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

Abstract

The invention discloses an organic compound, a mixture, a composition, an organic electronic device and a display panel. The structural general formula of the organic compound is as shown in formula (1). The organic compound provided by the invention has relatively good transmission and charge balance adjusting performance; the compound can be applied to organic electronic devices as a light-emitting auxiliary material to improve the light-emitting efficiency and prolong the service life of the devices, and meanwhile, the devices can keep relatively low driving voltage.

Description

Technical Field

[0001] This application relates to the field of display technology, specifically to an organic compound, mixture, composition, organic electronic device, and display panel. Background Technology

[0002] Organic light-emitting diode (OEL) technology utilizes the photoelectric properties of organic materials to directly convert electrical energy into light energy. Organic electronic devices based on this technology generally consist of an anode, a cathode, and multiple organic functional layers. These layers include hole injection layers, hole transport layers, light-emitting auxiliary layers, light-emitting layers, electron transport layers, and electron injection layers, each containing specific organic materials designed to enhance the overall performance of the device. When a voltage is applied between the anode and cathode, holes are injected from the anode and electrons from the cathode, combining to form excitons. These excitons release light energy as they return to their ground state. As a typical representative of OEL technology, organic light-emitting diodes (OLEDs) have shone brightly in the flat panel display and lighting fields due to their numerous advantages, including self-illumination, high brightness, high efficiency, low voltage, wide viewing angle, and high contrast. Their wide viewing angle, fast response, low voltage requirements, and ultra-thin design fully demonstrate the enormous potential and broad application prospects of OLED technology in the future.

[0003] The selection and design of luminescent auxiliary materials play a crucial role in improving the luminous efficiency and extending the lifespan of OLED devices. Carefully designed luminescent auxiliary materials can effectively balance carrier transport in OLED devices, strongly suppress electron back migration, and promote electron-hole recombination primarily in the central region of the emissive layer, reducing non-radiative exciton recombination, thereby improving luminous efficiency and extending lifespan. Therefore, developing more efficient novel luminescent auxiliary materials to further optimize the balance of hole and electron transport within the device is key to improving device efficiency and lifespan while maintaining a low driving voltage. This challenge is an urgent issue for researchers in this field to address. Summary of the Invention

[0004] This application provides an organic compound, mixture, composition, organic electronic device, and display panel. The organic compound has good properties for transporting and regulating charge balance, and can be used as a light-emitting auxiliary material in organic electronic devices to improve the luminous efficiency and lifespan of the devices, while maintaining a low driving voltage.

[0005] To achieve the above objectives, according to a first aspect of this application, an organic compound is provided, the general structural formula of which is shown in formula (1):

[0006]

[0007] Where X is selected from oxygen atom, sulfur atom or C-(CH3)2;

[0008] R is selected from hydrogen atom, phenyl or naphthyl;

[0009] L1 is selected from at least one of a single bond, 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] Ar is selected from at least one of 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;

[0011] The heteroatom in the heteroaromatic group is selected from one or more of nitrogen, oxygen, or sulfur atoms; the substituted or unsubstituted substituent group is selected from methyl, deuterated methyl, tert-butyl, adamantane, phenyl, biphenyl, naphthyl, fluorenyl, dibenzofuranyl, or dibenzothiopheneyl.

[0012] In the structure shown in formula (1), at least one hydrogen atom in the groups other than X is not substituted or is substituted by a deuterium atom.

[0013] According to a second aspect of this application, a mixture is provided, the mixture comprising at least one or more of the organic compounds described above and at least one organic functional material, the organic functional material being selected from at least one of hole injection materials, hole transport materials, light-emitting auxiliary materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, organic light-emitting guest materials, and organic host materials.

[0014] According to a third aspect of this application, a composition is provided, the composition comprising at least one organic solvent and at least one of the organic compounds described above, or the composition comprising at least one organic solvent and a mixture described above.

[0015] According to a fourth aspect of this application, an organic electronic device is provided, the organic electronic device comprising:

[0016] First electrode;

[0017] An organic functional layer is disposed on one side of the first electrode;

[0018] The second electrode is disposed on the side of the organic functional layer away from the first electrode;

[0019] The organic functional layer is made of at least one of the organic compounds or mixtures described above, or the organic functional layer is prepared from the composition described above.

[0020] According to a fifth aspect of this application, a display panel is provided, the display panel comprising the organic electronic devices described above.

[0021] In the organic compounds, mixtures, compositions, organic electronic devices, and display panels provided in this application, the organic compound represented by formula (1) is a deuterated triarylamine compound containing a bis-naphthalene structure and a dibenzo5-membered ring structure. This organic compound has significant advantages as a hole transport material in organic electronic devices. The introduction of the bis-naphthalene structure enhances the conjugation effect and steric hindrance of the organic compound molecules, enabling the organic compound material to maintain a stable film morphology at high temperatures during film formation and suppressing crystallization, thus improving film stability. Furthermore, the combination of the nitrogen atom in the triarylamine framework with the electron acceptor properties of the bis-naphthalene structure optimizes the HOMO and T1 energy levels of the organic compound material, facilitating hole injection and transport, balancing carrier transport and exciton confinement, thereby improving the device's luminous efficiency. The introduction of deuterium atoms helps suppress molecular vibrational frequencies, reduces intramolecular energy dissipation, lowers the energy required for electron transitions, and helps reduce the driving voltage required for device operation. Simultaneously, the high bond energy of deuterium atoms makes the organic compound molecules containing deuterium atoms more stable, thus increasing the device's lifespan. Therefore, when the organic compounds provided in this application are used in organic electronic devices as red light emitting auxiliary materials, the driving voltage of the devices can be significantly reduced, while the luminous efficiency and lifespan of the devices can be effectively improved. Attached Figure Description

[0022] To more clearly illustrate the technical solutions in the embodiments of this application, 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 this application. For those skilled in the art, other drawings can be obtained based on these drawings without creative effort.

[0023] Figure 1 This is a schematic diagram of the structure of an organic electronic device provided in an embodiment of this application.

[0024] Figure 2 This is the 1H NMR spectrum of compound M11 synthesized in the embodiments of this application.

[0025] Reference numerals: 100, Organic light-emitting device; 1, Substrate; 11, First electrode; 12, Hole injection layer; 13, Hole transport layer; 14, Light-emitting auxiliary layer; 15, Organic light-emitting layer; 16, Electron transport layer; 17, Electron injection layer; 18, Second electrode. Detailed Implementation

[0026] 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.

[0027] In this application, "substitution" means that the hydrogen atom in the substituent is replaced by the substituent.

[0028] In this application, hydrogen atoms include isotopes with different numbers of neutrons, namely protium, deuterium, and tritium.

[0029] In this application, "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.

[0030] In this application, "ring atom number" refers to the number of atoms in the ring itself of a structural compound (e.g., a monocyclic compound, a fused-ring compound, a cross-linked compound, a carbocyclic compound, or a heterocyclic compound) obtained by atomic bonding to form a ring. When the ring is substituted by a substituent, the atoms contained in the substituent are not included in the ring-forming atoms. The same applies to the "ring atom number" described below unless otherwise specified. For example, a benzene ring has 6 ring atoms, a naphthalene ring has 10 ring atoms, and a thiophene group has 5 ring atoms.

