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

Abstract

This invention relates to an organic compound, its applications, and organic electroluminescent devices comprising it. The organic compound of this invention has the structure shown in formula (1), where X1 connects to the structure shown in formula (Z1) or (Z2), and X2 connects to the structure shown in formula (Z1) or (Z2). "*" represents a connection site. X1 and X2 are independently selected from C, Si, or B, respectively. When X1 and X2 are independently connected to formula (Z2), X1 and X2 are independently selected from C. When the compound of this invention is applied to organic electroluminescent devices, it achieves high color purity and high luminous efficiency, along with an extremely long device lifetime and a low sublimation temperature.

Description

Technical Field

[0001] This invention relates to the field of organic electroluminescence technology, and particularly to an organic compound, as well as the application of this luminescent material and organic electroluminescent devices containing the compound. Background Technology

[0002] Organic light-emitting diodes (OLEDs) are a type of device with a sandwich-like structure, consisting of positive and negative electrode layers and an organic functional material layer sandwiched between them. When a voltage is applied to the electrodes of an OLED device, positive charges are injected from the positive electrode and negative charges from the negative electrode. Under the influence of an electric field, the positive and negative charges migrate, meet, and recombine within the organic layer to emit light. Due to their advantages such as high brightness, fast response, wide viewing angle, simple manufacturing process, and flexibility, OLED devices have attracted significant attention in the fields of new display technology and new lighting technology. Currently, this technology is widely used in display panels for new lighting fixtures, smartphones, and tablets, and its application is expected to expand further into large-size display products such as televisions. It is a rapidly developing and technologically demanding new display technology.

[0003] As OLED technology continues to advance in both lighting and display fields, research into its core materials is receiving increasing attention. This is because a high-efficiency, long-lifespan OLED device is typically the result of optimized device structure and the combination of various organic materials. To fabricate OLED devices with lower driving voltages, better luminous efficiency, and longer lifespans, and to continuously improve OLED device performance, innovation in OLED device structure and manufacturing processes is necessary, along with ongoing research and innovation in the optoelectronic functional materials used in OLED devices to develop higher-performance functional materials. Based on this, the OLED materials community has been dedicated to developing new organic electroluminescent materials to achieve devices with low start-up voltages, high luminous efficiency, and superior lifespans.

[0004] To meet the BT.2020 standard for next-generation ultra-high definition (UHD) video production and display systems issued by the International Telecommunication Union Radiocommunication Sector (ITU-R), luminescent materials, in addition to high efficiency and long lifespan, require a narrower half-width at half-maximum (HWHM) to achieve higher color purity. Currently commercially available OLED materials typically have a wide HWHM (>40nm). While optical filters can improve color purity, this leads to a decrease in brightness and efficiency, making it counterproductive.

[0005] The multiple resonance (MR) effect enables dyes to possess narrow fluorescence spectra and high fluorescence quantum yields, playing a crucial role in improving device performance. Currently, the MR effect is mainly induced by alternating nitrogen and boron atoms or carbonyl groups, but this also results in a long delayed fluorescence lifetime. While improving the color purity of the material, this also introduces stability issues, limiting the application of such materials. Therefore, it is necessary to develop MR materials with higher luminous efficiency and better lifetime to meet the current requirements of panel manufacturers for high-performance materials. Summary of the Invention

[0006] To address the aforementioned technical problems, this invention provides an organic compound exhibiting exceptionally long stability. The specific technical solution is as follows:

[0007] An organic compound having the structure shown in formula (1):

[0008]

[0009] In formula (1), ring Ar1, ring Ar2, ring Ar3, ring Ar4, ring Ar5 and ring Ar6 are each independently selected from one of the aromatic rings of C6 to C60 and the heteroaromatic rings of C3 to C60;

[0010] X1 connects the structures shown in formula (Z1) or formula (Z2), while X2 connects the structures shown in formula (Z1) or formula (Z2), where "*" represents the connection site;

[0011] In formula (Z1), ring Ar7 and ring Ar8 are each independently selected from one of the aromatic rings of C6 to C60 and the heteroaromatic rings of C3 to C60;

[0012] X1 and X2 are each independently selected from C, Si, or B; and when X1 and X2 are connected independently (Z2), X1 and X2 are each independently selected from C.

[0013] Furthermore, when X1 or X2 is independently B, in formula (Z1), one of the two atoms in ring Ar7 and ring Ar8 directly connected to X1 or X2 by chemical bonds is an N atom and the other is a C atom; when X1 and X2 are independently C or Si, in formula (Z1), both of the two atoms in ring Ar7 and ring Ar8 directly connected to X1 or X2 by chemical bonds are C atoms.

[0014] In formula (Z1), W1 is selected from carbon-carbon single bonds, O, S, Se, or NR. a ;

[0015] R aSelected from one of the following groups, whether R'-substituted or unsubstituted: C1-C36 chain alkyl, C3-C36 cycloalkyl, C6-C30 arylamino, C6-C60 aryl, C6-C60 aryloxy, or C5-C60 heteroaryl;

[0016] m1 is 0 or 1;

[0017] R1, R2, R3, R4, R5, R6, R7, and R8 are each independently selected from hydrogen, deuterium, halogen, carbonyl, carboxyl, nitro, cyano, amino, R'-substituted or unsubstituted C1-C30 chain alkyl, R'-substituted or unsubstituted C3-C20 cycloalkyl, R'-substituted or unsubstituted C7-C30 aralkyl, R'-substituted or unsubstituted C1-C30 alkoxy, R'-substituted or unsubstituted C2-C30 aliphatic chain amine, and R'-substituted or unsubstituted C4-C30 cyclic aliphatic chain amine. One of the following: a chain hydrocarbon amino group, a C6-C30 aryl amino group (R' substituted or unsubstituted), a C3-C30 heteroaryl amino group (R' substituted or unsubstituted), a C6-C30 aryloxy group (R' substituted or unsubstituted), a C6-C60 arylboryl group (R' substituted or unsubstituted), or a C3-C60 heteroaryl group (R' substituted or unsubstituted); and the connection mode of R1, R2, R3, R4, R5, R6, R7 and R8 on the corresponding ring structure is either single bond connection or fused connection;

[0018] n1, n2, n3, n4, n5, n6, n7, and n8 are each independently selected from integers from 1 to 10;

[0019] When n1, n2, n3, n4, n5, n6, n7, and n8 are each independent integers greater than 1, the corresponding multiple R1s, multiple R2s, multiple R3s, multiple R4s, multiple R5s, multiple R6s, multiple R7s, and multiple R8s are either the same or different, and the multiple R1s are either not connected or connected in a cycle, the multiple R2s are either not connected or connected in a cycle, the multiple R3s are either not connected or connected in a cycle, the multiple R4s are either not connected or connected in a cycle, the multiple R5s are either not connected or connected in a cycle, the multiple R6s are either not connected or connected in a cycle, the multiple R7s are either not connected or connected in a cycle, and the multiple R8s are either not connected or connected in a cycle.

[0020] The two adjacent R's mentioned above are either not connected or connected to form a ring; each R' is independently selected from one or a combination of two of the following: deuterium, halogen, cyano, amino, C2-C10 alkenyl, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C6-C60 arylboryl, C6-C60 aryl, and C3-C60 heteroaryl.

[0021] In this invention, the "substituted or unsubstituted" group can replace one substituent or multiple substituents. When there are multiple substituents, they can be selected from different substituents. In this invention, when the same expression is used, they all have the same meaning, and the selection range of substituents is as shown above and will not be repeated one by one.

[0022] In this specification, the expression Ca to Cb represents that the group has a to b carbon atoms. Unless otherwise specified, the number of carbon atoms generally does not include the number of carbon atoms of the substituents.

[0023] In this specification, the ring structure indicated by "—" represents any position on the ring structure where bonding can occur; the dashed double bond represents the position where the group is fused in the parent nucleus.

[0024] In this specification, "each independently" means that when there are multiple subjects, they may be the same or different from each other.

[0025] In this invention, the description of chemical elements, unless otherwise specified, usually includes the concept of their isotopes. For example, the description of "hydrogen (H)" includes the concept of its isotopes 1H (protium or H) and 2H (deuterium or D); carbon (C) includes 12C, 13C, etc., which will not be elaborated further.

[0026] In this invention, heteroatoms generally refer to atoms or groups of atoms selected from N, O, S, P, Si and Se, preferably selected from N, O and S.

[0027] Examples of halogens in this specification include fluorine, chlorine, bromine, and iodine.

[0028] In this invention, unless otherwise specified, aryl and heteroaryl groups include both monocyclic and fused-ring groups.

[0029] In this invention, the term "single bond connection or fused connection" generally refers to the substituent group being directly connected to the parent structure via a single bond, or the substituent group being fused to the parent structure, thereby forming a fused-ring aromatic hydrocarbon structure with multiple aromatic rings sharing the same edge. The aromatic rings here include six-membered aromatic rings such as benzene rings, as well as five-membered and six-membered heteroaromatic rings containing atoms such as N, O, or S.

[0030] In this invention, C6-C60 can 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.

[0031] 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.

[0032] 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.

[0033] C3-C20 can all be C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.

[0034] C6-C30 can all be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0035] C3-C30 can all be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0036] C2-C10 can all be C2, C3, C4, C5, C6, C7, C8, C9 or C10.

[0037] In this invention, the substituted or unsubstituted C6-C60 aryl (or C6-C50 aryl) includes monocyclic aryl and fused-ring aryl, preferably C6-C30 aryl, and more preferably C6-C20 aryl. A monocyclic aryl refers to a molecule containing at least one phenyl group. When a molecule contains at least two phenyl groups, the phenyl groups are independent of each other and connected by a single bond, exemplarily such as phenyl, biphenyl, and terphenyl. Specifically, the biphenyl includes 2-biphenyl, 3-biphenyl, and 4-biphenyl; the terphenyl includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, meta-terphenyl-4-yl, meta-terphenyl-3-yl, and meta-terphenyl-2-yl. A fused-ring aryl refers to a molecule containing at least two aromatic rings, where the aromatic rings are not independent of each other but share two adjacent carbon atoms fused together. Examples include: naphthyl, anthracene, phenanthrene, indene, fluorenyl, fluoranthyl, triphenylene, pyrene, perylene, etc. Naphthyl, 2-naphthyl, and their derivative groups, etc. The naphthyl includes 1-naphthyl or 2-naphthyl; the anthraceneyl is selected from 1-anthrayl, 2-anthrayl, and 9-anthrayl; the fluorenyl is selected from 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, and 9-fluorenyl; the pyrene is selected from 1-pyrene, 2-pyrene, and 4-pyrene; the 2-tetraphenyl is selected from 1-2 ... The fluorene derivative group is selected from 9,9-dimethylfluorenyl, 9,9-diethylfluorenyl, 9,9-dipropylfluorenyl, 9,9-dibutylfluorenyl, 9,9-dipentylfluorenyl, 9,9-dihexylfluorenyl, 9,9-diphenylfluorenyl, 9,9-dinaphthylfluorenyl, 9,9'-spirodifluorenyl, and benzo[a]fluorenyl.

[0038] The C3-C60 heteroaryl (or C6-C50 heteroaryl) mentioned in this invention includes monocyclic heteroaryl and fused-ring heteroaryl, preferably C3-C30 heteroaryl, more preferably C4-C20 heteroaryl, and even more preferably C5-C12 heteroaryl. A monocyclic heteroaryl refers to a molecule containing at least one heteroaryl group. When a molecule contains one heteroaryl group and other groups (such as aryl, heteroaryl, alkyl, etc.), the heteroaryl group and the other groups are independent of each other and connected by a single bond. Examples of monocyclic heteroaryl groups include furanyl, thiophene, pyrrole, and pyridinyl. A fused-ring heteroaryl refers to a molecule containing at least one aromatic heterocycle and an aromatic ring (aromatic heterocycle or aromatic ring), and the two are not independent of each other but share two adjacent atoms fused together. Examples of fused-ring heteroaryl groups include: benzofuranyl, benzothiophenyl, isobenzofuranyl, indolyl, dibenzofuranyl, dibenzothiophenyl, carbazoyl, acridineyl, isobenzofuranyl, isobenzothiophenyl, benzocarbazoyl, azircarbazoyl, phenothiazinyl, phenothiazinyl, 9-phenylcarbazoyl, 9-naphthylcarbazoyl, dibenzocarbazoyl, indolocarbazoyl, etc.

[0039] The aryloxy or heteroaryloxy groups in this invention can be exemplified by the monovalent groups formed by the above-mentioned aryl or heteroaryl groups and oxygen.

