Arylamine organic compound, mixture, composition and organic electronic device

Abstract

The invention discloses an arylamine organic compound, a mixture, a composition and an organic electronic device. The arylamine organic compound is an organic conjugated molecule taking an arylamine group as a core, and two fluorene groups are connected through substituted or unsubstituted phenyl, so that effective extension of a pi conjugated system and remarkable optimization of a molecular accumulation mode are realized. The 2 # site of the fluorenyl is connected with arylamine, and the expansion of the fluorenyl is beneficial to the effective extension of a pi conjugated system, so that the excited state energy level of the material is improved, and the material can effectively prevent the reverse transmission of electrons and improve the luminous efficiency when being used as a luminous auxiliary material. Meanwhile, the optimization of the molecular accumulation mode not only facilitates the improvement of the transmission efficiency of current carriers, but also can promote the enhancement of the local rigidity of the material, facilitates the improvement of the thermal stability of the material, and ensures the long-acting operation of the material as a light-emitting auxiliary material in a device.

Description

Technical Field

[0001] This application relates to the technical field of compounds, and particularly to an aromatic amine organic compound, a mixture, a composition, and an organic electronic device. Background Art

[0002] Organic electroluminescence is a physical phenomenon that directly converts electrical energy into light energy, which depends on the optoelectronic properties of organic materials. An organic electroluminescent device based on this phenomenon usually consists of a positive electrode, a negative electrode, and multiple organic functional layers sandwiched therebetween. These functional layers include a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc., and each layer contains specific organic substances to optimize the performance of the device. In these devices, when a voltage is applied between the two electrodes, the positive electrode injects holes into the organic functional layer, while the negative electrode injects electrons. These injected holes and electrons meet to form excitons, and the excitons release light energy during the process of returning to the ground state. Organic electroluminescent devices have attracted attention due to their self-luminous characteristics, high brightness, high efficiency, low driving voltage, wide viewing angle, and high contrast. Organic light-emitting diodes (OLEDs) are typical representatives among them. OLEDs have demonstrated their unique advantages in the field of optoelectronic devices, such as flat panel displays and lighting devices, including wide viewing angles, fast response times, low operating voltages, and ultra-thin panel designs. These characteristics indicate that OLED technology has great potential and broad application prospects in future development.

[0003] In terms of improving the luminous efficiency and extending the service life of organic electroluminescent (OLED) elements, the selection and design of light-emitting auxiliary materials play a crucial role. Through carefully designed light-emitting auxiliary materials, the balanced carrier transport in OLED devices can be achieved, effectively curbing the reverse migration of electrons. This promotes the recombination of electrons and holes mainly in the central region of the light-emitting layer, thus significantly reducing the non-radiative recombination (quenching) of excitons, and further greatly improving the luminous efficiency and extending the service life of the device. Therefore, how to design new light-emitting auxiliary materials with more excellent performance to further adjust the transport balance of holes and electrons inside the device is the key to improving the device efficiency and life. This challenge has always been a difficult problem that scientific researchers in this field urgently need to overcome. Summary of the Invention

[0004] In view of this, this application provides an aromatic amine organic compound, a mixture, a composition, and an organic electronic device, aiming to improve the problem of unbalanced hole and electron transport inside the existing device.

[0005] The embodiment of this application is implemented as follows. According to the first aspect of this application, an aromatic amine organic compound is provided, and the aromatic amine organic compound includes a structural formula as shown in formula (1):

[0006]

[0007] Among them,

[0008] R 1 and R 2 each time they appear, are independently selected from one of a hydrogen atom, a deuterium atom, a methyl group, a tert-butyl group, a phenyl group, a biphenyl group, a naphthyl group, a fluorenyl group, a dibenzofuranyl group, and a dibenzothiophenyl group;

[0009] Ar 1 and Ar 2 are the same as or different from each other and are independently selected from one of the following groups:

[0010]

[0011] Among them,

[0012] Y is selected from O, S, and CR 3 R 4 ;

[0013] R 3 and R 4 each time they appear, are independently selected from an alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aromatic group having 5 to 16 ring atoms;

[0014] R 5 -R 16 each time they appear, are independently selected from one of a hydrogen atom, a deuterium atom, a methyl group, a tert-butyl group, a phenyl group, a biphenyl group, a naphthyl group, a fluorenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and a carbazolyl group;

[0015] The structure crossed by “—” indicates the connection site at any bond-forming position on this structure, and “*” indicates the connection site.

[0016] Optionally, in some embodiments of the present application, the general formula (1) is selected from any one of formulas (2-1) to (2-3):

[0017]

[0018] Optionally, in some embodiments of the present application, the organic compound is selected from the following structures:

[0019]

[0020]

[0021]

[0022]

[0023]

[0024]

[0025]

[0026] Optionally, in some embodiments of the present application, the glass transition temperature of the arylamine organic compound is greater than or equal to 100 °C; preferably, the glass transition temperature of the arylamine organic compound is greater than or equal to 160 °C.

[0027] Optionally, in some embodiments of the present application, the molar mass of the arylamine organic compound is greater than or equal to 600 g / mol; and / or

[0028] the molar mass of the arylamine organic compound is less than or equal to 1100 g / mol.

[0029] According to a second aspect of the present application, there is provided a mixture comprising at least one of the foregoing organic compounds and at least one organic functional material selected from at least one of a hole injection material, a hole transport material, a light-emitting auxiliary material, an electron transport material, an electron injection material, an electron blocking material, a hole blocking material, an organic light-emitting guest material, and an organic host material.

[0030] According to a third aspect of the present application, there is provided a composition comprising at least one of the foregoing arylamine organic compounds or the foregoing mixture and at least one organic solvent.

