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 disclosed by the invention has a structure as shown in a formula (1), wherein ring A, ring B, ring C and ring I respectively and independently represent a benzene ring, a naphthalene ring or an anthracene ring; a ring D, a ring E, a ring F and a ring G independently represent one of C5-C20 aromatic rings and C4-C20 heteroaromatic rings respectively; a ring Z and a ring W independently represent one of a C5-C20 aromatic ring and a C4-C20 nitrogen-containing heteroaromatic ring respectively; x and Y are respectively and independently selected from a single bond, O, CO, SO2, S, NR1, CR2R3 or SiR4R5; and when X is a single bond, Y is selected from CO, SO2, S, NR1, CR2R3 or SiR4R5. According to the organic electroluminescent device adopting the compound disclosed by the invention, the emission half-peak width is remarkably reduced, and ultra-narrow-band pure red light emission is realized. # imgabs0 #

Description

Technical Field

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

[0002] An organic light emitting diode (OLED) is a device that emits light by current driving. Its main characteristics come from the organic light emitting layer therein. When an appropriate voltage is applied to the positive and negative electrodes of the OLED, holes generated by the anode and electrons generated by the cathode combine in the light emitting layer, and three colors of red, green, and blue are generated according to the characteristics of the material.

[0003] OLEDs have the advantages of self-luminescence, high brightness, wide viewing angle, high contrast, low power consumption, thin light emitting layer, and flexibility. In recent years, they have developed rapidly and are currently widely used in display fields such as lighting, smartphones, tablet computers, TVs, VR, and wearable devices, and have attracted much attention in the fields of new display technologies and new lighting technologies and received strong support from the country.

[0004] To prepare a light emitting device with high luminous efficiency and long service life and improve the performance of the device, the core luminescent material is particularly crucial. A high-efficiency and long-life OLED device is usually the result of an optimized combination of the device structure and various organic materials. For traditional fluorescent materials, their internal quantum efficiency (IQE) is only 25%, and they can only utilize singlet excitons for luminescence. Phosphorescent materials usually enhance intersystem crossing by the strong spin-orbit coupling of noble metals (such as Ir, Pt), and at the same time utilize both singlet and triplet excitons for luminescence, making the internal quantum efficiency reach 100%. On this basis, the industry has been committed to developing a new generation of organic electroluminescent materials to further improve the performance of the device.

[0005] With the development of technology, in order to meet the BT.2020 standard promulgated 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 luminescent materials, in addition to high efficiency and long life, a narrower full width at half maximum is also required to achieve higher color purity. However, the full width at half maximum of currently commercialized 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.

[0006] In recent years, novel OLED materials based on multiple resonance (MR) have become a research hotspot in the field of organic electroluminescence due to their advantages of high efficiency and narrow spectra. However, there are still relatively few red MR-TADF materials. After the light color reaches red, the bandgap between molecular energy levels is small, resulting in enhanced non-radiative transitions and low device efficiency. Moreover, due to the structural relaxation between the ground state and the excited state, red light usually has a relatively large full width at half maximum. Developing red MR-TADF materials with high efficiency, long lifespan, and narrow spectra is the key to further improving the performance of OLEDs. Summary of the Invention

[0007] To solve the above technical problems, the present invention provides an organic compound with the property of narrow-spectrum pure red light emission. The specific technical solution is as follows:

[0008] An organic compound having a structure as shown in formula (1) below:

[0009]

[0010] In formula (1), ring A, ring B, ring C, and ring I each independently represent a benzene ring, a naphthalene ring, or an anthracene ring;

[0011] Ring D, ring E, ring F, and ring G each independently represent one of an aromatic ring with 5 to 20 carbon atoms or a heteroaromatic ring with 4 to 20 carbon atoms;

[0012] [[ID=ID=20]]Ring Z and ring W each independently represent one of an aromatic ring with 5 to 20 carbon atoms or a nitrogen-containing heteroaromatic ring with 4 to 20 carbon atoms;

[0013] X and Y each independently are selected from a single bond, O, CO, SO2, S, NR1, CR2R3, or SiR4R5;

[0014] 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;

[0015] R1, R2, R3, R4, and R5 each independently are selected from one of the following unsubstituted or R'-substituted groups: a linear alkyl group with 1 to 36 carbon atoms, a cycloalkyl group with 3 to 36 carbon atoms, an arylamino group with 6 to 30 carbon atoms, an aryl group with 6 to 60 carbon atoms, an aryloxy group with 6 to 60 carbon atoms, or a heteroaryl group with 5 to 60 carbon atoms;

[0016] m and n each independently are 0 or 1;

[0017] R a 、R b 、R c 、R d, R e , R f , R g , R i , R z , R w each independently represents a monosubstituent to the maximum allowable number of substituents;

[0018] R a , R b , R c , R d , R e , R f , R g , R i , R z , R w each independently is connected to the linked ring structure by a single bond or a fused bond;

[0019] The said R c and R d are not connected or are connected to form a ring; R e and R f are not connected or are connected to form a ring; R g and R i are not connected or are connected to form a ring; R z , R w are not connected or are connected to form a ring;

[0020] R a , R b , R c , R d , R e , R f , R g , R i , R z , R w each independently is selected from hydrogen, deuterium, halogen, carbonyl, carboxyl, nitro, cyano, amino or one of the following groups which are unsubstituted or substituted by R': C1-C36 linear alkyl, C3-C36 cycloalkyl, C1-C10 alkoxy, Cl-C10 thioalkoxy, C1-C10 alkylsilyl, C2-C10 alkenyl, C6-C30 arylsilyl, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C60 aryl, C6-C60 aryloxy, C5-C60 heteroaryl;

[0021] There is no connection or a ring is formed between two adjacent R'; R' is selected from any one or a combination of two of 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, and C3-C60 heteroaryl.

