Arylamine organic compound, mixture, composition and organic electronic device

Abstract

The invention discloses an arylamine organic compound, a mixture, a composition and an organic electronic device, the structure of the arylamine organic compound is represented by a general formula (1), and the arylamine organic compound can be used as a light-emitting auxiliary material for preparation of the organic electronic device. The compound can significantly improve the luminous efficiency and the service life of a device, and can maintain a low driving voltage in the use process. General formula (1).

Description

TECHNICAL FIELD

[0001] The present application relates to the technical field of organic electroluminescence, and in particular to an arylamine organic compound, mixture, composition and organic electronic device. BACKGROUND

[0002] Organic light-emitting (OEL) technology is a technology that converts electrical energy directly into light energy by using organic materials. An organic light-emitting device based on this technology is generally composed of an anode, a cathode and multiple organic functional layers, which include a hole injection layer, a transport layer, a light-emitting auxiliary layer, a light-emitting layer, an electron transport layer and an injection layer, etc. Each layer contains specific organic substances to improve the overall performance of the device. When a voltage is applied between the electrodes, the anode injects holes and the cathode injects electrons, which combine to form excitons. The excitons release light energy in the process of returning to the ground state. As a typical representative of OEL technology, OLED has many advantages such as self-emission, high brightness, high efficiency, low voltage, wide viewing angle and high contrast, etc. It has shown great potential and broad application prospects in the future due to its wide viewing angle, fast response, low voltage requirement and ultra-thin design.

[0003] The selection and design of light-emitting auxiliary materials play a crucial role in improving the light-emitting efficiency and extending the service life of OLED devices. A carefully designed light-emitting auxiliary material can effectively balance the carrier transport in OLED devices, effectively 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 light-emitting 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 device efficiency and service life and maintaining a low driving voltage. SUMMARY

[0004] In view of the above, the present application provides an arylamine organic compound, mixture, composition and organic electronic device, aiming to improve the balance of hole and electron transport inside the device to improve the efficiency and service life of the device, and maintain a low driving voltage.

[0005] The present application is implemented as follows: an arylamine organic compound, the chemical formula of the arylamine organic compound is shown in general formula (1): General formula (1); wherein, L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted C 6-30 an aromatic group, a substituted or unsubstituted C5-30 At least one of the heteroaromatic groups; Ar1 and Ar2 are each independently selected from hydrogen atoms, substituted or unsubstituted C atoms. 6-30 Aromatic groups or substituted or unsubstituted C 5-30 At least one of the heteroaromatic groups; The substituents L1, L2, Ar1, and Ar2, whether substituted or unsubstituted, are selected from tritium atoms, C atoms, and other substituents. 1-15 alkyl, C 6-30 aromatic groups or C 5-30 heteroaromatic groups; In L1, L2, Ar1, and Ar2, the heteroatom in the heteroaromatic group is independently selected from at least one of nitrogen, oxygen, or sulfur atoms; The way a loop structure is represented by a dash "—" indicates that the connection point is located at any position on the loop structure where bonding can occur.

[0006] Optionally, in some embodiments of this application, L1 and L2 are each independently selected from at least one of the following groups: single bond, substituted or unsubstituted: .

[0007] Optionally, in some embodiments of this application, Ar1 and Ar2 are each independently selected from at least one of the following groups: hydrogen atoms, substituted or unsubstituted groups: ; “ "" indicates a connection point.

[0008] Optionally, in some embodiments of this application, the substituted or unsubstituted substituents in L1, L2, Ar1, and Ar2 are independently selected from deuterium, methyl, tert-butyl, adamantyl, phenyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothiophene, fluorenyl, or carbazoyl.

[0009] Optionally, in some embodiments of this application, the chemical formula of the aromatic amine organic compound is selected from general formula (2-1) or general formula (2-2): General formula (2-1); General formula (2-2).

[0010] Optionally, in some embodiments of the present application, the chemical formula of the arylamine organic compound is selected from the following structures: Formula (3-1); Formula (3-2).

[0011] Optionally, in some embodiments of the present application, the chemical formula of the arylamine organic compound is selected from at least one of the following structures: .

[0012] Secondly, embodiments of this application provide a mixture comprising at least one aromatic amine organic compound as described above, and at least one organic functional material, wherein the organic functional material includes hole injection material, hole transport material, light-emitting auxiliary material, electron transport material, electron injection material, electron blocking material, hole blocking material, organic light-emitting guest material, or organic host material.

