Organic compound, application thereof and organic electroluminescent device containing organic compound

Abstract

The invention relates to an organic compound, application of the compound and an organic electroluminescent device containing the compound. The organic compound has a structure as shown in a formula (1), ring A, ring B, ring C, ring D, ring E, ring F, ring G, ring H, ring I, ring J and ring K independently represent one of C5-C20 aromatic rings and C4-C20 heteroaromatic rings, X and Y are independently selected from C or Si, W1, W2 and W3 are independently selected from a single bond, O, CO, SO2, S, NR1, CR2R3 or SiR4R5, and m1, m2 and m3 are independently 0 or 1. After the compound is prepared and applied to the organic electroluminescent device, the device has good performance of high color purity and high luminous efficiency, meanwhile, low-efficiency roll-off of the electroluminescent device is achieved, and the service life of the device is extremely long. # imgabs0 #

Description

Technical Field

[0001] The present invention relates to the technical field of organic electroluminescence, and particularly relates to an organic compound, and also relates to the application of such a light-emitting material and an organic electroluminescent device comprising the compound. Background Art

[0002] An organic light-emitting device (OLED: Organic Light Emitting Diodes) is a device having a sandwich-like structure, including positive and negative electrode film layers and an organic functional material layer sandwiched between the electrode film layers. A voltage is applied to the electrodes of the OLED device, positive charges are injected from the positive electrode, negative charges are injected from the negative electrode, and under the action of an electric field, the positive and negative charges migrate and meet in the organic layer to recombine and emit light. Since OLED devices have the advantages of high brightness, fast response, wide viewing angle, simple process, flexibility, etc., they have attracted much attention in the fields of new display technology and new lighting technology. At present, this technology has been widely applied to the display panels of new lighting lamps, smart phones, tablet computers and other products, and will further expand to the application fields of large-size display products such as televisions. It is a new display technology with rapid development and high technical requirements.

[0003] In the selection of OLED light-emitting materials, fluorescent materials with singlet emission have good lifetimes and low prices, but low efficiencies; phosphorescent materials with triplet emission have high efficiencies, but high prices, and the lifetime problem of blue light materials has not been solved. Adachi of Kyushu University in Japan proposed a new type of organic light-emitting material, namely thermally activated delayed fluorescence (TADF) materials. This type of material utilizes the separation of donors and acceptors to obtain a small singlet-triplet energy gap (ΔE ST , ,

[0005] , ,

[0004] )(<0.3 eV), so that triplet excitons can be converted into singlet excitons through reverse intersystem crossing (RISC) to emit light, and thus the internal quantum efficiency of the device can reach 100%.

[0004] With the development of technology, in order to meet the BT.2020 standard issued by the Radiocommunication Sector of the International Telecommunication Union (ITU-R) for the new generation of ultra-high definition (UHD) video production and display systems, for light-emitting materials, in addition to high efficiency and long lifetime, a narrower full width at half maximum is also required to achieve higher color purity. Currently, the full width at half maximum of commercially available OLED materials is usually relatively wide (>40 nm). Although the color purity can also be improved by an optical filter, it will lead to a decrease in brightness and efficiency, which is not worth the loss.

[0005] In recent years, novel MR-TADF OLED materials based on multiple resonance (MR) have simultaneously combined the advantages of high efficiency and narrow spectra, and have become a research hotspot in the field of organic electroluminescence. Summary of the Invention

[0006] To solve the above technical problems, the present invention provides an organic compound, and such compounds have extremely long stability. The specific technical solution is as follows:

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

[0008]

[0009] In formula (1), ring A, ring B, ring C, ring D, ring E, ring F, ring G, ring H, ring I, ring J, and ring K each independently represent an aromatic ring having 5 to 20 carbon atoms or a heteroaromatic ring having 4 to 20 carbon atoms;

[0010] W1, W2, and W3 each independently selected from a single bond, O, CO, SO2, S, NR1, CR2R3, or SiR4R5; m1, m2, and m3 are each independently 0 or 1;

[0011] The R1, R2, R3, R4, and R5 are not connected to the adjacent group or are connected to form a ring; R2 and R3 are not connected to each other or are connected to form a ring; R4 and R5 are not connected to each other or are connected to form a ring;

[0012] The X and Y are each independently selected from C or Si;

[0013] The R1, R2, R3, R4, and R5 are each independently selected from one of the following unsubstituted or R'-substituted groups: a linear alkyl group having 1 to 36 carbon atoms, a cycloalkyl group having 3 to 36 carbon atoms, an arylamino group having 6 to 30 carbon atoms, an aryl group having 6 to 60 carbon atoms, an aryloxy group having 6 to 60 carbon atoms, and a heteroaryl group having 5 to 60 carbon atoms;

[0014] The R a 、R b 、R c 、R d 、R e 、R f 、R g 、R h 、R i 、R j 、R k respectively independently represent a single substituent to the maximum allowable number of substituents;

[0015] The R a 、R b 、R c 、R d 、R e 、R f 、R g 、R h 、Ri , R j , R k Each independently is connected to the connected ring structure by a single bond or a fused bond. The R a , R b , R c , R d , R e , R f , R g , R h , R i , R j , R k There is no connection or they are connected to form a ring between two adjacent ones among them;

[0016] R a , R b , R c , R d , R e , R f , R g , R h , R i , R j , R k Each independently is selected from the group consisting of hydrogen, deuterium, halogen, carbonyl, carboxyl, nitro, cyano, amino, or one of the following unsubstituted or R'-substituted groups: linear alkyl of C1-C36, cycloalkyl of C3-C36, alkoxy of C1-C10, thioalkoxy of C1-C10, alkylsilyl of C1-C10, alkylamino of C1-C10, arylamino of C6-C30, heteroarylamino of C3-C30, aryl of C6-C60, aryloxy of C6-C60, heteroaryl of C5-C60;

[0017] There is no connection or they are connected by a chemical bond between two adjacent R's; R' is selected from the group consisting of deuterium, halogen, cyano, amino, alkenyl of C2-C10, linear alkyl of C1-C10, cycloalkyl of C3-C10, alkoxy of C1-C10, thioalkoxy of C1-C10, alkylsilyl of C1-C10, alkylamino of C1-C10, arylamino of C6-C60, heteroarylamino of C3-C60, aryloxy of C6-C30, aryl of C6-C60, heteroaryl of C3-C60, or a combination of one or two of them.

[0018] Preferably, in formula (1), the ring A, ring B, ring C, ring D, ring E, ring F, ring G, ring H, ring I, ring J, ring K are each independently a structure represented by formula (a) or formula (b). The dashed double bond represents the fused position of the following group in formula (1):

[0019]

[0020] In formula (a), Z 1 , Z 2 , Z 3 , Z 4 are each independently selected from CR 1 or N, and two adjacent Rs 1 are not connected or are connected by a chemical bond to form a ring;

[0021] R 1 are each independently selected from hydrogen, deuterium, cyano, halogen, amino, unsubstituted or R”-substituted C1-C20 linear alkyl, unsubstituted or R”-substituted C3-C20 cycloalkyl, unsubstituted or R”-substituted C1-C20 alkoxy, unsubstituted or R”-substituted C1-C20 alkylsilyl, unsubstituted or R”-substituted C1-C20 alkylamino, unsubstituted or R”-substituted C6-C30 arylamino, unsubstituted or R”-substituted C3-C30 heteroarylamino, unsubstituted or R”-substituted C6-C30 aryloxy, unsubstituted or R”-substituted C3-C30 heteroaryloxy, unsubstituted or R”-substituted C6-C60 aryl, unsubstituted or R”-substituted C3-C60 heteroaryl;

[0022] In formula (b), Z is selected from O, S, NR 2 or CR 3 R 4 ; R 2 , R 3 , R 4 are not connected to the adjacent groups or are connected by a chemical bond to form a ring; R 3 and R 4 are not connected or are connected to form a ring;

[0023] R 2 , R 3 , R 4 are each independently selected from unsubstituted or R”-substituted C1-C20 linear alkyl, unsubstituted or R”-substituted C3-C20 cycloalkyl, unsubstituted or R”-substituted C6-C60 aryl, unsubstituted or R”-substituted C3-C60 heteroaryl;

[0024] R” is selected from deuterium, halogen, cyano, amino, C2-C20 alkenyl, C1-C20 linear 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, C3-C60 heteroaryl, or any combination of one or two of these;

[0025] Preferably, Z is selected from O, S or NR 2。

[0026] Continuing preferably, one of the rings A, B, C, D, E, F, G, H, I, J, and K is a structure represented by formula (b), and the other ring structures are each independently a structure represented by formula (a) or (b);

[0027] Preferably, in formula (a) and formula (b), the R 1 , R 2 , R 3 , R 4 are each independently selected from hydrogen, deuterium, cyano, halogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, 2-methylbutyl, trifluoromethyl, pentafluoroethyl, phenyl, naphthyl, anthryl, benzanthryl, phenanthryl, benzophenanthryl, pyrenyl, tetraphenyl, pentaphenyl, benzopyrenyl, biphenyl, terphenyl, quaterphenyl, fluorene, spirobifluorene, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, furyl, benzofuryl, isobenzofuryl, dibenzofuryl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indolocarbazolyl, pyridyl, quinolinyl, isoquinolinyl, acridinyl, phenanthridinyl, benzo-5,6-quinolinyl, benzo-6,7-quinolinyl, benzo-7,8-quinolinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthimidazolyl, phenanthrimidazolyl, pyridinimidazolyl, pyrazinimidazolyl, quinoxalinimidazolyl, oxazolyl, benzoxazolyl, naphthoxazolyl, anthroxazolyl, phenanthroxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazaanthracenyl, 2,7-diazapyrenyl, 2,3-diazapyrenyl, 1,6-diazapyrenyl, 1,8-diazapyrenyl, 4,5-diazapyrenyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarbazolyl, phenanthroline, 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-tetrazinyl, indolizinyl, benzothiadiazolyl, 9,9-dimethylacridinyl, triarylamine, adamantane, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl or methoxy.

[0028] Further, in formula (1), each of ring A, ring B, ring C, ring D, ring E, ring F, ring G, ring H, ring I, ring J, and ring K independently represents an aromatic ring having 5 to 12 carbon atoms or a heteroaromatic ring having 4 to 10 carbon atoms; preferably, each of ring A, ring B, ring C, ring D, ring E, ring F, ring G, ring H, ring I, ring J, and ring K independently represents an aromatic ring having 6 to 12 carbon atoms; more preferably, each of ring A, ring B, ring C, ring D, ring E, ring F, ring G, ring H, ring I, ring J, and ring K independently is selected from any one of a benzene ring, a naphthalene ring, or a fluorene ring; even more preferably, each of ring A, ring B, ring C, ring D, ring E, ring F, ring G, ring H, ring I, ring J, and ring K independently is selected from a benzene ring.

[0029] Further, in formula (1), m3 is 0, and each of m1 and m2 independently is 0 or 1; each of W1 and W2 independently is selected from a single bond, O, CO, SO2, S, NR1, CR2R3, or SiR4R5;

[0030] Preferably, m3 is 0, and each of m1 and m2 independently is 0 or 1; each of W1 and W2 independently is selected from a single bond, CO, NR1, or CR2R3; more preferably, m3 is 0, and each of m1 and m2 independently is 0 or 1; both W1 and W2 are selected from a single bond.

[0031] In the present invention, the "substituted or unsubstituted" group may be substituted with one substituent or may be substituted with multiple substituents. When there are multiple substituents, they may be selected from different substituents. When the same expression is involved in the present invention, it has the same meaning, and the selection range of the substituents is as shown above and will not be elaborated one by one.

[0032] In this specification, the expression of Ca~Cb represents that the group has a carbon atom number of a~b. Unless otherwise specified, generally, the carbon atom number does not include the carbon atom number of the substituent.

[0033] In this specification, the expression of a ring structure with a "-" drawn across it indicates that the connection site is at any position on the ring structure where a bond can be formed.

[0034] In this specification, "independently" means that when the subject has multiple ones, they can be the same or different from each other.

[0035] In the present invention, for the expression of chemical elements, unless otherwise specified, it usually includes the concept of its isotopes. For example, the expression of "hydrogen (H)" includes the concepts of its isotopes 1H (protium or H), 2H (deuterium or D); carbon (C) includes 12C, 13C, etc., and will not be elaborated further.

[0036] The heteroatoms in the present invention generally refer to atoms or atomic groups selected from N, O, S, P, Si, and Se, preferably selected from N, O, and S.

[0037] In the present specification, examples of the halogen include fluorine, chlorine, bromine, iodine, etc.

[0038] In the present invention, unless otherwise specified, both aryl and heteroaryl include monocyclic groups and fused-ring groups.

