Organic compound, mixture, composition, organic electronic device, and display panel

Abstract

The invention relates to an organic compound, a mixture, a composition, an organic electronic device and a display panel, and the chemical structural formula of the organic compound is selected from any one of the structures represented by the formula (1): # imgabs0. The organic compound provided by the invention can be applied to the organic electronic device as a hole transport material, and is beneficial to improving the hole transport rate; therefore, the luminous efficiency of an organic electronic device is improved, and the service life of the organic electronic device is prolonged.

Description

Technical Field

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

[0002] The organic electroluminescence phenomenon refers to the phenomenon of converting electrical energy into light energy by using organic substances. An organic electroluminescent element using the organic electroluminescence phenomenon usually has an anode and a cathode, and an organic layer disposed between the anode and the cathode. In order to improve the efficiency and lifespan of the organic electroluminescent element, the organic layer has a multilayer structure, and each layer contains different organic substances. Specifically, the organic layer may include a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. In such an organic electroluminescent element, when a voltage is applied between the two electrodes, holes are injected into the organic layer from the anode, and electrons are injected into the organic layer from the cathode. When the injected holes and electrons meet, excitons are formed, and light is emitted when the excitons transition back to the ground state. Such an organic electroluminescent element has characteristics such as self-luminescence, high brightness, high efficiency, low driving voltage, wide viewing angle, high contrast ratio, and high responsiveness. For example, an Organic Light-Emitting Diode (OLED) has advantages such as a wide viewing angle, fast response time, low working voltage, and thin panel thickness in the applications of optoelectronic devices (such as flat panel displays and lighting), and thus has broad development potential.

[0003] In order to obtain a highly efficient organic electroluminescent device, in addition to developing high-performance light-emitting materials, the development of charge transport materials is also important. Currently, most charge transport materials are small molecule materials based on carbazole derivatives, and such materials still have the disadvantage of unbalanced hole and electron transport, resulting in low luminous efficiency and short lifespan of the devices using such materials. Summary of the Invention

[0004] An embodiment of the present application provides an organic compound, a mixture, a composition, an organic electronic device, and a display panel. The organic compound can be used as a hole transport material in an organic electronic device, which is beneficial to improving the hole transport rate, making the hole and electron transport balanced, and thus improving the luminous efficiency and service life of the organic electronic device.

[0005] To achieve the above object, according to the first aspect of the present application, there is provided an organic compound, and the chemical structural formula of the organic compound is selected from any one of the structures represented by the general formula (1):

[0006]

[0007] Wherein, Ar1 is selected from a single bond or any one of the following groups:

[0008]

[0009] Ar2 and A r3 Any one or a combination of more than one selected from the following groups:

[0010]

[0011] X is selected from N or CR3;

[0012] Y is selected from O, S, NR4 or CR5R6;

[0013] Each occurrence of R3 - R6 is independently 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, a branched-chain alkyl group having 3 to 20 C atoms, a cyclic alkyl group having 3 to 20 C atoms, a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, and a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms;

[0014] The dashed line represents the connection site.

[0015] According to the second aspect of the present application, there is provided a mixture, the mixture comprising at least one of the above-mentioned organic compounds and at least one organic functional material; the organic functional material is selected from at least one of a hole injection material, a hole transport material, an electron transport material, an electron injection material, an electron blocking material, a hole blocking material, an organic light-emitting guest material, an organic host material, and an inorganic quantum dot material.

[0016] According to the third aspect of the present application, there is also provided a composition, the composition comprising at least one organic solvent and at least one of the above-mentioned organic compounds; or the composition comprises at least one of the organic solvents and the above-mentioned mixture.

[0017] According to the fourth aspect of the present application, there is also provided an organic electronic device, the organic electronic device comprising:

[0018] A first electrode;

[0019] An organic functional layer disposed on one side of the first electrode;

[0020] A second electrode disposed on a side of the organic functional layer away from the first electrode;

[0021] Wherein, the material of the organic functional layer comprises at least one of the above-mentioned organic compounds, or the material of the organic functional layer comprises the above-mentioned mixture, or the organic functional layer is prepared from the above-mentioned composition.

[0022] According to a fifth aspect of the present application, a display panel is further provided, and the display panel includes the organic electronic device described above.

[0023] In the organic compound, mixture, composition, organic electronic device, and display panel of the embodiments of the present application, a diarylamine group is connected to a phenanthrobenzofuran group to form an organic compound of a triarylamine type containing a phenanthrobenzofuran group as shown in the general formula (1). At the same time, by defining the Ar2 group and the Ar3 group connected to N in the organic compound, the Ar2 group and the Ar3 group connected to N are selected from groups with relatively strong conjugation; under the combined action of the phenanthrobenzofuran group and the Ar2 group and the Ar3 group with relatively strong conjugation, the molecular packing in the organic compound material can be effectively improved, making the molecules of the organic compound material have greater rigidity, and further improving the glass transition temperature of the organic compound material. Moreover, the organic compound shown in the general formula (1) can be used as a hole transport material. When it is used in an organic electronic device in combination with a suitable light-emitting material, the hole transport rate can be increased, so that the transport rates of holes and electrons reach an equilibrium state, thereby improving the light-emitting efficiency and service life of the organic electronic device. In addition, the preparation cost of the organic compound shown in the general formula (1) is low, which is beneficial to reducing the manufacturing cost of the organic electronic device. Therefore, when the organic compound is used in an organic electronic device, the service life of the organic electronic device can be extended at low cost and the light-emitting efficiency of the organic electronic device can be improved.

[0024] Other features and advantages of the present application will be described in detail in the subsequent specific implementation section. BRIEF DESCRIPTION OF THE DRAWINGS

[0025] In order to more clearly illustrate the technical solutions in the embodiments of the present application, the drawings required for the description of the embodiments will be briefly introduced below. Obviously, the drawings in the following description are only some embodiments of the present application, and those skilled in the art can also obtain other drawings based on these drawings without creative efforts.

[0026] 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.

[0027] Figure 1 is a schematic structural diagram of an organic electronic device provided by an embodiment of the present application;

[0028] Figure 2 is a schematic structural diagram of another organic electronic device provided by an embodiment of the present application.

[0029] Explanation of the accompanying drawings: 100, organic electronic device; 10, substrate; 20, first electrode (anode); 30, organic functional layer; 40, hole injection layer; 50, hole transport layer; 50a, first hole transport layer; 50b, second hole transport layer; 60, light-emitting layer; 70, electron transport layer; 80, electron injection layer; 90, second electrode (cathode). DETAILED DESCRIPTION

[0030] The technical solutions in the embodiments of the present application will be described clearly and completely below in conjunction with the drawings in the embodiments of the present application.

[0031] In the present application, "substituted" means that a hydrogen atom in a substituted group is replaced by a substituent.

[0032] In this application, when the same substituent appears multiple times, it can be independently selected from different groups. 1 , then R 1 can be independently selected from different groups.

[0033] In this application, "substituted or unsubstituted" means that the defined group may be substituted or unsubstituted. When the defined group is substituted, it should be understood that it is optionally substituted by groups acceptable in the art, including but not limited to: deuterium atoms, cyano groups, isocyano groups, nitro groups, halogen atoms, C 1-10 Alkyl, C 1-10 Alkoxy, C 1-10 Alkylthio, C 6-30 Aryl, C 6-30 Aryloxy, C 6-30 Arylthio, C 3-30 Heteroaryl, C 1-30 Silane group, C 2-10 Alkylamino, C 6-30 arylamine group, or a combination of the above groups, etc.

