A compound and application thereof, an organic electroluminescent device comprising the same

Abstract

This invention provides an organic compound and its application. The organic compound has the structure shown in formula (1). The compound of this invention forms an ortho-substitution through a phenylene structure, which is beneficial to reducing the sublimation temperature and improving the stability of the material during the evaporation process. The color is adjusted through M1. Compared with increasing the conjugation or introducing strong donor and acceptor groups, this approach does not cause the compound to broaden its half-peak width, which is beneficial to obtaining better color purity. The compound of this invention has a low triplet energy level, which suppresses the reverse gap jump and improves the device lifetime decay caused by the high-energy, long-lifetime excited triplet state of the parent core structure, which is beneficial to the device lifetime.

Description

Technical Field

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

[0002] In recent years, optoelectronic devices based on organic materials have become increasingly popular. The inherent flexibility of organic materials makes them ideal for fabrication on flexible substrates, allowing for the design and production of aesthetically pleasing and stylish optoelectronic products, offering unparalleled advantages over inorganic materials. Examples of such organic optoelectronic devices include organic light-emitting diodes (OLEDs), organic field-effect transistors, organic photovoltaic cells, and organic sensors. OLEDs, in particular, have developed rapidly and have already achieved commercial success in the information display field. OLEDs can provide highly saturated red, green, and blue colors, and full-color displays made with them do not require an additional backlight, offering advantages such as vibrant colors, thinness, and flexibility.

[0003] The core of an OLED device is a thin-film structure containing various organic functional materials. Common functionalized organic materials include: hole injection materials, hole transport materials, hole blocking materials, electron injection materials, electron transport materials, electron blocking materials, as well as light-emitting host materials and light-emitting guest materials (dyes). When an electric current is applied, electrons and holes are injected and transported to the light-emitting region, where they recombine, thereby generating excitons and emitting light.

[0004] Various organic materials have been developed and, combined with specially designed device structures, can improve carrier mobility, regulate carrier balance, break through electroluminescence efficiency, and delay device decay. For quantum mechanical reasons, common fluorescent emitters primarily utilize 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, can simultaneously utilize triplet and singlet excitons to emit light, and are called phosphorescent emitters, with energy conversion efficiencies up to four times higher than traditional fluorescent emitters. Thermally excited delayed fluorescence (TADF) technology promotes intersystem crossing from triplet to singlet excitons, effectively utilizing triplet excitons to achieve high luminescence efficiency without the use of metal complexes. Thermally excited sensitized fluorescence (TASF) technology uses materials with TADF properties to sensitize the emitter through energy transfer, also achieving high luminescence efficiency.

[0005] As OLED products gradually enter the market, people have increasingly higher requirements for their performance. For example, the BT-2020 color gamut standard, which meets the image signals of the 4K and 8K era, has a significantly larger color gamut coverage than the existing DCI-P3 color gamut standard. The demand for red, green, and blue colors has also increased accordingly, especially for green light, where the chromaticity has improved from the original CIE (0.265, 0.690) to CIE (0.170, 0.797). However, in currently commercially available OLED materials, green light-emitting materials use phosphorescent materials with a wide half-width and strong shoulder peaks at longer wavelengths, making it difficult to simultaneously meet the requirements of high efficiency, long lifespan, and excellent color purity. To solve this problem, 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 lifespan, and high color purity. Furthermore, the amount of phosphorescent material used can be significantly reduced through sensitization technology, thereby reducing the cost of OLEDs. This technology has great advantages and potential in realizing BT.2020 displays.

[0006] Since their discovery, boron compounds with multiple resonance structures have been a research hotspot for fluorescent luminescent materials. Their narrow spectrum, high fluorescence quantum efficiency, and easily tunable emission wavelength make them suitable for use in sensitized fluorescence technology, enabling the fabrication of devices with high efficiency and narrow half-peak emission. However, these materials have low energy levels in the lowest singlet and lowest triplet states, exhibiting thermally activated delayed fluorescence properties. Their delayed fluorescence lifetimes are in the tens or even hundreds of microseconds (CN114437121A)([1]Multi-Resonance Induced Thermally Activated Delayed Fluorophores for Narrowband Green OLEDs[J].Angewandte Chemie International Edition,2019,58(47)). When these materials are used as luminescent materials in sensitization technology, their device lifetimes are often short, making it impossible to achieve mass production applications.

[0007] Therefore, developing more types of organic narrow-spectrum luminescent materials with better electroluminescence properties is one of the key issues in achieving the above-mentioned expectations. Summary of the Invention

[0008] To address the shortcomings of existing technologies, the present invention aims to provide a compound and its application, as well as an organic electroluminescent device containing the compound. The compound achieves the purpose of adjusting the light color by introducing M1 (cyclization) without causing broadening of the full width at half maximum (FWHM) or reduction of the LUMO energy level. With the addition of low T1 energy level groups, the lifetime is improved. Using this type of compound in OLED light-emitting materials is expected to achieve higher color purity and device lifetime.

[0009] To achieve this objective, the present invention adopts the following technical solution:

[0010] An organic compound, characterized in that the organic compound has the structure shown in formula (1):

[0011]

[0012] In equation (1), X is independently one of O, S, Se, NR1, CR2R3, and SiR4R5;

[0013] M1 is independently represented by O, S, Se, and NR. 21 CR 22 R 23 SiR 24 R 25 One of them;

[0014] X 1 X 2 X 3 X 4 X 5 X 6 X 7 X 8 Each independently selected from CR A1 Or N;

[0015] Y 1 Y 2 Y 3 Y 4 Each independently selected from CR A2 Or N;

[0016] Z 1 Z 2 Each independently selected from CR A3 Or N;

[0017] X 4 With X 5 They are either not connected to each other or linked together by chemical bonds to form a ring;

[0018] R1, R2, R3, R4, R5, R 21 R 22 R 23 R 24R 25 Each of the following is independently selected from any one of unsubstituted or R'-substituted C1-C20 straight-chain or branched alkyl groups, unsubstituted or R'-substituted C2-C20 alkenyl groups, unsubstituted or R'-substituted C3-C20 cycloalkyl groups, unsubstituted or R'-substituted C6-C60 aryl groups, and unsubstituted or R'-substituted C3-C60 heteroaryl groups; R2 and R3 are not connected or are linked into a ring by chemical bonds; R4 and R5 are not connected or are linked into a ring by chemical bonds; R 22 With R 23 The R are either not connected or linked by chemical bonds to form a ring; 24 With R 25 They are either not connected to each other or linked together by chemical bonds to form a ring;

[0019] R A1 R A2 R A3 Each is independently selected from hydrogen, halogen, cyano, nitro, amino, hydroxyl, unsubstituted or R'-substituted C1-C20 straight-chain 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 C6-C30 arylsilyl, unsubstituted or R'-substituted One of the following: C2-C30 heteroarylsilyl, unsubstituted or R'-substituted C1-C20 alkylamino, 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;

[0020] The R A1 R A2 R A3 Each is independently independent of its adjacent ring structure or connected to form a ring through chemical bonds, and the adjacent R A1 R A2 R A3 They are either not connected to each other or linked together by chemical bonds to form a ring;

[0021] And the R A1 R A2 R A3 R1, R2, R3, R4, R5, R 21 R 22 R 23 R 24 R 25 Or at least one of R' is the structure shown in equation (a);

[0022] In formula (a), L is selected from one of unsubstituted or R”-substituted C6-C60 arylene or unsubstituted or R”-substituted C3-C60 heteroarylene;

[0023] X 11 X 12 X 13 X 14 X 15 X 16 X 17 X 18 Each is independently selected from C and CR C1 It can be one of N, and one of them is C, wherein C is connected to L;

[0024] The R C1 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 C2-C20 alkenyl, unsubstituted or R”-substituted C1-C20 alkoxy, unsubstituted or R”-substituted C1-C20 alkylsilyl, unsubstituted or R”-substituted C6-C30 arylsilyl, unsubstituted or R”-substituted C2-C30 heteroarylsilyl, unsubstituted or Any one of the following: R”-substituted C1-C20 alkylamino, cyano, nitro, amino, hydroxyl, 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; two adjacent R C1 They are either not connected or linked by chemical bonds to form a ring; R C1 Each R is independent and not connected to adjacent ring structures or is connected to form a ring by chemical bonds. Any two adjacent R C1 At least one group of the rings are connected by chemical bonds to form a ring G, wherein the ring G is selected from any one of unsubstituted or R'-substituted C3-C60 aromatic rings and unsubstituted or R'-substituted C3-C60 heteroaromatic rings;

[0025] Each of R' and R” is independently selected from any one or a combination of at least two of halogen, cyano, nitro, hydroxy, amino, C1-C20 straight-chain or branched-chain alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylsilyl, C2-C30 heteroarylsilyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C30 aryl, and C3-C60 heteroaryl, or R' has the structure shown in formula a, and each of R' and R” is independently not connected to the adjacent ring structure or forms a ring through a chemical bond, and adjacent R' or R” are not connected or form a ring through a chemical bond.