[0013] Thirdly, embodiments of this application provide a composition comprising at least one aromatic amine organic compound as described above, or a mixture as described above, and at least one organic solvent.

[0014] Fourthly, embodiments of this application provide an organic electronic device, including a first electrode, a second electrode, and a functional layer located between the first electrode and the second electrode, wherein the functional layer comprises at least one aromatic amine organic compound as described above, or a mixture as described above, or a composition as described above.

[0015] The aromatic amine organic compounds in this application are compounds constructed with oxyphenanthrene and naphthalene as the core components. The oxyphenanthrene and naphthalene structures possess well-planar fused-ring structures, which help reduce the risk of thermal decomposition of the material, thereby improving the stability and lifespan of the device. Simultaneously, the well-planar structure promotes carrier injection and transport, thereby improving the luminous efficiency of the device. Therefore, applying the compounds of this invention as red-light-emitting auxiliary materials in organic light-emitting elements achieves improved luminous efficiency and lifespan while maintaining a low driving voltage, demonstrating significant advantages. Attached Figure Description

[0016] To more clearly illustrate the technical solutions in the embodiments of the present invention, the accompanying drawings used in the description of the embodiments will be briefly introduced below. Obviously, the accompanying drawings described below are only some embodiments of the present invention. For those skilled in the art, other drawings can be obtained based on these drawings without creative effort.

[0017] Figure 1 This is a schematic cross-sectional view of an organic electronic device provided in an embodiment of this application; In the figure, 10 is the substrate; 20 is the anode; 30 is the hole injection layer; 40 is the hole transport layer; 50 is the light-emitting auxiliary layer; 60 is the light-emitting layer; 70 is the electron transport layer; 80 is the electron injection layer; and 90 is the cathode. Detailed Implementation

[0018] The technical solutions of the embodiments of this application will be clearly and completely described below with reference to the accompanying drawings. Obviously, the described embodiments are only some embodiments of this application, and not all embodiments. Based on the embodiments of this application, all other embodiments obtained by those skilled in the art without creative effort are within the scope of protection of this application. Furthermore, it should be understood that the specific embodiments described herein are only for illustration and explanation of this application and are not intended to limit this application.

[0019] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention pertains.

[0020] As used herein, the term "and / or" includes any and all combinations of one or more of the related listed items.

[0021] In this invention, hydrogen atoms include isotopes with different numbers of neutrons, namely protium, deuterium, and tritium.

[0022] In this invention, "substitution" means that the hydrogen atom in the substituent is replaced by the substituent.

[0023] In this invention, "substituted or unsubstituted" means that the defined group may or may not be substituted. When the defined group is substituted, it should be understood that it may be substituted by a group acceptable in the art, including but not limited to: deuterium atom, cyano, isocyano, nitro, halogen atom, C 1-10 alkyl, C 1-10 alkoxy, C 1-10 alkylthio group, C 6-30 aryl, C 6-30 aryloxy group, C 6-30 aryl thiols, C 3-30 heteroaryl, C 1-30 silane, C 2-10 alkylamine group, C 6-30 Aromatic amino groups, or combinations thereof, etc.

[0024] In this invention, "alkyl" can refer to straight-chain, branched, and / or cyclic alkyl groups. The number of carbon atoms in an alkyl group can be 1 to 15. Phrases containing this term, such as "C 1-9"Alkyl" refers to an alkyl group containing 1 to 9 carbon atoms, and each time it appears, it can independently be C1 alkyl, C2 alkyl, C3 alkyl, C4 alkyl, C5 alkyl, C6 alkyl, C7 alkyl, C8 alkyl, or C9 alkyl. Non-limiting examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, adamantane, etc.

[0025] "Aryl or aromatic group" refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removing one hydrogen atom. It can be a monocyclic aryl, a fused-ring aryl, or a polycyclic aryl. For polycyclic compounds, at least one must be an aromatic ring system. For example, "substituted or unsubstituted C..." 6-30 "Aryl group" refers to an aryl group containing 6 to 30 carbon atoms, with optional further substitutions; suitable examples include, but are not limited to: benzene, biphenyl, terphenyl, naphthalene, anthracene, fluoranthene, phenanthrene, benzo[a]phenanthrene, dinaphthalene-based phenylene, tetraphenyl, pyrene, benzo[a]pyrene, acenaphthene, fluorene, and their derivatives. Understandably, multiple aryl groups may also be interrupted by short non-aromatic units (e.g., <10% non-H atoms, such as C, N, or O atoms), specifically acenaphthene, fluorene, or 9,9-diarylfluorene, triarylamines, and diaryl ether systems should also be included in the definition of aryl.