[0031] In this application, "aryl or aromatic group" refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removing one hydrogen atom. This group can be monocyclic, fused-ring, or polycyclic, and for polycyclic rings, at least one is an aromatic ring system. For example, "substituted or unsubstituted aryl group having 5 to 25 ring atoms" refers to an aryl group containing 5 to 25 ring atoms, optionally further substituted; suitable examples include, but are not limited to: benzene, biphenyl, terphenyl, naphthalene, anthracene, fluoranthene, phenanthrene, benzo[a]phenanthrene, dinaphthalene, tetraphenyl, pyrene, benzo[a]pyrene, acenaphthene, fluorene, and their derivatives. Understandably, 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 acenaphthene, fluorene, or 9,9-diarylfluorene, triarylamines, and diaryl ether systems should also be included in the definition of aryl.

[0032] In this application, the heteroaromatic group having 5 to 25 ring atoms refers to a monovalent group comprising a carbocyclic aromatic system having at least one heteroatom selected from nitrogen, oxygen, phosphorus, sulfur, or silicon as a cyclic atom and 5 to 25 ring atoms. Non-limiting examples of heteroaromatic groups with 5 to 25 ring atoms may include furanyl, thiophene, pyrrole, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1 3,4-Thiadiazolyl, 1,2,5-Thiadiazolyl, Tetrazolyl, Pyridyl, Pyrimidinyl, Pyridazinyl, 1,2,3-Triazinyl, 1,2,4-Triazinyl, 1,3,5-Triazinyl, Benzofuranyl, Benzoisofuranyl, Benzothiophenyl, Benzoisothiophenyl, Indolyl, Isoyndolyl, Inzazoleyl, Benzimidazolyl, Benzooxazolyl, Benzoisooxazolyl, Benzothiazolyl 2,1,3-Benzoxadiazole, Quinolinyl, Isoquinolinyl, Trinolinyl, Phtharazineyl, Quinazolinyl, Quinolinyl, Naphridinyl, Benzotriazinyl, Benzooxazinyl, Purineyl, Pteridinyl, Inazinyl, Benzothiazinyl, Acridineyl, Phenyrazinyl, Phenyraziazinyl, Phenyoxazinyl, Dibenzofuranyl, Dibenzothiopheneyl, Carbazoleyl, Naphridfuranyl, Quinolinyl, Isoquinolinyl, Indole[1,2-f]phenanthrene The group includes, but is not limited to, pyridyl, 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, etc., as well as aromatic composite groups with heteroatoms.

[0033] In this application, the "*" connected to a single bond indicates a connection or fusion site.

[0034] In this application, when no linking site is specified in the group, it means that any linkable site in the group is selected as the linking site.

[0035] In this application, the single bond connecting the substituents extends through the corresponding ring, indicating that the substituent can be attached to any position on the ring, for example... R is attached to any substituted site on the benzene ring.

[0036] This application provides an organic compound, the general structural formula of which is shown in formula (1):

[0037]

[0038] Where X is selected from oxygen atom, sulfur atom or C-(CH3)2;

[0039] R is selected from hydrogen atom, phenyl or naphthyl;

[0040] L1 is selected from at least one of a single bond, 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;

[0041] Ar is selected from at least one of 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;

[0042] The heteroatom in the heteroaromatic group is selected from one or more of nitrogen, oxygen, or sulfur atoms; the substituted or unsubstituted substituent group is selected from methyl, deuterated (D)methyl, tert-butyl, adamantane, phenyl, biphenyl, naphthyl, fluorenyl, dibenzofuranyl, or dibenzothiopheneyl.

[0043] In the structure shown in formula (1), at least one hydrogen atom in the groups other than X is not substituted or is substituted by a deuterium atom.

[0044] Understandably, when X is selected from C-(CH3)2, the hydrogen atom on X is not replaced by a deuterium atom; in the structure shown in formula (1), apart from the hydrogen atom on X, none of the other hydrogen atoms are replaced or are replaced by a deuterium atom.

[0045] It should be noted that in the structure shown in equation (1), the way “—” crosses the structure indicates that the connection point is located at any position on the structure where bonding can occur.

[0046] In some embodiments, L1 is selected from single bond, phenyl, biphenyl, naphthyl, fluorenyl, dibenzofuranyl, dibenzothiophenyl, or carbazoyl, and at least one hydrogen atom in L1 is not substituted or is substituted by a deuterium atom.

[0047] In some embodiments, Ar is selected from any of the following groups:

[0048]

[0049] In this context, "*" represents a connection site; at least one hydrogen atom in Ar is not substituted or is substituted by a deuterium atom.

[0050] In some embodiments, the organic compound is selected from any one of the following compounds:

[0051]

[0052]

[0053]

[0054]

[0055]

[0056]

[0057]

[0058]

[0059]

[0060]

[0061]

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081] It should be noted that in the organic compounds listed above, "D" represents deuterium atoms, and the number after "D" indicates the number of deuterium atoms.

[0082] For example, compounds In this context, D5 represents 5 deuterium atoms, and indicates that all 5 hydrogen atoms on the corresponding benzene ring are replaced by deuterium atoms.

[0083] In some embodiments, the organic compounds provided in this application can be used as organic functional materials in electronic devices, particularly in OLED devices. Organic functional materials can be categorized into hole injection materials (HIM), hole transport materials (HTM), prime materials, electron transport materials (ETM), electron injection materials (EIM), electron blocking materials (EBM), hole blocking materials (HBM), guest emitting materials, and host emitting materials. Host materials can be further categorized into phosphorescent host materials, fluorescent host materials, and host materials for thermally activated delayed fluorescence (TADF) emitting materials. The organic compounds provided in this application can be any one of these.

[0084] In a preferred embodiment, the organic compound represented by formula (1) provided in this application can be used as a luminescent auxiliary material.

[0085] In some embodiments, the glass transition temperature (Tg) of the organic compound provided in this application is ≥100℃; in a preferred embodiment, Tg is ≥120℃; in a more preferred embodiment, Tg is ≥140℃; in a more preferred embodiment, Tg is ≥160℃; and in a most preferred embodiment, Tg is ≥180℃.

[0086] This application also provides a polymer, wherein the monomers of the polymer include organic compounds represented by formula (1).

[0087] This application also provides a mixture comprising at least one organic compound of formula (1) and at least one organic functional material selected from at least one of hole injection materials, hole transport materials, luminescent auxiliary materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, organic luminescent guest materials, organic host materials, and inorganic quantum dots. For example, various organic functional materials are described in detail in WO2010135519A1, US20090134784A1, and WO2011110277A1. The entire contents of these three patent documents are hereby incorporated herein by reference. The organic functional material can be a small molecule or a polymer material.