[0031] According to a fourth aspect of the present application, there is provided an organic electronic device comprising a light-emitting auxiliary material, the light-emitting auxiliary material comprising at least one of the foregoing arylamine organic compounds, or the foregoing mixture, or prepared from the foregoing composition.

[0032] The embodiment of the present application provides an aromatic amine-based organic compound, which is an organic conjugated molecule with an aromatic amine group as the core. By connecting two fluorene groups via a substituted or unsubstituted phenyl group, the effective extension of the π-conjugated system and the significant optimization of the molecular packing mode are realized. The connection of the aromatic amine at the 2-position of the fluorene group and the expansion of the fluorene group are both beneficial to the effective extension of the π-conjugated system, which helps to improve the excited state energy level of the material, enabling the material to effectively prevent the reverse transmission of electrons when used as a light-emitting auxiliary material and improving the light-emitting efficiency. At the same time, the optimization of the molecular packing mode is not only beneficial to the improvement of the carrier transport efficiency, but also promotes the enhancement of the local rigidity of the material, which is beneficial to improving its thermal stability and ensuring its long-term operation in the device when used as a light-emitting auxiliary material. In summary, the compound according to at least one exemplary embodiment of the present invention can improve the efficiency of the organic light-emitting device, especially when used as a light-emitting auxiliary material, it can achieve high light-emitting efficiency and improve the device life. BRIEF DESCRIPTION OF THE DRAWINGS

[0033] In order to more clearly illustrate the technical solutions in the embodiments of the present application, the following will briefly introduce the drawings required for the description of the embodiments. Obviously, the following drawings are only some embodiments of the present application. For those skilled in the art, without creative efforts, other drawings can be obtained based on these drawings.

[0034] Figure 1 It is a schematic structural diagram of an organic electronic device provided by the embodiment of the present application.

[0035] Reference numerals: 100, organic electronic device; 110, anode; 120, cathode; 130, organic functional layer. DETAILED DESCRIPTION OF THE EMBODIMENTS

[0036] The following further details the technical solutions of the present invention in conjunction with specific embodiments. The present invention can be implemented in many different forms and is not limited to the embodiments described herein. On the contrary, the purpose of providing these embodiments is to make the understanding of the disclosed content of the present invention more thorough and comprehensive.

[0037] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by those skilled in the art.

[0038] The term "and / or" used herein includes any and all combinations of one or more of the related listed items.

[0039] In the present invention, "substituted" means that the hydrogen atom in the substituent is replaced by the substituent.

[0040] In the present invention, "substituted or unsubstituted" means that the defined group may be substituted or may not be substituted. When the defined group is substituted, it should be understood that it is optionally substituted by a group acceptable in the art, including but not limited to: deuterium atom, cyano group, isocyano group, nitro group, halogen atom, C 1-10 alkyl of 1-10 alkoxy of 1-10 alkylthio of 6-30 aryl of 6-30 aryloxy of 6-30 arylthio of 3-30 heteroaryl, C 1-30 silyl, C 2-10 alkylamino of 6-30 arylamino, or a combination of the above groups, etc.

[0041] In the present invention, "the number of ring atoms" means the number of atoms among the atoms constituting the ring itself of a structural compound obtained by bonding atoms in a ring (for example, monocyclic compound, fused-ring compound, crosslinked 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 number of ring atoms" described below under the condition of no special description. For example, the number of ring atoms of a benzene ring is 6, the number of ring atoms of a naphthalene ring is 10, and the number of ring atoms of a thiophenyl group is 5.

[0042] In the present invention, "alkyl" may represent linear, branched and / or cyclic alkyl. The number of carbon atoms of the alkyl may be 1 to 20, and more preferably 1 to 10. A phrase containing this term, for example, "C 1-9 alkyl" refers to an alkyl containing 1 to 9 carbon atoms, and each occurrence may independently be C 1 alkyl, C 2 alkyl, C 3 alkyl, C 4 alkyl, C 5 alkyl, C 6 alkyl, C 7 alkyl, C 8 alkyl or C 9 alkyl. Non-limiting examples of the alkyl 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.

[0043] "Aryl or aromatic group" refers to 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 species, at least one is an aromatic ring system. For example, "substituted or unsubstituted aryl group having 5 to 16 ring atoms" refers to an aryl group containing 5 to 16 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, benzophenanthrene, dibenzo[a,h]anthracene, tetracene, pyrene, benzopyrene, 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.

[0044] In the present invention, "*" connected to a single bond represents a connection or fusion site.

[0045] In the present invention, when the connection site is not specified in a group, it means that any optional connection site in the group can be used as the connection site;

[0046] In the present invention, 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.

[0047] The present invention provides an aromatic amine organic compound, which can include a structural formula such as formula (1):

[0048]

[0049] Wherein,

[0050] R 1 and R 2 Each occurrence is independently selected from one of a hydrogen atom, a deuterium atom, a methyl group, a tert-butyl group, a phenyl group, a biphenylyl group, a naphthyl group, a fluorenyl group, a dibenzofuranyl group, and a dibenzothiophenyl group;

[0051] Ar 1 and Ar 2 Are the same as or different from each other and are independently selected from one of the following groups:

[0052]

[0053] Wherein,

[0054] Y is selected from O, S, and CR 3 R 4 ;

[0055] R 3 and R 4Each occurrence is independently selected from an alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aromatic group having 5 to 16 ring atoms;

[0056] R 5 -R 16 Each occurrence is independently selected from a hydrogen atom, a deuterium atom, a methyl group, a tert-butyl group, a phenyl group, a biphenyl group, a naphthyl group, a fluorene group, a dibenzofuran group, a dibenzothiophene group, and a carbazole group;

[0057] The structure marked with “—” indicates the bonding site at any position on this structure that can form a bond, and “*” indicates the bonding site.