[0022] In the general formula (1) of the present invention, ring Z and ring W are in a fused connection relationship, and the fusion position is a boron atom and a nitrogen atom. Ring Z and ring W each independently may be selected from a C5-C20 aromatic ring or a C4-C20 nitrogen-containing heteroaromatic ring, meaning that other atoms in the ring structure of the aromatic ring or heteroaromatic ring may be selected from carbon atoms or nitrogen atoms. Specifically, for example, when both ring Z and ring W are benzene rings, it has the structure as shown in the following formula (a), and when ring Z and ring W are a pyridine ring and a naphthalene ring respectively, it has the structure as shown in the following formula (b) or (c):

[0023]

[0024] In the present invention, the "substituted or unsubstituted" group may be substituted with one substituent or 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 substituents is as shown above and will not be elaborated one by one.

[0025] In the present invention, the expression "connected by a single bond or fused connection" generally means that the substituent group is directly connected to the parent nucleus structure by a single bond, or the substituent group is fused to the parent nucleus structure to form a fused polycyclic 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.

[0026] In this specification, the expression 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.

[0027] 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 bonding can occur.

[0028] In this specification, "each independently" means that when its subject has multiple, they may be the same or different from each other.

[0029] In the present invention, for the description of chemical elements, unless otherwise specified, the concept of their isotopes is usually included. For example, the description of "hydrogen (H)" includes the concepts of its isotopes 1H (protium or H) and 2H (deuterium or D); carbon (C) includes 12C, 13C, etc., which will not be elaborated here.

[0030] The heteroatoms in the present invention usually refer to atoms or atomic groups selected from N, O, S, P, Si, and Se, preferably selected from N, O, and S.

[0031] In this specification, examples of halogens include: fluorine, chlorine, bromine, iodine, etc.

[0032] In the present invention, unless otherwise specified, both aryl and heteroaryl include monocyclic and fused-ring cases.

[0033] In the present invention, the C6-C60 can be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, C48, C50, C52, C54, C56, or C58, etc.

[0034] The C3-C60 can be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, C48, C50, C52, C54, C56, or C58, etc.

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

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

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

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

[0039] Any of C2-C10 may be C2, C3, C4, C5, C6, C7, C8, C9 or C10.

[0040] 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, group, tetracenyl 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 tetracenyl group is selected from 1-tetracenyl group, 2-tetracenyl group and 9-tetracenyl 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.

[0041] 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 aryl 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.

[0042] Specific examples of the arylene in the present invention can be exemplified by divalent groups obtained by removing one hydrogen atom from the above-mentioned examples of aryl groups. 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 exemplified by divalent groups obtained by removing one hydrogen atom from the above-mentioned examples of heteroaryl groups.

[0043] The aryloxy or heteroaryloxy in the present invention can be exemplified by monovalent groups composed of the above-mentioned aryl or heteroaryl and oxygen.

[0044] In the present invention, arylamino represents a group formed by substituting one or two hydrogens on the amino group with aryl groups, wherein the connection site of the arylamino can be connected to the aryl in the arylamino or to the N in the arylamino. The exemplary number of carbon atoms and specific groups of the aryl in the arylamino are the same as those described above.

[0045] Examples of the C6-C30 arylamino mentioned in the present invention include, for example, phenylamino, methylphenylamino, naphthylamino, anthrylamino, phenanthrylamino, biphenylamino, etc.

[0046] Examples of the C3-C30 heteroarylamino mentioned in the present invention include, for example, pyridylamino, pyrimidinylamino, dibenzofurylamino, etc.

[0047] 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.

[0048] 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.

[0049] 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.

[0050] 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.

[0051] 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.

[0052] It should be noted that in this 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 each group, rather than the effect of a single group.

[0053] Furthermore, the organic compound of the present invention has a structure shown in formula (2-1) or formula (2-2):

[0054]

[0055] Among them, ring D, ring E, ring F, ring G, R a 、R c 、R d 、R e 、R f 、R g 、R i 、R z 、R w 、m, n are defined in the same way as those in formula (1);

[0056] Ring Z and ring W each independently represent one of an aromatic ring having 6 to 12 carbon atoms and a nitrogen-containing heteroaromatic ring having 6 to 12 carbon atoms;

[0057] X is selected from a single bond, O, CO, SO2, S, NR1, CR2R3 or SiR4R5; Y is selected from a single bond, NR1 or CR2R3; and when X is a single bond, Y is selected from CO, SO2, S, NR1, CR2R3 or SiR4R5;

[0058] Preferably, when X is a single bond, Y is selected from NR1 or CR2R3;

[0059] More preferably, m is 0 or 1, X is selected from a single bond, NR1 or CR2R3; n is 1, Y is selected from a single bond;

[0060] Preferably, ring D, ring E, ring F, and ring G each independently represent one of an aromatic ring having 5 to 12 carbon atoms and a heteroaromatic ring having 4 to 10 carbon atoms; ring Z and ring W each independently represent a benzene ring, a naphthalene ring, an anthracene ring, a pyridine ring, a pyrazine ring or a pyridazine ring.

