Organic compound, mixture, organic light-emitting device and display panel

Abstract

The invention relates to an organic compound, a mixture, an organic light-emitting device and a display panel, and the structural general formula of the organic compound is as shown in the formula (1). The compound can be used as a light-emitting auxiliary material to be applied to an organic light-emitting device for improving the light-emitting efficiency of the device and prolonging the service life of the device, and meanwhile, the device can keep relatively low driving voltage.

Description

Technical Field

[0001] The present application relates to the field of display technology, and in particular to an organic compound, a mixture, an organic light-emitting device and a display panel. Background Art

[0002] Organic electroluminescence (OEL) technology utilizes the photoelectric properties of organic materials to directly convert electrical energy into light. Organic light-emitting devices based on this technology typically consist of an anode, a cathode, and multiple organic functional layers, including a hole injection layer, a hole transport layer, a light-assisting layer, a light-emitting layer, an electron transport layer, and an electron injection layer. Each layer contains specific organic substances 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. The two combine to form excitons, which release light energy as they return to their ground state. As a representative example of OEL technology, organic light-emitting diodes (OLEDs) have made a significant splash in the flat-panel display and lighting sectors thanks to their numerous advantages, including self-luminescence, high brightness, high efficiency, low voltage, wide viewing angle, and high contrast. Their wide viewing angle, fast response, low voltage requirement, 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 vital role in improving the luminous efficiency and extending the service life of OLED devices. Carefully designed luminescent auxiliary materials can effectively balance the carrier transport in OLED devices, effectively inhibit the reverse migration of electrons, and promote the recombination of electrons and holes mainly in the central area of ​​the light-emitting layer, reducing the non-radiative recombination of excitons, thereby improving the luminous efficiency and extending the service life. Therefore, the development of more efficient new luminescent auxiliary materials to further optimize the hole and electron transport balance within the device is the key to improving device efficiency and life and maintaining a low driving voltage. This problem is a topic that researchers in this field urgently need to overcome. Summary of the Invention

[0004] The embodiments of the present application provide an organic compound, a mixture, an organic light-emitting device, and a display panel. The organic compound has good performance in transmitting and regulating charge balance, and can be used as a light-emitting auxiliary material in an organic light-emitting device to improve the luminous efficiency and extend the service life of the device, while also allowing the device to maintain a low driving voltage.

[0005] In order to achieve the above object, according to the first aspect of the present application, an organic compound is provided, the general structural formula of the organic compound is shown in formula (1):

[0006]

[0007] wherein R is selected from a combination of one or more of a hydrogen atom, a deuterium atom, an alkyl group having 1 to 12 carbon atoms, and a cycloalkyl group having 3 to 12 carbon atoms;

[0008] n is selected from any one of 0, 1, 2, 3, 4 and 5;

[0009] L is selected from a single bond, a substituted or unsubstituted aromatic group having 5 to 25 ring atoms, and a substituted or unsubstituted heteroaromatic group having 5 to 25 ring atoms;

[0010] Ar is selected from a combination of one or more substituted or unsubstituted aromatic groups having 5 to 25 ring atoms, and substituted or unsubstituted heteroaromatic groups having 5 to 25 ring atoms;

[0011] The substituent group of the substituted or unsubstituted group is selected from a combination of one or more of a deuterium atom, an aromatic group having 5 to 25 ring atoms, and a heteroaromatic group having 5 to 25 ring atoms;

[0012] The heteroatom in the heteroaromatic group is selected from one or more of a nitrogen atom, an oxygen atom or a sulfur atom.

[0013] According to the second aspect of the present application, a mixture is provided, which contains at least one organic compound as described above and at least one organic functional material, and the organic functional material is selected from at least one of hole injection materials, hole transport materials, luminescence 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 the present application, an organic light-emitting device is further provided, comprising:

[0015] a first electrode;

[0016] an organic functional layer, disposed on one side of the first electrode;

[0017] a second electrode, disposed on a side of the organic functional layer away from the first electrode;

[0018] The material of the organic functional layer includes at least one of the organic compounds mentioned above, or the material of the organic functional layer includes the mixture mentioned above.

[0019] According to a fourth aspect of the present application, a display panel is further provided, comprising the organic light-emitting device described above.

[0020] In the organic compounds, mixtures, organic light-emitting devices and display panels of the embodiments of the present application, an aromatic amine organic compound with fluorene-benzene-carbazole as the core structure is provided, and a phenyl group is used as an intermediate connecting group to connect the carbazole group to the No. 1 connection site of the 9,9-dimethylfluorene group, and the No. 4 connection site of the 9,9-dimethylfluorene is connected to the N atom of the diarylamine, forming a unique triarylamine compound with fluorene-benzene-carbazole as the core structure. This unique connection mode of fluorene-benzene-carbazole can effectively improve the lowest excited triplet energy level (T1) value of the organic compound molecule, promote the efficient transmission and effective utilization of charge, so that the organic compound has excellent hole transport performance, so that the organic compound has good transmission and charge balance performance, and can be used as a luminescent auxiliary material in an organic light-emitting device to improve the luminous efficiency of the device and extend the service life, while also allowing the device to maintain a low driving voltage. Therefore, when the organic compound of the present application is applied to an organic light-emitting device as a luminescent auxiliary material, not only can the driving voltage of the device be significantly reduced, but the luminous efficiency and service life of the device can also be greatly improved.

[0021] Other features and advantages of the present application will be described in detail in the subsequent detailed description. BRIEF DESCRIPTION OF THE DRAWINGS

[0022] To more clearly illustrate the technical solutions in the embodiments of the present application, the following briefly introduces the drawings required for describing the embodiments. Obviously, the drawings described below are only some embodiments of the present application. Those skilled in the art can also derive other drawings based on these drawings without inventive effort.

[0023] In order to more completely understand the present application and its beneficial effects, the following description will be given in conjunction with the accompanying drawings, wherein the same drawing numbers represent the same parts in the following description.

[0024] Figure 1 This is a schematic structural diagram of an organic light-emitting device provided in an embodiment of the present application;

[0025] Figure 2 This is a hydrogen nuclear magnetic resonance spectrum of the organic compound M1 provided in the examples of the present application.

[0026] Figure 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 DESCRIPTION

[0027] The technical solutions in the embodiments of the present application will be described clearly and completely below in conjunction with the drawings in the embodiments of the present application.

[0028] In the present application, "substituted" means that a hydrogen atom in a substituted group is replaced by a substituent.

[0029] In this application, hydrogen atoms include isotopes having different numbers of neutrons, namely protium, deuterium and tritium.

[0030] In this application, "substituted or unsubstituted" means that the defined group may be substituted or unsubstituted. When the defined group is substituted, it should be understood that it is optionally substituted by groups acceptable in the art, including but not limited to: deuterium atoms, cyano groups, isocyano groups, nitro groups, halogen atoms, C 1-10 Alkyl, C 1-10 Alkoxy, C 1-10 Alkylthio, C 6-30 Aryl, C 6-30 Aryloxy, C 6-30 Arylthio, C 3-30 Heteroaryl, C 1-30 Silane group, C 2-10 Alkylamino, C 6-30 arylamine group, or a combination of the above groups, etc.