[0026] In the present invention, the group of "unsubstituted or R'-substituted" may be substituted with one substituent R' or may be substituted with multiple substituents R'. When there are multiple (at least 2) substituents R', they may be the same or different substituents; when the same expression is involved hereinafter, it has the same meaning. Unless otherwise specified, the selection range of R' is as shown above and will not be elaborated further.

[0027] It should be noted that in the present invention, for the convenience of description, the possible functions of each group / feature are described separately, but this does not mean that these groups / features act independently. 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 between various groups, rather than the effect of a single group / feature.

[0028] The following are the preferred technical solutions of the present invention, but they do not 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.

[0029] In the present invention, the halogen may all be fluorine, chlorine, bromine or iodine. When the same description is involved hereinafter, it has the same meaning.

[0030] In the present invention, for the description of chemical elements, unless otherwise specified, the concept of isotopes with the same chemical properties is included. For example, hydrogen (H) includes 1 H (protium), 2 H (deuterium, D), 3 H (tritium, T), etc.; carbon (C) includes 12 C, 13 C, etc.

[0031] In the present invention, the hydrogen at any position on the organic compound having the structure shown in formula I may optionally be substituted with deuterium.

[0032] 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.

[0033] 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.

[0034] In this invention, "-*" and "*" both represent the linking site of a group.

[0035] 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.

[0036] In this invention, "each independently" means that when there are multiple subjects, they can be the same or different from each other.

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

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

[0039] 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.

[0040] C3-C20 can all be C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.

[0041] 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.

[0042] 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.

[0043] 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.

[0044] In this invention, the C6-C60 aryl group, preferably C6-C30 aryl group (C6-C30 aromatic ring), includes monocyclic aryl and fused-ring aryl groups; 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 linked by single bonds, including but not limited to: phenyl, biphenyl, terphenyl, tetraphenyl, etc.; the fused-ring aryl group means that the group contains at least two rings (and at least one ring is an aromatic ring), and the rings are connected by a single bond. A group consisting of two adjacent carbon atoms fused together, exemplary examples include but are 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, acenaphthyl, benzo[a]acenaphthyl, etc. It should be noted that monocyclic aryl and fused-ring aryl groups linked by single bonds also fall under the aryl group category, such as phenylnaphthyl, naphthylphenyl, binaphthyl, phenylnaphthylphenyl, etc.

[0045] The C3-C60 heteroaryl group, 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, bipyridyl, 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, phenothiazinyl, 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, diphenylpyridinyl, diphenylpyrimidinyl, etc.

[0046] 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.

[0047] In this invention, specific examples of the C6-C30 arylamino group are monovalent groups obtained by substituting at least one hydrogen atom in the -NH2 group with the aforementioned aryl group, including but not limited to: phenylamino, methylphenylamino, naphthylamino, anthraceneylamino, phenanthreneamino, biphenylamino, etc. Specific examples of the C3-C30 heteroarylamino group are monovalent groups obtained by substituting at least one hydrogen atom in the -NH2 group with the aforementioned heteroaryl group, including but not limited to: pyridinylamino, pyrimidinylamino, dibenzofuranylamino, etc.

[0048] 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.

[0049] In this invention, 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, 2-methylbutyl, n-pentyl, isopentyl, neopentyl, n-hexyl, neohexyl, 2-ethylhexyl, n-octyl, n-heptyl, n-nonyl, n-decyl, etc.

[0050] 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.

[0051] A specific example of the C1-C20 alkylsilyl group is a monovalent group obtained by replacing at least one hydrogen in -SiH3 with the above-mentioned straight-chain or branched alkyl group; a specific example of the C1-C20 alkylamino group is a monovalent group obtained by replacing at least one hydrogen in -NH2 with the above-mentioned straight-chain or branched alkyl group.

[0052] 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.

[0053] 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.

[0054] Preferably, the organic compound has the structure shown in formula (2-1):

[0055]

[0056] In equation (2-1), X 1 X 2 X 3 X 6 X 7 X 8 Y 1 Y 2 Y 3 Y 4 Z 1 Z 2 The definition of M1 is the same as the definition in equation (1);

[0057] M2 consists independently of carbon-carbon single bonds, O, S, Se, and NR. 31CR 32 R 33 Si R 34 R 35 One of them;

[0058] R 31 R 32 R 33 R 34 R 35 Each is independently selected from any one of unsubstituted or R'-substituted C1-C20 straight-chain or branched alkyl groups, unsubstituted or R'-substituted C3-C20 cycloalkyl groups, unsubstituted or R'-substituted C2-C20 alkenyl groups, unsubstituted or R'-substituted C6-C60 aryl groups, and unsubstituted or R'-substituted C3-C60 heteroaryl groups; wherein the R 32 With R 33 The R are either not connected or linked by chemical bonds to form a ring; 34 With R 35 They are either not connected to each other or are linked together by chemical bonds to form a ring.

[0059] Preferably, X is independently one of O, S, NR1, CR2R3, and SiR4R5;

[0060] Preferably, X is independently one of O, S, and NR1;

[0061] Preferably, X is independently one of O and NR1;

[0062] Preferably, the organic compound has the structure shown in formula (2-1-1) or formula (2-1-2):

[0063]

[0064] In equations (2-1-1) and (2-1-2), X 1 X 2 X 3 X 6 X 7 X 8 Y 1 Y 2 Y 3 Y 4 Z 1 Z 2 The definition range of M1 is the same as that in equation (1); the definition range of M2 is the same as that in equation (2-1);

[0065] R1 is independently selected from any one of the following: unsubstituted or R'-substituted C1-C10 straight-chain or branched alkyl, unsubstituted or R'-substituted C2-C20 alkenyl, unsubstituted or R'-substituted C3-C10 cycloalkyl, unsubstituted or R'-substituted C6-C30 aryl, and unsubstituted or R'-substituted C3-C30 heteroaryl.

[0066] Preferably, the organic compound has the structure shown in formula (2-1-1), formula (2-1-2-1), or formula (2-1-2-2):

[0067]

[0068] In equations (2-1-1), (2-1-2-1), and (2-1-2-2), X 1 X 2 X 3 X 6 X 7 X 8 Y 1 Y 2 Y 3 Y 4 Z 1 Z 2 The definition range of M1 is the same as that in equation (1); the definition range of M2 is the same as that in equation (2-1);

[0069] Y 5 Y 6 Y 7 Y 8 Y 9 Each R' is independently selected from one of CR' or N, and each R' is independently selected from one or a combination of two of the following: halogen, cyano, amino, C1-C20 straight-chain or branched alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylsilyl, C2-C30 heteroarylsilyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl, or R' has the structure shown in formula a; each R' is independently not connected to the adjacent ring structure or is connected to form a ring by a chemical bond, and adjacent R's are not connected to each other or are connected to form a ring by a chemical bond;

[0070] Ra1 and Ra2 are each independently selected from one or a combination of two of the following: halogen, cyano, amino, C1-C20 straight-chain or branched alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylsilyl, C2-C30 heteroarylsilyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl, or have the structure shown in Formula a; Ra1 and Ra2 are each independently not connected to adjacent ring structures or are connected to each other by chemical bonds to form a ring; Ra1 and Ra2 are not connected to each other or are connected to each other by chemical bonds to form a ring.