[0040] In this invention, arylamino represents a group formed by replacing the hydrogen on an amino group with one or two aryl groups, wherein the linking site of the arylamino can be linked to the aryl group in the arylamino or to the N group in the arylamino, and the exemplary number of carbons and specific groups of the aryl group in the arylamino are the same as described above.

[0041] Examples of C6-C30 arylamino groups mentioned in this invention include phenylamino, methylphenylamino, naphthylamino, anthraceneylamino, phenanthreneamino, and biphenylamino.

[0042] Examples of C3-C30 heteroaryl amino groups mentioned in this invention include pyridinyl amino, pyrimidinyl amino, and dibenzofuranyl amino.

[0043] Unless otherwise specified, the chain alkyl groups mentioned in this invention include straight-chain alkyl groups and branched-chain alkyl groups. Specifically, substituted or unsubstituted C1-C30 chain alkyl groups are preferred, substituted or unsubstituted C1-C16 chain alkyl groups are more preferably substituted or unsubstituted C1-C10 chain alkyl groups. Examples of substituted or unsubstituted C1-C10 chain alkyl groups include: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, neopentyl, n-hexyl, neohexyl, n-heptyl, n-octyl, 2-ethylhexyl, etc.

[0044] In this invention, the cycloalkyl group includes monocycloalkyl and polycycloalkyl; wherein, monocycloalkyl refers to an alkyl group containing a single ring structure; polycycloalkyl refers to a structure composed of two or more cycloalkyl groups sharing one or more carbon atoms on a ring; examples of C3-C20 cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, etc.

[0045] In this specification, the substituted or unsubstituted C1-C20 alkoxy group is preferably a substituted or unsubstituted C1-C10 alkoxy group. Examples of C1-C20 alkoxy groups include: methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, pentooxy, isopentoxy, hexoxy, heptoxy, octoxy, nonoxy, decoxy, undecoxy, dodecoxy, etc., among which methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy, sec-butoxy, isobutoxy, isopentoxy, and more preferably methoxy.

[0046] In this specification, the substituted or unsubstituted C1-C20 silane and the substituted or unsubstituted C1-C10 silane are examples of silanes substituted with groups listed in the above-mentioned C1-C10 chain alkyl groups, specifically including: methylsilane, dimethylsilane, trimethylsilane, ethylsilane, diethylsilane, triethylsilane, tert-butyldimethylsilane, tert-butyldiphenylsilane, etc.

[0047] In this specification, the C2-C20 alkenyl group, preferably C2-C10 alkenyl group, is a hydrocarbon group containing at least one C=C double bond, and includes, but is not limited to: vinyl, propenyl, allyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, butadienyl, pentadienyl, etc.

[0048] It should be noted that while the possible effects of each group / feature have been described separately for ease of explanation in this application, this does not mean that these groups / features act in isolation. In fact, the reason for achieving good performance is essentially the optimized combination of the entire molecule, the result of the synergistic effect between various groups, rather than the effect of a single group.

[0049] Furthermore, in the organic compound of formula (1) of the present invention, X1 and X2 are both C, or X1 and X2 are both Si, or X1 and X2 are both B;

[0050] Preferably, X1 and X2 are the same, X1 is connected to the structure shown in type (Z1), and X2 is connected to the structure shown in type (Z1); or, X1 and X2 are the same, X1 is connected to the structure shown in type (Z2), and X2 is connected to the structure shown in type (Z2).

[0051] More preferably, X1 and X2 are both C, X1 is connected in the structure shown in Z1, and X2 is connected in the structure shown in Z1; or, X1 and X2 are the same, X1 is connected in the structure shown in Z2, and X2 is connected in the structure shown in Z2.

[0052] More preferably, X1 and X2 are both C, and X1 is connected to the structure shown in formula (Z1), while X2 is connected to the structure shown in formula (Z1).

[0053] Furthermore, in the organic compound of formula (1) of the present invention, the rings Ar1, Ar2, Ar3, Ar4, Ar5, Ar6, Ar7 and Ar8 are each independently the structure shown in formula (a), formula (b) or formula (c);

[0054] The dashed double bonds represent the fusion positions of the following groups in formula (1) or formula (Z1): any of the dashed double bonds (b1), (b2), and (b3) represent the fusion positions of the group in formula (b), and any of the dashed double bonds (c1), (c2), and (c3) represent the fusion positions of the group in formula (c).

[0055]

[0056] In equations (a), (b), and (c), Z 1 Z 2 Z 3 Z 4 Z 5 Z 6 Z 7 Z 8 Z 9 Z 10 Z 11 Z 12 Each is independently selected from C, CH, or N;

[0057] In equation (c), Z is selected from O, S, and NR. 1 or CR 2 R 3 ;R 1 R 2 R 3 It is either not connected to adjacent groups or forms a ring through chemical bonds; R 2 With R 3 They are either not connected or connected in a loop;

[0058] R 1 R 2 R 3 Each is independently selected from one of the following: unsubstituted or R”-substituted C1-C20 chain alkyl, unsubstituted or R”-substituted C3-C20 cycloalkyl, unsubstituted or R”-substituted C6-C60 aryl, and unsubstituted or R”-substituted C3-C60 heteroaryl;

[0059] "R" is selected from any one or a combination of two of the following: deuterium, halogen, cyano, amino, C2-C20 alkenyl, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 thioalkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C6-C60 aryl, and C3-C60 heteroaryl.

[0060] Preferably, in formula (1), ring Ar3, ring Ar4, ring Ar5, ring Ar6, ring Ar7 and ring Ar8 each independently represent one of the aromatic rings of C6 to C30 and the heteroaromatic rings of C5 to C30;

[0061] Preferably, the rings Ar3, Ar4, Ar5, Ar6, Ar7, and Ar8 are each independently selected from benzene rings, naphthyl rings, anthracene rings, fluorene rings, furanyl, benzofuranyl, dibenzofuranyl, indolyl, benzoindolyl, carbazoleyl, indolocarbazoleyl, thiopheneyl, benzothiopheneyl, dibenzothiopheneyl, thiopheneyl, benzoanthrayl, phenanthroyl, pyrene, pyrene, peryl, fluoranyl, tetraphenyl, pentaphenyl, benzopyrene, biphenyl, amphyl, triphenyl, triphenyl, tetraphenyl, diphenyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, Pyrroleyl, isoindolyl, carbazoleyl, indoxcarbazoleyl, pyridyl, quinolinyl, isoquinolinyl, acridineyl, phenanthridineyl, benzo-5,6-quinolinyl, benzo-6,7-quinolinyl, benzo-7,8-quinolinyl, pyrazolyl, indazoleyl, imidazolyl, benzimidazoleyl, naphthimidazoleyl, phenanthridinemidazoleyl, pyridinimidazoleyl, pyrazinimidazoleyl, quinoxalinimidazoleyl, oxazolyl, benzooxazolyl, naphthimidazoleyl, anthraquinoxazolyl, phenanthridinemidazoleyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl;

[0062] More preferably, the rings Ar3, Ar4, Ar5, Ar6, Ar7, and Ar8 are each independently selected from one of the following: benzene ring, naphthyl ring, anthracene ring, fluorene ring, furanyl, benzofuranyl, dibenzofuranyl, indolyl, benzoindolyl, carbazoyl, indolocarbazoyl, benzothiophenyl, dibenzothiophenyl, thiophenyl, and pyridyl.

[0063] More preferably, the rings Ar3, Ar4, Ar5, and Ar6 are each independently selected from a benzene ring, and the rings Ar7 and Ar8 are each independently selected from a benzene ring or a pyridyl group.

[0064] The organic compound of the present invention may be further preferably structured as shown in formula (2):

[0065]

[0066] The definitions of ring Ar1, ring Ar2, R1, R2, R3, R4, R5, R6, R7, R8, n1, n2, n3, n4, n5, n6, n7, n8, X1, X2, W1, and m1 are the same as those in claim 1.

[0067] X1 connects to the structure shown in formula (Z3) or formula (Z2), while X2 connects to the structure shown in formula (Z3) or formula (Z2), where "*" represents the connection site;

[0068] When X1 and / or X2 in equation (2) are independently connected to equation (Z3), when X1 and X2 are B, Y1 is N; when X1 and X2 are independently C or Si, Y1 is C.

[0069] Preferably, m1 is 1, and W1 is independently selected from carbon-carbon single bonds, O, and S;

[0070] More preferably, m1 is 1, and W1 is selected from carbon-carbon single bonds.

[0071] Further preferred, in equation (2), X1 and X2 are both C, or X1 and X2 are both Si, or X1 and X2 are both B;

[0072] Preferably, X1 and X2 are the same, X1 is connected to the structure shown in (Z3), and X2 is connected to the structure shown in (Z3); or, X1 and X2 are the same, X1 is connected to the structure shown in (Z2), and X2 is connected to the structure shown in (Z2).

[0073] More preferably, X1 and X2 are both C, X1 is connected in the structure shown in (Z3), and X2 is connected in the structure shown in (Z3); or, X1 and X2 are the same, X1 is connected in the structure shown in (Z2), and X2 is connected in the structure shown in (Z2).

[0074] More preferably, X1 and X2 are both C, and X1 is connected to the structure shown in formula (Z3), while X2 is connected to the structure shown in formula (Z3).

[0075] The organic compounds of the present invention are further preferably structures shown in any of the following formulas (3-1), (3-2), (3-3), and (3-4):

[0076]

[0077]

[0078] Among them, the definitions of ring Ar1, ring Ar2, R1, R2, R3, R4, R5, R6, R7, R8, n1, n2, n3, n4, n5, n6, n7, and n8 are the same as those in equations (1) and (Z1);

[0079] R9 and R 10 The definition ranges of n7 and n8 are the same as those of R7 and R8; the definition ranges of n9 and n10 are the same as those of n7 and n8.

[0080] Preferably, the ring Ar1 and the ring Ar2 are each independently selected from the structure shown in formula (a) or formula (b);

[0081] More preferably, ring Ar1 and ring Ar2 are both structures shown in formula (a), or ring Ar1 and ring Ar2 are both structures shown in formula (b);

[0082] Most preferably, both ring Ar1 and ring Ar2 have the structure described in formula (a).

[0083] The organic compounds of the present invention are further preferably structures shown in any of the following formulas (4-1), (4-2), and (4-3):

[0084]

[0085] Among them, R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 The definitions of n1, n2, n3, n4, n5, n6, n7, n8, n9 and n10 are the same as those in equation (3-1).

[0086] In the compound formula of the present invention described above, R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 Each of the following is independently selected from hydrogen, deuterium, halogen, cyano, amino, R'-substituted or unsubstituted C1-C10 chain alkyl, R'-substituted or unsubstituted C3-C10 cycloalkyl, R'-substituted or unsubstituted C1-C10 alkoxy, R'-substituted or unsubstituted C2-C10 aliphatic chain alkylamine, R'-substituted or unsubstituted C4-C30 cycloaliphatic chain alkylamine, R'-substituted or unsubstituted C6-C30 arylamine, R'-substituted or unsubstituted C3-C30 heteroarylamine, R'-substituted or unsubstituted C6-C30 aryloxy, R'-substituted or unsubstituted C6-C30 arylboryl, R'-substituted or unsubstituted C6-C30 aryl, and R'-substituted or unsubstituted C3-C60 heteroaryl; and R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 Each of the corresponding ring structures is connected by a single bond or by fused bonding.

[0087] The two adjacent R's mentioned above are either not connected or connected to form a ring; each R' is independently selected from one or a combination of two of the following: deuterium, halogen, cyano, amino, C2-C10 alkenyl, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C8 alkoxy, C1-C8 thioalkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C6-C30 arylboryl, C6-C30 aryl, and C3-C30 heteroaryl.