[0088] The organic compounds provided in this application can be applied to vapor-deposited OLED devices. For example, in some embodiments, the molecular weight of the organic compounds provided in this application is ≤1100 g / mol; in a preferred embodiment, the molecular weight of the organic compounds provided in this application is ≤1000 g / mol; in a more preferred embodiment, the molecular weight of the organic compounds provided in this application is ≤950 g / mol; in a more preferred embodiment, the molecular weight of the organic compounds provided in this application is ≤900 g / mol; and in a most preferred embodiment, the molecular weight of the organic compounds provided in this application is ≤800 g / mol.

[0089] The organic compounds provided in this application can also be used in printed OLED devices. For example, in some embodiments, the molecular weight of the organic compounds provided in this application is ≥500 g / mol; in a more preferred embodiment, the molecular weight of the organic compounds provided in this application is ≥700 g / mol; in a more preferred embodiment, the molecular weight of the organic compounds provided in this application is ≥900 g / mol; and in a most preferred embodiment, the molecular weight of the organic compounds provided in this application is ≥1000 g / mol.

[0090] This application also provides a composition comprising at least one organic solvent and at least one organic compound of formula (1), or the composition comprising at least one organic solvent and the mixture.

[0091] The organic solvent may be selected from any one or a mixture of two or more solvents selected from aromatic or heteroaromatic compounds, esters, aromatic ketones or aromatic ethers, aliphatic ketones or aliphatic ethers, alicyclic or olefinic compounds, borate esters or phosphate esters. Preferably, the organic solvent is selected from solvents based on aromatic or heteroaromatic compounds.

[0092] 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.

[0093] 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.

[0094] 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.

[0095] 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, pentanyl ether, hexane 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.

[0096] 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.

[0097] In some preferred embodiments, the compositions provided in this application comprise at least one organic compound or polymer or mixture as described above, at least one organic solvent, and at least one cosolvent. Examples of the cosolvent include (but are not limited to): methanol, ethanol, 2-methoxyethanol, dichloromethane, 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.

[0098] In some embodiments, solvents particularly suitable for this application are those with Hansen solubility parameters in the range of δd (dispersion force) of 17.0–23.2 MPa. 1 / 2The range, especially in the range of 18.5–21.0 MPa 1 / 2 The range; δp (polar force) is 0.2–12.5 MPa. 1 / 2 The range, especially 2.0–6.0 MPa 1 / 2 The range; δh (hydrogen bond force) is in the range of 0.9–14.2 MPa. 1 / 2 The range, especially 2.0–6.0 MPa 1 / 2 The range.

[0099] In the compositions provided in 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 ≥150°C; preferably, it is ≥180°C; more preferably, it is ≥200°C; more preferably, it is ≥250°C; and most preferably, it is ≥275°C or ≥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.

[0100] In some embodiments, the composition provided in this application is a solution. In another embodiment, the composition provided in this application is a suspension.

[0101] The compositions provided in this application may include 0.01 wt% to 10 wt% of the organic compound or the mixture. Preferably, the mass fraction of the organic compound or the mixture in the composition ranges from 0.1 wt% to 15 wt%. More preferably, the mass fraction of the organic compound or the mixture in the composition ranges from 0.2 wt% to 5 wt%. Most preferably, the mass fraction of the organic compound or the mixture in the composition ranges from 0.25 wt% to 3 wt%.

[0102] In some embodiments, the organic compound or the mixture in the composition has a mass fraction of 0.01%, 0.05%, 0.1%, 0.15%, 0.2%, 0.25%, 0.3%, 0.35%, 0.4%, 0.45%, 0.5%, 0.6%, 0.7%, 0.8%, 0.9%, 1%, 3%, 5%, 8%, 10%, 12%, or 15%.

[0103] This application also provides an example of the use of the composition as a coating or printing ink in the preparation of organic electronic devices. A particularly preferred use is to use the composition as a coating or printing ink to prepare organic electronic devices by printing or coating methods.

[0104] 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.

[0105] The organic compounds, mixtures, or compositions provided in this application can be used in organic electronic devices.

[0106] The organic electronic devices include, but are not limited to, organic light-emitting diodes (OLEDs), organic photovoltaic cells (OPVs), organic light-emitting electrochemical cells (OLEECs), organic field-effect transistors (OFETs), organic light-emitting field-effect transistors (OLEFETs), organic lasers, organic spintronic devices, organic sensors, and organic plasmon emitting diodes (OPEDs). Preferably, the organic electronic devices are organic electroluminescent devices, such as OLEDs, OLEECs, or OLEFETs.

[0107] In this embodiment of the application, the organic compound is preferably applied to the light-emitting auxiliary layer of the OLED device.

[0108] like Figure 1 As shown, embodiments of this application also provide an organic electronic device 100, which is an organic light-emitting device, and the organic electronic device 100 includes a first electrode 11, a second electrode 18 disposed opposite to the first electrode 11, and an organic functional layer located between the first electrode 11 and the second electrode 18. The material of the organic functional layer includes at least one of the organic compounds represented by the above formula (1), or the material of the organic functional layer includes the mixtures described above, or the organic functional layer is prepared using the organic compounds, mixtures or compositions described above.

[0109] In one specific embodiment, the first electrode 11 is the anode, and the second electrode 18 is the cathode.

[0110] Specifically, the organic functional layer is selected from at least one of a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, a light-emitting auxiliary layer, and an organic light-emitting layer. Preferably, the organic functional layer includes at least a light-emitting auxiliary layer and an organic light-emitting layer stacked together.

[0111] Specifically, the organic electronic device 100 also includes a substrate 1, and a first electrode 11 is disposed on the substrate 1.

[0112] In one specific embodiment, the organic functional layer includes a hole injection layer 12, a hole transport layer 13, a light-emitting auxiliary layer 14, an organic light-emitting layer 15, an electron transport layer 16, and an electron injection layer 17, which are sequentially stacked on the first electrode 11. The light-emitting auxiliary layer 14 is made of at least one organic compound represented by formula (1).

[0113] In some embodiments, the organic electronic device 100 includes any one of red light organic electronic devices, blue light organic electronic devices, and green light organic electronic devices. That is, the organic compound represented by formula (1) provided in the embodiments of this application can be used as a red light emitting auxiliary material, a blue light emitting auxiliary material, and a green light emitting auxiliary material.

[0114] It is understandable that the organic light-emitting layer in red organic electronic devices emits red light, the organic light-emitting layer in blue organic electronic devices emits blue light, and the organic light-emitting layer in green organic electronic devices emits green light.

[0115] In a preferred embodiment, the organic compound represented by formula (1) is a red light-emitting auxiliary material, and correspondingly, the light emitted by the organic light-emitting layer 15 is red light. Therefore, the organic compound represented by formula (1) can be preferably applied in red light organic electronic devices.

[0116] Specifically, the organic electronic device 100 includes, 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 (OLEFETs), organic lasers, organic spintronic devices, organic sensors, and organic plasmon emission diodes (OPEDs), with organic electroluminescent devices such as OLEDs, OLEECs, or OLEFETs being particularly preferred.

