Organic compounds, mixtures, compositions, organic electronic devices and display panels

Abstract

The application discloses an organic compound, a mixture, a composition, an organic electronic device and a display panel, and a structural formula of the organic compound is shown in formula (1). The organic compound provided by the application can be applied to an organic electronic device as a hole transport material or a light-emitting auxiliary material, is beneficial to improving a hole transport rate, balances hole and electron transport, and thus improves light-emitting efficiency and a service life of the organic electronic device.

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 electroluminescence (OEC) refers to the phenomenon of converting electrical energy into light energy using organic materials. OEC devices typically have an anode and a cathode, as well as an organic layer disposed between them. To improve the efficiency and lifespan of OEC devices, the organic layer has a multi-layered structure, with each layer containing different organic materials. Specifically, the organic layer may include a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. In such OEC devices, applying a voltage between the two electrodes injects holes into the organic layer from the anode and electrons into the organic layer from the cathode. When the injected holes and electrons meet, excitons are formed, and these excitons emit light when they transition back to the ground state. Such OEC devices possess characteristics such as self-illumination, high brightness, high efficiency, low driving voltage, wide viewing angle, high contrast, and high responsiveness. For example, organic light-emitting diodes (OLEDs) have advantages such as wide viewing angle, fast response time, low operating voltage, and thin panel thickness in optoelectronic devices (e.g., flat panel displays and lighting), and therefore have broad development potential.

[0003] To obtain highly efficient organic electroluminescent devices, in addition to developing high-performance luminescent materials, the development of carrier transport materials is also crucial. Currently, most carrier transport materials are small-molecule materials based on carbazole derivatives. These materials still suffer from an imbalance in hole and electron transport, resulting in devices using these materials exhibiting low luminous efficiency and short lifetime. Therefore, solutions for carrier transport materials still require improvement and development. Summary of the Invention

[0004] This application provides an organic compound, mixture, composition, organic electronic device, and display panel. The organic compound can be used as a hole transport material or light-emitting auxiliary material in organic electronic devices, which is beneficial to improve the hole transport rate, balance hole and electron transport, and thus improve the luminous efficiency and lifespan of organic electronic devices.

[0005] To achieve the above objectives, according to a first aspect of this application, an organic compound is provided, the structural formula of which is shown in formula (1): (1); Ar1, Ar2 and Ar3 are each independently selected from at least one of substituted or unsubstituted aromatic groups having 6-30 carbon atoms, or substituted or unsubstituted heteroaromatic groups having 5-30 carbon atoms. Z is selected from O, S, NR1 or CR2R3; R1, R2 and R3 are each independently selected from at least one of hydrogen atom, deuterium atom, straight-chain alkyl group having 1 to 20 carbon atoms, branched alkyl group having 3 to 20 carbon atoms, cyclic alkyl group having 3 to 20 carbon atoms, substituted or unsubstituted aromatic group having 5 to 60 ring atoms, and substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms.

[0006] According to a second aspect of this application, a mixture is also provided, the mixture comprising at least one organic functional material and at least one or more of the organic compounds described above, wherein the organic functional material is selected from at least one of hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, organic light-emitting guest materials, and organic host materials.

[0007] According to a third aspect of this application, a composition is also 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 of the organic solvents described above and a mixture thereof.

[0008] According to a fourth aspect of this application, an organic electronic device is also provided, the organic electronic device comprising: 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 of the organic compounds described above, or the organic functional layer is made of a mixture described above, or the organic functional layer is prepared from the composition described above.

[0009] According to a fifth aspect of this application, a display panel is also provided, the display panel comprising the organic electronic devices described above.

[0010] 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 triarylamine compound, and the dibenzofuran group and carbazole group in the triarylamine compound are connected through a benzene ring, fused with the five-membered ring conjugated group, thereby effectively improving the molecular packing, making the molecule of the triarylamine compound more rigid, and thus increasing the glass transition temperature of the triarylamine compound. When organic electronic devices are prepared using the triarylamine compound, the lifespan of the device can be extended and the luminous efficiency of the device can be improved. In addition, the organic compound represented by formula (1) provided in this application can be used as a hole transport material or a light-emitting auxiliary material. By cooperating with a suitable light-emitting material, the luminous efficiency and lifespan of the organic electronic device can be improved. In addition, the organic compound represented by formula (1) provided in this application has a low manufacturing cost, which is beneficial to reducing the manufacturing cost of organic electronic devices. Therefore, this application provides a solution for organic electronic devices with low manufacturing cost, high luminous efficiency, and long lifespan. Attached Figure Description

[0011] To gain a more complete understanding of this application and its beneficial effects, the following description will be provided in conjunction with the accompanying drawings, wherein the same reference numerals in the following description denote the same parts.

[0012] Figure 1 This is a schematic diagram of the structure of an organic electronic device provided in an embodiment of this application; Figure 2 This is another structural schematic diagram of the organic electronic device provided in the embodiments of this application; Figure 3 This is the 1H NMR spectrum of compound C16 provided in the embodiments of this application.

[0013] Explanation of reference numerals in the attached figures: 100, organic electronic device; 10, substrate; 20, first electrode (anode); 30, organic functional layer; 40, hole injection layer; 50, hole transport layer; 50a, first hole transport layer; 50b, second hole transport layer; 60, light-emitting layer; 70, electron transport layer; 80, electron injection layer; 90, second electrode (cathode). Detailed Implementation

[0014] The technical solutions in the embodiments of this application will be clearly and completely described below with reference to specific examples. Unless otherwise defined, all technical and scientific terms used in this application have the same meaning as commonly understood by those skilled in the art. The term "and / or" as used in this application includes any and all combinations of one or more of the associated listed items.

[0015] In this application, "substitution" means that the hydrogen atom in the substituent is replaced by the substituent.

