Organic compound, application thereof and organic electroluminescent device

By designing organic compounds with specific structures and using oxa or thia aromatic fused heterocycles and bridging connections with triazine structures, the problem of insufficient performance of existing OLED devices has been solved, and higher luminous efficiency and better performance have been achieved. Low voltage and energy consumption.

CN119330944APending Publication Date: 2025-01-21BEIJING DINGCAI TECHNOLOGY CO LTD
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Patent Information

Application Number
CN202310894671.6
Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Filing Date
2023-07-20
Publication Date
2025-01-21

AI Technical Summary

Technical Problem

The luminous efficiency, life and energy consumption of existing OLED devices have not yet met the needs of meeting the high-quality display effects, and it is urgent to develop higher-performance organic materials for organic electroluminescent devices.

Method used

Provide an organic compound with a specific structure, which is connected through the bridge connection between the aromatic fused heterocyclic ring of oxa or thia and the triazine structure to form a molecule with excellent photoelectric properties and electron transport properties, which is suitable as the main body of the light-emitting layer Material.

Benefits of technology

The organic compound significantly improves the luminous efficiency of organic electroluminescent devices, reduces voltage and energy consumption, and improves the arrangement of molecules in the light-emitting layer and the energy transfer effect.

✦ Generated by Eureka AI based on patent content.

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Abstract

The invention provides an organic compound and an application thereof, and an organic electroluminescent device, the organic compound has a structure as shown in formula I. Through the design of a molecular structure, the organic compound has a specific spatial configuration, a planar stacking structure is significantly improved, the axial property of molecules is increased, electron transport is promoted, and meanwhile, the organic electroluminescent device has a good application prospect. And the energy transfer and light extraction effects are improved. The organic compound has excellent photoelectric properties and electron transmission performance, is used for the organic electroluminescent device, is suitable for being used as a host material of a luminescent layer, can improve the arrangement of molecules in a host and a guest of the luminescent layer, and has a better energy transfer effect and a better light extraction effect, so that the luminous efficiency of the device is effectively improved, and the application prospect is broad. And voltage and energy consumption are reduced.
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Description

Technical Field

[0001] The invention belongs to the technical field of organic electroluminescent materials, and in particular relates to an organic compound and application thereof, and an organic electroluminescent device. Background Art

[0002] In recent years, optoelectronic devices based on organic materials have developed rapidly and become a research hotspot in the field. Examples of organic optoelectronic devices include organic light-emitting diodes (OLEDs), organic field-effect transistors, organic photovoltaic cells, organic sensors, etc. Among them, OLEDs have developed particularly rapidly and have achieved commercial success in the field of information display. OLEDs can provide highly saturated red, green, and blue colors. Full-color display devices made of OLEDs do not require additional backlight sources and have the advantages of brilliant colors, lightness, thinness, and softness.

[0003] The core of OLED devices is a multi-layer thin film structure containing a variety of functionalized organic materials. Common functionalized organic materials include: hole injection materials, hole transport materials, hole blocking materials, electron injection materials, electron transport materials, electron blocking materials, luminescent host materials and luminescent guest materials (also known as "dyes" and "doping materials"), etc. When electricity is turned on, electrons and holes are injected and transported to the luminescent area respectively and recombine there, thereby generating excitons and emitting light.

[0004] According to the luminescence mechanism, the current OLED can be divided into fluorescent luminescence, phosphorescent luminescence, thermally excited delayed fluorescence and thermally excited sensitized fluorescence. Common fluorescent luminescent bodies mainly use singlet excitons generated when electrons and holes combine to emit light, and are still widely used in various OLED products. Some metal complexes (such as iridium complexes and platinum complexes) can simultaneously use triplet excitons and singlet excitons for luminescence, and are called phosphorescent luminescent bodies. Their energy conversion efficiency can be increased by up to four times that of traditional fluorescent luminescent bodies. Thermally excited delayed fluorescence (TADF) promotes the transformation of triplet excitons to singlet excitons. Without the use of metal complexes, triplet excitons can still be effectively utilized to achieve higher luminescence efficiency. Thermally excited sensitized fluorescence (TASF) technology uses materials with TADF properties to sensitize the luminescent body through energy transfer, which can also achieve higher luminescence efficiency.

[0005] Although products using OLED technology have been commercialized, the device's lifespan, efficiency and other performance still need to be continuously improved to meet people's pursuit of high-quality display effects. Therefore, the field is in urgent need of developing more types of higher-performance organic materials, which can be applied to organic electroluminescent devices to make the devices have better luminous effects. Summary of the invention

[0006] In view of the deficiencies in the prior art, the purpose of the present invention is to provide an organic compound and its application, and an organic electroluminescent device. The organic compound has excellent photoelectric properties and is applied to organic electroluminescent devices, and is particularly suitable as a main material for the light-emitting layer, which can effectively improve the luminous efficiency of the device and reduce voltage and energy consumption.

[0007] In order to achieve the purpose of the invention, the present invention adopts the following technical solutions:

[0008] In a first aspect, the present invention provides an organic compound having a structure as shown in Formula I:

[0009]

[0010] In formula I, X is S or O.

[0011] In Formula I, Y1, Y2, Y3, Y4, Y5, Y6, Y7, and Y8 are each independently selected from CR 1 , CR A or N, multiple (e.g. 2, 3, 4, 5, 6, 7) CR 1 R 1 are the same or different groups.

[0012] At least one of Y1, Y2, Y3, Y4, Y5, Y6, Y7 and Y8 is CR A .

[0013] In Formula I, X1, X2, X3, and X4 are each independently selected from CR 2 or N; multiple (e.g. 2, 3, 4) CR 2 R 2 are the same or different groups.

[0014] R 1 , R 2 Each is independently selected from any one of hydrogen, halogen, unsubstituted or R'-substituted C1-C20 straight or branched alkyl, unsubstituted or R'-substituted C3-C20 cycloalkyl, unsubstituted or R'-substituted C2-C20 alkenyl, unsubstituted or R'-substituted C1-C20 alkoxy, unsubstituted or R'-substituted C1-C20 alkylsilyl, unsubstituted or R'-substituted C1-C20 alkylamino, cyano, nitro, hydroxyl, amino, unsubstituted or R'-substituted C6-C30 arylamino, unsubstituted or R'-substituted C3-C30 heteroarylamino, unsubstituted or R'-substituted C6-C30 aryloxy, unsubstituted or R'-substituted C3-C30 heteroaryloxy, unsubstituted or R'-substituted C6-C60 aryl, and unsubstituted or R'-substituted C3-C60 heteroaryl.

[0015] R A It has the structure shown in formula a:

[0016]

[0017] In formula a, -* represents the attachment site of the group;

[0018] In formula a, L1 is selected from any one of substituted or unsubstituted C6-C60 arylene groups.

