Arylamine organic compound, organic electroluminescent device and display panel

Abstract

The invention provides an arylamine organic compound, an organic electroluminescent device and a display panel. The arylamine organic compound has a structural formula shown in the following general formula # imgabs0 # R, wherein R is selected from a hydrogen atom, a deuterium atom, a halogen group, an alkyl group with 1-12 carbon atoms, an aromatic group with 5-20 ring atoms or a heteroaromatic group with 5-20 ring atoms; l1 and L2 are independently selected from a single bond, a substituted or unsubstituted aromatic group having 5-20 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5-20 ring atoms; ar1 and Ar2 are independently selected from a substituted or unsubstituted aromatic group with 5-25 ring atoms, or a substituted or unsubstituted heteroaromatic group with 5-25 ring atoms. When the arylamine organic compound is applied to the organic electroluminescent device, the driving voltage of the device can be effectively reduced, the luminous efficiency of the device can be greatly improved, and the service life of the device can be greatly prolonged.

Description

Technical Field

[0001] This application relates to the field of organic electroluminescence technology, and in particular, to an aromatic amine organic compound, an organic electroluminescent device, and a display panel. Background Art

[0002] Organic electroluminescence (OEL) technology utilizes the optoelectronic properties of organic materials to directly convert electrical energy into light energy. An organic electroluminescent device based on this technology generally consists of an anode, a cathode, and multiple organic functional layers, which include a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, an electron transport layer, and an electron injection layer, etc. Each layer contains specific organic substances aimed at improving the overall performance of the device. When a voltage is applied between the electrodes, the anode injects holes, and the cathode injects electrons. The two combine to form excitons, and the excitons release light energy during the process of returning to the ground state. As a typical representative of OEL technology, OLED shines in the fields of flat panel display and lighting with its many advantages such as self-luminescence, high brightness, high efficiency, low voltage, wide viewing angle, and high contrast. Its characteristics such as wide viewing angle, fast response, low voltage requirement, and ultra-thin design fully demonstrate the huge potential and broad application prospects of OLED technology in the future.

[0003] In terms of improving the luminous efficiency and extending the service life of OLED devices, the selection and design of light-emitting auxiliary materials play a crucial role. Through careful design, the light-emitting auxiliary materials can effectively balance the carrier transport in OLED devices, strongly suppress the reverse migration of electrons, promote the recombination of electrons and holes mainly in the central region of the light-emitting layer, reduce the non-radiative recombination of excitons, and thus improve the luminous efficiency and extend the service life. Therefore, developing more efficient new light-emitting auxiliary materials to further optimize 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. This difficult problem is an urgent topic for researchers in this field to overcome. Summary of the Invention

[0004] In view of the above deficiencies of the prior art, the purpose of the present invention is to provide an aromatic amine organic compound, an organic electroluminescent 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 electroluminescent devices to improve the luminous efficiency and life of the devices, while maintaining a low driving voltage.

[0005] To achieve the above purpose, according to the first aspect of the present application, there is provided an aromatic amine organic compound, and the aromatic amine organic compound has a structural formula shown in the general formula (1):

[0006]

[0007] Wherein, R is selected from a hydrogen atom, a deuterium atom, a halogen group, an alkyl group having 1 to 12 carbon atoms, an aromatic group having 5 to 20 ring atoms, or a heteroaromatic group having 5 to 20 ring atoms;

[0008] L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted aromatic group having 5 to 20 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 20 ring atoms;

[0009] Ar1 and Ar2 are each independently selected from a substituted or unsubstituted aromatic group having 5 to 25 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 25 ring atoms.

[0010] In some embodiments of the present invention, L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted carbazolylene group, a substituted or unsubstituted dibenzofuranylene group, or a substituted or unsubstituted dibenzothiophenylene group.

[0011] In some embodiments of the present invention, L1 and L2 are each independently selected from a single bond, or a substituted or unsubstituted group V; the unsubstituted group V is selected from the group consisting of the following groups:

[0012]

[0013] In some embodiments of the present invention, L1 and L2 are each independently selected from a single bond, or the group consisting of the following groups:

[0014]

[0015] In some embodiments of the present invention, Ar1 and Ar2 are each independently selected from a substituted or unsubstituted group W, and the unsubstituted group W is selected from the group consisting of the following groups:

[0016]

[0017]

[0018] In some embodiments of the present invention, Ar1 and Ar2 are each independently selected from the group consisting of the following groups:

[0019]

[0020] In some embodiments of the present invention, R is selected from a hydrogen atom, a deuterium atom, a halogen group, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a tert-butyl group, an adamantyl group, a phenyl group, a naphthyl group, a biphenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a fluorenyl group, a spirofluorenyl group, or a carbazolyl group.

[0021] In some embodiments of the present invention, the organic compound is selected from the following structures:

[0022]

[0023]

[0024]

[0025]

[0026]

[0027]

[0028]

[0029]

[0030] According to the second aspect of the present application, there is provided an organic electroluminescent device, including an anode, a cathode, and an organic functional layer located between the anode and the cathode, and the material of the organic functional layer may include the arylamine organic compound described in any of the above embodiments.

