nitrogen atom combined with a fluorenyl structure, a dibenzofuran structure, or a dibenzothiophene structure. This gives the organic compound sufficiently strong hole transport and stability. When the organic compound of this application is applied to the light-emitting auxiliary layer 14, it can effectively block excitons and suppress exciton reverse transport, which is beneficial to improving the luminous efficiency and lifetime of the organic light-emitting device.

[0102] This application embodiment also provides a display panel, which includes the above-described organic light-emitting device 100.

[0103] In some embodiments, the display panel further includes an array substrate and an encapsulation layer, wherein the organic light-emitting device 100 is located on the array substrate and electrically connected to the array substrate, and the encapsulation layer covers the array substrate and the encapsulation layer.

[0104] It is understood that the array substrate is used to drive the organic light-emitting device 100, and the encapsulation layer is used to protect the organic light-emitting device 100.

[0105] In some embodiments, the display panel further includes a cover plate and an optical film, the optical film being located between the encapsulation layer and the cover plate; wherein the optical film includes at least one of a polarizer, a light conversion layer, and a color filter.

[0106] This application provides a display panel including the aforementioned organic light-emitting device 100. The organic light-emitting device 100 includes a light-emitting auxiliary layer 14 containing the organic compound of the aforementioned embodiment. The molecular structure of the organic compound of the aforementioned embodiment consists of one of the following: an electrophilically hybridized nitrogen atom combined with a fluorenyl structure, a dibenzofuran structure, or a dibenzothiophene structure. This gives the organic compound sufficiently strong hole transport and stability. When the organic compound of this application is applied to the light-emitting auxiliary layer 14, it can effectively block excitons and suppress exciton reverse transport, which is beneficial to improving the luminous efficiency and lifespan of the organic light-emitting device, thereby enhancing the performance of the display panel.

[0107] This application also provides the application of the organic light-emitting device 100 in various electronic devices, including but not limited to display devices, lighting devices, light sources, sensors, etc.

[0108] This application also provides electronic devices that include the organic light-emitting device 100, including but not limited to display devices, lighting devices, light sources, sensors, etc.

[0109] The organic compounds provided in this application will be described below with reference to preferred embodiments. However, the organic compounds provided in this application are not limited to the following embodiments. It should be understood that the appended claims summarize the scope of this application. Under the guidance of the concept of this application, those skilled in the art should realize that any changes made to the various embodiments of this application will be covered by the spirit and scope of the claims of this application. Specific Implementation

[0111] Example 1

[0112] This embodiment provides a method for synthesizing compound P1. The synthetic route for organic compound P1 is as follows:

[0113]

[0114] (1) Synthesis of intermediate P1-2:

[0115] P1-1 (56.3 g, 200 mmol) and pinacol diborate (76.2 g, 300 mmol) were weighed and placed in a clean three-necked flask. Pd(dppf)Cl2 (1.5 g, 2.0 mmol), potassium acetate (39.2 g, 400 mmol), and dioxane (400 mL) were added. The mixture was purged with nitrogen three times and refluxed at 100°C for 12 h. After natural cooling, the mixture was washed with water and separated. The organic phase was dried and then evaporated to dryness. Column chromatography was used to obtain intermediate P1-2 with a yield of 89.1%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate P1-2 was: MS(ASAP) = 329.

[0116] (2) Synthesis of intermediate P1-3:

[0117] P1-2 (52.6 g, 160 mmol) and P1-1 (45.0 g, 160 mmol) were weighed and placed in a clean three-necked flask. Pd(PPh3)4 (1.8 g, 1.6 mmol), potassium carbonate (44.2 g, 320 mmol), anhydrous toluene (400 mL), ethanol (100 mL), and deionized water (100 mL) were added. The mixture was purged with nitrogen three times and refluxed at 80°C for 6 h. After natural cooling, the mixture was washed with water and separated. The organic phase was dried and then evaporated to dryness. Column chromatography was used to obtain intermediate P1-3 in 80.2% yield. The MS (ASAP) of intermediate P1-3 was 403.

[0118] (3) Synthesis of intermediate P1-4:

[0119] P1-3 (48.4 g, 120 mmol) and diphenylamine (18.6 g, 110 mmol) were weighed and placed in a clean three-necked flask. Pd(dba)2 (1.1 g, 1.2 mmol), 2-dicyclohexylphosphine-2′,4′,6′-triisopropylbiphenyl (X-Phos) (1.1 g, 2.4 mmol), sodium tert-butoxide (23.0 g, 240 mmol), and anhydrous toluene (400 mL) were added. The mixture was purged with nitrogen three times and refluxed at 100 °C for 3 h. After natural cooling, the mixture was washed with water and separated. The organic phase was dried and then evaporated to dryness. Column chromatography was used to obtain intermediate P1-4 in 85.1% yield. The MS (ASAP) of intermediate P1-4 was 536.

[0120] (4) Synthesis of compound P1:

[0121] P1-4 (53.6 g, 100 mmol) and P1-5 (24.5 g, 100 mmol) were weighed and placed in a clean three-necked flask. Pd(dba)2 (0.9 g, 1.0 mmol), X-Phos (1.0 g, 2.0 mmol), sodium tert-butoxide (23.0 g, 200 mmol), and anhydrous toluene (400 mL) were added. The mixture was purged with nitrogen three times and refluxed at 100 °C for 12 h. After natural cooling, the mixture was washed with water and separated. The organic phase was dried and then evaporated to dryness. Column chromatography was used to obtain compound P1 in 78.6% yield. The MS (ASAP) value of compound P1 was 745.

