An organic compound, application thereof, and an organic electroluminescence device

Abstract

The application provides an organic compound and application thereof, and an organic electroluminescent device, the organic compound has a structure as shown in formula I, through design of a molecular structure and mutual matching and cooperation between groups / structures, the organic compound has the narrow emission spectrum characteristics and high luminous efficiency of a multiple resonance material, has excellent electroluminescent performance, narrow spectrum characteristics and higher thermal stability. The organic compound is used in the organic electroluminescent device, can be used as a fluorescent dopant material of a light-emitting layer, can effectively improve the luminous efficiency and service life of the device, reduce the voltage, and make the device have higher color purity, and endow the device with more excellent comprehensive light-emitting effect.

Description

Technical Field

[0001] This invention belongs to the field of organic electroluminescent materials technology, specifically relating to an organic compound and its applications, and organic electroluminescent devices. Background Technology

[0002] In recent years, electroluminescent devices based on organic materials (such as organic light-emitting diodes, OLEDs) have become increasingly popular. Compared with electroluminescent devices based on inorganic materials, the inherent flexibility of organic materials makes them ideal for manufacturing flexible, thin electroluminescent devices. This allows for the design and production of aesthetically pleasing and stylish screens, displays, and lighting equipment, offering unparalleled advantages over inorganic materials. Currently, OLED-based screens and displays already exhibit good efficiency and lifespan, but achieving long lifespan, high efficiency, and high color purity simultaneously remains a research challenge for OLED devices.

[0003] With the rapid development of information technology, display technology faces higher demands. For example, to meet the BT-2020 color gamut standard for 4K and 8K image signals, the CIEy for green light is 0.797, significantly increasing color gamut coverage. Currently, using luminescent materials with narrow half-width emission spectra is one of the important means to achieve high light color purity. Especially in currently commercialized OLED materials, green luminescent materials mainly use phosphorescent materials with wide half-widths and strong shoulder peaks at long wavelengths, making it difficult to simultaneously meet the requirements of high efficiency and excellent color purity. In recent years, scientists have developed thermally activated delayed fluorescence (TADF) materials that have both 100% theoretical exciton utilization and narrow emission spectra. Using them as OLED luminescent materials is expected to meet the high color purity requirements of BT-2020 while also ensuring high efficiency. However, these materials suffer from severe efficiency roll-off at high brightness and have short device lifetimes, far from meeting the standards for mass production and use. To address this issue, scientists have proposed a superfluorescence strategy, which involves transferring the excited-state energy of TADF or phosphorescent materials to narrow-spectrum fluorescent materials for luminescence. This achieves both theoretically 100% exciton utilization and a narrow emission spectrum, potentially leading to OLED devices with good efficiency, long lifetime, and high color purity. However, existing fluorescent materials still struggle to simultaneously meet the performance requirements of a narrow spectrum, high efficiency, and long lifetime. Furthermore, phosphorescent materials are typically based on transition metals such as iridium and platinum, which are very expensive among OLED materials due to their low abundance. Therefore, reducing the amount of phosphorescent material used is crucial for lowering the cost of OLEDs.

[0004] Therefore, there is an urgent need in this field to develop more types of organic narrow-spectrum luminescent materials with better electroluminescence properties to achieve the above-mentioned expectations. Summary of the Invention

[0005] To address the shortcomings of existing technologies, the present invention aims to provide an organic compound and its applications, as well as an organic electroluminescent device. Based on the design of its molecular structure, the organic compound possesses excellent electroluminescent performance, narrow spectral characteristics, and high quantum efficiency. When used in organic electroluminescent devices, it can effectively improve the luminous efficiency and lifetime of the device, reduce voltage, and improve color purity.

[0006] To achieve this objective, the present invention adopts the following technical solution:

[0007] In a first aspect, the present invention provides an organic compound having the structure shown in Formula I:

[0008]

[0009] In Formula I, Ar1, Ar2, Ar3, and Ar4 are each independently selected from any one of substituted or unsubstituted C6-C60 aryl groups or substituted or unsubstituted C3-C60 heteroaryl groups.

[0010] In Formula I, R1 represents unsubstituted, monosubstituted, or the most permissible substitution; for example, R1 represents unsubstituted (R1 is hydrogen), monosubstituted, disubstituted, trisubstituted, or tetrasubstituted; when R1 represents disubstituted, trisubstituted, or tetrasubstituted, multiple R1s may be the same or different groups.

[0011] R1 is selected from hydrogen, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C6-C30 arylsilyl, substituted or unsubstituted C6-C30 heteroarylsilyl, substituted or unsubstituted C1-C20 alkylamino, etc. The R1 may be any one of the following: substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C60 aryl, or substituted or unsubstituted C3-C60 heteroaryl; at least two adjacent groups in the R1 may not be connected to each other or may be linked to each other by chemical bonds to form a ring; the R1 may not be connected to the adjacent ring structure or may be linked to each other by chemical bonds to form a ring.

[0012] In this invention, "R1 is not connected to adjacent ring structures" means that R1 is only connected to the C atoms of the benzene ring through single bonds; "R1 is connected to adjacent ring structures through chemical bonds to form a ring" means that in addition to being connected to the C atoms of the benzene ring through chemical bonds, R1 is also connected to adjacent rings through chemical bonds, thereby forming a fused ring structure. When the same description is used in this document, it has the same meaning and will not be elaborated further.

[0013] In Formula I, dashed lines represent single bonds or no connection; m1 and m2 are independently 0 or 1. Specifically, when a dashed line represents a single bond, it means that the benzene ring containing Ar1 is connected to the benzene ring containing Ar2 through X1 (i.e., m1 is 1), and / or, the benzene ring containing aromatic amine N is connected to the benzene ring containing R3 through X2 (i.e., m2 is 1). When a dashed line represents no connection, that is, the chemical bond shown by the dashed line does not exist, the benzene ring containing Ar1 is not connected to the benzene ring containing Ar2 (i.e., m1 is 0), and / or, the benzene ring containing aromatic amine N is not connected to the benzene ring containing R3 (i.e., m2 is 0). The same descriptions will have the same meaning in the following text and will not be repeated hereafter.

[0014] In Formula I, X1 and X2 are each independently selected from any one of single bond, O, S, NR4, CR5R5' or SiR6R6'.

[0015] In Formula I, Y is selected from any one of single bond, O, S, CR7R7' or SiR8R8'.

[0016] It should be noted that when Y is a single bond, it indicates that ring A and ring B are connected by a single bond to form a five-membered ring (pyrrole ring); when Y is selected from O, S, CR7R7', or SiR8R8', it indicates that ring A and ring B are connected by Y to form a six-membered ring. When the same description is used in this article, it has the same meaning and will not be elaborated further.

[0017] R4, R5, R5', R6, R6', R7, R7', R8, and R8' are each independently selected from any one of the following: substituted or unsubstituted C1-C20 straight-chain or branched alkyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, substituted or unsubstituted C2-C20 alkenyl groups, substituted or unsubstituted C6-C60 aryl groups, and substituted or unsubstituted C3-C60 heteroaryl groups; R5 and R5' are not connected or are linked by chemical bonds to form a ring; R6 and R6' are not connected or are linked by chemical bonds to form a ring; R7 and R7' are not connected or are linked by chemical bonds to form a ring; and R8 and R8' are not connected or are linked by chemical bonds to form a ring.

[0018] In Formula I, ring A and ring B are each independently selected from any one of substituted or unsubstituted C6-C60 aromatic rings or substituted or unsubstituted C3-C60 heteroaromatic rings.