[0031] According to the third aspect of the present application, there is further provided a display panel, including the above organic electroluminescent device.

[0032] Advantageous effects:

[0033] Compared with the prior art, the present invention has the following significant advantages: The present invention proposes a phenyl multi-substitution strategy for constructing arylamine compounds containing a positioned carbazole and naphthyl group. This strategy connects the carbazolyl group and the naphthyl group to the 4-position or 2-position of the phenyl group respectively, and fuses with the triarylamine structure to form a unique core structure. The triarylamine structure has excellent hole transport performance. In the compounds of the present invention, the carbazolyl group is connected to the ortho-position of the nitrogen atom of the arylamine, and this unique connection method greatly increases the steric hindrance, thereby significantly enhancing the lifetime of the triplet excitons of the compound molecules. In addition, the stable planar structure of the naphthyl group is externally connected through the 2-position of the phenyl group, enhancing the rigidity of the molecule and endowing the compound with excellent thermal stability. When the compound of the present invention is used in the organic functional layer of an organic electroluminescent device, it can not only effectively reduce the driving voltage of the device, but also greatly improve the luminous efficiency and service life of the device. Description of the drawings

[0034] To more clearly illustrate the technical solutions in the embodiments of the present application, the following briefly introduces the drawings required for describing the embodiments. Obviously, the drawings described below are only some embodiments of the present application. Those skilled in the art can also derive other drawings based on these drawings without inventive effort.

[0035] In order to more completely understand the present application and its beneficial effects, the following description will be given in conjunction with the accompanying drawings, wherein the same drawing numbers represent the same parts in the following description.

[0036] Figure 1 Schematic diagram of the film stacking structure of the organic electroluminescent device provided by an embodiment of the present invention.

[0037] Explanation of reference numerals: 100, organic electroluminescent device; 10, anode; 20, hole functional layer; 30, luminescence auxiliary layer; 40, luminescent layer; 50, electron functional layer; 60, cathode. DETAILED DESCRIPTION

[0038] The technical solutions of the present invention will be further described in detail below with reference to 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 provide a more thorough and comprehensive understanding of the disclosure of the present invention.

[0039] Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art.

[0040] As used herein, the term "and / or" includes any and all combinations of one or more of the associated listed items.

[0041] In the present invention, "substituted" means that a hydrogen atom in a substituted group is replaced by a substituent.

[0042] In the present invention, "substituted or unsubstituted" means that the defined group may be substituted or unsubstituted. When the defined group is substituted, it should be understood that it is optionally substituted by groups acceptable in the art, including but not limited to: deuterium atoms, cyano groups, isocyano groups, nitro groups, halogen atoms, C 1-10 Alkyl, C 1-10 Alkoxy, C 1-10 Alkylthio, C 6-30 Aryl, C 6-30 Aryloxy, C 6-30 Arylthio, C 3-30 Heteroaryl, C 1-30 Silane group, C 2-10 Alkylamino, C6-30 an arylamino group, or a combination of the above groups, etc.

[0043] In the present invention, "the number of ring atoms" refers to the number of atoms among the atoms constituting the ring itself of a structural compound obtained by bonding atoms into 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 with 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 thienyl group is 5.

[0044] In the present invention, when the number of ring atoms mentioned is within a certain range, it means that the number of ring atoms can take any integer value within that range, as well as the interval composed of any two values within that range. For example, "5 to 20 ring atoms" means that the number of ring atoms can be 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20, or the interval range composed of any two of the above values, such as [5, 18], [5, 15], [5, 12], [6 - 14], and so on.

[0045] In the present invention, unless otherwise specified, "alkyl" means a straight-chain, branched-chain, and / or cyclic alkyl. The number of carbon atoms of the alkyl can be 1 to 12, and more preferably 1 to 10. Phrases containing this term, for example, "C 1-9 alkyl" refers to an alkyl containing 1 to 9 carbon atoms, and each occurrence can independently be a C1 alkyl, a C2 alkyl, a C3 alkyl, a C4 alkyl, a C5 alkyl, a C6 alkyl, a C7 alkyl, a C8 alkyl, or a C9 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.

[0046] In the present invention, unless otherwise specified, "aryl or aromatic group" refers to an aromatic hydrocarbon group derived by removing one hydrogen atom from an aromatic ring compound, which may 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 20 carbon atoms" refers to an aryl group containing 5 to 20 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, benzo[a]pyrene, acenaphthene, fluorene, and their derivatives. It can be understood that multiple aryl groups can also be interrupted by short non-aromatic units (e.g., <10% non-H atoms, such as C, N, or O atoms), specifically such as acenaphthene, fluorene, or 9,9-diarylfluorene, triarylamine, diaryl ether systems should also be included in the definition of aryl groups.

[0047] In the present invention, "*" connected to a single bond represents a connection or fusion site.

[0048] 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;

[0049] 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.