[0122] Example 2

[0123] This embodiment provides a method for synthesizing compound P2. The synthetic route for organic compound P2 is as follows:

[0124]

[0125] The synthesis of intermediates P1-2 to P1-4 will not be described in detail.

[0126] Synthesis of compound P2: Following the synthesis method of compound P1 in Example 1, P1-5 was replaced with P2-1 to obtain compound P2 with a yield of 77.4% and MS (ASAP) = 795.

[0127] Example 3

[0128] This embodiment provides a method for synthesizing compound P3. The synthetic route for organic compound P3 is as follows:

[0129]

[0130] The synthesis of intermediates P1-2 to P1-4 will not be described in detail.

[0131] Synthesis of compound P3: Following the synthesis method of compound P1 in Example 1, P1-5 was replaced with P3-1 to obtain compound P3 with a yield of 83.3% and MS (ASAP) = 759.

[0132] Example 4

[0133] This embodiment provides a method for synthesizing compound P4. The synthetic route for organic compound P4 is as follows:

[0134]

[0135] The synthesis of intermediates P1-2 to P1-4 will not be described in detail.

[0136] Synthesis of compound P4: Following the synthesis method of compound P1 in Example 1, P1-5 was replaced with P4-1 to obtain compound P4 with a yield of 88.7% and MS (ASAP) = 821.

[0137] Example 5

[0138] This embodiment provides a method for synthesizing compound P5. The synthetic route for organic compound P5 is as follows:

[0139]

[0140] The synthesis of intermediates P1-2 to P1-4 will not be described in detail.

[0141] Synthesis of compound P5: Following the synthesis method of compound P1 in Example 1, P1-5 was replaced with P5-1 to obtain compound P5 with a yield of 79.1% and MS (ASAP) = 821.

[0142] Example 6

[0143] This embodiment provides a method for synthesizing compound P6. The synthetic route for organic compound P6 is as follows:

[0144]

[0145] The synthesis of intermediates P1-2 to P1-4 will not be described in detail.

[0146] Synthesis of compound P6: Following the synthesis method of compound P1 in Example 1, P1-5 was replaced with P6-1 to obtain compound P6 with a yield of 85.2% and MS (ASAP) = 785.

[0147] Example 7

[0148] This embodiment provides a method for synthesizing compound P7. The synthetic route for organic compound P7 is as follows:

[0149]

[0150] The synthesis of intermediates P1-2 to P1-4 will not be described in detail.

[0151] Synthesis of compound P7: Following the synthesis method of compound P1 in Example 1, P1-5 was replaced with P7-1 to obtain compound P7 with a yield of 74.5% and MS (ASAP) = 834.

[0152] Example 8

[0153] This embodiment provides a method for synthesizing compound P8. The synthetic route for organic compound P8 is as follows:

[0154]

[0155] The synthesis of intermediates P1-2 to P1-3 will not be described in detail.

[0156] (1) Synthesis of intermediate P8-1: Following the synthesis method of intermediate P1-4 in Example 1, diphenylamine was replaced with N-phenyl-4-benzidine to obtain intermediate P8-1 with a yield of 73.9% and MS (ASAP) = 612.

[0157] (2) Synthesis of compound P8: Referring to the synthesis method of compound P1 in Example 1, P1-5 was replaced with P8-2 to obtain compound P8 with a yield of 82.8% and MS (ASAP) = 795.

[0158] Example 9

[0159] This embodiment provides a method for synthesizing compound P9. The synthetic route for organic compound P9 is as follows:

[0160]

[0161] The synthesis of intermediates P1-2~P1-3 and P8-1 will not be described in detail.

[0162] Synthesis of compound P9: Following the synthesis method of compound P1 in Example 1, P1-5 was replaced with P9-1 to obtain compound P9 with a yield of 76.5% and MS (ASAP) = 851.

[0163] Example 10

[0164] This embodiment provides a method for synthesizing compound P10. The synthetic route for organic compound P10 is as follows:

[0165]

[0166] (1) Synthesis of intermediate P10-2:

[0167] P10-1 (59.5 g, 200 mmol) and pinacol diborate (76.2 g, 300 mmol) were weighed and placed in a clean three-necked flask. Pd(dppf)Cl2 (1.5 g, 2.0 mmol), potassium acetate (39.2 g, 400 mmol), and dioxane (400 mL) were added. The mixture was purged with nitrogen three times, and the mixture was heated to 100°C and refluxed for 12 h. After natural cooling, the mixture was washed with water and separated. The organic phase was dried and then evaporated to dryness. Column chromatography was used to obtain intermediate P10-2 in 85.7% yield. The MS (ASAP) value of intermediate P10-2 was 345.

[0168] (2) Synthesis of intermediate P10-3:

[0169] P10-2 (55.2 g, 160 mmol) and P10-1 (47.6 g, 160 mmol) were weighed and placed in a clean three-necked flask. Pd(PPh3)4 (1.8 g, 1.6 mmol), potassium carbonate (44.2 g, 320 mmol), anhydrous toluene (400 mL), ethanol (100 mL), and deionized water (100 mL) were added. The mixture was purged with nitrogen three times and refluxed at 80°C for 12 h. After natural cooling, the mixture was washed with water and separated. The organic phase was dried and then evaporated to dryness. Column chromatography was used to obtain intermediate P10-3 in 76.8% yield. The MS (ASAP) value of intermediate P10-3 was 435.