[0019] The substituents described in Ar1, Ar2, Ar3, Ar4, cycloA, cycloB, R1, R4, R5, R5', R6, R6', R7, R7', R8, and R8' are each independently selected from halogens, unsubstituted or R'-substituted C1-C20 straight-chain or branched alkyl groups, unsubstituted or R'-substituted C3-C20 cycloalkyl groups, unsubstituted or R'-substituted C1-C20 alkoxy groups, unsubstituted or R'-substituted C2-C20 alkenyl groups, unsubstituted or R'-substituted C1-C20 alkylsilyl groups, unsubstituted or R'-substituted C1-C20 alkylamino groups, unsubstituted or R'-substituted C6-C30 arylsilyl groups, and unsubstituted or R'-substituted... The substituted C6-C30 heteroarylsilyl, 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; each of the substituted substituents is independently not connected to or is linked to an adjacent ring structure by a chemical bond to form a ring, and at least two adjacent groups of the substituted substituents are not connected to or are linked to each other by a chemical bond to form a ring.

[0020] In this invention, the "substituted or unsubstituted" group can replace one substituent or multiple substituents. When there are multiple substituents (at least two), they can be the same or different substituents; the same expression used below has the same meaning. Unless otherwise specified, the selection range of substituents is as shown above and will not be repeated.

[0021] Each R' is independently selected from any one or a combination of at least two of the following: halogen, cyano, nitro, hydroxyl, amino, C1-C20 straight-chain or branched alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C30 arylsilyl, C6-C30 heteroarylsilyl, C6-C60 aryl, and C3-C60 heteroaryl; at least two adjacent R's are not connected or are linked by chemical bonds to form a ring; the R's are not connected to adjacent ring structures or are linked by chemical bonds to form a ring.

[0022] In the present invention, the "unsubstituted or R'-substituted" group may be substituted with one substituent R' or a plurality of substituents R'. When the number of substituents R' is plural (at least 2), the substituents may be the same or different; the same expressions appearing hereinafter all have the same meaning. Unless otherwise specified, the optional range of R' is as defined above, and will not be repeated hereinafter.

[0023] The organic compound provided by the present invention has a structure represented by Formula I. In the boron-containing multiple resonance core structure, aromatic groups Ar1 and Ar2 are connected to the para-position of N, and the formed "biaryl" (e.g., biphenyl) structure can increase the proportion of horizontal light-emitting dipoles; at the same time, the fused ring structure formed by introducing Ring A, Ring B and Y locks the core, reducing the structural relaxation of the molecule in the excited state. In addition, the fused ring structure is orthogonal to the core structure, which can suppress intermolecular aggregation. Moreover, no other substituent is connected to the benzene ring at the center of the core (i.e., the benzene ring with three adjacent sites respectively connected to N, B and N), so that the entire compound has a suitable (relatively small) molecular weight, which is beneficial to lowering the sublimation temperature and fully meets the processing requirements such as device evaporation. Through the design of the molecular structure and the mutual coordination between groups / structures, the organic compound of the present invention has the narrow emission spectrum characteristic and high luminous efficiency of a multiple resonance material, exhibiting excellent electroluminescent performance, narrow spectral characteristic and thermal stability. When applied to an organic electroluminescent device, the organic compound can be used as a fluorescent doping material for the light-emitting layer, which can effectively improve the luminous efficiency of the device, prolong the service life of the device, endow the device with higher color purity, and impart more excellent comprehensive light-emitting effect to the device.

[0024] It should be noted that in the present invention, the possible functions of each group / feature are described separately for the convenience of illustration, but this does not mean that these groups / features function in isolation. In fact, the essential reason for obtaining good performance lies in the optimized combination of the entire molecular structure, which is the result of the synergistic effect between the various groups, rather than the effect of a single group / feature.

[0025] 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.

[0026] In the present invention, the halogen may each be fluorine, chlorine, bromine or iodine. The same descriptions appearing hereinafter all have the same meaning.

[0027] In the present invention, the reference to chemical elements, unless otherwise specified, encompasses the concept of isotopes having the same chemical properties. For example, hydrogen (H) includes 1 H (protium), 2 H (deuterium, D), 3 H (tritium, T) and the like; carbon (C) includes12 C 13 C, etc.

[0028] In this invention, unless otherwise specified, the heteroatoms of the heteroaryl group are selected from N, O, S, P, B, Si or Se, preferably N, O or S.

[0029] In this invention, the way the ring structure is represented by "—" indicates that the connection point is located at any position on the ring structure where bonding can occur.

[0030] In this invention, "——*" and "*" both represent the linking sites of functional groups.

[0031] In this invention, "each independently" means that when there are multiple subjects, they can be the same or different from each other.

[0032] In this invention, the expression Ca-Cb represents that the group has ab carbon atoms. Unless otherwise specified, the number of carbon atoms does not include the number of carbon atoms of the substituents.

[0033] 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.

[0034] 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.

[0035] C1-C20 can all be C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.

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

[0037] 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.

[0038] C6-C30 can all be C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26 or C28, etc.

[0039] C3-C30 can all be C3, C4, C5, C6, C7, C8, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26 or C28, etc.

[0040] In this invention, the C6-C60 aryl (C6-C60 aromatic ring), preferably C6-C30 aryl (C6-C30 aromatic ring), includes monocyclic aryl and fused-ring aryl groups; the monocyclic aryl means that the group contains at least one phenyl group, and when it contains at least two phenyl groups, the phenyl groups are linked by single bonds, exemplarily including but not limited to: phenyl, biphenyl, terphenyl, tetraphenyl, etc.; the fused-ring aryl means that the group contains at least two rings (and at least one ring is an aromatic ring). Furthermore, the rings share two adjacent carbon atoms bonded together by a group, exemplarily including but not limited to: naphthyl, anthraceneyl, phenanthryl, indene, 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, spirodifluorenyl, benzo[a]fluorenyl, etc.), fluoranthyl, triphenylene, pyrene, perylene, Aryl, tetraphenyl, acenaphthenyl, benzo[a]acenaphthenyl, etc. It should be noted that monocyclic aryl and fused-ring aryl groups linked by single bonds also fall under the category of aryl groups, such as phenylnaphthyl, naphthylphenyl, and binaphthyl.

[0041] The C3-C60 heteroaryl group (C3-C60 heteroaryl ring), preferably C6-C30 heteroaryl group (C3-C30 heteroaryl ring), includes monocyclic heteroaryl groups or fused-ring heteroaryl groups. A monocyclic heteroaryl group means that the molecule contains at least one heteroaryl group. When the molecule contains one heteroaryl group and other groups (such as aryl, heteroaryl, etc.), the heteroaryl group and other groups are connected by a single bond, exemplarily including but not limited to: pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thiophene, pyrroleyl, bipyridinyl, phenylpyridinyl, pyridylphenyl, etc. The term "fused-ring heteroaryl" refers to a molecule containing at least one aromatic heterocycle and one aromatic ring (aromatic heterocycle or aromatic ring), with the two sharing two adjacent atoms fused together in a group. Exemplary examples include, but are not limited to: quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, isobenzofuranyl, isobenzothiopheneyl, indolyl, dibenzofuranyl, dibenzothiopheneyl, carbazoleyl and its derivatives (N-phenylcarbazoleyl, N-naphthylcarbazoleyl, benzocarbazoleyl, dibenzocarbazoleyl, indolocarbazoleyl, azacarbazoleyl, etc.), acridineyl, phenothiazinyl, phenotoxazinyl, hydrogenated acridineyl, etc. It should be noted that heteroaryl groups linked by single bonds, and aryl groups linked by single bonds, also fall within the scope of heteroaryl groups, such as phenylpyridinyl, phenylpyrimidinyl, pyridylphenyl, pyrimidinylphenyl, etc.