[0026] In this article, "substituted or unsubstituted C" is used. 5-30 "Heteroaromatic group" refers to a monovalent group comprising a carbocyclic heteroaromatic system having at least one heteroatom selected from nitrogen, oxygen, phosphorus, sulfur, or silicon as a cyclic atom and 5 to 30 carbon atoms. Non-limiting examples of heteroaromatic groups containing 5 to 30 carbon atoms may include furanyl, thiopheneyl, pyrroleyl, pyrazolyl, imidazoleyl, 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, 1,2,3 Triazinyl, 1,2,4 Triazine, 1,3,5 Triazinyl, benzofuranyl, benzoisofuranyl, benzothiophenyl, benzoisothiophenyl, indoleyl, isoindoleyl, indazoleyl, benzimidazolyl, benzoxazolyl, benzoisoxazolyl, benzothiazolyl, 2,1,3 Benzoxadiazole, quinolinyl, isoquinolinyl, terolinyl, phthalazinyl, quinazolinyl, quinolinyl, naphridinyl, benzotriazinyl, benzooxazinyl, purine, pteridinyl, indazinyl, benzothiazinyl, acridineyl, benzazinyl, benzthiazinyl, benzoxazinyl, dibenzofuranyl, dibenzothiophenyl, carbazoleyl, naphridinyl, quinolinyl, isoquinolinyl, indole [1,2] f]Phenyridyl, imidazo[2,1] a]Isoquinolinyl, imidazo[1,2] a] Quinolinyl, benzo[4,5]imidazo[1,2] a]pyridyl, imidazo[1,2] a]pyridyl, benzofuran [3,2] c] Quinolinyl, naphtho[1,2] b] Benzofuranyl, naphtho[2,3] b] Benzofuranyl and other aromatic composite groups with heteroatoms, but not limited thereto.

[0027] In this invention, the "*" connected to a single bond indicates a connection or fusion site.

[0028] In this invention, when no linking site is specified in the group, it means that any linkable site in the group is selected as the linking site.

[0029] In this invention, the single bond connecting the substituents extends through the corresponding ring, indicating that the substituent can be connected to any position on the ring, for example... R is attached to any substituted site on the benzene ring.

[0030] According to a first aspect of this application, an aromatic amine organic compound is provided, the chemical formula of which is shown in general formula (1): General formula (1); in, L1 and L2 are each independently selected from single-bonded, substituted, or unsubstituted C bonds. 6-30 Aromatic groups, substituted or unsubstituted C 5-30 At least one of the heteroaromatic groups; Ar1 and Ar2 are each independently selected from hydrogen atoms, substituted or unsubstituted C atoms. 6-30 Aromatic groups or substituted or unsubstituted C 5-30 At least one of the heteroaromatic groups; The substituents L1, L2, Ar1, and Ar2, whether substituted or unsubstituted, are selected from tritium atoms, C atoms, and other substituents.1-15 alkyl, C 6-30 aromatic groups or C 5-30 heteroaromatic groups; In L1, L2, Ar1, and Ar2, the heteroatom in the heteroaromatic group is independently selected from at least one of nitrogen, oxygen, or sulfur atoms; The way a loop structure is represented by a dash "—" indicates that the connection point is located at any position on the loop structure where bonding can occur.

[0031] In some embodiments of this application, L1 and L2 are each independently selected from at least one of the following groups: single bond, substituted or unsubstituted: .

[0032] In some embodiments of this application, Ar1 and Ar2 are each independently selected from at least one of the following groups: hydrogen atom, substituted or unsubstituted: ; “ "" indicates a connection point.

[0033] In some embodiments of this application, the substituted or unsubstituted substituents in L1, L2, Ar1, and Ar2 are independently selected from deuterium, methyl, tert-butyl, adamantyl, phenyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothiophene, fluorenyl, or carbazoyl.

[0034] In some embodiments of this application, the chemical formula of the aromatic amine organic compound is selected from general formula (2-1) or general formula (2-2): General formula (2-1); General formula (2-2).

[0035] In some embodiments of this application, the chemical formula of the aromatic amine organic compound is selected from general formula (3-1) or general formula (3-2): General formula (3-1); General formula (3-2).