[0039] In the present invention, the expression "connected by a single bond or fused" generally means that the substituent group is directly connected to the parent nucleus structure by a single bond, or that the substituent group is fused to the parent nucleus structure to form a fused-ring aromatic hydrocarbon structure with multiple aromatic rings sharing a common edge. Here, the aromatic rings include six-membered aromatic rings such as benzene rings, and also include five-membered and six-membered heteroaromatic rings containing atoms such as N, O, or S.

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

[0041] The C3-C60 can all be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, C48, C50, C52, C54, C56, or C58, etc.

[0042] The 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.

[0043] The C3-C20 can all be C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, or C19, etc.

[0044] The C6-C30 can all be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, or C28, etc.

[0045] The C3-C30 can all be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, or C28, etc.

[0046] Any of C2-C10 may be C2, C3, C4, C5, C6, C7, C8, C9 or C10.

[0047] In the present invention, the substituted or unsubstituted C6-C60 aryl group (or C6-C50 aryl group) includes monocyclic aryl groups and polycyclic aryl groups, preferably C6-C30 aryl groups, and more preferably C6-C20 aryl groups. The so-called monocyclic aryl group means that the molecule contains at least one phenyl group. When the molecule contains at least two phenyl groups, the phenyl groups are independent of each other and are connected by single bonds. Exemplarily, such as: phenyl group, biphenyl group, terphenyl group, etc. Specifically, the biphenyl group includes 2-biphenyl group, 3-biphenyl group and 4-biphenyl group; the terphenyl group includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl. The polycyclic aryl group means that the molecule contains at least two aromatic rings, and the aromatic rings are not independent of each other but are fused to each other by sharing two adjacent carbon atoms. Exemplarily, such as: naphthyl group, anthryl group, phenanthryl group, indenyl group, fluorenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, perylenyl group, -yl group, tetraphenylenyl group and their derivative groups, etc. The naphthyl group includes 1-naphthyl group or 2-naphthyl group; the anthryl group is selected from 1-anthryl group, 2-anthryl group and 9-anthryl group; the fluorenyl group is selected from 1-fluorenyl group, 2-fluorenyl group, 3-fluorenyl group, 4-fluorenyl group and 9-fluorenyl group; the pyrenyl group is selected from 1-pyrenyl group, 2-pyrenyl group and 4-pyrenyl group; the tetraphenylenyl group is selected from 1-tetraphenylenyl group, 2-tetraphenylenyl group and 9-tetraphenylenyl group. The derivative groups of fluorene are selected from 9,9-dimethylfluorenyl group, 9,9-diethylfluorenyl group, 9,9-dipropylfluorenyl group, 9,9-dibutylfluorenyl group, 9,9-dipentylfluorenyl group, 9,9-dihexylfluorenyl group, 9,9-diphenylfluorenyl group, 9,9-dinaphthylfluorenyl group, 9,9'-spirobifluorenyl group and benzofluorenyl group.

[0048] The C3-C60 heteroaryl (or C6-C50 heteroaryl) mentioned in the present invention includes monocyclic heteroaryl and fused-ring heteroaryl, preferably C3-C30 heteroaryl, more preferably C4-C20 heteroaryl, and even more preferably C5-C12 heteroaryl. Monocyclic heteroaryl refers to a molecule containing at least one heteroaryl. When the molecule contains one heteroaryl and other groups (such as aryl, heteroaryl, alkyl, etc.), the heteroaryl and other groups are independent of each other and are connected by a single bond. Examples of monocyclic heteroaryl include, for example, furyl, thienyl, pyrrolyl, pyridyl, etc. Fused-ring heteroaryl refers to a group in which the molecule contains at least one aromatic heterocycle and an aromatic ring (aromatic heterocycle or aromatic ring), and the two are not independent of each other but are fused to each other by sharing two adjacent atoms. Examples of fused-ring heteroaryl include: benzofuryl, benzothienyl, isobenzofuryl, indolyl, dibenzofuryl, dibenzothienyl, carbazolyl, acridinyl, isobenzofuryl, isobenzothienyl, benzocarbazolyl, azacarbazolyl, phenothiazinyl, phenazinyl, 9-phenylcarbazolyl, 9-naphthylcarbazolyl, dibenzocarbazolyl, indolocarbazolyl, etc.

[0049] Specific examples of the arylene in the present invention can be a divalent group obtained by removing one hydrogen atom from the examples of the above-mentioned aryl. The number of carbon atoms in the arylene includes, but is not limited to, C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc. Specific examples of the heteroarylene in the present invention can be a divalent group obtained by removing one hydrogen atom from the examples of the above-mentioned heteroaryl.

[0050] The aryloxy or heteroaryloxy in the present invention can be a monovalent group formed by the above-mentioned aryl or heteroaryl and oxygen.

[0051] In the present invention, arylamino represents a group formed by substituting one or two hydrogens on the amino group with aryl, wherein the connection site of the arylamino can be connected to the aryl in the arylamino or to the N in the arylamino, and the exemplary number of carbon atoms and specific groups of the aryl in the arylamino are the same as those above.

[0052] Examples of the C6-C30 arylamino mentioned in the present invention include, for example, phenylamino, methylphenylamino, naphthylamino, anthrylamino, phenanthrylamino, biphenylamino, etc.

[0053] Examples of the C3-C30 heteroarylamino mentioned in the present invention include, for example, pyridylamino, pyrimidinylamino, dibenzofurylamino, etc.

[0054] The chain alkyl group mentioned in the present invention, unless otherwise specified, includes straight-chain alkyl groups and branched-chain alkyl groups. Specifically, the substituted or unsubstituted C1-C30 chain alkyl group is preferably a substituted or unsubstituted C1-C16 chain alkyl group, and more preferably a substituted or unsubstituted C1-C10 chain alkyl group. Examples of the substituted or unsubstituted C1-C10 chain alkyl group 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, and 2-ethylhexyl.

[0055] In the present invention, the cycloalkyl group includes a monocycloalkyl group and a polycycloalkyl group; wherein, a monocycloalkyl group refers to an alkyl group containing a single cyclic structure; a polycycloalkyl group refers to a structure composed of two or more cycloalkyl groups sharing one or more carbon atoms on the ring; the C3-C20 cycloalkyl group can be exemplified by cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, etc.

[0056] In the present specification, the substituted or unsubstituted C1-C20 alkoxy group is preferably a substituted or unsubstituted C1-C10 alkoxy group. Examples of the C1-C20 alkoxy group include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, pentyloxy, isopentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, etc., among which methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy, sec-butoxy, isobutoxy, isopentyloxy, and methoxy is more preferred.

[0057] In the present specification, as the substituted or unsubstituted C1-C20 silyl group, as the substituted or unsubstituted C1-C10 silyl group, examples of the C1-C10 silyl group can be a silyl group substituted by the groups exemplified in the above-mentioned C1 to C10 chain alkyl group, specifically including: methylsilyl, dimethylsilyl, trimethylsilyl, ethylsilyl, diethylsilyl, triethylsilyl, tert-butyldimethylsilyl, tert-butyldiphenylsilyl and the like.

[0058] In the present specification, the C2-C20 alkenyl group, preferably the C2-C10 alkenyl group, is a hydrocarbon group containing at least one C=C double bond, and illustratively includes but is not limited to: vinyl, propenyl, allyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, butadienyl, pentadienyl, etc.

[0059] It should be noted that in the present application, for the convenience of description, the possible functions of each group / feature are described separately, but this does not mean that these groups / features act independently. In fact, the reason for obtaining good performance is essentially the optimized combination of the entire molecule, which is the result of the synergistic effect between various groups, rather than the effect of a single group.

[0060] Furthermore, the compound of the present invention has the structure shown in the following formula (2):

[0061]

[0062] Wherein, R a , R b , R c , R d , R e , R f , R g , R h , R i , R j , R k , X, Y, W1, W2, m1, m2 are all defined in the same way as in formula (1);

[0063] Further preferably, m1 and m2 are respectively 1, W1 and W2 each independently represent a single bond, CO, NR1 or CR2R3, and R1, R2, R3 are not connected to the adjacent ring or are connected by a single bond; R2 and R3 are not connected or are connected to form a ring;

[0064] Or preferably, one of m1 and m2 is 0 and the other is 1, W1 and W2 represent a single bond, CO, NR1 or CR2R3, and R1, R2, R3 are not connected to the adjacent ring or are connected by a single bond; R2 and R3 are not connected or are connected to form a ring;

[0065] More preferably, m1 and m2 are respectively 1, and W1 and W2 both represent a single bond.

[0066] Furthermore, the compound of the present invention has the structures shown in the following formula (2-1), (2-2) and (2-3):

[0067]

[0068]

[0069] Wherein, R a , R b , R c , R d , R e , R f , Rg , R h , R i , R j , R k are all defined in the same way as in formula (1);

[0070] Preferably, it has the structure shown in formula (2-1).

[0071] In the above general formula of the present invention, preferably, the R a , R b , R c , R d , R e , R f , R g , R h , R i , R j , R k are each independently selected from hydrogen, deuterium, halogen, cyano or one of the following groups which are unsubstituted or substituted by R': C1-C6 linear alkyl, C3-C6 cycloalkyl, C1-C6 alkoxy, C1-C6 thioalkoxy, C6-C20 arylamino, C3-C20 heteroarylamino, C6-C30 aryl, C6-C30 aryloxy, C5-C30 heteroaryl;

[0072] R' is selected from one of deuterium, halogen, cyano, amino, C1-C6 linear alkyl, C3-C6 cycloalkyl, C1-C6 alkoxy, C1-C6 thioalkoxy, C1-C6 alkylsilyl, C1-C6 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C6-C30 aryl, C3-C30 heteroaryl

[0073] Preferably, the R a , R b , R c , R d , R e , R f , R g , R h , R i , R j , R kIndependently selected from one or a combination of two of hydrogen, deuterium, cyano, halogen, or the following substituted groups: 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, anthryl, benzanthryl, phenanthryl, benzophenanthryl, pyrenyl, chrysenyl, perylenyl, fluoranthenyl, tetraphenyl, pentaphenyl, benzopyrenyl, biphenyl, azobenzene, terphenyl, triphenyl, tetraphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis- or trans-indeno[1,2-b]fluoranthenyl, truxenyl, isotruxenyl, spirotruxenyl, spiroisotruxenyl, furyl, benzofuryl, isobenzofuryl, dibenzofuryl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indolocarbazolyl, pyridyl, quinolinyl, isoquinolinyl, acridinyl, phenanthridinyl, benzo[5,6]quinolinyl, benzo[6,7]quinolinyl, benzo[7,8]quinolinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthimidazolyl, phenanthrimidazolyl, pyridinimidazolyl, pyrazinimidazolyl, quinoxalinimidazolyl, oxazolyl, benzoxazolyl, naphthoxazolyl, anthroxazolyl, phenanthroxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazaanthracenyl, 2,7-diazapyrenyl, 2,3-diazapyrenyl, 1,6-diazapyrenyl, 1,8-diazapyrenyl, 4,5-diazapyrenyl, 4,5,9,10-tetraazaperylenyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarbazolyl, phenanthrolinyl, 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, L2,5-thiadiazolyl, 1,3,4-thiadiazolyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,3-triazinyl, tetrazolyl, 1,2,4,5-tetrazinyl, 1,2,3,4-tetrazinyl, 1,2,3,5-tetrazinyl, purinyl, pteridinyl, indolizinyl, benzothiadiazolyl, 9,9-dimethylacridinyl, triarylamine, adamantane, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl, or methoxy;

[0074] More preferably, the R a , R b , R c , R d , R e , R f , Rg , R h , R i , R j , R k are each independently selected from hydrogen, deuterium, cyano, halogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, 2-methylbutyl, trifluoromethyl, pentafluoroethyl, phenyl, naphthyl, anthryl, benzanthryl, phenanthryl, benzo[a]phenanthryl, pyrenyl, tetracenyl, pentacenyl, benzopyrenyl, biphenyl, terphenyl, quaterphenyl, fluorene, spirobifluorene, furyl, benzofuryl, isobenzofuryl, dibenzofuryl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indolocarbazolyl, pyridyl, quinolinyl, isoquinolinyl, pyrazolyl, indazolyl, imidazolyl, pyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, aza-carbazolyl, benzocarbolinyl, phenanthrolinyl, 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-tetrazinyl, indolizinyl, benzothiadiazolyl, 9,9-dimethylacridinyl, triarylamine, adamantane, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl or methoxy.