[0042] In this invention, specific examples of the C6-C60 arylamino and C6-C30 arylamino groups are monovalent groups obtained by substituting at least one hydrogen atom in -NH2 with the aforementioned aryl group, including but not limited to: phenylamino, methylphenylamino, naphthylamino, anthraceneylamino, phenanthreneamino, biphenylamino, etc. Specific examples of the C3-C60 heteroarylamino and C3-C30 heteroarylamino groups are monovalent groups obtained by substituting at least one hydrogen atom in -NH2 with the aforementioned heteroaryl group, including but not limited to: pyridylamino, pyrimidinylamino, dibenzofuranylamino, etc.

[0043] In this invention, the C6-C30 aryloxy group is a monovalent group formed by connecting the above-mentioned aryl group with O, and the C3-C30 heteroaryloxy group is a monovalent group formed by connecting the above-mentioned heteroaryl group with O.

[0044] A specific example of the C6-C30 arylsilyl group is a monovalent group obtained by replacing at least one hydrogen in -SiH3 with the aforementioned aryl group; a specific example of the C6-C30 heteroarylsilyl group is a monovalent group obtained by replacing at least one hydrogen in -SiH3 with the aforementioned heteroaryl group.

[0045] The C1-C20 straight-chain or branched alkyl group, preferably C1-C16 straight-chain or branched alkyl group, and more preferably C1-C10 straight-chain or branched alkyl group, includes, but is not limited to: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 2-methylbutyl, n-pentyl, isopentyl, neopentyl, n-hexyl, neohexyl, 2-ethylhexyl, n-octyl, n-heptyl, n-nonyl, n-decyl, etc.

[0046] Specific examples of the C1-C20 alkoxy groups can be exemplified by the monovalent groups obtained by connecting the above-mentioned straight-chain or branched alkyl groups to O.

[0047] Specific examples of the C1-C20 alkylsilyl group are monovalent groups formed by replacing at least one hydrogen in -SiH3 with the aforementioned straight-chain or branched alkyl groups, including but not limited to: trimethylsilyl, dimethylsilyl, di(methyl)ethylsilyl, di(methyl)propylsilyl, triethylsilyl, tripropylsilyl, etc.

[0048] The C3-C20 cycloalkyl group, preferably C3-C10 cycloalkyl group, includes monocycloalkyl or polycycloalkyl groups. Monocycloalkyl refers to an alkyl group containing a single ring structure, while polycycloalkyl refers to a structure formed by two or more cycloalkyl groups sharing one or more carbon atoms on a ring; exemplary examples include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and adamantyl.

[0049] The C2-C20 alkenyl group, preferably C2-C10 alkenyl group, contains at least one C=C, and includes, but is not limited to: vinyl, propenyl, allyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, butadienyl, pentadienyl, etc.

[0050] As a preferred embodiment of the present invention, the organic compound has the structure shown in Formula II:

[0051]

[0052] Among them, Ar1, Ar2, Ar3, Ar4, X1, X2, Y, ring A, ring B, R1, m1 and m2 have the same limited range as in Equation I.

[0053] As a preferred embodiment of the present invention, Ar3 and Ar4 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, C24, C26, or C28, etc.) aryl groups, preferably any one of substituted or unsubstituted C6-C20 aryl groups, further preferably any one of the following substituted or unsubstituted groups: phenyl, biphenyl, terphenyl, or naphthyl, more preferably substituted or unsubstituted phenyl.

[0054] As a preferred embodiment of the present invention, the organic compound has the structure shown in Formula III:

[0055]

[0056] Among them, Ar1, Ar2, Ar3, Ar4, X1, X2, Y, ring A, ring B, R1, m1 and m2 have the same limited range as in Equation I.

[0057] R2 and R3 each independently represent unsubstituted, monosubstituted, or the most permissible substitution. For example, R2 can represent unsubstituted (R2 is hydrogen), monosubstituted, disubstituted, trisubstituted, tetrasubstituted, or pentasubstituted groups. When R2 represents disubstituted, trisubstituted, tetrasubstituted, or pentasubstituted groups, multiple R2s can be the same or different groups. The expression of R3 is similar, and for the sake of brevity, it will not be repeated.

[0058] R2 and R3 are each independently selected from hydrogen, halogen, unsubstituted or R'-substituted C1-C20 straight-chain or branched alkyl groups, unsubstituted or R'-substituted C3-C20 cycloalkyl groups, unsubstituted or R'-substituted C1-C20 alkoxy groups, unsubstituted or R'-substituted C2-C20 alkenyl groups, unsubstituted or R'-substituted C1-C20 alkylsilyl groups, unsubstituted or R'-substituted C1-C20 alkylamino groups, unsubstituted or R'-substituted C6-C30 arylsilyl groups, unsubstituted or R'-substituted C6-C30 heteroarylsilyl groups, cyano, nitro, hydroxy, and amino groups. The R2 and R3 groups are any one of the following: arylamine, 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; at least two adjacent groups in R2 and R3 are not connected to each other or are linked to form a ring by chemical bonds; R2 and R3 are not connected to adjacent ring structures or are linked to form a ring by chemical bonds.

[0059] As a preferred embodiment of the present invention, m1 is 1 (i.e., the dashed lines on both sides of X1 represent single bonds); and / or, m2 is 1 (i.e., the dashed lines on both sides of X2 represent single bonds).

[0060] As a preferred embodiment of the present invention, X1 is a single bond and m1 is 1. In this case, the ring containing X1 is a five-membered ring (pyrrole ring), which forms a carbazole structure with the benzene rings fused on both sides.

[0061] And / or, X2 is a single bond and m2 is 1. In this case, the ring containing X2 is a five-membered ring (pyrrole ring), which forms a carbazole structure with the benzene rings fused on both sides.

[0062] In a preferred embodiment of the present invention, Y is a single bond.

[0063] As a preferred embodiment of the present invention, ring A and ring B each independently have the structure shown in formula A:

[0064]

[0065] The dashed lines represent the fused bonds of the ring.

[0066] U1, U2, U3, and U4 are each independently selected from N or CR. A Multiple (2-4) CRs A R in A These can be the same or different groups.

[0067] R A Each is independently selected from hydrogen, halogen, unsubstituted or R'-substituted C1-C20 straight-chain or branched alkyl, unsubstituted or R'-substituted C3-C20 cycloalkyl, unsubstituted or R'-substituted C1-C20 alkoxy, unsubstituted or R'-substituted C2-C20 alkenyl, unsubstituted or R'-substituted C1-C20 alkylsilyl, unsubstituted or R'-substituted C1-C20 alkylamino, unsubstituted or R'-substituted C6-C30 arylsilyl, unsubstituted or Any one of the following: R'-substituted C6-C30 heteroarylsilyl, 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; unsubstituted or R'-substituted C3-C60 heteroaryl; wherein R A Each of the Rs is independent and not connected to adjacent ring structures or is connected to form a ring by chemical bonds. A At least two adjacent groups in the group are not connected or are linked by chemical bonds to form a ring.

[0068] Preferably, at most one (0 or 1) of U1, U2, U3, and U4 is N; more preferably, each of U1, U2, U3, and U4 is independently selected from CR. A .

[0069] As a preferred embodiment of the present invention, ring A and ring B are each independently substituted or unsubstituted benzene rings, and Y is a single bond, thereby forming a "fluorene structure". This fluorene structure locks the parent nucleus structure, reducing the structural relaxation of the molecule in the excited state. In addition, the "fluorene structure" and the parent nucleus are orthogonal, which can suppress the aggregation between molecules, thereby giving the organic compound better electroluminescence performance, photoelectric efficiency and stability.

