Arylamine organic compound, mixture, organic electronic device and display panel

Abstract

The invention provides an arylamine organic compound, a mixture, an organic electronic device and a display panel, and the structural formula of the arylamine organic compound is as follows: # imgabs0. The arylamine organic compound provided by the invention can effectively influence molecular accumulation and regulate the triplet state energy level and charge transfer capability of a material; when the compound is used as a light-emitting auxiliary material to be applied to organic electronic devices, efficient light-emitting efficiency, longer service life and lower driving voltage can be realized.

Description

Technical Field

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

[0002] Organic electroluminescence (OEL) technology directly converts electrical energy into light energy through the optoelectronic properties of organic materials. An organic light-emitting device based on this technology usually consists of an anode, a cathode, and multiple organic functional layers, including 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. Each layer contains specific organic substances to improve the device performance. When a voltage is applied between the anode and the cathode, the anode injects holes into the light-emitting layer, and the cathode injects electrons into the light-emitting layer. The holes and electrons combine in the light-emitting layer to form excitons, and the excitons release light energy when returning to the ground state, thus achieving light emission. As a representative of OEL technology, the organic light-emitting diode (OLED) exhibits significant advantages in the fields of flat panel display and lighting due to its self-luminescence, high brightness, high efficiency, low voltage, wide viewing angle, and high contrast. For example, in terms of wide viewing angle, fast response, low voltage requirement, and ultra-thin design, it shows the great potential and wide application of OLED technology in the future.

[0003] In terms of improving the light-emitting efficiency and extending the service life of OLED devices, the selection and design of light-emitting auxiliary materials are crucial. A well-designed light-emitting auxiliary material can balance the carrier transport in the OLED device, effectively suppress the reverse migration of electrons, promote the recombination of electrons and holes mainly in the central region of the light-emitting layer, and reduce the non-radiative recombination of excitons, thereby improving the light-emitting efficiency and extending the service life. Therefore, designing more efficient novel light-emitting auxiliary materials to further adjust the balance of hole and electron transport inside the device is the key to improving the device efficiency and life and maintaining a low driving voltage. Summary of the Invention

[0004] Embodiments of this application provide an aromatic amine organic compound, a mixture, an organic electronic device, and a display panel. The aromatic amine organic compound has good performance in transporting and regulating charge balance and can be used as a light-emitting auxiliary material in organic light-emitting devices to improve the light-emitting efficiency of the devices and extend the service life.

[0005] To achieve the above object, according to the first aspect of this application, there is provided an aromatic amine organic compound, and the structural formula of the aromatic amine organic compound is shown as general formula (1):

[0006] [[ID=2,4]]

[0007] Among them, X is selected from an oxygen atom or a sulfur atom;

[0008] R1 is selected from a methyl group, a phenyl group, a biphenyl group or a naphthyl group;

[0009] R2 is selected from a hydrogen atom, a deuterium atom, a halogen group, a cyano group, a straight-chain alkyl group having 1 to 10 carbon atoms, a branched-chain alkyl group having 3 to 10 carbon atoms, a cyclic alkyl group having 3 to 10 carbon atoms, an aromatic group having 5 to 20 ring atoms, or a heteroaromatic group having 5 to 20 ring atoms;

[0010] Ar is selected from a substituted or unsubstituted aromatic group having 5 to 22 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 20 ring atoms;

[0011] “—” indicates that the connection site is at any bond-forming position on the crossed ring structure.

[0012] In some embodiments of the present application, R2 is selected from a hydrogen atom, a deuterium atom, a halogen group, a cyano group or any one of the following groups:

[0013]

[0014] Among them, Y is selected from O, S, CR4R5 or NR6;

[0015] R4, R5, and R6 are each independently selected from a methyl group, a phenyl group, a biphenyl group or a naphthyl group;

[0016] “—” indicates that the connection site is at any bond-forming position on the crossed ring structure;

[0017] “*” indicates the connection site.

[0018] In some embodiments of the present application, Ar is selected from any one of the following groups:

[0019]

[0020] Among them, Z is selected from O, S, CR7R8 or NR9;

[0021] R7, R8, and R9 are each independently selected from a methyl group, a phenyl group, a biphenyl group or a naphthyl group;

[0022] “—” indicates that the connection site is at any bond-forming position on the crossed ring structure;

[0023] “*” indicates the connection site.

[0024] In some embodiments of the present application, the general formula (1) is selected from any one of the general formulas (2-1) to (2-4):

[0025]

[0026] In some embodiments of the present application, the aromatic amine organic compound is selected from at least one of the compounds represented by the following structural formulas:

[0027]

[0028]

[0029]

[0030]

[0031]

[0032]

[0033]

[0034]

[0035]

[0036]

[0037]

[0038]

[0039]

[0040]

[0041]

[0042]

[0043] According to a second aspect of the present application, there is provided a mixture including the aromatic amine organic compound in any of the above embodiments and at least one organic functional material, and the organic functional material is selected from at least one of a hole injection material, a hole transport material, a luminescence assisting 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.

[0044] According to a third aspect of the present application, there is provided an organic electronic device including the aromatic amine organic compound or the mixture in any of the above embodiments.

[0045] In some embodiments of the present application, the organic electronic device includes a first electrode, a second electrode, and an organic functional layer located between the first electrode and the second electrode. The material of the organic functional layer includes the arylamine organic compound, or the material of the organic functional layer includes the mixture.

[0046] In some embodiments of the present application, the organic functional layer includes a light-emitting auxiliary layer and a light-emitting layer arranged in a stacked manner. The material of the light-emitting auxiliary layer includes the arylamine organic compound.

[0047] According to the fourth aspect of the present application, there is provided a display panel including the organic electronic device in any of the above embodiments.

[0048] In the arylamine organic compound, mixture, organic electronic device, and display panel provided by the embodiments of the present application, connecting benzodimethylfluorene and dibenzofuran / dibenzothiophene through an N atom as the core structure of the arylamine organic compound can effectively affect molecular packing and regulate the triplet energy level and charge transport ability of the material. Therefore, the arylamine organic compound of the present application can be used as a light-emitting auxiliary material in organic electronic devices, thereby achieving high luminous efficiency, longer service life, and lower driving voltage.