[0071] Preferably, in formula (2-1-2-1) Y 4 With Y 5 They are either not connected or connected in a loop;

[0072] Preferably, the organic compound has the structure shown in formula (2-1-1), formula (2-1-2-2), formula (2-1-2-1-1), or formula (2-1-2-1-2):

[0073]

[0074]

[0075] In this context, dashed lines represent single keys or no connection.

[0076] X 1 X 2 X 3 X 6 X 7 X 8 Y 1 Y 2 Y 3 Y 4 Z 1 Z 2 The definition range of M1 is the same as that in equation (1); the definition range of M2 is the same as that in equation (2-1); Y 5 Y 6 Y 7 Y 8 Y 9 The definition range is the same as the definition range in equation (2-1-2-1); the definition ranges of Ra1 and Ra2 are the same as the definition ranges in equation (2-1-2-2);

[0077] M3 is independently represented by O, S, Se, and NR. 41 CR 42 R43 Si R 44 R 45 One of them;

[0078] R 41 R 42 R 43 R 44 R 45 Each is independently selected from any one of unsubstituted or R'-substituted C1-C20 straight-chain or branched alkyl groups, unsubstituted or R'-substituted C3-C20 cycloalkyl groups, unsubstituted or R'-substituted C2-C20 alkenyl groups, unsubstituted or R'-substituted C6-C60 aryl groups, and unsubstituted or R'-substituted C3-C60 heteroaryl groups; wherein the R 42 With R 43 The R are either not connected or linked by chemical bonds to form a ring; 44 With R 45 They are either not connected to each other or linked together by chemical bonds to form a ring;

[0079] Preferably, X is independent of NR1.

[0080] Preferably, M2 is independently a carbon-carbon single bond, O, S, Se, or NR. 31 CR 32 R 33 SiR 34 R 35 One of them;

[0081] Preferably, the organic compound has the structure shown in formula (3-1), formula (3-2), or formula (3-3):

[0082]

[0083] In equation (3-2), Y 4 With Y 5 They are either not connected or connected in a loop;

[0084] X 1 X 2 X 3 X 6 X 7 X 8 Y 1 Y 2 Y 3 Y 4 Z 1 Z 2 The definition range of M1 is the same as the definition range in equation (1); Y 5 Y 6 Y 7 Y 8 Y9 The definition range is the same as the definition range in equation (2-1-2-1); the definition ranges of Ra1 and Ra2 are the same as the definition ranges in equation (2-1-2-2).

[0085] Preferably, M1 is independently O, S, NR. 21 CR 22 R 23 SiR 24 R 25 One of them;

[0086] Preferably, M1 is independently O and NR. 21 CR 22 R 23 SiR 24 R 25 One of them;

[0087] Preferably, M1 is independently O and CR 22 R 23 SiR 24 R 25 One of them;

[0088] Preferably, M1 is independently O or CR. 22 R 23 ;

[0089] Preferably, M1 is independently CR 22 R 23 ;

[0090] Preferably, it has a structure shown in any of formulas (4-1), (4-2), (4-3), (4-4), (4-5), or (4-6):

[0091]

[0092] Among them, X 1 X 2 X 3 X 6 X 7 X 8 Y 1 Y 2 Y 3 Y 4 The definition scope of is the same as that in equation (1); Y 5 Y 6 Y 7 Y 8 Y 9The definition range is the same as the definition range in equation (2-1-2-1); the definition ranges of Ra1 and Ra2 are the same as the definition ranges in equation (2-1-2-2); R 22 R 23 Each is independently selected from any one of unsubstituted or R'-substituted C1-C20 straight-chain or branched alkyl groups, unsubstituted or R'-substituted C2-C20 alkenyl groups, unsubstituted or R'-substituted C3-C20 cycloalkyl groups, unsubstituted or R'-substituted C6-C30 aryl groups, and unsubstituted or R'-substituted C3-C30 heteroaryl groups; wherein the R 22 With R 23 They are either not connected to each other or linked together by chemical bonds to form a ring;

[0093] Preferably, it has a structure shown in any of formulas (4-2), (4-3), (4-4), (4-5), or (4-6):

[0094] Preferably, it has the structure shown in formula (4-3), formula (4-4), or formula (4-6);

[0095] Preferably, it has the structure shown in formula (4-4) or formula (4-6).

[0096] Preferably, the organic compound has the structure shown in formula (4-3), formula (4-4-1), or formula (4-6-1):

[0097]

[0098] Rings E and F are selected from one of the following: R'-substituted or unsubstituted C6-C60 aromatic rings and R'-substituted or unsubstituted C2-C60 heteroaromatic rings;

[0099] M4 represents a carbon-carbon single bond, O, S, Se, NR. 51 CR 52 R 53 Si R 54 R 55 One of them;

[0100] R 51 R 52 R 53 R 54 R 55Each is independently selected from any one or at least a combination of 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-C30 arylsilyl, C2-C30 heteroarylsilyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl; The R 52 With R 53 The R are either not connected or linked by chemical bonds to form a ring; 54 With R 55 They are either not connected to each other or linked together by chemical bonds to form a ring;

[0101] m4 can be 0 or 1; m4 being 0 indicates that M4 does not exist.

[0102] Preferably, it has the structure shown in formula (4-3), formula (5-1), or formula (5-2):

[0103]

[0104] Among them, X 1 X 2 X 3 X 6 X 7 X 8 Y 1 Y 2 Y 3 Y 4 The scope of the definition is the same as that in equation (1); Y 5 Y 6 Y 7 Y 8 Y 9 The scope of its definition is the same as that defined in equation (2-1-2-1);

[0105] The definition of M4 is the same as that in equation (4-4-1);

[0106] X b1 X b2 X b3 X b4 X b5 X b6 X b7 X b8 Each independently selected from CR D1 Or any one of N;

[0107] The R D1Each is independently selected from one or a combination of two of the following: hydrogen, 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-C30 arylsilyl, C2-C30 heteroarylsilyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl; R D1 Each is independently independent of its adjacent ring structure or connected to form a ring through chemical bonds, and the adjacent R D1 They are either not connected to each other or linked together by chemical bonds to form a ring;

[0108] Preferably, it has the structure shown in formula (5-1-1) or formula (5-2-1):

[0109]

[0110] Preferably, M4 is a carbon-carbon single bond, O, or CR. 52 R 53 Si R 54 R 55 One of them may not exist;

[0111] Preferably, M4 is a carbon-carbon single bond or does not exist.

[0112] Preferably, formula (a) has any of the following structures:

[0113]

[0114]

[0115] Where -* represents the linking site of the group;

[0116] X 11 X 12 X 13 X 14 X 15 X 16 X 18 It has the same scope as in equation (a);

[0117] X 21 X 22 X 23 X 24 X 31 X 32 X 33 X 34 X 35 X 41 X42 X 43 X 44 X 45 X 46 X 51 X 52 X 53 X 54 Each is independently selected from either CR”' or N;

[0118] Each R”' is independently selected from any one or at least two combinations of hydrogen, halogen, cyano, nitro, hydroxyl, amino, C1-C20 straight-chain or branched alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C6-C30 arylsilyl, C3-C30 heteroarylsilyl, C1-C20 alkylamino, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl. Each R”' is independently not connected to the adjacent ring structure or is connected to form a ring by a chemical bond, and adjacent R”'s are not connected to each other or are connected to form a ring by a chemical bond.

[0119] Preferably, formula (a) is the structure shown in formula (a-1), formula (a-1-1), formula (a-2), formula (a-3), or formula (a-4-1):

[0120]

[0121] X 25 X 26 X 27 X 28 X 55 X 56 X 57 X 58 Each is independently selected from either CR”' or N;

[0122] Each R”' is independently selected from any one or at least two combinations of hydrogen, halogen, cyano, nitro, hydroxyl, amino, C1-C20 straight-chain or branched alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C6-C30 arylsilyl, C3-C30 heteroarylsilyl, C1-C20 alkylamino, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl. Each R”' is independently not connected to or is linked to an adjacent ring structure by a chemical bond to form a ring, and adjacent R”'s are not connected to or are linked to each other by a chemical bond to form a ring.