[0031] In this application, the "number of ring atoms" refers to the number of atoms among the atoms that constitute the ring itself of a compound (e.g., a monocyclic compound, a condensed ring compound, a cross-linked compound, a carbocyclic compound, or a heterocyclic compound) that is formed by atoms bonded together to form a ring. When the ring is substituted with a substituent, the atoms contained in the substituent are not included in the ring atoms. The "number of ring atoms" described below also applies unless otherwise specified. For example, the number of ring atoms of a benzene ring is 6, the number of ring atoms of a naphthalene ring is 10, and the number of ring atoms of a thienyl group is 5.

[0032] In this application, "alkyl" may refer to a linear, branched and / or cyclic alkyl group. The number of carbon atoms in an alkyl group may be from 1 to 12. Phrases containing this term, for example, "C 1-9 “Alkyl” refers to an alkyl group containing 1 to 9 carbon atoms, and each occurrence can be independently 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, and the like.

[0033] In this application, "aryl or aromatic group" refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removing a hydrogen atom. It can be a monocyclic aromatic group, a condensed aromatic group, or a polycyclic aromatic group. For polycyclic rings, at least one is an aromatic ring system. For example, "substituted or unsubstituted aromatic group having 5 to 25 ring atoms" refers to an aromatic group containing 5 to 25 ring atoms, and the aromatic group is optionally further substituted; suitable examples include, but are not limited to: benzene, biphenyl, terphenyl, naphthalene, anthracene, fluoranthene, phenanthrene, triphenylene, perylene, tetracene, pyrene, benzopyrene, acenaphthene, fluorene and their derivatives. It is understood that multiple aromatic 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, diaryl ether system should also be included in the definition of aromatic group.

[0034] In the present application, the heteroaromatic group of 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 atoms as a ring atom and 5 to 25 ring atoms. Non-limiting examples of the heteroaromatic group of 5 to 25 ring atoms may include furanyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1 ,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, tetrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl, 1,3,5-triazinyl, benzofuranyl, benzisofuranyl, benzothiophenyl, benzisothiophenyl, indolyl, isoindolyl, indazolyl, benzimidazolyl, benzoxazolyl, benzisoxazolyl, benzothiazolyl, 2,1,3-Benzoxadiazole, quinolinyl, isoquinolinyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, benzotriazinyl, benzoxazinyl, purinyl, pteridinyl, indolizinyl, benzothiazinyl, acridinyl, phenanthrazinyl, phenathiazinyl, phenoxazinyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, naphthofuranyl, quinolinyl, isoquinolinyl, indolo[1,2-f]phenanthrene The present invention also includes, but is not limited to, benzo[4,5]imidazo[1,2-a]pyridinyl, imidazo[1,2-a]pyridinyl, benzofuran[3,2-c]quinolinyl, naphtho[1,2-b]benzofuranyl, naphtho[2,3-b]benzofuranyl, etc., and also includes aromatic combination groups with heteroatoms, but is not limited thereto.

[0035] In this application, "*" connected to a single bond indicates a connection or fusion site.

[0036] In the present application, when a linking site is not specified in a group, it means that an optional linking site in the group can be used as the linking site.

[0037] In the present application, the single bond to which the substituent is connected runs through the corresponding ring, indicating that the substituent can be attached to any position of the ring, for example R is connected to any substitutable position of the benzene ring.

[0038] The present invention provides an organic compound, the general structural formula of which is shown in Formula (1):

[0039]

[0040] wherein R is selected from a combination of one or more of a hydrogen atom, a deuterium atom, an alkyl group having 1 to 12 carbon atoms, and a cycloalkyl group having 3 to 12 carbon atoms;

[0041] n is selected from any one of 0, 1, 2, 3, 4 and 5;

[0042] L is selected from a single bond, a substituted or unsubstituted aromatic group having 5 to 25 ring atoms, and a substituted or unsubstituted heteroaromatic group having 5 to 25 ring atoms;

[0043] Ar is selected from a combination of one or more substituted or unsubstituted aromatic groups having 5 to 25 ring atoms, and substituted or unsubstituted heteroaromatic groups having 5 to 25 ring atoms;

[0044] The substituent group of the substituted or unsubstituted group is selected from a combination of one or more of a deuterium atom, an aromatic group having 5 to 25 ring atoms, and a heteroaromatic group having 5 to 25 ring atoms;

[0045] The heteroatom in the heteroaromatic group is selected from one or more of a nitrogen atom, an oxygen atom or a sulfur atom.

[0046] It can be understood that the “—” connected to R crossing the benzene ring means that R can be connected to any substitutable position of the benzene ring through the “—”.

[0047] In some embodiments, R is selected from a hydrogen atom, a deuterium atom, or any one of the following groups:

[0048]

[0049] Among them, “*” represents the connection site.

[0050] In some embodiments, L is selected from a single bond or a combination of any one or more of the following groups:

[0051]

[0052] Among them, “*” represents the connection site; the expression of “—” crossing the structure indicates that the connection site is any position on the structure that can form a bond.

[0053] In some embodiments, Ar is selected from any one of the following substituted or unsubstituted groups:

[0054]

[0055] Among them, “*” represents the connection site; “—” across the structure indicates that the connection site is any position on the structure that can form a bond;

[0056] The substituent group in the substituted or unsubstituted group is selected from one or more combinations of deuterium atoms, phenyl groups, naphthyl groups, biphenyl groups, fluorenyl groups, dibenzofuranyl groups, dibenzothienyl groups and carbazolyl groups.

[0057] It is understood that the hydrogen atoms on the Ar groups listed above may be replaced by one or more of a deuterium atom, a phenyl group, a naphthyl group, a biphenyl group, a fluorenyl group, a dibenzofuranyl group, a dibenzothiophenyl group and a carbazolyl group.

[0058] In some embodiments, the organic compound is selected from any one of the compounds represented by formula (2-1) to formula (2-3):

[0059]

[0060] In some embodiments, the organic compound is selected from any one of the following compounds:

[0061]

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076] In some embodiments, the above-mentioned organic compounds provided in the embodiments of the present application can be used as organic functional materials in electronic devices, in particular in OLED devices. Organic functional materials can be divided into hole injection materials (HIM), hole transport materials (HTM), luminescent auxiliary materials (Prime), electron transport materials (ETM), electron injection materials (EIM), electron blocking materials (EBM), hole blocking materials (HBM), luminescent guest materials (Guest Emitter) and host materials (Host Emitter). Among them, the host material can be divided into phosphorescent host materials, fluorescent host materials and host materials of thermally activated delayed fluorescence (TADF) luminescent materials. The above-mentioned organic compounds provided in the embodiments of the present application can be used as any one of them.

[0077] In a preferred embodiment, the organic compound represented by the above formula (1) provided in the embodiment of the present application can be used as a light-emitting auxiliary material.

[0078] In some embodiments, the glass transition temperature of the organic compound provided in the embodiments of the present application is Tg ≥ 100°C; in a preferred embodiment, Tg ≥ 120°C; in a more preferred embodiment, Tg ≥ 140°C; in a more preferred embodiment, Tg ≥ 160°C; in a most preferred embodiment, Tg ≥ 180°C.

[0079] The embodiment of the present application also provides a polymer, wherein the monomer of the polymer includes an organic compound represented by formula (1).