[0075] In the above notice of the present invention, preferably, R1, R2, R3, R4, and R5 are each independently selected from hydrogen, deuterium, cyano, halogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, 2-methylbutyl, trifluoromethyl, pentafluoroethyl, phenyl, naphthyl, anthracenyl, benzanthracenyl, phenanthryl, benzophenanthryl, pyrenyl, tetraphenyl, pentaphenyl, benzopyrenyl, biphenyl, terphenyl, quaterphenyl, fluorene, spirobifluorene, furyl, benzofuryl, isobenzofuryl, dibenzofuryl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indolocarbazolyl, pyridyl, quinolinyl, isoquinolinyl, pyrazolyl, indazolyl, imidazolyl, pyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarbazolyl, phenanthroline, 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-tetrazinyl, indolizinyl, benzothiadiazolyl, 9,9-dimethylacridinyl, triarylamine, adamantane, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl, or methoxy.

[0076] Furthermore, the general formula compounds of the present invention may preferably include the following specific structural compounds A1 to A244. These are only representative:

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088] The innovative point in the structural design of this type of compound of the present invention is as follows:

[0089] A carbon atom or a silicon atom is introduced on both sides of the classical boron-nitrogen mother nucleus to form a spirofluorene or silaspirofluorene-like structure, connecting the two benzene rings on both sides, eliminating the repulsion between the original hydrogen atoms, significantly enhancing the rigidity of the molecule, and further reducing the full width at half maximum FWHM (≤25 nm), improving the color purity, and significantly enhancing the efficiency of the corresponding light-emitting device, providing guidance for constructing a new type of narrow-spectrum light-emitting material.

[0090] More importantly, based on the traditional spirofluorene or silaspirofluorene, the present invention replaces the original fluorene and silafuorene structures with carbazole and substituted carbazole structures. The para position of the spiro carbon atom or silicon atom is the N atom of the carbazole. The advantage is that carbazole has strong electron-donating properties. By introducing two such carbazole locking units, the HOMO and LUMO energy levels of the molecule can be significantly increased, thereby effectively suppressing the injection and recombination of electrons thereon, improving the light-emitting efficiency of the device and enhancing the stability of the device.

[0091] At the same time, the compound of the present invention adopts the spatial structure of a spiro atom tetrahedron. The introduction of the spiro atom forms two orthogonal planes at the spiro atom, significantly increasing the distance between molecules, thereby reducing the intermolecular interaction force and inhibiting molecular stacking. In the device, it can reduce the interaction between the host and the dye and between dyes, improving the light-emitting efficiency, lifetime and other properties of the device. Further, by designing the change of the peripheral substituents of the general formula compound of the present invention, the light color can be regulated in the range from blue light to red light, while maintaining the characteristic of a narrow full width at half maximum of luminescence, and the lifetime of the device has been greatly improved.

[0092] The present invention has verified through a large number of experiments that the electroluminescence spectrum of the OLED device prepared by using the compound of the present invention has a narrow full width at half maximum (≤25 nm), showing obvious multiple resonance thermally activated delayed fluorescence characteristics, thus greatly enriching the skeleton system of multiple resonance narrow-spectrum materials, while greatly simplifying the synthesis process and improving the reaction yield; the corresponding electroluminescent device has a low turn-on voltage, high light-emitting efficiency and extremely long service life, can meet the requirements of current panel manufacturing enterprises for high-performance materials, and shows good application prospects in industrialization.

[0093] The second object of the present invention is to provide an application of the compound described in the first object, and the compound is used in an organic electroluminescent device. Preferably, the compound is used as a light-emitting layer material, preferably a light-emitting dye, in the organic electroluminescent device.

[0094] A third object of the present invention is to provide an organic electroluminescent device. Specifically, an embodiment of the present invention provides an organic electroluminescent device, comprising a substrate, and an anode layer, a plurality of light-emitting functional layers, and a cathode layer formed in sequence 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, 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 between the hole transport layer and the electron transport layer; wherein, preferably, the light-emitting layer contains the general formula compound of the present invention shown in any of the above general formula (1), or the light-emitting layer contains at least any one of the above specific compounds A1 to A244. Detailed implementation mode

[0095] The following will take a plurality of synthesis examples as examples to detail the specific preparation methods of the above new compounds of the present invention, but the preparation methods of the present invention are not limited to these synthesis examples.

[0096] All kinds of chemical reagents used in the present invention, such as petroleum ether, tert-butylbenzene, sodium sulfate, toluene, dichloromethane, cesium carbonate, sodium hydride, boron tribromide, tetrahydrofuran, N,N-dimethylformamide, n-butyllithium, reaction intermediates and other basic chemical raw materials are all purchased from Shanghai Titan Technology Co., Ltd. and Xilong Chemical Co., Ltd. The mass spectrometer used to determine the following compounds was measured by a ZAB-HS type mass spectrometer (manufactured by Micromass UK).

[0097] The synthesis method of the compound of the present invention will be briefly described below. First, a polybrominated intermediate I is obtained by nucleophilic substitution and Buchwald–Hartwig reaction. Then, after lithium-halogen exchange with n-butyllithium, nucleophilic addition to an aromatic ketone is carried out, followed by acidification and ring closure, or nucleophilic substitution with an aromatic dichlorosilafluorene to obtain intermediate II. Finally, under the action of tert-butyllithium, electrophilic boration with boron tribromide is carried out to obtain the target compound.

[0098] Synthesis example

[0099] Synthesis of Compound A1 in Example 1

[0100]

[0101] In a two-necked flask, under a nitrogen atmosphere, polybrominated precursor A1-1 (5 mmol) was dissolved in 10 ml of dry tetrahydrofuran, cooled to -78 °C, and a pentane solution of n-butyllithium (1 M, 12 ml) was added. The reaction was carried out at this temperature for 1 hour. Reactant Q1 (12 mmol) was dissolved in 40 ml of dry tetrahydrofuran pre-cooled to -78 °C, and then this solution was slowly injected into the solution of A1-1 at -78 °C. The temperature was slowly raised to room temperature, and the reaction was carried out for 12 hours. After the reaction was completed, a small amount of methanol was added to quench the reaction. The solvent was evaporated under reduced pressure. 100 ml of glacial acetic acid and 10 ml of concentrated hydrochloric acid were added, and then the temperature was raised to reflux. After reacting for 2 hours, it was neutralized with an aqueous solution of saturated sodium carbonate, extracted with dichloromethane and separated, and the organic phase was collected. The organic phase was dried over anhydrous sodium sulfate, then filtered and concentrated. The compound was separated by a silica gel column with petroleum ether:dichloromethane = 5:1 as the eluent to obtain compound A1-2.

[0102] Compound A1-2 (1 mmol) was dissolved in 20 mL of tert-butylbenzene in a sealed tube. After cooling to -78 °C, a pentane solution of tert-butyllithium (1 M, 2.5 mL) was added, and then the temperature was raised to 30 °C and the reaction was carried out for 1 hour. It was cooled to -78 °C again, boron tribromide (3 mmol) was slowly added, and then the temperature was raised to 30 °C and stirring was continued for 1 hour. After cooling to 0 °C, diisopropylethylamine (5 mmol) was added, and then the temperature was raised to 160 °C and the reaction was carried out for 12 hours. The solvent was dried under vacuum, passed through a silica gel column, and petroleum ether:dichloromethane = 10:1 was used as the eluent to obtain the target compound A1 (HPLC analysis purity 99.43%), a yellow solid. MALDI-TOF-MS result: molecular ion peak: 918.30; elemental analysis result: theoretical value: C, 88.89; H, 3.84; B, 1.18; N, 6.10 (%) ; experimental value: C, 88.88; H, 3.85; B, 1.18; N, 6.10 (%).

[0103] Example 2 Synthesis of Compound A3

[0104]

[0105] In a two-necked flask, under a nitrogen atmosphere, polybrominated precursor A3-1 (5 mmol) was dissolved in 10 ml of dry tetrahydrofuran, cooled to -78 °C, and a pentane solution of n-butyllithium (1 M, 12 ml) was added. The reaction was carried out at this temperature for 1 hour. Reactant Q1 (12 mmol) was dissolved in 40 ml of dry tetrahydrofuran pre-cooled to -78 °C, and then this solution was slowly injected into the solution of A3-1 at -78 °C. The temperature was slowly raised to room temperature, and the reaction was carried out for 12 hours. After the reaction was completed, a small amount of methanol was added to quench the reaction. The solvent was evaporated under reduced pressure. 100 ml of glacial acetic acid and 10 ml of concentrated hydrochloric acid were added, and then the temperature was raised to reflux. After reacting for 2 hours, it was neutralized with an aqueous solution of saturated sodium carbonate, extracted and separated with dichloromethane, and the organic phase was collected. The organic phase was dried over anhydrous sodium sulfate, then filtered and concentrated. The compound was separated by a silica gel column with petroleum ether:dichloromethane = 5:1 as the eluent to obtain compound A3-2.

[0106] Compound A3-2 (1 mmol) was dissolved in 20 mL of tert-butylbenzene in a sealed tube. After cooling to -78 °C, a pentane solution of tert-butyllithium (1 M, 2.5 mL) was added, and then the temperature was raised to 30 °C and the reaction was carried out for 1 hour. It was cooled to -78 °C again, boron tribromide (3 mmol) was slowly added, and then the temperature was raised to 30 °C and stirring was continued for 1 hour. After cooling to 0 °C, diisopropylethylamine (5 mmol) was added, and then the temperature was raised to 160 °C and the reaction was carried out for 12 hours. The solvent was dried under vacuum, passed through a silica gel column, and petroleum ether:dichloromethane = 10:1 was used as the eluent to obtain the target compound A3 (HPLC analysis purity 99.52%), a yellow solid. MALDI-TOF-MS results: molecular ion peak: 1142.55; elemental analysis results: theoretical values: C, 88.25; H, 5.91; B, 0.95; N, 4.90 (%) ; experimental values: C, 88.25; H 5.91; B, 0.96; N, 4.89 (%).

[0107] Synthesis of Compound A17 in Example 3

[0108]

[0109] In a two-necked flask, under a nitrogen atmosphere, polybrominated precursor A17-1 (5 mmol) was dissolved in 10 ml of dry tetrahydrofuran, cooled to -78 °C, and a pentane solution of n-butyllithium (1 M, 12 ml) was added. The reaction was carried out at this temperature for 1 hour. Reactant Q1 (12 mmol) was dissolved in 40 ml of dry tetrahydrofuran pre-cooled to -78 °C, and then this solution was slowly injected into the solution of A17-1 at -78 °C. The temperature was slowly raised to room temperature, and the reaction was carried out for 12 hours. After the reaction was completed, a small amount of methanol was added to quench the reaction, the solvent was evaporated under reduced pressure, 100 ml of glacial acetic acid and 10 ml of concentrated hydrochloric acid were added, and then the temperature was raised to reflux. After reacting for 2 hours, it was neutralized with an aqueous solution of saturated sodium carbonate, extracted and separated with dichloromethane, and the organic phase was collected. The organic phase was dried over anhydrous sodium sulfate, then filtered and concentrated. The compound was separated by a silica gel column using petroleum ether:dichloromethane = 5:1 as the eluent to obtain compound A17-2.

[0110] Compound A17-2 (1 mmol) was dissolved in 20 mL of tert-butylbenzene in a sealed tube. After cooling to -78 °C, a pentane solution of tert-butyllithium (1 M, 2.5 mL) was added, and then the temperature was raised to 30 °C and the reaction was carried out for 1 hour. It was cooled to -78 °C again, boron tribromide (3 mmol) was slowly added, and then the temperature was raised to 30 °C and stirring was continued for 1 hour. After cooling to 0 °C, diisopropylethylamine (5 mmol) was added, and then the temperature was raised to 160 °C and the reaction was carried out for 12 hours. The solvent was dried under vacuum, passed through a silica gel column, and petroleum ether:dichloromethane = 15:1 was used as the eluent to obtain the target compound A17 (purity by HPLC analysis 99.07%), a yellow solid. MALDI-TOF-MS results: molecular ion peak: 1130.27; elemental analysis results: theoretical values: C, 84.95; H, 3.48; B, 0.96; N, 4.95; S, 5.67 (%); experimental values: C, 84.95; H, 3.47; B, 0.96; N, 4.95; S, 5.68 (%).