[0034] In this application, the "number of ring atoms" refers to the number of atoms in the atoms that constitute the ring itself of a structural compound (e.g., a monocyclic compound, a condensed ring compound, a cross-linked compound, a carbocyclic compound, a heterocyclic compound) formed by atoms bonded together to form a ring. When the ring is substituted with a substituent, the atoms contained in the substituent are not included in the ring atoms. The "number of ring atoms" described below is also the same 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 thienyl group is 5.

[0035] In this application, "alkyl" may refer to a linear, branched and / or cyclic alkyl group. The carbon number of the alkyl group may be 1 to 50, 1 to 30, 1 to 20, 1 to 10 or 1 to 6. Phrases containing this term, for example, "C 1-9"Alkyl" means an alkyl group containing 1 to 9 carbon atoms, and each occurrence can independently be a C1 alkyl group, a C2 alkyl group, a C3 alkyl group, a C4 alkyl group, a C5 alkyl group, a C6 alkyl group, a C7 alkyl group, a C8 alkyl group or a C9 alkyl group. 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, adamantane, etc.

[0036] In the present application, "aryl or aromatic group" means an aromatic hydrocarbon group derived by removing one hydrogen atom from an aromatic ring compound, which can be a monocyclic aryl group, a fused-ring aryl group or a polycyclic aryl group. For polycyclic ring systems, at least one is an aromatic ring system. For example, "substituted or unsubstituted aryl group having 6 to 40 ring atoms" means an aryl group containing 6 to 40 ring atoms, preferably a substituted or unsubstituted aryl group having 6 to 30 ring atoms, more preferably a substituted or unsubstituted aryl group having 6 to 18 ring atoms, particularly preferably a substituted or unsubstituted aryl group having 6 to 14 ring atoms, and the aryl group is optionally further substituted; suitable examples include but are not limited to: benzene, biphenyl, terphenyl, naphthalene, anthracene, fluoranthene, phenanthrene, benzo[a]phenanthrene, dibenzo[a,h]anthracene, tetracene, pyrene, benzo[a]pyrene, acenaphthene, fluorene and their derivatives. It can be understood 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 such as acenaphthene, fluorene, or 9,9-diarylfluorene, triarylamine, diaryl ether systems should also be included in the definition of aryl groups.

[0037] In the present application, "heteroaryl or heteroaromatic group" means that at least one carbon atom in the aryl group is replaced by a non-carbon atom, and the non-carbon atom 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" means 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, particularly preferably a substituted or unsubstituted heteroaryl group having 6 to 14 ring atoms, and the heteroaryl group is optionally further substituted. Suitable examples include but are not limited to: triazine, pyridine, pyrimidine, imidazole, furan, thiophene, benzofuran, benzothiophene, indole, carbazole, pyrroloimidazole, pyrrolopyrrole, thiophenopyrrole, thiophenothiophene, furanopyrrole, furanofuran, thiophenofuran, benzisoxazole, benzisothiazole, benzimidazole, quinoline, isoquinoline, phthalazine, quinoxaline, phenanthridine, perimidine, quinazoline, quinazolinone, dibenzothiophene, dibenzofuran, carbazole and their derivatives.

[0038] In the present application, "amino group" refers to a derivative of amine, having a structural feature of the formula -N(X)2, where 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 group)2, -NH(heterocyclic group), -N(aryl)2, -NH(aryl), -N(alkyl)(aryl), -N(alkyl)(heterocyclic group), -N(cycloalkyl)(heterocyclic group), -N(aryl)(heteroaryl), -N(alkyl)(heteroaryl), etc.

[0039] In the present application, "*" connected to a single bond represents a connecting site or a fusion site.

[0040] In the present application, when the connecting site of a group is not specified, it means that any optional connecting site in the group can be used as the connecting site.

[0041] In the present application, when the fusion site of a group is not specified, it means that any optional fusion site in the group can be used as the fusion site, and preferably two or more sites adjacent to each other in the group are fusion sites.

[0042] In the present application, the single bond to which a substituent is connected passes through the corresponding ring, indicating that the substituent can be connected to any optional position of the ring. For example in which R is connected to any substitutable site of the benzene ring.

[0043] In the present application, "adjacent groups" means that there is no substitutable site between two substituents.

[0044] The embodiments of the present application provide an organic compound, and the chemical structural formula of the organic compound is selected from any one of the structures represented by the general formula (1):

[0045]

[0046] Among them, Ar1 is selected from a single bond or any one of the following groups:

[0047]

[0048] Ar2 and A r3 are selected from any one or a combination of more than one of the following groups:

[0049]

[0050] X is selected from N or CR3;

[0051] Y is selected from O, S, NR4 or CR5R6;

[0052] Each occurrence of R3-R6 is independently 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 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, a cyclic alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, and a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms;

[0053] The dashed line indicates the connection site.

[0054] It can be understood that any substitutable site in the ring penetrated by the dashed line can serve as the connection site.

[0055] In some embodiments, the chemical structural formula of the organic compound is selected from the structures represented by general formula (2):

[0056]

[0057] In some embodiments, Ar1 is selected from any one of a single bond, a phenylene group, and a phenylene group substituted by a phenyl group or a naphthyl group.

[0058] In some embodiments, Ar2 and A r3 are each independently selected from any one of the following groups:

[0059]

[0060]

[0061] wherein, * represents the connection site.

[0062] In some embodiments, is selected from any one of the following structures:

[0063]

[0064]

[0065] In some embodiments, the organic compound is selected from any one of the following compounds:

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076] It can be understood that the organic compounds to be protected in the embodiments of the present application are not limited to those listed above, and the hydrogen atoms in the organic compounds listed above can be substituted by any substituent group.

[0077] The organic compounds provided in the embodiments of the present application can be used as organic functional materials in organic electronic devices, especially in OLED devices. Organic functional materials can be divided into hole injection materials (HIM), hole transport materials (HTM), electron transport materials (ETM), electron injection materials (EIM), electron blocking materials (EBM), hole blocking materials (HBM), luminescent guest materials (Guest Emitter), and host materials (Host Emitter). Among them, the host materials can be divided into phosphorescent host materials, fluorescent host materials, and host materials for thermally activated delayed fluorescence (TADF) luminescent materials. The organic compounds represented by the general formula (1) provided in the embodiments of the present application can be any one of the above-listed organic functional materials.

[0078] In a preferred embodiment, the organic compound represented by the general formula (1) provided in the embodiments of the present application is a hole transport material.

[0079] In some embodiments, the glass transition temperature (Tg) of the organic compound represented by the general formula (1) provided in the embodiments of the present application is greater than or equal to 100 °C. In a preferred embodiment, 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.

[0080] The embodiments of the present application also provide a mixture, which includes at least one of the above-mentioned organic compounds represented by the general formula (1) and at least one organic functional material. The organic functional material is selected from at least one of a hole injection material, a hole transport material, an electron transport material, an electron injection material, an electron blocking material, a hole blocking material, an organic light-emitting guest material, an organic host material, and an inorganic quantum dot material. For example, various organic functional materials are described in detail in WO2010135519A1, US20090134784A1, and WO 2011110277A1. The entire contents of these three patent documents are hereby incorporated herein by reference. The organic functional material can be a small molecule or a polymer material.

[0081] In some embodiments, the organic functional material in the mixture is selected from an electron transport material and is blended with the organic compound represented by the general formula (1) and used as a co-host in an organic electronic device.

[0082] In some embodiments, the organic compound represented by the general formula (1) is applied to a vapor deposition type OLED device. Correspondingly, the molecular weight of the organic compound represented by the general formula (1) is less than or equal to 1100 g / mol, preferably less than or equal to 1000 g / mol, more preferably less than or equal to 950 g / mol, still more preferably less than or equal to 900 g / mol, and most preferably less than or equal to 800 g / mol.