[0123] Preferably, X 11 X 12 X 13 X 14 X 15 X 16 X 18 X 21 X 22 X 23 X 24 X 31 X 32 X 33 X 34 X 35 X 41 X 42 X 43 X 44 X 45 X 46 X 51 X 52 X 53 X 54 X 25 X 26 X 27 X 28 X 55 X 56 X 57 X 58 Each is independently selected from CR”';

[0124] Preferably, formula (a) is the structure shown in formula (a-1) or formula (a-2);

[0125] Preferably, in formula (a), L is selected from one of unsubstituted or R”-substituted C6-C30 arylene and unsubstituted or R”-substituted C3-C30 heteroarylene;

[0126] Preferably, L is selected from one of phenylene, biphenylene, naphthylene, and pyridylene;

[0127] Preferably, the L is selected from any one of the following groups:

[0128]

[0129] Where -* represents the linking site of the group;

[0130] Y 11 Y 12 Y 13 Y 14 Each can be independently selected from either CR or N;

[0131] Each of R” is independently selected from any one or at least two combinations of hydrogen, halogen, cyano, nitro, hydroxyl, amino, C1-C20 straight-chain or branched alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C6-C30 arylsilyl, C3-C30 heteroarylsilyl, C1-C20 alkylamino, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl; each of R” is independently not connected to or is connected to an adjacent ring structure by a chemical bond to form a ring, and adjacent R” are not connected to or are connected to each other by a chemical bond to form a ring;

[0132] Preferably, L is selected from Any one of them,

[0133] Further optimization

[0134] Preferably, the Y 11 Y 12 Y 13 Y 14 Each is independently designated as a "CR";

[0135] Preferably, each of the R's is independently selected from hydrogen, C1-C20 straight-chain or branched alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C60 aryl, and C3-C60 heteroaryl;

[0136] Preferably, R A1 R A2 R A3 Or at least one of R' is the structure shown in equation (a);

[0137] Preferably, R A1 R A2 Or at least one of R' is the structure shown in equation (a);

[0138] Preferably, R A1 R A2 At least one of them is the structure shown in equation (a);

[0139] Preferably, X 2 or X 3 Y 2 Or Y 3 X 6 or X 7 One of them is the structure shown in equation (a).

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151] 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.

[0152] 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; more preferably, it is an organic electroluminescent device. Preferably, the organic compound is used in the organic electroluminescent device. Preferably, the organic compound serves as a light-emitting layer material in the organic electroluminescent device.

[0153] 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.

[0154] Preferably, the organic layer comprises at least one organic compound with a structure shown in M001-M240. Preferably, the organic layer comprises a light-emitting layer, which comprises at least one organic compound as described in the first aspect, and more preferably at least one organic compound with a structure shown in M001-M240. Preferably, the light-emitting layer comprises a host material and a dopant material, the dopant material comprising at least one organic compound as described in the first aspect.

[0155] More preferably, the organic compound provided by the present invention is used as a fluorescent dopant material for the light-emitting layer.

[0156] Fourthly, the present invention provides a display device comprising the organic electroluminescent device as described in the third aspect.

[0157] Compared with the prior art, the present invention has the following beneficial effects:

[0158] 1. Suitable sublimation temperature: Compared with the anthracene group being directly connected to the parent nucleus through carbon-carbon single bonds, the compound of this invention forms ortho-substitution through a phenylene structure, which is beneficial to reducing the sublimation temperature and improving the stability of the material during the vapor deposition process.

[0159] 2. While achieving color adjustment through M1, this invention does not cause the compound's half-peak width to broaden, compared to increasing conjugation or introducing strong donor-acceptor groups, and is beneficial for obtaining better color purity.

[0160] 3. The compound of the present invention has a low triplet energy level, which suppresses the reverse gap jump, improves the device lifetime decay caused by the high-energy long-lifetime triplet state of the parent core structure, and is beneficial to the device lifetime. Detailed Implementation

[0161] Synthesis Examples

[0162] The organic compounds represented by Formula I of 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.

[0163] In one specific embodiment, the organic compound has the structure shown in formula (5-1), and the compound can be prepared by the following synthetic route:

[0164]

[0165]

[0166] Hal1, Hal2, and Hal3 are selected from any one of I, Br, Cl, or F. When Hal1 is selected from Cl, Hal2 is preferably any one of I or Br, and Hal3 is preferably Br, I, or F. The atomic number of Hal3 is less than or equal to that of Hal2. When Hal1 is selected from Br, Hal2 is preferably I, and Hal3 is preferably I or F. n-BuLi represents n-butyllithium, and t-BuLi represents tert-butyllithium.

[0167] The specific preparation methods of the 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] It should be noted that obtaining the 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 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.

[0169] In the following synthesis examples of this invention, the molecular weight of intermediates and target products was determined using an Agilent HPLC-6500 series high-resolution Q-TOF liquid chromatography-mass spectrometry system, and the ionization source was an atmospheric pressure chemical ionization source (APCI source).

[0170] Synthesis Example 1: Synthesis of M001

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

[0172]

[0173] 12 g (1.0 eq) of 3,6-di-tert-butylcarbazole, 11.72 g (1.2 eq) of 1-bromo-3-chloro-2,4-difluorobenzene, and 20.99 g (1.5 eq) of cesium carbonate were weighed and placed in a 500 mL three-necked round-bottom flask. 240 mL of N,N-dimethylformamide (DMF) was added, and the mixture was heated to 80 °C for 24 h under a nitrogen atmosphere. The reaction progress was monitored by thin-layer chromatography (TLC). After the reaction was completed, the mixture was allowed to cool, and a large amount of water was added with stirring. A solid precipitated, which was filtered. The filter cake was washed with water and ethanol. After drying the filter cake, it was dissolved in dichloromethane, loaded onto silica gel, and subjected to silica gel column chromatography to obtain intermediate M001-1. The target molecular mass was determined by high-resolution mass spectrometry to be 798.2084 (APCI source, [M+H)). + (Theoretical value: 797.22);

[0174] (2) Synthesis of intermediate M001-2

[0175]

[0176] Weigh 10 g (1.0 eq) of M001-1, 11.9 g (1.05 eq) of RM-3, and 16.73 g (2.5 eq) of cesium carbonate into a 500 mL three-necked round-bottom flask, add 200 mL of DMF, and heat at 120 °C for 12 h under a nitrogen atmosphere. The reaction progress was monitored by thin-layer chromatography. After the reaction was complete, allow the mixture to cool, then add a large amount of water with stirring. A solid precipitated, was filtered, and the filter cake was washed with water and ethanol. After drying the filter cake, it was dissolved in dichloromethane, loaded onto silica gel, and subjected to silica gel column chromatography to obtain intermediate M001-2. High-resolution mass spectrometry (HPLC) analysis showed the target molecular mass to be 1017.2846 (APCI source, [M+H)). + (Theoretical value: 1016.34);

[0177] (3) Synthesis of intermediate M001-3

[0178]

[0179] 11.0 g (1.0 eq) of M001-2 was weighed and placed in a 500 mL three-necked round-bottom flask. 160 mL of ultra-dry tetrahydrofuran was added. Under a nitrogen atmosphere, the mixture was cooled to below -70 °C using a liquid nitrogen-ethanol mixture. Then, 5.18 mL (1.2 eq) of 2.5 M n-butyllithium solution was slowly added, and the reaction mixture was allowed to react at below -50 °C for 0.5 h. The mixture was then cooled again to below -70 °C using a liquid nitrogen-ethanol mixture. 2.53 g (1.3 eq) of RM-4 tetrahydrofuran solution was added, and the reaction mixture was allowed to slowly return to room temperature for 2 h. 15 mL of 1 mol / L dilute hydrochloric acid was added to quench the reaction. After concentration, the reaction mixture was purified by silica gel column chromatography to obtain intermediate M001-3. High-resolution mass spectrometry analysis revealed the target molecular mass to be 1119.4342 (APCI source, [M+H)). + Theoretical value: 1118.49.