[0036] In some embodiments of this application, the chemical formula of the aromatic amine organic compound is selected from at least one of the following structures: 。

[0037] In some embodiments of this application, the aromatic amine organic compound can be used as an organic functional material in electronic devices, particularly OLED devices. Organic functional materials can be categorized as hole injection materials (HIM), hole transport materials (HTM), luminescence assist materials (Prime), electron transport materials (ETM), electron injection materials (EIM), electron blocking materials (EBM), hole blocking materials (HBM), guest luminescent materials, and host materials. Among these, host materials can be further categorized as phosphorescent host materials, fluorescent host materials, and host materials for TADF luminescent materials.

[0038] In one example of this application, aromatic amine organic compounds can be used as luminescent auxiliary materials.

[0039] In one example of this application, the glass transition temperature (Tg) of the aromatic amine organic compound is greater than or equal to 100°C. o C.

[0040] In one example of this application, the glass transition temperature (Tg) of the aromatic amine organic compound is greater than or equal to 120°C. o C.

[0041] In one example of this application, the glass transition temperature (Tg) of the aromatic amine organic compound is greater than or equal to 140°C. o C.

[0042] In another example of this application, the glass transition temperature (Tg) of the aromatic amine organic compound is greater than or equal to 160°C. o C.

[0043] In another example of this application, the glass transition temperature (Tg) of the aromatic amine organic compound is greater than or equal to 180°C. o C.

[0044] According to a second aspect of the embodiments of this application, a mixture is provided, comprising at least one aromatic amine organic compound as described above, and at least one organic functional material.

[0045] In some embodiments of this application, the organic functional material may be selected from 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, or inorganic quantum dots.

[0046] Another objective of this application is to provide material solutions for printed OLEDs.

[0047] In one example of this application, the molecular weight of the aromatic amine organic compound is greater than or equal to 500 g / mol, preferably greater than or equal to 700 g / mol, more preferably greater than or equal to 900 g / mol, and most preferably greater than or equal to 1000 g / mol.

[0048] According to a third aspect of the embodiments of this application, a composition is provided comprising at least one aromatic amine organic compound as described above, or a mixture as described above, and at least one organic solvent.

[0049] In some embodiments of this application, the organic solvent may be selected from any one of aromatic or heteroaromatic compounds, esters, aromatic ketones or aromatic ethers, aliphatic ketones or aliphatic ethers, alicyclic or olefinic compounds, or borate esters or phosphate esters, or a mixture of two or more solvents. In a preferred example of this application, the organic solvent is selected from aromatic or heteroaromatic solvents.

[0050] Examples of aromatic or heteroaromatic solvents suitable for this application include, but are not limited to: p-diisopropylbenzene, pentaphenyl, tetrahydronaphthalene, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, dipentylbenzene, tripentylbenzene, pentylene, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, 1,2,3,4-tetramethylbenzene, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, butylbenzene, dodecylbenzene, dihexylbenzene, dibutylbenzene, p-diisopropylbenzene, cyclohexylbenzene, benzylbutylbenzene, dimethylnaphthalene, 3-Isopropylbiphenyl, p-methylisopropylbenzene, 1-methylnaphthalene, 1,2,4-trichlorobenzene, 4,4-difluorodiphenylmethane, 1,2-dimethoxy-4-(1-propenyl)benzene, diphenylmethane, 2-phenylpyridine, 3-phenylpyridine, N-methyldiphenylamine, 4-isopropylbiphenyl, α,α-dichlorodiphenylmethane, 4-(3-phenylpropyl)pyridine, benzyl benzoate, 1,1-bis(3,4-dimethylphenyl)ethane, 2-isopropylnaphthalene, quinoline, isoquinoline, methyl 2-furanoate, ethyl 2-furanoate, etc.

[0051] Examples of aromatic ketone-based solvents suitable for this application include, but are not limited to: 1-tetrahydronaphthone, 2-tetrahydronaphthone, 2-(phenylepoxy)tetrahydronaphthone, 6-(methoxy)tetrahydronaphthone, acetophenone, phenylacetone, benzophenone, and their derivatives, such as 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylphenylacetone, 3-methylphenylacetone, 2-methylphenylacetone, etc.

[0052] Examples of aromatic ether-based solvents suitable for this application include, but are not limited to: 3-phenoxytoluene, butoxybenzene, p-anisaldehyde dimethyl acetal, tetrahydro-2-phenoxy-2H-pyran, 1,2-dimethoxy-4-(1-propenyl)benzene, 1,4-benzodioxane, 1,3-dipropylbenzene, 2,5-dimethoxytoluene, 4-ethylbenzene, 1,3-dipropoxybenzene, 1,2,4-trimethoxybenzene, 4-(1-propenyl)-1,2-dimethoxybenzene, 1,3-dimethoxybenzene, glycidylphenyl ether, dibenzyl ether, 4-tert-butylanisole, trans-p-propenylanisole, 1,2-dimethoxybenzene, 1-methoxynaphthalene, diphenyl ether, 2-phenoxymethyl ether, 2-phenoxytetrahydrofuran, ethyl-2-naphthyl ether, etc.