[0049] Other features and advantages of the present application will be described in detail in the subsequent specific implementation section. BRIEF DESCRIPTION OF THE DRAWINGS

[0050] 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 drawings in the following description are only some embodiments of the present application, and those skilled in the art can obtain other drawings based on these drawings without creative efforts.

[0051] In order to more completely understand the present application and its beneficial effects, the following will be described in conjunction with the drawings, where the same reference numerals represent the same parts in the following description.

[0052] Figure 1 is a schematic structural diagram of an organic electronic device provided by an embodiment of the present application.

[0053] Description of the reference numerals:

[0054] 100, organic light-emitting device; 1, substrate; 11, first electrode; 12, hole injection layer; 13, hole transport layer; 14, light-emitting auxiliary layer; 15, light-emitting layer; 16, electron transport layer; 17, electron injection layer; 18, second electrode. DETAILED DESCRIPTION OF THE EMBODIMENTS

[0055] Next, the technical solutions in the embodiments of the present application will be clearly and completely described in conjunction with the accompanying drawings in the embodiments of the present application.

[0056] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by those of ordinary skill in the art.

[0057] The term "and / or" used herein includes any and all combinations of one or more of the related listed items.

[0058] In the present application, "substituted" means that a hydrogen atom in the substituent is replaced by a substituent.

[0059] In the present application, "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, 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 silyl, C 2-10 alkylamino, C 6-30 arylamino, or a combination of the above groups, etc.

[0060] In the present application, "the number of ring atoms" means the number of atoms among the atoms constituting the ring itself in a structural compound obtained by bonding atoms in a ring (for example, a monocyclic compound, a fused-ring compound, a crosslinked compound, a carbocyclic compound, a heterocyclic compound). When the ring is substituted by a substituent, 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 in a benzene ring is 6, the number of ring atoms in a naphthalene ring is 10, and the number of ring atoms in a thiophenyl group is 5.

[0061] In the present application, "alkyl" may represent a straight-chain, branched-chain and / or cyclic alkyl. The number of carbon atoms in the alkyl may be 1 to 20, and more preferably 1 to 10. Phrases containing this term, for example, "C 1-9"Alkyl" refers to an alkyl group containing 1 to 9 carbon atoms, and each occurrence can independently be a C1 alkyl group, C2 alkyl group, C3 alkyl group, C4 alkyl group, C5 alkyl group, C6 alkyl group, C7 alkyl group, C8 alkyl group or 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.

[0062] "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, or 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, 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), such as acenaphthene, fluorene, or 9,9-diarylfluorene, triarylamine, diaryl ether systems should also be included in the definition of aryl groups.

[0063] As used herein, unless otherwise specified, the term "heteroaromatic group having 5 to 20 ring atoms" refers to a monovalent group including a carbocyclic aromatic system having at least one heteroatom selected from nitrogen atom, oxygen atom, phosphorus atom, sulfur atom or silicon atom as a ring-forming atom and 5 to 20 ring atoms. Non-limiting examples of the heteroaromatic group having 5 to 20 ring atoms may include furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, tetrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl, 1,3,5-triazinyl, benzofuryl, benzisofuryl, benzothienyl, benzisothienyl, indolyl, isoindolyl, indazolyl, benzimidazolyl, benzoxazolyl, benzisoxazolyl, benzothiazolyl, 2,1,3-benzoxadiazole, quinolinyl, isoquinolinyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, benzotriazinyl, benzoxazinyl, purinyl, pteridinyl, indolizinyl, benzothiazinyl, acridinyl, phenazinyl, phenothiazinyl, phenoxazinyl, dibenzofuryl, dibenzothienyl, carbazolyl, naphthofuryl, quinolinyl, isoquinolinyl, indolo[1,2-f]phenanthridinyl, imidazo[2,1-a]isoquinolinyl, imidazo[1,2-a]quinolinyl, benzo[4,5]imidazo[1,2-a]pyridinyl, imidazo[1,2-a]pyridinyl, benzofuro[3,2-c]quinolinyl, naphtho[1,2-b]benzofuryl, naphtho[2,3-b]benzofuryl, etc., and also includes aromatic combined groups with heteroatoms, but is not limited thereto.

[0064] In the present application, "*" connected to a single bond represents a connection or fusion site.

[0065] In the present application, 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;

[0066] In the present application, the single bond to which a substituent is attached 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.

[0067] An embodiment of the present application provides an aromatic amine organic compound, and the structural formula of the aromatic amine organic compound is shown as general formula (1):

[0068]

[0069] Wherein, X is selected from an oxygen atom or a sulfur atom.

[0070] R1 is selected from methyl, phenyl, biphenyl or naphthyl.

[0071] R2 is selected from a hydrogen atom, a deuterium atom, a halogen group, a cyano group, a straight-chain alkyl group having 1 to 10 carbon atoms, a branched-chain alkyl group having 3 to 10 carbon atoms, a cyclic alkyl group having 3 to 10 carbon atoms, an aromatic group having 5 to 20 ring atoms, or a heteroaromatic group having 5 to 20 ring atoms.

[0072] Ar is selected from a substituted or unsubstituted aromatic group having 5 to 22 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 20 ring atoms.

[0073] The heteroatom in the heteroaromatic group mentioned in the embodiments of the present application is selected from any one of a nitrogen atom, an oxygen atom or a sulfur atom.

[0074] "—" indicates that the connection site is at any bond-forming position on the crossed ring structure.

[0075] In the arylamine organic compound provided by the embodiments of the present application, benzodimethylfluorene and dibenzofuran / dibenzothiophene are connected through an N atom as the core structure of the arylamine organic compound, which can effectively affect molecular packing and regulate the triplet energy level and charge transport ability of the material. Therefore, the arylamine organic compound of the present application can be used as a luminescence auxiliary material in organic electronic devices, thereby achieving high luminous efficiency, longer service life and lower driving voltage.