[0111] Synthesis of Compound A27 in Example 4

[0112]

[0113] In a two-necked flask, under a nitrogen atmosphere, polybrominated precursor A27-1 (5 mmol) was dissolved in 10 ml of dry tetrahydrofuran, cooled to -78 °C, and a pentane solution of n-butyllithium (1 M, 12 ml) was added. The reaction was carried out at this temperature for 1 hour. Reactant Q1 (12 mmol) was dissolved in 40 ml of dry tetrahydrofuran pre-cooled to -78 °C, and then this solution was slowly injected into the solution of A27-1 at -78 °C. The temperature was slowly raised to room temperature, and the reaction was carried out for 12 hours. After the reaction was completed, a small amount of methanol was added to quench the reaction. The solvent was evaporated under reduced pressure. 100 ml of glacial acetic acid and 10 ml of concentrated hydrochloric acid were added, and then the temperature was raised to reflux. After reacting for 2 hours, it was neutralized with an aqueous solution of saturated sodium carbonate, extracted and separated with dichloromethane, and the organic phase was collected. The organic phase was dried over anhydrous sodium sulfate, then filtered and concentrated. The compound was separated by a silica gel column using petroleum ether:dichloromethane = 5:1 as the eluent to obtain compound A27-2.

[0114] Compound A27-2 (1 mmol) was dissolved in 20 mL of tert-butylbenzene in a sealed tube. After cooling to -78 °C, a pentane solution of tert-butyllithium (1 M, 2.5 mL) was added, and then the temperature was raised to 30 °C and the reaction was carried out for 1 hour. It was cooled to -78 °C again, boron tribromide (3 mmol) was slowly added, and then the temperature was raised to 30 °C and stirring was continued for 1 hour. After cooling to 0 °C, diisopropylethylamine (5 mmol) was added, and then the temperature was raised to 160 °C and the reaction was carried out for 12 hours. The solvent was dried under vacuum, passed through a silica gel column, and petroleum ether:dichloromethane = 10:1 was used as the eluent to obtain the target compound A27 (HPLC analysis purity 99.45%), a yellow solid. MALDI-TOF-MS results: molecular ion peak: 1189.34; elemental analysis results: theoretical values: C, 86.79; H, 3.73; B, 0.91; N, 5.88; S, 2.69 (%) ; experimental values: C, 86.79; H, 3.73; B, 0.92; N, 5.88; S, 2.68 (%).

[0115] Synthesis of Compound A32 in Example 5

[0116]

[0117] In a two-necked flask, under a nitrogen atmosphere, polybrominated precursor A32-1 (5 mmol) was dissolved in 10 ml of dry tetrahydrofuran, cooled to -78 °C, and a pentane solution of n-butyllithium (1 M, 12 ml) was added. The reaction was carried out at this temperature for 1 hour. Reactant Q1 (12 mmol) was dissolved in 40 ml of dry tetrahydrofuran pre-cooled to -78 °C, and then this solution was slowly injected into the solution of A32-1 at -78 °C. The temperature was slowly raised to room temperature, and the reaction was carried out for 12 hours. After the reaction was completed, a small amount of methanol was added to quench the reaction. The solvent was evaporated under reduced pressure. 100 ml of glacial acetic acid and 10 ml of concentrated hydrochloric acid were added, and then the temperature was raised to reflux. After reacting for 2 hours, it was neutralized with an aqueous solution of saturated sodium carbonate, extracted and separated with dichloromethane, and the organic phase was collected. The organic phase was dried over anhydrous sodium sulfate, then filtered and concentrated. The compound was separated by a silica gel column with petroleum ether:dichloromethane = 3:1 as the eluent to obtain compound A32-2.

[0118] Compound A32-2 (1 mmol) was dissolved in 20 mL of tert-butylbenzene in a sealed tube. After cooling to -78 °C, a pentane solution of tert-butyllithium (1 M, 2.5 mL) was added, and then the temperature was raised to 30 °C and the reaction was carried out for 1 hour. It was cooled to -78 °C again, boron tribromide (3 mmol) was slowly added, and then the temperature was raised to 30 °C and stirring was continued for 1 hour. After cooling to 0 °C, diisopropylethylamine (5 mmol) was added, and then the temperature was raised to 160 °C and the reaction was carried out for 12 hours. The solvent was dried under vacuum, passed through a silica gel column, and petroleum ether:dichloromethane = 5:1 was used as the eluent to obtain the target compound A32 (HPLC analysis purity 99.15%), a yellow solid. MALDI-TOF-MS result: molecular ion peak: 1264.44; elemental analysis result: theoretical value: C, 88.28; H, 4.22; B, 0.85; N, 6.64 (%) ; experimental value: C, 88.28; H, 4.20; B, 0.85; N, 6.66 (%).

[0119] Synthesis of Compound A48 in Example 6

[0120]

[0121] In a two-necked flask, under a nitrogen atmosphere, polybrominated precursor A48-1 (5 mmol) was dissolved in 10 ml of dry tetrahydrofuran, cooled to -78 °C, and a pentane solution of n-butyllithium (1 M, 12 ml) was added. The reaction was carried out at this temperature for 1 hour. Reactant Q1 (12 mmol) was dissolved in 40 ml of dry tetrahydrofuran pre-cooled to -78 °C, and then this solution was slowly injected into the solution of A48-1 at -78 °C. The temperature was slowly raised to room temperature, and the reaction was carried out for 12 hours. After the reaction was completed, a small amount of methanol was added to quench the reaction. The solvent was evaporated under reduced pressure. 100 ml of glacial acetic acid and 10 ml of concentrated hydrochloric acid were added, and then the temperature was raised to reflux. After reacting for 2 hours, it was neutralized with an aqueous solution of saturated sodium carbonate, extracted and separated with dichloromethane, and the organic phase was collected. The organic phase was dried over anhydrous sodium sulfate, then filtered and concentrated. The compound was separated by a silica gel column using petroleum ether:dichloromethane = 5:1 as the eluent to obtain compound A48-2.

[0122] Compound A48-2 (1 mmol) was dissolved in 20 mL of tert-butylbenzene in a sealed tube. After cooling to -78 °C, a pentane solution of tert-butyllithium (1 M, 2.5 mL) was added, and then the temperature was raised to 30 °C and the reaction was carried out for 1 hour. It was cooled to -78 °C again, boron tribromide (3 mmol) was slowly added, and then the temperature was raised to 30 °C and stirring was continued for 1 hour. After cooling to 0 °C, diisopropylethylamine (5 mmol) was added, and then the temperature was raised to 160 °C and the reaction was carried out for 12 hours. The solvent was dried under vacuum, passed through a silica gel column, and petroleum ether:dichloromethane = 15:1 was used as the eluent to obtain the target compound A48 (HPLC analysis purity 99.23%), a yellow solid. MALDI-TOF-MS result: molecular ion peak: 1195.48; elemental analysis result: theoretical value: C, 88.35; H, 4.89; B, 0.90; N, 5.85 (%); experimental value: C, 88.35; H, 4.88; B, 0.90; N, 5.86 (%).

[0123] Synthesis of Compound A60 in Example 7

[0124]

[0125] In a two-necked flask, under a nitrogen atmosphere, polybrominated precursor A60-1 (5 mmol) was dissolved in 10 ml of dry tetrahydrofuran, cooled to -78 °C, and a pentane solution of n-butyllithium (1 M, 12 ml) was added. The reaction was carried out at this temperature for 1 hour. Reactant Q1 (12 mmol) was dissolved in 40 ml of dry tetrahydrofuran pre-cooled to -78 °C, and then this solution was slowly injected into the solution of A60-1 at -78 °C. The temperature was slowly raised to room temperature, and the reaction was carried out for 12 hours. After the reaction was completed, a small amount of methanol was added to quench the reaction. The solvent was evaporated under reduced pressure. 100 ml of glacial acetic acid and 10 ml of concentrated hydrochloric acid were added, and then the temperature was raised to reflux. After reacting for 2 hours, it was neutralized with an aqueous solution of saturated sodium carbonate, extracted and separated with dichloromethane, and the organic phase was collected. The organic phase was dried over anhydrous sodium sulfate, then filtered and concentrated. The compound was separated by a silica gel column with petroleum ether:dichloromethane = 5:1 as the eluent to obtain compound A60-2.

[0126] In a sealed tube, compound A60-2 (1 mmol) was dissolved in 20 mL of tert-butylbenzene, cooled to -78 °C, and a pentane solution of tert-butyllithium (1 M, 2.5 mL) was added. Then the temperature was raised to 30 °C and the reaction was carried out for 1 hour. It was cooled to -78 °C again, boron tribromide (3 mmol) was slowly added, and then the temperature was raised to 30 °C and stirring was continued for 1 hour. After cooling to 0 °C, diisopropylethylamine (5 mmol) was added, and then the temperature was raised to 160 °C and the reaction was carried out for 12 hours. The solvent was dried under vacuum, passed through a silica gel column, and petroleum ether:dichloromethane = 10:1 was used as the eluent to obtain the target compound A60 (purity 99.33% by HPLC analysis), a yellow solid. MALDI-TOF-MS results: molecular ion peak: 1152.44; elemental analysis results: theoretical values: C, 86.44; H, 4.98; B, 0.94; N, 4.86; S, 2.78 (%); experimental values: C, 86.44; H, 4.97; B, 0.95; N, 4.86; S, 2.78 (%).

[0127] Example 8 Synthesis of Compound A64

[0128]

[0129] In a two-necked flask, under a nitrogen atmosphere, polybrominated precursor A64-1 (5 mmol) was dissolved in 10 ml of dry tetrahydrofuran, cooled to -78 °C, and a pentane solution of n-butyllithium (1 M, 12 ml) was added. The reaction was carried out at this temperature for 1 hour. Reactant Q1 (12 mmol) was dissolved in 40 ml of dry tetrahydrofuran pre-cooled to -78 °C, and then this solution was slowly injected into the solution of A64-1 at -78 °C. The temperature was slowly raised to room temperature and the reaction was carried out for 12 hours. After the reaction was completed, a small amount of methanol was added to quench the reaction. The solvent was evaporated under reduced pressure. 100 ml of glacial acetic acid and 10 ml of concentrated hydrochloric acid were added, and then the temperature was raised to reflux. After reacting for 2 hours, it was neutralized with an aqueous solution of saturated sodium carbonate, extracted with dichloromethane, and the organic phase was collected. The organic phase was dried over anhydrous sodium sulfate, then filtered and concentrated. The compound was separated by a silica gel column with petroleum ether:dichloromethane = 5:1 as the eluent to obtain compound A64-2.

[0130] Compound A64-2 (1 mmol) was dissolved in 20 mL of tert-butylbenzene in a sealed tube. After cooling to -78 °C, a pentane solution of tert-butyllithium (1 M, 2.5 mL) was added, and then the temperature was raised to 30 °C and the reaction was carried out for 1 hour. It was cooled to -78 °C again, boron tribromide (3 mmol) was slowly added, and then the temperature was raised to 30 °C and stirring was continued for 1 hour. After cooling to 0 °C, diisopropylethylamine (5 mmol) was added, and then the temperature was raised to 160 °C and the reaction was carried out for 12 hours. The solvent was dried under vacuum, passed through a silica gel column with petroleum ether:dichloromethane = 10:1 as the eluent to obtain the target compound A64 (HPLC analysis purity 99.12%), a yellow solid. MALDI-TOF-MS result: molecular ion peak: 1225.53; elemental analysis result: theoretical value: C, 88.15; H, 5.26; B, 0.88; N, 5.71 (%) ; experimental value: C, 88.16; H, 5.26; B, 0.87; N, 5.71 (%).

[0131] Synthesis of Compound A76 in Example 9

[0132]

[0133] In a two-necked flask, under a nitrogen atmosphere, polybrominated precursor A76-1 (5 mmol) was dissolved in 10 ml of dry tetrahydrofuran, cooled to -78 °C, and a pentane solution of n-butyllithium (1 M, 12 ml) was added. The reaction was carried out at this temperature for 1 hour. Reactant Q1 (12 mmol) was dissolved in 40 ml of dry tetrahydrofuran pre-cooled to -78 °C, and then this solution was slowly injected into the solution of A76-1 at -78 °C. The temperature was slowly raised to room temperature, and the reaction was carried out for 12 hours. After the reaction was completed, a small amount of methanol was added to quench the reaction. The solvent was evaporated under reduced pressure. 100 ml of glacial acetic acid and 10 ml of concentrated hydrochloric acid were added, and then the temperature was raised to reflux. After reacting for 2 hours, it was neutralized with an aqueous solution of saturated sodium carbonate, extracted and separated with dichloromethane, and the organic phase was collected. The organic phase was dried over anhydrous sodium sulfate, then filtered and concentrated. The compound was separated by a silica gel column with petroleum ether:dichloromethane = 5:1 as the eluent to obtain compound A76-2.