[0180] (4) Synthesis of intermediate M001-4

[0181]

[0182] 8.0 g of M001-3 was weighed and placed in a 500 mL three-necked round-bottom flask. 100 mL of acetic acid and 5 mL of concentrated hydrochloric acid were added, and the mixture was heated at 110 °C for 12 hours under a nitrogen atmosphere. After the reaction was complete, the mixture was allowed to cool and then 400 mL of water was added with stirring. A solid precipitated, which was filtered. The filter cake was coated with dichloromethane and then loaded onto silica gel. The resulting product was obtained by silica gel column chromatography and recrystallization to yield the target compound M001-4. High-resolution mass spectrometry analysis revealed a target molecular mass of 1101.4536 (APCI source, [M+H)). + (Theoretical value: 1100.48).

[0183] (5) Synthesis of target compound M001

[0184]

[0185] Weigh 6.5 g (1.0 eq) of M001-4 into a 500 mL three-necked round-bottom flask, add 100 mL of ultra-dry xylene, and cool to below -30 °C under a nitrogen atmosphere using a liquid nitrogen-ethanol mixture. Then, slowly add 9.2 mL (2.5 eq) of 1.6 M tert-butyllithium solution. After the temperature of the reaction system slowly returns to room temperature, stir at 60 °C for 1 h. Cool again to below -30 °C using a liquid nitrogen-ethanol mixture, add 1.71 mL (3.0 eq) of boron tribromide, and slowly return to room temperature. Heat at 60 °C for 1 h. Cool again to below -0 °C using a liquid nitrogen-ethanol mixture, add 3.91 mL (4.0 eq) of N,N-diisopropylethylamine, and slowly return to room temperature. Heat at 120 °C for 12 h. After the reaction was completed, the mixture was allowed to stand and cool. Most of the xylene was removed by vacuum distillation. The remaining mixture was subjected to silica gel column chromatography to obtain the crude product. The crude product was then subjected to column chromatography and recrystallization to obtain M001. The target molecular mass was determined by high-resolution mass spectrometry to be 1075.4884 (APCI source, [M+H]+); theoretical value: 1074.51).

[0186] Synthesis Examples 2-10

[0187] The process routes for synthesizing Examples 2-10 are the same as or similar to those for Synthetic Example 1, except that the raw materials, reagents, and catalysts used are different. The raw materials, target products, and characterization data are shown in Table 1 below.

[0188] Table 1

[0189]

[0190]

[0191]

[0192] Theoretical calculations:

[0193] In this invention, theoretical calculations for organic compounds were performed using the Gaussian 16 program. The ground-state structure of the molecule was optimized using B3LYP 6-31G* / SMD to obtain the energy levels of the highest occupied orbital (HOMO) and lowest unoccupied orbital (LUMO) in the ground state. The structures of the lowest singlet and lowest triplet excited states of the molecule were optimized using the TD-B3LYP / 6-31G* method. The emission spectra (λem, nm) correspond to the excitation energies under the excited state configurations (toluene as solvent, PCM solvent model); ΔEST The energy level difference is between the first excited singlet state (S1) and the first excited triplet state (T1) in the ground state. The specific results are shown in Table 2.

[0194] Table 2

[0195] organic compounds HOMO(eV) LUMO(eV) <![CDATA[λ em (nm)]]> <![CDATA[T1(nm)]]> <![CDATA[ΔE ST (eV)]]> M001 -4.89 -1.74 493 1.96 0.56 Ref-1 -4.98 -1.64 462 2.37 0.31

[0196] As shown in Table 2, the first excited triplet energy level of M001 is 0.41 eV lower than that of Ref-A. This is attributed to the introduction of a 9,10-diphenylanthracene group with a lower triplet energy level in M001, while the triplet energy level of the phenanthrene group in Ref-A is higher. This indicates that by introducing a low triplet energy level group, the T1 energy of the compound is significantly reduced in this invention, ΔE ST Increased efficiency, as a dopant material for the light-emitting layer of organic electroluminescent devices, is expected to improve the efficiency roll-off and lifetime decay caused by the long-lifetime high-energy excitation triplet state.

[0197] The compounds of this invention can be used as doping materials in light-emitting devices. The fluorescence emission spectra of the compounds were measured using a Hitachi F-4600 fluorescence spectrophotometer in a toluene solution at room temperature, with a concentration of 10. -5 mol / L, S1 and T1 were calculated from the wavelengths corresponding to the peak values ​​of the fluorescence emission spectrum and phosphorescence emission spectrum obtained at 77K, respectively. The detection results are shown in Table 3.

[0198] Table 3

[0199] compound λem(nm) FWHM(nm) <![CDATA[S1(eV)]]> <![CDATA[T1(eV)]]> M001 513 22 2.41 / M217 488 23 2.53 / Ref-1 480 24 2.55 2.39

[0200] As shown in Table 3, compared to Ref-1 which has a higher T1 energy level, the T1 energy levels of compounds M001 and M217 provided by this invention were not detected under the test conditions. This indicates that after introducing the low-T1 energy level group 9-phenylanthracene, the T1 energy of the compounds of this invention is significantly reduced, ΔE ST Significantly increased, as a dopant material for the light-emitting layer of organic electroluminescent devices, it can significantly improve the efficiency roll-off and lifetime decay caused by the long-lifetime high-energy excitation triplet state.

[0201]

[0202] The compounds of this invention are used as fluorescent luminescent materials in light-emitting devices. The light-emitting devices are prepared using a vacuum evaporation method. The temperature at which the evaporation rate is 0.001 nm / s is used as the evaporation temperature of the material. The evaporation temperature test results for the compounds of this invention are shown in Table 4.

[0203] Table 4

[0204] compound Evaporation temperature / ℃ M003 275 Ref-2 290 Ref-3 296

[0205]

[0206] Implementation

[0207] Device Examples

[0208] An OLED includes a first electrode and a second electrode, and an organic material layer located between the electrodes. This organic material layer can be further divided into multiple regions. For example, the organic material layer may include a hole transport region, a light-emitting layer, and an electron transport region.

[0209] In specific embodiments, a substrate can be used below the first electrode or above the second electrode. The substrate is typically made of glass or polymer material with excellent mechanical strength, thermal stability, water resistance, and transparency. Furthermore, thin-film transistors (TFTs) can also be incorporated into the substrate used for displays.

[0210] 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.

[0211] Organic material layers can be formed on electrodes using methods such as vacuum thermal evaporation, spin coating, and printing. The compounds used as organic material layers can be small organic molecules, large organic molecules, polymers, and combinations thereof.

[0212] 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.

[0213] The material for the hole transport region can be selected from, but is not limited to, phthalocyanine derivatives such as CuPc, conductive polymers, or polymers containing conductive dopants such as polyphenylene oxide, polyaniline / dodecylbenzenesulfonic acid (Pani / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate).

[0214] (PEDOT / PSS), polyaniline / camphor sulfonic acid (Pani / CSA), polyaniline / poly(4-styrene sulfonate) (Pani / PSS), aromatic amine derivatives as shown in HT-1 to HT-51 below; or any combination thereof.

[0215]

[0216]

[0217]

[0218] 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 mentioned above, or one or more compounds of HI-1 to HI-3 mentioned 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 mentioned below.

[0219]

[0220] The emissive layer includes luminescent dyes (i.e., dopants) that can emit different wavelengths of light, and may also include a host material. The emissive layer can be a monochromatic emissive 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 can simultaneously emit different colors such as red, green, and blue.

[0221] Depending on the technology used, the light-emitting layer material can be various materials such as fluorescent electroluminescent materials, phosphorescent electroluminescent materials, and thermally activated delayed fluorescence materials. In an OLED device, a single light-emitting technology can be used, or a combination of multiple different light-emitting technologies can be employed. These different light-emitting materials, classified by technology, can emit light of the same color or different colors. In one aspect of this invention, the light-emitting layer employs phosphorescent electroluminescence technology. 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.