[0061] Further preferably, it is characterized in that in formula (1), formula (2-1), and formula (2-2), ring D, ring E, ring F, and ring G each independently have a structure shown in formula (a) or formula (b), and the dotted line represents the fusion position of the following groups in formula (1), formula (2), and formula (2-2):

[0062]

[0063] In formula (a), U 1 、U 2 、U 3 、U 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;

[0064] 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;

[0065] In formula (b), X 1 is selected from O, S, NR 2 or CR 3 R 4 ; R 2 、R 3 、R 4 are not connected to 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;

[0066] 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;

[0067] R” is selected from any one or a combination of two of 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.

[0068] Continuing preferably, in formula (a), U1 , U 2 , U 3 , U 4 are each independently selected from CR 1 , R 1 are each independently selected from hydrogen, deuterium, cyano, 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, fluorene, spirobifluorene, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis- or trans-indeno[1,2-b]fluorene, trindene, isotrindene, spirotrindene, spiroisotrindene, 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, 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, pyrrolidine, piperidine, methoxy or silyl;

[0069] In formula (b), R 2 , R 3 , R 4 are each independently selected from one or a combination of two of the following substituents: halogen, cyano, 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, biphenyl, azobenzene, terphenyl, triphenyl, tetraphenyl, fluorene, spirobifluorene, furyl, benzofuryl, dibenzofuryl, thienyl, benzothienyl, 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, oxazolyl, benzoxazolyl, naphthoxazolyl, anthroxazolyl, phenanthroxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, triazinyl, benzothiadiazolyl, 9,9-dimethylacridinyl, triarylamine, adamantane, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl, pyrrolidine, piperidine, methoxy.

[0070] In the general formula compound of the present invention, preferably, both ring Z and ring W are benzene rings; or one of ring Z and ring W is a naphthalene ring and the other is a benzene ring; or one of ring Z and ring W is a pyridine ring and the other is a benzene ring; or one of ring Z and ring W is a naphthalene ring and the other is a pyridine ring; or both ring Z and ring W are pyridine rings;

[0071] R[[ID=***13]] z , R w are not connected or are connected to form a ring;

[0072] Ring D, ring E, ring F, and ring G each independently represent an aromatic ring having 6 to 12 carbon atoms; preferably, ring D, ring E, ring F, and ring G each independently are selected from any one of a benzene ring, a naphthalene ring, or a fluorene ring;

[0073] The R z , R wEach independently selected from hydrogen, deuterium, halogen, cyano, amino 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, C1-C10 alkylsilyl, C2-C6 alkenyl, C6-C30 arylsilyl, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryl, C6-C30 aryloxy, C5-C30 heteroaryl;

[0074] R' is selected from any one of deuterium, halogen, cyano, amino, C2-C10 alkenyl, C1-C10 linear alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C6-C60 aryl, C3-C60 heteroaryl;

[0075] Preferably, the R z and R w each independently selected from hydrogen, deuterium or one or a combination of two of the following substituted groups: cyano, halogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, 2-methylbutyl, trifluoromethyl, pentafluoroethyl, vinyl, propenyl, phenyl, naphthyl, anthryl, biphenyl, terphenyl, fluorenyl, spirobifluorenyl, carbazolyl, pyridyl, quinolinyl, acridinyl, phenazinyl, phenothiazinyl, azacarbazolyl, phenanthrolinyl, 1,3,5-triazinyl, 9,9-dimethylacridinyl, triarylamine, adamantane, fluorophenyl, methylphenyl, trimethylphenyl, tert-butylphenyl, cyanophenyl, pyrrolidine, trimethylsilyl, triphenylsilyl, piperidine or methoxy.

[0076] In the general formula compound of the present invention, preferably, the R a and R b and R c and R d and R e and R f and R g and R i each independently selected from hydrogen, deuterium, halogen, cyano, amino 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-C2 O arylamino, C3-C20 heteroarylamino, C6-C30 aryl, C6-C30 aryloxy, C5-C30 heteroaryl;

[0077] R' is selected from any one of deuterium, halogen, cyano, amino, C2-C10 alkenyl, C1-C10 linear alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C6-C60 aryl, and C3-C60 heteroaryl;

[0078] Preferably, the said R a , R b , R c , R d , R e , R f , R g , R i are each independently selected from hydrogen, deuterium, or one or a combination of two of the following substituent groups: halogen, cyano, 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, biphenyl, terphenyl, triphenyl, tetraphenyl, fluorene, spirobifluorene, furyl, benzofuryl, dibenzofuryl, thienyl, benzothienyl, 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, oxazolyl, benzoxazolyl, naphthoxazolyl, anthroxazolyl, phenanthroxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, triazinyl, benzothiadiazolyl, 9,9-dimethylacridinyl, triarylamine, adamantane, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl, pyrrolidine, piperidine, methoxy;

[0079] R1, R2, R3, R4, and R5 are each independently selected from one or a combination of two of the following substituents: halogen, cyano, 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, tetracenyl, pentacenyl, biphenyl, terphenyl, quaterphenyl, fluorene, spirobifluorene, furyl, benzofuryl, dibenzofuryl, thienyl, benzothienyl, 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, oxazolyl, benzoxazolyl, naphthoxazolyl, anthroxazolyl, phenanthroxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, triazinyl, benzothiadiazolyl, 9,9-dimethylacridinyl, triarylamine, adamantane, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl, pyrrolidine, piperidine, methoxy.