[0117] The anode of the organic electronic device 100 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 organic light-emitting layer. In some embodiments, 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 organic 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 some embodiments, the anode is patterned. Patterned ITO conductive substrates are commercially available and can be used to fabricate devices according to this application.

[0118] The cathode in this application embodiment 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 some embodiments, 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 organic 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 can be used as cathode materials for the devices of this 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.

[0119] In some embodiments, the light-emitting material in the organic light-emitting layer of the organic electronic device 100 provided in this application is selected from singlet light emitters, triplet light emitters, or TADF materials.

[0120] In some embodiments, the thickness of the organic functional layer in the organic electronic device 100 provided in this application ranges from 10 nm to 200 nm, preferably from 20 nm to 150 nm, more preferably from 30 nm to 100 nm, and most preferably from 40 nm to 90 nm.

[0121] The organic electronic device 100 provided in this application embodiment can be applied to various electronic devices, including but not limited to display devices, lighting devices, light sources, sensors, etc.

[0122] This application also provides an electronic device, which includes the organic electronic device 100 provided in this application embodiment. The electronic device includes, but is not limited to, display devices, lighting devices, light sources, sensors, etc.

[0123] This application embodiment also provides a display panel, which includes the organic electronic device 100 described above.

[0124] The present application will now be described in conjunction with preferred embodiments, but the scope of protection of the present application is not limited to the following embodiments. It should be understood that the appended claims summarize the scope of protection of the present application. 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 application will be covered by the spirit and scope of the claims of the present application.

[0125] (I) Specific Synthesis Examples

[0126] The organic compounds and their preparation methods described in this application are further illustrated below with specific synthetic examples. Unless otherwise specified, all raw materials used in the following examples are commercially available products.

[0127] Example 1

[0128] The synthetic route for compound M1 is shown below:

[0129]

[0130] Synthesis of intermediates 1-3:

[0131] Compounds 1-1 (10 mmol), 1-2 (10 mmol), Pd2(dba)3 (0.1 mmol), X-Phos (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene. The reaction system was heated to 120 °C and stirred 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. Then, the system was extracted three times with dichloromethane and water, and the organic phase was evaporated to dryness to obtain the crude product. Finally, the crude product was further purified by column chromatography to obtain intermediate 1-3 in 85% yield. The mass spectrometry results of the product were m / z [H]. + =435.

[0132] Synthesis of compound M1:

[0133] Intermediate 1-3 (10 mmol), compound 1-4 (10 mmol), Pd2(dba)3 (0.1 mmol), X-Phos (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene. The reaction system was heated to 120 °C and stirred for 9 h under a nitrogen atmosphere. After cooling the reaction system to room temperature, a portion of the solvent was removed by rotary evaporation. Then, the system was extracted three times with dichloromethane and water, and the organic phase was evaporated to dryness to obtain the crude product. Finally, the crude product was further purified by column chromatography to obtain compound M1 in 87% yield. The mass spectrometry results of the product were m / z [H]. + =516, elemental analysis results: C, 88.30; H, 5.81; N, 2.74; O, 3.13.

[0134] Example 2

[0135] The synthetic route for compound M2 is shown below:

[0136]

[0137] The synthesis of intermediates 2-3 followed the same method as that used for intermediates 1-3 described above. The yield of intermediates 2-3 was 88%, and the mass spectrometry results of the product were [m / z]. + =435.

[0138] The synthesis of compound M2 followed the same method as that used for compound M1. The yield of compound M2 was 89%, and the mass spectrometry results of the product were [m / z [H]]. + =516, elemental analysis results: C, 88.33; H, 5.82; N, 2.71; O, 3.12.

[0139] Example 3

[0140] The synthetic route for compound M3 is shown below:

[0141]

[0142] The synthesis of intermediate 3-3 followed the same method as intermediate 1-3 described above. The yield of intermediate 3-3 was 83%, and the mass spectrometry results of the product were [m / z]. + =435.

[0143] Compound M3 was synthesized using the same method as compound M1 described above. The yield of compound M3 was 85%, and the mass spectrometry results of the product were [m / z [H]]. + =516, elemental analysis results: C, 88.28; H, 5.78; N, 2.71; O, 3.18.

[0144] Example 4

[0145] The synthetic route for compound M4 is as follows:

[0146]

[0147] The synthesis of intermediate 4-3 followed the same method as intermediate 1-3 described above. The yield of intermediate 4-3 was 85%, and the mass spectrometry results of the product were [m / z [H]]. + =435.

[0148] Compound M4 was synthesized using the same method as compound M1 described above. The yield of compound M4 was 83%, and the mass spectrometry results of the product were [m / z [H]]. + =516, elemental analysis results: C, 88.29; H, 5.77; N, 2.77; O, 3.14.

[0149] Example 5

[0150] The synthetic route for compound M5 is as follows:

[0151]

[0152] The synthesis of intermediate 5-3 followed the same method as that used for intermediates 1-3 described above. The yield of intermediate 5-3 was 84%, and the mass spectrometry results of the product were [m / z]. + =451.

[0153] Compound M5 was synthesized using the same method as compound M1 described above. The yield of compound M5 was 85%, and the mass spectrometry results of the product were [m / z [H]]. + =532, elemental analysis results: C, 85.65; H, 5.64; N, 2.66; S, 6.01.

[0154] Example 6

[0155] The synthetic route for compound M6 is as follows:

[0156]

[0157] The synthesis of intermediate 6-3 followed the method described for intermediates 1-3 above. The yield of intermediate 6-3 was 88%, and the mass spectrometry results of the product were [m / z [H]]. + =461.

[0158] The synthesis of compound M6 followed the same method as that used for compound M1. The yield of compound M6 was 89%, and the mass spectra of the product were [m / z [H]]. + =542, elemental analysis results: C, 90.70; H, 6.64; N, 2.56.

[0159] Example 7

[0160] The synthetic route for compound M7 is as follows:

[0161]

[0162] The synthesis of intermediate 7-3 followed the method described for intermediates 1-3 above. The yield of intermediate 7-3 was 85%, and the mass spectrometry results of the product were [m / z]. + =461.

[0163] The synthesis of compound M7 followed the same method as that used for compound M1. The yield of compound M7 was 84%, and the mass spectrometry results of the product were [m / z [H]]. + =542, elemental analysis results: C, 90.71; H, 6.68; N, 2.52.

[0164] Example 8

[0165] The synthetic route for compound M8 is as follows:

[0166]

[0167] The synthesis of intermediate 8-3 followed the same method as intermediate 1-3 described above. The yield of intermediate 8-3 was 86%, and the mass spectrometry results of the product were [m / z [H]]. + =461.

[0168] The synthesis of compound M8 followed the same method as that used for compound M1 described above. The yield of compound M8 was 88%, and the mass spectrometry results of the product were [m / z [H]]. + =542, elemental analysis results: C, 90.73; H, 6.67; N, 2.55.