[0016] In this application, when the same substituent appears multiple times, it can be independently selected from different groups. If the general formula contains multiple R1s, then R1s can be independently selected from different groups.

[0017] 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.

[0018] In this application, "ring atom number" refers to the number of atoms in the ring itself of a structural compound obtained by atomic bonding to form a ring (e.g., monocyclic compound, fused ring compound, cross-linked compound, carbocyclic compound, heterocyclic compound). When the ring is substituted by a substituent, the atoms contained in the substituent are not included in the ring-forming atoms. The same applies to the "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.

[0019] In this application, "alkyl" can mean straight-chain, branched, and / or cyclic alkyl. The number of carbon atoms in an alkyl group can be 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. 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.

[0020] In this application, "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 rings, at least one is an aromatic ring system. For example, "substituted or unsubstituted aryl having 6 to 40 ring atoms" refers to an aryl containing 6 to 40 ring atoms, preferably a substituted or unsubstituted aryl having 6 to 30 ring atoms, more preferably a substituted or unsubstituted aryl having 6 to 18 ring atoms, and particularly preferably a substituted or unsubstituted aryl having 6 to 14 ring atoms, and optionally further substituted on the aryl group; 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, triarylamine, and diaryl ether systems should also be included in the definition of aryl.

[0021] In this application, "heteroaryl or heteroaromatic group" refers to an aryl group in which at least one carbon atom is replaced by a non-carbon atom, which can be an N atom, an O atom, an S atom, etc. For example, "substituted or unsubstituted heteroaryl group having 5 to 40 ring atoms" refers to a heteroaryl group having 5 to 40 ring atoms, preferably a substituted or unsubstituted heteroaryl group having 6 to 30 ring atoms, more preferably a substituted or unsubstituted heteroaryl group having 6 to 18 ring atoms, particularly preferably a substituted or unsubstituted heteroaryl group having 6 to 14 ring atoms, and the heteroaryl group may optionally be further substituted. Suitable examples include, but are not limited to, those that are not substituted. Triazine, pyridine, pyrimidine, imidazole, furan, thiophene, benzofuran, benzothiophene, indole, carbazole, pyrroloimidazole, pyrrolopyrrolo, thiophenolopyrrolo, thiophenolothiophene, furanolopyrrolo, furanolofuran, thiophenolofuran, benzoisoxazole, benzoisothiazazole, quinoline, isoquinoline, o-diazonine, quinoxaline, phenanthridine, primidine, quinazoline, quinazolinone, dibenzothiophene, dibenzofuran, carbazole and their derivatives.

[0022] In this application, "amino group" refers to an amine derivative having the structural feature of the formula -N(X)2, wherein each "X" is independently H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, etc. Non-limiting types of amino groups include -NH2, -N(alkyl)2, -NH(alkyl), -N(cycloalkyl)2, -NH(cycloalkyl), -N(heterocyclic)2, -NH(heterocyclic), -N(aryl)2, -NH(aryl), -N(alkyl)(aryl), -N(alkyl)(heterocyclic), -N(cycloalkyl)(heterocyclic), -N(aryl)(heteroaryl), -N(alkyl)(heteroaryl), etc.

[0023] In this application, the "linked to single key" "" indicates a connection or fusion site.

[0024] 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.

[0025] In this application, when no fusion site is specified in the group, it means that any fusionable site in the group is selected as the fusion site, preferably two or more sites in the adjacent position of the group are fusion sites.

[0026] 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.

[0027] In this application, "adjacent groups" means that there are no substituted sites between two substituents.

[0028] This application provides an aromatic amine organic compound, the structural formula of which is shown in formula (1): (1); Ar1, Ar2 and Ar3 are each independently selected from at least one of substituted or unsubstituted aromatic groups having 6-30 carbon atoms, or substituted or unsubstituted heteroaromatic groups having 5-30 carbon atoms. Z is selected from O, S, NR1 or CR2R3; R1, R2 and R3 are each independently selected from at least one of hydrogen atom, deuterium atom, straight-chain alkyl group having 1 to 20 carbon atoms, branched alkyl group having 3 to 20 carbon atoms, cyclic alkyl group having 3 to 20 carbon atoms, substituted or unsubstituted aromatic group having 5 to 60 ring atoms, and substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms.

[0029] In some embodiments, any of the substituted or unsubstituted substituents in Ar1, Ar2, Ar3, R1, R2, and R3 are selected from deuterium, methyl, tert-butyl, adamantyl, phenyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, fluorenyl, or carbazoyl.

[0030] In some embodiments, the organic compound is selected from the structures shown in formula (1-1) or formula (1-2): (1-1) (1-2).

[0031] Understandably, the range of choices for Ar2 and Ar3 in the structures shown in equations (1-1) and (1-2) is the same as shown above.

[0032] In some embodiments, Z is selected from O, NR1, or CR2R3.

[0033] In some embodiments, Ar2 and Ar3 are each independently selected from any of the following groups, either substituted or unsubstituted:

[0034]

[0035]

[0036]

[0037] ; in, Indicates the connection site.

[0038] It should be noted that the groups listed above can be substituted or not substituted. The substituted groups are selected from deuterium, methyl, tert-butyl, adamantyl, phenyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothiophene, fluorenyl or carbazoyl.

[0039] In some embodiments, the organic compound is selected from any one of the following compounds:

[0040]

[0041]

[0042]

[0043]

[0044]

[0045]

[0046]

[0047]

[0048]

[0049]

[0050]

[0051]

[0052]

[0053] .

[0054] It is understood that the organic compounds represented by formula (1) provided in the embodiments of this application are not limited to those listed above.