[0019] In formula a, Ar1 and Ar2 are each independently selected from any one of a substituted or unsubstituted C6-C60 aryl group and a substituted or unsubstituted C3-C60 heteroaryl group.

[0020] The substituents substituted in L1, Ar1, Ar2, and R' are each independently selected from any one of halogen, cyano, nitro, hydroxyl, amino, C1-C20 straight or branched alkyl, C3-C20 cycloalkyl, C2-C20 alkenyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl, or a combination of at least two thereof.

[0021] In the present invention, the "substituted or unsubstituted" group may be substituted with one substituent or with multiple substituents. When there are multiple substituents (at least 2), they may be the same or different substituents. When the same expressions are mentioned below, they have the same meaning. Unless otherwise specified, the selection ranges of the substituted substituents and R' are as shown above and will not be repeated.

[0022] The substituted substituents in L1, Ar1 and Ar2 are each independently not connected to the adjacent ring structure or are connected to form a ring through a chemical bond; the R' is each independently not connected to the adjacent ring structure or is connected to form a ring through a chemical bond.

[0023] In the present invention, "R' is independently not connected to the adjacent ring structure" means that R' is only connected to the C atom through a single bond; "R' is independently connected to the adjacent ring structure through a chemical bond to form a ring" means that R' is connected to the adjacent ring through a chemical bond in addition to the C atom through a chemical bond, thereby forming a fused ring structure. When the same description is involved below, it has the same meaning and will not be repeated one by one.

[0024] The organic compound provided by the present invention has a structure shown in formula I, which uses an aromatic condensed heterocycle of oxygen or sulfur (X is S or O) as a parent core, and a triazine structure shown in formula a is connected to a specific site of the aromatic condensed heterocycle parent core, and the triazine structure is connected to the parent core through a bridging group L1, so that the organic compound has a specific spatial configuration, significantly improves the planar stacking structure, and increases the axiality of the molecule, while promoting electron transmission, improving energy transfer and light extraction effect. The organic compound has excellent photoelectric properties and electron transmission performance, and is used for organic electroluminescent devices, suitable as a main material of the light-emitting layer, and has good electron transmission performance, which can improve the arrangement of the molecule in the light-emitting layer host and guest, and has better energy transfer effect and better light extraction effect, thereby effectively improving the luminous efficiency of the device, reducing voltage and energy consumption.

[0025] It should be noted that, in order to facilitate explanation, the possible effects of each group / feature are described separately in the present invention, but this does not mean that these groups / features act in isolation. In fact, the essential reason for obtaining good performance is the optimized combination of the entire molecular structure, which is the result of the synergistic effect of each group, rather than the effect of a single group / feature.

[0026] The following are preferred technical solutions of the present invention, but are not intended to limit the technical solutions provided by the present invention. Through the following preferred technical solutions, the objectives and beneficial effects of the present invention can be better achieved and realized.

[0027] In the present invention, the halogen may be fluorine, chlorine, bromine or iodine. The following descriptions involving the same have the same meaning.

[0028] In the present invention, the expression of chemical elements, unless otherwise specified, includes the concept of isotopes with the same chemical properties. For example, hydrogen (H) includes 1 H (hydrogen), 2 H (deuterium, D), 3 H (tritium, T), etc.; carbon (C) includes 12 C. 13 C, etc.

[0029] In the present invention, unless otherwise specified, the heteroatom of the heteroaryl group is selected from N, O, S, P, B, Si or Se, preferably N, O or S.

[0030] In the present invention, the expression of a ring structure crossed by “—” indicates that the connection site is any position on the ring structure that can form a bond.

[0031] In the present invention, "-*" and "*" both represent the bonding site of a group.

[0032] In the present invention, the expression of Ca-Cb means that the number of carbon atoms in the group is ab. Unless otherwise specified, the number of carbon atoms does not include the number of carbon atoms in the substituent.

[0033] In the present invention, “each independently” means that when there are multiple subjects, they may be the same as or different from each other.

[0034] In the present invention, C1-C20 may be C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.

[0035] The C3-C20 can all be C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.

[0036] The C2-C20 can all be C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.

[0037] The C6-C30 can all be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0038] The C3-C30 can all be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0039] The C6-C60 can all be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56 or C58, etc.

[0040] The C3-C60 can all be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56 or C58, etc.

[0041] In the present invention, the C1-C20 straight chain or branched alkyl group, preferably a C1-C16 straight chain or branched alkyl group, and further preferably a C1-C10 straight chain or branched alkyl group, illustratively includes but is not limited to: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, 2-methylbutyl, n-pentyl, isopentyl, neopentyl, n-hexyl, neohexyl, 2-ethylhexyl, n-octyl, n-heptyl, n-nonyl, n-decyl, etc.

[0042] Specific examples of the C1-C20 alkoxy group include monovalent groups obtained by connecting the above-mentioned linear or branched alkyl groups to O.

[0043] A specific example of the C1-C20 alkylsilyl group is a monovalent group in which at least one hydrogen in -SiH3 is replaced by the above-mentioned straight-chain or branched alkyl group; a specific example of the C1-C20 alkylamino group is a monovalent group in which at least one hydrogen in -NH2 is replaced by the above-mentioned straight-chain or branched alkyl group.

[0044] The C3-C20 cycloalkyl, preferably C3-C10 cycloalkyl, includes monocycloalkyl or polycycloalkyl. Monocycloalkyl refers to an alkyl group containing a single cyclic structure, and polycycloalkyl refers to a structure composed of two or more cycloalkyl groups sharing one or more carbon atoms on the ring; exemplary examples include but are not limited to: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, etc.

[0045] The C2-C20 alkenyl, preferably C2-C10 alkenyl, contains at least one C=C, illustratively including but not limited to: vinyl, propenyl, allyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, butadienyl, pentadienyl and the like.

[0046] The C6-C60 aryl group, preferably a C6-C30 aryl group, and more preferably a C6-C20 aryl group, includes a monocyclic aryl group and a condensed aryl group; the monocyclic aryl group means that the group contains at least one phenyl group, and when it contains at least two phenyl groups, the phenyl groups are connected by a single bond, and exemplary examples include but are not limited to: phenyl, biphenyl, terphenyl, quaterphenyl, etc.; the condensed aryl group means that the group contains at least two aromatic rings, and the aromatic rings share two adjacent aromatic rings. The carbon atoms of the groups are mutually fused, including, but not limited to, naphthyl, anthracenyl, phenanthrenyl, indenyl, fluorenyl and its derivatives (9,9-dimethylfluorenyl, 9,9-diethylfluorenyl, 9,9-dipropylfluorenyl, 9,9-dibutylfluorenyl, 9,9-dipentylfluorenyl, 9,9-dihexylfluorenyl, 9,9-diphenylfluorenyl, 9,9-dinaphthylfluorenyl, spirobifluorenyl, benzofluorenyl, etc.), fluoranthenyl, triphenylene, pyrenyl, perylene, It should be noted that the monocyclic aromatic groups and condensed aromatic groups connected by a single bond also belong to the scope of aromatic groups, such as phenylnaphthyl, naphthylphenyl, naphthylnaphthyl, phenylnaphthylphenyl, etc.