[0076] In some embodiments, R2 is selected from a hydrogen atom, a deuterium atom, a halogen group, a cyano group or any one of the following groups:

[0077]

[0078] Among them, Y is selected from O, S, CR4R5 or NR6.

[0079] R4, R5, and R6 are each independently selected from methyl, phenyl, biphenyl or naphthyl.

[0080] "—" indicates that the connection site is at any bond-forming position on the crossed ring structure.

[0081] "*" indicates the connection site.

[0082] In some embodiments, Ar is selected from any one of the following groups:

[0083]

[0084] Among them: Z is selected from O, S, CR7R8 or NR9.

[0085] R7, R8, and R9 are each independently selected from methyl, phenyl, biphenyl, or naphthyl.

[0086] “—” indicates that the connection site is at any bond-forming position on the crossed ring structure.

[0087] “*” represents the connection site.

[0088] In some embodiments, the general formula (1) is selected from any one of the general formulas (2-1) to (2-4):

[0089]

[0090] Wherein, X is selected from an oxygen atom or a sulfur atom.

[0091] R1 is selected from methyl, phenyl, biphenyl, or naphthyl.

[0092] R2 is selected from a hydrogen atom, a deuterium atom, a halogen group, a cyano group, a straight-chain alkyl group having 1 to 10 carbon atoms, a branched-chain alkyl group having 3 to 10 carbon atoms, a cyclic alkyl group having 3 to 10 carbon atoms, an aromatic group having 5 to 20 ring atoms, or a heteroaromatic group having 5 to 20 ring atoms.

[0093] Ar is selected from a substituted or unsubstituted aromatic group having 5 to 22 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 20 ring atoms.

[0094] In some embodiments, the arylamine organic compound is selected from at least one of the compounds represented by the following structural formulas:

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112] In addition, the hydrogen atoms in the above structure can be further arbitrarily substituted.

[0113] In some embodiments, the arylamine organic compounds of the present application can be used as functional materials in electronic devices, especially in OLED devices. Organic functional materials can be divided into hole injection materials, hole transport materials, light-emitting auxiliary materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, light-emitting guest materials, and host materials. Among them, the host materials can be divided into phosphorescent host materials, fluorescent host materials, and host materials for TADF light-emitting materials. The arylamine organic compounds according to the present application can be any one of them.

[0114] In some embodiments, the arylamine organic compound represented by the above formula (1) provided in the embodiments of the present application can be used as a light-emitting auxiliary material.

[0115] In some embodiments, for the arylamine organic compounds provided according to the present application, their glass transition temperature Tg ≥ 100 °C. In a preferred embodiment, Tg ≥ 120 °C. In a more preferably optional embodiment, Tg ≥ 140 °C. In a more preferred embodiment, Tg ≥ 160 °C. In a most preferably optional embodiment, Tg ≥ 180 °C.

[0116] The embodiments of the present application also provide a mixture, comprising at least one arylamine compound represented by formula (1) and at least one organic functional material. The organic functional material is selected from at least one of hole injection materials, hole transport materials, light-emitting auxiliary materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, organic light-emitting guest materials, organic host materials, and inorganic quantum dots. For example, various organic functional materials are described in detail in patent publication numbers WO2010135519A1, US20090134784A1, and WO2011110277A1. Hereby, the entire contents of these three patent documents are incorporated herein by reference. The organic functional material can be a small molecule and a polymer material.

[0117] The arylamine organic compound provided by the embodiment of the present application can be applied to vapor deposition type OLED devices.

[0118] For example, in some embodiments, the molecular weight of the arylamine organic compound provided by the embodiment of the present application is ≤ 1100 g / mol; in some preferred embodiments, the molecular weight of the arylamine organic compound provided by the embodiment of the present application is ≤ 1000 g / mol; in some more preferred embodiments, the molecular weight of the arylamine organic compound provided by the embodiment of the present application is ≤ 950 g / mol; in some even more preferred embodiments, the molecular weight of the arylamine organic compound provided by the embodiment of the present application is ≤ 900 g / mol; in some most preferred embodiments, the molecular weight of the arylamine organic compound provided by the embodiment of the present application is ≤ 800 g / mol.

[0119] The arylamine organic compound provided by the embodiment of the present application can be applied to printed OLED devices. For example, in some embodiments, the molecular weight of the arylamine organic compound provided by the embodiment of the present application is ≥ 500 g / mol; in some preferred embodiments, the molecular weight of the arylamine organic compound provided by the embodiment of the present application is ≥ 700 g / mol; in some more preferred embodiments, the molecular weight of the arylamine organic compound provided by the embodiment of the present application is ≥ 900 g / mol; in some even more preferred embodiments, the molecular weight of the arylamine organic compound provided by the embodiment of the present application is ≥ 1100 g / mol.

[0120] The embodiment of the present application also provides a composition, comprising at least one arylamine organic compound represented by formula (1) or the above mixture, and at least one organic solvent.

[0121] 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.

[0122] Examples of aromatic or heteroaromatic solvents suitable for this application 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, benzyl butylbenzene, 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.

[0123] Examples of aromatic ketone solvents suitable for this application 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.

[0124] 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.

[0125] Examples of aliphatic ketone or aliphatic ether solvents suitable for this application include, but are not limited to: 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2,5-hexanedione, 2,6,8-trimethyl-4-nonanone, 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.

[0126] Examples of borate or phosphate solvents suitable for this 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.

[0127] In some embodiments, a composition according to this application may comprise at least one of the above-mentioned aromatic amine organic compounds or polymers or mixtures, at least one organic solvent, and 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.

[0128] In some preferred embodiments, solvents particularly suitable for this application are solvents with 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 bond force) in the range of 0.9 - 14.2 MPa1 / 2, especially in the range of 2.0 - 6.0 MPa1 / 2.

[0129] In the composition provided by the embodiments of this application, the boiling point parameter of the organic solvent needs to be considered when selecting it. In this application, the boiling point of the organic solvent ≥ 150 °C; preferably ≥ 180 °C; more preferably ≥ 200 °C; still more preferably ≥ 250 °C; most preferably ≥ 275 °C or ≥ 300 °C. Boiling points within these ranges are beneficial for preventing nozzle clogging of the inkjet print head. The organic solvent can evaporate from the solvent system to form a film containing the organic functional material.