[0055] In some embodiments, the organic compound represented by formula (1) provided in this application can be used as an organic functional material in organic electronic devices, particularly in OLED devices. Organic functional materials can be categorized into hole injection materials (HIM), hole transport materials (HTM), electron transport materials (ETM), electron injection materials (EIM), electron blocking materials (EBM), hole blocking materials (HBM), light-emitting dopant materials, and host materials. Host materials can be categorized into phosphorescent host materials, fluorescent host materials, and host materials for thermally activated delayed fluorescence (TADF) luminescent materials. The organic compound represented by formula (1) provided in this application can be any one of the organic functional materials listed above.

[0056] In a preferred embodiment, the organic compound represented by formula (1) provided in this application is a hole transport material or a light-emitting auxiliary material.

[0057] In some embodiments, the glass transition temperature (Tg) of the organic compound represented by formula (1) provided in this application is greater than or equal to 100°C. In a preferred embodiment, Tg is greater than or equal to 120°C. In a more preferred embodiment, Tg is greater than or equal to 140°C. In a more preferred embodiment, Tg is greater than or equal to 160°C. In a most preferred embodiment, Tg is greater than or equal to 180°C.

[0058] This application also provides a mixture comprising at least one organic functional material and at least one organic compound represented by formula (1) above. The organic functional material is selected from at least one of hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, organic light-emitting guest materials, and organic host materials. For example, various organic functional materials are described in detail in WO2010135519A1, US20090134784A1, and WO2011110277A1, the entire contents of which are hereby incorporated herein by reference. The organic functional material can be a small molecule or a polymer material.

[0059] In some embodiments, the organic functional material in the mixture is selected from electron transport materials and is blended with the organic compound shown in formula (1) as a co-body for use in organic electronic devices.

[0060] In some embodiments, the organic compound represented by formula (1) is used in vapor-deposited OLED devices. Correspondingly, the molecular weight of the organic compound represented by formula (1) is less than or equal to 1100 g / mol, preferably less than or equal to 1000 g / mol, very preferably less than or equal to 950 g / mol, more preferably less than or equal to 900 g / mol, and most preferably less than or equal to 800 g / mol.

[0061] In some embodiments, the organic compound represented by formula (1) is used in a printed OLED device. Correspondingly, the organic compound represented by formula (1) has a molecular weight greater than or equal to 700 g / mol, preferably greater than or equal to 900 g / mol, more preferably greater than or equal to 1000 g / mol, and most preferably greater than or equal to 1100 g / mol.

[0062] This application also provides a composition comprising at least one organic solvent and at least one organic compound represented by formula (1) above, or the composition comprising at least one organic solvent and a mixture thereof.

[0063] 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.

[0064] 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.

[0065] 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 derivatives of these solvents, such as 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylphenylacetone, 3-methylphenylacetone, 2-methylphenylacetone, etc.

[0066] 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.

[0067] 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.

[0068] 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.

[0069] In some embodiments, the composition further includes 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.

[0070] In some embodiments, solvents particularly suitable for this application are those with Hansen solubility parameters in the following range: δd (dispersion force) of 17.0~23.2 MPa. 1 / 2 The range, especially in the 18.5~21.0 MPa range. 1 / 2 The range; δp (polar force) is 0.2~12.5MPa. 1 / 2 The range, especially 2.0~6.0 MPa 1 / 2 The range; δh (hydrogen bond force) is 0.9~14.2 MPa. 1 / 2 The range, especially in the range of 2.0~6.0 MPa 1 / 2 The range.

[0071] In some embodiments, the organic solvent in the composition is selected with its boiling point parameter in mind. In the embodiments of this application, the boiling point of the organic solvent is greater than or equal to 150°C; preferably, the boiling point of the organic solvent is greater than or equal to 180°C; more preferably, the boiling point of the organic solvent is greater than or equal to 200°C; more preferably, the boiling point of the organic solvent is greater than or equal to 250°C; most preferably, the boiling point of the organic solvent is 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.

[0072] In some embodiments, the composition provided in this application is a solution.

[0073] In other embodiments, the composition provided in this application is a suspension.

[0074] In some embodiments, the organic compound or the mixture in the composition has a mass fraction ranging from 0.01 wt% to 10 wt%. Preferably, the organic compound or the mixture in the composition has a mass fraction ranging from 0.1 wt% to 15 wt%. More preferably, the organic compound or the mixture in the composition has a mass fraction ranging from 0.2 wt% to 5 wt%. Most preferably, the organic compound or the mixture in the composition has a mass fraction ranging from 0.25 wt% to 3 wt%.

[0075] 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%.

[0076] 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.

[0077] 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.

[0078] The organic compounds, mixtures, or compositions provided in this application can be used in organic electronic devices. In the embodiments of this application, it is preferred to apply the organic compounds to the hole transport layer of an OLED device.

[0079] 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.

[0080] like Figure 1As shown, this application embodiment also provides an organic electronic device 100, which includes a substrate 10, a first electrode 20, an organic functional layer 30, and a second electrode 90. The first electrode 20 is disposed on one side of the substrate 10, the organic functional layer 30 is disposed on the side of the first electrode 20 away from the substrate 10, and the second electrode 90 is disposed on the side of the organic functional layer 30 away from the first electrode 20. The material of the organic functional layer 30 includes at least one organic compound of formula (1), or the material of the organic functional layer 30 includes a mixture of the above-described compounds, or the organic functional layer 30 is prepared from the above-described compositions.

[0081] In some embodiments, the organic functional layer 30 is selected from at least one of a hole injection layer (HIL), a hole transport layer (HTL), an emitting layer (EML), an electron blocking layer (EBL), an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0082] In some embodiments, the organic functional layer 30 includes a hole transport layer 50 and a light-emitting layer 60 stacked together; the material of the hole transport layer 50 includes at least one organic compound represented by formula (1) or a mixture thereof, or the hole transport layer 50 is prepared from the composition thereof.

[0083] In some embodiments, the organic functional layer 30 may further include a hole injection layer 40 disposed between the first electrode 20 and the hole transport layer 50, an electron transport layer 70 disposed between the light-emitting layer 60 and the second electrode 90, and an electron injection layer 80 disposed between the second electrode 90, but is not limited thereto.