[0134] Compound A76-2 (1 mmol) was dissolved in 20 mL of tert-butylbenzene in a sealed tube. After cooling to -78 °C, a pentane solution of tert-butyllithium (1 M, 2.5 mL) was added, and then the temperature was raised to 30 °C and the reaction was carried out for 1 hour. It was cooled to -78 °C again, boron tribromide (3 mmol) was slowly added, and then the temperature was raised to 30 °C and stirring was continued for 1 hour. After cooling to 0 °C, diisopropylethylamine (5 mmol) was added, and then the temperature was raised to 160 °C and the reaction was carried out for 12 hours. The solvent was dried under vacuum, passed through a silica gel column, and petroleum ether:dichloromethane = 15:1 was used as the eluent to obtain the target compound A76 (HPLC analysis purity 99.19%), a yellow solid. MALDI-TOF-MS results: molecular ion peak: 1226.45; elemental analysis results: theoretical values: C, 90.04; H, 4.52; B, 0.88; N, 4.57 (%); experimental values: C, 90.04; H, 4.52; B, 0.87; N, 4.58 (%).

[0135] Synthesis of Compound A93 in Example 10

[0136]

[0137] In a two-necked flask, under a nitrogen atmosphere, polybrominated precursor A93-1 (5 mmol) was dissolved in 10 ml of dry tetrahydrofuran, cooled to -78 °C, and a pentane solution of n-butyllithium (1 M, 12 ml) was added. The reaction was carried out at this temperature for 1 hour. Reactant Q1 (12 mmol) was dissolved in 40 ml of dry tetrahydrofuran pre-cooled to -78 °C, and then this solution was slowly injected into the solution of A93-1 at -78 °C. The temperature was slowly raised to room temperature, and the reaction was carried out for 12 hours. After the reaction was completed, a small amount of methanol was added to quench the reaction. The solvent was evaporated under reduced pressure. 100 ml of glacial acetic acid and 10 ml of concentrated hydrochloric acid were added, and then the temperature was raised to reflux. After reacting for 2 hours, it was neutralized with saturated aqueous sodium carbonate solution, extracted with dichloromethane, and the organic phase was collected. The organic phase was dried over anhydrous sodium sulfate, then filtered and concentrated. The compound was separated by silica gel column chromatography using petroleum ether:dichloromethane = 4:1 as the eluent to obtain compound A93-2.

[0138] Compound A93-2 (1 mmol) was dissolved in 20 mL of tert-butylbenzene in a sealed tube. After cooling to -78 °C, a pentane solution of tert-butyllithium (1 M, 2.5 mL) was added, and then the temperature was raised to 30 °C and the reaction was carried out for 1 hour. It was cooled to -78 °C again, boron tribromide (3 mmol) was slowly added, and then the temperature was raised to 30 °C and stirring was continued for 1 hour. After cooling to 0 °C, diisopropylethylamine (5 mmol) was added, and then the temperature was raised to 160 °C and the reaction was carried out for 12 hours. The solvent was dried under vacuum, passed through a silica gel column, and petroleum ether:dichloromethane = 15:1 was used as the eluent to obtain the target compound A93 (purity by HPLC analysis 99.66%), a yellow solid. MALDI-TOF-MS results: molecular ion peak: 1181.37; elemental analysis results: theoretical values: C, 89.41; H, 3.75; B, 0.91; N, 5.92 (%) ; experimental values: C, 89.41; H, 3.75; B, 0.92; N, 5.91 (%).

[0139] Example 11 Synthesis of Compound A97

[0140]

[0141] In a two-necked flask, under a nitrogen atmosphere, polybrominated precursor A97-1 (5 mmol) was dissolved in 10 ml of dry tetrahydrofuran, cooled to -78 °C, and a pentane solution of n-butyllithium (1 M, 12 ml) was added. The reaction was carried out at this temperature for 1 hour. Reactant Q1 (12 mmol) was dissolved in 40 ml of dry tetrahydrofuran pre-cooled to -78 °C, and then this solution was slowly injected into the solution of A97-1 at -78 °C. The temperature was slowly raised to room temperature, and the reaction was carried out for 12 hours. After the reaction was completed, a small amount of methanol was added to quench the reaction. The solvent was evaporated under reduced pressure. 100 ml of glacial acetic acid and 10 ml of concentrated hydrochloric acid were added, and then the temperature was raised to reflux. After reacting for 2 hours, it was neutralized with an aqueous solution of saturated sodium carbonate, extracted and separated with dichloromethane, and the organic phase was collected. The organic phase was dried over anhydrous sodium sulfate, then filtered and concentrated. The compound was separated by a silica gel column using petroleum ether:dichloromethane = 5:1 as the eluent to obtain compound A97-2.

[0142] In a sealed tube, compound A97-2 (1 mmol) was dissolved in 20 mL of tert-butylbenzene, cooled to -78 °C, and a pentane solution of tert-butyllithium (1 M, 2.5 mL) was added. Then the temperature was raised to 30 °C and the reaction was carried out for 1 hour. It was cooled to -78 °C again, boron tribromide (3 mmol) was slowly added, and then the temperature was raised to 30 °C and stirring was continued for 1 hour. After cooling to 0 °C, diisopropylethylamine (5 mmol) was added, and then the temperature was raised to 160 °C and the reaction was carried out for 12 hours. The solvent was dried under vacuum, passed through a silica gel column, and petroleum ether:dichloromethane = 15:1 was used as the eluent to obtain the target compound A97 (purity by HPLC analysis 99.52%), a yellow solid. MALDI-TOF-MS results: molecular ion peak: 1131.35; elemental analysis results: theoretical values: C, 89.12; H, 3.74; B, 0.95; N, 6.19 (%) ; experimental values: C, 89.12; H, 3.74; B, 0.96; N, 6.18 (%).

[0143] Example 12 Synthesis of Compound A127

[0144]

[0145] In a two-necked flask, under a nitrogen atmosphere, polybrominated precursor A127-1 (5 mmol) was dissolved in 10 ml of dry tetrahydrofuran, cooled to -78 °C, and a pentane solution of n-butyllithium (1 M, 12 ml) was added. The reaction was carried out at this temperature for 1 hour. Reactant Q2 (12 mmol) was dissolved in 40 ml of dry tetrahydrofuran pre-cooled to -78 °C, and then this solution was slowly injected into the solution of A127-1 at -78 °C. The temperature was slowly raised to room temperature, and the reaction was carried out for 12 hours. After the reaction was completed, a small amount of methanol was added to quench the reaction. The solvent was evaporated under reduced pressure, and the compound A127-2 was obtained by passing through a silica gel column using petroleum ether:dichloromethane = 5:1 as the eluent.

[0146] In a sealed tube, compound A127-2 (1 mmol) was dissolved in 20 mL of tert-butylbenzene. After cooling to -78 °C, a pentane solution of tert-butyllithium (1 M, 2.5 mL) was added. Then the temperature was raised to 30 °C and the reaction was carried out for 1 hour. It was cooled to -78 °C again, and boron tribromide (3 mmol) was slowly added. Then it was raised to 30 °C and stirred for another 1 hour. After cooling to 0 °C, diisopropylethylamine (5 mmol) was added. Then the temperature was raised to 160 °C and the reaction was carried out for 12 hours. The solvent was evaporated under vacuum, and the product was purified by silica gel column chromatography using petroleum ether:dichloromethane = 10:1 as the eluent to obtain the target compound A127 (purity 99.37% by HPLC analysis), a yellow solid. MALDI-TOF-MS result: molecular ion peak: 1174.50; elemental analysis result: theoretical values: C, 83.79; H, 5.75; B, 0.92; N, 4.77; Si, 4.78 (%) ; experimental values: C, 83.79; H, 5.75; B, 0.91; N, 4.78; Si, 4.78 (%).

[0147] Example 13 Synthesis of Compound A134

[0148]

[0149] In a two-necked flask under a nitrogen atmosphere, polybromo precursor A134-1 (5 mmol) was dissolved in 10 ml of dry tetrahydrofuran. After cooling to -78 °C, a pentane solution of n-butyllithium (1 M, 12 ml) was added and the reaction was carried out at this temperature for 1 hour. Reactant Q2 (12 mmol) was dissolved in 40 ml of dry tetrahydrofuran pre-cooled to -78 °C, and then this solution was slowly injected into the solution of A134-1 at -78 °C. The temperature was slowly raised to room temperature and the reaction was carried out for 12 hours. After the reaction was completed, a small amount of methanol was added to quench the reaction, and the solvent was evaporated under reduced pressure. The product was purified by silica gel column chromatography using petroleum ether:dichloromethane = 5:1 as the eluent to obtain compound A134-2.

[0150] In a sealed tube, compound A134-2 (1 mmol) was dissolved in 20 mL of tert-butylbenzene. After cooling to -78 °C, a pentane solution of tert-butyllithium (1 M, 2.5 mL) was added. Then the temperature was raised to 30 °C and the reaction was carried out for 1 hour. It was cooled to -78 °C again, and boron tribromide (3 mmol) was slowly added. Then it was raised to 30 °C and stirred for another 1 hour. After cooling to 0 °C, diisopropylethylamine (5 mmol) was added. Then the temperature was raised to 160 °C and the reaction was carried out for 12 hours. The solvent was evaporated under vacuum, and the product was purified by silica gel column chromatography using petroleum ether:dichloromethane = 10:1 as the eluent to obtain the target compound A134 (purity 99.22% by HPLC analysis), a yellow solid. MALDI-TOF-MS result: molecular ion peak: 1280.37; elemental analysis result: theoretical values: C, 84.36; H, 3.85; B, 0.84; N, 6.56; Si, 4.38 (%) ; experimental values: C, 84.36; H, 3.84; B, 0.86; N, 6.55; Si, 4.38 (%).

[0151] Example 14 Synthesis of Compound A170

[0152]

[0153] In a two-necked flask under a nitrogen atmosphere, polybromo precursor A170-1 (5 mmol) was dissolved in 10 ml of dry tetrahydrofuran. After cooling to -78 °C, a pentane solution of n-butyllithium (1 M, 12 ml) was added and the reaction was carried out at this temperature for 1 hour. Reactant Q2 (12 mmol) was dissolved in 40 ml of dry tetrahydrofuran pre-cooled to -78 °C, and then this solution was slowly injected into the solution of A170-1 at -78 °C. The temperature was slowly raised to room temperature and the reaction was carried out for 12 hours. After the reaction was completed, a small amount of methanol was added to quench the reaction, and the solvent was evaporated under reduced pressure. The product was purified by silica gel column chromatography using petroleum ether:dichloromethane = 5:1 as the eluent to obtain compound A170-2.

[0154] In a sealed tube, dissolve compound A170-2 (1 mmol) in 20 mL of tert-butylbenzene. After cooling to -78 °C, add a pentane solution of tert-butyllithium (1 M, 2.5 mL). Then warm the mixture to 30 °C and react for 1 hour. Cool it to -78 °C again, slowly add boron tribromide (3 mmol), and then raise the temperature to 30 °C and continue stirring for 1 hour. After cooling to 0 °C, add diisopropylethylamine (5 mmol), and then raise the temperature to 160 °C and react for 12 hours. Evaporate the solvent under vacuum, pass through a silica gel column, using petroleum ether:dichloromethane = 5:1 as the eluent, to obtain the target compound A170 (purity by HPLC analysis: 99.64%), a yellow solid. MALDI-TOF-MS result: molecular ion peak: 1165.32; elemental analysis result: theoretical values: C, 84.45; H, 3.80; B, 0.93; N, 6.01; Si, 4.82 (%) ; experimental values: C, 84.45; H, 3.80; B, 0.92; N, 6.01; Si, 4.83 (%).

[0155] Example 15 Synthesis of Compound A180

[0156]

[0157] In a two-necked flask, under a nitrogen atmosphere, dissolve the polybromo precursor A180-1 (5 mmol) in 10 mL of dry tetrahydrofuran. Cool to -78 °C and add a pentane solution of n-butyllithium (1 M, 12 mL). React at this temperature for 1 hour. Dissolve reactants Q1 (6 mmol) and Q2 (6 mmol) in 40 mL of dry tetrahydrofuran pre-cooled to -78 °C, and then slowly inject this solution into the solution of A180-1 at -78 °C. Slowly warm to room temperature and react for 12 hours. After the reaction is completed, add a small amount of methanol to quench, evaporate the solvent under reduced pressure, add 100 mL of glacial acetic acid and 10 mL of concentrated hydrochloric acid, and then heat to reflux. After reacting for 2 hours, neutralize with saturated aqueous sodium carbonate solution, extract and separate with dichloromethane and collect the organic phase. Dry the organic phase with anhydrous sodium sulfate, then filter and concentrate the organic phase, and separate the compound by passing through a silica gel column using petroleum ether:dichloromethane = 5:1 as the eluent to obtain compound A180-2. <{

[0158] Dissolve compound A180-2 (1 mmol) in 20 mL of tert-butylbenzene in a sealed tube. After cooling to -78 °C, add a pentane solution of tert-butyllithium (1 M, 2.5 mL). Then, warm the mixture to 30 °C and react for 1 hour. Cool it to -78 °C again, slowly add boron tribromide (3 mmol), and then raise the temperature to 30 °C and continue stirring for 1 hour. After cooling to 0 °C, add diisopropylethylamine (5 mmol), and then raise the temperature to 160 °C and react for 12 hours. Evaporate the solvent under vacuum, pass through a silica gel column, using petroleum ether:dichloromethane = 10:1 as the eluent, to obtain the target compound A180 (purity by HPLC analysis: 99.23%), a yellow solid. MALDI-TOF-MS result: molecular ion peak: 1205.32; elemental analysis result: theoretical values: C, 84.64; H, 3.68; B, 0.90; N, 5.81; S, 2.66; Si, 2.33 (%) ; experimental values: C, 84.64; H, 3.68; B, 0.90; N, 5.81; S, 2.67; Si, 2.32 (%).