[0080] The present application also provides a mixture comprising at least one organic compound represented by formula (1) and at least one organic functional material, wherein the organic functional material is selected from at least one of a hole injection material, a hole transport material, a luminescence auxiliary material, an electron transport material, an electron injection material, an electron blocking material, a hole blocking material, an organic luminescent guest material, an organic host material, and an inorganic quantum dot. 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. It is understood that the organic functional material can be a small molecule or a polymer material.

[0081] The organic compounds provided in the embodiments of the present application can be used in vapor-deposition OLED devices. For example, in some embodiments, the molecular weight of the organic compounds provided in the embodiments of the present application is ≤1100 g / mol; in a preferred embodiment, the molecular weight of the organic compounds provided in the embodiments of the present application is ≤1000 g / mol; in a more preferred embodiment, the molecular weight of the organic compounds provided in the embodiments of the present application is ≤950 g / mol; in a more preferred embodiment, the molecular weight of the organic compounds provided in the embodiments of the present application is ≤900 g / mol; and in a most preferred embodiment, the molecular weight of the organic compounds provided in the embodiments of the present application is ≤800 g / mol.

[0082] The organic compounds provided in the embodiments of this application can also be used in printed OLED devices. For example, in some embodiments, the molecular weight of the organic compounds provided in the embodiments of this application is ≥500 g / mol; in a preferred embodiment, the molecular weight of the organic compounds provided in the embodiments of this application is ≥700 g / mol; in a more preferred embodiment, the molecular weight of the organic compounds provided in the embodiments of this application is ≥900 g / mol; and in an even more preferred embodiment, the molecular weight of the organic compounds provided in the embodiments of this application is ≥1000 g / mol.

[0083] An embodiment of the present application also provides a composition comprising at least one organic compound represented by formula (1) or the mixture thereof and at least one organic solvent.

[0084] The organic solvent is selected from any one of aromatic, heteroaromatic, ester, aromatic ketone, aromatic ether, aliphatic ketone, aliphatic ether, alicyclic, olefin, borate and phosphate compounds, or a mixture of two or more solvents. Preferably, the organic solvent is selected from aromatic or heteroaromatic solvents.

[0085] Examples of aromatic or heteroaromatic solvents suitable for the present application include, but are not limited to: p-diisopropylbenzene, pentylbenzene, tetralin, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, dipentylbenzene, tripentylbenzene, pentyltoluene, 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-furoate, ethyl 2-furoate, etc.

[0086] Examples of aromatic ketone-based solvents suitable for the present application include, but are not limited to: 1-tetralone, 2-tetralone, 2-(phenylepoxy)tetralone, 6-(methoxy)tetralone, acetophenone, propiophenone, benzophenone and their derivatives, such as 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylpropiophenone, 3-methylpropiophenone, 2-methylpropiophenone, etc.

[0087] Examples of aromatic ether solvents suitable for the present 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-ethyl acetate, 1,3-dipropoxybenzene, 1,2,4-trimethoxybenzene, 4-(1-propenyl)-1,2-dimethoxybenzene, 1,3-dimethoxybenzene, glycidyl phenyl ether, dibenzyl ether, 4-tert-butylanisole, trans-p-propenylanisole, 1,2-dimethoxybenzene, 1-methoxynaphthalene, diphenyl ether, 2-phenoxymethyl ether, 2-phenoxytetrahydrofuran, ethyl-2-naphthyl ether, and the like.

[0088] Examples of aliphatic ketone or aliphatic ether solvents suitable for the present application include, but are not limited to: 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2,5-hexanedione, 2,6,8-trimethyl-4-nonanone, fenchone, phorone, isophorone, di-n-amyl ketone, amyl ether, hexyl ether, dioctyl ether, ethylene glycol dibutyl ether, diethylene glycol diethyl ether, diethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, triethylene glycol ethyl methyl ether, triethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, etc.

[0089] Examples of borate or phosphate ester solvents suitable for the present application include, but are not limited to, alkyl octanoates, alkyl sebacates, alkyl stearates, alkyl benzoates, alkyl phenylacetates, alkyl cinnamates, alkyl oxalates, alkyl maleates, alkyl lactones, alkyl oleates, etc. Octyl octanoate, diethyl sebacate, diallyl phthalate, and isononyl isononanoate are particularly preferred.

[0090] In some preferred embodiments, the composition provided in the embodiments of the present application comprises 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, chloroform, chlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1,4-dioxane, acetone, methyl ethyl ketone, 1,2-dichloroethane, 3-phenoxytoluene, 1,1,1-trichloroethane, 1,1,2,2-tetrachloroethane, ethyl acetate, butyl acetate, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, tetralin, decalin, indene and / or mixtures thereof.

[0091] In some preferred embodiments, solvents particularly suitable for the present application are solvents having a Hansen solubility parameter within the following range: δd (dispersion force) between 17.0 and 23.2 MPa. 1 / 2 range, especially in the range of 18.5~21.0MPa 1 / 2 range; δp (polar force) is 0.2~12.5MPa 1 / 2 range, especially in the range of 2.0~6.0MPa 1 / 2 range; δh (hydrogen bond force) is 0.9~14.2MPa 1 / 2 range, especially in the range of 2.0~6.0MPa 1 / 2 range.

[0092] In the compositions provided in the examples of this application, the boiling point parameters of the organic solvent should be considered when selecting. In this application, the boiling point of the organic solvent is ≥150°C; preferably, the boiling point of the organic solvent is ≥180°C; more preferably, the boiling point of the organic solvent is ≥200°C; more preferably, the boiling point of the organic solvent is ≥250°C; most preferably, the boiling point of the organic solvent is ≥275°C or ≥300°C. Boiling points within these ranges are beneficial for preventing clogging of the nozzles of the inkjet print head. The organic solvent can evaporate from the solvent system to form a film containing the organic functional material.

[0093] In some embodiments, the composition provided in the examples of the present application is a solution. In another embodiment, the composition provided in the examples of the present application is a suspension.

[0094] The compositions provided in the embodiments of the present 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 %.

[0095] In some embodiments, the mass fraction of the organic compound or the mixture in the composition is 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%.

[0096] The present application also provides an embodiment of the use of the composition as a coating or printing ink in the preparation of an organic electronic device. A particularly preferred use is to use the composition as a coating or printing ink and prepare an organic electronic device by a printing or coating preparation method.

[0097] Suitable printing or coating techniques include, but are not limited to, inkjet printing, nozzle printing, letterpress printing, screen printing, dip coating, spin coating, blade coating, roller printing, twist roller printing, lithographic printing, flexographic printing, rotary printing, spray coating, brush coating, pad printing, and slot extrusion coating. Gravure printing, nozzle printing, and inkjet printing are preferred. The solution or suspension may further include one or more components, such as surfactants, lubricants, wetting agents, dispersants, hydrophobic agents, and adhesives, to adjust viscosity, film-forming properties, and enhance adhesion. Relevant printing techniques and their associated requirements for the relevant solutions, such as solvent, concentration, and viscosity, are discussed in detail.

[0098] The organic compound, the mixture or the composition provided in this application can be applied in organic electronic devices.

[0099] The organic electronic devices include, but are 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 emitting diodes (OPEDs). Particularly preferably, the organic electronic device is an organic electroluminescent device, such as an OLED, an OLEEC, or an OLEFET.

[0100] In the embodiment of the present application, the organic compound is preferably applied to the light-emitting auxiliary layer of the OLED device.