[0047] The C3-C60 heteroaryl, preferably C6-C30 heteroaryl, further preferably C3-C20 heteroaryl, includes a monocyclic heteroaryl or a condensed ring heteroaryl. The monocyclic heteroaryl means that the molecule contains at least one heteroaryl. When the molecule contains a heteroaryl and other groups (such as aryl, heteroaryl, etc.), the heteroaryl and other groups are connected by a single bond, exemplarily including but not limited to: pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thienyl, pyrrolyl, bipyridyl, phenylpyridyl, pyridylphenyl, etc. The fused ring heteroaryl group means a group containing at least one aromatic heterocycle and one aromatic ring (aromatic heterocycle or aromatic ring) in the molecule, and the two share two adjacent atoms that are fused to each other, including, but not limited to, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, isobenzothiophenyl, indolyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl and its derivatives (N-phenylcarbazolyl, N-naphthylcarbazolyl, benzocarbazolyl, dibenzocarbazolyl, indolcarbazolyl, azacarbazolyl, etc.), acridinyl, phenothiazinyl, phenoxazinyl, hydroacridinyl, etc. It should be noted that heteroaryl and heteroaryl groups connected by a single bond, and aryl and heteroaryl groups connected by a single bond also fall within the scope of heteroaryl groups, for example, dibenzofuranylphenyl, dibenzofuranylnaphthyl, dibenzothienylphenyl, dibenzothienylnaphthyl, and the like.

[0048] In the present invention, the C6-C30 aryloxy group is a monovalent group formed by connecting the above-mentioned aryl groups and O, and the C3-C30 heteroaryloxy group is a monovalent group formed by connecting the above-mentioned heteroaryl groups and O.

[0049] In the present invention, a specific example of the C6-C30 arylamino group is a monovalent group in which at least one hydrogen in -NH2 is replaced by the above aryl group, including but not limited to phenylamino, methylphenylamino, naphthylamino, anthracenylamino, phenanthrenylamino, biphenylamino, etc. A specific example of the C3-C30 heteroarylamino group is a monovalent group in which at least one hydrogen in -NH2 is replaced by the above heteroaryl group, including but not limited to pyridylamino, pyrimidinylamino, dibenzofuranylamino, etc.

[0050] Preferably, at most 3 (e.g. 0, 1, 2 or 3) of Y1, Y2, Y3, Y4, Y5, Y6, Y7 and Y8 are N.

[0051] Preferably, at most one (0 or 1) of Y1 and Y8 is N; and / or at most one (0 or 1) of Y2 and Y3 is N; and / or at most one (0 or 1) of Y4, Y5, Y6 and Y7 is N.

[0052] Preferably, Y1, Y2, Y3, Y4, Y5, Y6, Y7, and Y8 are each independently selected from CR 1 or CR A Any one of, and at least one of Y1, Y2, Y3, Y4, Y5, Y6, Y7 and Y8 is CR A .

[0053] Preferably, Y1, Y2, Y3, and Y8 are each independently selected from CR 1 , said Y4, Y5, Y6, Y7 are each independently selected from CR 1 or CR A Any one of, and at least one of Y4, Y5, Y6 and Y7 is CR A .

[0054] More preferably, said Y5 is CR A .

[0055] Preferably, Y1, Y2, Y3, and Y8 are each independently selected from CR 1 , said Y4, Y5, Y6, Y7 are each independently selected from CR 1 or CR A Any one of, and only one of Y4, Y5, Y6 and Y7 is CR A .

[0056] Preferably, the R 1 Each is independently selected from any one of hydrogen, unsubstituted or R'-substituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight or branched alkyl, unsubstituted or R'-substituted C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, cyano, unsubstituted or R'-substituted C6-C2 (e.g., C6, C9, C10, C12, C14, C15, C16, or C18, etc.) aryl, and unsubstituted or R'-substituted C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, or C18, etc.) heteroaryl, and is more preferably hydrogen.

[0057] Preferably, at most one (0 or 1) of X1, X2, X3 and X4 is N.

[0058] Preferably, X1, X2, X3, and X4 are each independently selected from CR2 .

[0059] Preferably, the R 2 Each is independently selected from any one of hydrogen, unsubstituted or R'-substituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight or branched alkyl, unsubstituted or R'-substituted C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, cyano, unsubstituted or R'-substituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl, and unsubstituted or R'-substituted C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16 or C18, etc.) heteroaryl, and is more preferably hydrogen.

[0060] Preferably, the organic compound has a structure as shown in Formula II:

[0061]

[0062] In Formula II, X, L1, Ar1, and Ar2 have the same defined ranges as those in Formula I.

[0063] Preferably, the organic compound has a structure as shown in Formula IIA or Formula IIB, and more preferably a structure as shown in Formula IIB:

[0064]

[0065] Preferably, L1 is selected from any one of substituted or unsubstituted C6-C20 (eg, C6, C9, C10, C12, C14, C15, C16 or C18, etc.) arylene groups.

[0066] Preferably, L1 is selected from any one of the following substituted or unsubstituted groups:

[0067] -* represents the attachment site of the group.

[0068] Preferably, the substituted substituent in L1 is selected from any one or a combination of at least two of halogen, cyano, C1-C20 straight or branched alkyl, C3-C20 cycloalkyl, C6-C30 aryl, and is further preferably any one or a combination of at least two of cyano, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight or branched alkyl, C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, etc.) aryl, and is further preferably any one of methyl, isopropyl or tert-butyl.

[0069] Preferably, L is selected from any one of the following groups:

[0070] Wherein, -* represents the attachment site of the group.

[0071] Preferably, L is selected from any one of the following groups:

[0072] In a preferred technical solution, the L is selected from any one of the following substituted or unsubstituted groups: Best Further optimization Any one of the following; -* represents the attachment site of the group.

[0073] Preferably, Ar1 and Ar2 are each independently selected from any one of substituted or unsubstituted C6-C30 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C25, C28, etc.) aryl groups and substituted or unsubstituted C3-C30 (e.g., C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C25, C28, etc.) heteroaryl groups.

[0074] Preferably, Ar1 and Ar2 are each independently selected from any one of the following substituted or unsubstituted groups: -* represents the attachment site of the group.

[0075] Wherein, Z is selected from O, S, CR 11 R 12 or NR 13 Any one of .

[0076] R 11 , R 12 , R 13 Each is independently selected from any one or a combination of at least two of a C1-C20 straight or branched alkyl group, a C3-C20 cycloalkyl group, a C2-C20 alkenyl group, a C6-C30 aryl group, and a C3-C30 heteroaryl group; 11 and R 12 Not connected or connected to form a ring through chemical bonds.