[0170] (3) Synthesis of intermediate P10-4:

[0171] P10-3 (52.2 g, 120 mmol) and diphenylamine (18.6 g, 110 mmol) were weighed and placed in a clean three-necked flask. Pd(dba)2 (1.1 g, 1.2 mmol), X-Phos (1.1 g, 2.4 mmol), sodium tert-butoxide (23.0 g, 240 mmol), and anhydrous toluene (400 mL) were added. The mixture was purged with nitrogen three times and refluxed at 100 °C for 6 h. After natural cooling, the mixture was washed with water and separated. The organic phase was dried and then evaporated to dryness. Column chromatography was used to obtain intermediate P10-4 in 73.5% yield. The MS (ASAP) of intermediate P10-4 was 568.

[0172] (4) Synthesis of compound P10:

[0173] P10-4 (56.8 g, 100 mmol) and P10-5 (32.1 g, 100 mmol) were weighed and placed in a clean three-necked flask. Pd(dba)2 (0.9 g, 1.0 mmol), X-Phos (1.0 g, 2.0 mmol), sodium tert-butoxide (19.2 g, 200 mmol), and anhydrous toluene (400 mL) were added. The mixture was purged with nitrogen three times and refluxed at 100 °C for 12 h. After natural cooling, the mixture was washed with water and separated. The organic phase was dried and then evaporated to dryness. Column chromatography was used to obtain compound P1 in 64.7% yield. The MS (ASAP) of compound P1 was 853.

[0174] Example 11

[0175] This embodiment provides a method for synthesizing compound P11. The synthetic route for organic compound P11 is as follows:

[0176]

[0177] The synthesis of intermediates P10-2 to P10-4 will not be described in detail.

[0178] Synthesis of compound P11: Following the synthesis method of compound P10 in Example 10, P10-5 was replaced with P1-5 to obtain compound P11 with a yield of 71.2% and MS (ASAP) = 851.

[0179] Example 12

[0180] This embodiment provides a method for synthesizing compound P12. The synthetic route for the organic compound P12 is as follows:

[0181]

[0182] The synthesis of intermediates P10-2 to P10-4 will not be described in detail.

[0183] Synthesis of compound P12: Following the synthesis method of compound P10 in Example 10, P10-5 was replaced with P4-1 to obtain compound P12 with a yield of 80.1% and MS (ASAP) = 853.

[0184] Example 13

[0185] This embodiment provides a method for synthesizing compound P13. The synthetic route for organic compound P13 is as follows:

[0186]

[0187] The synthesis of intermediates P10-2 to P10-4 will not be described in detail.

[0188] Synthesis of compound P13: Following the synthesis method of compound P10 in Example 10, P10-5 was replaced with P6-1 to obtain compound P13 with a yield of 75.4% and MS (ASAP) = 817.

[0189] Example 14

[0190] This embodiment provides a method for synthesizing compound P14. The synthetic route for the organic compound P14 is as follows:

[0191]

[0192] The synthesis of intermediates P10-2 to P10-4 will not be described in detail.

[0193] Synthesis of compound P14: Following the synthesis method of compound P10 in Example 10, P10-5 was replaced with P7-1 to obtain compound P14 with a yield of 66.9% and MS (ASAP) = 866.

[0194] Example 15

[0195] This embodiment provides a method for synthesizing compound P15. The synthetic route for organic compound P15 is as follows:

[0196]

[0197] (1) The synthesis of intermediate P1-2 will not be described in detail.

[0198] (2) Synthesis of intermediate P15-1:

[0199] P1-2 (49.3 g, 150 mmol) and P10-1 (44.6 g, 150 mmol) were weighed and placed in a clean three-necked flask. Pd(PPh3)4 (1.7 g, 1.5 mmol), potassium carbonate (41.4 g, 300 mmol), anhydrous toluene (400 mL), ethanol (100 mL), and deionized water (100 mL) were added. The mixture was purged with nitrogen three times and refluxed at 80°C for 12 h. After natural cooling, the mixture was washed with water and separated. The organic phase was dried and then evaporated to dryness. Column chromatography was used to obtain intermediate P15-1 in 72.9% yield. The MS (ASAP) of intermediate P15-1 was 419.

[0200] (3) Synthesis of intermediate P15-2:

[0201] P15-1 (50.3 g, 120 mmol) and diphenylamine (18.6 g, 120 mmol) were weighed and placed in a clean three-necked flask. Pd(dba)2 (1.1 g, 1.2 mmol), X-Phos (1.1 g, 2.4 mmol), sodium tert-butoxide (23.0 g, 240 mmol), and anhydrous toluene (400 mL) were added. The mixture was purged with nitrogen three times and refluxed at 100 °C for 6 h. After natural cooling, the mixture was washed with water and separated. The organic phase was dried and then evaporated to dryness. Column chromatography was used to obtain intermediate P15-2 in 68.1% yield. The MS (ASAP) of intermediate P15-2 was 552.

[0202] (4) Synthesis of compound P15:

[0203] P15-2 (55.2 g, 100 mmol) and P15-3 (21.9 g, 100 mmol) were weighed and placed in a clean three-necked flask. Pd(dba)2 (0.9 g, 1.0 mmol), X-Phos (1.0 g, 2.0 mmol), sodium tert-butoxide (19.2 g, 200 mmol), and anhydrous toluene (400 mL) were added. The mixture was purged with nitrogen three times and refluxed at 100 °C for 12 h. After natural cooling, the mixture was washed with water and separated. The organic phase was dried and then evaporated to dryness. Column chromatography was used to obtain compound P15 in 64.7% yield. The MS (ASAP) value of compound P15 was 735.

[0204] Example 16

[0205] This embodiment provides a method for synthesizing compound P16. The synthetic route for the organic compound P16 is as follows:

[0206]

[0207] The synthesis of intermediates P1-2, P15-1 and P15-2 will not be described in detail.

[0208] Synthesis of compound P16: Following the synthesis method of compound P15 in Example 15, P15-3 was replaced with P9-1 to obtain compound P16 with a yield of 70.5% and MS (ASAP) = 791.