[0053] 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, frankinc, 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.

[0054] Examples of suitable boronic acid ester or phosphate ester-based solvents for this application include, but are not limited to: alkyl octanoate, alkyl sebacate, alkyl stearate, alkyl benzoate, alkyl phenylacetate, alkyl cinnamate, alkyl oxalate, alkyl maleate, alkyl lactone, alkyl oleate, etc. Octyl octanoate, diethyl sebacate, diallyl phthalate, and isononyl isononanoate are particularly preferred.

[0055] In one example of this application, a composition according to this application may contain at least one organic compound or mixture as described above, at least one organic solvent, and at least one co-solvent.

[0056] In some embodiments of this application, examples of cosolvents include, but are not limited to: methanol, ethanol, 2-methoxyethanol, dichloromethane, trichloromethane, chlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1,4-dioxane, acetone, methyl ethyl ketone, 1,2-dichloroethane, 3-phenoxytoluene, 1,1,1-trichloroethane, 1,1,2,2-tetrachloroethane, ethyl acetate, butyl acetate, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, tetrahydronaphthalene, naphthane, indene, and / or mixtures thereof.

[0057] In one example of this application, a suitable solvent for the present invention is a Hansen solvent with solubility parameters in the following ranges: δd (dispersion force) in the range of 17.0 to 23.2 MPa¹ / ², particularly in the range of 18.5 to 21.0 MPa¹ / ²; δp (polar force) in the range of 0.2 to 12.5 MPa¹ / ², particularly in the range of 2.0 to 6.0 MPa¹ / ²; and δh (hydrogen bonding force) in the range of 0.9 to 14.2 MPa¹ / ², particularly in the range of 2.0 to 6.0 MPa¹ / ².

[0058] According to the compositions of this application, the boiling point of the organic solvent must be considered when selecting it. In this application, the boiling point of the organic solvent is greater than or equal to 150 °C, preferably greater than or equal to 180 °C, more preferably greater than or equal to 200 °C, more preferably greater than or equal to 250 °C, and 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 the inkjet printhead. The organic solvent can evaporate from the solvent system to form a thin film containing organic functional materials.

[0059] In one example of this application, the composition according to this application is a solution. In another example, the composition according to this application is a suspension.

[0060] The compositions in the embodiments of this application may include 0.01 to 10 wt% of an aromatic amine organic compound or a mixture thereof according to this application, preferably 0.1 to 15 wt%, more preferably 0.2 to 5 wt%, and most preferably 0.25 to 3 wt%.

[0061] The present invention also relates to the use of the composition as a coating or printing ink in the preparation of organic electronic devices, particularly preferably by a preparation method of printing or coating.

[0062] Suitable printing or coating technologies include, but are not limited to, inkjet printing, nozzle printing, letterpress printing, screen printing, dip coating, spin coating, doctor blade coating, roller printing, torsional roller printing, offset printing, flexographic printing, rotary printing, spraying, brushing or pad printing, and slot-fitting coating. Gravure printing, inkjet printing, and gravure printing are preferred. The solution or suspension may additionally include one or more components such as surfactants, lubricants, wetting agents, dispersants, hydrophobic agents, and binders to adjust viscosity, film-forming properties, and improve adhesion. The printing technology and its related requirements for the solution, such as solvent and concentration, viscosity, etc., are also important considerations.

[0063] According to a fourth aspect of the present application, an organic electronic device is provided, including a first electrode, a second electrode, and a functional layer located between the first electrode and the second electrode, wherein the functional layer comprises at least one aromatic amine organic compound as described above, or a mixture as described above, or a composition as described above.

[0064] In some embodiments of this application, an organic electronic device includes a cathode, an anode, and one or more organic functional layers located at the cathode and anode.

[0065] The anode may comprise a conductive metal or metal oxide, or a conductive polymer. Holes can be readily injected 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 light emitter 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 readily selected by those skilled 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 one example of this application, the anode is patterned. Patterned ITO conductive substrates are commercially available and can be used to fabricate devices according to this application.