[0088] Preferably, R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10Each of the following groups is independently selected from hydrogen, deuterium, cyano, halogen, amino, or a combination of two of the following substituents: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, phenyl, naphthyl, anthracene, benzo[a]anthrayl, phenanthrene, benzo[a]phenanthrene, pyrene, pyryl, peryl, fluoranyl, tetraphenyl, pentaphenyl, benzo[a]pyrene, biphenyl, amphylphenyl, terphenyl, triphenyl, tetraphenyl Fiberyl, spirodifluorenyl, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis or trans indofluorenyl, trimerinyl, isotrimericininyl, spirotrimericininyl, spiroisotrimericininyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thiopheneyl, benzothiopheneyl, isobenzothiopheneyl, dibenzothiopheneyl, pyrroleyl, isoindoleyl, carbazoleyl, indocarbazoleyl, pyridinyl, quinolinyl, isoquinolinyl, acridineyl, phenanthridineyl, benzo-5,6-quinolinyl, benzo-6,7-quinolinyl, benzo-7,8-quinolinyl, pyrazolyl, indazoleyl, imidazoleyl, benzimidazoleyl, naphthizimidazoleyl, phenanthrenezimidazoleyl, pyridinium-imidazolyl, pyridinium-imidazolyl Zizaimidazole, quinoxalinzimidazole, oxazolyl, benzoxoxazolyl, naphthoxoxazolyl, anthraquinoxazolyl, phenanthoxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazaanthrayl, 2,7-diazapyrene, 2,3-diazapyrene, 1,6-diazapyrene, 1,8-diazapyrene, 4,5-diazapyrene, 4,5,9,10-tetraazaperyl, pyrazinyl, phenazinyl, phenthiazinyl, naphridinyl, azacarbazolyl, benzocarbazolyl, phenanthrolinel, 1,2,3-triazolyl, 1,2,4-triazolyl Benzotriazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,3-triazinyl, tetrazolyl, 1,2,4,5-tetraazinyl, 1,2,3,4-tetraazinyl, 1,2,3,5-tetraazinyl, purinyl, pteridyl, inazinyl, benzothiadiazolyl, 9,9-dimethylacridyl, triarylamine, adamantyl, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl or methoxy;

[0089] More preferably, R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10Each of the following groups is independently selected from hydrogen, deuterium, cyano, halogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, 2-methylbutyl, trifluoromethyl, pentafluoroethyl, phenyl, naphthyl, anthracene, benzo[a]anthrayl, phenanthrene, benzo[a]phenanthrene, pyrene, tetraphenyl, pentaphenyl, benzo[a]pyrene, biphenyl, terphenyl, triphenyl, fluorenyl, spirodifluorenyl, furanyl, benzo[a]furanyl, isobenzo[a]furanyl, dibenzo[a]furanyl, thiophene, benzo[a]thiophene, isobenzo[a]thiophene, dibenzo[a]thiophene, pyrrole, isoindole, carbazole, indoxacarbazole, pyridinyl, quinolinyl, isoquinolinyl, pyrazolyl, indazole, imidazolyl, pyridazinyl, pyrimidinyl Benzopyrimidinyl, quinoxalinyl, pyrazinyl, phenazinyl, phenothiazinyl, naphridinyl, azacarbazoyl, benzocarbazoyl, phenanthrolinel, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, 1,2,3-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,3-triazinyl, tetrazolyl, 1,2,4,5-tetraazinyl, inazinyl, benzothiadiazolyl, 9,9-dimethylacridinyl, triarylamine, adamantyl, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl, or methoxy.

[0090] Furthermore, the general formula compounds of the present invention can preferably include the following specific structural compounds A-1 to A-256, which are merely representative examples:

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104] The structural design innovation of this type of compound is as follows:

[0105] In the innovative design of the parent core structure of the compound of this invention, the N atom and N atom connecting the central benzene ring are in the para position, and the B atom and B atom connecting the central benzene ring are in the para position. At the same time, spiro groups and / or adamantyl groups are designed to be introduced on both sides of the periphery of the central parent core.

[0106] The nitrogen atom donor portion on the central benzene ring of the compound's parent core forms an indolecarbazole core via bonding with the central benzene ring. This core possesses a larger conjugated structure and extension, effectively reducing the molecule's luminescence band gap and resulting in a significant redshift in the emitted light color. Due to the steric nature and large steric hindrance of the helical structure, intermolecular interactions are effectively suppressed, thereby preventing the decrease in efficiency and stability caused by molecular stacking. Simultaneously, the sublimation temperature of the molecule is effectively lowered, which is beneficial for long-term sublimation and thermal evaporation.

[0107] Furthermore, the compounds of this invention exhibit a higher concentration of aromatic rings in the donor, acceptor, and central conjugated system, resulting in a longer conjugated system and enhanced rigidity of the molecular system. This effectively suppresses shoulder peaks and mitigates the efficiency reduction caused by nonradiative transitions, while also significantly improving the horizontal orientation of the molecule. Consequently, the compounds of this invention achieve higher light extraction efficiency. Additionally, the core structure of the compounds of this invention effectively disperses the electron density of the molecule, thereby significantly enhancing molecular stability.

[0108] The most preferred structure of this type of compound is to introduce a helical structure (i.e., four chemical bonds are formed around C, Si, and B, with two planes being nearly perpendicular in space) on both sides of the central core, thereby connecting the two benzene rings, eliminating the original repulsion between hydrogen atoms, significantly enhancing the rigidity of the molecule, thereby improving the thermal stability of the material, further reducing the half-maximum width (FWHM), and improving color purity.

[0109] This invention has verified through extensive experiments that the electroluminescence spectrum of OLED devices prepared using the compounds of this invention exhibits a narrow half-width at half-maximum (≤25nm), high luminous efficiency, and significantly extended device lifetime. Simultaneously, the low material sublimation temperature effectively reduces energy consumption during device fabrication. Furthermore, the material synthesis is relatively simple, greatly simplifying the synthesis process and improving reaction yield. The corresponding electroluminescent devices possess high luminous efficiency and extremely long lifespan, meeting the current requirements of panel manufacturers for high-performance materials and demonstrating promising application prospects in industrialization.

[0110] A second objective of this invention is to provide an application of the compound described in the first objective, wherein the compound is used in an organic electroluminescent device. Preferably, the compound serves as a light-emitting layer material in the organic electroluminescent device, and is preferably a light-emitting dye.

[0111] A third objective of this invention is to provide an organic electroluminescent device. Specifically, an embodiment of this invention provides an organic electroluminescent device, comprising a substrate, and an anode layer, a plurality of light-emitting functional layers, and a cathode layer sequentially formed on the substrate; the light-emitting functional layers include a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer, wherein the hole injection layer is formed on the anode layer, the hole transport layer is formed on the hole injection layer, the cathode layer is formed on the electron transport layer, and the light-emitting layer is located between the hole transport layer and the electron transport layer; wherein, preferably, the light-emitting layer contains any of the general formula compounds of this invention shown in any of the general formulas (1) above, or the light-emitting layer contains at least one of the specific compounds A-1 to A-256 above. Detailed Implementation

[0112] The specific preparation methods of the above-mentioned new compounds of the present invention will be described in detail below using several synthetic examples, but the preparation methods of the present invention are not limited to these synthetic examples.

[0113] The various chemical reagents used in this invention, such as petroleum ether, tert-butylbenzene, sodium sulfate, toluene, dichloromethane, cesium carbonate, sodium hydride, boron tribromide, tetrahydrofuran, N,N-dimethylformamide, n-butyllithium, bis(di-benzylacetone)palladium, reaction intermediates, and other basic chemical raw materials, were all purchased from Shanghai Titan Technology Co., Ltd. and Xilong Chemical Co., Ltd.

[0114] The synthesis method of the compounds of this invention is briefly described below. First, the polybrominated intermediate and the corresponding iodinated compound are reacted via a Buchwald-Hartwig reaction to obtain the intermediate compound. Then, after lithium halide exchange with n-butyllithium, electrophilic boronization with boron tribromide is carried out, followed by dehydrogenation and cyclization under basic conditions to obtain the target compound.

[0115] Synthesis Examples

[0116] Example 1: Synthesis of Compound A-1

[0117]

[0118] In a double-necked flask under a nitrogen atmosphere, the polybrominated precursor A-1-1 (10 mmol), the corresponding iodinated compound (25 mmol), tris(dibenzylacetone)palladium (2 mmol), tri-tert-butylphosphine tetrafluoroborate (4 mmol), and sodium tert-butoxide (24 mmol) were added sequentially. 100 mL of ultra-dry toluene was added, and the mixture was heated to 110 °C and reacted for 12 hours. After cooling, the organic phase was separated and collected. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 15:1) to give compound A-1-2.

[0119] Compound A-1-2 (1 mmol) was dissolved in 20 mL of tert-butylbenzene in a sealed tube. After cooling to -78 °C, a pentane solution of n-butyllithium (1.60 M, 2.5 mmol) was added, followed by heating to 30 °C and reacting for 1 hour. The mixture was then cooled again to -78 °C, and boron tribromide (3 mmol) was slowly added. The mixture was then heated to 30 °C and stirred for another 1 hour. After cooling to 0 °C, diisopropylethylamine (5 mmol) was added, followed by heating to 160 °C and reacting for 12 hours. The solvent was removed under vacuum, and the mixture was passed through a silica gel column using petroleum ether:dichloromethane = 15:1 as the developing solvent to obtain the target compound A-1.

[0120] Example 2 Synthesis of Compound A-7

[0121]

[0122] In a double-necked flask under a nitrogen atmosphere, the polybrominated precursor A-1-1 (10 mmol), the corresponding iodinated compound (25 mmol), tris(dibenzylacetone)palladium (2 mmol), tri-tert-butylphosphine tetrafluoroborate (4 mmol), and sodium tert-butoxide (24 mmol) were added sequentially. 100 mL of ultra-dry toluene was added, and the mixture was heated to 110 °C and reacted for 12 hours. After cooling, the organic phase was separated and collected. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 15:1) to give compound A-7-2.

[0123] Compound A-7-2 (1 mmol) was dissolved in 20 mL of tert-butylbenzene in a sealed tube. After cooling to -78 °C, a pentane solution of n-butyllithium (1.60 M, 2.5 mmol) was added, followed by heating to 30 °C and reacting for 1 hour. The mixture was then cooled again to -78 °C, and boron tribromide (3 mmol) was slowly added. The mixture was then heated to 30 °C and stirred for another 1 hour. After cooling to 0 °C, diisopropylethylamine (5 mmol) was added, followed by heating to 160 °C and reacting for 12 hours. The solvent was removed under vacuum, and the mixture was passed through a silica gel column using petroleum ether:dichloromethane = 10:1 as the developing solvent to obtain the target compound A-7.

[0124] Example 3 Synthesis of compound A-10

[0125]

[0126] In a double-necked flask under a nitrogen atmosphere, the polybrominated precursor A-1-1 (10 mmol), the corresponding iodinated compound (25 mmol), tris(dibenzylacetone)palladium (2 mmol), tri-tert-butylphosphine tetrafluoroborate (4 mmol), and sodium tert-butoxide (24 mmol) were added sequentially. 100 mL of ultra-dry toluene was added, and the mixture was heated to 110 °C and reacted for 12 hours. After cooling, the organic phase was separated and collected. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 15:1) to give compound A-10-2.

[0127] Compound A-10-2 (1 mmol) was dissolved in 20 mL of tert-butylbenzene in a sealed tube. After cooling to -78 °C, a pentane solution of n-butyllithium (1.60 M, 2.5 mmol) was added, followed by heating to 30 °C and reacting for 1 hour. The mixture was then cooled again to -78 °C, and boron tribromide (3 mmol) was slowly added, followed by heating to 30 °C and stirring for another hour. After cooling to 0 °C, diisopropylethylamine (5 mmol) was added, followed by heating to 160 °C and reacting for 12 hours. The solvent was removed under vacuum, and the mixture was passed through a silica gel column using petroleum ether:dichloromethane = 15:1 as the developing solvent to obtain the target compound A-10.

[0128] Example 4 Synthesis of compound A-17

[0129]

[0130] In a double-necked flask under a nitrogen atmosphere, the polybrominated precursor A-1-1 (10 mmol), the corresponding iodinated compound (25 mmol), tris(dibenzylacetone)palladium (2 mmol), tri-tert-butylphosphine tetrafluoroborate (4 mmol), and sodium tert-butoxide (24 mmol) were added sequentially. 100 mL of ultra-dry toluene was added, and the mixture was heated to 110 °C and reacted for 12 hours. After cooling, the organic phase was separated and collected. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 15:1) to give compound A-17-2.

[0131] Compound A-17-2 (1 mmol) was dissolved in 20 mL of tert-butylbenzene in a sealed tube. After cooling to -78 °C, a pentane solution of n-butyllithium (1.60 M, 2.5 mmol) was added, followed by heating to 30 °C and reacting for 1 hour. The mixture was then cooled again to -78 °C, and boron tribromide (3 mmol) was slowly added. The mixture was then heated to 30 °C and stirred for another 1 hour. After cooling to 0 °C, diisopropylethylamine (5 mmol) was added, followed by heating to 160 °C and reacting for 12 hours. The solvent was removed under vacuum, and the mixture was passed through a silica gel column using petroleum ether:dichloromethane = 5:1 as the developing solvent to obtain the target compound A-17.