[0077] Preferably, Z is selected from O, S or CR 11 R 12 Any one of .

[0078] Preferably, the R 11 , R 12 Each is independently selected from any one of C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight chain or branched alkyl, C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl, further preferably any one of C1-C6 straight chain or branched alkyl, phenyl, naphthyl, biphenyl, further preferably methyl or phenyl.

[0079] Preferably, the substituents substituted in Ar1 and Ar2 are each independently selected from halogen, cyano, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight or branched alkyl, C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl, C3-C20 (for example, C3, C4, C5, C6, C9, C10, C12, C14, C15, C16 or C18, etc.) heteroaryl, or a combination of at least two thereof, and any one of cyano, methyl, tert-butyl, isopropyl, cyclohexanyl, phenyl, biphenyl, terphenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, fluorenyl and dimethylfluorenyl is further preferred.

[0080] Preferably, Ar1 and Ar2 are each independently selected from any one of the following groups:

[0081]

[0082] -* represents the attachment site of the group.

[0083] Preferably, Ar1 and Ar2 are each independently selected from any one of the following groups:

[0084]

[0085] Preferably, the organic compound has a structure shown in any one of the following N1-N176, S1-S176:

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114] In a second aspect, the present invention provides a use of the organic compound as described in the first aspect, wherein the organic compound is applied to an organic electronic device.

[0115] Preferably, the organic electronic device includes an organic electroluminescent device, an optical sensor, a solar cell, a lighting element, an organic thin film transistor, an organic field effect transistor, an organic thin film solar cell, an information tag, an electronic artificial skin sheet, a sheet-type scanner or electronic paper.

[0116] Preferably, the organic compound is applied to an organic electroluminescent device.

[0117] Preferably, the organic compound is used as a light-emitting layer material in an organic electroluminescent device, and more preferably as a host material of the light-emitting layer.

[0118] In a third aspect, the present invention provides an organic electroluminescent device, comprising a first electrode, a second electrode and at least one organic layer disposed between the first electrode and the second electrode; the organic layer comprises at least one organic compound as described in the first aspect.

[0119] Preferably, the organic layer includes at least one organic compound having the structure shown by N1-N176, S1-S176.

[0120] Preferably, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises at least one organic compound as described in the first aspect.

[0121] Preferably, the light-emitting layer comprises a host material and a doping material, and the host material comprises at least one organic compound as described in the first aspect.

[0122] As a preferred technical solution of the present invention, the organic compound is used as the main material of the light-emitting layer, which is an electronic main material with a low triplet energy difference, and is particularly suitable as the main material of the red light-emitting layer, and can improve the luminous efficiency and service life of the organic electroluminescent device.

[0123] Preferably, the host material comprises a combination of a first host material and a second host material, and the first host material comprises at least one organic compound as described in the first aspect.

[0124] Preferably, the second host material comprises a compound having a structure as shown in Formula III:

[0125]

[0126] In formula III, Ar3, Ar4, and Ar5 are each independently selected from any one of a substituted or unsubstituted C6-C60 aryl group and a substituted or unsubstituted C3-C60 heteroaryl group; Ar3, Ar4, and Ar5 are not connected or are connected to form a ring through chemical bonds.

[0127] The substituted substituents in Ar3, Ar4 and Ar5 are each independently selected from any one of halogen, C1-C20 straight or branched alkyl, C2-C10 alkenyl, C3-C20 cycloalkyl, C2-C20 heterocycloalkyl, C1-C10 alkoxy, carboxyl, nitro, cyano, amino, hydroxyl, mercapto, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl and C3-C60 heteroaryl; the substituted substituents are each independently not connected to the adjacent ring structure or are connected to form a ring by chemical bonds.

[0128] Preferably, the organic compound is used as the first host material in a dual-host device, which has excellent electron transport properties. When compounded with the second host material of the structure shown in Formula III, it can effectively regulate and achieve the transmission balance of holes and electrons, further improve the luminescence effect of the device, enhance efficiency and life, reduce driving voltage and energy consumption, and improve the overall performance of the device.

[0129] Preferably, the mass ratio of the first host material to the second host material is (0.1-2):1, for example, it can be 0.2:1, 0.3:1, 0.4:1, 0.5:1, 0.6:1, 0.7:1, 0.8:1, 0.9:1, 1:1, 1.1:1, 1.2:1, 1.3:1, 1.4:1, 1.5:1, 1.6:1, 1.7:1, 1.8:1 or 1.9:1, and further preferably (0.5-1.5):1.

[0130] Preferably, the doping material (also called “dopant”, “dye”, “luminescent dye”, “guest material”) is a phosphorescent doping material.

[0131] Preferably, based on the mass of the main material being 100%, the mass of the doping material in the light-emitting layer is 0.1-10%, for example, 0.5%, 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8% or 9%.

[0132] Preferably, the organic layer further includes a hole transport region and an electron transport region.

[0133] Preferably, the hole transport region includes any one of a hole injection layer, a hole transport layer, and an electron blocking layer, or a combination of at least two of them.

[0134] Preferably, the electron transport region includes any one of an electron injection layer, an electron transport layer, and a hole blocking layer, or a combination of at least two of them.

[0135] In a preferred technical solution, the organic electroluminescent device (OLED device) includes a first electrode and a second electrode, and an organic layer located between the electrodes. The organic layer can be divided into multiple regions, for example, including a hole transport region, a light-emitting layer, and an electron transport region; the light-emitting layer includes at least one organic compound as described in the first aspect, and further preferably includes at least one organic compound having a structure shown in N1-N176 or S1-S176.

[0136] In a preferred technical solution, the organic electroluminescent device includes a first electrode, a plurality of light-emitting functional layers (organic layers) and a second electrode arranged in sequence; the organic layer includes a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer and an electron injection layer arranged in sequence, and the hole injection layer is in contact with the first electrode (anode). The organic layer (preferably the light-emitting layer) contains at least one organic compound as described in the first aspect, and further preferably contains at least one organic compound having a structure shown in N1-N176 or S1-S176.

[0137] In a preferred technical solution, a substrate can be used below the first electrode or above the second electrode. The substrate is glass or polymer material with excellent mechanical strength, thermal stability, water resistance and transparency. In addition, a thin film transistor (TFT) can also be provided on the substrate used as a display.

[0138] The first electrode can be formed by sputtering or depositing the material used as the first electrode on the substrate. When the first electrode is used as an anode, an oxide transparent conductive material such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), zinc oxide (ZnO) and any combination thereof can be used. When the first electrode is used as a cathode, a metal or alloy such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), ytterbium (Yb), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag) and any combination thereof can be used.

[0139] The organic layer can be formed on the electrode by vacuum thermal evaporation, spin coating, printing, etc. The compound used as the organic layer can be an organic small molecule, an organic macromolecule or a polymer, and a combination thereof.