[0080] Furthermore, the general formula compounds of the present invention can preferably select the following specific structural compounds A1 - A72, B1 - B92, C1 - C68, D1 - D64, E1 - E64, F1 - F64, which are only representative:

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097] The innovative point in the structural design of this type of compound of the present invention is as follows: The use of an indolocarbazole group fused with a naphthalene ring or anthracene ring doped with B-N atoms can not only expand the π-conjugation of the entire molecule, shifting the optical color to a pure red light emission with a standard of 620 - 630 nm. Moreover, due to the introduction of B-N atoms, without changing the optical color, the full width at half maximum (FWHM) of the emission is further reduced, achieving an ultra-narrowband pure red light emission. Since the introduced B and N atoms have different electronegativities, the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) are localized on the N and B atoms respectively, enhancing the multiple resonance (MR) effect, suppressing the non-bonding stretching vibration and the structural relaxation between the ground state and the excited state, thereby reducing the FWHM.

[0098] Meanwhile, a spiro atom is introduced on one side of the N-B-N core, connecting the two benzene rings on both sides, eliminating the repulsion between the original hydrogen atoms, significantly enhancing the molecular rigidity, significantly narrowing the FWHM (FWHM is 20 - 30 nm), and improving the luminescence efficiency (PLQY > 90%). Due to the tetrahedral spatial structure of the spiro atom, the introduction of the spiro atom forms two orthogonal planes at the spiro atom, significantly increasing the intermolecular distance and reducing the intermolecular interaction force, which can reduce the interaction between the host and the dye and between the dyes in the device, thereby significantly improving the luminescence efficiency and the lifetime of the device. Different spiro atom fragments have different triplet energy levels, which can regulate the distribution of triplet excitons in the molecule, thereby affecting the exciton lifetime and further regulating the lifetime of the device. And the introduction of the spiro atom fragment will not have a significant impact on the optical color, and can significantly improve the lifetime of the device without changing the optical color and FWHM. The fragment structure that can be connected at the spiro atom in the structure designed by the compound of the present invention can be preferably the following structure, where "*" represents the site connected to the spiro atom:

[0099]

[0100] The electroluminescence spectrum of the OLED device prepared with the compound of the present invention has a narrow full width at half maximum (<30 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, the synthesis process is greatly simplified and the reaction yield is improved. The corresponding electroluminescent device has a low starting voltage, high luminous efficiency and extremely long service life, which can meet the requirements of current panel manufacturing enterprises for high-performance materials and shows good application prospects in industrialization.

[0101] 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.

[0102] The 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, which includes a substrate, and an anode layer, multiple light-emitting functional layers and a cathode layer formed on the substrate in sequence; 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 located between the hole transport layer and the electron transport layer; wherein, preferably, the light-emitting layer contains a general formula compound shown in any one of the above general formula (1), formula (2-1), and formula (2-2), or the light-emitting layer contains at least one of the above specific compounds A1-A72, B1-B92, C1-C68, D1-D64, E1-E64, and F1-F64.

[0103] The fourth object of the present invention is to provide a display device that uses the above-mentioned organic electroluminescent device of the present invention. Specific Embodiments

[0104] The following will take multiple synthesis 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.

[0105] 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 Scientific Co., Ltd. and Xilong Chemical Co., Ltd. The mass spectrometer used to determine the following compounds is a ZAB-HS type mass spectrometer (manufactured by Micromass, UK).

[0106] The following is a brief description of the synthesis of the compounds of this invention. First, intermediate I is obtained through nucleophilic substitution and a Buchwald–Hartwig reaction. Subsequently, intermediate II undergoes lithium-halide exchange with n-butyl lithium, followed by nucleophilic addition with an aromatic ketone and subsequent acidification and ring closure. Finally, electrophilic borylation with boron tribromide under the action of tert-butyl lithium yields the target compound.

[0107] Synthesis Example 1 Synthesis of Compound A4

[0108]

[0109] In a two-necked flask, under a nitrogen atmosphere, 1-bromo-3-chloro-2-fluoro-4-iodobenzene (10 mmol), carbazole (10 mmol), and cesium carbonate (40 mmol) were dissolved in 150 mL of N,N-dimethylformamide (DMF). The temperature was raised to 150°C and the reaction was allowed to proceed for 12 hours. After the reaction was completed and cooled, the mixture was poured into cold water, filtered, washed twice with 100 mL of water, and then twice with 10 mL of methanol. The target compound A4-1 was obtained by drying.

[0110] In a two-necked flask under nitrogen atmosphere, compound A4-1 (10 mmol), intermediate I1 (10 mmol), trisdibenzylideneacetone dipalladium (1 mmol), tri-tert-butylphosphine tetrafluoroborate (2 mmol), and sodium tert-butoxide (12 mmol) were added sequentially. 100 ml of dry toluene was added and the temperature was raised to 110°C. The reaction was allowed to proceed for 12 hours. After cooling, the liquid was separated and the organic phase was collected. The organic phase was dried over anhydrous sodium sulfate, filtered, concentrated, and separated by silica gel column development with petroleum ether:dichloromethane = 10:1 to obtain compound A4-2.