[0132] Example 5 Synthesis of compound A-22

[0133]

[0134] In a double-necked flask under a nitrogen atmosphere, the polybrominated precursor A-22-1 (10 mmol), the corresponding iodinated compound (25 mmol), tris(dibenzylacetone)palladium (2 mmol), tri-tert-butylphosphine tetrafluoroborate (4 mmol), and sodium tert-butoxide (24 mmol) were added sequentially. 100 mL of ultra-dry toluene was added, and the mixture was heated to 110 °C and reacted for 12 hours. After cooling, the organic phase was separated and collected. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to give compound A-22-2.

[0135] Compound A-22-2 (1 mmol) was dissolved in 20 mL of tert-butylbenzene in a sealed tube. After cooling to -78 °C, a pentane solution of n-butyllithium (1.60 M, 2.5 mmol) was added, followed by heating to 30 °C and reacting for 1 hour. The mixture was then cooled again to -78 °C, and boron tribromide (3 mmol) was slowly added. The mixture was then heated to 30 °C and stirred for another 1 hour. After cooling to 0 °C, diisopropylethylamine (5 mmol) was added, followed by heating to 160 °C and reacting for 12 hours. The solvent was removed under vacuum, and the mixture was passed through a silica gel column using petroleum ether:dichloromethane = 5:1 as the developing solvent to obtain the target compound A-22.

[0136] Example 6 Synthesis of compound A-31

[0137]

[0138] In a double-necked flask under a nitrogen atmosphere, the polybrominated precursor A-31-1 (10 mmol), the corresponding iodinated compound (25 mmol), tris(dibenzylacetone)palladium (2 mmol), tri-tert-butylphosphine tetrafluoroborate (4 mmol), and sodium tert-butoxide (24 mmol) were added sequentially. 100 mL of ultra-dry toluene was added, and the mixture was heated to 110 °C and reacted for 12 hours. After cooling, the organic phase was separated and collected. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 15:1) to give compound A-31-2.

[0139] Compound A-31-2 (1 mmol) was dissolved in 20 mL of tert-butylbenzene in a sealed tube. After cooling to -78 °C, a pentane solution of n-butyllithium (1.60 M, 2.5 mmol) was added, followed by heating to 30 °C and reacting for 1 hour. The mixture was then cooled again to -78 °C, and boron tribromide (3 mmol) was slowly added. The mixture was then heated to 30 °C and stirred for another 1 hour. After cooling to 0 °C, diisopropylethylamine (5 mmol) was added, followed by heating to 160 °C and reacting for 12 hours. The solvent was removed under vacuum, and the mixture was passed through a silica gel column using petroleum ether:dichloromethane = 15:1 as the developing solvent to obtain the target compound A-31.

[0140] Example 7 Synthesis of Compound A-43

[0141]

[0142] In a double-necked flask under a nitrogen atmosphere, the polybrominated precursor A-43-1 (10 mmol), the corresponding iodinated compound (25 mmol), tris(dibenzylacetone)palladium (2 mmol), tri-tert-butylphosphine tetrafluoroborate (4 mmol), and sodium tert-butoxide (24 mmol) were added sequentially. 100 mL of ultra-dry toluene was added, and the mixture was heated to 110 °C and reacted for 12 hours. After cooling, the organic phase was separated and collected. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to give compound A-43-2.

[0143] Compound A-43-2 (1 mmol) was dissolved in 20 mL of tert-butylbenzene in a sealed tube. After cooling to -78 °C, a pentane solution of n-butyllithium (1.60 M, 2.5 mmol) was added, followed by heating to 30 °C and reacting for 1 hour. The mixture was then cooled again to -78 °C, and boron tribromide (3 mmol) was slowly added, followed by heating to 30 °C and stirring for another hour. After cooling to 0 °C, diisopropylethylamine (5 mmol) was added, followed by heating to 160 °C and reacting for 12 hours. The solvent was removed under vacuum, and the mixture was passed through a silica gel column using petroleum ether:dichloromethane = 15:1 as the developing solvent to obtain the target compound A-43.

[0144] Example 8 Synthesis of Compound A-55

[0145]

[0146] In a double-necked flask under a nitrogen atmosphere, the polybrominated precursor A-1-1 (10 mmol), the corresponding iodinated compound (25 mmol), tris(dibenzylacetone)palladium (2 mmol), tri-tert-butylphosphine tetrafluoroborate (4 mmol), and sodium tert-butoxide (24 mmol) were added sequentially. 100 mL of ultra-dry toluene was added, and the mixture was heated to 110 °C and reacted for 12 hours. After cooling, the organic phase was separated and collected. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 15:1) to give compound A-55-2.

[0147] Compound A-55-2 (1 mmol) was dissolved in 20 mL of tert-butylbenzene in a sealed tube. After cooling to -78 °C, a pentane solution of n-butyllithium (1.60 M, 2.5 mmol) was added, followed by heating to 30 °C and reacting for 1 hour. The mixture was then cooled again to -78 °C, and boron tribromide (3 mmol) was slowly added. The temperature was then raised to 30 °C and stirred for another 1 hour. After cooling to 0 °C, diisopropylethylamine (5 mmol) was added, followed by heating to 160 °C and reacting for 12 hours. The solvent was removed under vacuum, and the mixture was passed through a silica gel column using petroleum ether:dichloromethane = 15:1 as the developing solvent to obtain the target compound A-55.

[0148] Example 9 Synthesis of Compound A-75

[0149]

[0150] In a double-necked flask under a nitrogen atmosphere, the polybrominated precursor A-1-1 (10 mmol), the two corresponding iodinated compounds (12.5 mmol each), tris(dibenzylacetone)palladium (2 mmol), tri-tert-butylphosphine tetrafluoroborate (4 mmol), and sodium tert-butoxide (24 mmol) were added sequentially. 100 mL of ultra-dry toluene was added, and the mixture was heated to 110 °C and reacted for 12 hours. After cooling, the organic phase was separated and collected. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 15:1) to give compound A-75-2.

[0151] Compound A-75-2 (1 mmol) was dissolved in 20 mL of tert-butylbenzene in a sealed tube. After cooling to -78 °C, a pentane solution of n-butyllithium (1.60 M, 2.5 mmol) was added, followed by heating to 30 °C and reacting for 1 hour. The mixture was then cooled again to -78 °C, and boron tribromide (3 mmol) was slowly added. The mixture was then heated to 30 °C and stirred for another 1 hour. After cooling to 0 °C, diisopropylethylamine (5 mmol) was added, followed by heating to 160 °C and reacting for 12 hours. The solvent was removed under vacuum, and the mixture was passed through a silica gel column using petroleum ether:dichloromethane = 15:1 as the developing solvent to obtain the target compound A-75.

[0152] Example 10 Synthesis of Compound A-88

[0153]

[0154] In a double-necked flask under a nitrogen atmosphere, the polybrominated precursor A-31-1 (10 mmol), the two corresponding iodinated compounds (12.5 mmol each), tris(dibenzylacetone)palladium (2 mmol), tri-tert-butylphosphine tetrafluoroborate (4 mmol), and sodium tert-butoxide (24 mmol) were added sequentially. 100 mL of ultra-dry toluene was added, and the mixture was heated to 110 °C and reacted for 12 hours. After cooling, the organic phase was separated and collected. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to give compound A-88-2.

[0155] Compound A-88-2 (1 mmol) was dissolved in 20 mL of tert-butylbenzene in a sealed tube. After cooling to -78 °C, a pentane solution of n-butyllithium (1.60 M, 2.5 mmol) was added, followed by heating to 30 °C and reacting for 1 hour. The mixture was then cooled again to -78 °C, and boron tribromide (3 mmol) was slowly added. The mixture was then heated to 30 °C and stirred for another 1 hour. After cooling to 0 °C, diisopropylethylamine (5 mmol) was added, followed by heating to 160 °C and reacting for 12 hours. The solvent was removed under vacuum, and the mixture was passed through a silica gel column using petroleum ether:dichloromethane = 20:1 as the developing solvent to obtain the target compound A-88.

[0156] Example 11 Synthesis of Compound A-97

[0157]

[0158] In a double-necked flask under a nitrogen atmosphere, the polybrominated precursor A-1-1 (10 mmol), the corresponding iodinated compound (25 mmol), tris(dibenzylacetone)palladium (2 mmol), tri-tert-butylphosphine tetrafluoroborate (4 mmol), and sodium tert-butoxide (24 mmol) were added sequentially. 100 mL of ultra-dry toluene was added, and the mixture was heated to 110 °C and reacted for 12 hours. After cooling, the organic phase was separated and collected. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 15:1) to give compound A-97-2.

[0159] Compound A-97-2 (1 mmol) was dissolved in 20 mL of tert-butylbenzene in a sealed tube. After cooling to -78 °C, a pentane solution of n-butyllithium (1.60 M, 2.5 mmol) was added, followed by heating to 30 °C and reacting for 1 hour. The mixture was then cooled again to -78 °C, and boron tribromide (3 mmol) was slowly added, followed by heating to 30 °C and stirring for another hour. After cooling to 0 °C, diisopropylethylamine (5 mmol) was added, followed by heating to 160 °C and reacting for 12 hours. The solvent was removed under vacuum, and the mixture was passed through a silica gel column using petroleum ether:dichloromethane = 15:1 as the developing solvent to obtain the target compound A-97.

[0160] Example 12 Synthesis of compound A-111

[0161]

[0162] In a double-necked flask under a nitrogen atmosphere, the polybrominated precursor A-111-1 (10 mmol), the corresponding iodinated compound (25 mmol), tris(dibenzylacetone)palladium (2 mmol), tri-tert-butylphosphine tetrafluoroborate (4 mmol), and sodium tert-butoxide (24 mmol) were added sequentially. 100 mL of ultra-dry toluene was added, and the mixture was heated to 110 °C and reacted for 12 hours. After cooling, the organic phase was separated and collected. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 5:1) to give compound A-111-2.

[0163] Compound A-111-2 (1 mmol) was dissolved in 20 mL of tert-butylbenzene in a sealed tube. After cooling to -78 °C, a pentane solution of n-butyllithium (1.60 M, 2.5 mmol) was added, followed by heating to 30 °C and reacting for 1 hour. The mixture was then cooled again to -78 °C, and boron tribromide (3 mmol) was slowly added. The mixture was then heated to 30 °C and stirred for another 1 hour. After cooling to 0 °C, diisopropylethylamine (5 mmol) was added, followed by heating to 160 °C and reacting for 12 hours. The solvent was removed under vacuum, and the mixture was passed through a silica gel column using petroleum ether:dichloromethane = 15:1 as the developing solvent to obtain the target compound A-111.

[0164] Example 13 Synthesis of compound A-114

[0165]

[0166] In a double-necked flask under a nitrogen atmosphere, the polybrominated precursor A-1-1 (10 mmol), the corresponding iodinated compound (25 mmol), tris(dibenzylacetone)palladium (2 mmol), tri-tert-butylphosphine tetrafluoroborate (4 mmol), and sodium tert-butoxide (24 mmol) were added sequentially. 100 mL of ultra-dry toluene was added, and the mixture was heated to 110 °C and reacted for 12 hours. After cooling, the organic phase was separated and collected. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 15:1) to give compound A-114-2.

[0167] Compound A-114-2 (1 mmol) was dissolved in 20 mL of tert-butylbenzene in a sealed tube. After cooling to -78 °C, a pentane solution of n-butyllithium (1.60 M, 2.5 mmol) was added, followed by heating to 30 °C and reacting for 1 hour. The mixture was then cooled again to -78 °C, and boron tribromide (3 mmol) was slowly added. The mixture was then heated to 30 °C and stirred for another 1 hour. After cooling to 0 °C, diisopropylethylamine (5 mmol) was added, followed by heating to 160 °C and reacting for 12 hours. The solvent was removed under vacuum, and the mixture was passed through a silica gel column using petroleum ether:dichloromethane = 15:1 as the developing solvent to obtain the target compound A-114.

[0168] Example 14 Synthesis of Compound A-123

[0169]

[0170] In a double-necked flask under a nitrogen atmosphere, the polybrominated precursor A-22-1 (10 mmol), the corresponding iodinated compound (25 mmol), tris(dibenzylacetone)palladium (2 mmol), tri-tert-butylphosphine tetrafluoroborate (4 mmol), and sodium tert-butoxide (24 mmol) were added sequentially. 100 mL of ultra-dry toluene was added, and the mixture was heated to 110 °C and reacted for 12 hours. After cooling, the organic phase was separated and collected. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 15:1) to give compound A-123-2.