[0101] like Figure 1 As shown, an embodiment of the present application further provides an organic light-emitting device 100, which is an organic electronic device, and the organic light-emitting device 100 includes a first electrode 11, a second electrode 18 arranged opposite to the first electrode 11, and an organic functional layer located between the first electrode 11 and the second electrode 18, wherein 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 mixture described above, or the organic functional layer is prepared by using the organic compound, mixture or composition described above.

[0102] In one embodiment, the first electrode 11 is an anode, and the second electrode 18 is a cathode.

[0103] 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 luminescence auxiliary layer, and an organic light-emitting layer. Preferably, the organic functional layer comprises at least a stacked luminescence auxiliary layer and an organic light-emitting layer.

[0104] Specifically, the organic light-emitting device 100 further includes a substrate 1 , and the first electrode 11 is disposed on the substrate 1 .

[0105] In a 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 stacked in sequence on the first electrode 11, wherein the material of the light-emitting auxiliary layer 14 includes at least one organic compound represented by formula (1).

[0106] In some embodiments, the organic light-emitting device 100 includes any one of a red organic light-emitting device, a blue organic light-emitting device, and a green organic light-emitting device. In other words, the organic compound represented by formula (1) provided in the embodiments of the present application can be used as a red light-emitting auxiliary material, a blue light-emitting auxiliary material, and a green light-emitting auxiliary material.

[0107] In a preferred embodiment, the organic compound represented by formula (1) is a blue light emitting auxiliary material.

[0108] Specifically, the organic light-emitting device 100 includes but is not limited to an organic light-emitting diode (OLED), an organic photovoltaic cell (OPV), an organic light-emitting cell (OLEEC), an organic field-effect transistor (OFET), an organic light-emitting field-effect transistor (OLEFET), an organic laser, an organic spintronic device, an organic sensor, and an organic plasmon emission diode (OPED), etc., and particularly preferred are organic electroluminescent devices such as OLED, OLEEC, or OLEFET.

[0109] The anode may comprise a conductive metal or metal oxide, or a conductive polymer. The anode can readily inject holes into the hole injection layer (HIL) or 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 energy level or valence band energy level of the light-emitting material in the light-emitting layer or the p-type semiconductor material serving as the HIL or HTL or electron blocking layer (EBL) is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. Examples of anode materials include, but are not limited to, Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO, aluminum-doped zinc oxide (AZO), and the like. Other suitable anode materials are known and can be readily selected for use by one of ordinary skill in the art. The anode material can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), and the like. In certain embodiments, the anode is patterned. Patterned ITO conductive substrates are commercially available and can be used to prepare devices according to the present application.

[0110] The cathode may comprise a conductive metal or metal oxide. The cathode can readily inject electrons 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 energy level or conduction band energy level of the light-emitting body in the light-emitting layer or the n-type semiconductor material serving as the electron injection layer (EIL) or electron transport layer (ETL) or hole blocking layer (HBL) is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. In principle, all materials that can be used as cathodes for OLEDs may be used as cathode materials for the devices of the present application. Examples of cathode materials include, but are not limited to, Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloy, BaF2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO, and the like. The cathode material may 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), and the like.

[0111] In some embodiments, the light-emitting material in the light-emitting layer of the organic light-emitting device 100 provided in the embodiments of the present application is selected from a singlet light-emitting body, a triplet light-emitting body or a TADF material.

[0112] In some embodiments, the thickness of the organic functional layer in the organic light-emitting device 100 provided in the embodiments of the present 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.

[0113] The organic light-emitting device 100 provided in the embodiment of the present application can be applied to various electronic devices, including but not limited to display devices, lighting devices, light sources, sensors, etc.

[0114] An embodiment of the present application further provides an electronic device, which includes the organic electronic device 100 provided in an embodiment of the present application. The electronic device includes but is not limited to a display device, a lighting device, a light source, a sensor, and the like.

[0115] An embodiment of the present application further provides a display panel, which includes the organic light-emitting device 100 described above.

[0116] The present application will be described below 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 attached claims summarize the scope of protection of the present application. Under the guidance of the concept of the present invention, those skilled in the art should realize that certain 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. Specific embodiments

[0118] The organic compounds and their preparation methods of the present invention are further described in detail below with reference to specific examples. Unless otherwise specified, the raw materials used in the following examples are all commercially available products.

[0119] (1) Synthesis Examples of Organic Compounds

[0120] Example 1

[0121] The synthetic route of organic compound M1 is as follows:

[0122]

[0123] Synthesis of intermediate 1-3:

[0124] Compound 1-1 (10 mmol), compound 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, and the reaction solution was heated to 120°C and stirred for 6 h under a nitrogen atmosphere; the reaction system was cooled to room temperature, and a portion of the solvent was removed by rotary evaporation using a rotary evaporator; then, the reaction solution was extracted three times with dichloromethane and water; then, the organic phase was dried to obtain a crude product; finally, the crude product was further purified by column chromatography to obtain intermediate 1-3, and the yield of intermediate 1-3 was 90%. The mass spectrometry result was m / z [H + ]=472.

[0125] Synthesis of organic compound M1:

[0126] The intermediate 1-3 (10 mmol), compound 1-4 (10 mmol), Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were dissolved in a mixed solvent of toluene, ethanol and water. The reaction solution was heated to 100°C and stirred for 8 hours under a nitrogen atmosphere. After the reaction system was cooled to room temperature, a portion of the solvent was removed by a rotary evaporator. The reaction solution was then extracted three times with dichloromethane and water. After separation, the organic phase was dried to obtain a crude product. Finally, the crude product was purified by column chromatography to obtain an organic compound M1. The yield of the organic compound M1 was 88%. The mass spectrometry result was m / z [H + ]=678, elemental analysis structure (molecular formula C 51 H 38 N2) has a test value of C, 90.20; H, 5.64; N, 4.16, and the H NMR spectrum of the organic compound M1 ( 1 H-NMR spectrum) Figure 2 shown.

[0127] Example 2

[0128] The synthetic route of organic compound M2 is as follows:

[0129]

[0130] Synthesis of Intermediate 2-3 The synthesis method of Intermediate 1-3 in Reference Example 1 was used. The yield of Intermediate 2-3 was 87%. The mass spectrometry result was m / z [H + ]=486.

[0131] Synthesis of Organic Compound M2 Referring to the synthesis method of Organic Compound M1 in Example 1, the yield of Organic Compound M2 was 89%, and the mass spectrum result was m / z [H + ]=692, elemental analysis structure (molecular formula C 52 H 40 The test values ​​of N2) are C, 90.10; H, 5.83; N, 4.07.

[0132] Example 3

[0133] The synthetic route of organic compound M3 is as follows:

[0134]

[0135] The synthesis of intermediate 3-3 was carried out according to the method for synthesizing intermediate 1-3 in reference example 1. The yield of intermediate 3-3 was 88%, and the mass spectrum result was m / z [H + ]=528.

[0136] The synthesis of organic compound M3 was carried out according to the method for synthesizing organic compound M1 in reference example 1. The yield of organic compound M3 was 91%, and the mass spectrum result was m / z [H + ]=734, elemental analysis structure (molecular formula C 55 H 46 The test values ​​of N2) are C, 89.90; H, 6.30; N, 3.80.