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228] In one aspect of the invention, the light-emitting layer employs phosphorescent photoluminescence technology. The phosphorescent dopant of the light-emitting layer may be selected from, but is not limited to, one or more combinations of BPD-1 to BPD-16 listed below.

[0229]

[0230] In one aspect of the invention, the light-emitting layer employs phosphorescent photoluminescence technology. The phosphorescent dopant of the light-emitting layer may be selected from, but is not limited to, one or more combinations of GPD-1 to GPD-60 listed below.

[0231]

[0232]

[0233]

[0234]

[0235] Where D represents deuterium.

[0236] 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-75 to PH-117 described above; or a mixture of one or more compounds of HT-1 to HT-51 and one or more compounds of PH-75 to PH-117 may be employed.

[0237] The OLED organic material layer 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).

[0238] 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.

[0239]

[0240]

[0241]

[0242]

[0243]

[0244] 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.

[0245] The device may also include an electron injection layer located between the electron transport layer and the cathode, and the electron injection layer material includes, but is not limited to, one or more combinations of the following.

[0246] LiQ, LiF, NaCl, CsF, Li2O, Cs2CO3, BaO, Na, Li, Ca, Mg, Yb.

[0247] The XX functional layers of this invention should also include the following compounds (Note: These are the closest prior art to this invention).

[0248] The fabrication process of the organic electroluminescent device in this embodiment is as follows:

[0249] The glass plate coated with the ITO transparent conductive layer was ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in a acetone:ethanol mixed solvent, baked in a clean environment until all moisture was removed, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam.

[0250] 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) stacked sequentially. The fabrication method of this organic electroluminescent device is as follows:

[0251] (1) Place the glass substrate with the anode in the vacuum chamber and evacuate it to a vacuum level of less than 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.

[0252] (2) The compound HT-4 was vacuum-deposited on the hole injection layer as a hole transport layer, and the total film thickness was 60 nm.

[0253] (3) The compound HT-40 was vacuum-deposited on the hole transport layer as an electron blocking layer, and the total film thickness was 5 nm.

[0254] (4) 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 various materials using a multi-source co-evaporation method. The total film thickness is 40 nm.

[0255] The ratio of the main material, the phosphorus photosensitizer, and the dopant is 94.5:5:0.5 (w / w / w). The main material is a PH-61:PH-3 (50 / 50, w / w) mixed main material, the phosphorus photosensitizer is GPD-51, and the dopant is the organic compound M001 provided by this invention.

[0256] (6) The compound ET-23 was vacuum-deposited on the light-emitting layer as a hole blocking layer, and the total film thickness was 5 nm.

[0257] (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.

[0258] (8) Vacuum evaporation of LiF as an electron injection layer on the electron transport layer with a thickness of 1 nm;

[0259] (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 0.2 nm / s, and the deposition rate of the metal electrode is controlled at 1 nm / s.

[0260] The device examples in the following specific embodiments of the present invention all adopt the aforementioned hierarchical structure, materials and preparation methods, with the only difference being the light-emitting layer.

[0261] Device Examples 2-16

[0262] An organic electroluminescent device is disclosed, wherein the light-emitting layer employs phosphorus-sensitized light-emitting technology, and the ratio of the host material, phosphorus sensitizer, and dopant material is 94.5:5:0.5 (w / w / w). The host material is a PH-61:PH-3 (50 / 50, w / w) mixed host, the phosphorus sensitizer is GPD-51, and the dopant materials are organic compounds provided by this invention, as shown in Table 5.

[0263] Comparative Examples 1-2

[0264] An organic electroluminescent device is provided, wherein the light-emitting layer adopts phosphorus photosensitive light-emitting technology. The only difference between this device and the device embodiment 1 is that the doping material M001 is replaced with Ref-1 and Ref-4.

[0265]

[0266] Device testing methods (including equipment and testing conditions):

[0267] The organic electroluminescent devices prepared by the above process were subjected to the following performance measurements:

[0268] Under the same brightness, the operating voltage, current efficiency, and lifetime of the organic electroluminescent devices prepared in Examples 1-16 and Comparative Examples 1-2 were measured using a digital source meter and a luminance meter. Specifically, the voltage was increased at a rate of 0.1V per second, and the measurement was performed when the current density of the organic electroluminescent device reached 10mA / cm². 2 The voltage at which the device operates is the same as its operating voltage. The device's operating voltage at 10 mA / cm² was obtained using the integrating sphere method. 2 External quantum efficiency (EQE, %) at current density; lifetime test results for LT95 are as follows: at a constant current density of 40 mA / cm² 2 The time taken for the brightness to decay during testing, such as LT95, refers to the time it takes for the brightness to decay to 95% of the initial brightness, in hours. The LT95 lifetime test value of device example 1 is recorded as 1.00. The LT95 lifetimes of devices examples 2-16 and comparative examples 1-2 are the ratios (relative lifetimes) of their respective LT95 lifetime test values ​​to the test value of device example 1.

[0269] The performance of organic electroluminescent devices is shown in Table 5 below.

[0270]

[0271]

[0272] As shown in Table 5, green light-emitting devices were prepared using the organic compounds provided in this invention as fluorescent doping materials and phosphorus-sensitized fluorescence luminescence technology. The compounds of this invention, by introducing groups with lower triplet energy levels, reduce the triplet energy level of the molecule, which can significantly improve lifetime decay caused by high-energy excitation of the long-lifetime triplet state. Therefore, the lifetimes of devices 1-15 are higher than those of comparative devices 1-2. The phenanthrene group in Ref-1 does not reduce the triplet energy level of the material; therefore, Ref-1 and Ref-2 both have higher triplet energy levels and longer delayed fluorescence lifetimes, resulting in shorter device lifetimes than devices 1-16.

[0273] The applicant declares that the above embodiments illustrate the organic compounds and their applications, but the present invention is not limited to the above embodiments, that is, it does not mean that the present invention must rely on the above embodiments to be implemented. Those skilled in the art should understand that any improvements to the present invention, equivalent substitutions of the raw materials of the product of 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 the structure shown in formula (1): In equation (1), X is independently one of O, S, Se, NR1, CR2R3, and SiR4R5; M1 is independently represented by O, S, Se, and NR. 21 CR 22 R 23 SiR 24 R 25 One of them; X 1 X 2 X 3 X 4 X 5 X 6 X 7 X 8 Each independently selected from CR A1 Or N; Y 1 Y 2 Y 3 Y 4 Each independently selected from CR A2 Or N; Z 1 Z 2 Each independently selected from CR A3 Or N; X 4 With X 5 They are either not connected to each other or linked together by chemical bonds to form a ring; R1, R2, R3, R4, R5, R 21 R 22 R 23 R 24 R 25 Each R2 and R3 is independently selected from any one of unsubstituted or R'-substituted C1-C20 straight-chain or branched alkyl groups, unsubstituted or R'-substituted C2-C20 alkenyl groups, unsubstituted or R'-substituted C3-C20 cycloalkyl groups, unsubstituted or R'-substituted C6-C60 aryl groups, and unsubstituted or R'-substituted C3-C60 heteroaryl groups; R2 and R3 are not connected or are linked into a ring by chemical bonds; R4 and R5 are not connected or are linked into a ring by chemical bonds; R 22 With R 23 The R are either not connected or linked by chemical bonds to form a ring; 24 With R 25 They are either not connected to each other or linked together by chemical bonds to form a ring; R A1 R A2 R A3 Each is independently selected from hydrogen, halogen, cyano, nitro, amino, hydroxyl, unsubstituted or R'-substituted C1-C20 straight-chain 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 C6-C30 arylsilyl, unsubstituted or R'-substituted One of the following: C2-C30 heteroarylsilyl, unsubstituted or R'-substituted C1-C20 alkylamino, 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; The R A1 R A2 R A3 Each is independently independent of its adjacent ring structure or connected to form a ring through chemical bonds, and the adjacent R A1 R A2 R A3 They are either not connected to each other or linked together by chemical bonds to form a ring; And the R A1 R A2 R A3 R1, R2, R3, R4, R5, R 21 R 22 R 23 R 24 R 25 Or at least one of R' is the structure shown in equation (a); In formula (a), L is selected from one of unsubstituted or R”-substituted C6-C60 arylene or unsubstituted or R”-substituted C3-C60 heteroarylene; X 11 X 12 X 13 X 14 X 15 X 16 X 17 X 18 Each is independently selected from C and CR. C1 It can be one of N, and one of them is C, wherein C is connected to L; The R C1 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 C2-C20 alkenyl, unsubstituted or R”-substituted C1-C20 alkoxy, unsubstituted or R”-substituted C1-C20 alkylsilyl, unsubstituted or R”-substituted C6-C30 arylsilyl, unsubstituted or R”-substituted C2-C30 heteroarylsilyl, unsubstituted or Any one of the following: R”-substituted C1-C20 alkylamino, cyano, nitro, amino, hydroxyl, 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; two adjacent R C1 They are either not connected or linked by chemical bonds to form a ring; R C1 Each R is independent and not connected to adjacent ring structures or is connected to form a ring by chemical bonds. Any two adjacent R C1 At least one group of the rings are connected by chemical bonds to form a ring G, wherein the ring G is selected from any one of unsubstituted or R'-substituted C3-C60 aromatic rings and unsubstituted or R'-substituted C3-C60 heteroaromatic rings; R' and R" are each independently selected from any one or at least two combinations of halogen, cyano, nitro, hydroxy, amino, C1-C20 straight-chain or branched alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylsilyl, C2-C30 heteroarylsilyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl, or R' has the structure shown in formula a. R' and R" are each independently not connected to the adjacent ring structure or connected to form a ring by chemical bonds, and adjacent R' or R" are not connected to each other or connected to form a ring by chemical bonds.