[0171] Compound A-123-2 (1 mmol) was dissolved in 20 mL of tert-butylbenzene in a sealed tube. After cooling to -78 °C, a pentane solution of n-butyllithium (1.60 M, 2.5 mmol) was added, followed by heating to 30 °C and reacting for 1 hour. The mixture was then cooled again to -78 °C, and boron tribromide (3 mmol) was slowly added, followed by heating to 30 °C and stirring for another hour. After cooling to 0 °C, diisopropylethylamine (5 mmol) was added, followed by heating to 160 °C and reacting for 12 hours. The solvent was removed under vacuum, and the mixture was passed through a silica gel column using petroleum ether:dichloromethane = 15:1 as the developing solvent to obtain the target compound A-123.

[0172] Example 15 Synthesis of Compound A-130

[0173]

[0174] In a double-necked flask under a nitrogen atmosphere, the polybrominated precursor A-1-1 (10 mmol), the corresponding iodinated compound (25 mmol), tris(dibenzylacetone)palladium (2 mmol), tri-tert-butylphosphine tetrafluoroborate (4 mmol), and sodium tert-butoxide (24 mmol) were added sequentially. 100 mL of ultra-dry toluene was added, and the mixture was heated to 110 °C and reacted for 12 hours. After cooling, the organic phase was separated and collected. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to give compound A-130-2.

[0175] Compound A-130-2 (1 mmol) was dissolved in 20 mL of tert-butylbenzene in a sealed tube. After cooling to -78 °C, a pentane solution of n-butyllithium (1.60 M, 2.5 mmol) was added, followed by heating to 30 °C and reacting for 1 hour. The mixture was then cooled again to -78 °C, and boron tribromide (3 mmol) was slowly added, followed by heating to 30 °C and stirring for another hour. After cooling to 0 °C, diisopropylethylamine (5 mmol) was added, followed by heating to 160 °C and reacting for 12 hours. The solvent was removed under vacuum, and the mixture was passed through a silica gel column using petroleum ether:dichloromethane = 10:1 as the developing solvent to obtain the target compound A-130.

[0176] Example 16 Synthesis of Compound A-146

[0177]

[0178] In a double-necked flask under a nitrogen atmosphere, the polybrominated precursor A-1-1 (10 mmol), the two corresponding iodinated compounds (12.5 mmol each), tris(dibenzylacetone)palladium (2 mmol), tri-tert-butylphosphine tetrafluoroborate (4 mmol), and sodium tert-butoxide (24 mmol) were added sequentially. 100 mL of ultra-dry toluene was added, and the mixture was heated to 110 °C and reacted for 12 hours. After cooling, the organic phase was separated and collected. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 15:1) to give compound A-146-2.

[0179] Compound A-146-2 (1 mmol) was dissolved in 20 mL of tert-butylbenzene in a sealed tube. After cooling to -78 °C, a pentane solution of n-butyllithium (1.60 M, 2.5 mmol) was added, followed by heating to 30 °C and reacting for 1 hour. The mixture was then cooled again to -78 °C, and boron tribromide (3 mmol) was slowly added, followed by heating to 30 °C and stirring for another hour. After cooling to 0 °C, diisopropylethylamine (5 mmol) was added, followed by heating to 160 °C and reacting for 12 hours. The solvent was removed under vacuum, and the mixture was passed through a silica gel column using petroleum ether:dichloromethane = 10:1 as the developing solvent to obtain the target compound A-146.

[0180] Example 17 Synthesis of Compound A-153

[0181]

[0182] In a double-necked flask under a nitrogen atmosphere, the polybrominated precursor A-1-1 (10 mmol), the corresponding iodinated compound (25 mmol), tris(dibenzylacetone)palladium (2 mmol), tri-tert-butylphosphine tetrafluoroborate (4 mmol), and sodium tert-butoxide (24 mmol) were added sequentially. 100 mL of ultra-dry toluene was added, and the mixture was heated to 110 °C and reacted for 12 hours. After cooling, the organic phase was separated and collected. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to give compound A-153-2.

[0183] Compound A-153-2 (1 mmol) was dissolved in 20 mL of tert-butylbenzene in a sealed tube. After cooling to -78 °C, a pentane solution of n-butyllithium (1.60 M, 2.5 mmol) was added, followed by heating to 30 °C and reacting for 1 hour. The mixture was then cooled again to -78 °C, and boron tribromide (3 mmol) was slowly added, followed by heating to 30 °C and stirring for another hour. After cooling to 0 °C, diisopropylethylamine (5 mmol) was added, followed by heating to 160 °C and reacting for 12 hours. The solvent was removed under vacuum, and the mixture was passed through a silica gel column using petroleum ether:dichloromethane = 10:1 as the developing solvent to obtain the target compound A-153.

[0184] Example 18 Synthesis of Compound A-158

[0185]

[0186] In a double-necked flask under a nitrogen atmosphere, the polybrominated precursor A-1-1 (10 mmol), the corresponding iodinated compound (25 mmol), tris(dibenzylacetone)palladium (2 mmol), tri-tert-butylphosphine tetrafluoroborate (4 mmol), and sodium tert-butoxide (24 mmol) were added sequentially. 100 mL of ultra-dry toluene was added, and the mixture was heated to 110 °C and reacted for 12 hours. After cooling, the organic phase was separated and collected. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 15:1) to give compound A-158-2.

[0187] Compound A-158-2 (1 mmol) was dissolved in 20 mL of tert-butylbenzene in a sealed tube. After cooling to -78 °C, a pentane solution of n-butyllithium (1.60 M, 2.5 mmol) was added, followed by heating to 30 °C and reacting for 1 hour. The mixture was then cooled again to -78 °C, and boron tribromide (3 mmol) was slowly added, followed by heating to 30 °C and stirring for another hour. After cooling to 0 °C, diisopropylethylamine (5 mmol) was added, followed by heating to 160 °C and reacting for 12 hours. The solvent was removed under vacuum, and the mixture was passed through a silica gel column using petroleum ether:dichloromethane = 15:1 as the developing solvent to obtain the target compound A-158.

[0188] Example 19 Synthesis of Compound A-168

[0189]

[0190] In a double-necked flask under a nitrogen atmosphere, the polybrominated precursor A-31-1 (10 mmol), the corresponding iodinated compound (25 mmol), tris(dibenzylacetone)palladium (2 mmol), tri-tert-butylphosphine tetrafluoroborate (4 mmol), and sodium tert-butoxide (24 mmol) were added sequentially. 100 mL of ultra-dry toluene was added, and the mixture was heated to 110 °C and reacted for 12 hours. After cooling, the organic phase was separated and collected. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 15:1) to give compound A-168-2.

[0191] Compound A-168-2 (1 mmol) was dissolved in 20 mL of tert-butylbenzene in a sealed tube. After cooling to -78 °C, a pentane solution of n-butyllithium (1.60 M, 2.5 mmol) was added, followed by heating to 30 °C and reacting for 1 hour. The mixture was then cooled again to -78 °C, and boron tribromide (3 mmol) was slowly added, followed by heating to 30 °C and stirring for another hour. After cooling to 0 °C, diisopropylethylamine (5 mmol) was added, followed by heating to 160 °C and reacting for 12 hours. The solvent was removed under vacuum, and the mixture was passed through a silica gel column using petroleum ether:dichloromethane = 10:1 as the developing solvent to obtain the target compound A-168.

[0192] Example 20 Synthesis of Compound A-174

[0193]

[0194] In a double-necked flask under a nitrogen atmosphere, the polybrominated precursor A-1-1 (10 mmol), the two corresponding iodinated compounds (12.5 mmol each), tris(dibenzylacetone)palladium (2 mmol), tri-tert-butylphosphine tetrafluoroborate (4 mmol), and sodium tert-butoxide (24 mmol) were added sequentially. 100 mL of ultra-dry toluene was added, and the mixture was heated to 110 °C and reacted for 12 hours. After cooling, the organic phase was separated and collected. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 5:1) to give compound A-174-2.

[0195] Compound A-174-2 (1 mmol) was dissolved in 20 mL of tert-butylbenzene in a sealed tube. After cooling to -78 °C, a pentane solution of n-butyllithium (1.60 M, 2.5 mmol) was added, followed by heating to 30 °C and reacting for 1 hour. The mixture was then cooled again to -78 °C, and boron tribromide (3 mmol) was slowly added, followed by heating to 30 °C and stirring for another hour. After cooling to 0 °C, diisopropylethylamine (5 mmol) was added, followed by heating to 160 °C and reacting for 12 hours. The solvent was removed under vacuum, and the mixture was passed through a silica gel column using petroleum ether:dichloromethane = 10:1 as the developing solvent to obtain the target compound A-174.

[0196] Example 21 Synthesis of Compound A-186

[0197]

[0198] In a double-necked flask under a nitrogen atmosphere, the polybrominated precursor A-31-1 (10 mmol), the two corresponding iodinated compounds (12.5 mmol each), tris(dibenzylacetone)palladium (2 mmol), tri-tert-butylphosphide tetrafluoroborate (4 mmol), and sodium tert-butoxide (24 mmol) were added sequentially. 100 mL of ultra-dry toluene was added, and the mixture was heated to 110 °C and reacted for 12 hours. After cooling, the organic phase was separated and collected. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to give compound A-186-2.

[0199] Compound A-186-2 (1 mmol) was dissolved in 20 mL of tert-butylbenzene in a sealed tube. After cooling to -78 °C, a pentane solution of n-butyllithium (1.60 M, 2.5 mmol) was added, followed by heating to 30 °C and reacting for 1 hour. The mixture was then cooled again to -78 °C, and boron tribromide (3 mmol) was slowly added. The mixture was then heated to 30 °C and stirred for another 1 hour. After cooling to 0 °C, diisopropylethylamine (5 mmol) was added, followed by heating to 160 °C and reacting for 12 hours. The solvent was removed under vacuum, and the mixture was passed through a silica gel column using petroleum ether:dichloromethane = 5:1 as the developing solvent to obtain the target compound A-186.

[0200] Example 22 Synthesis of Compound A-193

[0201]

[0202] In a double-necked flask under a nitrogen atmosphere, the polybrominated precursor A-1-1 (10 mmol), the corresponding iodinated compound (25 mmol), tris(dibenzylacetone)palladium (2 mmol), tri-tert-butylphosphine tetrafluoroborate (4 mmol), and sodium tert-butoxide (24 mmol) were added sequentially. 100 mL of ultra-dry toluene was added, and the mixture was heated to 110 °C and reacted for 12 hours. After cooling, the organic phase was separated and collected. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to give compound A-193-2.

[0203] Compound A-193-2 (1 mmol) was dissolved in 20 mL of tert-butylbenzene in a sealed tube. After cooling to -78 °C, a pentane solution of n-butyllithium (1.60 M, 2.5 mmol) was added, followed by heating to 30 °C and reacting for 1 hour. The mixture was then cooled again to -78 °C, and boron tribromide (3 mmol) was slowly added. The mixture was then heated to 30 °C and stirred for another 1 hour. After cooling to 0 °C, diisopropylethylamine (5 mmol) was added, followed by heating to 160 °C and reacting for 12 hours. The solvent was removed under vacuum, and the mixture was passed through a silica gel column using petroleum ether:dichloromethane = 10:1 as the developing solvent to obtain the target compound A-193.

[0204] Example 23 Synthesis of Compound A-200

[0205]

[0206] In a double-necked flask under a nitrogen atmosphere, the polybrominated precursor A-1-1 (10 mmol), the corresponding iodinated compound (25 mmol), tris(dibenzylacetone)palladium (2 mmol), tri-tert-butylphosphine tetrafluoroborate (4 mmol), and sodium tert-butoxide (24 mmol) were added sequentially. 100 mL of ultra-dry toluene was added, and the mixture was heated to 110 °C and reacted for 12 hours. After cooling, the organic phase was separated and collected. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 5:1) to give compound A-200-2.

[0207] Compound A-200-2 (1 mmol) was dissolved in 20 mL of tert-butylbenzene in a sealed tube. After cooling to -78 °C, a pentane solution of n-butyllithium (1.60 M, 2.5 mmol) was added, followed by heating to 30 °C and reacting for 1 hour. The mixture was then cooled again to -78 °C, and boron tribromide (3 mmol) was slowly added, followed by heating to 30 °C and stirring for another hour. After cooling to 0 °C, diisopropylethylamine (5 mmol) was added, followed by heating to 160 °C and reacting for 12 hours. The solvent was removed under vacuum, and the mixture was passed through a silica gel column using petroleum ether:dichloromethane = 5:1 as the developing solvent to obtain the target compound A-200.