[0084] In some embodiments, such as Figure 2 As shown, the hole transport layer 50 includes a first hole transport layer 50a and a second hole transport layer 50b stacked between the hole injection layer 40 and the light emission layer 60. The first hole transport layer 50a and the second hole transport layer 50b are made of different materials, and the material of the second hole transport layer 50b is selected from at least one organic compound represented by formula (1) or a mixture thereof, or the second hole transport layer 50b is prepared from the composition thereof.

[0085] In some embodiments, the material of the first hole transport layer 50a is selected from the compound shown in HT-1, but is not limited thereto.

[0086] In some embodiments, the first electrode 20 is the anode and the second electrode 70 is the cathode.

[0087] The anode may comprise a conductive metal, metal oxide, or conductive polymer. Holes can be readily injected into the hole injection layer (HIL), hole transport layer (HTL), or 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 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 the organic electronic devices described in this application.

[0088] 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 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 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 organic electronic 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.

[0089] In some embodiments, the luminescent material in the luminescent layer 60 is selected from singlet luminescent material, triplet luminescent material, or TADF material.

[0090] In some embodiments, the thickness of the organic functional layer 30 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.

[0091] In some embodiments, the organic electronic device 100 is selected from any one of 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). Particularly preferred is that the organic electronic device 100 is selected from any one of organic electroluminescent devices, such as OLEDs, OLEECs, and organic light-emitting field-effect transistors.

[0092] The organic light-emitting 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.

[0093] 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.

[0094] This application embodiment also provides a display panel, which includes the organic light-emitting device 100 described above.

[0095] 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.

[0096] The organic compounds and their preparation methods described in this application are further illustrated below with reference to specific embodiments, but this application is not limited to the following embodiments. Unless otherwise specified, the raw materials used in the following embodiments are commercially available products.

[0097] (I) Examples of Synthesis of Organic Compounds Example 1 The synthetic route for compound C-1 is shown below: .

[0098] Synthesis of intermediates 1-3: Intermediate 1-1 (10 mmol), intermediate 1-2 (10 mmol), Pd(dba)2 (0.1 mmol), (t-Bu)3P (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene. The reaction solution was heated to 100 °C and stirred for 6 h under a nitrogen atmosphere. After the reaction solution was cooled, the solvent was removed by rotary evaporation, and the product was extracted, washed with water, and separated. Organic phase column chromatography yielded intermediate 1-3 with a molar amount of 7.17 mmol, with a yield of 71.7%. The atmospheric pressure solid-state probe mass spectrometry result of the product was MS(ASAP) = 219.

[0099] Synthesis of intermediates 1-5: Intermediate 1-3 (10 mmol), intermediate 1-4 (10 mmol), Pd(dba)2 (0.1 mmol), (t-Bu)3P (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene. The reaction solution was heated to 100 °C and stirred for 6 h under a nitrogen atmosphere. After the reaction solution was cooled, the solvent was removed by rotary evaporation, and the mixture was extracted, washed with water, and separated. Organic phase column chromatography yielded intermediate 1-5 with a molar amount of 6.44 mmol, with a yield of 64.4%. The atmospheric pressure solid-state probe mass spectrometry result of the product was MS(ASAP) = 419.

[0100] Synthesis of intermediates 1-6: Intermediates 1-5 (10 mmol) and (Bpin)2 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (2 1 / 2 ml), and Pd(dppf)Cl2 (0.1 mmol) and potassium acetate (30 mmol) were added. The reaction solution was heated to 100 °C and stirred for 6 h under a nitrogen atmosphere. After the reaction solution cooled, most of the solvent was removed by rotary evaporation, followed by extraction, washing with water, separation, organic phase column chromatography, and recrystallization to obtain intermediate 1-6 with a molar amount of 6.24 mmol, with a yield of 62.4%. The atmospheric pressure solid-state probe mass spectrometry result of the product was MS(ASAP) = 511.

[0101] Synthesis of intermediates 1-8: Intermediates 1-6 (10 mmol) and 1-7 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (2 1 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The reaction solution was heated to 100 °C and stirred for 6 h under a nitrogen atmosphere. After the reaction solution cooled, most of the solvent was removed by rotary evaporation, followed by extraction, washing with water, separation, organic phase column chromatography, and recrystallization to obtain intermediate 1-8 with a molar amount of 8.63 mmol, with a yield of 86.3%. The atmospheric pressure solid-state probe mass spectrometry result of the product was MS(ASAP) = 479.

[0102] Synthesis of compound C-1: Intermediates 1-8 (10 mmol) and 1-9 (10 mmol) were dissolved in N,N In dimethylformamide (DMF), cesium carbonate (30 mmol) was added; the reaction solution was heated to 120 °C and stirred for 12 h under a nitrogen atmosphere; after the reaction solution was cooled, the solvent was removed by rotary evaporation, the extract was extracted and washed with water, and the organic phase column chromatography was used to obtain compound C-1 with a yield of 48.3%. The atmospheric pressure solid probe mass spectrometry result of the product was MS(ASAP) = 742.

[0103] Example 2 The synthetic route for compound C-2 is shown below: .

[0104] Synthesis of compound C-2: Intermediates 1-8 (10 mmol) and 2-1 (10 mmol) were dissolved in DMF, and cesium carbonate (30 mmol) was added. The reaction solution was heated to 120 °C and stirred for 12 h under a nitrogen atmosphere. After the reaction solution was cooled, the solvent was removed by rotary evaporation, and the product was extracted, washed with water, and separated. Organic phase column chromatography was used to obtain compound C-2 with a yield of 60.3%. The atmospheric pressure solid probe mass spectrometry result of the product was MS(ASAP) = 716.