[0111] In a two-necked flask, under a nitrogen atmosphere, compound A4-2 (5 mmol) was dissolved in 10 ml of dry tetrahydrofuran, cooled to -78°C, and a pentane solution of n-butyllithium (1 M, 6 ml) was added. The reaction was allowed to proceed at this temperature for 1 hour. 3,6-Dimethyl-9-fluorenone was dissolved in 40 ml of dry tetrahydrofuran, previously cooled to -78°C. This solution was then slowly injected into the A4-2 solution at -78°C. The mixture was slowly warmed to room temperature and allowed to react 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 100 ml of glacial acetic acid and 10 ml of concentrated hydrochloric acid were added. The mixture was then heated to reflux. After reacting for 2 hours, the mixture was neutralized with a saturated aqueous sodium carbonate solution, extracted with dichloromethane, and the organic phase was collected. The organic phase was dried over anhydrous sodium sulfate, filtered, concentrated, and separated by silica gel column chromatography using petroleum ether:dichloromethane = 5:1 as the developing solvent to obtain compound A4-3.

[0112] Dissolve compound A4-3 (1 mmol) in 20 mL of tert-butylbenzene in a sealed tube. Cool to -78°C, then add tert-butyllithium in pentane (1 M, 2.5 mL). The mixture is then heated to 30°C and allowed to react for 1 hour. Cool again to -78°C, slowly add boron tribromide (3 mmol), then heat to 30°C and continue stirring for 1 hour. Cool to 0°C, add diisopropylethylamine (5 mmol), then heat to 160°C and react for 12 hours. Vacuum the solvent and pass the mixture through a silica gel column using petroleum ether:dichloromethane (10:1) as the developing solvent to obtain the target compound A4 (HPLC purity 99.78%) as a dark red solid. MALDI-TOF-MS results: molecular ion peak: 932.4222; elemental analysis results: theoretical value: C, 86.271; H, 5.402; B, 2.321; N, 6.012 (%); experimental value: C, 86.283; H, 5.409; B, 2.333; N, 6.015 (%).

[0113] Synthesis Example 2 Synthesis of Compound A8

[0114]

[0115] This compound was synthesized similarly to Example 1 to obtain the target compound A8 (HPLC purity, 99.62%) as a dark red solid. MALDI-TOF-MS results showed: molecular ion peak: 954.4065; elemental analysis: theoretical values: C, 86.802; H, 5.071; B, 2.261; N, 5.872 (%); found values: C, 86.808; H, 5.083; B, 2.274; N, 5.885 (%).

[0116] Synthesis Example 3 Synthesis of Compound A11

[0117]

[0118] This compound was synthesized similarly to Example 1 to obtain the target compound A11 (HPLC purity, 99.19%) as a dark red solid. MALDI-TOF-MS results showed: molecular ion peak: 1126.4127; elemental analysis: theoretical values: C, 86.332; H, 4.291; B, 1.922; N, 7.461 (%); found values: C, 86.342; H, 4.297; B, 1.935; N, 7.472 (%).

[0119] Synthesis Example 4 Synthesis of Compound A14

[0120]

[0121] This compound was synthesized similarly to Example 1 to obtain the target compound A14 (HPLC purity, 99.37%) as a dark red solid. MALDI-TOF-MS results showed: molecular ion peak: 926.2847; elemental analysis: theoretical values: C, 84.251; H, 3.921; B, 2.331; N, 6.052; S, 3.461 (%); found values: C, 84.255; H, 3.929; B, 2.337; N, 6.058; S, 3.465 (%).

[0122] Synthesis Example 5 Synthesis of Compound A19

[0123]

[0124] This compound was synthesized similarly to Example 1 to obtain the target compound A19 (HPLC purity, 99.36%) as a dark red solid. MALDI-TOF-MS results showed: molecular ion peak: 1069.4487; elemental analysis: theoretical values: C, 86.443; H, 4.991; B, 2.021; N, 6.552 (%); found values: C, 86.447; H, 4.997; B, 2.028; N, 6.557 (%).

[0125] Synthesis Example 6 Synthesis of Compound A27

[0126]

[0127] This compound was synthesized similarly to Example 1 to obtain the target compound A27 (HPLC purity, 99.39%) as a dark red solid. MALDI-TOF-MS results showed: molecular ion peak: 1069.4487; elemental analysis: theoretical values: C, 86.442; H, 4.993; B, 2.023; N, 6.553 (%); found values: C, 86.453; H, 4.998; B, 2.032; N, 6.561 (%).

[0128] Synthesis Example 7 Synthesis of Compound A39

[0129]

[0130] This compound was synthesized similarly to Example 1 to obtain the target compound A39 (HPLC purity, 99.12%) as a dark red solid. MALDI-TOF-MS results showed: molecular ion peak: 908.3283; elemental analysis: theoretical values: C, 87.241; H, 4.221; B, 2.382; N, 6.171 (%); found values: C, 87.25; H, 4.23; B, 2.385; N, 6.184 (%).

[0131] Synthesis Example 8 Synthesis of Compound A43

[0132]

[0133] In a two-necked flask, under a nitrogen atmosphere, 1-bromo-3-chloro-4-fluoro-2-iodobenzene (10 mmol), I1 (10 mmol), and cesium carbonate (40 mmol) were dissolved in 150 mL of N,N-dimethylformamide (DMF). The temperature was raised to 150°C and the reaction was allowed to proceed for 12 hours. After the reaction was completed, the mixture was cooled, poured into cold water, filtered, washed twice with 100 mL of water, and then twice with 10 mL of methanol. The target compound A43-1 was obtained by drying.

[0134] In a two-necked flask under nitrogen, compound A43-1 (10 mmol), diphenylamine (10 mmol), trisdibenzylideneacetone dipalladium (1 mmol), tri-tert-butylphosphine tetrafluoroborate (2 mmol), and sodium tert-butoxide (12 mmol) were added sequentially. 100 ml of dry toluene was added and the temperature was raised to 110°C. The reaction was allowed to proceed for 12 hours. After cooling, the organic phase was separated and collected, dried over anhydrous sodium sulfate, filtered, concentrated, and separated by silica gel column development with petroleum ether:dichloromethane = 10:1 to obtain compound A43-2.