[0208] Example 24 Synthesis of compound A-204

[0209]

[0210] In a double-necked flask under a nitrogen atmosphere, the polybrominated precursor A-22-1 (10 mmol), the corresponding iodinated compound (25 mmol), tris(dibenzylacetone)palladium (2 mmol), tri-tert-butylphosphine tetrafluoroborate (4 mmol), and sodium tert-butoxide (24 mmol) were added sequentially. 100 mL of ultra-dry toluene was added, and the mixture was heated to 110 °C and reacted for 12 hours. After cooling, the organic phase was separated and collected. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 15:1) to give compound A-204-2.

[0211] Compound A-204-2 (1 mmol) was dissolved in 20 mL of tert-butylbenzene in a sealed tube. After cooling to -78 °C, a pentane solution of n-butyllithium (1.60 M, 2.5 mmol) was added, followed by heating to 30 °C and reacting for 1 hour. The mixture was then cooled again to -78 °C, and boron tribromide (3 mmol) was slowly added, followed by heating to 30 °C and stirring for another hour. After cooling to 0 °C, diisopropylethylamine (5 mmol) was added, followed by heating to 160 °C and reacting for 12 hours. The solvent was removed under vacuum, and the mixture was passed through a silica gel column using petroleum ether:dichloromethane = 10:1 as the developing solvent to obtain the target compound A-204.

[0212] Example 25 Synthesis of Compound A-216

[0213]

[0214] In a double-necked flask under a nitrogen atmosphere, the polybrominated precursor A-1-1 (10 mmol), the two corresponding iodinated compounds (12.5 mmol each), tris(dibenzylacetone)palladium (2 mmol), tri-tert-butylphosphine tetrafluoroborate (4 mmol), and sodium tert-butoxide (24 mmol) were added sequentially. 100 mL of ultra-dry toluene was added, and the mixture was heated to 110 °C and reacted for 12 hours. After cooling, the organic phase was separated and collected. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 15:1) to give compound A-216-2.

[0215] Compound A-216-2 (1 mmol) was dissolved in 20 mL of tert-butylbenzene in a sealed tube. After cooling to -78 °C, a pentane solution of n-butyllithium (1.60 M, 2.5 mmol) was added, followed by heating to 30 °C and reacting for 1 hour. The mixture was then cooled again to -78 °C, and boron tribromide (3 mmol) was slowly added, followed by heating to 30 °C and stirring for another hour. After cooling to 0 °C, diisopropylethylamine (5 mmol) was added, followed by heating to 160 °C and reacting for 12 hours. The solvent was removed under vacuum, and the mixture was passed through a silica gel column using petroleum ether:dichloromethane = 15:1 as the developing solvent to obtain the target compound A-216.

[0216] Example 26 Synthesis of Compound A-226

[0217]

[0218] In a double-necked flask under a nitrogen atmosphere, the polybrominated precursor A-31-1 (10 mmol), the two corresponding iodinated compounds (12.5 mmol each), tris(dibenzylacetone)palladium (2 mmol), tri-tert-butylphosphide tetrafluoroborate (4 mmol), and sodium tert-butoxide (24 mmol) were added sequentially. 100 mL of ultra-dry toluene was added, and the mixture was heated to 110 °C and reacted for 12 hours. After cooling, the organic phase was separated and collected. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to give compound A-226-2.

[0219] Compound A-226-2 (1 mmol) was dissolved in 20 mL of tert-butylbenzene in a sealed tube. After cooling to -78 °C, a pentane solution of n-butyllithium (1.60 M, 2.5 mmol) was added, followed by heating to 30 °C and reacting for 1 hour. The mixture was then cooled again to -78 °C, and boron tribromide (3 mmol) was slowly added. The mixture was then heated to 30 °C and stirred for another 1 hour. After cooling to 0 °C, diisopropylethylamine (5 mmol) was added, followed by heating to 160 °C and reacting for 12 hours. The solvent was removed under vacuum, and the mixture was passed through a silica gel column using petroleum ether:dichloromethane = 10:1 as the developing solvent to obtain the target compound A-226.

[0220] Example 27 Synthesis of Compound A-233

[0221]

[0222] In a double-necked flask under a nitrogen atmosphere, the polybrominated precursor A-1-1 (10 mmol), the corresponding iodinated compound (25 mmol), tris(dibenzylacetone)palladium (2 mmol), tri-tert-butylphosphine tetrafluoroborate (4 mmol), and sodium tert-butoxide (24 mmol) were added sequentially. 100 mL of ultra-dry toluene was added, and the mixture was heated to 110 °C and reacted for 12 hours. After cooling, the organic phase was separated and collected. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 15:1) to give compound A-233-2.

[0223] Compound A-233-2 (1 mmol) was dissolved in 20 mL of tert-butylbenzene in a sealed tube. After cooling to -78 °C, a pentane solution of n-butyllithium (1.60 M, 2.5 mmol) was added, followed by heating to 30 °C and reacting for 1 hour. The mixture was then cooled again to -78 °C, and boron tribromide (3 mmol) was slowly added, followed by heating to 30 °C and stirring for another hour. After cooling to 0 °C, diisopropylethylamine (5 mmol) was added, followed by heating to 160 °C and reacting for 12 hours. The solvent was removed under vacuum, and the mixture was passed through a silica gel column using petroleum ether:dichloromethane = 10:1 as the developing solvent to obtain the target compound A-233.

[0224] Example 28 Synthesis of Compound A-235

[0225]

[0226] In a double-necked flask under a nitrogen atmosphere, the polybrominated precursor A-1-1 (10 mmol), the corresponding iodinated compound (25 mmol), tris(dibenzylacetone)palladium (2 mmol), tri-tert-butylphosphine tetrafluoroborate (4 mmol), and sodium tert-butoxide (24 mmol) were added sequentially. 100 mL of ultra-dry toluene was added, and the mixture was heated to 110 °C and reacted for 12 hours. After cooling, the organic phase was separated and collected. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to give compound A-235-2.

[0227] Compound A-235-2 (1 mmol) was dissolved in 20 mL of tert-butylbenzene in a sealed tube. After cooling to -78 °C, a pentane solution of n-butyllithium (1.60 M, 2.5 mmol) was added, followed by heating to 30 °C and reacting for 1 hour. The mixture was then cooled again to -78 °C, and boron tribromide (3 mmol) was slowly added, followed by heating to 30 °C and stirring for another hour. After cooling to 0 °C, diisopropylethylamine (5 mmol) was added, followed by heating to 160 °C and reacting for 12 hours. The solvent was removed under vacuum, and the mixture was passed through a silica gel column using petroleum ether:dichloromethane = 10:1 as the developing solvent to obtain the target compound A-235.

[0228] Example 29 Synthesis of Compound A-238

[0229]

[0230] In a double-necked flask under a nitrogen atmosphere, the polybrominated precursor A-1-1 (10 mmol), the corresponding iodinated compound (25 mmol), tris(dibenzylacetone)palladium (2 mmol), tri-tert-butylphosphine tetrafluoroborate (4 mmol), and sodium tert-butoxide (24 mmol) were added sequentially. 100 mL of ultra-dry toluene was added, and the mixture was heated to 110 °C and reacted for 12 hours. After cooling, the organic phase was separated and collected. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to give compound A-238-2.

[0231] Compound A-238-2 (1 mmol) was dissolved in 20 mL of tert-butylbenzene in a sealed tube. After cooling to -78 °C, a pentane solution of n-butyllithium (1.60 M, 2.5 mmol) was added, followed by heating to 30 °C and reacting for 1 hour. The mixture was then cooled again to -78 °C, and boron tribromide (3 mmol) was slowly added. The mixture was then heated to 30 °C and stirred for another 1 hour. After cooling to 0 °C, diisopropylethylamine (5 mmol) was added, followed by heating to 160 °C and reacting for 12 hours. The solvent was removed under vacuum, and the mixture was passed through a silica gel column using petroleum ether:dichloromethane = 5:1 as the developing solvent to obtain the target compound A-238.

[0232] Example 30 Synthesis of compound A-247

[0233]

[0234] In a double-necked flask under a nitrogen atmosphere, the polybrominated precursor A-247-1 (10 mmol), the corresponding iodinated compound (25 mmol), tris(dibenzylacetone)palladium (2 mmol), tri-tert-butylphosphine tetrafluoroborate (4 mmol), and sodium tert-butoxide (24 mmol) were added sequentially. 100 mL of ultra-dry toluene was added, and the mixture was heated to 110 °C and reacted for 12 hours. After cooling, the organic phase was separated and collected. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 5:1) to give compound A-247-2.

[0235] Compound A-247-2 (1 mmol) was dissolved in 20 mL of tert-butylbenzene in a sealed tube. After cooling to -78 °C, a pentane solution of n-butyllithium (1.60 M, 2.5 mmol) was added, followed by heating to 30 °C and reacting for 1 hour. The mixture was then cooled again to -78 °C, and boron tribromide (3 mmol) was slowly added, followed by heating to 30 °C and stirring for another hour. After cooling to 0 °C, diisopropylethylamine (5 mmol) was added, followed by heating to 160 °C and reacting for 12 hours. The solvent was removed under vacuum, and the mixture was passed through a silica gel column using petroleum ether:dichloromethane = 5:1 as the developing solvent to obtain the target compound A-247.

[0236] Example 31 Synthesis of compound A-252

[0237]

[0238] In a double-necked flask under a nitrogen atmosphere, the polybrominated precursor A-252-1 (10 mmol), the corresponding iodinated compound (25 mmol), tris(dibenzylacetone)palladium (2 mmol), tri-tert-butylphosphine tetrafluoroborate (4 mmol), and sodium tert-butoxide (24 mmol) were added sequentially. 100 mL of ultra-dry toluene was added, and the mixture was heated to 110 °C and reacted for 12 hours. After cooling, the organic phase was separated and collected. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was purified by silica gel column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to give compound A-252-2.

[0239] Compound A-252-2 (1 mmol) was dissolved in 20 mL of tert-butylbenzene in a sealed tube. After cooling to -78 °C, a pentane solution of n-butyllithium (1.60 M, 2.5 mmol) was added, followed by heating to 30 °C and reacting for 1 hour. The mixture was then cooled again to -78 °C, and boron tribromide (3 mmol) was slowly added, followed by heating to 30 °C and stirring for another hour. After cooling to 0 °C, diisopropylethylamine (5 mmol) was added, followed by heating to 160 °C and reacting for 12 hours. The solvent was removed under vacuum, and the mixture was passed through a silica gel column using petroleum ether:dichloromethane = 15:1 as the developing solvent to obtain the target compound A-252.

[0240] The specific experimental results of synthesis examples 1-31 are as follows:

[0241]

[0242]

[0243]

[0244] Note: The HPLC instrument used was a Shimadzu Nexera LC-40 series liquid chromatograph. The MALDI-TOF-MS instrument used was a Shimadzu AXIMA Performance MALDI-TOF. The elemental analysis instrument used was a Thermo Fisher FlashSmart elemental analyzer.

[0245] Device Examples

[0246] The technical effects and advantages of the present invention will be demonstrated and verified by specifically applying the compounds of the present invention to organic electroluminescent devices and testing their actual performance.

[0247] An organic electroluminescent device includes a first electrode, a second electrode, and an organic material layer located between the two electrodes. This organic material layer can be further divided into multiple regions; for example, it may include a hole transport region, a light-emitting layer, and an electron transport region.

[0248] The anode material can be any combination of transparent conductive oxide materials such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), and zinc oxide (ZnO). The cathode material can be any combination of metals or alloys such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag).

[0249] The hole transport region is located between the anode and the light-emitting layer. The hole transport region can be a single-layer hole transport layer (HTL), including a single-layer hole transport layer containing only one compound and a single-layer hole transport layer containing multiple compounds. The hole transport region can also be a multilayer structure including at least one of a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL).

[0250] 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) (PEDOT / PSS), polyaniline / camphorsulfonic acid (Pani / CSA), polyaniline / poly(4-styrenesulfonate) (Pani / PSS), aromatic amine derivatives, etc.

[0251] 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.

[0252] The electron transport region can be a single-layer electron transport layer (ETL), including a single-layer electron transport layer containing only one compound and a single-layer electron transport layer containing multiple compounds. The electron transport region can also 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).

[0253] Specifically, the method for fabricating the organic electroluminescent device of the present invention includes the following steps:

[0254] 1. The glass plate coated with the anodic material is ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in a mixture of acetone and ethanol, baked in a clean environment until all moisture is removed, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam.