[0105] Example 3 The synthetic route for compound C-3 is shown below: .

[0106] Synthesis of compound C-3: Intermediates 1-8 (10 mmol) and 3-1 (10 mmol) were dissolved in DMF, and cesium carbonate (30 mmol) was added. The reaction solution was heated to 120 °C and stirred for 12 h under a nitrogen atmosphere. After the reaction solution was cooled, the solvent was removed by rotary evaporation, and the product was extracted, washed with water, and separated. Organic phase column chromatography was used to obtain compound C-3 with a yield of 59.3%. The atmospheric pressure solid probe mass spectrometry result of the product was MS(ASAP) = 716.

[0107] Example 4 The synthetic route for compound C-4 is shown below: .

[0108] Synthesis of compound C-4: Intermediates 1-8 (10 mmol) and 4-1 (10 mmol) were dissolved in DMF, and cesium carbonate (30 mmol) was added. The reaction solution was heated to 120 °C and stirred for 12 h under a nitrogen atmosphere. After the reaction solution was cooled, the solvent was removed by rotary evaporation, and the product was extracted, washed with water, and separated. Organic phase column chromatography was used to obtain compound C-4 with a yield of 68.3%. The atmospheric pressure solid probe mass spectrometry result of the product was MS(ASAP) = 742.

[0109] Example 5 The synthetic route for compound C-5 is shown below: .

[0110] Synthesis of compound C-5: Intermediates 1-8 (10 mmol) and 5-1 (10 mmol) were dissolved in DMF, and cesium carbonate (30 mmol) was added. The reaction solution was heated to 120 °C and stirred for 12 h under a nitrogen atmosphere. After the reaction solution was cooled, the solvent was removed by rotary evaporation, and the product was extracted, washed with water, and separated. Organic phase column chromatography was used to obtain compound C-5 with a yield of 47.3%. The atmospheric pressure solid probe mass spectrometry result of the product was MS(ASAP) = 791.

[0111] Example 6 The synthetic route for compound C-6 is shown below: .

[0112] Synthesis of intermediate 6-3: Intermediate 6-1 (10 mmol), intermediate 6-2 (10 mmol), Pd(dba)2 (0.1 mmol), (t-Bu)3P (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene. The reaction solution was heated to 100 °C and stirred for 6 h under a nitrogen atmosphere. After the reaction solution was cooled, the solvent was removed by rotary evaporation, and the product was extracted, washed with water, and separated. Organic phase column chromatography yielded intermediate 6-3 with a molar amount of 7.17 mmol, with a yield of 74.7%. The atmospheric pressure solid-state probe mass spectrometry result of the product was MS(ASAP) = 225.

[0113] Synthesis of intermediate 6-5: Intermediate 6-3 (10 mmol), intermediate 6-4 (10 mmol), Pd(dba)2 (0.1 mmol), (t-Bu)3P (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene. The reaction solution was heated to 100 °C and stirred for 6 h under a nitrogen atmosphere. After the reaction solution was cooled, the solvent was removed by rotary evaporation, and the product was extracted, washed with water, and separated. Organic phase column chromatography yielded intermediate 6-5 with a molar amount of 7.34 mmol, with a yield of 73.4%. The atmospheric pressure solid-state probe mass spectrometry result of the product was MS(ASAP) = 425.

[0114] Synthesis of intermediate 6-6: Intermediate 6-5 (10 mmol) and (Bpin)2 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (2 1 / 2 ml), and Pd(dppf)Cl2 (0.1 mmol) and potassium acetate (30 mmol) were added. The reaction solution was heated to 100 °C and stirred for 6 h under a nitrogen atmosphere. After the reaction solution cooled, most of the solvent was removed by rotary evaporation, followed by extraction, washing with water, separation, organic phase column chromatography, and recrystallization to obtain intermediate 6-6 with a molar amount of 6.24 mmol, with a yield of 62.4%. The atmospheric pressure solid-state probe mass spectrometry result of the product was MS(ASAP) = 517.

[0115] Synthesis of intermediates 6-8: Intermediates 6-6 (10 mmol) and 6-7 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (2 1 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The reaction solution was heated to 100 °C and stirred for 6 h under a nitrogen atmosphere. After the reaction solution cooled, most of the solvent was removed by rotary evaporation, followed by extraction, washing with water, separation, organic phase column chromatography, and recrystallization to obtain intermediate 6-8 with a molar amount of 8.63 mmol, with a yield of 86.3%. The atmospheric pressure solid-state probe mass spectrometry result of the product was MS(ASAP) = 485.

[0116] Synthesis of compound C-6: Intermediates 6-8 (10 mmol) and 6-9 (10 mmol) were dissolved in DMF, and cesium carbonate (30 mmol) was added. The reaction solution was heated to 120 °C and stirred for 12 h under a nitrogen atmosphere. After the reaction solution was cooled, the solvent was removed by rotary evaporation, and the product was extracted, washed with water, and separated. Organic phase column chromatography was used to obtain compound C-6 with a yield of 47.3%. The atmospheric pressure solid probe mass spectrometry result of the product was MS(ASAP) = 722.

[0117] Example 7 The synthetic route for compound C-7 is shown below: .

[0118] Synthesis of compound C-7: Intermediates 6-8 (10 mmol) and 7-1 (10 mmol) were dissolved in DMF, and cesium carbonate (30 mmol) was added. The reaction solution was heated to 120 °C and stirred for 12 h under a nitrogen atmosphere. After the reaction solution was cooled, the solvent was removed by rotary evaporation, and the product was extracted, washed with water, and separated. Organic phase column chromatography was used to obtain compound C-7 with a yield of 44.3%. The atmospheric pressure solid probe mass spectrometry result of the product was MS(ASAP) = 738.

[0119] Example 8 The synthetic route for compound C-8 is shown below: .