[0050] Examples of the present invention provide an aromatic amine organic compound, and the aromatic amine organic compound has a structural formula shown in the general formula (1):

[0051]

[0052] Wherein: R is selected from a hydrogen atom, a deuterium atom, a halogen group, an alkyl group having 1 to 12 carbon atoms, an aromatic group having 5 to 20 ring atoms, or a heteroaromatic group having 5 to 20 ring atoms.

[0053] L1 and L2 may be the same or different and are independently selected from a single bond, a substituted or unsubstituted aromatic group having 5 to 20 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 20 ring atoms.

[0054] Ar1 and Ar2 may be the same or different and are independently selected from a substituted or unsubstituted aromatic group having 5 to 25 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 25 ring atoms.

[0055] When L1, L2, Ar1, and Ar2 are selected from substituted aromatic groups or substituted heteroaromatic groups, the substituents in L1, L2, Ar1, and Ar2 may be the same or different, and each substituent in L1, L2, Ar1, and Ar2 may independently be selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 2 to 12 carbon atoms, an aromatic group having 5 to 20 ring atoms, or a heteroaromatic group having 5 to 20 ring atoms.

[0056] In each of the above-mentioned heteroaromatic groups, the heteroatoms may independently be selected from one or more of a nitrogen atom, an oxygen atom, or a sulfur atom.

[0057] The expression with a "—" drawn across the structure indicates that the bonding site is at any position on the structure capable of forming a bond. Optionally, L1 and L2 are independently selected from a single bond, a substituted or unsubstituted aromatic group or heteroaromatic group having 5 to 20 ring atoms.

[0058] Optionally, the substituents in L1 and L2 are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, and an aryl group having 6 to 12 carbon atoms.

[0059] Optionally, L1 and L2 are independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted carbazolylene group, a substituted or unsubstituted dibenzofuranylene group, or a substituted or unsubstituted dibenzothiophenylene group.

[0060] Optionally, the substituents in L1 and L2 are independently selected from deuterium, fluorine, a cyano group, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a tert-butyl group, a phenyl group, a naphthyl group, a biphenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a fluorenyl group, a spirofluorenyl group, or a carbazolyl group.

[0061] Optionally, L1 and L2 are independently selected from a single bond, a substituted or unsubstituted group V; the unsubstituted group V is selected from the group consisting of the following groups:

[0062]

[0063] Among them, the expression with a "—" drawn across the structure indicates that the bonding site is at any position on the structure capable of forming a bond. "*" represents the bonding site. The substituted group V has one or more substituents, and each substituent is independently selected from: deuterium, fluorine, a cyano group, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a tert-butyl group, an adamantyl group, a phenyl group, a naphthyl group, a biphenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a fluorenyl group, a spirofluorenyl group, or a carbazolyl group; when the number of substituents of group V is greater than 1, the substituents may be the same or different.

[0064] Optionally, L1 and L2 can be independently selected from each other as a single bond, or the group consisting of the following groups:

[0065]

[0066] Optionally, Ar1 and Ar2 are independently selected from each other as a substituted or unsubstituted aromatic group having 6 to 20 ring atoms, or a substituted or unsubstituted heteroaromatic group having 6 to 20 ring atoms.

[0067] Optionally, the substituents in the Ar1 and Ar2 are independently selected from each other as deuterium, a halogen group, a cyano group, an alkyl group having 1 to 12 carbon atoms, and an aromatic group having 6 to 12 ring atoms.

[0068] Optionally, Ar1 and Ar2 are selected from a substituted or unsubstituted group W, and the unsubstituted group W is selected from the group consisting of the following groups:

[0069]

[0070]

[0071] . Among them, the expression of "—" across the structure indicates that the connection site is at any position on the structure that can form a bond. "*" represents the connection site.

[0072] The substituted group V can have one or more substituents, and the substituents are independently selected from each other as deuterium, fluorine, a cyano group, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a tert-butyl group, an adamantyl group, a phenyl group, a naphthyl group, a biphenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a fluorenyl group, a spirofluorenyl group, and a carbazolyl group; when the number of substituents of the group W is greater than 1, the substituents can be the same or different.

[0073] Optionally, Ar1 and Ar2 are independently selected from each other from the group consisting of the following groups:

[0074]

[0075] Among them, the expression of "—" across the structure indicates that the connection site is at any position on the structure that can form a bond. "*" represents the connection site. For example can represent the group consisting of the following groups:

[0076] Optionally, R is selected from a hydrogen atom, a deuterium atom, a halogen group, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a tert-butyl group, an adamantyl group, a phenyl group, a naphthyl group, a biphenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a fluorenyl group, a spirofluorenyl group, and a carbazolyl group, but is not limited to the above structures.

[0077] Optionally, the organic compound is selected from the following structures, but is not limited to the following structures:

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086] Among them, the hydrogen atoms in the above structures can be further arbitrarily substituted.