[0169] Example 9

[0170] The synthetic route for compound M9 is as follows:

[0171]

[0172] The synthesis of intermediate 9-3 followed the same method as intermediate 1-3 described above. The yield of intermediate 9-3 was 85%, and the mass spectrometry results of the product were [m / z [H]]. + =461.

[0173] The synthesis of compound M9 followed the same method as that used for compound M1. The yield of compound M9 was 87%, and the mass spectrometry results of the product were [m / z [H]]. + =542, elemental analysis results: C, 90.82; H, 6.60; N, 2.54.

[0174] Example 10

[0175] The synthetic route for compound M10 is as follows:

[0176]

[0177] The synthesis of intermediate 10-3 followed the method described above for intermediate 1-3. The yield of intermediate 10-3 was 83%, and the mass spectrometry results of the product were [m / z]. + =435.

[0178] The synthesis of compound M10 followed the same method as that used for compound M1. The yield of compound M10 was 85%, and the mass spectrometry results of the product were [m / z [H]]. + =516, elemental analysis results: C, 88.28; H, 5.78; N, 2.71; O, 3.18.

[0179] Example 11

[0180] The synthetic route for compound M11 is as follows:

[0181]

[0182] The synthesis of intermediate 11-3 followed the method described above for the synthesis of intermediate 1-3. The yield of intermediate 11-3 was 82%, and the mass spectrometry results of the product were [m / z]. + =437.

[0183] The synthesis of compound M11 followed the method described above for the synthesis of compound M1. The yield of compound M11 was 85%, and the mass spectrometry results of the product were [m / z [H]]. + The product has a molecular weight of 618, and its elemental analysis results are as follows: C, 91.92; H, 5.70; N, 2.24. The product's 1H NMR spectrum is shown below. Figure 2 As shown.

[0184] Example 12

[0185] The synthetic route for compound M12 is as follows:

[0186]

[0187] Synthesis of intermediate 12-2:

[0188] Compounds 12-2-1 (10 mmol), 12-2-2 (10 mmol), Pd(PPh3)4 (0.1 mmol), and potassium carbonate (30 mmol) were dissolved in toluene, ethanol, and water. The reaction system was heated to 120 °C and stirred for 10 h under a nitrogen atmosphere. After cooling the reaction system to room temperature, some of the solvent was removed by rotary evaporation. Then, the system was extracted three times with dichloromethane and water, and the organic phase was evaporated to dryness to obtain the crude product. Finally, the crude product was further purified by column chromatography to obtain intermediate 12-2 in 89% yield. The mass spectrometry results of the product were [m / z [H]]. + =370.

[0189] The synthesis of intermediate 12-3 followed the method described above for the synthesis of intermediate 1-3. The yield of intermediate 12-3 was 85%, and the mass spectrometry results of the product were [m / z [H]]. + =587.

[0190] The synthesis of compound M12 followed the same method as that used for compound M1. The yield of compound M12 was 82%, and the mass spectrometry results of the product were [m / z [H]]. + =668, elemental analysis results: C, 92.24; H, 5.65; N, 2.10.

[0191] Example 13

[0192] The synthetic route for compound M13 is as follows:

[0193]

[0194] The synthesis of intermediate 13-3 followed the method described above for the synthesis of intermediate 1-3. The yield of intermediate 13-3 was 86%, and the mass spectrometry results of the product were [m / z]. + =461.

[0195] The synthesis of compound M13 followed the same method as that used for compound M1. The yield of compound M13 was 81%, and the mass spectrometry results of the product were [m / z [H]]. + =542, elemental analysis results: C, 90.77; H, 6.63; N, 2.50.

[0196] Example 14

[0197] The synthetic route for compound M14 is as follows:

[0198]

[0199] The synthesis of intermediate 14-3 followed the same method as intermediate 1-3 described above. The yield of intermediate 14-3 was 88%, and the mass spectrometry results of the product were [m / z [H]].+ =461.

[0200] The synthesis of compound M14 followed the same method as that used for compound M1. The yield of compound M14 was 86%, and the mass spectrometry results of the product were [m / z [H]]. + =542, elemental analysis results: C, 90.73; H, 6.67; N, 2.55.

[0201] Example 15

[0202] The synthetic route for compound M15 is as follows:

[0203]

[0204] The synthesis of intermediate 15-3 followed the method described above for intermediate 1-3. The yield of intermediate 15-3 was 84%, and the mass spectrometry results of the product were [m / z [H]]. + =437.

[0205] The synthesis of compound M15 followed the same method as that used for compound M1. The yield of compound M15 was 87%, and the mass spectrometry results of the product were [m / z [H]]. + = 618, elemental analysis results: C, 91.93; H, 5.73; N, 2.20.

[0206] Example 16

[0207] The synthetic route for compound M16 is as follows:

[0208]

[0209] The synthesis of intermediate 16-3 followed the method described above for intermediate 1-3. The yield of intermediate 16-3 was 85%, and the mass spectrometry results of the product were [m / z [H]]. + =437.

[0210] The synthesis of compound M16 followed the same method as that used for compound M1. The yield of compound M16 was 83%, and the mass spectrometry results of the product were [m / z]. + = 618, elemental analysis results: C, 91.90; H, 5.71; N, 2.23.

[0211] Example 17

[0212] The synthetic route for compound M17 is as follows:

[0213]

[0214] The synthesis of intermediate 17-3 followed the method described for intermediate 12-2 above. The yield of intermediate 17-3 was 82%, and the mass spectrometry results of the product were [m / z [H]]. + =325.

[0215] The synthesis of intermediate 17-3 followed the method described for intermediate 1-3 above. The yield of intermediate 17-3 was 82%, and the mass spectrometry results of the product were [m / z [H]]. + =542.

[0216] The synthesis of compound M17 followed the same method as that used for compound M1. The yield of compound M17 was 85%, and the mass spectrometry results of the product were [m / z [H]]. + = 618, elemental analysis results: C, 91.90; H, 5.73; N, 2.28.

[0217] Example 18

[0218] The synthetic route for compound M18 is as follows:

[0219]

[0220] The synthesis of intermediate 18-3 followed the method described above for intermediate 1-3. The yield of intermediate 18-3 was 84%, and the mass spectrometry results of the product were [m / z]. + =467.

[0221] The synthesis of compound M18 followed the same method as that used for compound M1. The yield of compound M18 was 88%, and the mass spectrometry results of the product were [m / z [H]]. + =549, elemental analysis results: C, 90.70; H, 6.69; N, 2.57.

[0222] Example 19

[0223] The synthetic route for compound M19 is as follows:

[0224]

[0225] The synthesis of intermediate 19-3 followed the method described for intermediate 1-3 above. The yield of intermediate 19-3 was 85%, and the mass spectrometry results of the product were [m / z [H]]. + =468.

[0226] The synthesis of compound M19 followed the same method as that used for compound M1. The yield of compound M19 was 83%, and the mass spectrometry results of the product were [m / z [H]]. + =558, elemental analysis results: C, 91.40; H, 6.01; N, 2.57.