[0070] As a preferred embodiment of the present invention, the organic compound has the structure shown in Formula IV:

[0071]

[0072] Ar1, Ar2, R1, R2, and R3 have the same defined range as in Equation III.

[0073] R A1 and R A2 Each can be independently represented from no substitution, single substitution to the maximum permissible substitution; for example, R A1 Indicates no substitution (R) A1 (for hydrogen), monosubstituted, disubstituted, trisubstituted, or tetrasubstituted, etc.; when R A1 When indicating di-, tri-, or tetra-substituted substitutions, multiple Rs A1 For the same or different groups; R A2 The same applies to the other two expressions; for the sake of brevity, I will not repeat them.

[0074] R A1 R A2 Each is independently selected from hydrogen, halogen, unsubstituted or R'-substituted C1-C20 straight-chain or branched alkyl, unsubstituted or R'-substituted C3-C20 cycloalkyl, unsubstituted or R'-substituted C1-C20 alkoxy, unsubstituted or R'-substituted C2-C20 alkenyl, unsubstituted or R'-substituted C1-C20 alkylsilyl, unsubstituted or R'-substituted C1-C20 alkylamino, unsubstituted or R'-substituted C6-C30 arylsilyl, unsubstituted or Any one of the following: R'-substituted C6-C30 heteroarylsilyl, 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; unsubstituted or R'-substituted C3-C60 heteroaryl; wherein R A1 R A2 In the presence of at least two adjacent groups, they are either not connected or are linked by chemical bonds to form a ring; the R A1 R A2Each ring is independent and not connected to the adjacent ring structure or is connected to form a ring by chemical bonds.

[0075] As a preferred embodiment of the present invention, 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, C24, C25, C26, C28, etc.) aryl groups and substituted or unsubstituted C3-C30 (e.g., C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C25, C26, C28, etc.) heteroaryl groups, preferably substituted or unsubstituted C6-C20 aryl groups, more preferably any one of the following groups: phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthryl, and even more preferably substituted or unsubstituted phenyl or substituted or unsubstituted biphenyl groups.

[0076] Preferably, the substituents in Ar1 and Ar2 are each independently selected from halogens, cyano groups, unsubstituted or R'-substituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight-chain or branched alkyl groups, unsubstituted or R'-substituted C3-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) cycloalkyl groups, unsubstituted or R'-substituted C2-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkenyl groups, unsubstituted or R'-substituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkylsilyl groups, etc. Any one of unsubstituted or R'-substituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, etc.) aryl, unsubstituted or R'-substituted C3-C20 (e.g., C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, etc.) heteroaryl, further preferably any one of halogen, cyano, unsubstituted or halogenated C1-C10 straight-chain or branched alkyl, C1-C10 alkylsilyl, C6-C18 aryl, more preferably fluorine, methyl, trifluoromethyl, ethyl, isopropyl, tert-butyl, sec-butyl, isobutyl, isopentyl, tert-amyl, neopentyl or trimethylsilyl.

[0077] Preferably, Ar1 and Ar2 are each independently selected from any one of the following groups:

[0078]

[0079] More preferably, Ar1 and Ar2 are each independently selected from any one of the following groups:

[0080] —* represents the linking site of a functional group.

[0081] As a preferred embodiment of the present invention, R1 is selected from hydrogen, halogen, cyano, substituted or unsubstituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight-chain or branched alkyl, substituted or unsubstituted C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, substituted or unsubstituted C2-C10 (e.g., C3, C4, C5, C6, C7, C8, C9, etc.) alkenyl, substituted or unsubstituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkylsilyl, substituted or unsubstituted C6-C20 (e.g., C6, C9, C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkylsilyl, and substituted or unsubstituted C6-C20 (e.g., C6, C9, C2 ... Any one of the following groups: aryl (C10, C12, C14, C15, C16, C18, etc.), substituted or unsubstituted C3-C20 (e.g., C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, etc.), preferably hydrogen, halogen, substituted or unsubstituted group: C1-C6 straight-chain or branched alkyl, C1-C10 alkylsilyl, phenyl, biphenyl, terphenyl, naphthyl, anthraceneyl, phenanthrene, more preferably hydrogen, methyl, trifluoromethyl, ethyl, isopropyl, tert-butyl, sec-butyl, isobutyl, isopentyl, tert-pentyl, neopentyl or trimethylsilyl, more preferably hydrogen, tert-butyl or phenyl.

[0082] Preferably, R1 represents unsubstituted (R1 is hydrogen) or monosubstituted, and in the case of monosubstituted R1, the linkage site on the benzene ring is the para position of the N-linked site.

[0083] As a preferred embodiment of the present invention, in Formula III, R2 and R3 are each independently selected from hydrogen, halogen, cyano, unsubstituted or R'-substituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight-chain or branched alkyl groups, unsubstituted or R'-substituted C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl groups, unsubstituted or R'-substituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkylsilyl groups, and unsubstituted... The preferred group is any one of the following: C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, etc.) aryl groups that are substituted or R'-substituted, or unsubstituted or R'-substituted C3-C20 (e.g., C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, etc.) heteroaryl groups. The preferred group is hydrogen, halogen, or any one of the following groups that are unsubstituted or R'-substituted: C1-C6 straight-chain or branched alkyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, with hydrogen being even more preferred.

[0084] As a preferred embodiment of the present invention, in formula IV, R A1 R A2 Each is independently selected from hydrogen, halogen, cyano, unsubstituted or R'-substituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight-chain or branched alkyl, unsubstituted or R'-substituted C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, unsubstituted or R'-substituted C2-C10 (e.g., C3, C4, C5, C6, C7, C8, C9, etc.) alkenyl, unsubstituted or R'-substituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkylsilyl, unsubstituted or R'-substituted C6-C20 (e.g., C6, C9, C9, C2 ... The following groups are preferred: aryl (C1-C10, C12, C14, C15, C16, C18, etc.), unsubstituted or R'-substituted C3-C20 (e.g., C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, etc.) heteroaryl groups; hydrogen, halogen, unsubstituted or R'-substituted groups are preferred: C1-C6 straight-chain or branched alkyl, C1-C10 alkylsilyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene; hydrogen, phenyl, methyl, trifluoromethyl, ethyl, isopropyl, tert-butyl, sec-butyl, isobutyl, isopentyl, tert-pentyl, neopentyl or trimethylsilyl.

[0085] As a preferred embodiment of the present invention, the organic compound has any of the following structures:

[0086]

[0087]

[0088]

[0089]

[0090] In a second aspect, the present invention provides an application of the organic compound as described in the first aspect, wherein the organic compound is applied to an organic electronic device.

[0091] 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, and more preferably an organic electroluminescent device.

[0092] Preferably, the organic electronic device includes an organic electroluminescent device.

[0093] Preferably, the organic compound is used as a light-emitting layer material in an organic electroluminescent device.

[0094] Preferably, all organic compounds are used as dopant materials (also known as "dyes", "dopants", or "guest materials") in organic electroluminescent devices as dopant materials for the light-emitting layer.

[0095] Thirdly, the present invention provides an organic electroluminescent device, the 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 comprising at least one organic compound as described in the first aspect.

[0096] Preferably, the organic layer includes a light-emitting layer, wherein the light-emitting layer includes at least one organic compound as described in the first aspect.

[0097] Preferably, the light-emitting layer comprises a host material and a dopant material, wherein the dopant material (also known as a "dopant", "dye", or "guest material") comprises at least one organic compound as described in the first aspect.