[0120] Synthesis of compound C-8: Intermediates 6-8 (10 mmol) and 8-1 (10 mmol) were dissolved in DMF, and cesium carbonate (30 mmol) was added. The reaction solution was heated to 120 °C and stirred for 12 h under a nitrogen atmosphere. After the reaction solution was cooled, the solvent was removed by rotary evaporation, and the product was extracted, washed with water, and separated. Organic phase column chromatography was used to obtain compound C-7 with a yield of 67.3%. The atmospheric pressure solid probe mass spectrometry result of the product was MS(ASAP) = 748.

[0121] Example 9 The synthetic route for compound C-9 is shown below: .

[0122] Synthesis of compound C-9: Intermediates 6-8 (10 mmol) and 9-1 (10 mmol) were dissolved in DMF, and cesium carbonate (30 mmol) was added. The reaction solution was heated to 120 °C and stirred for 12 h under a nitrogen atmosphere. After the reaction solution was cooled, the solvent was removed by rotary evaporation, and the product was extracted, washed with water, and separated. Organic phase column chromatography was used to obtain compound C-9 with a yield of 53.3%. The atmospheric pressure solid probe mass spectrometry result of the product was MS(ASAP) = 722.

[0123] Example 10 The synthetic route for compound C-10 is shown below: .

[0124] Synthesis of compound C-10: Intermediate 6-8 (10 mmol) and intermediate 10-1 (10 mmol) were dissolved in DMF, and cesium carbonate (30 mmol) was added. The reaction solution was heated to 120 °C and stirred for 12 h under a nitrogen atmosphere. After the reaction solution was cooled, the solvent was removed by rotary evaporation, and the product was extracted, washed with water, and separated. Organic phase column chromatography was used to obtain compound C-10 with a yield of 62.3%. The atmospheric pressure solid probe mass spectrometry result of the product was MS(ASAP) = 748.

[0125] Example 11 The synthetic route for compound C-11 is shown below: .

[0126] Synthesis of compound C-11: Intermediate 6-8 (10 mmol) and compound 11-1 (10 mmol) were dissolved in DMF, and cesium carbonate (30 mmol) was added. The reaction solution was heated to 120 °C and stirred for 12 h under a nitrogen atmosphere. After the reaction solution was cooled, the solvent was removed by rotary evaporation, and the product was extracted, washed with water, and separated. Organic phase column chromatography was used to obtain compound C-11 with a yield of 61.3%. The atmospheric pressure solid probe mass spectrometry result of the product was MS(ASAP) = 738.

[0127] Example 12 The synthetic route for compound C-12 is shown below: .

[0128] Synthesis of compound C-12: Intermediates 6-8 (10 mmol) and 12-1 (10 mmol) were dissolved in DMF, and cesium carbonate (30 mmol) was added. The reaction solution was heated to 120 °C and stirred for 12 h under a nitrogen atmosphere. After the reaction solution was cooled, the solvent was removed by rotary evaporation, and the product was extracted, washed with water, and separated. Organic phase column chromatography was used to obtain compound C-12 with a yield of 61.3%. The atmospheric pressure solid probe mass spectrometry result of the product was MS(ASAP) = 722.

[0129] Example 13 The synthetic route for compound C-13 is shown below: .

[0130] Synthesis of compound C-13: Intermediates 6-8 (10 mmol) and 13-1 (10 mmol) were dissolved in DMF, and cesium carbonate (30 mmol) was added. The reaction solution was heated to 120 °C and stirred for 12 h under a nitrogen atmosphere. After the reaction solution was cooled, the solvent was removed by rotary evaporation, and the product was extracted, washed with water, and separated. Organic phase column chromatography was used to obtain compound C-13 in 63.3% yield. The atmospheric pressure solid probe mass spectrometry result of the product was MS(ASAP) = 748.

[0131] Example 14 The synthetic route for compound C-14 is shown below: .

[0132] Synthesis of intermediate 14-3: Intermediate 14-1 (10 mmol), intermediate 14-2 (10 mmol), Pd(dba)2 (0.1 mmol), (t-Bu)3P (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene. The reaction solution was heated to 100 °C and stirred for 6 h under a nitrogen atmosphere. After the reaction solution was cooled, the solvent was removed by rotary evaporation, and the product was extracted, washed with water, and separated. Organic phase column chromatography yielded intermediate 14-3 with a molar amount of 7.67 mmol, with a yield of 76.7%. The atmospheric pressure solid-state probe mass spectrometry result of the product was MS(ASAP) = 245.

[0133] Synthesis of intermediate 14-5: Intermediate 14-3 (10 mmol), intermediate 14-4 (10 mmol), Pd(dba)2 (0.1 mmol), (t-Bu)3P (0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene. The reaction solution was heated to 100 °C and stirred for 6 h under a nitrogen atmosphere. After the reaction solution was cooled, the solvent was removed by rotary evaporation, and the product was extracted, washed with water, and separated. Organic phase column chromatography yielded intermediate 14-5 with a molar amount of 7.34 mmol, with a yield of 73.4%. The atmospheric pressure solid probe mass spectrometry result of the product was MS(ASAP) = 445.

[0134] Synthesis of intermediate 14-6: Intermediate 14-5 (10 mmol) and (Bpin)2 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (2 1 / 2 ml), and Pd(dppf)Cl2 (0.1 mmol) and potassium acetate (30 mmol) were added. The reaction solution was heated to 100 °C and stirred for 6 h under a nitrogen atmosphere. After the reaction solution cooled, most of the solvent was removed by rotary evaporation, followed by extraction, washing with water, separation, organic phase column chromatography, and recrystallization to obtain intermediate 14-6 with a molar amount of 6.24 mmol, with a yield of 62.4%. The atmospheric pressure solid-state probe mass spectrometry result of the product was MS(ASAP) = 537.