[0058] By adopting the above scheme, R 1 and R 2 are preferably selected from a hydrogen atom, a deuterium atom, a methyl group, a tert-butyl group, a phenyl group, a biphenyl group, a naphthyl group, a fluorene group, a dibenzofuran group, and a dibenzothiophene group. These groups can effectively achieve better regulation of the excited state energy level and molecular packing of the compounds in this proposal, thereby obtaining excellent device luminescence efficiency and lifetime.

[0059] In some embodiments of this application, the general formula (1) can be selected from any one of formulas (2-1) to (2-3):

[0060]

[0061] By adopting the above scheme, refining the bonding site or position is particularly important for the performance regulation of organic light-emitting materials. Formulas (2-1) to (2-3) refine the bonding positions of two fluorene groups and the benzene ring. The regulation of the position can change the electronic structure and molecular packing of the compound, which helps to improve the luminescence efficiency and lifetime of the device.

[0062] In some embodiments of this application, the organic compound can be selected from the following structures:

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070] It should be noted that the hydrogen atoms in the above organic compounds can be further substituted by any group.

[0071] By adopting the above scheme, the above organic compounds are preferably obtained through theoretical calculation of important properties such as their energy levels, excited state energy levels, glass transition temperatures, etc. and device experiments, which helps to improve the efficiency and lifespan of organic electronic devices and has great potential.

[0072] The arylamine organic compounds according to the present invention can be used as 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), luminescence assisting materials (Prime), 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 (Thermally Activated Delayed Fluorescence, abbreviated as TADF). The organic compounds according to the present invention can be any one of them.

[0073] In some embodiments of the present application, the arylamine organic compounds can be used as luminescence assisting materials.

[0074] In some embodiments of the present application, the glass transition temperature Tg of the arylamine organic compounds is greater than or equal to 100 °C. Further, the glass transition temperature Tg of the arylamine organic compounds is greater than or equal to 120 °C. Further, the glass transition temperature Tg of the arylamine organic compounds is greater than or equal to 140 °C. Further, the glass transition temperature Tg of the arylamine organic compounds is greater than or equal to 160 °C. Further, the glass transition temperature Tg of the arylamine organic compounds is greater than or equal to 180 °C.

[0075] The present invention also relates to a mixture comprising at least one of the above-mentioned organic compounds and at least one organic functional material, and the organic functional material is selected from hole injection materials, hole transport materials, luminescence assisting materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, organic luminescent guest materials, organic host materials, or inorganic quantum dots. For example, various organic functional materials are described in detail in WO2010135519A1, US20090134784A1, and WO2011110277A1. Hereby, the entire contents of these 3 patent documents are incorporated herein by reference. The organic functional materials can be small molecule and polymer materials.

[0076] An object of the present invention is to provide a material solution for vapor deposition type OLEDs.

[0077] In some embodiments of the present application, the molecular weight of the arylamine organic compound may be less than or equal to 1100 g / mol. Further, the molecular weight of the arylamine organic compound may be less than or equal to 1000 g / mol. Further, the molecular weight of the arylamine organic compound may be less than or equal to 950 g / mol. Still further, the molecular weight of the arylamine organic compound may be less than or equal to 900 g / mol. Still further, the molecular weight of the arylamine organic compound may be less than or equal to 800 g / mol.

[0078] Another object of the present invention is to provide a material solution for printed OLEDs.

[0079] In some embodiments of the present application, the molecular weight of the arylamine organic compound of the present invention is greater than or equal to 600 g / mol. Further, the molecular weight of the arylamine organic compound is greater than or equal to 900 g / mol. Further, the molecular weight of the arylamine organic compound is greater than or equal to 1000 g / mol. Still further, the molecular weight of the arylamine organic compound is greater than or equal to 1100 g / mol.

[0080] The present invention also relates to a composition comprising at least one of the organic compounds or mixtures as described, and at least one organic solvent.

[0081] In some embodiments of the present application, the organic solvent may be selected from any one of aromatic or heteroaromatic, esters, aromatic ketones or aromatic ethers, aliphatic ketones or aliphatic ethers, cycloaliphatic or olefinic compounds, or borate or phosphate compounds, or a mixture of two or more solvents. Preferably, the organic solvent is selected from aromatic or heteroaromatic based solvents.

[0082] Examples of aromatic or heteroaromatic solvents suitable for the present invention include, but are not limited to: p-diisopropylbenzene, pentylbenzene, tetralin, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylcumene, 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-methylcumene, 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-furoate, ethyl 2-furoate, etc.

[0083] Examples of aromatic ketone solvents suitable for the present invention include, but are not limited to: 1-tetralone, 2-tetralone, 2-(phenyloxiranyl)tetralone, 6-(methoxy)tetralone, acetophenone, propiophenone, benzophenone, and their derivatives, such as 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylpropiophenone, 3-methylpropiophenone, 2-methylpropiophenone, etc.

[0084] Examples of aromatic ether solvents suitable for the present invention 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 methyl 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.

[0085] Examples of aliphatic ketone- or aliphatic ether-based solvents suitable for the present invention 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-pentyl 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.

[0086] Examples of borate- or phosphate-based solvents suitable for the present invention include, but are not limited to: alkyl octanoates, alkyl sebacates, alkyl stearates, alkyl benzoates, alkyl phenylacetates, alkyl cinnamates, alkyl oxalates, alkyl maleates, alkyl lactones, alkyl oleates, etc. Octyl octanoate, diethyl sebacate, diallyl phthalate, and isononyl isononanoate are particularly preferred.