[0098] Preferably, the organic compound provided by the present invention is used as the fluorescent dopant material (i.e., fluorescent dye) of the light-emitting layer.

[0099] Preferably, the mass percentage of the doped material in the light-emitting layer is 0.1-10%, for example, it can be 0.2%, 0.5%, 0.8%, 1%, 1.5%, 2%, 2.5%, 3%, 4%, 5%, 6%, 7%, 8% or 9%, and more preferably 0.3-3%.

[0100] Preferably, the host material includes any one or a combination of at least two of the following: P-type host material, N-type host material, and monomolecular excitosome host material.

[0101] Preferably, the light-emitting layer further includes a sensitizer.

[0102] Preferably, the sensitizer includes any one or a combination of at least two of thermally activated delayed fluorescence materials and phosphorescent materials.

[0103] Preferably, the energy (T1) of the lowest triplet state of the sensitizer is greater than or equal to the energy (S1) of the lowest singlet state of the organic compound of the present invention.

[0104] Preferably, the maximum emission wavelength of the sensitizer is less than the maximum emission wavelength of the organic compound of the present invention.

[0105] Preferably, the mass percentage of the sensitizer in the luminescent layer is 0.1-40%, for example, it can be 0.5%, 1%, 1.5%, 2%, 2.5%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 15%, 20%, 25%, 30% or 35%, etc.

[0106] Preferably, the sensitizer comprises a phosphorescent material (phosphorescent sensitizer), and the mass percentage of the phosphorescent material in the luminescent layer is 0.1-10%.

[0107] Preferably, the sensitizer is a thermally activated delayed fluorescence material, and the mass percentage of the thermally activated delayed fluorescence material in the luminescent layer is 1-40%.

[0108] Preferably, the organic layer further includes a hole transport region and an electron transport region. The hole transport region is located between the anode and the light-emitting layer, and the electron transport region is located between the cathode and the light-emitting layer.

[0109] Preferably, the hole transport region includes any one or a combination of at least two of the following: a hole injection layer, a hole transport layer, and an electron blocking layer.

[0110] Preferably, the electron transport region includes any one or a combination of at least two of the electron injection layer, electron transport layer, and hole blocking layer.

[0111] In a preferred embodiment, 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 further divided into multiple regions, such as a hole transport region, a light-emitting layer, and an electron transport region; the light-emitting layer contains at least one organic compound as described in the first aspect.

[0112] In a preferred embodiment, the organic electroluminescent device includes a first electrode, a plurality of light-emitting functional layers (organic layers), and a second electrode arranged sequentially. The organic layers include 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 sequentially, with the hole injection layer 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.

[0113] In a preferred embodiment, a substrate can be used below the first electrode or above the second electrode. The substrate is typically made of glass or polymer material possessing excellent mechanical strength, thermal stability, water resistance, and transparency. Furthermore, the substrate used for a display may also incorporate thin-film transistors (TFTs).

[0114] The first electrode can be formed by sputtering or depositing the material to be used as the first electrode on a substrate. When the first electrode is used as the anode, it can be a transparent conductive oxide material such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), zinc oxide (ZnO), or any combination thereof. When the first electrode is used as the cathode, it can be 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), or any combination thereof.

[0115] Organic layers can be formed on electrodes using methods such as vacuum thermal evaporation, spin coating, and printing. The compounds used as organic layers can be small organic molecules, large organic molecules, or polymers, as well as combinations thereof.

[0116] The hole transport region is located between the anode and the emissive layer. The hole transport region can be a single-layer hole transport layer (HTL), including single-layer hole transport layers containing only one compound and single-layer hole transport layers containing multiple compounds. Alternatively, the hole transport region can be a multilayer structure including at least one 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 emissive layer.

[0117] The material for the hole transport region may be selected from, but is 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 compounds shown in HT-1 to HT-51 below; or any combination thereof.

[0118]

[0119]

[0120]

[0121] 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 be one or more compounds of HT-1 to HT-51 described above, or one or more compounds of HI-1 to HI-3 described below; it can also be one or more compounds of HT-1 to HT-51 doped with one or more compounds of HI-1 to HI-3 described below.

[0122]

[0123] The emissive layer consists of a luminescent dye (i.e., a dopant) that emits different wavelengths of light and a host material. The emissive layer can be a monochromatic layer emitting a single color such as red, green, or blue. Multiple monochromatic emissive layers of different colors can be arranged in a planar pattern according to pixel design, or they can be stacked together to form a colored emissive layer. When different colored emissive layers are stacked together, they can be separated from each other or connected to each other. The emissive layer can also be a single colored emissive layer that simultaneously emits different colors such as red, green, and blue.

[0124] In one aspect of the invention, the light-emitting layer employs phosphorescent photoluminescence technology, and the main material of the light-emitting layer is selected from, but not limited to, one or more combinations of PH-1 to PH-117.

[0125]

[0126]

[0127]

[0128]

[0129]

[0130] In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescence technology. Its sensitizer, the phosphorescent material, may be selected from, but is not limited to, one or more combinations of GPD-1 to GPD-60 listed below.

[0131]

[0132]

[0133]

[0134] Where D represents deuterium.

[0135] In one aspect of the present invention, the light-emitting layer employs thermally activated sensitized fluorescence luminescence technology, and the main material of the light-emitting layer is selected from, but not limited to, one or more combinations of PH-1 to PH-117 mentioned above.

[0136] In one aspect of the invention, the luminescent layer employs thermally activated sensitized fluorescence luminescence technology. The sensitizer of the luminescent layer, i.e., the thermally activated delayed fluorescence material, can be selected from, but is not limited to, one or more combinations of TDE1-TDE49 listed below.

[0137]

[0138]

[0139]

[0140]

[0141] In one aspect of the invention, the light-emitting layer employs a combination of phosphorescence-sensitized luminescence and thermally activated sensitized fluorescence luminescence. The main material of the light-emitting layer is selected from, but not limited to, one or more combinations of PH-1 to PH-117 described above.

[0142] In one aspect of the invention, the light-emitting layer employs a combination of phosphorescent sensitization and thermally activated sensitized fluorescence. The sensitizer in the light-emitting layer includes both phosphorescent materials and thermally activated delayed fluorescence materials. The phosphorescent materials may be selected from, but are not limited to, GPD-1 to GPD-47 listed above, and the thermally activated delayed fluorescence materials may be selected from, but are not limited to, TDE1 to TDE49 listed above.

[0143] 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 employ, but is not limited to, one or more compounds of HT-1 to HT-51 described above, or one or more compounds of PH-47 to PH-77 described above; or a mixture of one or more compounds of HT-1 to HT-51 and one or more compounds of PH-47 to PH-77 may be employed.

[0144] The organic layer of an OLED may also include an electron transport region between the light-emitting layer and the cathode. The electron transport region can be a single-layer electron transport layer (ETL), including single-layer electron transport layers containing only one compound and single-layer electron transport layers containing multiple compounds. Alternatively, the electron transport region can be a multilayer structure including at least one of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0145] In one aspect of the present invention, the electron transport layer material may be selected from, but not limited to, one or more combinations of ET-1 to ET-73 listed below.

[0146]

[0147]

[0148]

[0149]

[0150] 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 employ, but is not limited to, one or more compounds of ET-1 to ET-73, or one or more compounds of PH-1 to PH-74; or a mixture of one or more compounds of ET-1 to ET-73 and one or more compounds of PH-1 to PH-74 may be employed.

[0151] 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, Yb.

[0152] The present invention also provides a display device comprising an organic electroluminescent device as described in the third aspect.