2. The organic compound according to claim 1, characterized in that, The organic compound has the structure shown in formula (2-1): In equation (2-1), X 1 X 2 X 3 X 6 X 7 X 8 Y 1 Y 2 Y 3 Y 4 Z 1 Z 2 The definition of M1 is the same as the definition in equation (1); M2 consists independently of carbon-carbon single bonds, O, S, Se, and NR. 31 CR 32 R 33 Si R 34 R 35 One of them; R 31 R 32 R 33 R 34 R 35 Each is independently selected from any one of unsubstituted or R'-substituted C1-C20 straight-chain or branched alkyl groups, unsubstituted or R'-substituted C3-C20 cycloalkyl groups, unsubstituted or R'-substituted C2-C20 alkenyl groups, unsubstituted or R'-substituted C6-C60 aryl groups, and unsubstituted or R'-substituted C3-C60 heteroaryl groups; wherein the R 32 With R 33 The R are either not connected or linked by chemical bonds to form a ring; 34 With R 35 They are either not connected to each other or are linked together by chemical bonds to form a ring.

3. The organic compound according to claim 1 or 2, characterized in that, The X is independently one of O, S, NR1, CR2R3, and SiR4R5; Preferably, X is independently one of O, S, and NR1; Preferably, X is independently one of O and NR1; Preferably, the organic compound has the structure shown in formula (2-1-1) or formula (2-1-2): In equations (2-1-1) and (2-1-2), X 1 X 2 X 3 X 6 X 7 X 8 Y 1 Y 2 Y 3 Y 4 Z 1 Z 2 The definition range of M1 is the same as that in equation (1); the definition range of M2 is the same as that in equation (2-1); R1 is independently selected from any one of the following: unsubstituted or R'-substituted C1-C10 straight-chain or branched alkyl, unsubstituted or R'-substituted C2-C20 alkenyl, unsubstituted or R'-substituted C3-C10 cycloalkyl, unsubstituted or R'-substituted C6-C30 aryl, and unsubstituted or R'-substituted C3-C30 heteroaryl. Preferably, the organic compound has the structure shown in formula (2-1-1), formula (2-1-2-1), or formula (2-1-2-2): In equations (2-1-1), (2-1-2-1), and (2-1-2-2), X 1 X 2 X 3 X 6 X 7 X 8 Y 1 Y 2 Y 3 Y 4 Z 1 Z 2 The definition range of M1 is the same as that in equation (1); the definition range of M2 is the same as that in equation (2-1); Y 5 Y 6 Y 7 Y 8 Y 9 Each R' is independently selected from one of CR' or N, and each R' is independently selected from one or a combination of two of the following: halogen, cyano, amino, C1-C20 straight-chain or branched alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylsilyl, C2-C30 heteroarylsilyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl, or R' has the structure shown in formula a; each R' is independently not connected to the adjacent ring structure or is connected to form a ring by a chemical bond, and adjacent R's are not connected to each other or are connected to form a ring by a chemical bond; Ra1 and Ra2 are each independently selected from one or a combination of two of the following: halogen, cyano, amino, C1-C20 straight-chain or branched alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylsilyl, C2-C30 heteroarylsilyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl, or have the structure shown in Formula a; Ra1 and Ra2 are each independently not connected to adjacent ring structures or are connected to each other by chemical bonds to form a ring; Ra1 and Ra2 are not connected to each other or are connected to each other by chemical bonds to form a ring. Preferably, in formula (2-1-2-1) Y 4 With Y 5 They are either not connected or connected in a loop; Preferably, the organic compound has the structure shown in formula (2-1-1), formula (2-1-2-2), formula (2-1-2-1-1), or formula (2-1-2-1-2): In this context, dashed lines represent single keys or no connection. X 1 X 2 X 3 X 6 X 7 X 8 Y 1 Y 2 Y 3 Y 4 Z 1 Z 2 The definition range of M1 is the same as that in equation (1); the definition range of M2 is the same as that in equation (2-1); Y 5 Y 6 Y 7 Y 8 Y 9 The definition range is the same as the definition range in equation (2-1-2-1); the definition ranges of Ra1 and Ra2 are the same as the definition ranges in equation (2-1-2-2); M3 is independently represented by O, S, Se, and NR. 41 CR 42 R 43 Si R 44 R 45 One of them; R 41 R 42 R 43 R 44 R 45 Each is independently selected from any one of unsubstituted or R'-substituted C1-C20 straight-chain or branched alkyl groups, unsubstituted or R'-substituted C3-C20 cycloalkyl groups, unsubstituted or R'-substituted C2-C20 alkenyl groups, unsubstituted or R'-substituted C6-C60 aryl groups, and unsubstituted or R'-substituted C3-C60 heteroaryl groups; wherein the R 42 With R 43 The R are either not connected or linked by chemical bonds to form a ring; 44 With R 45 They are either not connected to each other or linked together by chemical bonds to form a ring; Preferably, X is independent of NR1.

4. The organic compound according to any one of claims 1-3, characterized in that, The M2 independent components are carbon-carbon single bonds, O, S, Se, and NR. 31 CR 32 R 33 SiR 34 R 35 One of them; Preferably, the organic compound has the structure shown in formula (3-1), formula (3-2), or formula (3-3): In equation (3-2), Y 4 With Y 5 They are either not connected or connected in a loop; X 1 X 2 X 3 X 6 X 7 X 8 Y 1 Y 2 Y 3 Y 4 Z 1 Z 2 The definition range of M1 is the same as the definition range in equation (1); Y 5 Y 6 Y 7 Y 8 Y 9 The definition range is the same as the definition range in equation (2-1-2-1); the definition ranges of Ra1 and Ra2 are the same as the definition ranges in equation (2-1-2-2).