[0209] Example 17

[0210] This embodiment provides a method for synthesizing compound P17. The synthetic route for organic compound P17 is as follows:

[0211]

[0212] The synthesis of intermediates P1-2, P15-1 and P15-2 will not be described in detail.

[0213] Synthesis of compound P17: Following the synthesis method of compound P15 in Example 15, P15-3 was replaced with P4-1 to obtain compound P17 with a yield of 83.8% and MS (ASAP) = 837.

[0214] Example 18

[0215] This embodiment provides a method for synthesizing compound P18. The synthetic route for organic compound P18 is as follows:

[0216]

[0217] The synthesis of intermediates P1-2, P15-1 and P15-2 will not be described in detail.

[0218] Synthesis of compound P18: Following the synthesis method of compound P15 in Example 15, P15-3 was replaced with P1-5 to obtain compound P18 with a yield of 85.2% and MS (ASAP) = 761.

[0219] Example 19

[0220] This embodiment provides a method for synthesizing compound P19. The synthetic route for organic compound P19 is as follows:

[0221]

[0222] The synthesis of intermediates P1-2, P15-1 and P15-2 will not be described in detail.

[0223] Synthesis of compound P19: Following the synthesis method of compound P15 in Example 15, P15-3 was replaced with P10-5 to obtain compound P19 with a yield of 69.9% and MS (ASAP) = 837.

[0224] Example 20

[0225] This embodiment provides a method for synthesizing compound P20. The synthetic route for organic compound P20 is as follows:

[0226]

[0227] (1) Synthesis of intermediate P20-2:

[0228] P20-1 (61.6 g, 200 mmol) and pinacol diborate (76.2 g, 300 mmol) were weighed and placed in a clean three-necked flask. Pd(dppf)Cl2 (1.5 g, 2.0 mmol), potassium acetate (39.2 g, 400 mmol), and dioxane (400 mL) were added. The mixture was purged with nitrogen three times, and the mixture was heated to 100°C and refluxed for 12 h. After natural cooling, the mixture was washed with water and separated. The organic phase was dried and then evaporated to dryness. Column chromatography was used to obtain intermediate P20-2 in 92.0% yield. The MS (ASAP) value of intermediate P20-2 was 355.

[0229] (2) Synthesis of intermediate P20-3:

[0230] P20-2 (56.8 g, 160 mmol) and diphenylamine (32.5 g, 192 mmol) were weighed and placed in a clean three-necked flask. Pd(dba)2 (1.5 g, 1.6 mmol), X-Phos (1.5 g, 3.2 mmol), sodium tert-butoxide (30.7 g, 320 mmol), and anhydrous toluene (400 mL) were added. The mixture was purged with nitrogen three times and refluxed at 100 °C for 6 h. After natural cooling, the mixture was washed with water and separated. The organic phase was dried and then evaporated to dryness. Column chromatography was used to obtain intermediate P20-3 in 69.6% yield. The MS (ASAP) of intermediate P20-3 was 487.

[0231] (3) Synthesis of intermediate P20-4:

[0232] P20-3 (58.4 g, 120 mmol) and P1-1 (33.8 g, 120 mmol) were weighed and placed in a clean three-necked flask. Pd(PPh3)4 (1.4 g, 1.2 mmol), potassium carbonate (33.1 g, 240 mmol), anhydrous toluene (400 mL), ethanol (100 mL), and deionized water (100 mL) were added. The mixture was purged with nitrogen three times and refluxed at 80°C for 6 h. After natural cooling, the mixture was washed with water and separated. The organic phase was dried and then evaporated to dryness. Column chromatography was used to obtain intermediate P20-4 in 77.6% yield. The MS (ASAP) of intermediate P20-4 was 562.

[0233] (4) Synthesis of compound P20:

[0234] P20-4 (56.2 g, 100 mmol) and P15-3 (21.9 g, 100 mmol) were weighed and placed in a clean three-necked flask. Pd(dba)2 (0.9 g, 1.0 mmol), X-Phos (1.0 g, 2.0 mmol), sodium tert-butoxide (23.0 g, 200 mmol), and anhydrous toluene (400 mL) were added. The mixture was purged with nitrogen three times and refluxed at 100 °C for 12 h. After natural cooling, the mixture was washed with water and separated. The organic phase was dried and then evaporated to dryness. Column chromatography was used to obtain compound P20 in 72.4% yield. The MS (ASAP) value of compound P20 was 745.

[0235] Example 21

[0236] This embodiment provides a method for synthesizing compound P21. The synthetic route for organic compound P21 is as follows:

[0237]

[0238] The synthesis of intermediates P20-2 to P20-4 will not be described in detail.

[0239] Synthesis of compound P21: Following the synthesis method of compound P20 in Example 20, P15-3 was replaced with P9-1 to obtain compound P21 with a yield of 84.9% and MS (ASAP) = 801.

[0240] Example 22

[0241] This embodiment provides a method for synthesizing compound P22. The synthetic route for organic compound P22 is as follows:

[0242]

[0243] The synthesis of intermediates P20-2 to P20-4 will not be described in detail.

[0244] Synthesis of compound P22: Following the synthesis method of compound P20 in Example 20, P15-3 was replaced with P4-1 to obtain compound P22 with a yield of 80.5% and MS (ASAP) = 847.

[0245] Example 23

[0246] This embodiment provides a method for synthesizing compound P23. The synthetic route for organic compound P23 is as follows:

[0247]

[0248] The synthesis of intermediates P20-2 to P20-4 will not be described in detail.