[0140] The hole transport region is located between the anode and the light-emitting layer. The hole transport region can be a single-layer hole transport layer (HTL), including a single-layer hole transport layer containing only one compound and a single-layer hole transport layer containing multiple compounds. The hole transport region can also be a multilayer structure including at least one layer of a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL); wherein the HIL is located between the anode and the HTL, and the EBL is located between the HTL and the light-emitting layer.

[0141] The material of the hole transport region can be selected from, but not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylene ethylene, polyaniline / dodecylbenzenesulfonic acid (Pani / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (Pani / CSA), polyaniline / poly(4-styrenesulfonate) (Pani / PSS), aromatic amine derivatives, wherein the aromatic amine derivatives include the compounds shown in HT-1 to HT-51 below; or any combination thereof.

[0142]

[0143]

[0144]

[0145]

[0146] The hole injection layer is located between the anode and the hole transport layer. The hole injection layer can be a single compound material or a combination of multiple compounds. For example, the hole injection layer can use one or more compounds of HT-1 to HT-51 above, or one or more compounds of HI-1 to HI-3 below; or one or more compounds of HT-1 to HT-51 can be doped with one or more compounds of HI-1 to HI-3 below.

[0147]

[0148] The light-emitting layer includes a light-emitting dye (i.e., dopant) that can emit different wavelength spectra and a host material (Host). The light-emitting layer can be a monochrome light-emitting layer that emits a single color such as red, green, and blue. A plurality of monochrome light-emitting layers of different colors can be arranged in a plane according to a pixel pattern, or they can be stacked together to form a color light-emitting layer. When light-emitting layers of different colors are stacked together, they can be separated from each other or connected to each other. The light-emitting layer can also be a single color light-emitting layer that can simultaneously emit different colors such as red, green, and blue.

[0149] According to different technologies, the light-emitting layer material can be made of different materials such as fluorescent electroluminescent materials, phosphorescent electroluminescent materials, and thermally activated delayed fluorescent materials. In an OLED device, a single light-emitting technology can be used, or a combination of multiple different light-emitting technologies can be used. These different light-emitting materials classified by technology can emit light of the same color or different colors.

[0150] In the preferred technical solution of the present invention, the light-emitting layer adopts phosphorescent electroluminescence technology. The main material of the light-emitting layer includes a combination of a first main material and a second main material, wherein the first main material includes at least one organic compound described in Formula I.

[0151] The second main body material includes Specifically, the second host material can be selected from, but not limited to, one or more combinations of the following specific compounds H1-H28.

[0152]

[0153]

[0154]

[0155] In one aspect of the present invention, the light-emitting layer adopts phosphorescent electroluminescence technology. The phosphorescent dopant of the light-emitting layer can be selected from, but not limited to, one or more combinations of RPD-1 to RPD-28 listed below.

[0156]

[0157]

[0158] In one aspect of the present invention, an electron blocking layer (EBL) is located between the hole transport layer and the light emitting layer. The electron blocking layer may be one or more compounds of HT-1 to HT-51, but is not limited thereto.

[0159] The OLED organic layer may further include an electron transport region between the light emitting layer and the cathode. The electron transport region may be a single-layer electron transport layer (ETL), including a single-layer electron transport layer containing only one compound and a single-layer electron transport layer containing multiple compounds. The electron transport region may also be a multi-layer structure including at least one layer of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0160] In one aspect of the present invention, the electron transport layer material can be selected from, but not limited to, one or more combinations of ET-1 to ET-73 listed below.

[0161]

[0162]

[0163]

[0164]

[0165] In one aspect of the present invention, a hole blocking layer (HBL) is located between the electron transport layer and the light emitting layer. The hole blocking layer may be one or more compounds of the above ET-1 to ET-73, but is not limited thereto.

[0166] The device may also include an electron injection layer located between the electron transport layer and the cathode. The electron injection layer material includes but is not limited to one or more combinations of the following: LiQ, LiF, NaCl, CsF, Li2O, Cs2CO3, BaO, Na, Li, Ca, Mg, and Yb.

[0167] In a fourth aspect, the present invention provides a display device, comprising the organic electroluminescent device as described in the third aspect.

[0168] Preferably, the display device includes a display screen or a display panel.

[0169] The present invention also provides an electronic device, which includes the above-mentioned display device.

[0170] Compared with the prior art, the present invention has the following beneficial effects:

[0171] The organic compound provided by the present invention has a structure shown in Formula I, and through the design of the molecular structure, it has a specific spatial configuration, significantly improves the planar stacking structure, and increases the axiality of the molecule, while promoting electron transmission, improving energy transfer and light extraction effects. The organic compound has excellent photoelectric properties and electron transmission performance, and is used in organic electroluminescent devices, suitable as a main material of the light-emitting layer, and can improve the arrangement of the host and guest of the molecule in the light-emitting layer, and has better energy transfer effect and better light extraction effect, thereby effectively improving the luminous efficiency of the device and reducing voltage and energy consumption. BRIEF DESCRIPTION OF THE DRAWINGS

[0172] Figure 1 The X-ray diffraction pattern of the organic compound N145 provided by the present invention;

[0173] Figure 2 This is the X-ray diffraction pattern of the intermediate M1-3 obtained in Preparation Example 1. DETAILED DESCRIPTION

[0174] The technical solution of the present invention is further described below by specific implementation methods. It should be understood by those skilled in the art that the embodiments are only to help understand the present invention and should not be regarded as specific limitations of the present invention.

[0175] The organic compound represented by formula I of the present invention can be synthesized by organic synthesis methods known in the art. An exemplary synthesis route is given below, but those skilled in the art can also obtain it by other methods known in the art.

[0176] In a specific embodiment, the organic compound can be prepared by the following synthetic route:

[0177] Wherein, X, X1, X2, X3, X4, Y1, Y8, L1, Ar1, Ar2 have the same definitions as in Formula I and Formula A; Y4, Y5, Y6, Y7 are each independently selected from CR 1 , CR B or N, and one of them is CR B , R B is Cl; U is selected from Hal1 is selected from halogen, preferably Cl, Br or I.

[0178] In intermediate A3, one of Y4, Y5, Y6, and Y7 is CR B , which is converted into Then a coupling reaction occurs with the raw material S to obtain the target product.

[0179] The specific preparation method of the organic compound of the present invention will be described in detail below using multiple preparation examples and synthesis examples as examples. However, the preparation method of the organic compound of the structure shown in Formula I of the present invention includes but is not limited to the synthesis method in the specific implementation method. Those skilled in the art can also make routine adjustments to the preparation method according to actual needs. The organic compound of the structure shown in Formula I synthesized by other methods also belongs to the protection scope of the present invention.