[0255] 2. Place the glass plate with the anode in a vacuum chamber and evacuate it to 1×10-5~9×10-3 Pa. Vacuum deposit hole injection material on the anode film to form a hole injection layer. The deposition rate is 0.1-0.5 nm / s.

[0256] 3. A hole transport layer is formed by vacuum evaporation of a hole transport material on top of the hole injection layer, with an evaporation rate of 0.1-0.5 nm / s.

[0257] 4. An electron blocking layer is vacuum-deposited on top of the hole transport layer at a deposition rate of 0.1-0.5 nm / s;

[0258] 5. An organic light-emitting layer of the device is vacuum-deposited on top of the electron blocking layer. The organic light-emitting layer material includes a host material and a light-emitting dye. By using a multi-source co-evaporation method, the evaporation rate of the host material, the evaporation rate of the sensitizer material, and the evaporation rate of the dye are adjusted to make the dye reach a preset doping ratio.

[0259] 6. A hole blocking layer is vacuum-deposited on the organic light-emitting layer at a deposition rate of 0.1-0.5 nm / s;

[0260] 7. An electron transport layer is formed by vacuum evaporating the electron transport material of the device on top of the hole blocking layer, with an evaporation rate of 0.1-0.5 nm / s;

[0261] 8. A LiF layer is vacuum-deposited at 0.1-0.5 nm / s as the electron injection layer on the electron transport layer, and an Al layer is vacuum-deposited at 0.1-0.5 nm / s as the cathode of the device.

[0262] This invention also provides a display device, which includes the organic electroluminescent device as described above. Specifically, the display device can be an OLED display or other display device, as well as any product or component with display function, such as a television, digital camera, mobile phone, or tablet computer, that includes the display device. The advantages of this display device over the prior art are the same as those of the organic electroluminescent device described above, and will not be repeated here.

[0263] The organic electroluminescent device of the present invention will be further described below through specific embodiments.

[0264] Device Example 1

[0265] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0266] ITO / HI(5nm) / HT(24nm) / EBL / (12nm) / Host:3wt%A-1(30nm) / HBL(12nm) / ET(24nm) / LiF(0.7nm) / Al(150nm)

[0267] In this embodiment, the anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm (5 nm in this example); the hole transport layer material is HT, with a total thickness of 5-500 nm (24 nm in this example); the electron blocking layer material is EBL, with a total thickness of 0-30 nm (12 nm in this example); the host is the main material of the wide bandgap organic light-emitting layer, A-1 is a dye with a doping concentration of 3 wt%, and the thickness of the organic light-emitting layer is generally 1-200 nm (30 nm in this example); the hole blocking layer material is HBL, with a total thickness of 0-30 nm (12 nm in this example); the electron transport layer material is ET, with a thickness of 5-300 nm (24 nm in this example); and the electron injection layer and cathode materials are LiF (0.7 nm) and aluminum (150 nm).

[0268] Device Example 2

[0269] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0270] ITO / HI(5nm) / HT(24nm) / EBL / (12nm) / Host:35wt%TD:3wt%A-1(30nm) / HBL(12nm) / ET(24nm) / LiF(0.7nm) / Al(150nm)

[0271] In this embodiment, the anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm (5 nm in this example); the hole transport layer material is HT, with a total thickness of 5-500 nm (24 nm in this example); the electron blocking layer material is EBL, with a total thickness of 0-30 nm (12 nm in this example); the host is the main material of the wide bandgap organic light-emitting layer, TD is a TADF type host with a doping concentration of 35 wt%, A-1 is a dye with a doping concentration of 3 wt%, and the thickness of the organic light-emitting layer is generally 1-200 nm (30 nm in this example); the hole blocking layer material is HBL, with a total thickness of 0-30 nm (12 nm in this example); the electron transport layer material is ET, with a thickness of 5-300 nm (24 nm in this example); and the electron injection layer and cathode materials are LiF (0.7 nm) and aluminum (150 nm).

[0272] Device Examples 1 and 2 are respectively non-sensitized and sensitized devices for dye A-1.

[0273] Examples 3-62 of this invention are the same as those in Device Examples 1 and 2, except that the dye is replaced with the compound of this invention. They are also divided into two groups: unsensitized and sensitized devices. Comparative Examples 1-6 are parallel comparative devices prepared using existing compounds P1, P2, and P3 according to the same preparation method as the compounds of this invention. The structural schemes of all prepared devices are shown in Table 1 below:

[0274] Table 1:

[0275]

[0276]

[0277]

[0278] The structural formulas of the various organic materials used in the above embodiments are as follows:

[0279]

[0280]

[0281]

[0282] The performance of the devices prepared in Examples 1-62 and Comparative Examples 1-6 of this invention is shown in Table 2 below:

[0283] Table 2:

[0284]

[0285]

[0286]

[0287] Note: In Table 2, the half-width at half-maximum (WHM) is the half-width of the electroluminescence spectrum in the device. It is the peak width at half the peak height, that is, the distance between the two points where the straight line parallel to the bottom of the peak passes through the midpoint of the peak height and intersects the two sides of the peak.

[0288] The photoelectric properties of OLED devices, such as current density and external quantum efficiency, as well as their photochromic properties, such as electroluminescence spectrum, were obtained using a combination of a Hamamatsu C9920-02G quantum efficiency meter and a Keithley 2400 semiconductor analyzer. Device lifetime (LT97@10mA / cm) 2 ( / h) represents the time taken for the device brightness to decrease to 97% of its initial brightness, where the initial brightness is a current density of 10 mA / cm². 2 The corresponding brightness was obtained by testing using the OLED aging life test system of Shanghai University.

[0289] In Table 2, LT97@10mA / cm 2 The relative value of / h is the result obtained by comparing with Comparative Example 1.

[0290] As shown in Table 2 above, compared to Comparative Examples 1 and 2, the structural difference between the compound of the present invention and comparative compound P1 is that the present invention has more aromatic rings doped into the donor and central conjugated system. This structural design effectively reduces the luminescence band gap of the molecule, resulting in a further red shift in the emitted light color, and further improves the structural rigidity, significantly enhancing the stability of the device. Analyzing Comparative Examples 3 and 4, comparative compound P2 connects the arylboron portion to the benzene ring via chemical bonds, shortening the intermolecular distance and strengthening the intermolecular forces. This results in a significant decrease in efficiency and a shortened lifetime due to molecular aggregation. Analyzing Comparative Examples 5 and 6, the core framework of comparative compound P3 is significantly different from that of the compound of the present invention. In the central benzene ring of the parent nucleus, the N atom donor portion of the compound of the present invention forms an indolecarbazole core through bonding with the central benzene ring, exhibiting a larger conjugated structure and extension, effectively reducing the luminescence band gap of the molecule, resulting in a further red shift in the emitted light color. Simultaneously, the molecular structure of the compound of the present invention can effectively disperse the electron density of the molecule, thereby significantly improving the stability of the molecule. Meanwhile, compared to the three comparative compounds, the compounds of this invention introduce spiro structures and / or adamantane structures (i.e., four chemical bonds formed around C, Si, and B, with two planes being nearly perpendicular in space) on both sides of the central core, thereby connecting the benzene rings on both sides, eliminating the original repulsion between hydrogen atoms, significantly enhancing the rigidity of the molecule, improving color purity, and effectively suppressing intermolecular interactions due to the spatial stereochemistry and large steric hindrance of the spiro structure, thus suppressing the decrease in efficiency and stability caused by molecular stacking. At the same time, it effectively lowers the sublimation temperature of the molecule, which is beneficial for long-term sublimation and thermal evaporation, thereby reducing the energy consumption of device fabrication and improving the thermal stability of the material, showing greater promise for industrial applications.

[0291] The experimental data above demonstrate that the novel narrow-spectrum materials provided by this invention, when used in the preparation of organic electroluminescent devices, achieve excellent performance in terms of high color purity and high luminous efficiency, while also exhibiting an extremely long device lifetime. Therefore, these novel compounds of this invention are high-performance organic light-emitting functional materials and hold promise for widespread commercial application.

[0292] Although the invention has been described with reference to embodiments, it is not limited to the above embodiments. It should be understood that various modifications and improvements can be made by those skilled in the art under the guidance of the inventive concept, and the appended claims summarize the scope of the invention. Obviously, the above embodiments are merely examples for clear illustration and are not intended to limit the implementation. For those skilled in the art, other variations or modifications can be made based on the above description. It is neither necessary nor possible to exhaustively describe all embodiments here. However, obvious variations or modifications derived therefrom are still within the protection scope of this invention.

Claims

1. An organic compound having the structure shown in formula (1): In formula (1), ring Ar1, ring Ar2, ring Ar3, ring Ar4, ring Ar5 and ring Ar6 are each independently selected from one of the aromatic rings of C6 to C60 and the heteroaromatic rings of C3 to C60; X1 connects the structure shown in formula (Z1) or formula (Z2), and X2 connects the structure shown in formula (Z1) or formula (Z2), where "*" represents the connection site; In formula (Z1), ring Ar7 and ring Ar8 are each independently selected from one of the aromatic rings of C6 to C60 and the heteroaromatic rings of C3 to C60; X1 and X2 are each independently selected from C, Si, or B; and when X1 and X2 are connected independently (Z2), X1 and X2 are each independently selected from C. Furthermore, when X1 or X2 is independently B, in formula (Z1), one of the two atoms in ring Ar7 and ring Ar8 directly connected to X1 or X2 by chemical bonds is an N atom and the other is a C atom; when X1 and X2 are independently C or Si, in formula (Z1), both of the two atoms in ring Ar7 and ring Ar8 directly connected to X1 or X2 by chemical bonds are C atoms. In formula (Z1), W1 is selected from carbon-carbon single bonds, O, S, Se, or NR. a ; R a Selected from one of the following groups, whether R'-substituted or unsubstituted: C1-C36 chain alkyl, C3-C36 cycloalkyl, C6-C30 arylamino, C6-C60 aryl, C6-C60 aryloxy, or C5-C60 heteroaryl; m1 is 0 or 1; R1, R2, R3, R4, R5, R6, R7, and R8 are each independently selected from hydrogen, deuterium, halogen, carbonyl, carboxyl, nitro, cyano, amino, R'-substituted or unsubstituted C1-C30 chain alkyl, R'-substituted or unsubstituted C3-C20 cycloalkyl, R'-substituted or unsubstituted C7-C30 aralkyl, R'-substituted or unsubstituted C1-C30 alkoxy, R'-substituted or unsubstituted C2-C30 aliphatic chain amine, and R'-substituted or unsubstituted C4-C30 cyclic aliphatic chain amine. One of the following: a chain hydrocarbon amino group, a C6-C30 aryl amino group (R' substituted or unsubstituted), a C3-C30 heteroaryl amino group (R' substituted or unsubstituted), a C6-C30 aryloxy group (R' substituted or unsubstituted), a C6-C60 arylboryl group (R' substituted or unsubstituted), or a C3-C60 heteroaryl group (R' substituted or unsubstituted); and the connection mode of R1, R2, R3, R4, R5, R6, R7 and R8 on the corresponding ring structure is either single bond connection or fused connection; n1, n2, n3, n4, n5, n6, n7, and n8 are each independently selected from integers from 1 to 10; When n1, n2, n3, n4, n5, n6, n7, and n8 are each independent integers greater than 1, the corresponding multiple R1s, multiple R2s, multiple R3s, multiple R4s, multiple R5s, multiple R6s, multiple R7s, and multiple R8s are either the same or different, and the multiple R1s are either not connected or connected in a cycle, the multiple R2s are either not connected or connected in a cycle, the multiple R3s are either not connected or connected in a cycle, the multiple R4s are either not connected or connected in a cycle, the multiple R5s are either not connected or connected in a cycle, the multiple R6s are either not connected or connected in a cycle, the multiple R7s are either not connected or connected in a cycle, and the multiple R8s are either not connected or connected in a cycle. The two adjacent R's mentioned above are either not connected or connected to form a ring; each R' is independently selected from one or a combination of two of the following: deuterium, halogen, cyano, amino, C2-C10 alkenyl, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C6-C60 arylboryl, C6-C60 aryl, and C3-C60 heteroaryl.