[0066] The cathode may comprise a conductive metal or metal oxide. Electrons can be readily injected 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 luminescent material 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 suitable for use as cathodes in OLEDs may be used as cathode materials for the devices of this invention. 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.

[0067] In some embodiments, the organic electroluminescent device according to the present invention includes one or more functional layers selected from one or more layers of an electron injection layer, an electron transport layer, a hole blocking layer, a hole injection layer, a hole transport layer, an electron blocking layer, and an emissive layer, wherein at least one emissive layer and one hole transport layer are included. Materials suitable for use in these functional layers are as described above and will not be repeated here.

[0068] For example, refer to Figure 1 The organic electronic device includes a substrate 10 and an anode 20, a hole injection layer 30, a hole transport layer 40, a light-emitting auxiliary layer 50, a light-emitting layer 60, an electron transport layer 70, an electron injection layer 80, and a cathode 90, which are sequentially stacked on the substrate 10.

[0069] In some embodiments, in the organic electroluminescent device according to the present invention, the luminescent material in the luminescent layer is selected from singlet luminescent material, triplet luminescent material, or TADF material.

[0070] In some more alternative embodiments, the organic electroluminescent device according to the invention generally has an organic functional layer thickness of 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.

[0071] The organic electronic device may be selected from, but is not limited to, organic light-emitting diodes (OLEDs), organic photovoltaic cells (OPVs), organic light-emitting 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, with organic electroluminescent devices such as OLEDs, OLEECs, or organic light-emitting field-effect transistors being particularly preferred.

[0072] The present invention also relates to the application of the electroluminescent device according to the present invention in various electronic devices, including but not limited to: display devices, lighting devices, light sources, sensors, etc.

[0073] The present invention also relates to electronic devices comprising organic electronic devices according to the present invention, including but not limited to: display devices, lighting devices, light sources, sensors, etc.

[0074] The present invention will now be described in conjunction with preferred embodiments, but the present invention is not limited to the following embodiments. It should be understood that the appended claims summarize the scope of the present invention. Under the guidance of the inventive concept, those skilled in the art should realize that any changes made to the various embodiments of the present invention will be covered by the spirit and scope of the claims of the present invention. Specific Implementation Examples of the synthesis methods of the compounds described in this application are provided, but this application is not limited to the following examples.

[0076] Synthesis of intermediate A: .

[0077] Synthesis of intermediate b Compound a (10 mmol), pinacol diborate (12 mmol), Pd(dppf)3Cl2 (0.1 mmol), and potassium acetate (30 mmol) were dissolved in 1,4-dioxane and stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling the reaction system to room temperature, a portion of the solvent was removed by rotary evaporation, followed by extraction three times with dichloromethane and water. After separation, the organic phase was evaporated to dryness to obtain the crude product. The crude product was purified by column chromatography to obtain intermediate b in 83% yield. The mass spectrometry result of the product was m / z[H+] = 334.

[0078] Synthesis of intermediate A Intermediate b (10 mmol), compound c (10 mmol), Pd(PPh3)4 (0.1 mmol), and potassium carbonate (30 mmol) were dissolved in a mixed solvent of toluene, ethanol, and water, and the solution was dissolved in 100 mL of nitrogen gas. o Stirring at C for 12 h. After cooling the reaction system to room temperature, a portion of the solvent was removed using a rotary evaporator, followed by extraction three times with dichloromethane and water. After separation, the organic phase was evaporated to dryness to obtain the crude product. The crude product was purified by column chromatography to obtain intermediate A in 84% yield. The mass spectrometry result of the product was m / z[H+]=319.

[0079] Synthesis of intermediate B: Intermediate B was synthesized following the same steps as intermediate A, with a yield of 81%. Mass spectrometry m / z [H] + =352.

[0080] Example 1 Synthesis of Compound M1 .

[0081] Synthesis of compound M1: Intermediate A (10 mmol), intermediate 1-1 (10 mmol), Pd132 (0.1 mmol), X-Phos (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in xylene and stirred at 140 °C for 12 h under a nitrogen atmosphere. After cooling the reaction mixture to room temperature, a portion of the solvent was removed by rotary evaporation. The mixture was then extracted three times with dichloromethane and water. The organic phase was evaporated to dryness to obtain the crude product. Further purification by column chromatography yielded compound M1, with a yield of 81%. Mass spectrometry m / z [H + = 637. Elemental analysis results: C, 90.42; H, 4.92; N, 2.23; O, 2.48.