[0087] Compared with the prior art, the present invention has the following remarkable advantages: The present invention proposes a phenyl multi-substitution strategy for constructing an arylamine compound containing a positioned carbazole and naphthyl group. This strategy connects the carbazole group and the naphthyl group to the 4th or 2nd site of the phenyl group respectively and fuses with the triarylamine structure to form a unique core structure. The triarylamine structure has excellent hole transport performance. In the compounds of the present invention, the carbazole group is connected to the ortho position of the nitrogen atom of the arylamine. This unique connection method greatly increases the steric hindrance, thereby significantly enhancing the lifetime of the triplet excitons of the compound molecules. In addition, the stable planar structure of the naphthyl group is externally connected through the 2nd site of the phenyl group, enhancing the molecular rigidity and endowing the compound with excellent thermal stability. When the compounds of the present invention are applied to the organic functional layer of an organic electroluminescent device, it can not only effectively reduce the driving voltage of the device, but also greatly improve the luminous efficiency and service life of the device. Especially when used as a red light emission auxiliary material, it can greatly improve the luminous efficiency and service life of the device.

[0088] For the arylamine organic compound according to the present invention, its glass transition temperature Tg ≥ 100 °C. In a preferred optional embodiment, Tg ≥ 120 °C. In a more preferred optional embodiment, Tg ≥ 140 °C. In a more preferred optional embodiment, Tg ≥ 160 °C. In a most preferred optional embodiment, Tg ≥ 180 °C.

[0089] The present invention also relates to a mixture comprising at least one of the above-mentioned aromatic amine organic compounds and at least one organic functional material, which is selected from 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 or an inorganic quantum dot. For example, various organic functional materials are described in detail in WO2010135519A1, US20090134784A1 and WO2011110277A1. Hereby, the entire content of these 3 patent documents is incorporated herein by reference. The organic functional material can be a small molecule or a polymer material.

[0090] One object of the present invention is to provide a material solution for vapor deposition type OLEDs.

[0091] In certain embodiments, the organic compound according to the present invention has a molecular weight ≤ 1100 g / mol, preferably ≤ 1000 g / mol, very preferably ≤ 950 g / mol, more preferably ≤ 900 g / mol, and most preferably ≤ 800 g / mol.

[0092] Another object of the present invention is to provide a material solution for printed OLEDs.

[0093] In certain embodiments, the organic compound according to the present invention has a molecular weight ≥ 700 g / mol, preferably ≥ 900 g / mol, preferably ≥ 1000 g / mol, and most preferably ≥ 1100 g / mol.

[0094] The present invention also relates to a composition comprising at least one of the above-mentioned organic compounds or the mixture as described above and at least one organic solvent.

[0095] The organic solvent can 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. Optionally, the organic solvent is selected from aromatic or heteroaromatic-based solvents.

[0096] 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 - furan - carboxylate, ethyl 2 - furan - carboxylate, etc.

[0097] 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.

[0098] 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 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.

[0099] 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.

[0100] 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, alkanolactones, alkyl oleates, etc. Octyl octanoate, diethyl sebacate, diallyl phthalate, and isononyl isononanoate are particularly preferred.

[0101] In certain preferred embodiments, a composition according to the present invention may comprise at least one of the aromatic amine-based organic compounds or polymers or mixtures 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.

[0102] In some preferred embodiments, 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 MPa 1 / 2 and particularly in the range of 18.5 - 21.0 MPa 1 / 2 ; δp (polar force) in the range of 0.2 - 12.5 MPa 1 / 2 and particularly in the range of 2.0 - 6.0 MPa 1 / 2 ; δh (hydrogen bonding force) in the range of 0.9 - 14.2 MPa 1 / 2 and particularly in the range of 2.0 - 6.0 MPa 1 / 2 and particularly in the range of 2.0 - 6.0 MPa.

[0103] 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 is greater than or equal to 150 °C; preferably greater than or equal to 180 °C; more preferably greater than or equal to 200 °C; still more preferably greater than or equal to 250 °C; most preferably greater than or equal to 275 °C or greater than or equal to 300 °C. 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.

[0104] In one embodiment, the composition according to the present invention is a solution. In another embodiment, the composition according to the present invention is a suspension.

[0105] The composition in the examples of the present invention may include 0.01 wt% to 10 wt% of the organic compound according to the present invention or a mixture thereof, preferably 0.1 wt% to 15 wt%, more preferably 0.2 wt% to 5 wt%, and most preferably 0.25 wt% to 3 wt%.

[0106] The present invention also relates to the use of the composition as a coating or printing ink in the preparation of an organic electroluminescent device, and particularly preferably by a preparation method of printing or coating.

[0107] 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, 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 relevant solutions, such as solvents and concentrations, viscosities, etc.

[0108] The present invention further relates to the application of the above-mentioned arylamine organic compound, mixture or composition in an organic electroluminescent device.

[0109] The arylamine organic compound according to the present invention can be used as an organic functional material in an electroluminescent device. As Figure 1 shown, the examples of the present invention also provide an electroluminescent device 100, and the electroluminescent device 100 can be an OLED device.

[0110] The electroluminescent device 100 may include an anode 10, a cathode 60, and an organic functional layer located between the anode 10 and the cathode 60. The organic functional layer may include an organic functional material, and the organic functional material may include the arylamine organic compound in any of the above embodiments.