[0249] Synthesis of compound P23: Following the synthesis method of compound P20 in Example 20, P15-3 was replaced with P7-1 to obtain compound P23 with a yield of 80.5% and MS (ASAP) = 860.

[0250] Example 24

[0251] This embodiment provides a method for synthesizing compound P24. The synthetic route for organic compound P24 is as follows:

[0252]

[0253] The synthesis of intermediates P20-2 to P20-4 will not be described in detail.

[0254] Synthesis of compound P24: Following the synthesis method of compound P20 in Example 20, P15-3 was replaced with P10-5 to obtain compound P24 with a yield of 71.9% and MS (ASAP) = 837.

[0255] Example 25

[0256] This embodiment provides a method for synthesizing compound P25. The synthetic route for organic compound P25 is as follows:

[0257]

[0258] The synthesis of intermediates P20-2 and P20-3 will not be described in detail.

[0259] (1) Synthesis of intermediate P25-1:

[0260] P20-3 (58.4 g, 120 mmol) and P10-1 (35.7 g, 120 mmol) were weighed and placed in a clean three-necked flask. Pd(PPh3)4 (1.4 g, 1.2 mmol), potassium carbonate (33.1 g, 240 mmol), anhydrous toluene (400 mL), ethanol (100 mL), and deionized water (100 mL) were added. The mixture was purged with nitrogen three times and refluxed at 80°C for 6 h. After natural cooling, the mixture was washed with water and separated. The organic phase was dried and then evaporated to dryness. Column chromatography was used to obtain intermediate P25-1 in 70.7% yield. The MS (ASAP) of intermediate P25-1 was 578.

[0261] (2) Synthesis of compound P25:

[0262] P25-1 (57.8 g, 100 mmol) and P15-3 (21.9 g, 100 mmol) were weighed and placed in a clean three-necked flask. Pd(dba)2 (0.9 g, 1.0 mmol), X-Phos (1.0 g, 2.0 mmol), sodium tert-butoxide (23.0 g, 200 mmol), and anhydrous toluene (400 mL) were added. The mixture was purged with nitrogen three times and refluxed at 100 °C for 12 h. After natural cooling, the mixture was washed with water and separated. The organic phase was dried and then evaporated to dryness. Column chromatography was used to obtain compound P25 in 77.9% yield. The MS (ASAP) of compound P25 was 761.

[0263] Example 26

[0264] This embodiment provides a method for synthesizing compound P26. The synthetic route for organic compound P26 is as follows:

[0265]

[0266] The synthesis of intermediates P20-2, P20-3 and P25-1 will not be described in detail.

[0267] Synthesis of compound P26: Following the synthesis method of compound P25 in Example 25, P15-3 was replaced with P3-1 to obtain compound P26 with a yield of 82.5% and MS (ASAP) = 801.

[0268] Example 27

[0269] This embodiment provides a method for synthesizing compound P27. The synthetic route for organic compound P27 is as follows:

[0270]

[0271] The synthesis of intermediates P20-2, P20-3 and P25-1 will not be described in detail.

[0272] Synthesis of compound P27: Following the synthesis method of compound P25 in Example 25, P15-3 was replaced with P4-1 to obtain compound P27 with a yield of 79.2% and MS (ASAP) = 863.

[0273] Example 28

[0274] This embodiment provides a method for synthesizing compound P28. The synthetic route for organic compound P28 is as follows:

[0275]

[0276] The synthesis of intermediates P20-2, P20-3 and P25-1 will not be described in detail.

[0277] Synthesis of compound P28: Following the synthesis method of compound P25 in Example 25, P15-3 was replaced with P7-1 to obtain compound P28 with a yield of 78.4% and MS (ASAP) = 876.

[0278] Example 29

[0279] The synthetic route for organic compound P29 is as follows:

[0280]

[0281] The synthesis of intermediates P20-2, P20-3 and P25-1 will not be described in detail.

[0282] Synthesis of compound P29: Following the synthesis method of compound P25 in Example 25, P15-3 was replaced with P10-5 to obtain compound P29 with a yield of 67.6% and MS (ASAP) = 837.

[0283] Comparative Examples 1-4

[0284] This application also provides comparative examples, with the organic compounds referred to as "Comparative Compound REF01, Comparative Compound REF02, Comparative Compound REF03, and Comparative Compound REF04", and their chemical structural formulas are shown below:

[0285]

[0286] Comparative Example 1

[0287] The synthetic route for the organic compound REF01 is as follows:

[0288]

[0289] (1) Synthesis of intermediate P30-2:

[0290] P1-1 (45.0 g, 160 mmol) and P30-1 (49.6 g, 160 mmol) were weighed and placed in a clean three-necked flask. Pd(PPh3)4 (1.8 g, 1.6 mmol), potassium carbonate (44.2 g, 320 mmol), anhydrous toluene (400 mL), ethanol (100 mL), and deionized water (100 mL) were added. The mixture was purged with nitrogen three times and refluxed at 80°C for 6 h. After natural cooling, the mixture was washed with water and separated. The organic phase was dried and then evaporated to dryness. Column chromatography was used to obtain intermediate P30-2 in 78.6% yield. The MS (ASAP) value of intermediate P30-2 was 385.

[0291] (2) Synthesis of compound REF01:

[0292] P30-2 (38.5 g, 100 mmol) and P30-3 (24.5 g, 100 mmol) were weighed and placed in a clean three-necked flask. Pd(dba)2 (0.9 g, 1.0 mmol), X-Phos (1.0 g, 2.0 mmol), sodium tert-butoxide (19.2 g, 200 mmol), and anhydrous toluene (400 mL) were added. The mixture was purged with nitrogen three times and refluxed at 100 °C for 12 h. After natural cooling, the mixture was washed with water and separated. The organic phase was dried and then evaporated to dryness. Column chromatography was used to obtain compound REF01 in 80.3% yield. The MS (ASAP) of compound REF01 was 594.