[0083] In some embodiments, the organic compound represented by the general formula (1) is applied to a printed OLED device. Correspondingly, the molecular weight of the organic compound represented by the general formula (1) is greater than or equal to 700 g / mol, preferably greater than or equal to 900 g / mol, more preferably greater than or equal to 1000 g / mol, and most preferably greater than or equal to 1100 g / mol.

[0084] The embodiments of the present application also provide a composition, which includes at least one organic solvent and at least one of the above-mentioned organic compounds represented by the general formula (1), or the composition includes at least one organic solvent and the above-mentioned mixture.

[0085] The organic solvent can be selected from any one of aromatic or heteroaromatic, esters, aromatic ketones or aromatic ethers, aliphatic ketones or aliphatic ethers, alicyclic or olefinic compounds, or borate or phosphate compounds, or a mixture of two or more solvents. Preferably, the organic solvent is selected from aromatic or heteroaromatic-based solvents.

[0086] Examples of aromatic or heteroaromatic solvents suitable for this application include, but are not limited to: p - diisopropylbenzene, amylbenzene, tetralin, cyclohexylbenzene, chloronaphthalene, 1,4 - dimethylnaphthalene, 3 - isopropylbiphenyl, p - cymene, dipentylbenzene, tripentylbenzene, amyltoluene, 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, dimethylnaphthalene, 3 - isopropylbiphenyl, p - cymene, 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, α,α - dichlorodiphenylmethane, 4-(3 - phenylpropyl)pyridine, benzyl benzoate, 1,1 - bis(3,4 - dimethylphenyl)ethane, 2 - isopropylnaphthalene, quinoline, isoquinoline, methyl 2 - furan - carboxylate, ethyl 2 - furan - carboxylate, etc.

[0087] Examples of aromatic ketone solvents suitable for this application include, but are not limited to: 1 - tetralone, 2 - tetralone, 2-(phenyl epoxy)tetralone, 6 - (methoxy)tetralone, acetophenone, propiophenone, benzophenone and derivatives of these solvents such as 4 - methylacetophenone, 3 - methylacetophenone, 2 - methylacetophenone, 4 - methylpropiophenone, 3 - methylpropiophenone, 2 - methylpropiophenone, etc.

[0088] Examples of aromatic ether 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 - ethylbenzyl ethyl ether, 1,3 - dipropoxybenzene, 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, etc.

[0089] Examples of aliphatic ketone- or aliphatic ether-based solvents suitable for the present application include, but are not limited to: 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2,5-hexanedione, 2,6,8-trimethyl-4-nonanone, fenchone, phorone, isophorone, di-n-amyl ketone, 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.

[0090] Examples of borate- or phosphate-based solvents suitable for the present application include, but are not limited to: alkyl octanoates, alkyl sebacates, alkyl stearates, alkyl benzoates, alkyl phenylacetates, alkyl cinnamates, alkyl oxalates, alkyl maleates, alkanolactones, alkyl oleates, etc. Octyl octanoate, diethyl sebacate, diallyl phthalate, and isononyl isononanoate are particularly preferred.

[0091] In some embodiments, the composition further comprises at least one cosolvent. Examples of the cosolvent 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.

[0092] In some embodiments, solvents particularly suitable for the present application are solvents with Hansen solubility parameters in the following ranges: δd (dispersion force) in the range of 17.0 - 23.2 MPa 1 / 2 and particularly in the range of 18.5 - 21.0 MPa 1 / 2 ; δp (polar force) in the range of 0.2 - 12.5 MPa 1 / 2 and particularly in the range of 2.0 - 6.0 MPa 1 / 2 ; δh (hydrogen bonding force) in the range of 0.9 - 14.2 MPa 1 / 2 and particularly in the range of 2.0 - 6.0 MPa 1 / 2 and particularly in the range of 2.0 - 6.0 MPa.

[0093] In some embodiments, the boiling point parameter of the organic solvent in the composition needs to be considered when selecting it. In the embodiments of the present application, the boiling point of the organic solvent is greater than or equal to 150 °C; preferably, the boiling point of the organic solvent is greater than or equal to 180 °C; more preferably, the boiling point of the organic solvent is greater than or equal to 200 °C; still more preferably, the boiling point of the organic solvent is greater than or equal to 250 °C; most preferably, the boiling point of the organic solvent is greater than or equal to 275 °C or greater than or equal to 300 °C. The 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 the organic functional material.

[0094] In some embodiments, the composition provided by the embodiments of the present application is a solution.

[0095] In other embodiments, the composition provided by the embodiments of the present application is a suspension.

[0096] In some embodiments, the mass fraction range of the organic compound or the mixture in the composition is 0.01 wt% to 10 wt%. Preferably, in the composition, the mass fraction range of the organic compound or the mixture is 0.1 wt% to 15 wt%. More preferably, in the composition, the mass fraction range of the organic compound or the mixture is 0.2 wt% to 5 wt%. Most preferably, in the composition, the mass fraction range of the organic compound or the mixture is 0.25 wt% to 3 wt%.

[0097] In some embodiments, the mass fraction of the organic compound or the mixture 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%, 12% or 15%.

[0098] The embodiments of the present application also provide a use of the composition as a coating or printing ink in the preparation of organic electronic devices. A particularly preferred use is to use the composition as a coating or printing ink and prepare the organic electronic device 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, letterpress printing, screen printing, dip coating, spin coating, blade coating, roller printing, reverse roller printing, lithography, flexography, rotary printing, spraying, brushing or pad printing, slot die coating, etc. Gravure printing, nozzle printing and inkjet printing are preferred. The solution or suspension may additionally include one or more components such as surface active compounds, lubricants, wetting agents, dispersants, water repellents, adhesives, etc., for adjusting viscosity, film-forming properties, improving adhesion, etc. Regarding printing techniques and their related requirements for relevant solutions, such as solvents and concentrations, viscosities, etc.

[0100] The organic compound, the mixture or the composition provided by the present application can be applied to organic electronic devices. In the embodiments of the present application, it is preferred to apply the organic compound to the hole transport layer of an OLED device.

[0101] The organic electronic devices include but are 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, such as an OLED, an OLEEC or an OLEFET.

[0102] Such as Figure 1As shown, an organic electronic device 100 is further provided in an embodiment of the present application. The organic electronic device 100 includes a substrate 10, a first electrode 20, an organic functional layer 30, and a second electrode 90. The first electrode 20 is disposed on one side of the substrate 10, the organic functional layer 30 is disposed on the side of the first electrode 20 away from the substrate 10, and the second electrode 90 is disposed on the side of the organic functional layer 30 away from the first electrode 20. Among them, the material of the organic functional layer 30 includes at least one organic compound represented by the following general formula (1), or the material of the organic functional layer 30 includes the above-mentioned mixture, or the organic functional layer 30 is prepared from the above-mentioned composition.

[0103] In some embodiments, the organic functional layer 30 is selected from at least one of a hole injection layer (HIL), a hole transport layer (HTL), a light-emitting layer (EML), an electron blocking layer (EBL), an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0104] In some embodiments, the organic functional layer 30 includes a hole transport layer 50 and a light-emitting layer 60 which are stacked; the material of the hole transport layer 50 includes at least one organic compound represented by the following general formula (1), or the above-mentioned mixture, or the hole transport layer 50 is prepared from the above-mentioned composition.