[0082] The following compounds were prepared using the same method as in Example 1. The structures, starting materials, and relevant synthetic information for each example are shown in Table 1 below. Table 1

[0083] Comparative Example This application also provides comparative examples 1 and 2, denoted as "Ref-01 to Ref-02", with the following chemical structural formulas: .

[0084] Fabrication and characterization of OLED devices The following detailed examples illustrate the fabrication method and process of OLED devices using the compounds described in this application. In the following OLED device fabrication method, ITO conductive glass is used as the anode substrate, PD as the hole injection material, HT as the hole transport material, Host as the host material of the light-emitting layer, Dopant as the doping material of the light-emitting layer, HB as the hole blocking material, ET and Liq as electron transport materials, Liq as the electron injection material, and Al as the cathode material. Furthermore, compound M1 from the aforementioned synthesis example is used as the light-emitting auxiliary material to fabricate corresponding OLED devices. The chemical structural formulas of PD, HT, Host, Dopant, ET, and Liq are shown below: .

[0085] The fabrication process of the OLED device using the above-mentioned materials is described in detail below through specific embodiments. In this embodiment, the structure of the fabricated OLED device is as follows: ITO / PD:HT (3:97, 10 nm) / HT (130 nm) / compound M1 of the present invention (10 nm) / Host:Dopant (3%, 20 nm) / ET:Liq (5:5, 30 nm) / Liq (1 nm) / Al (100 nm). Taking the fabrication method of compound M1 as the light-emitting auxiliary material for OLED device fabrication as an example, the fabricated OLED device is denoted as "OLED-1 device". The fabrication method of OLED-1 device includes the following steps: a. Cleaning of conductive glass substrate: Cleaning is performed using chloroform, ketone, and isopropanol, followed by ultraviolet ozone plasma treatment; b. Functional layer fabrication: First, the ITO substrate is transferred into a vacuum vapor deposition apparatus and deposited under high vacuum (1×10⁻⁶). -6 At millibars, resistance heating was used for evaporation at 1 Å s. -1 Hole implantation materials PD and HT were deposited on ITO at a deposition rate of 3:97, resulting in a hole implantation layer with a thickness of 10 nm. Then, at a deposition rate of 1.5 Å s⁻¹... -1 Hole transport material HT was deposited on the hole injection layer at a deposition rate of 1 Å s to obtain a hole transport layer with a thickness of 130 nm. Then, at a deposition rate of 1 Å s... -1 The compound M1 provided in the above embodiments was deposited on the hole transport layer at a deposition rate of 1 Å / s to obtain a light-emitting auxiliary layer with a thickness of 10 nm. Next, Host and Dopant were deposited on the light-emitting auxiliary layer at a deposition rate of 1 Å / s, with a deposition rate ratio of 97:3, to obtain a light-emitting layer with a thickness of 20 nm. Subsequently, in a vacuum chamber, electron transport materials ET and Liq were placed in different evaporation crucibles and subjected to high vacuum (1 × 10⁻⁶) conditions. -6 At a weight ratio of 5:5, ET and Liq were co-deposited at a density of 1 Å / s to form a 30 nm thick electron transport layer on the luminescent layer. Then, at 1 Å / s... -1 Electron injection material Liq was deposited on the electron transport layer at a deposition rate of 1 Å s⁻¹, resulting in an electron injection layer with a thickness of 1 nm. Then, at a deposition rate of 1 Å s⁻¹... -1 The cathode material Al was deposited on the electron injection layer at a certain evaporation rate to obtain a cathode with a thickness of 100 nm.

[0086] c. Encapsulation: The device is encapsulated in a nitrogen glove box using ultraviolet-cured resin to obtain the final OLED device.

[0087] Referring to the fabrication method of OLED-1, compounds synthesized in the examples were selected as luminescent auxiliary materials for OLED devices, and OLED-2 to OLED-34 devices were fabricated accordingly. It is understood that, in the fabrication methods of OLED-1 to OLED-34 devices, all experimental conditions are the same except for the luminescent auxiliary materials.

[0088] Furthermore, referring to the fabrication method of the device examples, comparative compounds Ref-01 and Ref-02 were used as luminescent auxiliary materials to prepare comparative OLED-Ref-01 and OLED-Ref-02 devices, respectively. Compared with the fabrication method of OLED-1 device, the experimental conditions are the same for OLED-Ref-01 and OLED-Ref-02 devices except for the luminescent auxiliary materials.