[0293] Comparative Example 2

[0294] The synthetic route for the organic compound REF02 is as follows:

[0295]

[0296] (1) Synthesis of intermediate P31-2:

[0297] P20-3 (78.0 g, 160 mmol) and P31-1 (45.0 g, 160 mmol) were weighed and placed in a clean three-necked flask. Pd(PPh3)4 (1.8 g, 1.6 mmol), potassium carbonate (44.2 g, 320 mmol), anhydrous toluene (400 mL), ethanol (100 mL), and deionized water (100 mL) were added. The mixture was purged with nitrogen three times and refluxed at 80°C for 6 h. After natural cooling, the mixture was washed with water and separated. The organic phase was dried and then evaporated to dryness. Column chromatography was used to obtain intermediate P31-2 in 73.9% yield. The MS (ASAP) of intermediate P31-2 was 562.

[0298] (2) Synthesis of compound REF02:

[0299] P31-2 (56.2 g, 100 mmol) and diphenylamine (16.9 g, 100 mmol) were weighed and placed in a clean three-necked flask. Pd(dba)2 (0.9 g, 1.0 mmol), X-Phos (1.0 g, 2.0 mmol), sodium tert-butoxide (19.2 g, 200 mmol), and anhydrous toluene (400 mL) were added. The mixture was purged with nitrogen three times and refluxed at 100 °C for 12 h. After natural cooling, the mixture was washed with water and separated. The organic phase was dried and then evaporated to dryness. Column chromatography was used to obtain compound REF02 in 69.3% yield. The MS (ASAP) value of compound REF02 was 695.

[0300] Comparative Example 3

[0301] The synthetic route for the organic compound REF03 is as follows:

[0302]

[0303] (1) Synthesis of intermediate P32-3:

[0304] P32-1 (52.6 g, 160 mmol) and P32-2 (47.6 g, 160 mmol) were weighed and placed in a clean three-necked flask. Pd(PPh3)4 (1.8 g, 1.6 mmol), potassium carbonate (44.2 g, 320 mmol), anhydrous toluene (400 mL), ethanol (100 mL), and deionized water (100 mL) were added. The mixture was purged with nitrogen three times and refluxed at 80°C for 6 h. After natural cooling, the mixture was washed with water and separated. The organic phase was dried and then evaporated to dryness. Column chromatography was used to obtain intermediate P32-3 in 70.6% yield. The MS (ASAP) of intermediate P32-3 was 419.

[0305] (2) Synthesis of compound REF03:

[0306] P32-3 (21.0 g, 50 mmol) and diphenylamine (16.9 g, 200 mmol) were weighed and placed in a clean three-necked flask. Pd(dba)2 (0.9 g, 1.0 mmol), X-Phos (1.0 g, 2.0 mmol), sodium tert-butoxide (19.2 g, 200 mmol), and anhydrous toluene (400 mL) were added. The mixture was purged with nitrogen three times and refluxed at 100 °C for 12 h. After natural cooling, the mixture was washed with water and separated. The organic phase was dried and then evaporated to dryness. Column chromatography was used to obtain compound REF03 in 69.3% yield. The MS (ASAP) value of compound REF03 was 695.

[0307] Comparative Example 4

[0308] The synthetic route for the organic compound REF04 is as follows:

[0309]

[0310] (1) Synthesis of intermediate P33-2:

[0311] P33-1 (28.2 g, 100 mmol) and diphenylamine (16.9 g, 100 mmol) were weighed and placed in a clean three-necked flask. Pd(dba)2 (0.9 g, 1.0 mmol), X-Phos (1.0 g, 2.0 mmol), sodium tert-butoxide (19.2 g, 200 mmol), and anhydrous toluene (400 mL) were added. The mixture was purged with nitrogen three times and refluxed at 90 °C for 8 h. After natural cooling, the mixture was washed with water and separated. The organic phase was dried and then evaporated to dryness. Column chromatography was used to obtain intermediate P33-2 in 84.8% yield. The MS (ASAP) of intermediate P33-2 was 370.

[0312] (2) Synthesis of intermediate P33-3:

[0313] P33-2 (29.6 g, 80 mmol) and pinacol diborate (30.5 g, 120 mmol) were weighed and placed in a clean three-necked flask. Pd(dppf)Cl2 (1.5 g, 2.0 mmol), potassium acetate (31.4 g, 320 mmol), and dioxane (400 mL) were added. The mixture was purged with nitrogen three times, and the mixture was heated to 100°C and refluxed for 12 h. After natural cooling, the mixture was washed with water and separated. The organic phase was dried and then evaporated to dryness. Column chromatography was used to obtain intermediate P33-3 in 77.5% yield. The MS (ASAP) of intermediate P33-3 was 461.

[0314] (3) Synthesis of compound REF04:

[0315] P33-3 (23.1 g, 50 mmol) and P33-4 (16.2 g, 50 mmol) were weighed and placed in a clean three-necked flask. Pd(PPh3)4 (0.6 g, 0.5 mmol), potassium carbonate (13.8 g, 100 mmol), anhydrous toluene (200 mL), ethanol (50 mL), and deionized water (50 mL) were added. The mixture was purged with nitrogen three times and refluxed at 90°C for 12 h. After natural cooling, the mixture was washed with water and separated. The organic phase was dried and then evaporated to dryness. Column chromatography was used to obtain compound REF04 in 86.7% yield. The MS (ASAP) of compound REF04 was 579.