[0153] Preferably, the display device includes a display screen or a display panel.

[0154] The present invention also provides an electronic device, which includes the aforementioned display device.

[0155] Compared with the prior art, the present invention has the following beneficial effects:

[0156] The organic compounds provided by this invention, through the design of their molecular structures and the mutual compounding and synergistic effects between various groups / structures, possess the narrow emission spectrum characteristics and high luminous efficiency of multiple resonance materials, exhibiting excellent electroluminescence performance, narrow spectral characteristics, and higher thermal stability. When used in organic electroluminescent devices, these organic compounds can serve as fluorescent dopant materials in the luminescent layer, effectively improving the luminous efficiency and lifetime of the device, reducing voltage, and giving the device higher color purity, thus endowing it with superior overall luminous effect. Detailed Implementation

[0157] The technical solution of the present invention will be further illustrated below through specific embodiments. Those skilled in the art should understand that the embodiments described are merely illustrative of the present invention and should not be construed as limiting the invention in any way.

[0158] The organic compounds represented by Formula I provided by this invention can be synthesized using organic synthesis methods known in the art. Exemplary synthetic routes are given below, but those skilled in the art can also obtain them using other known methods.

[0159] In one specific embodiment, the organic compound has the structure shown in Formula I and can be prepared via the synthetic route shown below:

[0160]

[0161] Ar1, Ar2, Ar3, Ar4, X1, X2, Y, ring A, ring B, R1, m1, and m2 have the same defined range as in Formula I; Hal1, Hal2, Hal3, and Hal4 are each independently selected from halogens, such as any one of F, I, Br, or Cl. The order of reactions I and II can be adjusted according to the synthesis situation; that is, reaction I can be carried out first, followed by reaction II, or reaction II can be carried out first, followed by reaction I.

[0162] In one specific embodiment, Hal1 and Hal2 are F, Hal3 is Br, and Hal4 is Cl.

[0163] In one specific embodiment, reactions I and II are carried out in the presence of cesium carbonate.

[0164] In one specific embodiment, the organolithium reagent in reaction III includes n-butyllithium (n-BuLi).

[0165] In one specific embodiment, reaction V is carried out in the presence of an organolithium reagent (e.g., tert-butyllithium t-BuLi) and an amine compound (e.g., N,N-diisopropylethylamine).

[0166] It should be noted that obtaining the organic compounds is not limited to the synthetic methods and raw materials used in this invention. Those skilled in the art can also select other methods or routes to obtain the organic compounds proposed in this invention. Compounds synthesized using methods not mentioned in this invention are all raw material products obtained through commercial means, or prepared in-house using these raw material products according to known methods.

[0167] The specific preparation methods of the organic compounds described in this invention will be detailed below using several synthetic examples, but the preparation methods of this invention are not limited to these synthetic examples.

[0168] The intermediate compounds and target products in the following synthesis examples of this invention were analyzed and detected using a high-resolution mass spectrometer (Agilent HPLC-6500 series high-resolution Q-TOF liquid chromatography-mass spectrometry system), and the ionization source was an atmospheric pressure chemical ionization ionization source (APCI source).

[0169] Synthesis Example 1: Synthesis of Organic Compound M001

[0170]

[0171] (1) Synthesis of intermediate M001-1:

[0172] SM-1 (10.0 g), SM-2 (14 g), cesium carbonate (28.6 g), and N,N-dimethylformamide (DMF) (150 mL) were added to a 500 mL three-necked flask. The mixture was purged with nitrogen three times and reacted at 75 °C for 12 h. The reaction solution was cooled to room temperature, poured into water, filtered, dried, mixed with silica gel, and purified by column chromatography to obtain intermediate M001-1, 16 g of white solid. The molecular ion mass determined by mass spectrometry was 526.1326 (theoretical value: 525.0295).

[0173] (2) Synthesis of intermediate M001-2:

[0174] M001-1 (14 g), SM-3 (11.4 g), cesium carbonate (17.3 g), and DMF (140 mL) were added to a 250 mL single-necked flask, purged with nitrogen three times, and reacted at 100 °C for 12 h. The reaction solution was cooled to room temperature, poured into water, filtered, dried, and recrystallized from dichloromethane / ethanol to obtain intermediate M001-2, 18 g of white solid. Mass spectrometry analysis determined the molecular ion mass to be 840.3564 (theoretical value: 839.1703).

[0175] (3) Synthesis of intermediate M001-3:

[0176] Intermediate M001-2 (16 g) and tetrahydrofuran (240 mL) were added to a 500 mL three-necked flask, stirred and dissolved, and purged with nitrogen three times. The reaction system was then cooled to -70 °C, and n-butyllithium (n-BuLi) (10.3 mL, 2.4 M concentration) was added dropwise. The reaction was then carried out at -70 °C for 30 min. The temperature of the reaction system was lowered to -70 °C, and a tetrahydrofuran solution of SM-4 (5.2 g) (16 mL) was added dropwise, followed by natural reaction for 1 h. The reaction was quenched with water, and the mixture was extracted three times with ethyl acetate. The combined organic phases were concentrated to dryness and recrystallized from dichloromethane / petroleum ether to obtain 14 g of intermediate M001-3. The molecular ion mass determined by mass spectrometry was 942.4263 (theoretical value: 941.3173).

[0177] (4) Synthesis of intermediate M001-4:

[0178] Intermediate M001-3 (14 g), glacial acetic acid (AcOH) (280 mL), and concentrated hydrochloric acid (con.HCl) (14 mL) were added to a 500 mL three-necked flask. The mixture was purged with nitrogen three times, and the reaction solution was heated to 100 °C and reacted for 12 h. The reaction solution was then cooled to room temperature, water was added dropwise, and the mixture was filtered and dried. Recrystallization from dichloromethane / ethanol yielded 12 g of intermediate M001-4. The molecular ion mass determined by mass spectrometry was 924.5236 (theoretical value: 923.3067).

[0179] (5) Synthesis of target product M001:

[0180] Intermediate M001-4 (11 g) was added to a 500 mL three-necked flask, followed by xylene (220 mL). The mixture was purged with nitrogen three times, and the reaction system was cooled to -40 °C. Tert-butyllithium t-BuLi (18.6 mL, 1.6 M concentration) was added dropwise, and the temperature was raised to 55 °C for 2 h. The reaction system was then cooled to -70 °C, and boron tribromide (3.45 mL) was added. The temperature was then raised to 55 °C for 1.5 h. The system was then cooled to -40 °C, and N,N-diisopropylethylamine DIEA (9.9 mL) was added. Finally, the reaction system was heated to 110 °C for 5 h. After cooling to room temperature, methanol was added dropwise and stirred for 30 min. The mixture was filtered, dried, and recrystallized from dichloromethane / methanol to obtain 1.7 g of solid, which was the target product M001. The molecular ion mass determined by mass spectrometry was 898.6522 (theoretical value: 897.3315).

[0181] Synthesis Examples 2-5: The process route is the same as that of Synthesis Example 1, except that the raw materials used are different. The raw materials, target products and result characterization data are shown in the table below, where "Ph" represents phenyl.