[0159] Example 16 Synthesis of Compound A190

[0160]

[0161] In a two-necked flask, under a nitrogen atmosphere, dissolve the polybromo precursor A190-1 (5 mmol) in 10 ml of dry tetrahydrofuran, cool to -78 °C, and add a pentane solution of n-butyllithium (1 M, 12 ml). React at this temperature for 1 hour. Dissolve reactants Q1 (6 mmol) and Q2 (6 mmol) in 40 ml of dry tetrahydrofuran pre-cooled to -78 °C, and then slowly inject this solution into the solution of A190-1 at -78 °C. Slowly warm to room temperature and react for 12 hours. After the reaction is completed, add a small amount of methanol to quench, evaporate the solvent under reduced pressure, add 100 ml of glacial acetic acid and 10 ml of concentrated hydrochloric acid, and then heat to reflux. After reacting for 2 hours, neutralize with a saturated aqueous sodium carbonate solution, extract and separate with dichloromethane, and collect the organic phase. Dry the organic phase with anhydrous sodium sulfate, then filter and concentrate the organic phase, and separate the compound through a silica gel column using petroleum ether:dichloromethane = 5:1 as the eluent to obtain compound A190-2.

[0162] In a sealed tube, dissolve compound A190-2 (1 mmol) in 20 mL of tert-butylbenzene. After cooling to -78 °C, add a pentane solution of tert-butyllithium (1 M, 2.5 mL). Then warm the mixture to 30 °C and react for 1 hour. Cool it to -78 °C again, slowly add boron tribromide (3 mmol), and then raise the temperature to 30 °C and continue stirring for 1 hour. After cooling to 0 °C, add diisopropylethylamine (5 mmol), and then raise the temperature to 160 °C and react for 12 hours. Evaporate the solvent under vacuum, pass through a silica gel column using petroleum ether:dichloromethane = 10:1 as the eluent to obtain the target compound A190 (purity 99.42% by HPLC analysis), a yellow solid. MALDI-TOF-MS result: molecular ion peak: 1162.55; elemental analysis result: theoretical values: C, 85.69; H, 6.15; B, 0.93; N, 4.82; Si, 2.41 (%); experimental values: C, 85.69; H, 6.15; B, 0.93; N, 4.81; Si, 2.42 (%).

[0163] Example 17 Synthesis of Compound A201

[0164]

[0165] In a two-necked flask under a nitrogen atmosphere, dissolve the polybromo precursor A201-1 (5 mmol) in 10 ml of dry tetrahydrofuran. Cool to -78 °C and add a pentane solution of n-butyllithium (1 M, 12 ml). React at this temperature for 1 hour. Dissolve reactants Q1 (6 mmol) and Q3 (6 mmol) in 40 ml of dry tetrahydrofuran pre-cooled to -78 °C, and then slowly inject this solution into the solution of A201-1 at -78 °C. Slowly warm to room temperature and react for 12 hours. After the reaction is completed, add a small amount of methanol to quench, evaporate the solvent under reduced pressure, add 100 ml of glacial acetic acid and 10 ml of concentrated hydrochloric acid, and then heat to reflux. After reacting for 2 hours, neutralize with a saturated aqueous solution of sodium carbonate, extract and separate with dichloromethane and collect the organic phase. Dry the organic phase with anhydrous sodium sulfate, then filter and concentrate the organic phase, and separate the compound through a silica gel column using petroleum ether:dichloromethane = 5:1 as the eluent to obtain compound A201-2.

[0166] In a sealed tube, compound A201-2 (1 mmol) was dissolved in 20 mL of tert-butylbenzene. After cooling to -78 °C, a pentane solution of tert-butyllithium (1 M, 2.5 mL) was added. Then the temperature was raised to 30 °C and the reaction was carried out for 1 hour. It was cooled to -78 °C again, and boron tribromide (3 mmol) was slowly added. Then it was raised to 30 °C and stirred for another 1 hour. After cooling to 0 °C, diisopropylethylamine (5 mmol) was added. Then the temperature was raised to 160 °C and the reaction was carried out for 12 hours. The solvent was evaporated under vacuum, and the product was purified by silica gel column chromatography using petroleum ether:dichloromethane = 10:1 as the eluent to obtain the target compound A201 (purity by HPLC analysis: 99.41%), a yellow solid. MALDI-TOF-MS result: molecular ion peak: 1242.58; elemental analysis result: theoretical values: C, 88.87; H, 5.76; B, 0.87; N, 4.51 (%); experimental values: C, 88.86; H, 5.78; B, 0.86; N, 4.51 (%).

[0167] Example 18 Synthesis of Compound A206

[0168]

[0169] In a two-necked flask under a nitrogen atmosphere, polybromo precursor A206-1 (5 mmol) was dissolved in 10 mL of dry tetrahydrofuran. After cooling to -78 °C, a pentane solution of n-butyllithium (1 M, 12 mL) was added and the reaction was carried out at this temperature for 1 hour. Reactants Q2 (6 mmol) and Q4 (6 mmol) were dissolved in 40 mL of dry tetrahydrofuran pre-cooled to -78 °C, and then this solution was slowly injected into the solution of A206-1 at -78 °C. The temperature was slowly raised to room temperature and the reaction was carried out for 12 hours. After the reaction was completed, a small amount of methanol was added to quench the reaction. The solvent was evaporated under reduced pressure. 100 mL of glacial acetic acid and 10 mL of concentrated hydrochloric acid were added, and then the temperature was raised to reflux. After reacting for 2 hours, it was neutralized with saturated aqueous sodium carbonate solution, extracted with dichloromethane, and the organic phase was collected. The organic phase was dried over anhydrous sodium sulfate, then filtered and concentrated. The compound was separated by silica gel column chromatography using petroleum ether:dichloromethane = 5:1 as the eluent to obtain compound A206-2.

[0170] In a sealed tube, dissolve compound A206-2 (1 mmol) in 20 mL of tert-butylbenzene. After cooling to -78 °C, add a pentane solution of tert-butyllithium (1 M, 2.5 mL). Then warm the mixture to 30 °C and react for 1 hour. Cool it to -78 °C again, slowly add boron tribromide (3 mmol), and then raise the temperature to 30 °C and continue stirring for 1 hour. After cooling to 0 °C, add diisopropylethylamine (5 mmol), and then raise the temperature to 160 °C and react for 12 hours. Evaporate the solvent under vacuum, pass through a silica gel column, using petroleum ether:dichloromethane = 15:1 as the eluent, to obtain the target compound A206 (purity by HPLC analysis: 99.58%), a yellow solid. MALDI-TOF-MS result: molecular ion peak: 1216.39; elemental analysis result: theoretical values: C, 85.84; H, 4.06; B, 0.89; N, 6.90; Si, 2.31 (%) ; experimental values: C, 85.84; H, 4.05; B, 0.89; N, 6.91; Si, 2.31 (%).

[0171] Example 19 Synthesis of Compound A223

[0172]

[0173] In a two-necked flask, under a nitrogen atmosphere, dissolve the polybromo precursor A223-1 (5 mmol) in 10 ml of dry tetrahydrofuran. Cool to -78 °C and add a pentane solution of n-butyllithium (1 M, 12 ml). React at this temperature for 1 hour. Dissolve reactants Q2 (6 mmol) and Q5 (6 mmol) in 40 ml of dry tetrahydrofuran pre-cooled to -78 °C, and then slowly inject this solution into the solution of A223-1 at -78 °C. Slowly warm to room temperature and react for 12 hours. After the reaction is completed, add a small amount of methanol to quench, evaporate the solvent under reduced pressure, add 100 ml of glacial acetic acid and 10 ml of concentrated hydrochloric acid, and then heat to reflux. After reacting for 2 hours, neutralize with saturated aqueous sodium carbonate solution, extract and separate with dichloromethane and collect the organic phase. Dry the organic phase with anhydrous sodium sulfate, then filter and concentrate the organic phase, and separate the compound by passing through a silica gel column with petroleum ether:dichloromethane = 5:1 as the eluent to obtain compound A223-2.

[0174] In a sealed tube, dissolve compound A223-2 (1 mmol) in 20 mL of tert-butylbenzene. After cooling to -78 °C, add a pentane solution of tert-butyllithium (1 M, 2.5 mL). Then, warm the mixture to 30 °C and react for 1 hour. Cool it to -78 °C again, slowly add boron tribromide (3 mmol), and then raise the temperature to 30 °C and continue stirring for 1 hour. After cooling to 0 °C, add diisopropylethylamine (5 mmol), and then raise the temperature to 160 °C and react for 12 hours. Evaporate the solvent under vacuum, and pass through a silica gel column with petroleum ether:dichloromethane = 10:1 as the eluent to obtain the target compound A223 (purity 99.25% by HPLC analysis), a yellow solid. MALDI-TOF-MS result: molecular ion peak: 1273.38; elemental analysis result: theoretical values: C, 87.66; H, 3.80; B, 0.85; N, 5.50; Si, 2.20 (%) ; experimental values: C, 87.65; H, 3.80; B, 0.85; N, 5.50; Si, 2.21 (%).

[0175] Example 20 Synthesis of Compound A227

[0176]

[0177] In a two-necked flask under a nitrogen atmosphere, dissolve the polybromo precursor A227-1 (5 mmol) in 10 ml of dry tetrahydrofuran. Cool to -78 °C and add a pentane solution of n-butyllithium (1 M, 12 ml). React at this temperature for 1 hour. Dissolve reactant Q6 (12 mmol) in 40 ml of dry tetrahydrofuran pre-cooled to -78 °C, and then slowly inject this solution into the solution of A227-1 at -78 °C. Slowly warm to room temperature and react for 12 hours. After the reaction is completed, add a small amount of methanol to quench, evaporate the solvent under reduced pressure, and pass through a silica gel column with petroleum ether:dichloromethane = 5:1 as the eluent to obtain compound A227-2.

[0178] In a sealed tube, dissolve compound A227-2 (1 mmol) in 20 mL of tert-butylbenzene. After cooling to -78 °C, add a pentane solution of tert-butyllithium (1 M, 2.5 mL). Then warm the mixture to 30 °C and react for 1 hour. Cool it to -78 °C again, slowly add boron tribromide (3 mmol), and then raise the temperature to 30 °C and continue stirring for 1 hour. After cooling to 0 °C, add diisopropylethylamine (5 mmol), and then raise the temperature to 160 °C and react for 12 hours. Evaporate the solvent under vacuum, pass through a silica gel column using petroleum ether:dichloromethane = 10:1 as the eluent to obtain the target compound A227 (purity 99.17% by HPLC analysis), a yellow solid. MALDI-TOF-MS result: molecular ion peak: 1527.35; elemental analysis result: theoretical values: C, 83.28; H, 3.56; B, 0.71; N, 4.58; S, 4.19; Si, 3.67 (%); experimental values: C, 83.28; H, 3.56; B, 0.71; N, 4.58; S, 4.18; Si, 3.68 (%).

[0179] Example 21 Synthesis of Compound A231

[0180]

[0181] In a two-necked flask under a nitrogen atmosphere, dissolve the polybromo precursor A231-1 (5 mmol) in 10 ml of dry tetrahydrofuran. Cool to -78 °C and add a pentane solution of n-butyllithium (1 M, 12 ml). React at this temperature for 1 hour. Dissolve the reactant Q7 (12 mmol) in 40 ml of dry tetrahydrofuran that has been pre-cooled to -78 °C, and then slowly inject this solution into the solution of A231-1 at -78 °C. Slowly warm to room temperature and react for 12 hours. After the reaction is completed, add a small amount of methanol to quench, evaporate the solvent under reduced pressure, add 100 ml of glacial acetic acid and 10 ml of concentrated hydrochloric acid, and then heat to reflux. After reacting for 2 hours, neutralize with saturated aqueous sodium carbonate solution, extract with dichloromethane and separate the liquid layers, collect the organic phase, dry the organic phase over anhydrous sodium sulfate, then filter and concentrate the organic phase, and separate the compound through a silica gel column using petroleum ether:dichloromethane = 5:1 as the eluent to obtain compound A231-2.