[0180] The following preparation examples and synthesis examples of the present invention provide specific synthesis methods of representative compounds by way of example. The solvents and reagents used in the synthesis examples can all be purchased or customized from the chemical product market. The mass spectrometry characterization data (MS) of the intermediates and target compounds in the present invention are obtained by mass spectrometer testing; the reaction process and endpoint are detected by gas thin layer chromatography (TLC).

[0181] The compounds of the synthesis methods not mentioned in the present invention are all raw materials obtained from commercial channels, or are prepared by themselves according to known methods using these raw materials.

[0182] Preparation Example 1: Synthesis of Intermediate M1

[0183]

[0184] Dibenzofuran-2-boric acid (0.8 mol), 2-bromo-5-chloro-benzaldehyde (0.8 mol), potassium carbonate (1 mol), tetrakis(triphenylphosphine)palladium (0.01 mol), water (300 mL) and dioxane (1500 mL) were added to a reaction bottle, heated to 90°C for 6 h, and the reaction was complete under TLC monitoring. Water and dichloromethane were added for extraction, and the organic phase was separated and concentrated to obtain intermediate M1-1.

[0185] Add intermediate M1-1 (0.7 mol), (methoxymethyl) triphenylphosphonium chloride (0.8 mol), and tetrahydrofuran (2000 mL) to the reaction flask, cool to 0°C while stirring, and gradually add sodium tert-butoxide (1 mol) in batches. The temperature during the addition process is not higher than 5°C. After the addition is completed, react at room temperature for 2 hours. TLC monitors the reaction to be complete. Add brine and ethyl acetate for extraction, and concentrate the organic phase to obtain intermediate M1-2.

[0186] The intermediate M1-2 (0.5 mol) was added to dichloromethane (1500 mL), cooled to -20°C with stirring, and methanesulfonic acid (1 mol) was slowly added dropwise. After the addition was complete, the reaction was kept warm for 1 h. The reaction was monitored to be complete by TLC. After the solvent was directly concentrated, the content of M1-3 was 85% and the content of M1-3-1 was 15% by high performance liquid chromatography (HPLC). The intermediate M1-3 was recrystallized from toluene / ethanol with a purity greater than 99.5%.

[0187] The intermediate M1-3 was detected by X-ray diffractometer (XRD, model Synergy-R, manufacturer Rigaku), and the obtained X-ray diffraction pattern is as follows: Figure 2 As shown, single crystal diffraction detection shows that the structure of the prepared intermediate M1-3 is correct.

[0188] The intermediate M1-3 (0.3 mol), pinacol borate (0.4 mol), potassium acetate (0.5 mol), 1,1-bis(diphenylphosphino)ferrocenepalladium dichloride (0.005 mol) and dioxane (1500 mL) were added to a reaction bottle, heated to 90°C for 6 h, and the reaction was complete under TLC monitoring. Water and dichloromethane were added for extraction, and the organic phase was separated and concentrated to obtain the intermediate M1 (MS: 395.2).

[0189] Preparation Example 2-4: Synthesis of Intermediates M2, M3, and M4

[0190] The synthesis method of intermediates M2, M3, and M4 is similar to that of intermediate M1, except that the 2-bromo-5-chloro-benzaldehyde in Preparation Example 1 is replaced by equimolar amounts of 2-bromo-3-chloro-benzaldehyde, 2-bromo-4-chloro-benzaldehyde, and 2-bromo-6-chloro-benzaldehyde, respectively, and the other materials, synthesis steps, and parameters are the same as those in Preparation Example 1 to obtain intermediates M2, M3, and M4 as shown below.

[0191]

[0192] Preparation Example 5-8: Synthesis of Intermediates M5, M6, M7, and M8

[0193] The synthesis method of intermediate M5 is similar to that of intermediate M1, except that the dibenzofuran-2-boric acid in Preparation Example 1 is replaced by an equimolar amount of dibenzothiophene-2-boric acid, and the other materials, synthesis steps and parameters are the same as those in Preparation Example 1, to obtain intermediate M5 as shown below. The synthesis method of intermediates M6, M7 and M8 is similar to that of intermediate M1, except that the dibenzofuran-2-boric acid in Preparation Example 1 is replaced by an equimolar amount of dibenzothiophene-2-boric acid, and 2-bromo-5-chloro-benzaldehyde is replaced by an equimolar amount of 2-bromo-3-chloro-benzaldehyde, 2-bromo-4-chloro-benzaldehyde and 2-bromo-6-chloro-benzaldehyde, respectively, and the other materials, synthesis steps and parameters are the same as those in Preparation Example 1, to obtain intermediates M6, M7 and M8 as shown below.

[0194]

[0195] Synthesis Example 1: Synthesis of organic compound N145

[0196]

[0197] The intermediate M1 (0.02 mol), raw material S1 (0.02 mol), potassium carbonate (0.024 mol), tri(dibenzylideneacetone)dipalladium (0.0002 mol), 2-dicyclohexylphosphine-2',6'-dimethoxy-biphenyl (0.0004 mol), water (20 mL) and dioxane (200 mL) were added to a reaction bottle, heated to 100°C for 7 h, and the reaction was complete under TLC monitoring. After cooling, a large amount of solid precipitated. After filtration, the target product N145 (MS, 626.2) was obtained by recrystallization from xylene.

[0198] In order to further determine the structural accuracy of the compound, an X-ray diffractometer was used to detect the prepared target product. The X-ray diffraction pattern of the organic compound N145 is shown in Figure 1 As shown, it indicates that the structure of the prepared target product is correct.

[0199] Synthesis Example 2: Synthesis of organic compound N73

[0200] The synthesis method of N73 is similar to that of N145, except that the intermediate M1 in Synthesis Example 1 is replaced by an equimolar amount of intermediate M3, and the other materials, synthesis steps and parameters are the same as those in Synthesis Example 1 to obtain the target product N73 (MS, 626.2).

[0201] Synthesis Example 3-7: The synthesis method is similar to that of N145, except that the intermediate M1 and / or triazine raw material S1 in Synthesis Example 1 are replaced with the raw materials shown in Table 1, and other materials, synthesis steps and parameters are the same as those in Synthesis Example 1 to obtain the target product.

[0202] Table 1

[0203]

[0204]

[0205] Other compounds in the present invention can be synthesized by the above Suzuki method, except that different intermediates (any one of M1-M8) and / or triazine raw materials are replaced, which are not listed one by one.

[0206] The present invention illustratively provides a specific synthesis method for all intermediates (M1-M8), as well as an example of synthesizing the compounds of the present invention by Suzuki reaction of some intermediates with triazine raw materials. For other compounds for which no specific synthesis method is given, they are also prepared by similar methods, and only need to replace the raw materials to obtain them. They will not be described in detail here, or those skilled in the art can also prepare them by other methods in the prior art.