[0227] Example 20

[0228] The synthetic route for compound M20 is as follows:

[0229]

[0230] The synthesis of intermediate 20-3 followed the method described for intermediates 1-3 above. The yield of intermediate 20-3 was 82%, and the mass spectrometry results of the product were [m / z [H]]. + =468.

[0231] The synthesis of compound M20 followed the same method as that used for compound M1. The yield of compound M20 was 88%, and the mass spectrometry results of the product were [m / z [H]]. + = 641, elemental analysis results: C, 89.90; H, 5.30; N, 2.20; O, 2.57.

[0232] Example 21

[0233] The synthetic route for compound M21 is as follows:

[0234]

[0235]

[0236] The synthesis of intermediate 21-2 followed the same method as intermediate 12-2 described above. The yield of intermediate 21-2 was 83%, and the mass spectrometry results of the product were [m / z [H]]. + =325.

[0237] The synthesis of intermediate 21-4 followed the method described for intermediate 12-2 above. The yield of intermediate 21-4 was 81%, and the mass spectrometry results of the product were [m / z [H]]. + =307.

[0238] The synthesis of intermediate 21-3 followed the method described for intermediate 1-3 above. The yield of intermediate 21-3 was 86%, and the mass spectrometry results of the product were [m / z [H]]. + =542.

[0239] The synthesis of compound M21 followed the same method as that used for compound M1. The yield of compound M21 was 81%, and the mass spectrometry results of the product were [m / z [H]]. + =789, elemental analysis results: C, 90.80; H, 5.32; N, 1.81; O, 2.07.

[0240] Example 22

[0241] The synthetic route for compound M22 is as follows:

[0242]

[0243] The synthesis of intermediate 22-3 followed the same method as that used for intermediates 1-3 described above. The yield of intermediate 22-3 was 84%, and the mass spectrometry results of the product were [m / z]. + =461.

[0244] The synthesis of compound M22 followed the method described for compound M1 above. The yield of compound M22 was 82%, and the mass spectrometry results of the product were [m / z [H]]. + =551, elemental analysis results: C, 90.95; H, 6.52; N, 2.54.

[0245] Example 23

[0246] The synthetic route for compound M23 is as follows:

[0247]

[0248] The synthesis of intermediate 23-3 followed the same method as that used for intermediate 1-3 described above. The yield of intermediate 23-3 was 85%, and the mass spectrometry results of the product were [m / z]. + =461.

[0249] The synthesis of compound M23 followed the same method as that used for compound M1. The yield of compound M23 was 88%, and the mass spectrometry results of the product were [m / z [H]]. + =564, elemental analysis results: C, 91.90; H, 5.62; N, 2.41.

[0250] Example 24

[0251] The synthetic route for compound M24 is as follows:

[0252]

[0253] The synthesis of intermediate 24-3 followed the same method as that used for intermediate 1-3 described above. The yield of intermediate 24-3 was 84%, and the mass spectrometry results of the product were [m / z]. + =461.

[0254] The synthesis of compound M24 followed the method described for compound M1 above. The yield of compound M24 was 86%, and the mass spectrometry results of the product were [m / z [H]]. + = 622, elemental analysis results: C, 91.91; H, 5.71; N, 2.34.

[0255] Example 25

[0256] The synthetic route for compound M25 is as follows:

[0257]

[0258] The synthesis of intermediate 25-3 followed the same method as that used for intermediates 1-3 described above. The yield of intermediate 25-3 was 83%, and the mass spectrometry results of the product were [m / z]. + =461.

[0259] The synthesis of compound M25 followed the same method as that used for compound M1. The yield of compound M25 was 86%, and the mass spectrometry results of the product were [m / z [H]]. + = 674, elemental analysis results: C, 92.23; H, 5.60; N, 2.13.

[0260] Example 26

[0261] The synthetic route for compound M26 is as follows:

[0262]

[0263] The synthesis of intermediate 26-3 followed the method described for intermediates 1-3 above. The yield of intermediate 26-3 was 87%, and the mass spectrometry results of the product were [m / z [H]]. + =468.

[0264] The synthesis of compound M26 followed the method described for compound M1 above. The yield of compound M26 was 84%, and the mass spectrometry results of the product were [m / z [H]]. + = 670, elemental analysis results: C, 92.23; H, 5.60; N, 2.13.

[0265] Example 27

[0266] The synthetic route for compound M27 is as follows:

[0267]

[0268] The synthesis of intermediate 27-3 followed the same method as that used for intermediates 1-3 described above. The yield of intermediate 27-3 was 85%, and the mass spectrometry results of the product were [m / z [H]]. + =468.

[0269] The synthesis of compound M27 followed the method described for compound M1 above. The yield of compound M27 was 80%, and the mass spectrometry results of the product were [m / z [H]]. + =746, elemental analysis results: C, 92.52; H, 5.59; N, 1.89.

[0270] Example 28

[0271] The synthetic route for compound M28 is as follows:

[0272]

[0273] The synthesis of intermediate 28-3 followed the same method as that used for intermediates 1-3 described above. The yield of intermediate 28-3 was 84%, and the mass spectrometry results of the product were [m / z]. + =468.

[0274] The synthesis of compound M28 followed the method described for compound M1 above. The yield of compound M28 was 82%, and the mass spectrometry results of the product were [m / z [H]]. + = 644, elemental analysis results: C, 92.24; H, 5.51; N, 2.24.

[0275] Example 29

[0276] The synthetic route for compound M29 is as follows:

[0277]

[0278] The synthesis of intermediate 29-3 followed the same method as that used for intermediates 1-3 described above. The yield of intermediate 29-3 was 82%, and the mass spectrometry results of the product were [m / z]. + =468.

[0279] The synthesis of compound M29 followed the method described for compound M1 above. The yield of compound M29 was 85%, and the mass spectrometry results of the product were [m / z [H]]. + =722, elemental analysis results: C, 92.23; H, 5.72; N, 1.99.

[0280] Example 30

[0281] The synthetic route for compound M30 is as follows:

[0282]

[0283] The synthesis of intermediate 30-3 followed the method described for intermediates 1-3 above. The yield of intermediate 30-3 was 83%, and the mass spectrometry results of the product were [m / z]. + =468.

[0284] The synthesis of compound M30 followed the same method as that used for compound M1 described above. The yield of compound M30 was 82%, and the mass spectrometry results of the product were [m / z [H]]. + =784, elemental analysis results: C, 92.60; H, 5.54; N, 1.85.

[0285] Example 31

[0286] The synthetic route for compound M31 is as follows:

[0287]

[0288] The synthesis of intermediate 31-3 followed the same method as that used for intermediate 1-3 described above. The yield of intermediate 31-3 was 84%, and the mass spectrometry results of the product were [m / z]. + =468.

[0289] The synthesis of compound M31 followed the method described above for the synthesis of compound M1. The yield of compound M31 was 80%, and the mass spectrometry results of the product were [m / z [H]]. + = 782. Elemental analysis results: C, 92.83; H, 5.31; N, 1.84.