[0130] In some embodiments, the composition provided by the embodiments of the present application is a solution; in other embodiments, the composition provided by the embodiments of the present application is a suspension.

[0131] The composition in the embodiments of the present application may include 0.01 wt% to 10 wt% of the above-mentioned aromatic amine organic compound or the above-mentioned mixture. Preferably, the mass fraction range of the aromatic amine organic compound or the mixture in the composition is 0.1 wt% to 15 wt%, more preferably, the mass fraction range of the aromatic amine organic compound or the mixture in the composition is 0.2 wt% to 5 wt%; even more preferably, the mass fraction range of the aromatic amine organic compound or the mixture in the composition is 0.25 wt% to 3 wt%.

[0132] The embodiments of the present application also provide a use of the above-mentioned composition as a coating or printing ink in the preparation of organic electronic devices. A particularly preferred use is to prepare organic electronic devices as a coating or printing ink by a preparation method of printing or coating.

[0133] Among them, suitable printing or coating techniques include (but are not limited to) inkjet printing, nozzle printing, letterpress printing, screen printing, dip coating, spin coating, blade coating, roller printing, reverse roll printing, lithographic printing, flexographic printing, rotary printing, spraying, brush coating 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 their related requirements for the relevant solutions, such as solvents and concentrations, viscosities, etc.

[0134] The embodiments of the present application further provide an application of the aromatic amine organic compound, the mixture or the composition in an organic electronic device. In the embodiments of the present application, the aromatic amine organic compound or the mixture is preferably used in an OLED device.

[0135] As Figure 1 shown, the embodiments of the present application also provide an organic electronic device 100. The organic electronic device 100 includes the above-mentioned aromatic amine organic compound or the above-mentioned mixture.

[0136] Specifically, the organic electronic device 100 includes a first electrode 11, a second electrode 18, and an organic functional layer located between the first electrode 11 and the second electrode 18.

[0137] In some embodiments, the material of the organic functional layer comprises the above-mentioned arylamine organic compound, or the material of the organic functional layer comprises the above-mentioned mixture, or the material of the organic functional layer is prepared from the above-mentioned arylamine organic compound, the above-mentioned mixture or the above-mentioned composition.

[0138] In a specific embodiment, the first electrode 11 can be an anode, and the second electrode 18 can be a cathode.

[0139] Specifically, the organic functional layer is selected from at least one of a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, a light-emitting auxiliary layer, and an organic light-emitting layer. Preferably, the organic functional layer comprises a light-emitting auxiliary layer and a light-emitting layer stacked on top of each other.

[0140] In a specific embodiment, as Figure 1 shown, the organic electronic device 100 may include a hole injection layer 12, a hole transport layer 13, a light-emitting auxiliary layer 14, a light-emitting layer 15, an electron transport layer 16, and an electron injection layer 17 stacked in sequence on the first electrode 11. Among them, the material of the light-emitting auxiliary layer 14 comprises at least one arylamine organic compound represented by formula (1).

[0141] Specifically, the organic electronic device 100 further includes a substrate 1. The substrate 1 serves as a supporting base, and the first electrode 11 is disposed on the substrate 1.

[0142] In some embodiments, the organic electronic device 100 includes any one of a red organic light-emitting device, a blue organic light-emitting device, and a green organic light-emitting device. That is to say, the arylamine organic compound represented by formula (1) provided in the embodiments of the present application can be used as a red light-emitting auxiliary material, a blue light-emitting auxiliary material, and a green light-emitting auxiliary material.

[0143] In a preferred embodiment, the arylamine organic compound represented by formula (1) is a red light-emitting auxiliary material.

[0144] Specifically, the organic electronic device 100 includes, but is not limited to, 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 plasmonic emission diode (OPED), etc. Particularly preferred is an organic electroluminescent device, such as an OLED, an OLEEC, or an OLEFET.

[0145] The anode may comprise a conductive metal or metal oxide, or a conductive polymer. The anode can easily inject holes into the hole injection layer (HIL), hole transport layer (HTL), or 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 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.

[0146] The cathode may comprise a conductive metal or 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 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.

[0147] In some embodiments, the organic electronic device according to the present application includes one or more organic functional layers selected from one or more of an electron injection layer, electron transport layer, hole blocking layer, hole injection layer, hole transport layer, electron blocking layer, and light-emitting layer, and at least includes a light-emitting layer and a hole transport layer. The materials suitable for these functional layers are as described above and will not be elaborated here.

[0148] In some embodiments, the light-emitting material in the light-emitting layer 15 of the organic electronic device 100 is selected from singlet emitters, triplet emitters, or thermally activated delayed fluorescence (TADF) materials.

[0149] In some embodiments, the thickness of the organic functional layer of the organic electronic device 100 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.

[0150] The organic electronic 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, and the like.

[0151] The embodiments of the present application also provide an electronic device, and the electronic device includes the organic electronic device 100 provided by the embodiments of the present application. The electronic device includes but is not limited to display devices, lighting devices, light sources, sensors, and the like.

[0152] The embodiments of the present application also provide a display panel, and the display panel includes the above-mentioned organic electronic device 100.

[0153] The present application will be described below in conjunction with preferred embodiments, but the present application is not limited to the following embodiments. It should be understood that the appended claims define the scope of the present application. Under the guidance of the concept of the present application, those skilled in the art should realize that certain changes made to the embodiments of the present application will be covered by the spirit and scope of the claims of the present application.

[0155] The organic compounds and their preparation methods of the present application will be further described in detail below in conjunction with specific embodiments. The raw materials used in the following embodiments are all commercially available products unless otherwise specified.

[0156] Example 1

[0157] The synthetic route of compound M1 is as follows:

[0158]

[0159] Synthesis of intermediate 1-3:

[0160] Dissolve compound 1-1 (10 mmol), compound 1-2 (10 mmol), Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) in a mixed solvent of 1,4-dioxane and water, and stir at 100 °C for 8 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, the organic phase was dried by rotary evaporation to obtain a crude product. The crude product was purified by column chromatography to obtain intermediate 1-3, and the yield was 88.7%. Mass spectrometry m / z[H + = 309.