5. The organic compound according to any one of claims 1-4, characterized in that, The M1 is independently O, S, NR 21 CR 22 R 23 SiR 24 R 25 One of them; Preferably, M1 is independently O and NR. 21 CR 22 R 23 SiR 24 R 25 One of them; Preferably, M1 is independently O and CR 22 R 23 SiR 24 R 25 One of them; Preferably, M1 is independently O or CR. 22 R 23 ; Preferably, M1 is independently CR 22 R 23 ; Preferably, it has a structure shown in any of formulas (4-1), (4-2), (4-3), (4-4), (4-5), or (4-6): Among them, X 1 X 2 X 3 X 6 X 7 X 8 Y 1 Y 2 Y 3 Y 4 The definition scope of is the same as that in equation (1); Y 5 Y 6 Y 7 Y 8 Y 9 The definition range is the same as the definition range in equation (2-1-2-1); the definition ranges of Ra1 and Ra2 are the same as the definition ranges in equation (2-1-2-2); R 22 R 23 Each is independently selected from any one of unsubstituted or R'-substituted C1-C20 straight-chain or branched alkyl groups, unsubstituted or R'-substituted C2-C20 alkenyl groups, unsubstituted or R'-substituted C3-C20 cycloalkyl groups, unsubstituted or R'-substituted C6-C30 aryl groups, and unsubstituted or R'-substituted C3-C30 heteroaryl groups; wherein the R 22 With R 23 They are either not connected to each other or linked together by chemical bonds to form a ring; Preferably, it has a structure shown in any of formulas (4-2), (4-3), (4-4), (4-5), or (4-6): Preferably, it has the structure shown in formula (4-3), formula (4-4), or formula (4-6); Preferably, it has the structure shown in formula (4-4) or formula (4-6).

6. The organic compound according to claim 5, characterized in that, The organic compound has the structures shown in formula (4-3), formula (4-4-1), and formula (4-6-1): Rings E and F are selected from one of the following: R'-substituted or unsubstituted C6-C60 aromatic rings and R'-substituted or unsubstituted C2-C60 heteroaromatic rings; M4 represents a carbon-carbon single bond, O, S, Se, NR. 51 CR 52 R 53 Si R 54 R 55 One of them; R 51 R 52 R 53 R 54 R 55 Each is independently selected from any one or at least a combination of 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-C30 arylsilyl, C2-C30 heteroarylsilyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl; The R 52 With R 53 The R are either not connected or linked by chemical bonds to form a ring; 54 With R 55 They are either not connected to each other or linked together by chemical bonds to form a ring; m4 can be 0 or 1; m4 being 0 indicates that M4 does not exist. Preferably, it has the structure shown in formula (4-3) or formula (5-1): Among them, X 1 X 2 X 3 X 6 X 7 X 8 Y 1 Y 2 Y 3 Y 4 The scope of the definition is the same as that in equation (1); Y 5 Y 6 Y 7 Y 8 Y 9 The scope of its definition is the same as that defined in equation (2-1-2-1); The definition of M4 is the same as that in equation (4-4-1); X b1 X b2 X b3 X b4 X b5 X b6 X b7 X b8 Each independently selected from CR D1 Or any one of N; The R D1 Each is independently selected from one or a combination of two of the following: hydrogen, 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-C30 arylsilyl, C2-C30 heteroarylsilyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl; R D1 Each is independently independent of its adjacent ring structure or connected to form a ring through chemical bonds, and the adjacent R D1 They are either not connected to each other or linked together by chemical bonds to form a ring; Preferably, it has the structure shown in formula (5-1-1): Preferably, M4 is a carbon-carbon single bond, O, or CR. 52 R 53 SiR 54 R 55 One of them may not exist; Preferably, M4 is a carbon-carbon single bond or does not exist.

7. The organic compound according to any one of claims 1-6, characterized in that, Equation (a) can be any of the following structures: Where -* represents the linking site of the group; X 11 X 12 X 13 X 14 X 15 X 16 X 18 It has the same scope as in equation (a); X 21 X 22 X 23 X 24 X 31 X 32 X 33 X 34 X 35 X 41 X 42 X 43 X 44 X 45 X 46 X 51 X 52 X 53 X 54 Each is independently selected from either CR”' or N; Each R”' is independently selected from any one or at least two combinations of hydrogen, halogen, cyano, nitro, hydroxyl, amino, C1-C20 straight-chain or branched alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C6-C30 arylsilyl, C3-C30 heteroarylsilyl, C1-C20 alkylamino, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl. Each R”' is independently not connected to the adjacent ring structure or is connected to form a ring by a chemical bond, and adjacent R”'s are not connected to each other or are connected to form a ring by a chemical bond. Preferably, formula (a) is the structure shown in formula (a-1), formula (a-1-1), formula (a-2), formula (a-3), or formula (a-4-1): X 25 X 26 X 27 X 28 X 55 X 56 X 57 X 58 Each is independently selected from either CR”' or N; Each R”' is independently selected from any one or at least two combinations of hydrogen, halogen, cyano, nitro, hydroxyl, amino, C1-C20 straight-chain or branched alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C6-C30 arylsilyl, C3-C30 heteroarylsilyl, C1-C20 alkylamino, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl. Each R”' is independently not connected to or is linked to an adjacent ring structure by a chemical bond to form a ring, and adjacent R”'s are not connected to or are linked to each other by a chemical bond to form a ring. Preferably, X 11 X 12 X 13 X 14 X 15 X 16 X 18 X 21 X 22 X 23 X 24 X 31 X 32 X 33 X 34 X 35 X 41 X 42 X 43 X 44 X 45 X 46 X 51 X 52 X 53 X 54 X 25 X 26 X 27 X 28 X 55 X 56 X 57 X 58 Each is independently selected from CR”'; Preferably, formula (a) is the structure shown in formula (a-1) or formula (a-2); Preferably, in formula (a), L is selected from one of unsubstituted or R”-substituted C6-C30 arylene and unsubstituted or R”-substituted C3-C30 heteroarylene; Preferably, L is selected from one of phenylene, biphenylene, naphthylene, and pyridylene; Preferably, the L is selected from any one of the following groups: Where -* represents the linking site of the group; Y 11 Y 12 Y 13 Y 14 Each can be independently selected from either CR or N; Each of R” is independently selected from any one or at least two of the following: hydrogen, halogen, cyano, nitro, hydroxyl, amino, C1-C20 straight-chain or branched alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C6-C30 arylsilyl, C3-C30 heteroarylsilyl, C1-C20 alkylamino, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl; each of R” is independently not connected to or is connected to an adjacent ring structure by a chemical bond to form a ring, and adjacent R” are not connected to or are connected to each other by a chemical bond to form a ring; Preferably, L is selected from Any one of them, Further optimization Preferably, the Y 11 Y 12 Y 13 Y 14 Each is independently designated as a "CR"; Preferably, each of the R's is independently selected from hydrogen, C1-C20 straight-chain or branched alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C60 aryl, and C3-C60 heteroaryl; Preferably, R A1 R A2 R A3 Or at least one of R' is the structure shown in equation (a); Preferably, R A1 R A2 Or at least one of R' is the structure shown in equation (a); Preferably, R A1 R A2 At least one of them is the structure shown in equation (a); Preferably, X 2 or X 3 Y 2 Or Y 3 X 6 or X 7 One of them is the structure shown in equation (a).

8. The organic compound according to claim 1, characterized in that, It has the following structure:

9. The use of the organic compound according to any one of claims 1 to 8, wherein the use is as a functional material in an organic electronic device, the organic electronic device being selected from organic electroluminescent devices, optical sensors, solar cells, lighting elements, organic thin-film transistors, organic field-effect transistors, information tags, electronic artificial skin sheets, sheet-type scanners, or electronic paper; Preferably, the organic compound is used as a light-emitting layer material in an organic electroluminescent device, and more preferably as a light-emitting dye in the light-emitting layer.

10. An organic electroluminescent device, comprising a first electrode, a second electrode, and one or more light-emitting functional layers inserted between the first electrode and the second electrode, wherein the light-emitting functional layer contains an organic compound as described in any one of claims 1 to 8; Preferably, the light-emitting functional layer includes a light-emitting layer and at least one of a hole injection layer, a hole transport layer, an electron blocking layer, and an electron transport layer, wherein the light-emitting layer contains an organic compound as described in any one of claims 1 to 8.

11. A display device, characterized in that, The display device includes the organic electroluminescent device as described in claim 10.

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