2. The organic compound according to claim 1, characterized in that, X1 and X2 are both C, or X1 and X2 are both Si, or X1 and X2 are both B; Preferably, X1 and X2 are the same, X1 is connected to the structure shown in type (Z1), and X2 is connected to the structure shown in type (Z1); or, X1 and X2 are the same, X1 is connected to the structure shown in type (Z2), and X2 is connected to the structure shown in type (Z2). More preferably, X1 and X2 are both C, X1 is connected in the structure shown in Z1, and X2 is connected in the structure shown in Z1; or, X1 and X2 are the same, X1 is connected in the structure shown in Z2, and X2 is connected in the structure shown in Z2. More preferably, X1 and X2 are both C, and X1 is connected to the structure shown in formula (Z1), while X2 is connected to the structure shown in formula (Z1).

3. The organic compound according to claim 1, characterized in that, The rings Ar1, Ar2, Ar3, Ar4, Ar5, Ar6, Ar7, and Ar8 are each independently represented by the structure shown in equation (a), equation (b), or equation (c). The dashed double bonds represent the fusion positions of the following groups in formula (1) or formula (Z1): any of the dashed double bonds (b1), (b2), and (b3) represent the fusion positions of the group in formula (b), and any of the dashed double bonds (c1), (c2), and (c3) represent the fusion positions of the group in formula (c). In equations (a), (b), and (c), Z 1 Z 2 Z 3 Z 4 Z 5 Z 6 Z 7 Z 8 Z 9 Z 10 Z 11 Z 12 Each is independently selected from C, CH, or N; In equation (c), Z is selected from O, S, and NR. 1 or CR 2 R 3 ;R 1 R 2 R 3 It is either not connected to adjacent groups or forms a ring through chemical bonds; R 2 With R 3 They are either not connected or connected in a loop; R 1 R 2 R 3 Each is independently selected from one of the following: unsubstituted or R”-substituted C1-C20 chain alkyl, unsubstituted or R”-substituted C3-C20 cycloalkyl, unsubstituted or R”-substituted C6-C60 aryl, and unsubstituted or R”-substituted C3-C60 heteroaryl; "R" is selected from any one or a combination of two of the following: deuterium, halogen, cyano, amino, C2-C20 alkenyl, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 thioalkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C6-C60 aryl, and C3-C60 heteroaryl.

4. The organic compound according to claim 1, characterized in that, The rings Ar3, Ar4, Ar5, Ar6, Ar7, and Ar8 each independently represent one of the aromatic rings of C6 to C30 and the heteroaromatic rings of C5 to C30. Preferably, the rings Ar3, Ar4, Ar5, Ar6, Ar7, and Ar8 are each independently selected from benzene rings, naphthyl rings, anthracene rings, fluorene rings, furanyl, benzofuranyl, dibenzofuranyl, indolyl, benzoindolyl, carbazoleyl, indolocarbazoleyl, thiopheneyl, benzothiopheneyl, dibenzothiopheneyl, thiopheneyl, benzoanthrayl, phenanthroyl, pyrene, pyrene, peryl, fluoranyl, tetraphenyl, pentaphenyl, benzopyrene, biphenyl, amphyl, triphenyl, triphenyl, tetraphenyl, diphenyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, Pyrroleyl, isoindolyl, carbazoleyl, indoxcarbazoleyl, pyridyl, quinolinyl, isoquinolinyl, acridineyl, phenanthridineyl, benzo-5,6-quinolinyl, benzo-6,7-quinolinyl, benzo-7,8-quinolinyl, pyrazolyl, indazoleyl, imidazolyl, benzimidazoleyl, naphthimidazoleyl, phenanthridinemidazoleyl, pyridinimidazoleyl, pyrazinimidazoleyl, quinoxalinimidazoleyl, oxazolyl, benzooxazolyl, naphthimidazoleyl, anthraquinoxazolyl, phenanthridinemidazoleyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl; More preferably, the rings Ar3, Ar4, Ar5, Ar6, Ar7, and Ar8 are each independently selected from one of the following: benzene ring, naphthyl ring, anthracene ring, fluorene ring, furanyl, benzofuranyl, dibenzofuranyl, indolyl, benzoindolyl, carbazoyl, indolocarbazoyl, benzothiophenyl, dibenzothiophenyl, thiophenyl, and pyridyl. More preferably, the rings Ar3, Ar4, Ar5, and Ar6 are each independently selected from a benzene ring, and the rings Ar7 and Ar8 are each independently selected from a benzene ring or a pyridyl group.

5. The organic compound according to claim 1, characterized in that, It has the structure shown in equation (2): The definitions of ring Ar1, ring Ar2, R1, R2, R3, R4, R5, R6, R7, R8, n1, n2, n3, n4, n5, n6, n7, n8, X1, X2, W1, and m1 are the same as those in claim 1. X1 connects the structure shown in formula (Z3) or formula (Z2), and X2 connects the structure shown in formula (Z3) or formula (Z2), where "*" represents the connection site; When X1 and / or X2 in equation (2) are independently connected to equation (Z3), when X1 and X2 are B, Y1 is N; when X1 and X2 are independently C or Si, Y1 is C. Preferably, m1 is 1, and W1 is independently selected from carbon-carbon single bonds, O, and S; More preferably, m1 is 1, and W1 is selected from carbon-carbon single bonds.

6. The organic compound according to claim 5, characterized in that, X1 and X2 are both C, or X1 and X2 are both Si, or X1 and X2 are both B; Preferably, X1 and X2 are the same, X1 is connected to the structure shown in (Z3), and X2 is connected to the structure shown in (Z3); or, X1 and X2 are the same, X1 is connected to the structure shown in (Z2), and X2 is connected to the structure shown in (Z2). More preferably, X1 and X2 are both C, X1 is connected in the structure shown in (Z3), and X2 is connected in the structure shown in (Z3); or, X1 and X2 are the same, X1 is connected in the structure shown in (Z2), and X2 is connected in the structure shown in (Z2). More preferably, X1 and X2 are both C, and X1 is connected to the structure shown in formula (Z3), while X2 is connected to the structure shown in formula (Z3).

7. The organic compound according to claim 3, characterized in that, It has a structure shown in any of the following equations (3-1), (3-2), (3-3), and (3-4): Among them, the definitions of ring Ar1, ring Ar2, R1, R2, R3, R4, R5, R6, R7, R8, n1, n2, n3, n4, n5, n6, n7, and n8 are the same as those in equations (1) and (Z1); R9 and R 10 The definition ranges of n7 and n8 are the same as those of R7 and R8; the definition ranges of n9 and n10 are the same as those of n7 and n8. Preferably, the ring Ar1 and the ring Ar2 are each independently selected from the structure shown in formula (a) or formula (b); More preferably, ring Ar1 and ring Ar2 are both structures shown in formula (a), or ring Ar1 and ring Ar2 are both structures shown in formula (b); Most preferably, both ring Ar1 and ring Ar2 have the structure described in formula (a).

8. The organic compound according to claim 7, characterized in that, It has a structure shown in any of the following equations (4-1), (4-2), and (4-3): Among them, R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 The definitions of n1, n2, n3, n4, n5, n6, n7, n8, n9 and n10 are the same as those in equation (3-1).

9. The organic compound according to any one of claims 1, 5, 7 or 8, wherein R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 Each of the following is independently selected from hydrogen, deuterium, halogen, cyano, amino, R'-substituted or unsubstituted C1-C10 chain alkyl, R'-substituted or unsubstituted C3-C10 cycloalkyl, R'-substituted or unsubstituted C1-C10 alkoxy, R'-substituted or unsubstituted C2-C10 aliphatic chain alkylamine, R'-substituted or unsubstituted C4-C30 cycloaliphatic chain alkylamine, R'-substituted or unsubstituted C6-C30 arylamine, R'-substituted or unsubstituted C3-C30 heteroarylamine, R'-substituted or unsubstituted C6-C30 aryloxy, R'-substituted or unsubstituted C6-C30 arylboryl, R'-substituted or unsubstituted C6-C30 aryl, and R'-substituted or unsubstituted C3-C60 heteroaryl; and R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 Each of the corresponding ring structures is connected by a single bond or by fused bonding. The two adjacent R's mentioned above are either not connected or connected to form a ring; each R' is independently selected from one or a combination of two of the following: deuterium, halogen, cyano, amino, C2-C10 alkenyl, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C8 alkoxy, C1-C8 thioalkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C6-C30 arylboryl, C6-C30 aryl, and C3-C30 heteroaryl. Preferably, R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 Each of the following groups is independently selected from hydrogen, deuterium, cyano, halogen, amino, or a combination of two of the following substituents: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, phenyl, naphthyl, anthracene, benzo[a]anthrayl, phenanthrene, benzo[a]phenanthrene, pyrene, pyryl, peryl, fluoranyl, tetraphenyl, pentaphenyl, benzo[a]pyrene, biphenyl, amphylphenyl, terphenyl, triphenyl, tetraphenyl Fiberyl, spirodifluorenyl, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis or trans indofluorenyl, trimerinyl, isotrimericininyl, spirotrimericininyl, spiroisotrimericininyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thiopheneyl, benzothiopheneyl, isobenzothiopheneyl, dibenzothiopheneyl, pyrroleyl, isoindoleyl, carbazoleyl, indocarbazoleyl, pyridinyl, quinolinyl, isoquinolinyl, acridineyl, phenanthridineyl, benzo-5,6-quinolinyl, benzo-6,7-quinolinyl, benzo-7,8-quinolinyl, pyrazolyl, indazoleyl, imidazoleyl, benzimidazoleyl, naphthizimidazoleyl, phenanthrenezimidazoleyl, pyridinium-imidazolyl, pyridinium-imidazolyl Zizaimidazole, quinoxalinzimidazole, oxazolyl, benzoxoxazolyl, naphthoxoxazolyl, anthraquinoxazolyl, phenanthoxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazaanthrayl, 2,7-diazapyrene, 2,3-diazapyrene, 1,6-diazapyrene, 1,8-diazapyrene, 4,5-diazapyrene, 4,5,9,10-tetraazaperyl, pyrazinyl, phenazinyl, phenthiazinyl, naphridinyl, azacarbazolyl, benzocarbazolyl, phenanthrolinel, 1,2,3-triazolyl, 1,2,4-triazolyl Benzotriazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,3-triazinyl, tetrazolyl, 1,2,4,5-tetraazinyl, 1,2,3,4-tetraazinyl, 1,2,3,5-tetraazinyl, purinyl, pteridyl, inazinyl, benzothiadiazolyl, 9,9-dimethylacridyl, triarylamine, adamantyl, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl or methoxy; More preferably, R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 Each of the following groups is independently selected from hydrogen, deuterium, cyano, halogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, 2-methylbutyl, trifluoromethyl, pentafluoroethyl, phenyl, naphthyl, anthracene, benzo[a]anthrayl, phenanthrene, benzo[a]phenanthrene, pyrene, tetraphenyl, pentaphenyl, benzo[a]pyrene, biphenyl, terphenyl, triphenyl, fluorenyl, spirodifluorenyl, furanyl, benzo[a]furanyl, isobenzo[a]furanyl, dibenzo[a]furanyl, thiophene, benzo[a]thiophene, isobenzo[a]thiophene, dibenzo[a]thiophene, pyrrole, isoindole, carbazole, indoxacarbazole, pyridinyl, quinolinyl, isoquinolinyl, pyrazolyl, indazole, imidazolyl, pyridazinyl, pyrimidinyl Benzopyrimidinyl, quinoxalinyl, pyrazinyl, phenazinyl, phenothiazinyl, naphridinyl, azacarbazoyl, benzocarbazoyl, phenanthrolinel, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, 1,2,3-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,3-triazinyl, tetrazolyl, 1,2,4,5-tetraazinyl, inazinyl, benzothiadiazolyl, 9,9-dimethylacridinyl, triarylamine, adamantyl, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl, or methoxy.

10. The compound according to claim 1, wherein the compound is selected from the following specific structural compounds:

11. The application of the compound according to any one of claims 1-10 as a functional material in an organic electronic device, wherein the organic electronic device is an organic electroluminescent device, an optical sensor, a solar cell, an organic thin-film transistor, or an organic field-effect transistor; Furthermore, the compound is used as a light-emitting layer material in organic electroluminescent devices, specifically as a light-emitting material in the light-emitting layer.

12. An organic electroluminescent device, comprising a substrate, and an anode layer, a plurality of light-emitting functional layers, and a cathode layer sequentially formed on the substrate; wherein the light-emitting functional layers include a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer, wherein the hole injection layer is formed on the anode layer, the hole transport layer is formed on the hole injection layer, the cathode layer is formed on the electron transport layer, and a light-emitting layer is located between the hole transport layer and the electron transport layer, wherein the light-emitting layer contains a compound according to any one of claims 1-10.

13. A display device comprising the organic electroluminescent device of claim 12.

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