[0182]

[0183]

[0184] Horizontal luminous dipole ratio test

[0185] Angle-resolved photoluminescence (ARPR) measurement was performed using a Fuxing Chemical / R1-OLED angle-resolved spectrometer. The organic compounds to be tested were doped into the host thin film, and the results are shown in Table 1. The structures of the comparative compounds in Table 1 are as follows:

[0186]

[0187] Table 1

[0188] PH-61:PH-3(50 / 50,w / w) M001 0.8 83.54 PH-61:PH-3(50 / 50,w / w) M015 0.8 83.25 PH-61:PH-3(50 / 50,w / w) M026 0.8 82.98 PH-61:PH-3(50 / 50,w / w) M034 0.8 83.02 PH-61:PH-3(50 / 50,w / w) Ref-1 0.8 74.67 PH-61:PH-3(50 / 50,w / w) Ref-2 0.8 73.42

[0189] As shown in Table 1, the proportion of horizontal luminescent dipoles in the organic compound provided by this invention is significantly higher than that in Ref-1 and Ref-2. The compound of this invention has a benzene ring linked at the 3 and 6 positions of carbazole. This biphenyl structure can significantly improve the proportion of horizontal luminescent dipoles in the compound, thereby improving the EQE (external quantum efficiency) of the material in the device.

[0190] The following will use several embodiments as examples to describe in detail the specific structure and preparation method of the organic compound and organic electroluminescent device of the present invention, but the organic compound and organic electroluminescent device of the present invention are not limited to these embodiments.

[0191] Example 1

[0192] An organic electroluminescent device includes 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 sequentially. The fabrication method of this organic electroluminescent device is as follows:

[0193] (1) The glass substrate coated with ITO transparent conductive layer was ultrasonically treated in commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in acetone / ethanol mixed solvent, baked in a clean environment until the moisture was completely removed, cleaned with ultraviolet light and ozone, and bombarded with low-energy cation beam.

[0194] (2) Place the glass substrate with the anode into a vacuum chamber and evacuate it to 1×10⁻⁶. -5 Pa, a mixture of HT-4:HI-3 (97 / 3, w / w) was vacuum-deposited on the above-mentioned anodic layer as a hole injection layer, and the thickness of the deposited film was 10 nm.

[0195] (3) A 60 nm layer of compound HT-4 was vacuum-deposited on the hole injection layer as a hole transport layer;

[0196] (4) A 5 nm layer of compound HT-39 was vacuum-deposited on the hole transport layer as an electron blocking layer;

[0197] (5) A light-emitting layer is vacuum-deposited on the electron blocking layer. The light-emitting layer includes a host material, a sensitizer, and a dopant material (fluorescent dye). The doping ratio is adjusted by adjusting the evaporation rate of each material using a multi-source co-evaporation method. The total film thickness is 40 nm. Specifically, phosphorus sensitization luminescence technology is used. The ratio of host material, phosphorus sensitizer, and dopant material is 94.2:5:0.8 (w / w / w). The host material is a PH-61:PH-3 (50 / 50, w / w) mixed host. The phosphorus sensitizer is GPD-29. The fluorescent dye is the organic compound M001 provided by this invention.

[0198] (6) A compound ET-23 with a thickness of 5 nm was vacuum-deposited on the light-emitting layer as a hole blocking layer;

[0199] (7) A mixture of compound ET-69:ET-57 (50 / 50, w / w) was vacuum-deposited on the hole blocking layer as an electron transport layer, with a total film thickness of 25 nm.

[0200] (8) A 1 nm thick LiF layer was vacuum-deposited on the electron transport layer as an electron injection layer;

[0201] (9) An Al layer with a thickness of 150 nm is vacuum-deposited on the electron injection layer as the cathode of the device to obtain the organic electroluminescent device; the total deposition rate of all organic layers and LiF is controlled at 0.1 nm / s, and the deposition rate of the metal electrode is controlled at 1 nm / s.

[0202] Examples 2-9, Comparative Examples 1-2

[0203] An organic electroluminescent device, which differs from Example 1 only in that the fluorescent dyes of the light-emitting layer are the compounds shown in Table 2; the other layers, thicknesses, materials and preparation methods are the same as in Example 1.

[0204] The structures of the fluorescent dyes in Comparative Examples 1-2 are as follows:

[0205]

[0206] Device performance testing:

[0207] Under the same brightness, the driving voltage, lifetime, and external quantum efficiency of each organic electroluminescent device were measured using a digital source meter and luminance meter. Specifically, the voltage was increased at a rate of 0.1 V per second, and the current density of the organic electroluminescent device was measured when it reached 10 mA / cm². 2 The voltage at that time is the driving voltage, and the luminous intensity and external quantum efficiency (EQE, %) at that time are measured simultaneously.

[0208] FWHM is 10mA / cm 2 The full width at half maximum (FWHM) of the electroluminescence spectrum peak at the given current density.

[0209] The test results are shown in Table 2:

[0210] Table 2

[0211]

[0212]

[0213] As can be seen from the performance data in Table 2, compared with Comparative Examples 1-2, the organic compound provided by the present invention, as a fluorescent dye for organic electroluminescent devices, has obvious advantages in electroluminescence performance due to its specific molecular structure. It has excellent photoelectric properties, narrow spectral characteristics and stability, and can effectively improve the external quantum efficiency of the device. It is a high-performance green light emitting material.

[0214] The applicant declares that this invention illustrates the organic compounds and their applications, as well as organic electroluminescent devices, through the above embodiments. However, this invention is not limited to the above embodiments, meaning that this invention does not necessarily rely on the above embodiments for implementation. Those skilled in the art should understand that any improvements to this invention, equivalent substitutions of raw materials for the products of this invention, additions of auxiliary components, and selection of specific methods all fall within the protection and disclosure scope of this invention.

Claims

1. An organic compound, characterized in that, The organic compound has the structure shown in Formula I: Ar1, Ar2, Ar3, and Ar4 are each independently selected from any one of substituted or unsubstituted C6-C60 aryl groups or substituted or unsubstituted C3-C60 heteroaryl groups; R1 represents no substitution, single substitution, and the maximum permissible substitution. R1 is selected from hydrogen, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C6-C30 arylsilyl, substituted or unsubstituted C6-C30 heteroarylsilyl, substituted or unsubstituted C1-C20 alkylamino, etc. The R1 may be any one of the following: substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C60 aryl, or substituted or unsubstituted C3-C60 heteroaryl; at least two adjacent groups in R1 are not connected to each other or are linked to form a ring by chemical bonds; R1 is not connected to adjacent ring structures or is linked to form a ring by chemical bonds. Dashed lines represent single bonds or no connection; m1 and m2 are each independently 0 or 1; X1 and X2 are each independently selected from any one of the following: single bond, O, S, NR4, CR5R5' or SiR6R6'; Y is selected from any one of single bond, O, S, CR7R7' or SiR8R8'; R4, R5, R5', R6, R6', R7, R7', R8, and R8' are each independently selected from any one of the following: substituted or unsubstituted C1-C20 straight-chain or branched alkyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, substituted or unsubstituted C2-C20 alkenyl groups, substituted or unsubstituted C6-C60 aryl groups, and substituted or unsubstituted C3-C60 heteroaryl groups; R5 and R5' are not connected or are linked by chemical bonds to form a ring; R6 and R6' are not connected or are linked by chemical bonds to form a ring; R7 and R7' are not connected or are linked by chemical bonds to form a ring; and R8 and R8' are not connected or are linked by chemical bonds to form a ring. Ring A and ring B are each independently selected from any one of substituted or unsubstituted C6-C60 aromatic rings or substituted or unsubstituted C3-C60 heteroaromatic rings; The substituents described in Ar1, Ar2, Ar3, Ar4, cycloA, cycloB, R1, R4, R5, R5', R6, R6', R7, R7', R8, and R8' are each independently selected from halogens, unsubstituted or R'-substituted C1-C20 straight-chain or branched alkyl groups, unsubstituted or R'-substituted C3-C20 cycloalkyl groups, unsubstituted or R'-substituted C1-C20 alkoxy groups, unsubstituted or R'-substituted C2-C20 alkenyl groups, unsubstituted or R'-substituted C1-C20 alkylsilyl groups, unsubstituted or R'-substituted C1-C20 alkylamino groups, unsubstituted or R'-substituted C6-C30 arylsilyl groups, and unsubstituted or R'-substituted... The substituted C6-C30 heteroarylsilyl, 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; each of the substituted substituents is independently not connected to or is linked to an adjacent ring structure by a chemical bond to form a ring, and at least two adjacent groups of the substituted substituents are not connected to or are linked to each other by a chemical bond to form a ring; Each R' is independently selected from any one or a combination of at least two of the following: halogen, cyano, nitro, hydroxyl, amino, C1-C20 straight-chain or branched alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C30 arylsilyl, C6-C30 heteroarylsilyl, C6-C60 aryl, and C3-C60 heteroaryl; at least two adjacent R's are not connected or are linked by chemical bonds to form a ring; the R's are not connected to adjacent ring structures or are linked by chemical bonds to form a ring.