[0111] Optionally, the electroluminescent device 100 may include a light-emitting layer 40 located between the anode 10 and the cathode, a hole functional layer 20 located between the anode 10 and the light-emitting layer 40, a light-emission assisting layer 30 located between the light-emitting layer 40 and the hole functional layer 20, and an electron functional layer 50 located between the light-emitting layer 40 and the cathode 60.

[0112] The light-emitting layer 40 includes a light-emitting guest material and a host material. Among them, the host material can be divided into a phosphorescent host material, a fluorescent host material, and a host material of a TADF light-emitting material. The light-emission assisting layer 30 includes a light-emission assisting material.

[0113] Optionally, in some embodiments, the hole functional layer 20 may include a hole injection layer and a hole transport layer stacked in sequence in a direction away from the anode 10, and the light-emission assisting layer 30 is located between the light-emitting layer 40 and the hole transport layer. The hole injection layer may include a hole injection material. The hole transport layer may include a hole transport material.

[0114] Optionally, in some embodiments, the electron functional layer 50 may include an electron functional layer and an electron injection layer stacked in sequence in a direction away from the light-emitting layer 40. The electron injection layer includes an electron injection material. The electron functional layer includes an electron transport material.

[0115] Optionally, in some embodiments, the electroluminescent device may further include a hole blocking layer disposed between the electron transport layer and the light-emitting layer 40, an electron blocking layer located between the hole transport layer and the light-emitting layer 40, and the light-emission assisting layer 30 is located between the electron blocking layer and the light-emitting layer 40. The hole blocking layer includes a hole blocking material, and the electron blocking layer includes an electron blocking material.

[0116] The organic functional layer may contain the arylamine organic compound, mixture, or be prepared from the above composition as described above. The organic functional layer includes at least one of a hole injection layer, a hole transport layer, an electron blocking layer, a light-emission assisting layer 30, a light-emitting layer 40, a hole blocking layer, an electron transport layer, and an electron injection layer.

[0117] The organic functional materials can be classified 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), and luminescent guest materials (Guest Emitter). The arylamine organic compound provided by the embodiment of the present invention can be any one of them.

[0118] In some embodiments, the arylamine organic compound provided by the embodiment of the present invention can be applied to the luminescence assisting material, and the luminescence assisting material includes the arylamine organic compound provided by the embodiment of the present invention. Further, the arylamine organic compound provided by the embodiment of the present invention can be used as a red light luminescence assisting material.

[0119] Optionally, the anode can include a conductive metal or metal oxide, or a conductive polymer. The anode can easily inject holes into the hole injection layer (HIL) or hole transport layer (HTL) or 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 luminescent 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 application of the present invention.

[0120] Optionally, 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 lumophore 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 device of the present invention application. Examples of cathode materials include, but are not limited to: Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloy, BaF2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO, etc. The cathode material can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), etc.

[0121] In some embodiments, for the organic electroluminescent device according to the present invention, the light-emitting material in the light-emitting layer is selected from singlet emitters, triplet emitters, or TADF materials.

[0122] In some more optional embodiments, for the organic electroluminescent device according to the present invention, the thickness of the general organic functional layer is 10 nm to 200 nm, preferably 20 nm to 150 nm, more preferably 30 nm to 100 nm, and most preferably 40 nm to 90 nm.

[0123] The organic electroluminescent device can be selected from, but is not limited to, organic light-emitting diodes (OLEDs), organic photovoltaic cells (OPVs), organic light-emitting electrochemical cells (OLEECs), organic field-effect transistors (OFETs), organic light-emitting field-effect transistors, organic lasers, organic spintronic devices, organic sensors, and organic plasmon emitting diodes, etc. Particularly preferred are organic electroluminescent devices, such as OLEDs, OLEECs, and organic light-emitting field-effect transistors.

[0124] The present invention also relates to a display panel, which includes the above-mentioned organic electroluminescent device and an array substrate. The array substrate may include a pixel driving circuit, and the organic electroluminescent device is electrically connected to the pixel driving circuit on the array substrate, and this pixel driving circuit is used to drive the organic electroluminescent device to emit light.

[0125] The present invention also relates to the application of the electroluminescent device and the display panel according to the present invention in various electronic devices, including but not limited to: display devices, lighting devices, light sources, sensors, etc.

[0126] The present invention also relates to an electronic device comprising the organic electroluminescent device according to the present invention, including but not limited to: display devices, lighting devices, light sources, sensors, and the like.

[0127] 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. Specific embodiments

[0129] 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.

[0130] Example 1 Synthesis of Compound M1

[0131]

[0132] Synthesis of Intermediate 1-3:

[0133] Dissolve Compound 1-1 (10 mmol), Compound 1-2 (10 mmol) and Cs2CO3 (0.4 mmol) in DMF, 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. Spin-dry the organic phase to obtain a crude product. Further purify the crude product by column chromatography separation method to obtain Intermediate 1-3, yield: 90.1%. Mass spectrometry m / z [H + = 356.