[0087] In some embodiments of the present application, the composition may comprise at least one organic compound or polymer or mixture as described above, at least one organic solvent, and at least one co-solvent. Examples of the co-solvent include (but are not limited to): methanol, ethanol, 2-methoxyethanol, dichloromethane, chloroform, chlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1,4-dioxane, acetone, methyl ethyl ketone, 1,2-dichloroethane, 3-phenoxytoluene, 1,1,1-trichloroethane, 1,1,2,2-tetrachloroethane, ethyl acetate, butyl acetate, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, tetralin, decalin, indene, and / or mixtures thereof.

[0088] In some embodiments of the present application, solvents particularly suitable for the present invention are solvents having Hansen solubility parameters in the following ranges: δd (dispersion force) in the range of 17.0 - 23.2 MPa1 / 2, especially in the range of 18.5 - 21.0 MPa1 / 2; δp (polar force) in the range of 0.2 - 12.5 MPa1 / 2, especially in the range of 2.0 - 6.0 MPa1 / 2; δh (hydrogen bonding force) in the range of 0.9 - 14.2 MPa1 / 2, especially in the range of 2.0 - 6.0 MPa1 / 2.

[0089] A composition according to the present invention, wherein the organic solvent is selected considering its boiling point parameter. In the present invention, the boiling point of the organic solvent can be greater than or equal to 150 °C. Further, the boiling point of the organic solvent can be greater than or equal to 180 °C. Further, the boiling point of the organic solvent can be greater than or equal to 200 °C. Still further, the boiling point of the organic solvent can be greater than or equal to 250 °C. Still further, the boiling point of the organic solvent can be 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 an inkjet print head. The organic solvent can evaporate from the solvent system to form a thin film containing the organic functional material.

[0090] In some embodiments of the present application, the composition according to the present invention is a solution. In another embodiment, the composition according to the present invention is a suspension.

[0091] The composition in the embodiments of the present invention may include 0.01 to 10 wt% of the organic compound according to the present invention or a mixture thereof. Further, it may include 0.1 to 15 wt% of the organic compound according to the present invention or a mixture thereof. Still further, it may include 0.2 to 5 wt% of the organic compound according to the present invention or a mixture thereof. Still further, it may include 0.25 to 3 wt% of the organic compound according to the present invention or a mixture thereof.

[0092] The present invention also relates to the use of the composition as a coating or printing ink in the preparation of organic electronic devices, and particularly preferably by a preparation method of printing or coating.

[0093] 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, lithographic printing, flexographic printing, rotary printing, spraying, brush coating or pad printing, slot die coating, etc. The preferred ones are gravure printing, nozzle printing and inkjet printing. 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 the related requirements for the relevant solutions, such as solvents and concentrations, viscosities, etc.

[0094] The present invention further relates to the application of the arylamine organic compound, mixture or composition as described above in an organic electronic device. In the embodiments of the present invention, it is preferred to use the organic compound in the hole transport layer of an OLED device.

[0095] The present invention further relates to an organic electronic device comprising two electrodes and one or more organic functional layers disposed between the two electrodes, the organic functional layer comprising the arylamine organic compound, mixture or composition as described above. Further, the organic electronic device comprises a cathode, an anode and one or more organic functional layers between the cathode and the anode.

[0096] The anode may comprise a conductive metal or metal oxide, or a conductive polymer. The anode can easily inject holes into a hole injection layer (HIL) or a hole transport layer (HTL) or a light-emitting layer. In one embodiment, the absolute value of the difference between the work function of the anode and the HOMO level or valence band level of the light-emitting body in the light-emitting layer or the p-type semiconductor material serving as the HIL or 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 can be easily selected and used by those of ordinary skill in the art. 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 application.

[0097] The cathode may comprise a conductive metal or metal oxide. The cathode can easily inject electrons into the EIL or ETL or directly into the light-emitting layer. In one embodiment, the absolute value of the difference between the work function of the cathode and the LUMO level or conduction band level of the light-emitting body in the light-emitting layer or the n-type semiconductor material serving as the electron injection layer (EIL) or electron transport layer (ETL) or hole blocking layer (HBL) is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. In principle, all materials that can be used as the cathode of an OLED can potentially be used as the cathode material of the devices of the present application. Examples of cathode materials include, but are not limited to: Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloy, BaF2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO, etc. The cathode material can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), etc.

[0098] In some embodiments of the present application, for the organic electronic device according to the present invention, with reference to Figure 1, the organic electronic device 100 includes an anode 110 and a cathode 120 stacked in sequence, and one or more organic functional layers 130 disposed between the anode and the cathode. The organic functional layer is selected from one or more layers of an electron injection layer, an electron transport layer, a hole blocking layer, a hole injection layer, a hole transport layer, an electron blocking layer, and a light-emitting layer, and at least includes a light-emitting layer and a hole transport layer. Materials suitable for use in these functional layers will not be described in detail herein.

[0099] In some embodiments of the present application, for the organic electronic device according to the present invention, the light-emitting material in the light-emitting layer is selected from singlet light emitters, triplet light emitters, or TADF materials.

[0100] In some embodiments of the present application, for the organic electronic device according to the present invention, the thickness of the general organic functional layer can be 10 nm to 200 nm. Further, the organic functional layer can be 20 nm to 150 nm. Further, the thickness of the organic functional layer can be 30 nm to 100 nm. Still further, the thickness of the organic functional layer can be 40 nm to 90 nm.

[0101] The organic electronic device can be selected from, but is not limited to, an organic light-emitting diode (Organic Light Emitting Diode, abbreviated as OLED), an organic photovoltaic cell (Organic Photovoltaic Cell, abbreviated as OPV), an organic light-emitting electrochemical cell (Organic Light Emitting Electrochemical Cell, abbreviated as OLEEC), an organic field effect transistor (Organic Field Effect Transistor, abbreviated as OFET), an organic light-emitting field effect transistor (Organic Light Emitting Field Effect Transistor, abbreviated as OLEFET), an organic laser (Organic Laser, abbreviated as OL), an organic spintronic device (Organic Spintronic Device, abbreviated as OSD), an organic sensor (Organic Sensor, abbreviated as OS), and an organic plasmon emitting diode (Organic Plasmon Emitting Diode, abbreviated as OPED), etc. Particularly preferred is an organic electroluminescent device, such as OLED, OLEEC, OLEFET.