[0135] In a two-necked flask under nitrogen, compound A43-2 (5 mmol) was dissolved in 10 ml of dry tetrahydrofuran, cooled to -78°C, and a pentane solution of n-butyllithium (1 M, 6 ml) was added. The reaction was allowed to proceed at this temperature for 1 hour. 9-Fluorenone was dissolved in 40 ml of dry tetrahydrofuran, previously cooled to -78°C. This solution was then slowly injected into the A43-2 solution at -78°C. The mixture was slowly warmed to room temperature and allowed to react 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 100 ml of glacial acetic acid and 10 ml of concentrated hydrochloric acid were added. The mixture was then heated to reflux. After 2 hours of reaction, the mixture 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, filtered, concentrated, and separated by silica gel column chromatography using a 5:1 ratio of petroleum ether to dichloromethane to obtain compound A43-3.

[0136] Compound A43-3 (1 mmol) was dissolved in 20 mL of tert-butylbenzene in a sealed tube. After cooling to -78°C, tert-butyllithium in pentane (1 M, 2.5 mL) was added and the mixture was heated to 30°C for 1 hour. The mixture was cooled again to -78°C and slowly added with boron tribromide (3 mmol). The mixture was then heated to 30°C and stirred for 1 hour. After cooling to 0°C, diisopropylethylamine (5 mmol) was added and the mixture was heated to 160°C for 12 hours. The solvent was removed in vacuo and the mixture was passed through a silica gel column using petroleum ether:dichloromethane (10:1) as the developing solvent to obtain the target compound A43 (HPLC purity 99.11%) as a dark red solid. MALDI-TOF-MS results: molecular ion peak: 934.4378; elemental analysis results: theoretical value: C, 86.092; H, 5.613; B, 2.311; N, 5.993 (%); experimental value: C, 86.102; H, 5.617; B, 2.321; N, 6.004 (%).

[0137] Synthesis Example 9 Synthesis of Compound A51

[0138]

[0139] This compound was synthesized similarly to Example 8 to obtain the target compound A51 (HPLC purity, 99.72%) as a dark red solid. MALDI-TOF-MS results showed: molecular ion peak: 900.269; elemental analysis: theoretical values: C, 84.012; H, 3.813; B, 2.402; N, 6.223; S, 3.562 (%); found values: C, 84.025; H, 3.82; B, 2.405; N, 6.226; S, 3.571 (%).

[0140] Synthesis Example 10 Synthesis of Compound A59

[0141]

[0142] This compound was synthesized similarly to Example 8 to obtain the target compound A59 (HPLC purity, 99.46%) as a dark red solid. MALDI-TOF-MS results showed: molecular ion peak: 956.3283; elemental analysis: theoretical values: C, 87.883; H, 4.001; B, 2.261; N, 5.863 (%); found values: C, 87.889; H, 4.009; B, 2.272; N, 5.867 (%).

[0143] Synthesis Example 11 Synthesis of Compound A64

[0144]

[0145] The synthesis method of this compound is similar to that of Example 8, and the target compound A64 (HPLC analysis purity: 99.22%) is obtained, which is a dark red solid. MALDI-TOF-MS result: molecular ion peak: 1128.4283; elemental analysis result: theoretical values: C, 86.181; H, 4.462; B, 1.923; N, 7.442 (%) ; experimental values: C, 86.194; H, 4.47; B, 1.933; N, 7.449 (%).

[0146] Synthesis of Compound B1 in Synthesis Example 12

[0147]

[0148] The synthesis method of this compound is similar to that of Example 1, and the target compound B1 (HPLC analysis purity: 99.61%) is obtained, which is a dark red solid. MALDI-TOF-MS result: molecular ion peak: 842.2813; elemental analysis result: theoretical values: C, 86.963; H, 3.832; B, 2.572; N, 6.652 (%) ; experimental values: C, 86.971; H, 3.838; B, 2.582; N, 6.658 (%).

[0149] Synthesis of Compound B7 in Synthesis Example 13

[0150]

[0151] The synthesis method of this compound is similar to that of Example 1, and the target compound B7 (HPLC analysis purity: 99.52%) is obtained, which is a dark red solid. MALDI-TOF-MS result: molecular ion peak: 1030.4378; elemental analysis result: theoretical values: C, 87.381; H, 5.082; B, 2.102; N, 5.432 (%) ; experimental values: C, 87.391; H, 5.093; B, 2.114; N, 5.437 (%).

[0152] Synthesis of Compound B16 in Synthesis Example 14

[0153]

[0154] The synthesis method of this compound is similar to that of Example 1, and the target compound B16 (HPLC analysis purity: 99.73%) is obtained, which is a dark red solid. MALDI-TOF-MS result: molecular ion peak: 994.3439; elemental analysis result: theoretical values: C, 88.142; H, 4.051; B, 2.171; N, 5.633 (%) ; experimental values: C, 88.146; H, 4.063; B, 2.179; N, 5.637 (%).

[0155] Synthesis of Compound B23 in Synthesis Example 15

[0156]

[0157] The synthesis method of this compound is similar to that of Example 1, and the target compound B23 (HPLC analysis purity: 99.6%) is obtained, which is a dark red solid. MALDI-TOF-MS result: molecular ion peak: 1007.3392; elemental analysis result: theoretical values: C, 87.003; H, 3.901; B, 2.151; N, 6.953 (%) ; experimental values: C, 87.013; H, 3.906; B, 2.157; N, 6.961 (%).