[0134] Synthesis of Intermediate 1-5:

[0135] Dissolve Compound 1-3 (10 mmol), Compound 1-4 (10 mmol), Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) in a mixed solvent of toluene, ethanol and water, and stir at 100 °C for 8 h under a nitrogen atmosphere. After cooling the reaction system to room temperature, use a rotary evaporator to remove a part of the solvent, and then extract with dichloromethane and water three times. After liquid separation, spin-dry the organic phase to obtain a crude product. Purify the crude product by column chromatography separation method to obtain Intermediate 1-5, and the yield is 88.3%. Mass spectrometry m / z [H + = 403.

[0136] Synthesis of Compound M1:

[0137] 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) 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 portion of the solvent was removed by rotary evaporation using a rotary evaporator. Then, the mixture was extracted three times with dichloromethane and water. The organic phase was dried to obtain a crude product. The crude product was further purified by column chromatography to obtain compound M1 with a yield of 82.8%. Mass spectrum m / z [H + ]=536.

[0138] Example 2 Synthesis of Compound M2

[0139]

[0140] The synthesis method of compound M2 refers to the synthesis steps of compound M1 above, with a yield of 84.3%. Mass spectrum m / z [H + ]=688.

[0141] Example 3 Synthesis of Compound M3

[0142]

[0143] The synthesis method of compound M3 refers to the synthesis steps of compound M1 above, with a yield of 86.1%. Mass spectrum m / z [H + ]=728.

[0144] Example 4 Synthesis of Compound M4

[0145]

[0146] The synthesis method of compound M4 refers to the synthesis steps of compound M1 above, with a yield of 84.3%. Mass spectrum m / z [H + ]=702.

[0147] Example 5 Synthesis of Compound M5

[0148]

[0149] The synthesis method of compound M5 refers to the synthesis steps of compound M1 above, with a yield of 82.9%. Mass spectrum m / z [H + ]=719.

[0150] Example 6 Synthesis of Compound M6

[0151]

[0152] The synthesis method of compound M6 refers to the synthesis operation steps of the above-mentioned compound M1, yield: 82.9%. Mass spectrometry m / z[H + = 779.

[0153] Example 7 Synthesis of compound M7

[0154]

[0155] The synthesis method of compound M7 refers to the synthesis operation steps of the above-mentioned compound M1, yield: 81.8%. Mass spectrometry m / z[H + = 702.

[0156] Example 8 Synthesis of compound M8 [[ID=I8]]

[0157]

[0158] Synthesis of intermediate 8-2:

[0159] [[ID=Z5]]Dissolve compound 1-3 (10 mmol), compound 8-1 (10 mmol), Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) in a mixed solvent of toluene, ethanol 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 3 times. After liquid separation, the organic phase was rotary evaporated to obtain a crude product. The crude product was purified by column chromatography to obtain intermediate 1-5 with a yield of 88.3%. Mass spectrometry m / z[H + = 403.

[0160] Synthesis of compound M8:

[0161] Dissolve intermediate 8-2 (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 toluene, 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 rotary evaporate and remove a part of the solvent. Then, extract with dichloromethane and water 3 times. The organic phase was rotary evaporated to obtain a crude product. The crude product was further purified by column chromatography to obtain compound M8 with a yield: 86.1%. Mass spectrometry m / z[H + = 536.

[0162] Example 9 Synthesis of compound M9

[0163]

[0164] The synthesis method of compound M9 refers to the synthesis operation steps of the above-mentioned compound M8, yield: 85.1%. Mass spectrometry m / z[H + = 688.

[0165] Example 10 Synthesis of compound M10

[0166]

[0167] The synthesis method of compound M10 refers to the synthesis operation steps of the above-mentioned compound M8, yield: 86.7%. Mass spectrometry m / z[H + = 728.

[0168] Example 11 Synthesis of compound M11

[0169]

[0170] The synthesis method of compound M11 refers to the synthesis operation steps of the above-mentioned compound M8, yield: 82.9%. Mass spectrometry m / z[H + = 702.

[0171] Example 12 Synthesis of compound M12

[0172]

[0173] The synthesis method of compound M12 refers to the synthesis operation steps of the above-mentioned compound M8, yield: 83.1%. Mass spectrometry m / z[H + = 719.

[0174] Example 13 Synthesis of compound M13

[0175]

[0176] The synthesis method of compound M13 refers to the synthesis operation steps of the above-mentioned compound M8, yield: 88.2%. Mass spectrometry m / z[H + = 779.

[0177] Example 14 Synthesis of compound M14

[0178]

[0179] The synthesis method of compound M14 refers to the synthesis operation steps of the above-mentioned compound M8, yield: 82.6%. Mass spectrometry m / z[H + = 702.

[0180] Example 15 Synthesis of compound M15

[0181]

[0182] The synthesis method of compound M15 refers to the synthesis operation steps of the above-mentioned compound M8, yield: 84.2%. Mass spectrometry m / z[H + = 851.

[0183] Example 16 Synthesis of compound M16

[0184]

[0185] The synthesis method of compound M16 refers to the synthesis operation steps of the above-mentioned compound M8, yield: 85.8%. Mass spectrometry m / z[H + = 852.