[0161] Synthesis of intermediate 1-5:

[0162] Weigh the intermediate 3 (2.62 g, 10.00 mmol) by measurement, place it in a two-necked flask, cool it in an ice-water bath, add THF, displace nitrogen three times, dropwise add 2 mol / L methylmagnesium bromide reagent (12.5 mL, 25 mmol) with a syringe, then heat it to 50 °C, stir and react for 6 h, cool it to room temperature, add 20 mL of 1 mol / L hydrochloric acid, wash it with water, extract it with dichloromethane, wash it with saturated sodium bicarbonate solution, collect the organic phase, add anhydrous sodium sulfate for drying, spin-dry the solvent to obtain intermediate 1-4. Place intermediate 4 in a two-necked flask, add 5 ml of glacial acetic acid, stir and dissolve it thoroughly, cool it in an ice bath, dropwise add 15 mL of phosphoric acid, react at room temperature for 2 h after 30 min, drop the reaction solution into saturated sodium carbonate solution, extract it with dichloromethane, collect the organic phase, add anhydrous sodium sulfate for drying, spin-dry the solvent, and obtain intermediate 1-5 by column chromatography with a yield of 40.5%. Mass spectrum m / z [H + = 292.

[0163] Synthesis of compound M1:

[0164] Dissolve intermediate 1-5 (10 mmol), compound 1-6 (10 mmol), Pd2(dba)3 (0.1 mmol), X-Phos (0.2 mmol) and sodium tert-butoxide (30 mmol) in xylene, stir at 140 °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. Then, extract it 3 times with dichloromethane and water. Spin-dry the organic phase to obtain the crude product. Further purify the crude product by column chromatography separation method to obtain compound M1 with a yield of 82.1%. Mass spectrum m / z [H + = 591. Elemental analysis structure (molecular formula C 44 H 33 NO): The measured values are C, 89.29; H, 5.60; N, 2.38; O, 2.73.

[0165] Example 2

[0166] The synthesis route of compound M2 is as follows:

[0167]

[0168] The synthesis method of compound M2 is the same as that of compound M1, with a yield of 80.5%. Mass spectrum m / z [H + = 591. Elemental analysis structure (molecular formula C 44 H 33 NO): The measured values are C, 89.34; H, 5.64; N, 2.33; O, 2.69.

[0169] Example 3

[0170] The synthetic route of compound M3 is as follows:

[0171]

[0172] Synthesis of intermediate 3-2:

[0173] Dissolve intermediate 1-5 (10 mmol), compound 3-1 (10 mmol), Pd2(dba)3 (0.1 mmol), X-Phos (0.2 mmol) and sodium tert-butoxide (30 mmol) in toluene, and stir at 120 °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. Then, extract with dichloromethane and water three times. Rotate the organic phase to dryness to obtain the crude product. Further purify the crude product by column chromatography separation method to obtain compound M1, yield: 88.6%. Mass spectrometry m / z [H + =439.

[0174] Synthesis of compound M3:

[0175] Dissolve intermediate 3-2 (10 mmol), compound 3-3 (10 mmol), Pd2(dba)3 (0.1 mmol), X-Phos (0.2 mmol) and sodium tert-butoxide (30 mmol) in xylene, and stir at 140 °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. Then, extract with dichloromethane and water three times. Rotate the organic phase to dryness to obtain the crude product. Further purify the crude product by column chromatography separation method to obtain compound M3, yield: 85.6%. Mass spectrometry m / z [H + =693. Elemental analysis structure (molecular formula C 52 H 39 NO): The measured values are C, 90.03; H, 5.65; N, 2.04; O, 2.29.

[0176] Example 4

[0177] The synthetic route of compound M4 is as follows:

[0178]

[0179] The synthetic method of compound M4 is the same as that of compound M3, yield: 87.8%. Mass spectrometry m / z [H + =693. Elemental analysis structure (molecular formula C 52 H 39 NO): The measured values are C, 89.99; H, 5.65; N, 2.04; O, 2.33.

[0180] Example 5

[0181] The synthetic route of compound M5 is as follows:

[0182]

[0183] The synthetic method of intermediate 5-3 is the same as that of intermediate 1-3, and the yield is 85.1%. Mass spectrum m / z [H + = 371.

[0184] The synthetic method of intermediate 5-5 is the same as that of intermediate 1-5, and the yield is 45.7%. Mass spectrum m / z [H + = 354.

[0185] The synthetic method of compound M5 is the same as that of compound M1, and the yield is 83.2%. Mass spectrum m / z [H + = 653. Elemental analysis structure (molecular formula C 49 H 35 NO): The measured values are C, 90.04; H, 5.38; N, 2.12; O, 2.48.

[0186] Example 6

[0187] The synthetic route of compound M6 is as follows:

[0188]

[0189] The synthetic method of compound M6 is the same as that of compound M1, and the yield is 82.5%. Mass spectrum m / z [H + = 653. Elemental analysis structure (molecular formula C 49 H 35 NO): The measured values are C, 89.98; H, 5.37; N, 2.16; O, 2.48.

[0190] Example 7

[0191] The synthetic route of compound M7 is as follows:

[0192]

[0193] The synthetic method of intermediate 7-2 is the same as that of intermediate 3-2, and the yield is 90.7%. Mass spectrum m / z [H + = 501.

[0194] The synthetic method of compound M7 is the same as that of compound M3, and the yield is 89.5%. Mass spectrum m / z [H + = 755. Elemental analysis structure (molecular formula C 57 H 41NO): The test values are C, 90.58; H, 5.45; N, 1.83; O, 2.14.

[0195] Example 8

[0196] The synthetic route of compound M8 is as follows:

[0197]

[0198] The synthetic method of compound M8 is the same as that of compound M4, yield: 89.5%. Mass spectrum m / z [H + = 755. Elemental analysis results (molecular formula C 57 H 41 NO): The test values are C, 90.56; H, 5.47; N, 1.85; O, 2.12.