[0182] Dissolve compound A231-2 (1 mmol) in 20 mL of tert-butylbenzene in a sealed tube. After cooling to -78 °C, add a pentane solution of tert-butyllithium (1 M, 2.5 mL). Then, warm up to 30 °C and react for 1 hour. Cool down to -78 °C again, slowly add boron tribromide (3 mmol), and then raise the temperature to 30 °C and continue stirring for 1 hour. After cooling to 0 °C, add diisopropylethylamine (5 mmol), and then raise the temperature to 160 °C and react for 12 hours. Evaporate the solvent under vacuum, and pass through a silica gel column with petroleum ether:dichloromethane = 15:1 as the eluent to obtain compound A231-3.

[0183] Under an oxygen atmosphere, dissolve compound A231-3 (1 mmol) in a solution of DMSO (100 mL). Slowly add 2,3-dichloro-5,6-dicyanobenzoquinone (36 mmol) to the reaction flask at room temperature. Finally, react the mixture at room temperature for 72 h. Carefully quench the reaction mixture with H2O and MeOH, and then adjust the pH of the solution to 7.0 with phosphate buffer. Extract with DCM three times, concentrate the organic layer under reduced pressure, and purify the crude product by silica gel chromatography column (eluent: petroleum ether:dichloromethane = 15:1) to obtain the target product A-231 (32% yield, HPLC purity 99.31%), which is a yellow solid. MALDI-TOF-MS result, molecular ion peak: 1158.24; elemental analysis result, theoretical values: C, 81.86; H, 3.04; B, 0.93; N, 7.25; O, 1.38; S, 5.53, experimental values: C, 81.86; H, 3.05; B, 0.93; N, 7.26; O, 1.38; S, 5.51.

[0184] Device Example

[0185] The technical effects and advantages of the present invention are demonstrated and verified by specifically applying the compounds of the present invention to organic electroluminescent devices to test their actual performance in use.

[0186] The organic electroluminescent device includes a first electrode, a second electrode, and an organic material layer located between the two electrodes. The organic material can be further divided into multiple regions. For example, the organic material layer can include a hole transport region, a light-emitting layer, and an electron transport region.

[0187] The anode material can be an oxide transparent conductive material such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), zinc oxide (ZnO), etc. and any combination thereof. The cathode material can be a metal or alloy such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), etc. and any combination thereof.

[0188] 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 multi-layer structure including at least one layer of a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL).

[0189] The material of the hole transport region can be selected from but not limited to phthalocyanine derivatives such as CuPc, conductive polymers, or polymers containing conductive dopants such as poly(phenylene vinylene), 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.

[0190] The light-emitting layer includes a light-emitting dye (i.e., dopant) that can emit spectra of different wavelengths, and can also include a host material at the same time. The light-emitting layer can be a single-color light-emitting layer that emits a single color such as red, green, or blue. Multiple single-color light-emitting layers of different colors can be arranged in a planar pattern according to a pixel pattern, or stacked together to form a color light-emitting layer. When light-emitting layers of different colors are stacked together, they can be separated from each other or connected to each other. The light-emitting layer can also be a single color light-emitting layer that can simultaneously emit different colors such as red, green, and blue.

[0191] 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 multi-layer structure including at least one layer of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0192] Specifically, the method for preparing the organic electroluminescent device of the present invention includes the following steps:

[0193] 1. Ultrasonically treat the glass plate coated with the anode material in a commercial cleaning agent, rinse it in deionized water, ultrasonically degrease it in an acetone:ethanol mixed solvent, bake it in a clean environment until all moisture is completely removed, clean it with ultraviolet light and ozone, and bombard the surface with a low-energy cation beam;

[0194] 2. Place the glass plate with the anode in a vacuum chamber, evacuate to 1×10-5 to 9×10-3 Pa, and vacuum deposit a hole injection material on the anode layer film to form a hole injection layer at a deposition rate of 0.1 - 0.5 nm / s;

[0195] 3. A hole transport layer is formed by vacuum evaporation of a hole transport material on the hole injection layer, and the evaporation rate is 0.1 - 0.5 nm / s.

[0196] 4. An electron blocking layer is vacuum-evaporated on the hole transport layer, and the evaporation rate is 0.1 - 0.5 nm / s.

[0197] 5. An organic light-emitting layer of the device is vacuum-evaporated on the electron blocking layer. The organic light-emitting layer material includes a host material and a luminescent 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 so that the dye reaches a preset doping ratio.

[0198] 6. A hole blocking layer is vacuum-evaporated on the organic light-emitting layer, and its evaporation rate is 0.1 - 0.5 nm / s.

[0199] 7. An electron transport layer of the device is formed by vacuum evaporation of an electron transport material on the hole blocking layer, and its evaporation rate is 0.1 - 0.5 nm / s.

[0200] 8. LiF is vacuum-evaporated as an electron injection layer on the electron transport layer at a rate of 0.1 - 0.5 nm / s, and an Al layer is vacuum-evaporated as the cathode of the device at a rate of 0.1 - 0.5 nm / s.

[0201] An embodiment of the present invention also provides a display device, and the display device includes the organic electroluminescent device provided as above. The display device may specifically be a display device such as an OLED display, as well as any product or component with a display function including the display device, such as a TV, a digital camera, a mobile phone, a tablet computer, etc. The display device has the same advantages as the above organic electroluminescent device compared with the prior art, and will not be elaborated here.

[0202] The organic electroluminescent device of the present invention is further introduced through specific embodiments below.

[0203] Examples 1 - 40 of the present invention are organic electroluminescent devices prepared using the compounds of the present invention, and Comparative Examples 1 - 8 are parallel comparison devices prepared using prior art compounds P1, P2, P3, and P4 according to the same preparation method as the compounds of the present invention. The structural schemes of all the prepared devices are shown in Table 1 below:

[0204] Table 1:

[0205]

[0206]

[0207]

[0208]

[0209] Among them, the anode material is ITO; the hole injection layer material is HI, with a general total thickness of 5 - 30 nm, and 5 nm in this embodiment; the hole transport layer material is HT, with a general total thickness of 5 - 500 nm, and 30 nm in this embodiment; the host material of the Host organic light-emitting layer has a wide bandgap, TD is a TADF-type host, and the thickness of the organic light-emitting layer is generally 1 - 200 nm, and 24 nm in this embodiment; the electron transport layer material is ET, with a thickness of generally 5 - 300 nm, and 30 nm in this embodiment; the electron injection layer and cathode materials are selected as LiF (0.5 nm) and metallic aluminum (150 nm).

[0210] The structural formulas of various organic materials used in the above embodiments are as follows:

[0211]

[0212]

[0213] The device performances prepared in Examples 1 - 40 and Comparative Examples 1 - 8 of the present invention are shown in Table 2 below:

[0214] Table 2:

[0215]

[0216]

[0217] Compared with Comparative Examples 1 and 2, the efficiencies of Examples 1 - 42 have been significantly improved, and the full width at half maximum has also been narrowed. This is because in this type of compound of the present invention, a carbon atom or a silicon atom is introduced on both sides of the classical boron-nitrogen mother nucleus to form a spirofluorene or silaspirofluorene-like structure, connecting the two benzene rings on both sides, eliminating the repulsion between the original hydrogen atoms, significantly enhancing the rigidity of the molecule, and further reducing the full width at half maximum FWHM (≤25 nm), improving the color purity, and correspondingly significantly improving the efficiency of the light-emitting device, providing guidance for constructing a new type of narrow-spectrum light-emitting material.

[0218] Compared with Comparative Examples 3 - 8, the efficiencies of Examples 1 - 42 have been improved to a certain extent, and the device lifetime has been significantly enhanced. This is mainly due to the fact that on the basis of traditional spirofluorene or silaspirofluorene, the originally used fluorene and silafuorene structures are replaced with carbazole and substituted carbazole structures, where the para position of the spiro carbon atom or silicon atom is the N atom of carbazole. The advantage is that carbazole has strong electron-donating properties. By introducing two such carbazole locking units, the HOMO and LUMO energy levels of the molecule can be significantly increased, thereby effectively suppressing the injection and recombination of electrons on it, thus improving the light-emitting efficiency of the device and enhancing the stability of the device.

[0219] Meanwhile, due to the spatial structure of the tetrahedral spiro atom, the introduction of the spiro atom forms two orthogonal planes at the spiro atom, significantly increasing the intermolecular distance, thereby reducing the intermolecular interaction force and inhibiting molecular packing. In the device, it can reduce the interaction between the host and the dye and between dyes, improving the performance of the device such as luminous efficiency and lifespan. Further, by designing the variation of the peripheral substituents, the general formula compound of the present invention can perform photochromic regulation in the range from blue light to red light, while maintaining the characteristic of a relatively narrow full width at half maximum of luminescence, and the lifespan of the device has been greatly improved.

[0220] The electroluminescence spectrum of the OLED device prepared with the compound of the present invention has a narrow full width at half maximum (≤25 nm), showing obvious multiple resonance thermally activated delayed fluorescence characteristics, thus greatly enriching the framework system of multiple resonance narrow spectrum materials. At the same time, it greatly simplifies the synthesis process and improves the reaction yield; the corresponding electroluminescent device has a low turn-on voltage, high luminous efficiency, and an extremely long service life, and can meet the requirements of current panel manufacturing enterprises for high-performance materials, showing good application prospects in industrialization.

[0221] The above experimental data show that after the novel MR-TADF material prepared by the present invention is applied in the organic electroluminescent device, while achieving good performance of high color purity and high luminous efficiency of the device, it also realizes the low efficiency roll-off of the electroluminescent device and has an extremely long device lifespan. Therefore, this type of novel compound of the present invention is an organic light-emitting functional material with good performance and is expected to be promoted for commercial applications.

[0222] Although the present invention has been described in conjunction with the embodiments, the present invention is not limited to the above embodiments. It should be understood that under the guidance of the inventive concept of the present invention, those skilled in the art can make various modifications and improvements, and the appended claims define the scope of the present invention.

[0223] Obviously, the above embodiments are merely examples given for clear illustration and are not limitations on the implementation manners. For those of ordinary skill in the art, other different forms of changes or modifications can be made based on the above description. It is not necessary and impossible to enumerate all the implementation manners here. And the obvious changes or modifications derived therefrom are still within the protection scope of the present invention.