[0105] In some embodiments, the organic functional layer 30 further includes a hole injection layer 40 disposed between the first electrode 20 and the hole transport layer 50, an electron transport layer 70 and an electron injection layer 80 disposed between the light-emitting layer 60 and the second electrode 90, but is not limited thereto.

[0106] In some embodiments, as Figure 2 shown, the hole transport layer 50 includes a first hole transport layer 50a and a second hole transport layer 50b which are stacked between the hole injection layer 40 and the light-emitting layer 60. The materials of the first hole transport layer 50a and the second hole transport layer 50b are different, and the material of the second hole transport layer 50b is selected from at least one organic compound represented by the following general formula (1), or the above-mentioned mixture, or the hole transport layer 50 is prepared from the above-mentioned composition.

[0107] In some embodiments, the material of the first hole transport layer 50a is selected from the compound shown as HT-1, but is not limited thereto.

[0108] In some embodiments, the first electrode 20 is an anode and the second electrode 70 is a cathode.

[0109] The anode may include a conductive metal, a metal oxide, or a conductive polymer. The anode can easily inject holes into the hole injection layer (HIL), the 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 lumophore in the light-emitting layer or the p-type semiconductor material serving as the HIL, HTL, or electron blocking layer (EBL) is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. 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 devices according to the present invention application.

[0110] The cathode may include a conductive metal or a metal oxide. The cathode can easily inject electrons into the EIL, 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 lumophore in the light-emitting layer or the 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 according to the present invention 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.

[0111] In some embodiments, the light-emitting material in the light-emitting layer 60 is selected from singlet emitters, triplet emitters, or TADF materials.

[0112] In some embodiments, the thickness range of the organic functional layer 30 is from 10 nm to 200 nm, preferably from 20 nm to 150 nm, more preferably from 30 nm to 100 nm, and most preferably from 40 nm to 90 nm.

[0113] In some embodiments, the organic electronic device 100 is selected from any one of an organic light-emitting diode (OLED), an organic photovoltaic cell (OPV), an organic light-emitting electrochemical cell (OLEEC), an organic field-effect transistor (OFET), an organic light-emitting field-effect transistor (OLEFET), an organic laser, an organic spintronic device, an organic sensor, and an organic plasmon-emitting diode (OPED). Particularly preferably, the organic electronic device 100 is selected from organic electroluminescent devices, such as any one of OLED, OLEEC, and an organic light-emitting field-effect transistor.

[0114] The organic light-emitting device 100 provided by the embodiments of the present application can be applied to various electronic devices, including but not limited to display devices, lighting devices, light sources, sensors, etc.

[0115] The embodiments of the present application further provide an electronic device, the electronic device includes the organic electronic device 100 provided by the embodiments of the present application, and the electronic device includes but not limited to display devices, lighting devices, light sources, sensors, and the like.

[0116] The embodiments of the present application further provide a display panel, and the display panel includes the above-mentioned organic light-emitting device 100.

[0117] 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 inventive concept of the present invention, those skilled in the art should be aware 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.

[0118] The organic compounds and their preparation methods of the present application will be further described in detail below in conjunction with specific embodiments, but the present application is not limited to the following embodiments. The raw materials used in the following embodiments are all commercially available products unless otherwise specified.

[0119] (1) Synthesis examples of organic compounds

[0120] Example 1

[0121] The synthesis route of organic compound C-1 is shown as follows:

[0122]

[0123] Synthesis of intermediate 1-3:

[0124] Intermediate 1-1 (10 mmol) and intermediate 1-2 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. Under a nitrogen (N2) 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, washed with water and separated by liquid separation. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 1-3. The molar amount of intermediate 1-3 was 7.63 mmol, the yield of intermediate 1-3 was 76.3%, and the MS (ASAP) of intermediate 1-3 = 270.

[0125] Synthesis of intermediate 1-4:

[0126] Intermediate 1-3 (10 mmol), phosphorus pentoxide (30 mmol) and 30 mL of trifluoromethanesulfonic acid were added to a 100 mL three-necked flask and stirred at room temperature for 24 h to end the reaction. The reaction solution was slowly poured into 300 mL of ice water and filtered by suction. The filter cake was washed several times with water, aqueous sodium bicarbonate solution and water successively. The filter cake was collected, dried and placed in 50 mL of pyridine, and refluxed for 12 h. After cooling to room temperature, it was extracted with dichloromethane three times. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 1-4. The molar amount of intermediate 1-4 was 7.57 mmol, the yield of intermediate 1-4 was 75.7%, and the MS (ASAP) of intermediate 1-4 = 268.

[0127] Synthesis of intermediate 1-5:

[0128] 10 mmol of intermediate 1-4 and 100 ml of dry toluene were added to a 250 ml three-necked flask. Under a N2 atmosphere, it was cooled to -30 °C, and a solution of n-BuLi in n-hexane (30.6 mmol) was added dropwise. The temperature was raised to 60 °C and reacted for 2 h, and the n-hexane solvent was removed by distillation under reduced pressure. The reaction solution was cooled to -30 °C again, 21 mol of iodine was added, and it was stirred at room temperature for 0.5 h. The reaction solution was cooled to room temperature. An aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction. The aqueous phase was extracted with ethyl acetate and the organic phases were combined. The solvent was removed by rotary evaporation to obtain a crude product, which was purified by flash silica gel column to obtain a pure product. It was recrystallized from toluene and ethyl acetate to obtain intermediate 1-5. The molar amount of intermediate 1-5 was 5.86 mmol, the yield of intermediate 1-5 was 58.6%, and the MS (ASAP) of intermediate 1-5 = 393.

[0129] Synthesis of organic compound C-1:

[0130] Intermediate 1-5 (10 mmol), Compound 1-6 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) 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 cooling, the solvent was removed by rotary evaporation, extracted and washed with water and separated by liquid separation, and the organic phase was purified by column chromatography to obtain organic compound C-1. The yield of organic compound C-1 was 87.6%, and the MS (ASAP) of organic compound C-1 = 663.

[0131] Example 2

[0132] The synthetic route of organic compound C-2 is as follows:

[0133]

[0134] Synthesis of intermediate 2-2:

[0135] Intermediate 1-5 (10 mmol) and intermediate 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 mmol) 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, then extracted and washed with water and separated by liquid separation, and the organic phase was purified by column chromatography and recrystallized to obtain intermediate 2-2. The molar amount of intermediate 2-2 was 8.33 mmol, the yield of intermediate 2-2 was 83.3%, and the MS (ASAP) of intermediate 2-2 = 422.

[0136] Synthesis of intermediate 2-4:

[0137] Intermediate 2-2 (10 mmol), Compound 2-3 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene. Under a nitrogen atmosphere, the reaction solution was heated to 100 °C and stirred for 6 h; after cooling, the solvent was removed by rotary evaporation, extracted and washed with water and separated by liquid separation, and the organic phase was purified by column chromatography to obtain intermediate 2-4. The molar amount of intermediate 2-4 was 7.76 mmol, the yield of intermediate 2-4 was 77.6%, and the MS (ASAP) of intermediate 2-4 = 511.

[0138] Synthesis of organic compound C-2:

[0139] Dissolve Compound 2-4 (10 mmol), Compound 2-5 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol) and sodium tert-butoxide (30 mmol) in toluene. Heat the reaction solution to 100 °C under a nitrogen atmosphere and stir for 6 h; after cooling, rotary evaporate to remove the solvent, extract and wash with water and separate the layers. The organic phase is purified by column chromatography to obtain organic compound C-2. The yield of organic compound C-2 is 69.8%, and the MS (ASAP) of organic compound C-2 = 677.