[0135] Synthesis of intermediate 14-8: Intermediates 14-6 (10 mmol) and 14-7 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (2 1 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The reaction solution was heated to 100 °C and stirred for 6 h under a nitrogen atmosphere. After the reaction solution was cooled, most of the solvent was removed by rotary evaporation, followed by extraction, washing with water, separation, organic phase column chromatography, and recrystallization to obtain intermediate 14-8 with a molar amount of 8.63 mmol, with a yield of 86.3%. The atmospheric pressure solid-state probe mass spectrometry result of the product was MS(ASAP) = 505.

[0136] Synthesis of compound C-14: Intermediates 14-8 (10 mmol) and 14-9 (10 mmol) were dissolved in DMF, and cesium carbonate (30 mmol) was added. The reaction solution was heated to 120 °C and stirred for 12 h under a nitrogen atmosphere. After the reaction solution cooled, the solvent was removed by rotary evaporation, and the product was extracted, washed with water, and separated. Organic phase column chromatography was used to obtain compound C-14 in 56.3% yield. The atmospheric pressure solid probe mass spectrometry result of the product was MS(ASAP) = 742.

[0137] Example 15 The synthetic route for compound C-15 is shown below: .

[0138] Synthesis of compound C-15: Intermediate 14-8 (10 mmol) and intermediate 15-1 (10 mmol) were dissolved in DMF, and cesium carbonate (30 mmol) was added. The reaction solution was heated to 120 °C and stirred for 12 h under a nitrogen atmosphere. After the reaction solution was cooled, the solvent was removed by rotary evaporation, and the product was extracted, washed with water, and separated. Organic phase column chromatography was used to obtain compound C-15 with a yield of 56.3%. The atmospheric pressure solid probe mass spectrometry result of the product was MS(ASAP) = 780.

[0139] Example 16 The synthetic route for compound C-16 is shown below: .

[0140] Synthesis of compound C-16: Intermediates 14-8 (10 mmol) and 16-1 (10 mmol) were dissolved in DMF, and cesium carbonate (30 mmol) was added. Under a nitrogen atmosphere, the reaction mixture was heated to 120 °C and stirred for 12 h. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted, washed with water, and separated. Organic phase column chromatography yielded compound C-16 in 57.3%. The atmospheric pressure solid-state probe mass spectrometry (MS(ASAP)) result of the product was 754, and the proton NMR spectrum of the product is shown below. Figure 3 As shown, the product is compound C-16.

[0141] Comparative Example This application also provides five comparative compounds, denoted as Ref-1 to Ref-5, whose chemical structural formulas are shown below: .

[0142] (II) Calculation of energy levels of organic compounds The energy levels of organic compound materials can be obtained through quantum computing, such as using TD-DFT (Time-dependent Density Functional Theory) via Gaussian09W (Gaussian Inc.). For specific simulation methods, please refer to WO2011141110. First, the molecular geometry is optimized using the semi-empirical method "Ground State / Semi-empirical / Default Spin / AM1" (Charge 0 / Spin Singlet). Then, the energy structure of the organic molecule is calculated using TD-DFT (Time-dependent Density Functional Theory) to obtain "TD-SCF / DFT / Default Spin / B3PW91" and the basis set "6-31G(d)" (Charge 0 / Spin Singlet). HOMO and LUMO energy levels are calculated according to the following calibration formulas, with S1, T1, and the resonance factor f(S1) used directly.

[0143] HOMO(eV) = ((HOMO(G)×27.212)-0.9899) / 1.1206; LUMO(eV) = ((LUMO(G)×27.212)-2.0041) / 1.385; Wherein, HOMO(G) and LUMO(G) are direct calculation results from Gaussian 09W, and the units are Hartrees. Examples 1 to 16 of this application provide compounds C-1 to C-16, and comparative examples provide compounds Ref-1 to Ref-5, whose HOMO, LUMO, and T1 energy levels (E) are... T1 ) and S1 level (E S1 The calculation results are shown in Table 1.

[0144] Table 1

[0145] As shown in Table 1, the T1 energy levels (E) of compounds C-1 to C-16 provided in Examples 1 to 16 of this application are... T1 ) and S1 level (E S1 All of them are slightly higher than the T1 energy level (E) of compounds Ref-1 to Ref-5 provided in the comparative examples. T1 ) and S1 level (E S1 This demonstrates that the hole transport capabilities of compounds C-1 to C-16 provided in Examples 1 to 16 of this application are stronger than those of compounds Ref-1 to Ref-5 provided in the comparative examples.

[0146] (III) Fabrication and Characterization of OLED Devices The following detailed examples illustrate the fabrication process of OLED devices using compounds C-1 to C-16 and compounds Ref-1 to Ref-5. The structure of the OLED devices can be found in [reference needed]. Figure 2 The organic electronic device shown.

[0147] Specifically, the structure of the OLED device is: ITO / HIL (10nm) / HT-1 (60nm) / HT-2 (60nm) / Host:Dopant (3%, 25nm) / ET:Liq (30nm) / Liq (1nm) / Al (100nm).

[0148] The OLED device using compound C-1 as the hole transport material is denoted as OLED-1. The preparation steps of the OLED-1 device are as described in a to c.

[0149] a. Cleaning of conductive glass substrates (e.g., ITO substrates): Clean with chloroform, ketone, and isopropanol, followed by ultraviolet ozone plasma treatment.

[0150] b. Fabrication of the organic functional layer and cathode: The ITO substrate is transferred into a vacuum vapor deposition apparatus and deposited under high vacuum (1×10⁻⁶). -6At a temperature of 1000 mbar, resistance heating evaporation was used to deposit a 10 nm hole injection layer (HIL) using HATCN. Then, a 60 nm first hole transport layer (HT-1) and a 60 nm second hole transport layer (HT-2, material C-1) were sequentially deposited. Subsequently, Host and Dopant were co-deposited at a weight ratio of 97:3 to form a 25 nm light-emitting layer. Next, ET and LiQ were placed in different evaporation units and co-deposited at a weight ratio of 50% to form a 30 nm electron transport layer on the light-emitting layer. Then, a 1 nm layer of LiQ was deposited on the electron transport layer as an electron injection layer. Finally, a 100 nm thick Al cathode was deposited on the electron injection layer.