[0102] The present invention also relates to the application of the organic electronic device according to the present invention in various electronic devices, including but not limited to: display devices, lighting devices, light sources, sensors, etc.

[0103] The present invention also relates to an electronic device comprising the organic electronic device according to the present invention, including but not limited to: display devices, lighting devices, light sources, sensors, and the like.

[0104] The present invention will be described below in conjunction with preferred embodiments, but the present invention is not limited to the following embodiments. It should be understood that the appended claims define the scope of the present invention. Under the guidance of the inventive concept, those skilled in the art should realize that certain changes made to the embodiments of the present invention will be covered by the spirit and scope of the claims of the present invention.

[0105] The present application will be specifically described below through specific embodiments. The following embodiments are only partial embodiments of the present application and do not limit the present application. The raw materials used in the following embodiments are all commercially available products unless otherwise specified.

[0106] Examples of the synthesis method of the compound according to the present invention are given, but the present invention is not limited to the following embodiments.

[0107] Example 1 Synthesis of Compound C-1

[0108]

[0109] Synthesis of Intermediate 1-3:

[0110] Dissolve Compound 1-1 (10 mmol), Compound 1-2 (20 mmol), Pd(dppf) 3 Cl 2 (0.1 mmol), and potassium acetate (30 mmol) in 1,4-dioxane, and stir at 100 °C for 6 h under a nitrogen atmosphere. After cooling the reaction system to room temperature, use a rotary evaporator to evaporate a part of the solvent, and then extract with dichloromethane and water three times. After liquid separation, the organic phase was evaporated to dryness to obtain a crude product. The crude product was purified by column chromatography to obtain Intermediate 1-3 with a yield of 88.6%. Mass spectrometry m / z [H+] = 254.

[0111] Synthesis of Intermediate 1-5:

[0112] Dissolve Compound 1-3 (10 mmol), Compound 1-4 (10 mmol), Pd(PPh 3 ) 4(0.1 mmol) and potassium carbonate (30 mmol) were dissolved in a mixed solvent of toluene, ethanol, and water, and stirred at 100 °C for 6 h under a nitrogen atmosphere. After the reaction system was cooled to room temperature, a part of the solvent was removed using a rotary evaporator, and then extracted three times with dichloromethane and water. After liquid separation, the organic phase was rotary evaporated to dryness to obtain the crude product. The crude product was purified by column chromatography to obtain intermediate 1-5 with a yield of 85.3%. Mass spectrometry m / z [H+] = 544.

[0113] Synthesis of compound C-1:

[0114] Compound 1-5 (10 mmol), compound 1-6 (10 mmol), Pd 2 (dba) 3 (0.1 mmol), X-Phos (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under a nitrogen atmosphere. After the reaction system was cooled to room temperature, a part of the solvent was removed by rotary evaporation using a rotary evaporator. Then, it was extracted three times with dichloromethane and water. The organic phase was rotary evaporated to dryness to obtain the crude product. The crude product was further purified by column chromatography to obtain compound C-1 with a yield of 87.9%. Mass spectrometry m / z [H + = 615.

[0115] Example 2 Synthesis of compound C-2

[0116]

[0117] Synthesis of compound C-2:

[0118] Compound 1-5 (10 mmol), compound 2-1 (10 mmol), Pd 2 (dba) 3 (0.1 mmol), X-Phos (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under a nitrogen atmosphere. After the reaction system was cooled to room temperature, a part of the solvent was removed using a rotary evaporator, and then extracted three times with dichloromethane and water. After liquid separation, the organic phase was rotary evaporated to dryness to obtain the crude product. The crude product was further purified by column chromatography to obtain compound C-2 with a yield of 87.9%. Mass spectrometry m / z [H + = 691.

[0119] Example 3 Synthesis of compound C-3

[0120]

[0121] Synthesis of compound C-3:

[0122] Compounds 1-5 (10 mmol), compound 3-1 (10 mmol), Pd 2 (dba) 3 (0.1 mmol), X-Phos (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under a nitrogen atmosphere. After the reaction system was cooled to room temperature, a part of the solvent was removed using a rotary evaporator, and then extracted 3 times with dichloromethane and water. After liquid separation, the organic phase was dried by evaporation to obtain a crude product. The crude product was further purified by column chromatography separation to obtain compound C-3 with a yield of 88.8%. Mass spectrometry m / z [H + = 665.

[0123] Example 4 Synthesis of compound C-4

[0124]

[0125] Synthesis of compound C-4:

[0126] Compounds 1-5 (10 mmol), compound 4-1 (10 mmol), Pd 2 (dba) 3 (0.1 mmol), X-Phos (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under a nitrogen atmosphere. After the reaction system was cooled to room temperature, a part of the solvent was removed using a rotary evaporator, and then extracted 3 times with dichloromethane and water. After liquid separation, the organic phase was dried by evaporation to obtain a crude product. The crude product was further purified by column chromatography separation to obtain compound C-4 with a yield of 86.3%. Mass spectrometry m / z [H + = 741.