[0140] Example 3

[0141] [[ID=**6]]The synthetic route of organic compound C-3 is as follows:

[0142]

[0143] [[ID=**12]]Synthesis of intermediate 3-2:

[0144] [[ID=**15]]Dissolve intermediate 2-2 (10 mmol), Compound 3-1 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol) and sodium tert-butoxide (30 mmol) in toluene. Heat the reaction solution to 100 °C under a nitrogen atmosphere and stir for 6 h; after cooling, rotary evaporate to remove the solvent, extract and wash with water and separate the layers. The organic phase is purified by column chromatography to obtain intermediate 3-2. The molar amount of intermediate 3-2 is 8.07 mmol, the yield of intermediate 3-2 is 80.7%, and the MS (ASAP) of intermediate 3-2 = 517.

[0145] [[ID=**18]]Synthesis of organic compound C-3:

[0146] [[ID=**21]]Dissolve intermediate 3-2 (10 mmol), Compound 3-3 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol) and sodium tert-butoxide (30 mmol) in toluene. Heat the reaction solution to 100 °C under a nitrogen atmosphere and stir for 6 h; after cooling, rotary evaporate to remove the solvent, extract and wash with water and separate the layers. The organic phase is purified by column chromatography to obtain organic compound C-3. The yield of organic compound C-3 is 51.6%, and the MS (ASAP) of organic compound C-3 = 683.

[0147] [[ID=**24]]Example 4

[0148] [[ID=**27]]The synthetic route of organic compound C-4 is as follows:

[0149]

[0150] [[ID=**33]]Synthesis of organic compound C-4:

[0151] Intermediate 1-5 (10 mmol) and Compound 4-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) 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 cooling, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water and separated by liquid-liquid extraction. The organic phase was purified by column chromatography to obtain organic compound C-4. The yield of organic compound C-4 was 89.4%, and the MS (ASAP) of organic compound C-4 was 523.

[0152] Example 5

[0153] The synthetic route of Compound C-5 is as follows:

[0154]

[0155] Synthesis of Intermediate 5-2:

[0156] Intermediate 1-5 (10 mmol) and Intermediate 5-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) 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 cooled, most of the solvent was removed by rotary evaporation, and then the mixture was extracted and washed with water and separated by liquid-liquid extraction. The organic phase was purified by column chromatography and recrystallized to obtain Intermediate 5-2. The molar amount of Intermediate 5-2 was 7.84 mmol, the yield of Intermediate 5-2 was 78.4%, and the MS (ASAP) of Intermediate 5-2 was 547.

[0157] Synthesis of Intermediate 5-4:

[0158] Intermediate 5-2 (10 mmol) and Intermediate 5-3 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) 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 cooled, most of the solvent was removed by rotary evaporation, and then the mixture was extracted and washed with water and separated by liquid-liquid extraction. The organic phase was purified by column chromatography and recrystallized to obtain Intermediate 5-4. The molar amount of Intermediate 5-4 was 8.13 mmol, the yield of Intermediate 5-4 was 81.3%, and the MS (ASAP) of Intermediate 5-4 was 498.

[0159] Synthesis of Organic Compound C-5:

[0160] Intermediate 5-4 (10 mmol), compound 5-5 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene. The reaction solution was heated to 100 °C and stirred for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, extracted and washed with water for liquid separation, and the organic phase was subjected to column chromatography to obtain organic compound C-5. The yield of organic compound C-5 was 62.5%, and the MS(ASAP) of organic compound C-5 = 587.

[0161] Example 6

[0162] Synthetic route of organic compound C-6:

[0163]

[0164] Synthesis of intermediate 6-2:

[0165] Intermediate 1-5 (10 mmol) and intermediate 6-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) 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, then extracted and washed with water for liquid separation, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 6-2. The molar amount of intermediate 6-2 was 7.24 mmol, the yield of intermediate 6-2 was 72.4%, and the MS(ASAP) of intermediate 6-2 = 547.

[0166] Synthesis of intermediate 6-4:

[0167] Intermediate 6-2 (10 mmol) and compound 6-3 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) 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, then extracted and washed with water for liquid separation, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 6-4. The molar amount of intermediate 6-4 was 8.19 mmol, the yield of intermediate 6-4 was 81.9%, and the MS(ASAP) of intermediate 6-4 = 548.

[0168] Synthesis of organic compound C-6:

[0169] The intermediate 6-4 (10 mmol), compound 6-5 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene. The reaction solution was heated to 100 °C under a nitrogen atmosphere and stirred for 6 h; after cooling, the solvent was removed by rotary evaporation, extracted and washed with water and separated by liquid separation. The organic phase was purified by column chromatography to obtain organic compound C-6. The yield of organic compound C-6 was 80.3%, and the MS (ASAP) of organic compound C-6 = 789.

[0170] Example 7

[0171] The synthetic route of organic compound C-7 is as follows:

[0172]

[0173] Synthesis of organic compound C-7:

[0174] The intermediate 2-4 (10 mmol), compound 7-1 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene. The reaction solution was heated to 100 °C under a nitrogen atmosphere and stirred for 6 h; after cooling, the solvent was removed by rotary evaporation, extracted and washed with water and separated by liquid separation. The organic phase was purified by column chromatography to obtain organic compound C-7. The yield of organic compound C-7 was 85.1%, and the MS (ASAP) of organic compound C-7 = 713.

[0175] Example 8

[0176] The synthetic route of organic compound C-8 is as follows:

[0177]

[0178] Synthesis of intermediate 8-2:

[0179] The intermediate 2-2 (10 mmol), compound 8-1 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene. The reaction solution was heated to 100 °C under a nitrogen atmosphere and stirred for 6 h; after cooling, the solvent was removed by rotary evaporation, extracted and washed with water and separated by liquid separation. The organic phase was purified by column chromatography to obtain intermediate 8-2. The molar amount of intermediate 8-2 was 8.67 mmol, the yield of intermediate 8-2 was 86.7%, and the MS (ASAP) of intermediate 8-2 = 587.

[0180] Synthesis of organic compound C-8:

[0181] Intermediate 8-2 (10 mmol), compound 8-3 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene. The reaction solution was heated to 100 °C and stirred for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, extracted and washed with water for liquid separation. The organic phase was purified by column chromatography to obtain organic compound C-8. The yield of organic compound C-8 was 73.9%, and the MS (ASAP) of organic compound C-8 = 815.

[0182] Example 9

[0183] The synthetic route of organic compound C-9 is as follows:

[0184]

[0185] Synthesis of intermediate 9-2:

[0186] Intermediate 1-5 (10 mmol) and intermediate 9-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) 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, then extracted and washed with water for liquid separation. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 9-2. The molar amount of intermediate 9-2 was 7.48 mmol, the yield of intermediate 9-2 was 74.8%, and the MS (ASAP) of intermediate 9-2 = 422.

[0187] Synthesis of intermediate 9-4:

[0188] Intermediate 9-2 (10 mmol), compound 9-3 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene. The reaction solution was heated to 100 °C and stirred for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, extracted and washed with water for liquid separation. The organic phase was purified by column chromatography to obtain intermediate 9-4. The molar amount of intermediate 9-4 was 8.41 mmol, the yield of intermediate 9-4 was 84.1%, and the MS (ASAP) of intermediate 9-4 = 435.

[0189] Synthesis of organic compound C-9:

[0190] Intermediate 9-4 (10 mmol), compound 9-5 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene. The reaction solution was heated to 100 °C and stirred for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, extracted and washed with water and separated by liquid separation. The organic phase was purified by column chromatography to obtain organic compound C-9. The yield of organic compound C-9 was 69.4%, and the MS (ASAP) of organic compound C-9 = 587.