[0290] Example 32

[0291] The synthetic route for compound M32 is as follows:

[0292]

[0293] The synthesis of intermediate 32-3 followed the same method as that used for intermediates 1-3 described above. The yield of intermediate 32-3 was 84%, and the mass spectrometry results of the product were [m / z]. + =468.

[0294] The synthesis of compound M32 followed the same method as that used for compound M1 described above. The yield of compound M32 was 80%, and the mass spectrometry results of the product were [m / z [H]]. + =722, elemental analysis results: C, 92.22; H, 5.73; N, 1.95.

[0295] Example 33

[0296] The synthetic route for compound M33 is as follows:

[0297]

[0298] The synthesis of intermediate 33-3 followed the method described for intermediates 1-3 above. The yield of intermediate 33-3 was 83%, and the mass spectrometry results of the product were [m / z]. + =468.

[0299] The synthesis of compound M33 followed the same method as that used for compound M1 described above. The yield of compound M33 was 81%, and the mass spectrometry results of the product were [m / z [H]]. + =709, elemental analysis results: C, 90.52; H, 5.41; N, 3.95.

[0300] Example 34

[0301] The synthetic route for compound M34 is as follows:

[0302]

[0303] The synthesis of intermediate 34-3 followed the same method as that used for intermediates 1-3 described above. The yield of intermediate 34-3 was 86%, and the mass spectrometry results of the product were [m / z [H]]. + =468.

[0304] The synthesis of compound M34 followed the method described for compound M1 above. The yield of compound M34 was 82%, and the mass spectrometry results of the product were [m / z [H]]. + =709, elemental analysis results: C, 90.52; H, 5.43; N, 3.96.

[0305] Example 35

[0306] The synthetic route for compound M35 is as follows:

[0307]

[0308] The synthesis of intermediate 35-3 followed the same method as that used for intermediates 1-3 described above. The yield of intermediate 35-3 was 82%, and the mass spectrometry results of the product were [m / z]. + =468.

[0309] The synthesis of compound M35 followed the same method as that used for compound M1 described above. The yield of compound M35 was 80%, and the mass spectrometry results of the product were [m / z [H]]. + =714, elemental analysis results: C, 90.32; H, 5.22; N, 2.03; O, 2.38.

[0310] Example 36

[0311] The synthetic route for compound M36 is as follows:

[0312]

[0313] The synthesis of intermediate 36-3 followed the method described for intermediates 1-3 above. The yield of intermediate 36-3 was 83%, and the mass spectrometry results of the product were [m / z]. + =468.

[0314] The synthesis of compound M36 followed the method described for compound M1 above. The yield of compound M36 was 82%, and the mass spectrometry results of the product were [m / z [H]]. + =687, elemental analysis results: C, 90.24; H, 5.12; N, 2.13; O, 2.42.

[0315] It is understandable that the compounds M1 to M36 prepared in Examples 1 to 36 above all belong to the organic compounds shown in formula (1).

[0316] Comparative Example

[0317] This application provides three comparative compounds, denoted as Ref-01, Ref-02, and Ref-03, respectively, through Comparative Example 1, Comparative Example 2, and Comparative Example 3, with the following chemical structural formulas:

[0318]

[0319] (II) Energy Levels of Organic Compounds

[0320] In the embodiments of this application, the energy levels of the organic compound materials play a crucial role. The highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energy levels of the organic compounds M1–M36 provided in the embodiments of this application and the comparative compounds Ref-01–Ref-03 provided in the comparative examples can be obtained through theoretical calculations. Specifically, the energy levels of the organic compound materials can be obtained through quantum calculations, such as using TD-DFT (time-dependent density functional theory) with Gaussian09W (Gaussian Inc.). Specific simulation methods can be found in WO2011141110. In the description of the embodiments of this application, the ground state (S0) configuration is calculated according to density functional theory (DFT) under the B3LYP / 6-31G(d) or B3LYP / 6-31G(d,p) basis sets. The HOMO and LUMO values ​​of the organic compound material were calculated using time-dependent density functional theory (TD-DFT) on the B3LYP / 6-31G(d) or B3LYP / 6-31G(d,p) basis sets based on the optimized S0 structure. The HOMO and LUMO energy levels were calculated according to the calibration formulas below; S1, T1, and the resonance factor f(S1) were used directly.

[0321] HOMO(eV)=((HOMO(G)×27.212)-0.9899) / 1.1206;

[0322] LUMO(eV)=((LUMO(G)×27.212)-2.0041) / 1.385;

[0323] Among them, HOMO(G) and LUMO(G) are the direct calculation results of Gaussian 09W, with units of Hartree, while HOMO(eV) and LUMO(eV) are the results after conversion.

[0324] The HOMO (eV) and E of organic compounds M1 to M36 provided in the embodiments of this application and comparative compounds Ref-01 to Ref-03 provided in the comparative examples are shown. T1 The (eV) results are shown in Table 1.

[0325] Table 1

[0326]

[0327] As shown in Table 1, the HOMO energy levels and E of compounds M1 to M36 provided in the embodiments of this application are... T1 Energy levels compared with the HOMO levels and E of compounds Ref-01 to Ref-03 T1 The comparable energy levels indicate that these compounds are all suitable as luminescent auxiliary materials. Using these compounds to fabricate luminescent auxiliary layers in organic electronic devices can optimize hole transport, reduce the energy level barrier between the hole transport layer and the luminescent layer, effectively prevent electron backpropagation, and ensure that excitons are successfully formed in the luminescent layer and emit light.

[0328] (III) Fabrication and Characterization of OLED Devices

[0329] 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:

[0330]

[0331] 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: ITO / PD:HT (3:97, 10nm) / HT (130nm) / compound M1 (90nm) provided in this application embodiment / Host:Dopant (3%, 40nm) / ET:Liq (5:5, 30nm) / Liq (1nm) / Al (100nm). This application takes the fabrication method of OLED device using compound M1 as the light-emitting auxiliary material as an example, and the fabricated OLED device is denoted as "OLED-1 device". The fabrication method of OLED-1 device includes the following steps a to c.

[0332] a. Cleaning of ITO conductive glass: Clean with chloroform, ketone, and isopropanol, followed by ultraviolet ozone plasma treatment.

[0333] b. Preparation of organic functional layer: First, the ITO conductive glass was transferred into a vacuum vapor deposition apparatus and deposited under high vacuum (1×10⁻⁶). -6 At millibars, resistance heating is used for evaporation. Hole injection materials PD and HT were deposited on ITO conductive glass at a deposition rate of 3:97, resulting in a hole injection layer with a thickness of 10 nm; then, using... The hole transport material HT was deposited on the hole injection layer at a certain evaporation rate to obtain a hole transport layer with a thickness of 130 nm; then, at... The compound M1 provided in the above embodiments was deposited on the hole transport layer at a deposition rate of [percentage missing] to obtain a light-emitting auxiliary layer with a thickness of 90 nm; then, [percentage missing] The Host and Dopant were deposited on the luminescent auxiliary layer at a deposition rate of 97:3, resulting in a luminescent layer with a thickness of 40 nm. Subsequently, electron transport materials ET and Liq were placed in different evaporation crucibles in a vacuum chamber and subjected to high vacuum (1×10⁻⁶) conditions. -6 Under millibar (mbar) conditions, ET and Liq were co-deposited at a weight ratio of 5:5 to form an electron transport layer with a thickness of 30 nm on the luminescent layer; then, with Electron injection material Liq was deposited on the electron transport layer at a evaporation rate of [value missing], resulting in an electron injection layer with a thickness of 1 nm; then, [details missing]. 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.