[0127] Example 5 Synthesis of compound C-5

[0128]

[0129] Synthesis of compound C-5:

[0130] Compounds 1-5 (10 mmol), compound 5-1 (10 mmol), Pd 2 (dba) 3 (0.1 mmol), X-Phos (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under a nitrogen atmosphere. After the reaction system was cooled to room temperature, a part of the solvent was removed using a rotary evaporator, and then extracted 3 times with dichloromethane and water. After liquid separation, the organic phase was dried by evaporation to obtain a crude product. The crude product was further purified by column chromatography separation to obtain compound C-5 with a yield of 87.9%. Mass spectrometry m / z [H+ =767。

[0131] Synthesis of Compound C-6 in Example 6

[0132]

[0133] Synthesis of Compound C-6:

[0134] Dissolve Compound 1-5 (10 mmol), Compound 6-1 (10 mmol), Pd 2 (dba) 3 (0.1 mmol), X-Phos (0.2 mmol) and sodium tert-butoxide (30 mmol) in toluene, stir at 100 °C for 6 h under a nitrogen atmosphere. After cooling the reaction system to room temperature, remove a part of the solvent using a rotary evaporator, and then extract with dichloromethane and water three times. After liquid separation, dry the organic phase by evaporation to obtain the crude product. Further purify the crude product by column chromatography separation method to obtain Compound C-6, and the yield is 86.9%. Mass spectrometry m / z [H + =731。

[0135] Synthesis of Compound C-7 in Example 7

[0136]

[0137] Synthesis of Compound C-7:

[0138] Dissolve Compound 1-5 (10 mmol), Compound 7-1 (10 mmol), Pd 2 (dba) 3 (0.1 mmol), X-Phos (0.2 mmol) and sodium tert-butoxide (30 mmol) in toluene, stir at 100 °C for 6 h under a nitrogen atmosphere. After cooling the reaction system to room temperature, remove a part of the solvent using a rotary evaporator, and then extract with dichloromethane and water three times. After liquid separation, dry the organic phase by evaporation to obtain the crude product. Further purify the crude product by column chromatography separation method to obtain Compound C-7, and the yield is 89.1%. Mass spectrometry m / z [H + =705。

[0139] Synthesis of Compound C-8 in Example 8

[0140]

[0141] Synthesis of Intermediate 8-2:

[0142] Dissolve Compound 1-5 (10 mmol), Compound 8-1 (10 mmol), Pd 2 (dba) 3(0.1 mmol), X-Phos (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under a nitrogen atmosphere. After the reaction system was cooled to room temperature, a part of the solvent was removed using a rotary evaporator, and then extracted three times with dichloromethane and water. After liquid separation, the organic phase was dried by rotation to obtain a crude product. The crude product was further purified by column chromatography to obtain compound 8-2 with a yield of 88.3%. Mass spectrometry m / z [H + = 539.

[0143] Synthesis of compound C-8:

[0144] Compound 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 and stirred at 100 °C for 6 h under a nitrogen atmosphere. After the reaction system was cooled to room temperature, a part of the solvent was removed using a rotary evaporator, and then extracted three times with dichloromethane and water. After liquid separation, the organic phase was dried by rotation to obtain a crude product. The crude product was further purified by column chromatography to obtain compound C-8 with a yield of 86.1%. Mass spectrometry m / z [H + = 721.

[0145] Synthesis of compound C-9 in Example 9

[0146]

[0147] Synthesis of intermediate 9-2:

[0148] Compound 1-5 (10 mmol), compound 9-1 (10 mmol), Pd 2 (dba) 3 (0.1 mmol), X-Phos (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under a nitrogen atmosphere. After the reaction system was cooled to room temperature, a part of the solvent was removed using a rotary evaporator, and then extracted three times with dichloromethane and water. After liquid separation, the organic phase was dried by rotation to obtain a crude product. The crude product was further purified by column chromatography to obtain compound 9-2 with a yield of 83.1%. Mass spectrometry m / z [H + = 615.

[0149] Synthesis of compound C-9:

[0150] Compound 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 and stirred at 100 °C for 6 h under a nitrogen atmosphere. After the reaction system was cooled to room temperature, a part of the solvent was removed using a rotary evaporator, and then extracted 3 times with dichloromethane and water. After liquid separation, the organic phase was dried by rotation to obtain a crude product. The crude product was further purified by column chromatography to obtain compound C-9 with a yield of 86.6%. Mass spectrometry m / z [H + = 807.

[0151] Example 10 Synthesis of Compound C-10

[0152]

[0153] Synthesis of Compound C-10:

[0154] Compound 9-2 (10 mmol), compound 10-1 (10 mmol), Pd(dba) 2 (0.1 mmol), TTBP (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under a nitrogen atmosphere. After the reaction system was cooled to room temperature, a part of the solvent was removed using a rotary evaporator, and then extracted 3 times with dichloromethane and water. After liquid separation, the organic phase was dried by rotation to obtain a crude product. The crude product was further purified by column chromatography to obtain compound C-10 with a yield of 85.5%. Mass spectrometry m / z [H + = 781.

[0155] Example 11 Synthesis of Compound C-11

[0156]

[0157] Synthesis of Compound C-11:

[0158] Compound 9-2 (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 and stirred at 100 °C for 6 h under a nitrogen atmosphere. After the reaction system was cooled to room temperature, a part of the solvent was removed using a rotary evaporator, and then extracted 3 times with dichloromethane and water. After liquid separation, the organic phase was dried by rotation to obtain a crude product. The crude product was further purified by column chromatography to obtain compound C-11 with a yield of 88.6%. Mass spectrometry m / z [H + = 797.