[0137] Example 4

[0138] The synthetic route of organic compound M4 is as follows:

[0139]

[0140] The synthesis of intermediate 4-3 was carried out according to the method for synthesizing intermediate 1-3 in reference example 1. The yield of intermediate 4-3 was 86%, and the mass spectrum result was m / z [H + ]=554.

[0141] The synthesis of organic compound M4 was carried out according to the method for synthesizing organic compound M1 in Example 1. The yield of organic compound M4 was 92%. The mass spectrum result was m / z [H+ ]=760, elemental analysis structure (molecular formula C 57 H 48 The test values ​​of N2) are C, 89.98; H, 6.37; N, 3.65.

[0142] Example 5

[0143] The synthetic route of organic compound M5 is as follows:

[0144]

[0145] The synthesis of intermediate 5-3 was carried out according to the method for synthesizing intermediate 1-3 in reference example 1. The yield of intermediate 5-3 was 89%, and the mass spectrum result was m / z [H + ]=606.

[0146] The synthesis of organic compound M5 was carried out according to the method for synthesizing organic compound M1 in reference example 1. The yield of organic compound M5 was 86%, and the mass spectrum result was m / z [H + ]=813, elemental analysis structure (molecular formula C 61 H 52 The test values ​​of N2) are C, 90.10; H, 6.44; N, 3.47.

[0147] Example 6

[0148] The synthetic route of organic compound M6 is as follows:

[0149]

[0150] The synthesis of intermediate 6-3 was carried out according to the method for synthesizing intermediate 1-3 in reference example 1. The yield of intermediate 6-3 was 87%. The mass spectrum result was m / z [H + ]=522.

[0151] The synthesis of organic compound M6 was carried out according to the method for synthesizing organic compound M1 in Example 1. The yield of organic compound M6 was 89%, and the mass spectrum result was m / z [H + ]=728, elemental analysis structure (molecular formula C 55 H 40 The test values ​​of N2) are C, 90.65; H, 5.52; N, 3.83.

[0152] Example 7

[0153] The synthetic route of organic compound M7 is as follows:

[0154]

[0155] The synthesis of intermediate 7-3 was carried out according to the method for synthesizing intermediate 1-3 in reference example 1. The yield of intermediate 7-3 was 84%, and the mass spectrum result was m / z [H + ]=512.

[0156] The synthesis of organic compound M7 was carried out according to the method for synthesizing organic compound M1 in Example 1. The yield of organic compound M7 was 86%, and the mass spectrum result was m / z [H + ]=718, elemental analysis structure (molecular formula C 54 H 42 The test values ​​of N2) are C, 90.20; H, 5.88; N, 3.90.

[0157] Example 8

[0158] The synthetic route of organic compound M8 is as follows:

[0159]

[0160] The synthesis of intermediate 8-3 was carried out according to the method for synthesizing intermediate 1-3 in reference example 1. The yield of intermediate 8-3 was 86%, and the mass spectrum result was m / z [H + ]=486.

[0161] The synthesis of organic compound M8 was carried out according to the method for synthesizing organic compound M1 in Example 1. The yield of organic compound M8 was 88%, and the mass spectrum result was m / z [H + ]=692, elemental analysis structure (molecular formula C 51 H 36 The test values ​​of N2O) are C, 88.39; H, 5.25; N, 4.03; O, 2.33.

[0162] Example 9

[0163] The synthetic route of organic compound M9 is as follows:

[0164]

[0165] The synthesis of intermediate 9-3 was carried out according to the method for synthesizing intermediate 1-3 in reference example 1. The yield of intermediate 9-3 was 84%, and the mass spectrum result was m / z [H + ]=588.

[0166] Synthesis of Organic Compound M9 The synthesis method of organic compound M1 in reference example 1 was used. The yield of organic compound M9 was 86%. The mass spectrum result was m / z [H + ]=795, elemental analysis structure (molecular formula C 60 H 46The test values ​​of N2) are C, 90.62; H, 5.84; N, 3.53.

[0167] Example 10

[0168] The synthetic route of organic compound M10 is as follows:

[0169]

[0170] The synthesis of intermediate 10-3 was carried out according to the method for synthesizing intermediate 1-3 in reference example 1. The yield of intermediate 10-3 was 83%. The mass spectrometry result was m / z [H + ]=562.

[0171] Synthesis of Organic Compound M10 The synthesis method of organic compound M1 in reference example 1 was used. The yield of organic compound M10 was 85%. The mass spectrum result was m / z [H + ]=768, elemental analysis structure (molecular formula C 57 H 40 The test values ​​of N2O) were C, 89.03; H, 5.24; N, 3.64; O, 2.08.

[0172] Example 11

[0173] The synthetic route of organic compound M11 is as follows:

[0174]

[0175] The synthesis of intermediate 11-3 was carried out according to the method for synthesizing intermediate 1-3 in reference example 1. The yield of intermediate 11-3 was 83%. The mass spectrum result was m / z [H + ]=548.

[0176] Synthesis of Organic Compound M11 The method for synthesizing Organic Compound M1 in Reference Example 1 was used. The yield of Organic Compound M11 was 85%. The mass spectrometry result was m / z [H + ]=754, elemental analysis structure (molecular formula C 57 H 42 The test values ​​of N2) are C, 90.66; H, 5.60; N, 3.74.

[0177] Example 12

[0178] The synthetic route of organic compound M12 is as follows:

[0179]

[0180] The synthesis of intermediate 12-3 was carried out according to the method for synthesizing intermediate 1-3 in reference example 1. The yield of intermediate 12-3 was 83%. The mass spectrometry result was m / z [H + ]=445.

[0181] The synthesis of organic compound M12 was carried out according to the method for synthesizing organic compound M1 in reference example 1. The yield of organic compound M12 was 88%, and the mass spectrum result was m / z [H + ]=652, elemental analysis structure (molecular formula C 49 H 36 The test values ​​of N2) are C, 90.12; H, 5.57; N, 4.31.

[0182] Example 13

[0183] The synthetic route of organic compound M13 is as follows:

[0184]

[0185] The synthesis of intermediate 13-3 was carried out according to the method for synthesizing intermediate 1-3 in reference example 1. The yield of intermediate 13-3 was 86%, and the mass spectrum result was m / z [H + ]=521.

[0186] Synthesis of Organic Compound M13 The synthesis method of organic compound M1 in reference example 1 was used. The yield of organic compound M13 was 85%. The mass spectrum result was m / z [H + ]=728, elemental analysis structure (molecular formula C 55 H 40 The test values ​​of N2) are C, 90.60; H, 5.55; N, 3.85.

[0187] Example 14

[0188] The synthetic route of organic compound M14 is as follows:

[0189]

[0190] The synthesis of intermediate 14-3 was carried out according to the method for synthesizing intermediate 1-3 in reference example 1. The yield of intermediate 14-3 was 84%. The mass spectrometry result was m / z [H + ]=598.

[0191] Synthesis of Organic Compound M14 The synthesis method of organic compound M1 in reference example 1 was used. The yield of organic compound M14 was 87%. The mass spectrum result was m / z [H + ]=805, elemental analysis structure (molecular formula C 61 H 44The test values ​​of N2) are C, 91.00; H, 5.53; N, 3.45.