2. The organic compound according to claim 1, characterized in that, The organic compound has the structure shown in Formula II: Among them, Ar1, Ar2, Ar3, Ar4, X1, X2, Y, ring A, ring B, R1, m1 and m2 have the same limited range as in Equation I.

3. The organic compound according to claim 2, characterized in that, The organic compound has the structure shown in Formula III: Among them, Ar1, Ar2, Ar3, Ar4, X1, X2, Y, ring A, ring B, R1, m1 and m2 have the same limited range as in Equation I; R2 and R3 independently represent no substitution, single substitution, and the maximum permissible substitution. R2 and R3 are each independently selected from hydrogen, halogen, unsubstituted or R'-substituted C1-C20 straight-chain or branched alkyl groups, unsubstituted or R'-substituted C3-C20 cycloalkyl groups, unsubstituted or R'-substituted C1-C20 alkoxy groups, unsubstituted or R'-substituted C2-C20 alkenyl groups, unsubstituted or R'-substituted C1-C20 alkylsilyl groups, unsubstituted or R'-substituted C1-C20 alkylamino groups, unsubstituted or R'-substituted C6-C30 arylsilyl groups, unsubstituted or R'-substituted C6-C30 heteroarylsilyl groups, cyano, nitro, hydroxy, and amino groups. The R2 and R3 groups are any one of the following: arylamine, 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; at least two adjacent groups in R2 and R3 are not connected to each other or are linked to form a ring by chemical bonds; R2 and R3 are not connected to adjacent ring structures or are linked to form a ring by chemical bonds.

4. The organic compound according to claim 3, characterized in that, The organic compound has the structure shown in Formula IV: Ar1, Ar2, R1, R2, and R3 have the same defined range as in Equation III; R A1 and R A2 Each can be used independently to represent no substitution, single substitution, or the maximum permissible substitution. R A1 R A2 Each is independently selected from hydrogen, halogen, unsubstituted or R'-substituted C1-C20 straight-chain or branched alkyl, unsubstituted or R'-substituted C3-C20 cycloalkyl, unsubstituted or R'-substituted C1-C20 alkoxy, unsubstituted or R'-substituted C2-C20 alkenyl, unsubstituted or R'-substituted C1-C20 alkylsilyl, unsubstituted or R'-substituted C1-C20 alkylamino, unsubstituted or R'-substituted C6-C30 arylsilyl, unsubstituted or Any one of the following: R'-substituted C6-C30 heteroarylsilyl, 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; unsubstituted or R'-substituted C3-C60 heteroaryl; wherein R A1 R A2 In the presence of at least two adjacent groups, they are either not connected or are linked by chemical bonds to form a ring; the R A1 R A2 Each ring is independent and not connected to the adjacent ring structure or is connected to form a ring by chemical bonds.

5. The organic compound according to any one of claims 1-4, characterized in that, Ar1 and Ar2 are each independently selected from any one of substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C3-C30 heteroaryl groups, preferably any one of the following groups: phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthryl, and more preferably substituted or unsubstituted phenyl or substituted or unsubstituted biphenyl. Preferably, the substituents in Ar1 and Ar2 are each independently selected from any one of halogen, cyano, unsubstituted or R'-substituted C1-C10 straight-chain or branched alkyl, unsubstituted or R'-substituted C3-C10 cycloalkyl, unsubstituted or R'-substituted C2-C10 alkenyl, unsubstituted or R'-substituted C1-C10 alkylsilyl, unsubstituted or R'-substituted C6-C20 aryl, and unsubstituted or R'-substituted C3-C20 heteroaryl. More preferably, halogen, cyano, unsubstituted or halogenated C1-C10 straight-chain or branched alkyl, C1-C10 alkylsilyl, and C6-C18 aryl.

6. The organic compound according to any one of claims 1-4, characterized in that, Ar1 and Ar2 are each independently selected from any one of the following groups: More preferably, Ar1 and Ar2 are each independently selected from any one of the following groups: -* represents the linking site of a functional group.

7. The organic compound according to any one of claims 1-4, characterized in that, R1 is selected from any one of hydrogen, halogen, cyano, substituted or unsubstituted C1-C10 straight-chain or branched alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C1-C10 alkylsilyl, substituted or unsubstituted C6-C20 aryl, and substituted or unsubstituted C3-C20 heteroaryl, preferably hydrogen, halogen, or any one of the following groups: C1-C6 straight-chain or branched alkyl, C1-C10 alkylsilyl, phenyl, biphenyl, terphenyl, naphthyl, anthraceneyl, and phenanthrene; Preferably, R1 represents unsubstituted or monosubstituted, and in the case of monosubstituted R1, the linkage site on the benzene ring is the para position of the N-linked site.

8. The organic compound according to claim 4, characterized in that, The R A1 R A2 Each group is independently selected from any one of hydrogen, halogen, cyano, unsubstituted or R'-substituted C1-C10 straight-chain or branched alkyl, unsubstituted or R'-substituted C3-C10 cycloalkyl, unsubstituted or R'-substituted C2-C10 alkenyl, unsubstituted or R'-substituted C1-C10 alkylsilyl, unsubstituted or R'-substituted C6-C20 aryl, and unsubstituted or R'-substituted C3-C20 heteroaryl. Preferably, hydrogen, halogen, or unsubstituted or R'-substituted groups are selected from any one of the following groups: C1-C6 straight-chain or branched alkyl, C1-C10 alkylsilyl, phenyl, biphenyl, terphenyl, naphthyl, anthraceneyl, and phenanthrene.

9. The organic compound according to claim 1, characterized in that, The organic compound has a structure shown in any of the following:

10. The use of an organic compound as described in any one of claims 1-9, characterized in that, The organic compounds are used in organic electronic devices; Preferably, the organic electronic device includes an organic electroluminescent device; Preferably, the organic compound is used as a light-emitting layer material in an organic electroluminescent device.

11. An organic electroluminescent device, characterized in that, The organic electroluminescent device includes a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode; the organic layer includes at least one organic compound as described in any one of claims 1-9; Preferably, the organic layer includes a light-emitting layer, wherein the light-emitting layer includes at least one organic compound as described in any one of claims 1-9; Preferably, the light-emitting layer comprises a host material and a dopant material, wherein the dopant material comprises at least one organic compound as described in any one of claims 1-9; Preferably, the light-emitting layer further includes a sensitizer; Preferably, the sensitizer includes any one or a combination of at least two of thermally activated delayed fluorescence materials and phosphorescent materials.

12. A display device, characterized in that, The display device includes the organic electroluminescent device as described in claim 11.

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