[0159] Example 12 Synthesis of Compound C-12

[0160]

[0161] Synthesis of Compound C-12:

[0162] Dissolve Compound 9-2 (10 mmol), Compound 12-1 (10 mmol), Pd(dba) 2 (0.1 mmol), TTBP (0.2 mmol) and sodium tert-butoxide (30 mmol) in toluene, and stir at 100 °C for 6 h under a nitrogen atmosphere. After cooling the reaction system to room temperature, remove a part of the solvent using a rotary evaporator, and then extract with dichloromethane and water three times. After liquid separation, rotary evaporate the organic phase to obtain the crude product. Further purify the crude product by column chromatography separation method to obtain Compound C-12 with a yield of 89.2%. Mass spectrometry m / z[H + = 741.

[0163] Comparative Example

[0164] This application also provides Comparative Examples 1-3. The organic compounds in Comparative Example 1, Comparative Example 2 and Comparative Example 3 are correspondingly denoted as "Ref-01", "Ref-02" and "Ref-03", and their chemical structural formulas are shown as follows:

[0165]

[0166] Energy Levels of Compounds

[0167] In the examples of this application, the energy levels of organic compounds play a key role. Through theoretical calculations, the highest occupied molecular orbital (HOMO) energy levels and the lowest unoccupied molecular orbital (LUMO) energy levels of the compounds obtained in Examples C-1 to C-12 of the present invention, as well as the comparative compounds "Ref-01", "Ref-02" and "Ref-03", can be obtained. Specifically, the energy levels of organic compound materials can be obtained through quantum calculations, such as using TD-DFT (time-dependent density functional theory) through Gaussian09W (Gaussian Inc.). For the specific simulation method, reference can be made to WO2011141110. In the description of the examples of the present invention, the ground state (S 0 ) configuration is calculated according to the density functional theory (DFT) under the basis set of B3LYP / 6-31G(d) or B3LYP / 6-31G(d,p). The HOMO and LUMO values of the material are calculated according to the optimized S 0 structure using time-dependent density functional theory (TD-DFT) under the basis set of B3LYP / 6-31G(d) or B3LYP / 6-31G(d,p). The HOMO and LUMO energy levels are calculated according to the following calibration formula; S 1 , T 1 and the harmonic factor f(S1 )Use directly.

[0168] HOMO (eV) = ((HOMO(G) × 27.212) - 0.9899) / 1.1206

[0169] LUMO (eV) = ((LUMO(G) × 27.212) - 2.0041) / 1.385

[0170] Where HOMO(G) and LUMO(G) are the direct calculation results of Gaussian 09W, with the unit of Hartree.

[0171] HOMO (eV) and LUMO (eV) are the results after conversion, and the summary is shown in Table 1:

[0172] Table 1

[0173]

[0174]

[0175] It can be seen from the results of Table 1 that the HOMO of the organic compounds provided in Examples C-1 to C-12 of the present invention is at the same level as that of the comparative compounds Ref-01, Ref-02, and Ref-03, and even slightly deeper. They are all suitable for light-emitting auxiliary materials, optimize the hole transport ability, and reduce the energy level barrier between the hole transport layer and the light-emitting layer. Moreover, the E T1 and E S1 energy levels of Examples C-1 to C-12 are slightly higher than those of the comparative compounds Ref-01, Ref-02, and Ref-03, which can more effectively prevent electron backflow and maintain the formation and emission of excitons in the light-emitting layer.

[0176] Preparation and Characterization of OLED Devices

[0177] The following will specifically illustrate the preparation method and process of preparing OLED devices using the compounds of the present application through specific device examples. In the following preparation method of OLED devices, ITO conductive glass is used as the anode substrate, PD is used as the hole injection material, HT is used as the hole transport material, Host is used as the host material of the light-emitting layer, Dopant is used as the doping material of the light-emitting layer, HB is used as the hole blocking material, ET and Liq are used as the electron transport materials, Liq is used as the electron injection material, and Al is used as the cathode material. In addition, the compound C-1 of the foregoing synthesis example is used as the light-emitting auxiliary material to prepare the corresponding OLED devices respectively. Among them, the chemical structural formulas of PD, HT, Host, Dopant, ET, and Liq are as follows:

[0178]

[0179] The preparation process of the OLED device using the above materials will be described in detail below through specific examples. In this example, the structure of the prepared OLED device is as follows: The structure of the OLED device is: ITO / PD:HT(3:97, 10 nm) / HT(130 nm) / Compound C-1 of the present invention(90 nm) / Host:Dopant(3%, 40 nm) / ET:Liq(5:5, 30 nm) / Liq(1 nm) / Al(100 nm). Taking the preparation method of the OLED device using Compound C-1 as a light-emitting auxiliary material as an example, the prepared OLED device is denoted as "OLED-1 device". The preparation method of the OLED-1 device includes the following steps:

[0180] a. Cleaning of the conductive glass substrate: Clean it with chloroform, ketone, and isopropyl alcohol, and then perform ultraviolet ozone plasma treatment;

[0181] b. Preparation of the functional layers: First, transfer the ITO substrate into a vacuum vapor deposition device. Under high vacuum (1×10 -6 mbar), use resistance heating evaporation to deposit the hole injection materials PD and HT on the ITO at a deposition rate of to obtain a hole injection layer with a thickness of 10 nm, and the deposition rate ratio is 3:97. Then, deposit the hole transport material HT on the hole injection layer at a deposition rate of to obtain a hole transport layer with a thickness of 130 nm. Then, deposit Compound C-1 provided in the above example on the hole transport layer at a deposition rate of to obtain a light-emitting auxiliary layer with a thickness of 90 nm. Then, deposit Host and Dopant on the light-emitting auxiliary layer at a deposition rate of with a deposition rate ratio of 97:3 to obtain a light-emitting layer with a thickness of 40 nm. Subsequently, in the vacuum chamber, place the electron transport materials ET and Liq in different evaporation crucibles, and co-deposit ET and Liq at a weight ratio of 5:5 under a high vacuum environment (1×10 -6 mbar) to form an electron transport layer with a thickness of 30 nm on the light-emitting layer. Then, deposit the electron injection material Liq on the electron transport layer at a deposition rate of to obtain an electron injection layer with a thickness of 1 nm. Then, deposit the cathode material Al on the electron injection layer at a deposition rate of to obtain a cathode with a thickness of 100 nm.