[0158] Synthesis of Compound B39 in Synthesis Example 16

[0159]

[0160] The synthesis method of this compound is similar to that of Example 1, and the target compound B39 (HPLC analysis purity: 99.6%) is obtained, which is a dark red solid. MALDI-TOF-MS result: molecular ion peak: 958.3439; elemental analysis result: theoretical values: C, 87.701; H, 4.211; B, 2.261; N, 5.843 (%) ; experimental values: C, 87.707; H, 4.223; B, 2.271; N, 5.849 (%).

[0161] Synthesis of Compound B42 in Synthesis Example 17

[0162]

[0163] The synthesis method of this compound is similar to that of Example 8, and the target compound B42 (HPLC analysis purity: 99.18%) is obtained, which is a dark red solid. MALDI-TOF-MS result: molecular ion peak: 972.4535; elemental analysis result: theoretical values: C, 86.421; H, 5.602; B, 2.222; N, 5.761 (%) ; experimental values: C, 86.431; H, 5.613; B, 2.232; N, 5.772 (%).

[0164] Synthesis Example 18 Synthesis of Compound B53

[0165]

[0166] The synthesis of this compound was similar to that of Example 8, and the target compound B53 (purity by HPLC analysis: 99.67%) was obtained as a dark red solid. MALDI-TOF-MS result: molecular ion peak: 874.2534; elemental analysis result: theoretical values: C, 83.771; H, 3.693; B, 2.473; N, 6.413; S, 3.671 (%) ; experimental values: C, 83.784; H, 3.696; B, 2.485; N, 6.415; S, 3.675 (%).

[0167] Synthesis Example 19 Synthesis of Compound B65

[0168]

[0169] The synthesis of this compound was similar to that of Example 1, and the target compound B65 (purity by HPLC analysis: 99.48%) was obtained as a dark red solid. MALDI-TOF-MS result: molecular ion peak: 956.4222; elemental analysis result: theoretical values: C, 86.622; H, 5.272; B, 2.261; N, 5.861 (%) ; experimental values: C, 86.633; H, 5.285; B, 2.266; N, 5.871 (%).

[0170] Synthesis Example 20 Synthesis of Compound B67

[0171]

[0172] The synthesis of this compound was similar to that of Example 1, and the target compound B67 (purity by HPLC analysis: 99.5%) was obtained as a dark red solid. MALDI-TOF-MS result: molecular ion peak: 1095.4644; elemental analysis result: theoretical values: C, 86.582; H, 5.063; B, 1.971; N, 6.391 (%) ; experimental values: C, 86.594; H, 5.074; B, 1.981; N, 6.402 (%).

[0173] Synthesis Example 21 Synthesis of Compound B75

[0174]

[0175] The synthesis method of this compound is similar to that of Example 1, and the target compound B75 (HPLC analysis purity 99.73%) is obtained, which is a dark red solid. MALDI-TOF-MS result: molecular ion peak: 1060.5787; elemental analysis result: theoretical values: C, 86.032; H, 6.652; B, 2.042; N, 5.281 (%) ; experimental values: C, 86.04; H, 6.661; B, 2.051; N, 5.292 (%).

[0176] Synthesis of Compound B82 in Synthesis Example 22

[0177]

[0178] The synthesis method of this compound is similar to that of Example 8, and the target compound B82 (HPLC analysis purity 99.19%) is obtained, which is a dark red solid. MALDI-TOF-MS result: molecular ion peak: 848.3283; elemental analysis result: theoretical values: C, 86.343; H, 4.511; B, 2.551; N, 6.603 (%) ; experimental values: C, 86.352; H, 4.517; B, 2.555; N, 6.614 (%).

[0179] Synthesis of Compound B88 in Synthesis Example 23

[0180]

[0181] The synthesis method of this compound is similar to that of Example 8, and the target compound B88 (HPLC analysis purity 99.01%) is obtained, which is a dark red solid. MALDI-TOF-MS result: molecular ion peak: 860.3283; elemental analysis result: theoretical values: C, 86.531; H, 4.453; B, 2.511; N, 6.511 (%) ; experimental values: C, 86.543; H, 4.459; B, 2.517; N, 6.524 (%).

[0182] Synthesis of Compound C3 in Synthesis Example 24

[0183]

[0184] The synthesis method of this compound is similar to that of Example 1, and the target compound C3 (HPLC analysis purity 99.32%) is obtained, which is a dark red solid. MALDI-TOF-MS result: molecular ion peak: 954.4065; elemental analysis result: theoretical values: C, 86.801; H, 5.071; B, 2.263; N, 5.873 (%) ; experimental values: C, 86.809; H, 5.084; B, 2.275; N, 5.877 (%).

[0185] Synthesis Example 25 Synthesis of Compound C12

[0186]

[0187] The synthesis method of this compound is similar to that of Example 1, and the target compound C12 (HPLC analysis purity 99.01%) is obtained, which is a dark red solid. MALDI-TOF-MS result: molecular ion peak: 1092.5474; elemental analysis result: theoretical values: C, 86.813; H, 6.092; B, 1.982; N, 5.132 (%) ; experimental values: C, 86.815; H, 6.098; B, 1.987; N, 5.137 (%).