[0151] c. Encapsulation: The device is encapsulated in a nitrogen glove box using ultraviolet-cured resin to form an OLED-1 device.

[0152] The structures of the compounds involved in the fabrication of OLED devices are shown below: .

[0153] The fabrication process of other OLED devices is the same as that of OLED-1 devices, except that the material of the second hole transport layer is replaced with compounds C-2 to C-16 and compounds Ref-1 to Ref-5 in Table 2, respectively, and the resulting devices are OLED-2 to OLED-16 and OLED-Ref1 to OLED-Ref5, respectively.

[0154] The current-voltage (JV) characteristics of each OLED device were characterized using characterization equipment, and important parameters such as voltage, lifetime, and external quantum efficiency were recorded. The results are shown in Table 2. The lifetime LT95 is the time it takes for the brightness to decrease to 95% of the initial brightness @1000 nits under constant current. The LT95 and external quantum efficiency in Table 2 were calculated relative to the comparative device OLED-Ref1, i.e., using OLED-Ref1 with a lifetime of 1 and an external quantum efficiency of 100% as a reference.

[0155] Table 2

[0156] As shown in Table 2, using compounds C-1 to C-16 provided in this application as the second hole transport layer material (i.e., HT-2), the external quantum efficiency and lifetime of the obtained devices OLED-1 to OLED-16 are significantly higher than those of the comparative devices OLED-Ref1 to OLED-Ref5. Furthermore, the voltage of devices OLED-1 to OLED-16 is lower than that of devices OLED-Ref1 to OLED-Ref5.

[0157] Specifically, the reason why the external quantum efficiency and lifetime of devices OLED-1 to OLED-16 are significantly higher than those of devices OLED-Ref1 to OLED-Ref5 provided in the comparative example may be that in compounds C-1 to C-16, the carbazole group is fused with a five-membered ring conjugated group, which greatly changes the spatial structure of the molecule compared to the comparative example molecule, thereby improving the molecular packing, making the molecule more rigid, and increasing the glass transition temperature of the molecule, thus increasing the efficiency, stability and lifetime of the corresponding devices.

[0158] Specifically, compared with OLED-Ref5, the external quantum efficiency and lifetime of devices OLED-1 to OLED-16 are significantly improved. This may be because the introduction of five-membered ring conjugated groups for fusion can increase the efficiency, stability and lifetime of the device. This is because the introduction of benzene ring conjugated groups for fusion is not conducive to hole transport, which leads to a decrease in the efficiency, stability and lifetime of the device.

[0159] The hole transport material provided in the embodiments of this application is significantly better than the hole transport material provided in the comparative example. It can be seen that the OLED device prepared using the organic compound shown in formula (1) of this application has significantly improved luminous efficiency and lifetime.

[0160] It should be noted that the selection and design of hole transport materials or luminescent auxiliary materials play a crucial role in improving the luminous efficiency and extending the lifespan of OLED devices. Carefully designed hole transport materials or 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 exciton nonradiative recombination, thereby improving luminous efficiency and extending lifespan. Therefore, the embodiments of this application, by providing more efficient novel hole transport materials or luminescent auxiliary materials, can optimize the hole and electron transport balance within the device, which is beneficial for improving the device's luminous efficiency and lifespan, and also helps maintain a lower driving voltage.

[0161] 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 structural formula of the organic compound is shown in formula (1): (1)； Ar1, Ar2 and Ar3 are each independently selected from at least one of substituted or unsubstituted aromatic groups having 6-30 carbon atoms, or substituted or unsubstituted heteroaromatic groups having 5-30 carbon atoms. Z is selected from O, S, NR1 or CR2R3; R1, R2 and R3 are each independently selected from at least one of hydrogen atom, deuterium atom, straight-chain alkyl group having 1 to 20 carbon atoms, branched alkyl group having 3 to 20 carbon atoms, cyclic alkyl group having 3 to 20 carbon atoms, substituted or unsubstituted aromatic group having 5 to 60 ring atoms, and substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms.

2. The organic compound according to claim 1, characterized in that, The organic compound is selected from the structure shown in formula (1-1) or formula (1-2): (1-1) (1-2)。 3. The organic compound according to claim 1 or 2, characterized in that, Ar2 and Ar3 are each independently selected from any one of the following groups, either substituted or unsubstituted: ； in, Indicates the connection site.

4. The organic compound according to claim 1, characterized in that, The substituted or unsubstituted substituent group of any one of Ar1, Ar2, Ar3, R1, R2 and R3 is selected from deuterium, methyl, tert-butyl, adamantyl, phenyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothiophene, fluorenyl or carbazoyl.

5. The organic compound according to claim 1, characterized in that, The organic compound is selected from any one of the following compounds: 。 6. A mixture, characterized in that, The mixture includes at least one organic functional material and at least one organic compound as described in any one of claims 1 to 5, wherein the organic functional material is selected from at least one of hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, organic light-emitting guest materials, and organic host materials.

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

8. 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 5, or the organic functional layer is made of a mixture as described in claim 6, or the organic functional layer is prepared from the composition as described in claim 7.

9. The organic electronic device according to claim 8, characterized in that, The organic functional layer includes a hole transport layer and a light-emitting layer stacked together, wherein the hole transport layer is located between the first electrode and the light-emitting layer; the material of the hole transport layer includes at least one of the organic compounds.

10. A display panel, characterized in that, The display panel includes the organic electronic device as described in claim 8 or 9.

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