[0182] c. Encapsulation: The device is encapsulated with ultraviolet curable resin in a nitrogen glove box to finally obtain the OLED device.

[0183] Referring to the preparation method of the reference device OLED-1, the compounds synthesized in the examples were respectively selected as the light-emitting auxiliary materials for the OLED devices, and the OLED-2 to OLED-12 devices were correspondingly prepared. It can be understood that in the preparation methods of the above OLED-1 to OLED-12 devices, except for the different light-emitting auxiliary materials, other experimental conditions are the same.

[0184] Furthermore, referring to the preparation method of the reference device example, the comparative compounds Ref-01 and Ref-02 were respectively used as the light-emitting auxiliary materials, and the comparative example OLED-Ref-01, OLED-Ref-02 and OLED-Ref-03 devices were correspondingly prepared. Compared with the preparation method of the OLED-1 device, in the preparation methods of the OLED-Ref-01, OLED-Ref-02 and OLED-Ref-03 devices, except for the different light-emitting auxiliary materials, other experimental conditions are the same.

[0185] In this application, the current-voltage (J-V) characteristics of the OLED-1 to OLED-12 and OLED-Ref-01 to OLED-Ref-03 devices were characterized, and important parameters such as luminous efficiency and lifetime were recorded at the same time, as shown in Table 2. Among them, the luminous efficiency is the relative value obtained when the current density is 10 mA cm -2 The lifetime (LT95) is the time when the brightness drops to 95% of the initial brightness @1000 nits under a constant current.

[0186] Table 2

[0187]

[0188]

[0189] As can be seen from Table 2, the organic compounds provided in Examples 1 to 12 of the present invention are used as red light-emitting auxiliary materials, and the luminous efficiency and lifetime of the prepared organic light-emitting devices OLED-1 to OLED-12 are higher than those of the comparative example devices OLED-Ref-01, OLED-Ref-02 and OLED-Ref-03. In the compounds of the present invention, the two fluorene groups are connected by a substituted or unsubstituted phenyl group and the adjustment of the connection position significantly realizes the effective extension of the π-conjugated system and the significant optimization of the molecular packing mode, so that the carrier transport property and device stability are better, and thus higher luminous efficiency and longer device lifetime are achieved.

[0190] Based on the light-emitting auxiliary material of the present invention is significantly better than the light-emitting auxiliary material shown in the comparative example. It can be seen that the luminous efficiency and lifetime of the OLED device prepared by using the organic mixture of the present invention are both significantly improved.

[0191] The technical features of the above-described embodiments can be combined arbitrarily. For the sake of concise description, not all possible combinations of the technical features in the above embodiments are described. However, as long as there is no contradiction in the combination of these technical features, it should be considered as the scope described in this specification.

[0192] The above-described embodiments merely represent several implementation manners of the present invention. The description is relatively specific and detailed, but it should not be construed as a limitation on the scope of the invention patent. It should be noted that for those of ordinary skill in the art, without departing from the concept of the present invention, several modifications and improvements can still be made, and these all belong to the protection scope of the present invention. Therefore, the protection scope of the present invention patent shall be subject to the appended claims.

Claims

1. An aromatic amine organic compound, characterized in that: The aromatic amine organic compound includes a structural formula as shown in formula (1): in, R1 and R2, when they appear each time, are independently selected from one of a hydrogen atom, a deuterium atom, a methyl group, a tert-butyl group, a phenyl group, a diphenyl group, a naphthyl group, a fluorenyl group, a dibenzofuranyl group and a dibenzothienyl group; Ar1 and Ar2 are the same or different from each other and are independently selected from one of the following groups: in, Y is selected from O, S and CR3R4; R3 and R4, when present, are independently selected from an alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aromatic group having 5 to 16 ring atoms; R5-R 16 Each occurrence is independently selected from one of a hydrogen atom, a deuterium atom, a methyl group, a tert-butyl group, a phenyl group, a diphenyl group, a naphthyl group, a fluorenyl group, a dibenzofuranyl group, a dibenzothienyl group and a carbazolyl group; The structure crossed by "—" indicates the connection site is any position on the structure that can form a bond, and "*" indicates the connection site.

2. The aromatic amine organic compound according to claim 1, characterized in that: The general formula (1) is selected from any one of formula (2-1) to formula (2-3):

3. The aromatic amine organic compound according to any one of claims 1 to 2, characterized in that: The organic compound is selected from the following structures:

4. The aromatic amine organic compound according to any one of claims 1 to 3, characterized in that: The glass transition temperature of the aromatic amine organic compound is greater than or equal to 100°C.

5. The aromatic amine organic compound according to claim 1, characterized in that: The molar mass of the aromatic amine organic compound is greater than or equal to 600 g / mol; and / or The molar mass of the aromatic amine organic compound is less than or equal to 1100 g / mol.

6. A mixture, characterized in that It comprises at least one aromatic amine organic compound as described in any one of claims 1 to 5 and at least one organic functional material, wherein the organic functional material is selected from at least one of hole injection materials, hole transport materials, luminescence auxiliary materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, organic luminescent guest materials, and organic host materials.

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

8. An organic electronic device, characterized in that: It comprises a luminescence auxiliary material, wherein the luminescence auxiliary material comprises at least one aromatic amine organic compound as described in any one of claims 1 to 5, or the luminescence auxiliary material comprises the mixture as described in claim 6, or the luminescence auxiliary material is prepared from the composition as described in claim 7.

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