Claims

1. An organic compound having the structure shown in the following formula (1): In formula (1), ring A, ring B, ring C, ring D, ring E, ring F, ring G, ring H, ring I, ring J, and ring K each independently represent one of an aromatic ring having 5 to 20 carbon atoms or a heteroaromatic ring having 4 to 20 carbon atoms; W1, W2, and W3 each independently selected from a single bond, O, CO, SO2, S, NR1, CR2R3, or SiR4R5; m1, m2, and m3 are each independently 0 or 1; The R1, R2, R3, R4, and R5 are not connected to the adjacent groups or are connected to form a ring; R2 and R3 are not connected or are connected to form a ring; R4 and R5 are not connected or are connected to form a ring; The X and Y are each independently selected from C or Si; The R1, R2, R3, R4, and R5 are each independently selected from one of the following unsubstituted or R'-substituted groups: a C1-C36 linear alkyl group, a C3-C36 cycloalkyl group, a C6-C30 arylamino group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C5-C60 heteroaryl group; Said R a 、R b 、R c 、R d 、R e 、R f 、R g 、R h 、R i 、R j 、R k each independently represents a single substituent to the maximum allowable number of substituent groups; Said R a 、R b 、R c 、R d 、R e 、R f 、R g 、R h 、R i 、R j 、R k are each independently connected to the connected ring structure by a single bond or a fused bond; The said R a 、R b 、R c 、R d 、R e 、R f 、R g 、R h 、R i 、R j 、R k are not connected or connected into a ring between two adjacent ones among them; R a 、R b 、R c 、R d 、R e 、R f 、R g 、R h 、R i 、R j 、R k each independently selected from hydrogen, deuterium, halogen, carbonyl, carboxyl, nitro, cyano, amino or one of the following groups which are unsubstituted or substituted by R': a linear alkyl of C1-C36, a cycloalkyl of C3-C36, an alkoxy of C1-C10, a thioalkoxy of C1-C10, an alkylsilyl of C1-C10, an alkylamino of C1-C10, an arylamino of C6-C30, a heteroarylamino of C3-C30, an aryl of C6-C60, an aryloxy of C6-C60, a heteroaryl of C5-C60; Two adjacent R's are not connected or are connected to form a ring; R' is selected from one or a combination of two of deuterium, halogen, cyano, amino, a C2-C10 alkenyl group, a C1-C10 linear alkyl group, a C3-C10 cycloalkyl group, a C1-C10 alkoxy group, a C1-C10 thioalkoxy group, a C1-C10 alkylsilyl group, a C1-C10 alkylamino group, a C6-C60 arylamino group, a C3-C60 heteroarylamino group, a C6-C30 aryloxy group, a C6-C60 aryl group, a C3-C60 heteroaryl group; 2. The organic compound according to claim 1, characterized in that, In formula (1), the ring A, ring B, ring C, ring D, ring E, ring F, ring G, ring H, ring I, ring J, and ring K each independently have the structure shown in formula (a) or formula (b), and the dotted double bond represents the fusion position of the following groups in formula (1): In formula (a), Z 1 , Z 2 , Z 3 , Z 4 are each independently selected from CR 1 or N, and two adjacent R 1 are not connected or are connected by a chemical bond to form a ring; R 1 each independently selected from hydrogen, deuterium, cyano, halogen, amino, unsubstituted or R”-substituted C1-C20 linear alkyl, unsubstituted or R”-substituted C3-C20 cycloalkyl, unsubstituted or R”-substituted C1-C20 alkoxy, unsubstituted or R”-substituted C1-C20 alkylsilyl, unsubstituted or R”-substituted C1-C20 alkylamino, unsubstituted or R”-substituted C6-C30 arylamino, unsubstituted or R”-substituted C3-C30 heteroarylamino, unsubstituted or R”-substituted C6-C30 aryloxy, unsubstituted or R”-substituted C3-C30 heteroaryloxy, unsubstituted or R”-substituted C6-C60 aryl, unsubstituted or R”-substituted C3-C60 heteroaryl; In formula (b), Z is selected from O, S, NR 2 or CR 3 R 4 ; R 2 、R 3 、R 4 is not connected to the adjacent group or forms a ring through a chemical bond; R 3 and R 4 are not connected or form a ring; R 2 、R 3 、R 4 Each independently selected from an unsubstituted or R”-substituted C1-C20 linear alkyl group, an unsubstituted or R”-substituted C3-C20 cycloalkyl group, an unsubstituted or R”-substituted C6-C60 aryl group, and an unsubstituted or R”-substituted C3-C60 heteroaryl group; R” is selected from one or a combination of two of deuterium, halogen, cyano, amino, a C2-C20 alkenyl group, a C1-C20 linear alkyl group, a C3-C20 cycloalkyl group, a C1-C20 alkoxy group, a C1-C20 thioalkoxy group, a C1-C20 alkylsilyl group, a C1-C20 alkylamino group, a C6-C60 arylamino group, a C3-C60 heteroarylamino group, a C6-C30 aryloxy group, a C6-C60 aryl group, a C3-C60 heteroaryl group; Preferably, Z is selected from O, S or NR 2 .

3. The organic compound according to claim 2, characterized in that, One of the ring A, ring B, ring C, ring D, ring E, ring F, ring G, ring H, ring I, ring J, and ring K has the structure shown in formula (b), and the other ring structures each independently have the structure shown in formula (a) or formula (b); Preferably, in formula (a) and formula (b), the R 1 , R 2 , R 3 , R 4 are each independently selected from hydrogen, deuterium, cyano, halogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, 2-methylbutyl, trifluoromethyl, pentafluoroethyl, phenyl, naphthyl, anthryl, benzanthryl, phenanthryl, benzophenanthryl, pyrenyl, tetraphenyl, pentaphenyl, benzopyrenyl, biphenyl, terphenyl, quaterphenyl, fluorene, spirobifluorene, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, furyl, benzofuryl, isobenzofuryl, dibenzofuryl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indolocarbazolyl, pyridyl, quinolinyl, isoquinolinyl, acridinyl, phenanthridinyl, benzo-5,6-quinolyl, benzo-6,7-quinolyl, benzo-7,8-quinolyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthimidazolyl, phenanthrimidazolyl, pyridinimidazolyl, pyrazinimidazolyl, quinoxalinimidazolyl, oxazolyl, benzoxazolyl, naphthoxazolyl, anthroxazolyl, phenanthroxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazaanthracenyl, 2,7-diazapyrenyl, 2,3-diazapyrenyl, 1,6-diazapyrenyl, 1,8-diazapyrenyl, 4,5-diazapyrenyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarbazolyl, phenanthrolinyl, 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-tetrazinyl, indazyl, benzothiadiazolyl, 9,9-dimethylacridinyl, triarylamine, adamantane, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl or methoxy.

4. The organic compound according to claim 1, wherein In formula (1), the ring A, ring B, ring C, ring D, ring E, ring F, ring G, ring H, ring I, ring J, and ring K each independently represent one of an aromatic ring having 5 to 12 carbon atoms or a heteroaromatic ring having 4 to 10 carbon atoms; Preferably, the ring A, ring B, ring C, ring D, ring E, ring F, ring G, ring H, ring I, ring J, and ring K each independently represent an aromatic ring having 6 to 12 carbon atoms; More preferably, each of ring A, ring B, ring C, ring D, ring E, ring F, ring G, ring H, ring I, ring J, and ring K is independently selected from any one of a benzene ring, a naphthalene ring, or a fluorene ring; Even more preferably, each of ring A, ring B, ring C, ring D, ring E, ring F, ring G, ring H, ring I, ring J, and ring K is independently selected from a benzene ring.

5. The organic compound according to any one of claims 1-4, characterized in that, In formula (1), m3 is 0, and m1 and m2 are each independently 0 or 1; W1 and W2 are each independently selected from a single bond, O, CO, SO2, S, NR1, CR2R3, or SiR4R5; Preferably, m3 is 0, and m1 and m2 are each independently 0 or 1; W1 and W2 are each independently selected from a single bond, CO, NR1, or CR2R3; Even more preferably, m3 is 0, and m1 and m2 are each independently 0 or 1; both W1 and W2 are selected from a single bond.

6. The organic compound according to claim 1, wherein It has the structure shown in the following formula (2): Among them, R a 、R b 、R c 、R d 、R e 、R f 、R g 、R h 、R i 、R j 、R k 、X, Y, W1, W2, m1, and m2 are defined in the same way as in formula (1); Further preferably, m1 and m2 are each 1, W1 and W2 each independently represent a single bond, CO, NR1, or CR2R3, and there is no connection or a single-bond connection between R1, R2, R3 and the adjacent ring; there is no connection or a ring is formed between R2 and R3; Alternatively preferably, one of m1 and m2 is 0 and the other is 1, W1 and W2 represent a single bond, CO, NR1, or CR2R3, and there is no connection or a single-bond connection between R1, R2, R3 and the adjacent ring; there is no connection or a ring is formed between R2 and R3; Even more preferably, m1 and m2 are each 1, and both W1 and W2 represent a single bond.

7. The organic compound according to claim 6, characterized in that, It has the structures shown in the following formulas (2-1), (2-2), and (s2-3): Among them, R a , R b , R c , R d , R e , R f , R g , R h , R i , R j , R k are all defined in the same way as those in formula (1); Preferably, it has the structure shown in formula (2-1).

8. The organic compound according to any one of claims 1, 6 or 7, characterized in that, The said R a , R b , R c , R d , R e , R f , R g , R h , R i , R j , R k are each independently selected from hydrogen, deuterium, a halogen, a cyano group, or one of the following groups which are unsubstituted or substituted by R': a C1-C6 linear alkyl group, a C3-C6 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 thioalkoxy group, a C6-C20 arylamino group, a C3-C20 heteroarylamino group, a C6-C30 aryl group, a C6-C30 aryloxy group, a C5-C30 heteroaryl group; R' is selected from one of deuterium, a halogen, a cyano group, an amino group, a C1-C6 linear alkyl group, a C3-C6 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 thioalkoxy group, a C1-C6 alkylsilyl group, a C1-C6 alkylamino group, a C6-C30 arylamino group, a C3-C30 heteroarylamino group, a C6-C30 aryloxy group, a C6-C30 aryl group, or a C3-C30 heteroaryl group; Preferably, the R a and R b and R c and R d and R e and R f and R g and R h and R i and R j and R k independently selected from hydrogen, deuterium, cyano group, halogen, or a combination of one or two of the following substituted groups: 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, anthryl, benzanthryl, phenanthryl, benzophenanthryl, pyrenyl, chrysenyl, perylenyl, fluoranthenyl, tetraphenyl, pentaphenyl, benzopyrenyl, biphenyl, azobenzene, terphenyl, triphenyl, tetraphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis- or trans-indeno[1,2-b]fluorene, trimeric indene, isomeric trimeric indene, spirotrimeric indene, spiroisomeric trimeric indene, furyl, benzofuryl, isobenzofuryl, dibenzofuryl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indolocarbazolyl, pyridyl, quinolinyl, isoquinolinyl, acridinyl, phenanthridinyl, benzo[5,6]quinolinyl, benzo[6,7]quinolinyl, benzo[7,8]quinolinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthimidazolyl, phenanthrimidazolyl, pyridinimidazolyl, pyrazinimidazolyl, quinoxalinimidazolyl, oxazolyl, benzoxazolyl, naphthoxazolyl, anthroxazolyl, phenanthroxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazaphenanthrenyl, 2,7-diazapyrenyl, 2,3-diazapyrenyl, 1,6-diazapyrenyl, 1,8-diazapyrenyl, 4,5-diazapyrenyl, 4,5,9,10-tetraazaperylenyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarbazolyl, phenanthrolinyl, 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-tetrazinyl, 1,2,3,4-tetrazinyl, 1,2,3,5-tetrazinyl, purinyl, pteridinyl, indolizinyl, benzothiadiazolyl, 9,9-dimethylacridinyl, triarylamine, adamantane, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl or methoxy; More preferably, the R a , R b , R c , R d , R e , R f , R g , R h , R i , R j , R k are each independently selected from hydrogen, deuterium, cyano, halogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, 2-methylbutyl, trifluoromethyl, pentafluoroethyl, phenyl, naphthyl, anthracenyl, benzanthracenyl, phenanthryl, benzophenanthryl, pyrenyl, tetraphenyl, pentaphenyl, benzopyrenyl, biphenyl, azobenzene, terphenyl, triphenyl, tetraphenyl, fluorene, spirobifluorene, furyl, benzofuryl, isobenzofuryl, dibenzofuryl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indolocarbazolyl, pyridyl, quinolinyl, isoquinolinyl, pyrazolyl, indazolyl, imidazolyl, pyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarbazolyl, phenanthrolinyl, 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-tetrazinyl, indolizinyl, benzothiadiazolyl, 9,9-dimethylacridinyl, triarylamine, adamantane, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl or methoxy.

9. The organic compound according to claim 1 or 6, characterized in that, R1, R2, R3, R4, and R5 are each independently selected from hydrogen, deuterium, cyano, halogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, 2-methylbutyl, trifluoromethyl, pentafluoroethyl, phenyl, naphthyl, anthracenyl, benzanthracenyl, phenanthryl, benzophenanthryl, pyrenyl, tetracenyl, pentacenyl, benzopyrenyl, biphenyl, terphenyl, quaterphenyl, fluorene, spirobifluorene, furyl, benzofuryl, isobenzofuryl, dibenzofuryl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indolocarbazolyl, pyridyl, quinolinyl, isoquinolinyl, pyrazolyl, indazolyl, imidazolyl, pyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarbazolyl, phenanthrolinyl, 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-tetrazinyl, indolizinyl, benzothiadiazolyl, 9,9-dimethylacridinyl, triarylamine, adamantane, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl, or methoxy.

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

11. Use 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 light-emitting device, an optical sensor, a solar cell, an organic thin-film transistor, or an organic field-effect transistor; Further, the use of the compound is as a light-emitting layer material in an organic light-emitting device, specifically as a light-emitting material in the light-emitting layer.

12. An organic light-emitting device, comprising a substrate, and an anode layer, a plurality of light-emitting functional layers, and a cathode layer formed in sequence 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, 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 between the hole transport layer and the electron transport layer, wherein the light-emitting layer contains the compound according to any one of claims 1-10; Furthermore, the light-emitting functional layer includes a hole transport region, a light-emitting layer, and an electron transport region. The hole transport region is formed on the first electrode, the second electrode is formed on the electron transport region, and the light-emitting layer is located between the hole transport region and the electron transport region; wherein, The light-emitting layer contains the compound according to any one of claims 1-10.

13. A display device, comprising the organic light-emitting device according to claim 12.

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