[0316] In the embodiments of this application, the energy levels of organic compounds play a crucial role. The highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energy levels of the compounds obtained in Examples 1 to 29 of this invention, as well as the comparative compounds REF01 and REF04, can be obtained through theoretical calculations. Specifically, the theoretical calculations were mainly performed using the Gaussian 09W (Gaussian Inc.) software package. Specific simulation methods can be found in WO2011141110 or as described in the following embodiments. It should be noted that the values ​​of HOMO and LUMO depend on the measurement or calculation methods used. Even for the same method, different evaluation methods, such as the starting point and peak value on the CV curve, can give different HOMO / LUMO values. Therefore, a reasonable and meaningful comparison should be made using the same measurement and evaluation methods. In the description of the embodiments of the present invention, the ground state (S0) configuration is calculated using density functional theory (DFT) under the B3LYP / 6-31G(d) or B3LYP / 6-31G(d,p) basis set. The HOMO and LUMO values ​​of the material are calculated using time-dependent density functional theory (TD-DFT) under the B3LYP / 6-31G(d) or B3LYP / 6-31G(d,p) basis set based on the optimized S0 structure, and the units are Hartree.

[0317] Table 1

[0318]

[0319] As shown in Table 1, the HOMO of the organic compounds provided in Examples 1 to 29 of this invention is maintained at -5.0 eV and below compared with the comparative compounds REF01 to REF04. They are suitable as luminescent auxiliary materials to be built between the hole transport layer 13 and the luminescent functional layer, thereby reducing the energy level barrier between the hole transport layer and the luminescent functional layer.

[0320] Fabrication and characterization of OLED devices

[0321] The organic light-emitting device 100 provided in this application embodiment can be an OLED device, and is based on Figure 1 Taking the fabrication of the organic electronic device shown as an example, the following detailed description of the fabrication method of OLED device using the organic compound provided in the embodiments of this application will be provided through specific device examples.

[0322] In the following method for fabricating OLED devices, ITO conductive glass is used as the anode substrate, PD as the hole injection material, HT as the hole transport material, Host-1 and Host-2 together as the host materials of the light-emitting functional layer, Dopant as the dopant material of the light-emitting functional layer, HB as the hole blocking material, ET and Liq as the electron transport materials, Liq as the electron injection material, and Al as the cathode material. Additionally, compound P-1 from the aforementioned synthesis example is used as the light-emitting auxiliary material to fabricate corresponding OLED devices. The chemical structural formulas of PD, HT, Host, Dopant, ET, and Liq are shown below:

[0323]

[0324] The following specific examples illustrate the fabrication process of OLED devices using the above-mentioned materials.

[0325] Taking the fabrication method of OLED devices using compound P-1 as a light-emitting auxiliary material as an example, the resulting OLED device is denoted as "OLED-1 device". The fabrication method of OLED-1 device includes the following steps:

[0326] Step a: Cleaning of the ITO conductive glass substrate: Provide an ITO conductive glass substrate and ultrasonically clean the substrate using one or more cleaning agents such as deionized water, acetone, isopropanol or chloroform to improve the work function of the anode.

[0327] Step b: Forming a hole injection layer 12 on the anode: Hole injection materials PD and HT are deposited on the anode at a deposition rate of 1 Å / s, with a deposition rate ratio of 3:97, to obtain a hole injection layer 12 with a thickness of 30 nm.

[0328] Step c: Forming a hole transport layer 13 on the hole injection layer 12: Hole transport material HT is deposited on the hole injection layer 12 at a deposition rate of 1.5 Å / s to obtain a hole transport layer 13 with a thickness of 60 nm.

[0329] Step d: Forming a light-emitting auxiliary layer 14 on the hole transport layer 13: The compound P-1 provided in the above embodiment is deposited on the hole transport layer 13 at a deposition rate of 1 Å / s to obtain a light-emitting auxiliary layer 14 with a thickness of 10 nm.

[0330] Step e: Forming a light-emitting functional layer 15 on the light-emitting auxiliary layer 14: Host-1, Host-2 and Dopant are deposited on the light-emitting auxiliary layer 14 at a deposition rate of 1 Å / s, wherein the ratio of Host-1 to Host-2 is 50:50, and the deposition rate ratio of the two Hosts and Dopant is 98:2, to obtain a light-emitting functional layer 15 with a thickness of 40 nm.

[0331] Step f: Forming an electron transport layer on the luminescent functional layer 16: In a vacuum chamber, electron transport materials ET and Liq are placed in different evaporation crucibles and subjected to high vacuum (1×10⁻⁶) conditions. -6 Under millibars, ET and Liq were co-deposited at a weight ratio of 5:5 to form an electron transport layer 16 with a thickness of 30 nm on the luminescent functional layer 15.

[0332] Step g: Forming an electron injection layer 17 on the electron transport layer 16: Electron injection material Liq is deposited on the electron transport layer 16 at a deposition rate of 1 Å / s to obtain an electron injection layer 17 with a thickness of 1 nm.

[0333] Step h: Form a cathode on the electron injection layer 17. Evaporate cathode material Al on the electron injection layer 17 at a evaporation rate of 1 Å / s to obtain a cathode with a thickness of 100 nm.

[0334] Step i: The device obtained by layer-by-layer deposition is placed in a nitrogen atmosphere glove box and encapsulated with UV-cured resin to finally obtain the OLED device.

[0335] In this embodiment, the structure of the prepared OLED-1 device is: ITO / PD:HT (3:97, 30 nm) / HT (60 nm) / compound P-1 of the present invention (10 nm) / Host-1:Host-2:Dopant (2%, 40 nm) / ET:Liq (5:5, 30 nm) / Liq (1 nm) / Al (100 nm).