[0191] Example 10

[0192] The synthetic route of organic compound C-10 is as follows:

[0193]

[0194] Synthesis of intermediate 10-2:

[0195] Intermediate 1-5 (10 mmol) and intermediate 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 mmol) 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, then extracted and washed with water and separated by liquid separation. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 10-2. The molar amount of intermediate 10-2 was 6.38 mmol, the yield of intermediate 10-2 was 63.8%, and the MS (ASAP) of intermediate 10-2 = 422.

[0196] Synthesis of intermediate 10-4:

[0197] Intermediate 10-2 (10 mmol), compound 10-3 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene. The reaction solution was heated to 100 °C and stirred for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, extracted and washed with water and separated by liquid separation. The organic phase was purified by column chromatography to obtain intermediate 10-4. The molar amount was 8.68 mmol, the yield of intermediate 10-4 was 86.8%, and the MS (ASAP) of intermediate 10-4 = 511.

[0198] Synthesis of organic compound C-10:

[0199] Intermediate 10-4 (10 mmol), compound 10-5 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene. The reaction solution was heated to 100 °C and stirred for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, extracted and washed with water and separated by liquid separation. The organic phase was purified by column chromatography to obtain organic compound C-10. The yield of organic compound C-10 was 74.9%, and the MS(ASAP) of organic compound C-10 = 689.

[0200] Example 11

[0201] The synthetic route of organic compound C-11 is as follows:

[0202]

[0203] Synthesis of organic compound C-11:

[0204] Intermediate 10-2 (10 mmol), compound 11-1 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene. The reaction solution was heated to 100 °C and stirred for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, extracted and washed with water and separated by liquid separation. The organic phase was purified by column chromatography to obtain organic compound C-11. The yield of organic compound C-11 was 84.2%, and the MS(ASAP) of organic compound C-11 = 763.

[0205] Example 12

[0206] The synthetic route of organic compound C-12 is as follows:

[0207]

[0208] Synthesis of organic compound C-12:

[0209] Intermediate 5-4 (10 mmol), compound 12-1 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene. The reaction solution was heated to 100 °C and stirred for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, extracted and washed with water and separated by liquid separation. The organic phase was purified by column chromatography to obtain organic compound C-12. The yield of organic compound C-12 was 78.4%, and the MS(ASAP) of organic compound C-(-12) = 939.

[0210] Example 13

[0211] The synthetic route of organic compound C-13 is as follows:

[0212]

[0213] Synthesis of Intermediate 13-2:

[0214] Dissolve Intermediate 5-4 (10 mmol), Compound 13-1 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol) and sodium tert-butoxide (30 mmol) in toluene. Heat the reaction solution to 100 °C under a nitrogen atmosphere and stir for 6 h; after cooling, rotary evaporate to remove the solvent, extract and wash with water and separate the layers. The organic phase is purified by column chromatography to obtain Intermediate 13-2. The molar amount of Intermediate 13-2 is 7.88 mmol, the yield of Intermediate 13-2 is 78.8%, and the MS (ASAP) of Intermediate 13-2 = 587.

[0215] Synthesis of Organic Compound C-13:

[0216] Dissolve Intermediate 13-2 (10 mmol), Compound 13-3 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol) and sodium tert-butoxide (30 mmol) in toluene. Heat the reaction solution to 100 °C under a nitrogen atmosphere and stir for 6 h; after cooling, rotary evaporate to remove the solvent, extract and wash with water and separate the layers. The organic phase is purified by column chromatography to obtain Organic Compound C-13. The yield of Organic Compound C-13 is 69.1%, and the MS (ASAP) of Organic Compound C-13 = 839.

[0217] Example 14

[0218] The synthetic route of Organic Compound C-14 is as follows:

[0219]

[0220] Synthesis of Organic Compound C-14:

[0221] Dissolve Intermediate 5-4 (10 mmol), Compound 14-1 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol) and sodium tert-butoxide (30 mmol) in toluene. Heat the reaction solution to 100 °C under a nitrogen atmosphere and stir for 6 h; after cooling, rotary evaporate to remove the solvent, extract and wash with water and separate the layers. The organic phase is purified by column chromatography to obtain Organic Compound C-14. The yield of Organic Compound C-14 is 82.4%, and the MS (ASAP) of Organic Compound C-14 = 903.

[0222] Example 15

[0223] The synthetic route of Organic Compound C-15 is as follows:

[0224]

[0225] Synthesis of Intermediate 15-2:

[0226] Dissolve Intermediate 5-2 (10 mmol) and Intermediate 15-1 (10 mmol) in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and add Pd(PPh3)4 (0.1 mmol) 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 15-2. The molar amount of Intermediate 15-2 is 7.58 mmol, the yield of Intermediate 15-2 is 75.8%, and the MS (ASAP) of Intermediate 15-2 = 548.

[0227] Synthesis of Intermediate 15-4:

[0228] Dissolve Intermediate 15-2 (10 mmol), Compound 15-3 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol) and sodium tert-butoxide (30 mmol) in toluene. Under a nitrogen atmosphere, heat the reaction solution to 100 °C and stir for 6 h; after cooling, rotary evaporate to remove the solvent, extract and wash with water and separate the liquid. The organic phase is subjected to column chromatography to obtain Intermediate 15-4. The molar amount of Intermediate 15-4 is 7.17 mmol, the yield of Intermediate 15-4 is 71.7%, and the MS (ASAP) of Intermediate 15-4 = 637.

[0229] Synthesis of Organic Compound C-15:

[0230] Dissolve Intermediate 15-4 (10 mmol), Compound 15-5 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol) and sodium tert-butoxide (30 mmol) in toluene. Under a nitrogen atmosphere, heat the reaction solution to 100 °C and stir for 6 h; after cooling, rotary evaporate to remove the solvent, extract and wash with water and separate the liquid. The organic phase is subjected to column chromatography to obtain Organic Compound C-15. The yield of Organic Compound C-15 is 67.3%, and the MS (ASAP) of Organic Compound C-15 = 803.

[0231] Example 16

[0232] The synthesis route of Organic Compound C-16 is as follows:

[0233]

[0234] Synthesis of Intermediate 16-2:

[0235] Intermediate 5-2 (10 mmol) and intermediate 16-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) 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 16-2. The molar amount of intermediate 16-2 was 6.87 mmol, the yield of intermediate 16-2 was 68.7%, and the MS (ASAP) of intermediate 16-2 was 548.

[0236] Synthesis of intermediate 16-4:

[0237] Intermediate 16-2 (10 mmol), compound 16-3 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene. Under a nitrogen atmosphere, the reaction solution was heated to 100 °C and stirred for 6 h. After cooling, the solvent was removed by rotary evaporation, and extraction and washing with water were carried out for liquid separation. The organic phase was subjected to column chromatography to obtain intermediate 16-4. The molar amount of intermediate 16-4 was 7.36 mmol, the yield of intermediate 16-4 was 73.6%, and the MS (ASAP) of intermediate 16-4 was 637.

[0238] Synthesis of organic compound C-16:

[0239] Intermediate 16-4 (10 mmol), compound 16-5 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene. Under a nitrogen atmosphere, the reaction solution was heated to 100 °C and stirred for 6 h. After cooling, the solvent was removed by rotary evaporation, and extraction and washing with water were carried out for liquid separation. The organic phase was subjected to column chromatography to obtain organic compound C-16. The yield of organic compound C-16 was 70.9%, and the MS (ASAP) of organic compound C-16 was 865.