[0334] c. Encapsulation: The device obtained in step c is encapsulated in a nitrogen glove box using ultraviolet-cured resin to finally obtain the OLED-1 device.

[0335] Referring to the fabrication method of OLED-1 device, compounds M2 to M36 synthesized in the examples were selected as light-emitting auxiliary materials for OLED devices, and OLED-2 to OLED-36 devices were fabricated accordingly. It can be understood that, in the above fabrication methods of OLED-1 to OLED-36 devices, all experimental conditions are the same except for the light-emitting auxiliary materials.

[0336] Furthermore, referring to the fabrication method of the device examples, comparative compounds Ref-01 to Ref-03 were used as luminescent auxiliary materials to prepare comparative OLED-Ref-01 to OLED-Ref-03 devices. Compared with the fabrication method of OLED-1 device, the fabrication methods of OLED-Ref-01 to OLED-Ref-03 devices are identical except for the luminescent auxiliary materials.

[0337] In this embodiment, the current-voltage (JV) characteristics of OLED-1 to OLED-36 and OLED-Ref-01 to OLED-Ref-03 devices were characterized, and important parameters such as luminous efficiency and lifetime were recorded. The results are shown in Table 2. Luminous efficiency is defined as a current density of 10 mA·cm⁻¹. -2 The relative value obtained at that time. The device's lifetime (LT95) is at a constant 50 mA·cm. -2 The time it takes for the brightness to drop to 95% of the initial brightness @1000 nits under current.

[0338] Table 2

[0339]

[0340]

[0341]

[0342] As shown in Table 2, when compounds M1 to M36 provided in Examples 1 to 36 of this application are used as red light emitting auxiliary materials, the OLED-1 to OLED-36 devices prepared therefrom are significantly better than the OLED-Ref-01 to OLED-Ref-3 devices provided in the comparative examples in terms of luminous efficiency and lifetime. At the same time, compared with OLED-Ref-01 to OLED-Ref-3 devices, the OLED-1 to OLED-36 devices provided in the examples of this application have lower driving voltages and exhibit better overall performance.

[0343] Therefore, it is evident that the red light emitting auxiliary material of this application is significantly superior in performance to the similar materials in the comparative examples. This fully demonstrates that the OLED devices prepared using the organic compound shown in formula (1) of this application as the red light emitting auxiliary material not only have significantly improved luminous efficiency and significantly extended lifespan, but also maintain a low driving voltage, exhibiting excellent comprehensive performance.

[0344] In summary, in the embodiments of this application, the organic compound represented by formula (1) is a deuterated triarylamine compound containing a bis-naphthalene structure and a dibenzo-p-5-membered ring structure. This organic compound has significant advantages as a hole transport material in organic electronic devices. The introduction of the bis-naphthalene structure enhances the conjugation effect and steric hindrance of the organic compound molecule, enabling it to maintain a stable film morphology at high temperatures during film formation and suppressing crystallization, thus improving film stability. Furthermore, the combination of the nitrogen atom in the triarylamine framework with the electron acceptor properties of the bis-naphthalene structure optimizes the HOMO and T1 energy levels of the organic compound material, facilitating hole injection and transport, balancing carrier transport and exciton confinement, thereby improving device luminescence efficiency. The introduction of deuterium atoms helps suppress molecular vibrational frequencies, reduce intramolecular energy dissipation, and lower the energy required for electron transitions, thus helping to reduce the driving voltage required for device operation. Simultaneously, the high bond energy of deuterium atoms makes the organic compound molecule containing deuterium atoms more stable, thereby increasing the device's lifespan. Therefore, when the organic compounds provided in this application are used in organic electronic devices as red light emitting auxiliary materials, the driving voltage of the devices can be significantly reduced, while the luminous efficiency and lifespan of the devices can be effectively improved.

[0345] The above provides a detailed description of an organic compound, mixture, composition, organic electronic device, and display panel 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 organic compound, characterized in that, The general structural formula of the organic compound is shown in formula (1): Where X is selected from oxygen atom, sulfur atom or C-(CH3)2; R is selected from hydrogen atom, phenyl or naphthyl; L1 is selected from at least one of a single bond, 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; Ar is selected from at least one of 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; The heteroatom in the heteroaromatic group is selected from one or more of nitrogen, oxygen, or sulfur atoms; the substituted or unsubstituted substituent group is selected from methyl, deuterated methyl, tert-butyl, adamantane, phenyl, biphenyl, naphthyl, fluorenyl, dibenzofuranyl, or dibenzothiopheneyl. In the structure shown in formula (1), at least one hydrogen atom in the groups other than X is not substituted or is substituted by a deuterium atom.

2. The organic compound according to claim 1, characterized in that, L1 is selected from single bond, phenyl, biphenyl, naphthyl, fluorenyl, dibenzofuranyl, dibenzothiophenyl, or carbazoyl, and at least one hydrogen atom in L1 is not substituted or is substituted by a deuterium atom.

3. The organic compound according to claim 1 or 2, characterized in that, Ar is selected from any of the following groups: In this context, "*" represents a connection site; at least one hydrogen atom in Ar is not substituted or is substituted by a deuterium atom.

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

5. A mixture, characterized in that, The mixture comprises at least one organic compound as described in any one of claims 1 to 4 and at least one organic functional material, wherein the organic functional material is selected from at least one of hole injection materials, hole transport materials, light-emitting auxiliary materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, organic light-emitting guest materials, and organic host materials.

6. A composition, characterized in that, The composition comprises at least one organic solvent and at least one organic compound as described in any one of claims 1 to 4, or the composition comprises at least one organic solvent and a mixture as described in claim 5.

7. An organic electronic device, characterized in that, The organic electronic device includes: First electrode; An organic functional layer is disposed on one side of the first electrode; The second electrode is disposed on the side of the organic functional layer away from the first electrode; The organic functional layer is made of at least one organic compound as described in any one of claims 1 to 4 or a mixture as described in claim 5, or the organic functional layer is prepared from the composition as described in claim 6.

8. The organic electronic device according to claim 7, characterized in that, The organic functional layer includes a light-emitting auxiliary layer and an organic light-emitting layer stacked together, wherein the material of the light-emitting auxiliary layer includes at least one of the organic compounds.

9. The organic electronic device according to claim 8, characterized in that, The light emitted by the organic light-emitting layer is red light.

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

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