[0192] Example 15

[0193] The synthetic route of organic compound M15 is as follows:

[0194]

[0195] The synthesis of intermediate 15-3 was carried out according to the method for synthesizing intermediate 1-3 in reference example 1. The yield of intermediate 15-3 was 82%. The mass spectrum result was m / z [H + ]=598.

[0196] Synthesis of Organic Compound M15 The synthesis method of organic compound M1 in reference example 1 was used. The yield of organic compound M15 was 85%. The mass spectrum result was m / z [H + ]=805, elemental analysis structure (molecular formula C 61 H 44 The test values ​​of N2) are C, 90.98; H, 5.52; N, 3.49.

[0197] Example 16

[0198] The synthetic route of organic compound M16 is as follows:

[0199]

[0200] The synthesis of intermediate 16-3 was carried out according to the method for synthesizing intermediate 1-3 in reference example 1. The yield of intermediate 16-3 was 83%. The mass spectrometry result was m / z [H + ]=598.

[0201] Synthesis of Organic Compound M16 The synthesis method of organic compound M1 in reference example 1 was used. The yield of organic compound M16 was 84%. The mass spectrum result was m / z [H + ]=805, elemental analysis structure (molecular formula C 61 H 44 The test values ​​of N2) are C, 90.96; H, 5.54; N, 3.49.

[0202] Example 17

[0203] The synthetic route of organic compound M17 is as follows:

[0204]

[0205] The synthesis of intermediate 17-3 was carried out according to the method for synthesizing intermediate 1-3 in reference example 1. The yield of intermediate 17-3 was 85%, and the mass spectrum result was m / z [H+ ]=571.

[0206] Synthesis of Organic Compound M17 The synthesis method of organic compound M1 in reference example 1 was used. The yield of organic compound M17 was 82%. The mass spectrum result was m / z [H + ]=778, elemental analysis structure (molecular formula C 59 H 42 The test values ​​of N2) are C, 90.97; H, 5.43; N, 3.60.

[0207] Example 18

[0208] The synthetic route of organic compound M18 is as follows:

[0209]

[0210] The synthesis of intermediate 18-3 was carried out according to the method for synthesizing intermediate 1-3 in reference example 1. The yield of intermediate 18-3 was 86%, and the mass spectrum result was m / z [H + ]=496.

[0211] Synthesis of Organic Compound M18 The synthesis method of organic compound M1 in reference example 1 was used. The yield of organic compound M18 was 84%. The mass spectrum result was m / z [H + ]=702, elemental analysis structure (molecular formula C 53 H 38 The test values ​​of N2) are C, 90.55; H, 5.44; N, 4.02.

[0212] Example 19

[0213] The synthetic route of organic compound M19 is as follows:

[0214]

[0215] The synthesis of intermediate 19-3 was carried out according to the method for synthesizing intermediate 1-3 in reference example 1. The yield of intermediate 19-3 was 85%, and the mass spectrum result was m / z [H + ]=573.

[0216] Synthesis of Organic Compound M19 The synthesis method of organic compound M1 in reference example 1 was used. The yield of organic compound M19 was 82%. The mass spectrum result was m / z [H + ]=780, elemental analysis structure (molecular formula C 59 H 44 The test values ​​of N2) are C, 90.73; H, 5.68; N, 3.59.

[0217] Example 20

[0218] The synthetic route of organic compound M20 is as follows:

[0219]

[0220] The synthesis of intermediate 20-3 was carried out according to the method for synthesizing intermediate 1-3 in reference example 1. The yield of intermediate 20-3 was 86%, and the mass spectrum result was m / z [H + ]=635.

[0221] The synthesis of organic compound M20 was carried out according to the method for synthesizing organic compound M1 in reference example 1. The yield of organic compound M20 was 80%, and the mass spectrum result was m / z [H + ]=842, elemental analysis structure (molecular formula C 64 H 46 The test values ​​of N2) are C, 91.16; H, 5.53; N, 3.31.

[0222] Example 21

[0223] The synthetic route of organic compound M21 is as follows:

[0224]

[0225] The synthesis of intermediate 21-3 was carried out according to the method for synthesizing intermediate 1-3 in reference example 1. The yield of intermediate 21-3 was 86%, and the mass spectrum result was m / z [H + ]=574.

[0226] Synthesis of Organic Compound M21 The synthesis method of organic compound M1 in reference example 1 was used. The yield of organic compound M21 was 80%. The mass spectrum result was m / z [H + ]=781, elemental analysis structure (molecular formula C 59 H 44 The test values ​​of N2) are C, 90.70; H, 5.67; N, 3.63.

[0227] Example 22

[0228] The synthetic route of organic compound M22 is as follows:

[0229]

[0230] The synthesis of intermediate 22-3 was carried out according to the method for synthesizing intermediate 1-3 in reference example 1. The yield of intermediate 22-3 was 83%. The mass spectrometry result was m / z [H + ]=561.

[0231] The synthesis of organic compound M22 was carried out according to the method for synthesizing organic compound M1 in reference example 1. The yield of organic compound M22 was 85%, and the mass spectrum result was m / z [H + ]=767, elemental analysis structure (molecular formula C 57 H 41 The test values ​​of N3) are C, 89.15; H, 5.38; N, 5.47.

[0232] Example 23

[0233] The synthetic route of organic compound M23 is as follows:

[0234]

[0235] The synthesis of intermediate 23-3 was carried out according to the method for synthesizing intermediate 1-3 in reference example 1. The yield of intermediate 23-3 was 82%. The mass spectrum result was m / z [H + ]=561.

[0236] The synthesis of organic compound M23 was carried out according to the method for synthesizing organic compound M1 in reference example 1. The yield of organic compound M23 was 86%, and the mass spectrum result was m / z [H + ]=767, elemental analysis structure (molecular formula C 57 H 41 The test values ​​of N3) are C, 89.15; H, 5.38; N, 5.47.

[0237] Example 24

[0238] The synthetic route of organic compound M24 is as follows:

[0239]

[0240] The synthesis of intermediate 24-3 was carried out according to the method for synthesizing intermediate 1-3 in reference example 1. The yield of intermediate 24-3 was 85%, and the mass spectrum result was m / z [H + ]=561.

[0241] The synthesis of organic compound M24 was carried out according to the method for synthesizing organic compound M1 in reference example 1. The yield of organic compound M24 was 83%. The mass spectrum result was m / z [H + ]=768, elemental analysis structure (molecular formula C 57 H 40 The test values ​​of N2O) were C, 89.03; H, 5.24; N, 3.64; O, 2.08.

[0242] Example 25

[0243] The synthetic route of organic compound M25 is as follows:

[0244]

[0245] The synthesis of intermediate 25-3 was carried out according to the method for synthesizing intermediate 1-3 in reference example 1. The yield of intermediate 25-3 was 82%. The mass spectrometry result was m / z [H + ]=587.

[0246] Synthesis of Organic Compound M25 The synthesis method of organic compound M1 in reference example 1 was used. The yield of organic compound M25 was 88%. The mass spectrum result was m / z [H + ]=795, elemental analysis structure (molecular formula C 60 H 46 The test values ​​of N2) are C, 90.64; H, 5.83; N, 3.52.

[0247] Example 26

[0248] The synthetic route of organic compound M26 is as follows:

[0249]

[0250] The synthesis of intermediate 26-3 was carried out according to the method for synthesizing intermediate 1-3 in reference example 1. The yield of intermediate 26-3 was 85%. The mass spectrometry result was m / z [H + ]=634.