[0240] Example 17

[0241] The synthetic route of organic compound C-17 is as follows:

[0242]

[0243] Synthesis of organic compound C-17:

[0244] Intermediate 1-5 (10 mmol), Compound 17-1 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene. The reaction solution was heated to 100 °C and stirred for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, extracted and washed with water and separated by liquid separation. The organic phase was purified by column chromatography to obtain organic compound C-17. The yield of organic compound C-17 was 90.6%, and the MS (ASAP) of organic compound C-17 = 435.

[0245] Example 18

[0246] The synthetic route of organic compound C-18 is as follows:

[0247]

[0248] Synthesis of intermediate 18-2:

[0249] Intermediate 1-1 (10 mmol) and intermediate 18-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) 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, then extracted and washed with water and separated by liquid separation. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 18-2. The molar amount of intermediate 18-2 was 7.33 mmol, the yield of intermediate 18-2 was 73.3%, and the MS (ASAP) of intermediate 18-2 = 304.

[0250] Synthesis of intermediate 18-3:

[0251] Intermediate 18-2 (10 mmol), phosphorus pentoxide (30 mmol) and 30 mL of trifluoromethanesulfonic acid were added to a 100 mL three-necked flask and stirred at room temperature for 24 h to end the reaction. The reaction solution was slowly poured into 300 mL of ice water and filtered by suction. The filter cake was washed several times with water, aqueous sodium bicarbonate solution, and water successively. The filter cake was collected, dried and placed in 50 mL of pyridine and refluxed for 12 h. After cooling to room temperature, it was extracted 3 times with dichloromethane. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 18-3. The molar amount of intermediate 18-3 was 7.07 mmol, the yield of intermediate 18-3 was 70.7%, and the MS (ASAP) of intermediate 18-3 = 302.

[0252] Synthesis of organic compound C-18:

[0253] Intermediate 18-3 (10 mmol), Compound 17-1 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene. The reaction solution was heated to 100 °C and stirred for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, extracted and washed with water and separated by liquid separation. The organic phase was purified by column chromatography to obtain organic compound C-18. The yield of organic compound C-18 was 91.2%, and the MS (ASAP) of organic compound C-18 = 435.

[0254] Example 19

[0255] The synthetic route of organic compound C-19 is as follows:

[0256]

[0257] Synthesis of intermediate 19-2:

[0258] Intermediate 1-1 (10 mmol) and intermediate 19-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) 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, then extracted and washed with water and separated by liquid separation. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 19-2. The molar amount of intermediate 19-2 was 7.89 mmol, the yield of intermediate 19-2 was 78.9%, and the MS (ASAP) of intermediate 19-2 = 304.

[0259] Synthesis of intermediate 19-3:

[0260] Intermediate 19-2 (10 mmol), phosphorus pentoxide (30 mmol) and 30 mL of trifluoromethanesulfonic acid were added to a 100 mL three-necked flask and stirred at room temperature for 24 h to end the reaction. The reaction solution was slowly poured into 300 mL of ice water and filtered by suction. The filter cake was washed several times with water, aqueous sodium bicarbonate solution and water successively. The filter cake was collected, dried and placed in 50 mL of pyridine, and refluxed for 12 h. After cooling to room temperature, it was extracted 3 times with dichloromethane. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 19-3. The molar amount of intermediate 19-3 was 7.67 mmol, the yield of intermediate 19-3 was 76.7%, and the MS (ASAP) of intermediate 19-3 = 302.

[0261] Synthesis of organic compound C-19:

[0262] Intermediate 19-3 (10 mmol), Compound 17-1 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene. The reaction solution was heated to 100 °C and stirred for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, extracted and washed with water for liquid separation, and the organic phase was purified by column chromatography to obtain organic compound C-19. The yield of organic compound C-19 was 89.5%, and the MS (ASAP) of organic compound C-19 was 435.

[0263] Example 20

[0264] The synthetic route of organic compound C-20 is as follows:

[0265]

[0266] Synthesis of intermediate 20-2:

[0267] Intermediate 1-1 (10 mmol) and intermediate 20-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) 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, then extracted and washed with water for liquid separation, and the organic phase was purified by column chromatography and recrystallized to obtain intermediate 20-2. The molar amount of intermediate 20-2 was 8.34 mmol, the yield of intermediate 20-2 was 83.4%, and the MS (ASAP) of intermediate20-2 was 304.

[0268] Synthesis of intermediate 20-3:

[0269] Intermediate 20-2 (10 mmol), phosphorus pentoxide (30 mmol) and 30 mL of trifluoromethanesulfonic acid were added to a 100 mL three-necked flask and stirred at room temperature for 24 h to end the reaction. The reaction solution was slowly poured into 300 mL of ice water and filtered by suction. The filter cake was washed several times with water, aqueous sodium bicarbonate solution, and water successively. The filter cake was collected, dried and placed in 50 mL of pyridine, and refluxed for 12 h. After cooling to room temperature, it was extracted 3 times with dichloromethane. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 20-3. The molar amount of intermediate 20-3 was 7.68 mmol, the yield of intermediate 20-3 was 76.8%, and the MS (ASAP) of intermediate 20-3 was 302.

[0270] Synthesis of organic compound C-20:

[0271] Intermediate 20-3 (10 mmol), compound 17-1 (10 mmol), Pd(dba)2 (0.1 mmol), TTBP (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene. The reaction solution was heated to 100 °C and stirred for 6 h under a nitrogen atmosphere; after cooling, the solvent was removed by rotary evaporation, extracted and washed with water and separated by liquid separation. The organic phase was purified by column chromatography to obtain organic compound C-20. The yield of organic compound C-20 was 91.8%, and the MS (ASAP) of organic compound C-20 = 435.

[0272] Comparative Example

[0273] The present application also provides five comparative example compounds, denoted by comparative example compounds Ref-1 to Ref-5 respectively, and their chemical structural formulas are shown as follows:

[0274]

[0275] (II) Energy level calculation of organic compounds

[0276] The energy levels of organic compound materials can be obtained by quantum calculation. For example, using TD-DFT (time-dependent density functional theory) through Gaussian09W (Gaussian Inc.), and the specific simulation method can be referred to WO2011141110. First, the molecular geometry structure is optimized by the semi-empirical method "Ground State / Semi-empirical / Default Spin / AM1" (Charge 0 / Spin Singlet), and then the energy structure of the organic molecule is calculated by the TD-DFT (time-dependent density functional theory) method "TD-SCF / DFT / Default Spin / B3PW91" and the basis set "6-31G(d)" (Charge 0 / Spin Singlet). The HOMO and LUMO energy levels are calculated according to the following calibration formula, and S1, T1 and the harmonic factor f(S1) are directly used.

[0277] HOMO (eV) = ((HOMO(G) × 27.212) - 0.9899) / 1.1206;

[0278] LUMO (eV) = ((LUMO(G) × 27.212) - 2.0041) / 1.385;

[0279] Among them, HOMO(G) and LUMO(G) are the direct calculation results of Gaussian 09W, with the unit of Hartree. The calculation results of the HOMO energy level, LUMO energy level, T1 energy level, and S1 energy level of the organic compounds C-1 to C-20 and the comparative compounds Ref-1 to Ref-5 provided in Examples 1 to 20 of the present application are shown in Table 1.