[0199] Example 9

[0200] The synthetic route of compound M9 is as follows:

[0201]

[0202] Synthesis of intermediate 9-3:

[0203] Dissolve compound 9-1 (10 mmol), compound 9-2 (10 mmol), Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) in a mixed solvent of 1,4-dioxane and water, and stir at 100 °C for 8 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 a crude product. Purify the crude product by column chromatography to obtain intermediate 9-3, with a yield of 87.5%. Mass spectrum m / z [H + = 347.

[0204] Synthesis of intermediate 9-4:

[0205] Dissolve compound 9-1 (10 mmol), compound 9-2 (10 mmol), Pd2(dba)3 (0.1 mmol), X-Phos (0.2 mmol) and potassium acetate (30 mmol) in 1,4-dioxane solvent, 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, dry the organic phase by evaporation to obtain a crude product. Purify the crude product by column chromatography to obtain intermediate 9-4, with a yield of 92.5%. Mass spectrum m / z [H + = 438.

[0206] The synthesis method of intermediate 9-6 is the same as that of intermediate 1-3, yield: 85.4%. Mass spectrometry m / z [H + = 448.

[0207] The synthesis method of intermediate 9-8 is the same as that of intermediate 1-5, yield: 50.2%. Mass spectrometry m / z [H + = 430.

[0208] The synthesis method of compound M9 is the same as that of compound M1, yield: 86.6%. Mass spectrometry m / z [H + = 729. Elemental analysis structure (molecular formula C 55 H 39 NO): The measured values are C, 90.47; H, 5.42; N, 1.93; O, 2.18.

[0209] Example 10

[0210] The synthesis route of compound M10 is as follows:

[0211]

[0212] The synthesis method of compound M10 is the same as that of compound M1, yield: 84.1%. Mass spectrometry m / z [H + = 729. Elemental analysis structure (molecular formula C 55 H 39 NO): The measured values are C, 90.45; H, 5.42; N, 1.94; O, 2.19.

[0213] Example 11

[0214] The synthesis route of compound M11 is as follows:

[0215]

[0216] The synthesis method of intermediate 11-2 is the same as that of intermediate 3-2, yield: 92.1%. Mass spectrometry m / z [H + = 577.

[0217] The synthesis method of compound M11 is the same as that of compound M3, yield: 84.8%. Mass spectrometry m / z [H + = 832. Elemental analysis structure (molecular formula C 63 H 45 NO): The measured values are C, 90.90; H, 5.47; N, 1.66; O, 1.96.

[0218] Example 12

[0219] The synthetic route of compound M12 is as follows:

[0220]

[0221] The synthetic method of compound M12 is the same as that of compound M4, yield: 87.3%. Mass spectrum m / z [H + = 832. Elemental analysis structure (molecular formula C 63 H 45 NO): The measured values are C, 90.90; H, 5.49; N, 1.66; O, 1.94.

[0222] Example 13

[0223] The synthetic route of compound M13 is as follows:

[0224]

[0225] The synthetic method of intermediate 13-3 is the same as that of intermediate 9-3, yield: 84.5%. Mass spectrum m / z [H + = 320.

[0226] The synthetic method of intermediate 13-4 is the same as that of intermediate 9-4, yield: 87.1%. Mass spectrum m / z [H + = 412.

[0227] The synthetic method of intermediate 13-6 is the same as that of intermediate 1-3, yield: 86.8%. Mass spectrum m / z [H + = 421.

[0228] The synthetic method of intermediate 13-8 is the same as that of intermediate 1-5, yield: 42.5%. Mass spectrum m / z [H + = 404.

[0229] The synthetic method of compound M13 is the same as that of compound M1, yield: 85.2%. Mass spectrum m / z [H + = 703. Elemental analysis structure (molecular formula C 53 H 37 NO): The measured values are C, 90.47; H, 5.33; N, 1.96; O, 2.24.

[0230] Example 14

[0231] The synthetic route of compound M14 is as follows:

[0232]

[0233] The synthesis method of compound M14 is the same as that of compound M1, yield: 80.1%. Mass spectrometry m / z [H + = 703. Elemental analysis results (molecular formula C 53 H 37 NO): measured values are C, 90.40; H, 5.32; N, 1.99; O, 2.29.

[0234] Example 15

[0235] The synthesis route of compound M15 is as follows:

[0236]

[0237] The synthesis method of intermediate 15-2 is the same as that of intermediate 3-2, yield: 86.1%. Mass spectrometry m / z [H + = 551.

[0238] The synthesis method of compound M15 is the same as that of compound M3, yield: 82.9%. Mass spectrometry m / z [H + = 806. Elemental analysis results (molecular formula C 61 H 43 NO): measured values are C, 90.88; H, 5.40; N, 1.70; O, 2.02.

[0239] Example 16

[0240] The synthesis route of compound M16 is as follows:

[0241]

[0242] The synthesis method of compound M16 is the same as that of compound M4, yield: 86.3%. Mass spectrometry m / z [H + = 805. Elemental analysis results (molecular formula C 61 H 43 NO): measured values are C, 90.92; H, 5.36; N, 1.77; O, 1.95.

[0243] Example 17

[0244] The synthesis route of compound M17 is as follows:

[0245]

[0246] The synthesis method of compound M17 is the same as that of compound M1, yield: 82.4%. Mass spectrometry m / z [H + = 669. Elemental analysis results (molecular formula C 49 H 35(NS): The test values are C, 87.83; H, 5.25; N, 2.12; S, 4.81.

[0247] Example 18

[0248] The synthetic route of compound M18 is as follows:

[0249]

[0250] The synthesis method of compound M18 is the same as that of compound M1, yield: 86.1%. Mass spectrum m / z [H + = 669. Elemental analysis structure (molecular formula C 49 H 35 (NS): The test values are C, 87.84; H, 5.25; N, 2.11; S, 4.81.

[0251] Example 19

[0252] The synthetic route of compound M19 is as follows:

[0253]

[0254] The synthesis method of compound M19 is the same as that of compound M1, yield: 83.5%. Mass spectrum m / z [H + = 595. Elemental analysis structure (molecular formula C 43 H 30 (FNO): The test values are C, 86.72; H, 5.06; F, 3.17; N, 2.35; O, 2.71.