[0089] In this application, the current-voltage (ND) of OLED-1 to OLED-34, OLED-Ref-01 and OLED-Ref-02 devices are described. J-V The characteristics were characterized, and important parameters such as luminous efficiency and lifetime were recorded, as shown in Table 2. Luminous efficiency is defined as the value at a current density of 10 mA cm⁻¹. -2 The relative value obtained at that time. The lifetime (LT95) of the device is at 50 mA cm⁻¹. -2 Current, at 1000 nits brightness, the time it takes for the brightness to drop to 95% of the initial brightness.

[0090] Table 2

[0091] Table 1 shows that when the organic compounds in Examples 1 to 34 of this invention are used as red light emitting auxiliary materials, the prepared OLED devices (OLED-1 to OLED-34) are significantly superior to the control devices OLED-Ref-01 and OLED-Ref-02 in terms of luminous efficiency and lifetime, and also have lower driving voltages. This indicates that the aromatic amine compounds constructed using oxyphenanthrene and naphthalene as the core of this invention can achieve significant advantages when used as red light emitting auxiliary materials, and have broad application prospects.

[0092] The above provides a detailed description of the aromatic amine organic compounds, mixtures, compositions, and organic electronic devices provided in the embodiments of this application. Specific examples have been used to illustrate the principles and implementation methods of this application. The descriptions of the above embodiments are only for the purpose of helping to understand the methods and core ideas of this application. At the same time, for those skilled in the art, there will be changes in the specific implementation methods and application scope based on the ideas of this application. Therefore, the content of this specification should not be construed as a limitation of this application.

Claims

1. An arylamine-based organic compound, characterized by, The chemical formula of the arylamine-based organic compound is shown in general formula (1): Formula (1); wherein, L1and L2are each independently selected from a single bond, a substituted or unsubstituted C 6-30 an aryl group, a substituted or unsubstituted C 5-30 at least one of a heteroaryl group, a substituted or unsubstituted C Ar1and Ar2are each independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted C 6-30 an aromatic group, a substituted or unsubstituted C 5-30 at least one of a heteroaromatic group; L1, L2, Ar1and Ar2are selected from at least one of a hydrogen atom, a C 1-15 alkyl group, a C 6-30 aromatic group, and a heteroaromatic group; 5-30 aromatic group, and a heteroaromatic group; In L1, L2, Ar1, and Ar2, the heteroatom in the heteroaromatic group is independently selected from at least one of a nitrogen atom, an oxygen atom, and a sulfur atom; The expression of the ring structure with a dash across it represents a connection point at any bondable position on the ring structure.

2. The arylamine organic compound according to claim 1, characterized by, L1and L2are each independently selected from at least one of a single bond, a substituted or unsubstituted group: 。 3. The arylamine organic compound according to claim 1, characterized by, Ar1and Ar2are each independently selected from at least one of a hydrogen atom, a substituted or unsubstituted group: " indicates the connection site.​ 4. The arylamine organic compound according to claim 1, characterized by, In L1, L2, Ar1, and Ar2, the substituent group in the substituted or unsubstituted group is independently selected from a deuterium atom, a methyl group, a tert-butyl group, an adamantyl group, a phenyl group, a biphenyl group, a naphthyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a fluorenyl group, or a carbazolyl group.

5. The arylamine organic compound according to claim 1, wherein The chemical formula of the arylamine-based organic compound is selected from general formula (2-1) or general formula (2-2): Formula (2-1); Formula (2-2).

6. The arylamine organic compound according to claim 1, wherein The chemical formula of the arylamine-based organic compound is selected from general formula (3-1) or general formula (3-2): Formula (3-1); Formula (3-2).

7. The arylamine organic compound according to claim 1, wherein The chemical formula of the arylamine-based organic compound is selected from at least one of the following structures: 。 8. A mixture characterized in that, The composition comprises at least one arylamine-based organic compound according to any one of claims 1 to 7, and at least one organic functional material, which includes at least one of a hole injection material, a hole transport material, a light-emitting auxiliary material, an electron transport material, an electron injection material, an electron blocking material, a hole blocking material, an organic light-emitting guest material, and an organic host material.

9. A composition characterized in that, The composition comprises at least one organic solvent and at least one arylamine-based organic compound according to any one of claims 1 to 7, or the composition comprises at least one organic solvent and the mixture according to claim 8.

10. An organic electronic device, characterized in that An organic electroluminescence device comprising a first electrode, a second electrode, and a functional layer between the first electrode and the second electrode, wherein the functional layer comprises an arylamine-based organic compound according to any one of claims 1 to 9 or the mixture according to claim 8, or the composition according to claim 9.

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