[0251] The synthesis of organic compound M26 was carried out according to the method for synthesizing organic compound M1 in reference example 1. The yield of organic compound M26 was 83%. The mass spectrum result was m / z [H + ]=841, elemental analysis structure (molecular formula C 64 H 44 The test values ​​of N2) are C, 91.40; H, 5.27; N, 3.33.

[0252] Example 27

[0253] The synthetic route of organic compound M27 is as follows:

[0254]

[0255] The synthesis of intermediate 27-3 was carried out according to the method for synthesizing intermediate 1-3 in reference example 1. The yield of intermediate 27-3 was 87%. The mass spectrometry result was m / z [H + ]=587.

[0256] The synthesis of organic compound M27 was carried out according to the method for synthesizing organic compound M1 in Example 1. The yield of organic compound M27 was 84%. The mass spectrometry result was m / z [H + ]=678, elemental analysis structure (molecular formula C 51 H 38 The test values ​​of N2) are C, 90.21; H, 5.63; N, 4.16.

[0257] Example 28

[0258] The synthetic route of organic compound M28 is as follows:

[0259]

[0260] The synthesis of intermediate 28-3 was carried out according to the method for synthesizing intermediate 1-3 in reference example 1. The yield of intermediate 28-3 was 88%, and the mass spectrum result was m / z [H + ]=587.

[0261] Synthesis of Organic Compound M28 The synthesis method of organic compound M1 in reference example 1 was used. The yield of organic compound M28 was 86%. The mass spectrum result was m / z [H + ]=678, elemental analysis structure (molecular formula C 51 H 38 The test values ​​of N2) are C, 90.22; H, 5.61; N, 4.17.

[0262] Example 29

[0263] The synthetic route of organic compound M29 is as follows:

[0264]

[0265] The synthesis of intermediate 29-3 was carried out according to the method for synthesizing intermediate 1-3 in reference example 1. The yield of intermediate 29-3 was 85%, and the mass spectrum result was m / z [H + ]=527.

[0266] Synthesis of Organic Compound M29 The synthesis method of organic compound M1 in reference example 1 was used. The yield of organic compound M29 was 86%. The mass spectrum result was m / z [H + ]=733, elemental analysis structure (molecular formula C 55 H 35 The test values ​​of D5N2) are C, 90.03; H (including D), 6.16; N, 3.81.

[0267] Comparative Example

[0268] The present application also provides Comparative Example 1 and Comparative Example 2. The comparative compounds in Comparative Example 1 and Comparative Example 2 are respectively denoted as "Ref-01" and "Ref-02", and their chemical structures are shown below:

[0269]

[0270] (2) Energy levels of organic compounds

[0271] In the embodiments of the present application, the energy level of the organic compound plays a key role. The highest occupied molecular orbital (HOMO) energy level and the lowest unoccupied molecular orbital (LUMO) energy level of the organic compound M1 to organic compound M20 obtained in Examples 1 to 29 of the present application, as well as the comparative compound Ref-01 and the comparative compound Ref-02 can be obtained by theoretical calculation. Specifically, the energy level of the organic compound material can be obtained by quantum calculation, such as by Gaussian09W (Gaussian Inc.) using TD-DFT (time-dependent density functional theory). The specific simulation method can be found in WO2011141110. In the description of the embodiments of the present application, the ground state (S0) configuration is calculated according to density functional theory (DFT) under B3LYP / 6-31G (d) or B3LYP / 6-31G (d, p) basis set. The HOMO and LUMO values ​​of the materials were calculated using time-dependent density functional theory (TD-DFT) with 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 of the materials were calculated using the following calibration formulas; S1, T1, and the resonance factor f(S1) were used directly.

[0272] HOMO(eV)=((HOMO(G)×27.212)-0.9899) / 1.1206;

[0273] LUMO(eV)=((LUMO(G)×27.212)-2.0041) / 1.385;

[0274] Wherein, HOMO (G) and LUMO (G) are the direct calculation results of Gaussian 09W, with units in Hartree, and HOMO (eV) and LUMO (eV) are the converted results. The energy level test results of organic compounds M1 to M20 obtained in Examples 1 to 29 of the present application, as well as comparative compounds Ref-01 and Ref-02 are shown in Table 1:

[0275] Table 1

[0276]

[0277]

[0278]

[0279] As shown in Table 1, the HOMO energy levels of the organic compounds M1 to M29 provided in the examples of the present application are comparable to those of the comparative compounds Ref-01 and Ref-02, indicating that these organic compounds are suitable as luminescent auxiliary materials for optimizing the hole transport rate, reducing the energy barrier between the hole transport layer and the light-emitting layer, and improving device performance. However, the examples of the present application, through the introduction of 9,9-dimethylfluorene and the coordinated regulation of the precise connection sites, make the E T1 The energy level is significantly higher than that of the comparative compounds Ref-01 and Ref-02. T1 The energy levels indicate that when the organic compounds M1 to M29 provided in the embodiments of the present application are used as luminescent auxiliary materials, electron back transport can be more effectively prevented, ensuring that excitons are smoothly formed in the luminescent layer and emit light, thereby helping to improve luminescence efficiency and device stability.

[0280] (3) Preparation and characterization of OLED devices

[0281] The following is a detailed description of the preparation method and process of the OLED device using the organic compounds provided in the embodiments of the present application through specific device embodiments. In the following preparation method for preparing OLED devices, ITO conductive glass is used as the anode substrate, PD is used as the hole injection material, HT is used as the hole transport material, BH is used as the main material of the light-emitting layer, BD is used as the doping material of the light-emitting layer, ET and Liq are used as electron transport materials, Liq is used as the electron injection material, and Al is used as the cathode material. In addition, the organic compounds M1 to M29 of the aforementioned synthesis examples and the comparative compounds Ref-01 and Ref-02 are used as luminescent auxiliary materials to prepare corresponding OLED devices. Among them, the chemical structures of PD, HT, BH, BD, ET and Liq are as follows:

[0282]

[0283]

[0284] It should be noted that the embodiments of the present application are described using the preparation process of a blue light OLED device as an example, but are not limited thereto.