[0186] Example 17 Synthesis of compound M17

[0187]

[0188] The synthesis method of compound M17 refers to the synthesis operation steps of the above-mentioned compound M8, yield: 87.1%. Mass spectrometry m / z[H + = 852.

[0189] Example 18 Synthesis of compound M18

[0190]

[0191] The synthesis method of compound M18 refers to the synthesis operation steps of the above-mentioned compound M8, yield: 84.2%. Mass spectrometry m / z[H + = 778.

[0192] Example 19 Synthesis of compound M19

[0193]

[0194] The synthesis method of compound M19 refers to the synthesis operation steps of the above-mentioned compound M8, yield: 82.1%. Mass spectrometry m / z[H + = 778.

[0195] Example 20 Synthesis of compound M20

[0196]

[0197] The synthesis method of intermediate 20-3 refers to the synthesis operation steps of the above-mentioned compound M1, yield: 85.7%. Mass spectrometry m / z[H + = 460.

[0198] The synthesis method of compound M20 refers to the synthesis operation steps of the above-mentioned compound M8, yield: 84.2%. Mass spectrometry m / z[H +=828。

[0199] Synthesis of Compound M21 in Example 21

[0200]

[0201] The synthesis method of Compound M21 refers to the above-mentioned synthesis operation steps of Compound M8, yield: 85.2%. Mass spectrometry m / z[H + =805。

[0202] Comparative Example

[0203] This application also provides Comparative Example 1, denoted as "Ref-01", and its chemical structural formula is shown as follows:

[0204]

[0205] Energy Level of the Compound

[0206] In the examples of this application, the energy level of the organic compound plays a key role. Through theoretical calculation, the highest occupied molecular orbital (HOMO) energy level and the lowest unoccupied molecular orbital (LUMO) energy level of the compounds obtained in Examples M1 to M21 of the present invention and the comparative compound Ref-01 can be obtained. Specifically, the energy level of the organic compound material can be obtained through quantum calculation, 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 (S0) configuration is calculated according to the density functional theory (DFT) under the B3LYP / 6-31G(d) or B3LYP / 6-31G(d,p) basis set. The HOMO and LUMO values of the material are calculated according to the optimized S0 structure using the time-dependent density functional theory (TD-DFT) under the B3LYP / 6-31G(d) or B3LYP / 6-31G(d,p) basis set. 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.

[0207] HOMO(eV) = ((HOMO(G) × 27.212) - 0.9899) / 1.1206;

[0208] LUMO(eV) = ((LUMO(G) × 27.212) - 2.0041) / 1.385.

[0209] 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, and the summary is shown in Table 1:

[0210] Table 1

[0211]

[0212] As can be seen from the data in Table 1 above, the HOMO energy levels of the organic compounds involved in the compounds M1 to M21 of the present invention are at the same level as that of the comparative compound Ref-01, indicating that they are all suitable for use as luminescence auxiliary materials. These compounds can optimize the hole transport ability and effectively reduce the energy level barrier between the hole transport layer and the light-emitting layer, thereby improving the device performance. In addition, the E T1 energy levels of the compounds M1 to M21 of the examples are higher than those of the comparative compound Ref-01. This characteristic enables them to more effectively prevent the back transfer of electrons, ensuring the smooth formation and emission of excitons in the light-emitting layer, and further improving the luminescence efficiency and the stability of the device.

[0213] Glass transition temperature test

[0214] Samples of the compounds M1 to M11 of the present application were tested using a differential scanning calorimeter DSC (TA Instruments Co., Ltd., USA, model DSC25) to determine their glass transition temperature (Tg). The test results are shown in Table 2.

[0215] Table 2

[0216] Material Tg (°C) Material Tg (°C) M1 119 M12 129 M2 128 M13 137 M3 126 M14 112 M4 129 M15 127 M5 131 M16 123 M6 125 M17 125 M7 128 M18 122 M8 122 M19 127 M9 132 M20 130 M10 131 M21 117 M11 135 Ref-01 84

[0217] As can be seen from the data in Table 2 above, compared with the compound Ref-01, the compounds M1 to M21 in the present invention application have higher glass transition temperatures (Tg). When these compounds M1 to M21 are applied to the preparation of organic light-emitting devices, due to their higher Tg values, it helps to enhance the stability and durability of the devices during use and will significantly improve the service life of the devices.

[0218] Preparation and characterization of OLED devices

[0219] The preparation method and process of preparing an OLED device using the compound of the present application will be described in detail below through specific device embodiments. 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 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 M1 of the foregoing synthesis example is used as the light-emitting auxiliary material to prepare the corresponding OLED devices. Among them, the chemical structural formulas of PD, HT, Host, Dopant, ET, and Liq are as follows:

[0220]

[0221] 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: The structure of the OLED device is: ITO / PD:HT(3:97, 10 nm) / HT(130 nm) / Compound M1 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 the compound M1 as the 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:

[0222] a. Cleaning of the conductive glass substrate: Clean it with chloroform, ketone, and isopropyl alcohol, and then perform ultraviolet ozone plasma treatment;

[0223] 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 with a deposition rate ratio of 3:97 to obtain a hole injection layer with a thickness of 10 nm. 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 the compound M1 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, at a deposition rate of The evaporation rate is used to deposit Host and Dopant on the light-emitting auxiliary layer, and the evaporation rate ratio is 97:3, resulting in a light-emitting layer with a thickness of 40 nm. Subsequently, in a vacuum chamber, the electron transport material ET and Liq are placed in different evaporation crucibles, and ET and Liq are co-deposited at a weight ratio of 5:5 in 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, the electron injection material Liq is deposited on the electron transport layer at an evaporation rate of to obtain an electron injection layer with a thickness of 1 nm. Next, the cathode material Al is deposited on the electron injection layer at an evaporation rate of to obtain a cathode with a thickness of 100 nm.