[0336] Fabrication of OLED-2 to OLED-29 devices

[0337] Referring to the fabrication method of OLED-1, compounds synthesized in the examples were selected as luminescent auxiliary materials for OLED devices, and OLED-2 to OLED-29 devices were fabricated accordingly. It is understood that, in the above fabrication methods of OLED-1 to OLED-29 devices, all experimental conditions are the same except for the luminescent auxiliary materials.

[0338] Furthermore, referring to the fabrication method of the device examples, comparative compounds REF01 to REF04 were used as luminescent auxiliary materials to prepare comparative OLED-REF01 to OLED-REF04 devices respectively. Compared with the fabrication method of OLED-1 device, the experimental conditions are the same in the fabrication methods of OLED-REF01 to OLED-REF04 devices except for the luminescent auxiliary materials.

[0339] In this application, the current-voltage (JV) characteristics of OLED-1 to OLED-29 and OLED-REF01 to OLED-REF04 devices were characterized, and important parameters such as luminous efficiency and lifetime were recorded, as shown in Table 2. Luminous efficiency is defined as a current density of 10 mA / cm². 2 The relative value obtained is the lifetime (LT95), which is the time it takes for the device brightness to drop from an initial 1 knit to 95% under constant current.

[0340] Table 2

[0341]

[0342] As can be seen from the results in Table 2, the green OLED devices prepared by using the organic compounds provided in Examples 1 to 29 of this application as light-emitting auxiliary materials have lower driving voltage, higher luminous efficiency, and longer lifespan compared with the green OLED devices prepared by using the organic compounds provided in Comparative Examples 1 to 4 as light-emitting auxiliary materials. In other words, they show better performance in terms of driving voltage, luminous efficiency, and device lifespan.

[0343] according to Figure 2 The molecular optimization structure diagram shows that the general formula of this application restricts the two interconnected central ring structures (i.e., the ring structures containing X1(a) and X2(b)). This connection method facilitates the formation of a twisted conformation, and the orthogonal rigid bis(arylamine) structure (c being an N atom) is beneficial for film formation, thereby enhancing hole transport capability. Furthermore, organic electronic devices prepared using the compounds of this application as luminescent auxiliary materials exhibit superior performance compared to organic light-emitting devices using the compounds of Comparative Example 2, further demonstrating the advantages of the general formula compounds of this application in enhancing hole transport. Therefore, using the compounds of this application in green luminescent auxiliary layers can improve the driving voltage, luminous efficiency, and lifetime of organic light-emitting devices.

[0344] In summary, this application provides an organic compound, mixture, composition, organic light-emitting device, and display panel. The organic compound's molecular structure consists of two of the following: electrophilic hybridized nitrogen atoms combined with fluorenyl, dibenzofuran, and dibenzothiophene structures. This gives the organic compound sufficiently strong hole transport and stability. When the organic compound of this application is applied to the light-emitting auxiliary layer, it can effectively block excitons and suppress exciton reverse transport, which is beneficial to improving the luminous efficiency and lifespan of the organic light-emitting device.

[0345] The above provides a detailed description of an organic compound, mixture, composition, organic electronic device, and display panel provided in the embodiments of this application. Specific examples have been used to illustrate the principles and implementation methods of this application. The descriptions of the above embodiments are only for the purpose of helping to understand the methods and core ideas of this application. At the same time, for those skilled in the art, there will be changes in the specific implementation methods and application scope based on the ideas of this application. Therefore, the content of this specification should not be construed as a limitation of this application.

Claims

1. An organic compound, characterized by, The organic compound is as shown in general formula (1): ， X1and X2are independently selected from CR1R2, O or S, and at least one of X1and X2is selected from O or S; L1and L2are independently selected from a single bond; Ar 1 ~Ar 4 are each independently selected from one of the following structures: R1and R2are independently selected from a linear alkyl group having 1 to 20 carbon atoms.

2. The organic compound according to claim 1, characterized by The organic compound is selected from any one of formulae (A), (B), (C), (D) and (E): 。 3. The organic compound according to claim 1 or 2, characterized by The organic compound is selected from any one of the following structures: 。 4. A mixture characterized in that, The mixture comprises at least one organic functional material and at least one organic compound as claimed in any one of claims 1 to 3, the organic functional material being selected from at least one of a hole injection material, a hole transport material, an electron injection material, an electron transport material, a light-emitting auxiliary material, a hole blocking material, a guest material, a host material and a quantum dot material.

5. A composition characterized in that, The composition comprises at least one organic solvent and at least one organic compound as claimed in any one of claims 1 to 3, or the composition comprises at least one organic solvent and the mixture as claimed in claim 4.

6. An organic light-emitting device, characterized in that, The organic light-emitting device comprises: a first electrode; a second electrode, disposed opposite to the first electrode; an organic functional layer, located between the first electrode and the second electrode, a material of the organic functional layer comprising at least one organic compound as claimed in any one of claims 1 to 3, or a material of the organic functional layer comprising the mixture as claimed in claim 4, or the organic functional layer being made of the composition as claimed in claim 5.

7. The organic light-emitting device according to claim 6, characterized in that, The organic functional layer comprises a light-emitting auxiliary layer, a material of the light-emitting auxiliary layer comprising at least one organic compound as claimed in any one of claims 1 to 3.

8. The organic light-emitting device according to claim 7, characterized in that, The organic functional layer further comprises a hole transport layer and a light-emitting functional layer, the light-emitting auxiliary layer being located between the hole transport layer and the light-emitting functional layer, and the hole transport layer being located between the light-emitting auxiliary layer and the first electrode.

9. A display panel, characterized by, The display panel comprises the organic light-emitting device as claimed in any one of claims 6 to 8.

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