[0255] Example 20

[0256] The synthetic route of compound M20 is as follows:

[0257]

[0258] The synthesis method of compound M20 is the same as that of compound M1, yield: 86.4%. Mass spectrum m / z [H + = 591. Elemental analysis structure (molecular formula C 44 H 33 (NO): The test values are C, 89.30; H, 5.63; N, 2.35; O, 2.72.

[0259] Example 21

[0260] The synthetic route of compound M21 is as follows:

[0261]

[0262] The synthesis method of compound M21 is the same as that of compound M1, yield: 81.3%. Mass spectrometry m / z [H + = 578. Elemental analysis structure (molecular formula C 43 H 30 DNO): The measured values are C, 89.23; H, 5.59; N, 2.40; O, 2.77.

[0263] Example 22

[0264] The synthesis route of compound M22 is as follows:

[0265]

[0266] The synthesis method of compound M22 is the same as that of compound M1, yield: 84.2%. Mass spectrometry m / z [H + = 602. Elemental analysis structure (molecular formula C 44 H 30 N2O): The measured values are C, 87.68; H, 5.04; N, 4.65; O, 2.63.

[0267] Example 23 Synthesis of compound M23

[0268]

[0269] The synthesis method of compound M23 is the same as that of compound M1, yield: 83.1%. Mass spectrometry m / z [H + = 653. Elemental analysis structure (molecular formula C 49 H 35 NO): The measured values are C, 90.03; H, 5.42; N, 2.10; O, 2.44.

[0270] Example 24

[0271] The synthesis route of compound M24 is as follows:

[0272]

[0273] The synthesis method of compound M24 is the same as that of compound M1, yield: 86.1%. Mass spectrometry m / z [H + = 743. Elemental analysis structure (molecular formula C 55 H 37 NO2): The measured values are C, 88.80; H, 5.01; N, 1.88; O, 4.30.

[0274] Comparative example

[0275] The present application also provides Comparative Example 1 and Comparative Example 2. The comparative compound of Comparative Example 1 is denoted as "Ref-01", and the comparative compound of Comparative Example 2 is denoted as "Ref-02". Their chemical structural formulas are shown as follows:

[0276]

[0277] Energy levels of the compound

[0278] In the embodiments of the present application, the energy levels of the organic compounds play a crucial role. Through theoretical calculations, the highest occupied molecular orbital (HOMO) energy levels and the lowest unoccupied molecular orbital (LUMO) energy levels of the compounds M1-M24 prepared in Embodiments 1-24 of the present application, as well as the comparative compounds Ref-01 and Ref-02, can be obtained. Specifically, the energy levels of the organic compound materials can be obtained through quantum calculations. For example, using TD-DFT (time-dependent density functional theory) through Gaussian09W (Gaussian Inc.). The specific simulation method can be referred to WO2011141110. In the description of the embodiments of the present application, the ground state (S0) 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 S0 structure using the 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; S1, T1 and the harmonic factor f(S1) are directly used.

[0279] HOMO(eV) = ((HOMO(G) × 27.212) - 0.9899) / 1.1206

[0280] LUMO(eV) = ((LUMO(G) × 27.212) - 2.0041) / 1.385

[0281] Where HOMO(G) and LUMO(G) are the direct calculation results of Gaussian 09W, with the unit of Hartree. HOMO(eV) and LUMO(eV) are the results after conversion. The summary of the energy level test results of the compounds M1-M24 and the comparative compounds Ref-01 and Ref-02 is shown in Table 1:

[0282] Table 1

[0283]

[0284]

[0285] As can be seen from Table 1, the HOMO energy levels of Compounds M1 to M24 in the examples of this application are at the same level as those of Comparative Compounds Ref-01 and Ref-02, or even slightly lower. This indicates that these compounds are all suitable for use as luminescence auxiliary materials, capable of optimizing the hole transport ability and effectively reducing the energy level barrier between the hole transport layer and the luminescence layer. In addition, the triplet energy levels (E T1 ) of Compounds M1 to M24 are slightly higher than the triplet energy levels (E T1 ) of Comparative Compounds Ref-01 and Ref-02. This means that the arylamine organic compounds provided in the examples of this application are more conducive to effectively preventing electron back transfer, ensuring the formation and luminescence of excitons in the luminescence layer, thereby improving the luminescence efficiency and stability of the device. The possible reason is that in the arylamine organic compounds provided in the examples of this application, the ingenious combination of 5-position substituted benzodimethylfluorene and dibenzofuran / dibenzothiophene can enhance the triplet energy level of the compound.

[0286] Preparation and Characterization of OLED Devices

[0287] The following will specifically illustrate the preparation method and process of an OLED device when the arylamine organic compounds provided in the examples of this application are used as luminescence auxiliary materials in the OLED device through specific device examples. In the following preparation method of the OLED device, 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 luminescence layer, Dopant is used as the doping material of the luminescence 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, Compounds M1 to M2 of the above synthesis examples and Comparative Compounds Ref-01 and Ref-02 are used as luminescence auxiliary materials to prepare corresponding OLED devices respectively. Among them, the chemical structural formulas of PD, HT, Host, Dopant, ET, and Liq are shown as follows:

[0288]

[0289] The following will specifically illustrate the preparation process of the OLED device using the above materials through specific examples.

[0290] Device Example 1

[0291] In this embodiment, the structure of the fabricated OLED device is: ITO / PD:HT(3:97, 10 nm) / HT(130 nm) / Compound M1(90 nm) / Host:Dopant(3%, 40 nm) / ET:Liq(5:5, 30 nm) / Liq(1 nm) / Al(100 nm). The OLED device prepared with Compound M1 as the red light emission assisting material is denoted as "OLED-1 device".

[0292] The preparation method of the OLED-1 device includes the following steps:

[0293] a. Cleaning of the conductive glass substrate: Clean it with chloroform, ketone, and isopropyl alcohol, and then perform ultraviolet ozone plasma treatment;

[0294] b. Preparation of 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. Next, deposit the Compound M1 provided in the above embodiment on the hole transport layer at a deposition rate of to obtain a light emission assisting layer with a thickness of 90 nm. Then, deposit Host and Dopant on the light emission assisting 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. Next, 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.