[0224] c. Encapsulation: The device is encapsulated with an ultraviolet-curing resin in a nitrogen glove box, and finally an OLED device is obtained.

[0225] Referring to the preparation method of the reference device OLED-1, the compounds synthesized in the examples are respectively selected as the light-emitting auxiliary materials of the OLED device, and the OLED-2 to OLED-21 devices are correspondingly prepared. It can be understood that in the preparation methods of the above OLED-1 to OLED-21 devices, except for the different light-emitting auxiliary materials, other experimental conditions are the same.

[0226] Furthermore, referring to the preparation method of the reference device example, the comparative compound Ref-01 is respectively used as the light-emitting auxiliary material, and the comparative device OLED-Ref-01 is correspondingly prepared. Compared with the preparation method of the OLED-1 device, in the preparation method of the OLED-Ref-01 device, except for the different light-emitting auxiliary materials, other experimental conditions are the same.

[0227] In this application, the current-voltage (J-V) characteristics of the OLED-No. 1 to OLED-No. 21 and OLED-Ref-01 devices are characterized, and important parameters such as luminous efficiency and lifetime are recorded at the same time, as shown in Table 3. 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.

[0228] Table 3

[0229]

[0230]

[0231] As can be seen from the data in Table 3 above, when the organic compounds provided in Examples 1 to 21 of the present invention are used as red light-emitting auxiliary materials, the prepared organic light-emitting devices OLED-1 to OLED-21 are superior to the control device OLED-Ref-01 in terms of luminous efficiency and lifespan, and also perform excellently in maintaining a low driving voltage.

[0232] Thus, it can be seen that the red light-emitting auxiliary material of the present invention is significantly superior to the similar materials in the comparative examples in terms of performance. This fully demonstrates that the OLED devices prepared using the organic compounds of the present invention not only have a greatly improved luminous efficiency, but also have a significantly extended service life, and at the same time can maintain a low driving voltage, showing excellent comprehensive performance.

[0233] The technical features of the above-described embodiments can be combined arbitrarily. For the sake of brevity of description, not all possible combinations of the technical features in the above-described embodiments are described. However, as long as there is no contradiction in the combination of these technical features, it should be considered to be within the scope described in this specification.

[0234] The above-described embodiments only 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 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 arylamine organic compound has a structural formula shown in general formula (1): Wherein, R is selected from a hydrogen atom, a deuterium atom, a halogen group, an alkyl group having 1 to 12 carbon atoms, an aromatic group having 5 to 20 ring atoms, or a heteroaromatic group having 5 to 20 ring atoms; L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted aromatic group having 5 to 20 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 20 ring atoms; Ar1 and Ar2 are each independently selected from a substituted or unsubstituted aromatic group having 5 to 25 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 25 ring atoms.

2. The aromatic amine organic compound according to claim 1, characterized in that, L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted carbazolylene group, a substituted or unsubstituted dibenzofuranylene group, or a substituted or unsubstituted dibenzothiophenylene group.

3. The aromatic amine organic compound according to claim 1, characterized in that, L1 and L2 are each independently selected from a single bond, or a substituted or unsubstituted group V; the unsubstituted group V is selected from the group consisting of the following groups:

4. The aromatic amine-based organic compound according to claim 3, wherein L1 and L2 are each independently selected from a single bond, or the following group consisting of:

5. The arylamine organic compound according to claim 1, wherein Ar1 and Ar2 are each independently selected from a substituted or unsubstituted group W, and the unsubstituted group W is selected from the group consisting of the following groups:

6. The aromatic amine-based organic compound according to claim 5, wherein, Ar1 and Ar2 are each independently selected from the following group consisting of:

7. The aromatic amine organic compound according to claim 1, characterized in that, R is selected from a hydrogen atom, a deuterium atom, a halogen group, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a tert-butyl group, an adamantyl group, a phenyl group, a naphthyl group, a biphenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a fluorenyl group, a spirofluorenyl group, or a carbazolyl group.

8. The aromatic amine-based organic compound according to claim 1, wherein The organic compound is selected from the following structures:

9. An organic electroluminescent device, characterized in that, Comprising an anode, a cathode, and an organic functional layer located between the anode and the cathode, and the material of the organic functional layer comprises the arylamine organic compound according to any one of claims 1 to 8.

10. A display panel, characterized in that, Comprising the organic electroluminescent device according to claim 9.

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