[0285] The following is a detailed description of the preparation process of OLED devices using the above materials through specific examples. In the embodiment of the present application, the structure of the prepared OLED device is: ITO / PD:HT (3:97, 10nm) / HT (130nm) / organic compound M1 (90nm) / BH:BD (3%, 40nm) / ET:Liq (5:5, 30nm) / Liq (1nm) / Al (100nm). Taking the preparation method of the OLED device using the organic compound M1 as the light-emitting auxiliary material as an example, the prepared OLED device is recorded as "OLED-1 device". The preparation method of the OLED-1 device includes the following steps:

[0286] a. Cleaning of the conductive glass substrate: using chloroform, ketone, isopropyl alcohol for cleaning, followed by ultraviolet ozone plasma treatment;

[0287] b. Preparation of functional layer: First, the ITO substrate was moved into a vacuum vapor deposition device and placed in a high vacuum (1×10 -6 mbar), using resistance heating evaporation to The hole injection materials PD and HT were evaporated on ITO at an evaporation rate of 3:97 to obtain a hole injection layer with a thickness of 10 nm. The hole transport material HT was evaporated on the hole injection layer at a deposition rate of 100 nm to obtain a hole transport layer with a thickness of 130 nm. The organic compound M1 provided in the above embodiment was evaporated on the hole transport layer at a deposition rate of 100 nm to obtain a light-emitting auxiliary layer with a thickness of 90 nm; BH and BD were evaporated on the light-emitting auxiliary layer at a rate of 97:3, and a light-emitting layer with a thickness of 40 nm was obtained. Subsequently, the electron transport materials ET and Liq were placed in different evaporation crucibles in a vacuum chamber and heated in a high vacuum environment (1×10 -6 ET and Liq were co-deposited at a weight ratio of 5:5 under 30 mbar to form an electron transport layer with a thickness of 30 nm on the light-emitting layer; The electron injection material Liq was evaporated on the electron transport layer at a deposition rate of 1 nm to obtain an electron injection layer with a thickness of 1 nm; The cathode material Al is evaporated on the electron injection layer at an evaporation rate of , to obtain a cathode with a thickness of 100 nm;

[0288] c. Packaging: The device was packaged with UV-curable resin in a nitrogen glove box to obtain the OLED-1 device.

[0289] Referring to the preparation method for device OLED-1, organic compounds M2 to M29 synthesized in the above examples were selected as auxiliary luminescence materials for OLED devices, respectively, to produce devices OLED-2 to OLED-29. It should be understood that, in the preparation methods for devices OLED-1 to OLED-29, other experimental conditions were identical except for the auxiliary luminescence materials.

[0290] Furthermore, referring to the preparation methods of the device examples, comparative compounds Ref-01 and Ref-02 were used as luminescence-assisting materials, respectively, to produce comparative example OLED-Ref-01 and OLED-Ref-02 devices. Compared to the preparation method of the OLED-1 device, the preparation methods of OLED-Ref-01 and OLED-Ref-02 devices were identical except for the luminescence-assisting materials.

[0291] In the examples of this application, the current-voltage (JV) characteristics of OLED-1 to OLED-29, OLED-Ref-01 and OLED-Ref-02 devices were characterized, and important parameters such as luminous efficiency and service life were recorded. The results are shown in Table 2. The luminous efficiency is the current density of 10 mA cm -2 The lifespan (LT95) is the time it takes for the brightness to drop to 95% of the initial brightness @1000nits under constant current.

[0292] Table 2

[0293]

[0294]

[0295] As shown in Table 2, when organic compounds M1 to M29 provided in the Examples of this application are used as blue light-emitting auxiliary materials, the resulting OLED-1 to OLED-29 devices exhibit significantly better luminous efficiency and lifetime than the OLED-Ref-01 and OLED-Ref-02 devices provided in the comparative examples. Furthermore, compared to the OLED-Ref-01 and OLED-Ref-02 devices, the OLED-1 to OLED-29 devices provided in the Examples of this application exhibit lower driving voltages. Therefore, the synergistic regulation of the introduction of 9,9-dimethylfluorene and precise attachment sites in the Examples of this application enables superior overall device performance.

[0296] As can be seen, the organic compounds M1 to M29 provided in the examples of this application significantly outperformed similar materials provided in the comparative examples (comparative compounds Ref-01 and Ref-02) in terms of performance as blue light-emitting auxiliary materials. This clearly demonstrates that OLED devices fabricated using the organic compounds provided in the examples of this application not only significantly improve luminous efficiency and significantly extend service life, but also maintain a low driving voltage, demonstrating excellent overall device performance.

[0297] In the description of this application, the terms "first" and "second" are used for descriptive purposes only and should not be understood to indicate or imply relative importance or implicitly specify the number of technical features indicated. Therefore, a feature defined as "first" or "second" may explicitly or implicitly include one or more features. In the description of this application, "plurality" means two or more, unless otherwise specifically defined.

[0298] In the above embodiments, the description of each embodiment has its own focus. For parts that are not described in detail in a certain embodiment, reference can be made to the relevant descriptions of other embodiments.

[0299] The embodiments, implementation methods and related technical features of the present application can be combined and replaced with each other without conflict.

[0300] The above are merely preferred embodiments of the present application and do not constitute any form of limitation to the present application. However, any simple modifications, equivalent changes, and modifications made to the above embodiments based on the technical essence of the present application without departing from the content of the technical solution of the present application are still within the scope of the technical solution of the present application.

Claims

1. An organic compound, characterized in that The general structural formula of the organic compound is shown in formula (1): wherein R is selected from a combination of one or more of a hydrogen atom, a deuterium atom, an alkyl group having 1 to 12 carbon atoms, and a cycloalkyl group having 3 to 12 carbon atoms; n is selected from any one of 0, 1, 2, 3, 4 and 5; L is selected from a single bond, a substituted or unsubstituted aromatic group having 5 to 25 ring atoms, and a substituted or unsubstituted heteroaromatic group having 5 to 25 ring atoms; Ar is selected from a combination of one or more substituted or unsubstituted aromatic groups having 5 to 25 ring atoms, and substituted or unsubstituted heteroaromatic groups having 5 to 25 ring atoms; The substituent group of the substituted or unsubstituted group is selected from a combination of one or more of a deuterium atom, an aromatic group having 5 to 25 ring atoms, and a heteroaromatic group having 5 to 25 ring atoms; The heteroatom in the heteroaromatic group is selected from one or more of a nitrogen atom, an oxygen atom or a sulfur atom.

2. The organic compound according to claim 1, characterized in that R is selected from a hydrogen atom, a deuterium atom or any one of the following groups: Wherein, "*" represents the connection site.

3. The organic compound according to claim 1, characterized in that L is selected from a single bond or any one or more combinations of the following groups: Wherein, "*" represents the connection site.

4. The organic compound according to claim 1, characterized in that Ar is selected from any one of the following substituted or unsubstituted groups: Among them, "*" represents the connection site; The substituent group in the substituted or unsubstituted group is selected from one or more combinations of deuterium atoms, phenyl groups, naphthyl groups, biphenyl groups, fluorenyl groups, dibenzofuranyl groups, dibenzothienyl groups and carbazolyl groups.

5. The organic compound according to any one of claims 1 to 4, characterized in that The organic compound is selected from any one of the compounds represented by formula (2-1) to formula (2-3):

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

7. A mixture, characterized in that The method comprises at least one organic compound according to any one of claims 1 to 6 and at least one organic functional material, wherein the organic functional material is selected from at least one of a hole injection material, a hole transport material, a luminescence auxiliary material, an electron transport material, an electron injection material, an electron blocking material, a hole blocking material, an organic luminescent guest material and an organic host material.

8. An organic light-emitting device, characterized in that: The organic light emitting device comprises: a first electrode; an organic functional layer, disposed on one side of the first electrode; a second electrode, disposed on a side of the organic functional layer away from the first electrode; The material of the organic functional layer includes at least one organic compound according to any one of claims 1 to 6, or the material of the organic functional layer includes the mixture according to claim 7.

9. The organic light-emitting device according to claim 8, characterized in that: The organic functional layer includes a light-emitting auxiliary layer and a light-emitting layer that are stacked, and the material of the light-emitting auxiliary layer includes at least one of the organic compounds.

10. A display panel, characterized in that: The organic light-emitting device according to claim 8 or 9.

Images