[0207] Example 1

[0208] An organic electroluminescent device comprises an anode (ITO), a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer and a cathode (Al) arranged in sequence. The preparation method of the organic electroluminescent device is as follows:

[0209] (1) a glass substrate coated with an ITO transparent conductive layer was ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in an acetone / ethanol mixed solvent, baked in a clean environment until the water was completely removed, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam;

[0210] (2) Place the glass substrate with the anode in a vacuum chamber and evacuate the chamber to a vacuum of less than 1×10 -5 Pa, vacuum evaporating a mixture of compound HT-29:HI-1 (97 / 3, w / w) on the above anode layer as a hole injection layer, the evaporation rate is 0.1 nm / s, and the evaporation film thickness is 10 nm;

[0211] (3) vacuum evaporating compound HT-29 on the hole injection layer as a hole transport layer, with an evaporation rate of 0.1 nm / s and a total evaporation film thickness of 60 nm;

[0212] (4) vacuum evaporating compound HT-37 on the hole transport layer as an electron blocking layer, with an evaporation rate of 0.1 nm / s and a total evaporation film thickness of 60 nm;

[0213] (5) vacuum evaporating a light-emitting layer on the electron blocking layer, wherein the light-emitting layer includes a main material and a doping material (dye, RPD-18), and the mass ratio (w / w) of the main material to the doping material is 100:3; the main material is a mixture of a first main material (the organic compound N5 provided by the present invention) and a second main material (compound H26) (the mass ratio of N1 to H26 is 1:1); the evaporation is carried out by a dual-source co-evaporation method, the evaporation rate is 0.1 nm / s, and the total evaporation film thickness is 40 nm;

[0214] (6) vacuum evaporating compound ET-17 on the light-emitting layer as a hole blocking layer, with an evaporation rate of 0.1 nm / s and a total evaporation film thickness of 5 nm;

[0215] (7) vacuum evaporating a mixture of compounds ET-66:ET-57 (50 / 50, w / w) on the hole blocking layer as an electron transport layer, with an evaporation rate of 0.1 nm / s and a total evaporation film thickness of 25 nm;

[0216] (8) Vacuum evaporation of LiF as an electron injection layer on the electron transport layer at a rate of 0.1 nm / s and a thickness of 1 nm;

[0217] (9) Vacuum evaporating metal Al with a thickness of 150 nm on the electron injection layer as a cathode at a evaporation rate of 1 nm / s to obtain the organic electroluminescent device.

[0218] Examples 2-29, Comparative Examples 1-4

[0219] An organic electroluminescent device, which differs from Example 1 only in that the main materials of the light-emitting layer are the compounds shown in Table 1, and the mass ratio of the first main material to the second main material is 1:1; other layers, thicknesses, materials and preparation methods are the same as those of device Example 1.

[0220] The structure of the main material in the comparative example is as follows:

[0221]

[0222] The performance test of the organic electroluminescent devices provided in Examples 1-29 and Comparative Examples 1-4 was performed in the following manner:

[0223] At the same brightness of 3000cd / m 2 Under the condition of 100 ℃ and 80 ℃, the current density and voltage of the organic electroluminescent device are measured using a digital source meter and a brightness meter. The ratio of brightness to current density is the current efficiency.

[0224] The test values ​​of voltage and current efficiency of comparative example 1 are recorded as 1, and the ratios of the test values ​​of voltage of other devices to the test values ​​of voltage and current efficiency of comparative example 1 (relative voltage, relative current efficiency) are calculated. The specific results are shown in Table 2.

[0225] Table 2

[0226]

[0227]

[0228] Combined with the data in Table 2, it can be seen that the organic compound provided by the present invention has excellent photoelectric properties and electron transport performance. As the main material of the light-emitting layer of the organic electroluminescent device, it can significantly improve the luminous efficiency of the device and reduce the voltage.

[0229] By comparing the light-emitting layer materials and effect data of Examples 1-29 with those of Comparative Examples 1-4, it can be seen that the devices using the organic compounds of the present invention are superior to the comparative compounds in terms of voltage and efficiency. The reasons for this are as follows: the present invention is different from the existing compounds in two aspects: first, a specific bridging group is connected between the fused ring mother core and the triazine structure of the present invention, which can effectively improve the planar stacking structure of the molecule and promote electron transport; second, in the organic compound of the present invention, the connection site of the triazine structure is different from that of Ref-1. The present invention adopts connection at the Y4-Y7 site, which increases the axial type of the molecule. The lengthening of the axial type can effectively improve the arrangement of the host and guest of the molecule in the light-emitting layer, so that it has better energy transfer effect and better light extraction effect. The combination of the above two points enables the organic compound of the present invention to be used as a light-emitting layer material, which significantly improves the voltage and efficiency of the device.

[0230] The applicant declares that the present invention uses the above-mentioned embodiments to illustrate the organic compounds and their applications, and the organic electroluminescent device of the present invention, but the present invention is not limited to the above-mentioned process steps, that is, it does not mean that the present invention must rely on the above-mentioned process steps to be implemented. Those skilled in the art should understand that any improvement of the present invention, equivalent replacement of the raw materials selected by the present invention, addition of auxiliary components, selection of specific methods, etc., all fall within the protection scope and disclosure scope of the present invention.

Claims

1. An organic compound, characterized in that The organic compound has a structure as shown in Formula I: Wherein, X is S or O; Y1, Y2, Y3, Y4, Y5, Y6, Y7, and Y8 are each independently selected from CR 1 , CR A or N, and at least one of Y1, Y2, Y3, Y4, Y5, Y6, Y7 and Y8 is CR A ; X1, X2, X3, and X4 are each independently selected from CR 2 or any one of N; R 1 , R 2 Each is independently selected from any one of hydrogen, halogen, unsubstituted or R'substituted C1-C20 straight or branched alkyl, unsubstituted or R'substituted C3-C20 cycloalkyl, unsubstituted or R'substituted C2-C20 alkenyl, unsubstituted or R'substituted C1-C20 alkoxy, unsubstituted or R'substituted C1-C20 alkylsilyl, unsubstituted or R'substituted C1-C20 alkylamino, cyano, nitro, hydroxyl, amino, unsubstituted or R'substituted C6-C30 arylamino, unsubstituted or R'substituted C3-C30 heteroarylamino, unsubstituted or R'substituted C6-C30 aryloxy, unsubstituted or R'substituted C3-C30 heteroaryloxy, unsubstituted or R'substituted C6-C60 aryl, and unsubstituted or R'substituted C3-C60 heteroaryl; R A It has the structure shown in formula a: Wherein, -* represents the attachment site of the group; L1 is selected from any one of substituted or unsubstituted C6-C60 arylene groups; Ar1 and Ar2 are each independently selected from any one of a substituted or unsubstituted C6-C60 aryl group and a substituted or unsubstituted C3-C60 heteroaryl group; The substituted substituents and R' in L1, Ar1 and Ar2 are each independently selected from any one of halogen, cyano, nitro, hydroxyl, amino, C1-C20 straight or branched alkyl, C3-C20 cycloalkyl, C2-C20 alkenyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl and C3-C60 heteroaryl, or a combination of at least two thereof; the substituted substituents in L1, Ar1 and Ar2 are each independently not connected to the adjacent ring structure or are connected to form a ring through chemical bonds; the R' is each independently not connected to the adjacent ring structure or are connected to form a ring through chemical bonds.