[0295] c. Encapsulation: Encapsulate the device with ultraviolet curable resin in a nitrogen glove box to finally obtain the OLED device.

[0296] Device Examples 2 - 24

[0297] The compound M1 in Device Example 1 was replaced with compounds M2 to M24 respectively, and referring to the preparation method of Device OLED-1, Devices OLED-2 to OLED-24 were correspondingly prepared. Among them, in the preparation methods of the above OLED-1 to OLED-24 devices, except for the different light-emitting auxiliary materials, other experimental conditions were the same.

[0298] Device Comparative Example

[0299] The compound M1 in Device Example 1 was replaced with comparative compounds Ref-01 and Ref-02 respectively, and referring to the preparation method of Device Example 1, Devices OLED-Ref-01 and OLED-Ref-02 were correspondingly prepared. Among them, in the preparation methods of Devices OLED-Ref-01 and OLED-Ref-02, except for the different light-emitting auxiliary materials, other experimental conditions were the same.

[0300] In this application, the current-voltage (J-V) characteristics of Devices OLED-1 to OLED-24, OLED-Ref-01, and OLED-Ref-02 were characterized, and important parameters such as luminous efficiency and lifetime were recorded simultaneously, as shown in Table 2. Among them, the luminous efficiency is the relative value obtained when the current density is 10 mA / cm 2 and the lifetime (LT95) is the time when the brightness drops to 95% of the initial brightness @1000 nits under a constant current.

[0301] Table 2

[0302]

[0303]

[0304] As can be seen from Table 2, when the compounds M1 to M24 provided in Examples 1 to 24 of this application were used as red light-emitting auxiliary materials, the luminous efficiency and lifetime of the prepared Devices OLED-1 to OLED-24 were improved compared with Devices OLED-Ref-01 and OLED-Ref-02, and at the same time, a lower driving voltage could be maintained. It can be seen that the light-emitting auxiliary materials of this application show obvious advantages in performance compared with the light-emitting auxiliary materials in the comparative examples. The possible reason is that in the arylamine organic compounds provided in the examples of this application, the ingenious combination of 5-position-positioned substituted benzo[1,2-b:4,5-b']difluorene and dibenzofuran / dibenzothiophene is more conducive to effectively preventing electron backtransfer, ensuring the formation and luminescence of excitons in the light-emitting layer, thereby improving the luminous efficiency and stability of the device.

[0305] 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, features defined with "first" and "second" may explicitly or implicitly include one or more features. In the description of the present application, "a plurality of" means two or more, unless otherwise specifically defined.

[0306] In the above embodiments, the descriptions of the respective embodiments have their own focuses. For parts not described in detail in a certain embodiment, reference may be made to the relevant descriptions of other embodiments.

[0307] Among the embodiments, implementation manners and related technical features of the present application, they can be combined and replaced with each other without conflict.

[0308] The above are only the preferred embodiments of the present application and do not impose any form of limitation on the present application. However, any simple modifications, equivalent changes and modifications made to the above embodiments based on the technical essence of the present application without departing from the content of the technical solution of the present application still fall within the scope of the technical solution of the present application.

Claims

1. An aromatic amine organic compound, characterized in that, The structural formula of the arylamine organic compound is shown in general formula (1): Wherein, X is selected from an oxygen atom or a sulfur atom; R1 is selected from a methyl group, a phenyl group, a biphenyl group or a naphthyl group; R2 is selected from a hydrogen atom, a deuterium atom, a halogen group, a cyano group, a straight-chain alkyl group having 1 to 10 carbon atoms, a branched-chain alkyl group having 3 to 10 carbon atoms, a cyclic alkyl group having 3 to 10 carbon atoms, an aromatic group having 5 to 20 ring atoms, or a heteroaromatic group having 5 to 20 ring atoms; Ar is selected from a substituted or unsubstituted aromatic group having 5 to 22 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 20 ring atoms; "—" indicates that the connection site is at any bond-forming position on the crossed ring structure.

2. The aromatic amine-based organic compound according to claim 1, wherein R2 is selected from a hydrogen atom, a deuterium atom, a halogen group, a cyano group or any one of the following groups: Wherein, Y is selected from O, S, CR4R5 or NR6; R4, R5, R6 are each independently selected from a methyl group, a phenyl group, a biphenyl group or a naphthyl group; "—" indicates that the connection site is at any bond-forming position on the crossed ring structure; "*" indicates the connection site.

3. The aromatic amine-based organic compound according to claim 1, characterized in that, Ar is selected from any one of the following groups: Wherein, Z is selected from O, S, CR7R8 or NR9; R7, R8, R9 are each independently selected from a methyl group, a phenyl group, a biphenyl group or a naphthyl group; "—" indicates that the connection site is at any bond-forming position on the crossed ring structure; "*" indicates the connection site.

4. The aromatic amine organic compound according to claim 1, wherein General formula (1) is selected from any one of general formulas (2-1) to (2-4):

5. The aromatic amine-based organic compound according to claim 1, characterized in that, The arylamine organic compound is selected from at least one of the compounds shown by the following structural formulas:

6. A mixture, characterized in that, Comprising the arylamine organic compound according to 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, 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, an organic host material and an inorganic quantum dot.

7. An organic electronic device, characterized in that, Comprising the arylamine organic compound according to any one of claims 1 to 5 or the mixture according to claim 6.

8. The organic electronic device according to claim 7, wherein The organic electronic device includes a first electrode, a second electrode and an organic functional layer located between the first electrode and the second electrode, and the material of the organic functional layer includes the arylamine organic compound, or the material of the organic functional layer includes the mixture.

9. The organic electronic device according to claim 8, characterized in that, The organic functional layer includes a light-emitting auxiliary layer and a light-emitting layer arranged in a stacked manner, and the material of the light-emitting auxiliary layer includes the arylamine organic compound.

10. A display panel, characterized in that, Comprising the organic electronic device according to any one of claims 7 to 9.

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