[0280] Table 1

[0281]

[0282]

[0283] As can be seen from Table 1, the T1 energy level (E T1 ) and S1 energy level (E S1 ) of the organic compounds C-1 to C-20 provided in Examples 1 to 20 of the present application are slightly higher than the T1 energy level (E T1 ) and S1 energy level (E S1 ) of the comparative compounds Ref-1 to Ref-5. In particular, the T1 energy level (E T1 ) and S1 energy level (E S1 ) of the comparative compound Ref-5 are significantly lower than the T1 energy level (E T1 ) and S1 energy level (E S1 ) of the organic compounds C-1 to C-20 by about 0.2 eV, indicating that the hole transport ability of the organic compounds C-1 to C-20 provided in Examples 1 to 20 of the present application is stronger than that of the comparative compounds Ref-1 to Ref-5.

[0284] (III) Preparation and Characterization of OLED Devices

[0285] The following specifically describes the preparation process of OLED devices using the organic compounds C-1 to C-20 and the comparative compounds Ref-1 to Ref-5. The structure of the OLED device can refer to Figure 2 the organic electronic device shown.

[0286] Specifically, the structure of the OLED device is: ITO / HIL(10nm) / HT-1(60nm) / HT-2(60nm) / BH:BD(25nm) / ET:Liq(30nm) / Liq(1nm) / Al(100nm).

[0287] The OLED device using the organic compound C-1 as the hole transport material is denoted as OLED-1, and the preparation steps of the OLED-1 device are as described in a to c.

[0288] a. Cleaning of the conductive glass substrate: Clean it with chloroform, ketone, and isopropyl alcohol, and then perform ultraviolet ozone plasma treatment.

[0289] b. Preparation of the organic functional layer and the cathode: Transfer the ITO substrate into a vacuum vapor deposition device. Under high vacuum (1×10 -6 mbar), use resistance heating evaporation to deposit HATCN to form a 10-nm hole injection layer (HIL); then sequentially deposit to obtain a 60-nm first hole transport layer (HT-1) and a 60-nm second hole transport layer (HT-2, made of organic compound C-1); subsequently, co-deposit BH and BD in a weight ratio of 97:3 to form a 25-nm light-emitting layer; then, place ET and LiQ in different evaporation units and co-deposit them at a ratio of 50 wt% each to form a 30-nm electron transport layer on the light-emitting layer; subsequently, deposit 1 nm of LiQ as an electron injection layer on the electron transport layer, and finally deposit an Al cathode with a thickness of 100 nm on the electron injection layer.

[0290] c. Encapsulation: Encapsulate the device with ultraviolet curable resin in a nitrogen glove box to form the OLED-1 device.

[0291] The structures of the compounds involved in the preparation process of the OLED device are as follows:

[0292]

[0293] The preparation processes of other OLED devices are the same as that of the OLED-1 device, except that the material of the second hole transport layer is replaced with organic compounds C-2 to C-20 and comparative compounds Ref-1 to Ref-5 in Table 2, and the resulting devices are OLED-2 to OLED-20 and OLED-Ref1 to OLED-Ref5, respectively.

[0294] The current-voltage (J-V) characteristics of each OLED device are characterized by a characterization device, and important parameters such as voltage, lifetime, and external quantum efficiency are recorded simultaneously. The results are shown in Table 2. Among them, the lifetime LT95 is the time when the brightness drops to 95% of the initial brightness @1000 nits under a constant current. LT95 and the external quantum efficiency in Table 2 are calculated relative to the comparative device OLED-Ref1, that is, taking the lifetime of the comparative device OLED-Ref1 as 1 and the external quantum efficiency as 100% as a reference.

[0295] Table 2

[0296]

[0297]

[0298] As can be seen from Table 2, compared with the comparative devices OLED-Ref1 to OLED-Ref5, by using the organic compounds C-1 to C-20 provided in Examples 1 to 20 as the materials for the second hole transport layer (HT-2), the external quantum efficiency and lifetime of the resulting OLED-1 to OLED-20 devices are significantly improved.

[0299] The reason why the external quantum efficiency and lifetime of the OLED-1 to OLED-20 devices are significantly higher than those of the comparative devices OLED-Ref1 to OLED-Ref5 is that: a direct connection between the diarylamine and the phenanthrobenzo[f]furan group or the introduction of a substituted or unsubstituted phenyl group for connection results in a significant change in the molecular spatial structure of the organic compounds C-1 to C-20 relative to the molecules of the comparative compounds Ref-1 to Ref-5, thereby improving the molecular packing, making the molecules have greater rigidity, while increasing the glass transition temperature of the molecules, and increasing the luminous efficiency, stability and lifetime of the OLED device.

[0300] The reason why the external quantum efficiency and lifetime of the OLED-1 to OLED-20 devices are significantly higher than those of the comparative device OLED-Ref5 is that: introducing 1 phenanthrobenzo[f]furan group can increase the efficiency, stability and lifetime of the device more than introducing 2 phenanthrobenzo[f]furan groups, because introducing 2 benzo[def]phenanthro[f]furan groups will cause passivation of the molecular structure, and at the same time, too large a molecular weight is not conducive to hole transport, resulting in a decrease in the efficiency, stability and lifetime of the comparative device OLED-Ref5.

[0301] As can be seen from the above, the organic compounds provided in the embodiments of the present application as hole transport materials are significantly superior to the comparative compounds as hole transport materials. It can be seen that the luminous efficiency and lifetime of the OLED devices prepared by using the organic compounds of the embodiments of the present application are both significantly improved.

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

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

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

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

Claims

1. An organic compound, characterized in that, The chemical structural formula of the organic compound is selected from any one of the structures represented by the general formula (1): wherein, Ar1 is selected from a single bond or any one of the following groups: Ar2 and A r3 Any one or a combination of more than one selected from the following groups: X is selected from N or CR3; Y is selected from O, S, NR4 or CR5R6; Each occurrence of R3 - R6 is independently selected from a hydrogen atom, a deuterium atom, a linear alkyl group having 1 to 20 C atoms, a branched alkyl group having 3 to 20 C atoms, a cyclic alkyl group having 3 to 20 C atoms, a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, or any one or a combination of more than one of these; The dashed line indicates the connection site.

2. The organic compound according to claim 1, wherein The chemical structural formula of the organic compound is selected from the structure represented by the general formula (2):

3. The organic compound according to claim 1 or 2, characterized in that, Ar2 and A r3 Any one selected from the following groups: wherein, * represents the connection site.

4. The organic compound according to claim 1 or 2, characterized in that, Selected from any one of the following structures: wherein, * represents the connection site.

5. The organic compound according to claim 1, characterized in that, The organic compound is selected from any one of the following compounds:

6. A mixture, characterized in that, The mixture includes at least one organic compound as described in any one of claims 1 to 5, and at least one organic functional material; the organic functional material is selected from at least one of a hole injection material, a hole transport material, an electron transport material, an electron injection material, an electron blocking material, a hole blocking material, an organic light - emitting guest material, an organic host material, and an inorganic quantum dot material.

7. A composition, characterized in that, The composition includes at least one organic solvent and at least one organic compound as described in any one of claims 1 to 5, or the composition includes at least one of the organic solvents and the mixture as described in claim 6.

8. An organic electronic device, characterized in that, The organic electronic device includes: A first electrode; An organic functional layer disposed on one side of the first electrode; A second electrode disposed on the side of the organic functional layer away from the first electrode; wherein, the material of the organic functional layer includes at least one organic compound as described in any one of claims 1 to 5, or the material of the organic functional layer includes the mixture as described in claim 6, or the organic functional layer is prepared from the composition as described in claim 7.

9. The organic electronic device according to claim 8, wherein The organic functional layer includes a hole transport layer and a light - emitting layer stacked, and the hole transport layer is located between the first electrode and the light - emitting layer; the material of the hole transport layer includes at least one of the organic compounds.

10. A display panel, characterized in that, The display panel includes the organic electronic device as described in claim 8 or 9.

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