2. The organic compound according to claim 1, characterized in that The Y1, Y2, Y3, Y4, Y5, Y6, Y7, and Y8 are each independently selected from CR 1 or CR A Any one of, and at least one of Y1, Y2, Y3, Y4, Y5, Y6, Y7 and Y8 is CR A ; Preferably, Y1, Y2, Y3, and Y8 are each independently selected from CR 1 , said Y4, Y5, Y6, Y7 are each independently selected from CR 1 or CR A Any one of, and at least one of Y4, Y5, Y6 and Y7 is CR A ; More preferably, said Y5 is CR A .

3. The organic compound according to claim 1, characterized in that The Y1, Y2, Y3, and Y8 are each independently selected from CR 1 , said Y4, Y5, Y6, Y7 are each independently selected from CR 1 or CR A Any one of, and only one of Y4, Y5, Y6 and Y7 is CR A .

4. The organic compound according to claim 1, characterized in that The R 1 Each is independently selected from any one of hydrogen, unsubstituted or R'-substituted C1-C10 straight or branched alkyl, unsubstituted or R'-substituted C3-C10 cycloalkyl, cyano, unsubstituted or R'-substituted C6-C20 aryl, and unsubstituted or R'-substituted C3-C20 heteroaryl, preferably hydrogen.

5. The organic compound according to claim 1, characterized in that The X1, X2, X3, and X4 are each independently selected from CR 2 ; Preferably, the R 2 Each is independently selected from any one of hydrogen, unsubstituted or R'-substituted C1-C10 straight or branched alkyl, unsubstituted or R'-substituted C3-C10 cycloalkyl, cyano, unsubstituted or R'-substituted C6-C20 aryl, and unsubstituted or R'-substituted C3-C20 heteroaryl, and is more preferably hydrogen.

6. The organic compound according to claim 1, characterized in that The organic compound has a structure as shown in Formula II: Wherein, X, L1, Ar1, Ar2 have the same defined ranges as in Formula I.

7. The organic compound according to claim 1 or 6, characterized in that The L1 is selected from any one of substituted or unsubstituted C6-C20 arylene groups; Preferably, L1 is selected from any one of the following substituted or unsubstituted groups: -* represents the attachment site of the group; Preferably, the substituted substituent in L1 is selected from any one or a combination of at least two of halogen, cyano, C1-C20 straight or branched alkyl, C3-C20 cycloalkyl, C6-C30 aryl, and more preferably any one or a combination of at least two of cyano, C1-C10 straight or branched alkyl, C3-C10 cycloalkyl, C6-C20 aryl.

8. The organic compound according to claim 7, characterized in that The L is selected from any one of the following groups: Wherein, -* represents the attachment site of the group; Preferably, L is selected from any one of the following groups:

9. The organic compound according to claim 7, characterized in that The L is selected from any one of the following substituted or unsubstituted groups: Best Further optimization Any one of; wherein, -* represents the attachment site of the group.

10. The organic compound according to claim 1 or 6, characterized in that The Ar1 and Ar2 are each independently selected from any one of a substituted or unsubstituted C6-C30 aryl group and a substituted or unsubstituted C3-C30 heteroaryl group; Preferably, Ar1 and Ar2 are each independently selected from any one of the following substituted or unsubstituted groups: -* represents the attachment site of the group; Wherein, Z is selected from O, S, CR 11 R 12 or NR 13 Any of the following: R 11 , R 12 , R 13 Each is independently selected from any one or a combination of at least two of a C1-C20 straight or branched alkyl group, a C3-C20 cycloalkyl group, a C2-C20 alkenyl group, a C6-C30 aryl group, and a C3-C30 heteroaryl group; 11 and R 12 Not connected or connected into rings by chemical bonds; Preferably, Z is selected from O, S or CR 11 R 12 Any of the following: Preferably, the R 11 , R 12 Each is independently selected from any one of C1-C10 straight or branched alkyl, C6-C20 aryl; Preferably, the substituents substituted in Ar1 and Ar2 are each independently selected from any one or a combination of at least two of halogen, cyano, C1-C10 straight or branched alkyl, C3-C10 cycloalkyl, C6-C20 aryl, and C3-C20 heteroaryl.

11. The organic compound according to claim 10, characterized in that The Ar1 and Ar2 are each independently selected from any one of the following groups: -* represents the attachment site of the group; Preferably, Ar1 and Ar2 are each independently selected from any one of the following groups:

12. The organic compound according to claim 1, characterized in that The organic compound has a structure shown in any one of the following N1-N176 and S1-S176:

13. Use of an organic compound as claimed in any one of claims 1 to 12, characterized in that: The organic compound is applied to organic electronic devices; Preferably, the organic compound is applied to an organic electroluminescent device; Preferably, the organic compound is used as a light-emitting layer material in an organic electroluminescent device.

14. An organic electroluminescent device, characterized in that: The organic electroluminescent device comprises a first electrode, a second electrode and at least one organic layer disposed between the first electrode and the second electrode; the organic layer comprises at least one organic compound according to any one of claims 1 to 12; Preferably, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises at least one organic compound according to any one of claims 1 to 12; Preferably, the light-emitting layer comprises a host material and a doping material, and the host material comprises at least one organic compound as claimed in any one of claims 1 to 12.

15. The organic electroluminescent device according to claim 14, characterized in that: The host material comprises a combination of a first host material and a second host material, wherein the first host material comprises at least one organic compound according to any one of claims 1 to 12; Preferably, the second host material comprises a compound having a structure as shown in Formula III: Wherein, Ar3, Ar4, and Ar5 are each independently selected from any one of a substituted or unsubstituted C6-C60 aryl group and a substituted or unsubstituted C3-C60 heteroaryl group; Ar3, Ar4, and Ar5 are not connected or are connected to form a ring through a chemical bond; The substituted substituents in Ar3, Ar4 and Ar5 are each independently selected from any one or a combination of at least two of halogen, C1-C20 straight or branched alkyl, C2-C10 alkenyl, C3-C20 cycloalkyl, C2-C20 heterocycloalkyl, C1-C10 alkoxy, carboxyl, nitro, cyano, amino, hydroxyl, mercapto, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl and C3-C60 heteroaryl; the substituted substituents are each independently not connected to the adjacent ring structure or are connected to form a ring through chemical bonds; Preferably, the mass ratio of the first host material to the second host material is (0.1-2):

1.

16. A display device, characterized in that: The display device comprises the organic electroluminescent device according to claim 14 or 15.