[0188] Synthesis Example 26 Synthesis of Compound C20

[0189]

[0190] The synthesis method of this compound is similar to that of Example 1, and the target compound C20 (HPLC analysis purity 99.06%) is obtained, which is a dark red solid. MALDI-TOF-MS result: molecular ion peak: 994.3439; elemental analysis result: theoretical values: C, 88.142; H, 4.052; B, 2.171; N, 5.631 (%) ; experimental values: C, 88.152; H, 4.06; B, 2.181; N, 5.64 (%).

[0191] Synthesis Example 27 Synthesis of Compound C31

[0192]

[0193] The synthesis method of this compound is similar to that of Example 1, and the target compound C31 (HPLC analysis purity 99.76%) is obtained, which is a dark red solid. MALDI-TOF-MS result: molecular ion peak: 1139.4331; elemental analysis result: theoretical values: C, 87.451; H, 4.511; B, 1.902; N, 6.143 (%) ; experimental values: C, 87.455; H, 4.522; B, 1.909; N, 6.155 (%).

[0194] Synthesis Example 28 Synthesis of Compound C42

[0195]

[0196] The synthesis method of this compound was similar to that of Example 8, and the target compound C42 (HPLC analysis purity: 99.39%) was obtained as a dark red solid. MALDI-TOF-MS result: molecular ion peak: 894.3126; elemental analysis result: theoretical values: C, 87.263; H, 4.063; B, 2.422; N, 6.262 (%); experimental values: C, 87.274; H, 4.065; B, 2.432; N, 6.275 (%).

[0197] Synthesis of Compound C49 in Synthesis Example 29

[0198]

[0199] The synthesis method of this compound was similar to that of Example 8, and the target compound C49 (HPLC analysis purity: 99.56%) was obtained as a dark red solid. MALDI-TOF-MS result: molecular ion peak: 874.2534; elemental analysis result: theoretical values: C, 83.771; H, 3.692; B, 2.473; N, 6.411; S, 3.673 (%); experimental values: C, 83.775; H, 3.699; B, 2.479; N, 6.424; S, 3.677 (%).

[0200] Synthesis of Compound C57 in Synthesis Example 30

[0201]

[0202] The synthesis method of this compound was similar to that of Example 8, and the target compound C57 (HPLC analysis purity: 99.46%) was obtained as a dark red solid. MALDI-TOF-MS result: molecular ion peak: 1060.4155; elemental analysis result: theoretical values: C, 79.233; H, 5.513; B, 2.042; N, 5.282; Si, 7.942 (%); experimental values: C, 79.242; H, 5.522; B, 2.049; N, 5.286; Si, 7.948 (%).

[0203] Synthesis of Compound C60 in Synthesis Example 31

[0204]

[0205] The synthesis method of this compound is similar to that of Example 8, and the target compound C60 (HPLC analysis purity 99.13%) is obtained as a dark red solid. MALDI-TOF-MS result: molecular ion peak: 1178.444; elemental analysis result: theoretical values: C, 86.591; H, 4.453; B, 1.832; N, 7.133 (%) ; experimental values: C, 86.599; H, 4.465; B, 1.838; N, 7.139 (%).

[0206] Synthesis of Compound D4 in Synthesis Example 32

[0207]

[0208] The synthesis method of this compound is similar to that of Example 1, and the target compound D4 (HPLC analysis purity 99.66%) is obtained as a dark red solid. MALDI-TOF-MS result: molecular ion peak: 1116.5474; elemental analysis result: theoretical values: C, 87.093; H, 5.961; B, 1.943; N, 5.022 (%) ; experimental values: C, 87.104; H, 5.972; B, 1.954; N, 5.026 (%).

[0209] Synthesis of Compound D12 in Synthesis Example 33

[0210]

[0211] The synthesis method of this compound is similar to that of Example 1, and the target compound D12 (HPLC analysis purity 99.28%) is obtained as a dark red solid. MALDI-TOF-MS result: molecular ion peak: 948.3596; elemental analysis result: theoretical values: C, 87.351; H, 4.461; B, 2.281; N, 5.912 (%) ; experimental values: C, 87.359; H, 4.471; B, 2.287; N, 5.92 (%).

[0212] Synthesis of Compound D18 in Synthesis Example 34

[0213]

[0214] The synthesis method of this compound is similar to that of Example 1, and the target compound D18 (HPLC analysis purity 99.11%) is obtained, which is a dark red solid. MALDI-TOF-MS result: molecular ion peak: 948.269; elemental analysis result: theoretical values: C, 84.821; H, 3.611; B, 2.282; N, 5.911; S, 3.383 (%) ; experimental values: C, 84.831; H, 3.624; B, 2.287; N, 5.917; S, 3.387 (%).

[0215] Synthesis of Compound D34 in Synthesis Example 35

[0216]

[0217] The synthesis method of this compound is similar to that of Example 8, and the target compound D34 (HPLC analysis purity 99.44%) is obtained, which is a dark red solid. MALDI-TOF-MS result: molecular ion peak: 844.297; elemental analysis result: theoretical values: C, 86.751; H, 4.063; B, 2.561; N, 6.632 (%) ; experimental values: C, 86.759; H, 4.072; B, 2.566; N, 6.636 (%).

[0218] Synthesis of Compound D39 in Synthesis Example 36

[0219]

[0220] The synthesis method of this compound is similar to that of Example 8, and the target compound D39 (HPLC analysis purity 99.13%) is obtained, which is a dark red solid. MALDI-TOF-MS result: molecular ion peak: 1010.4691; elemental analysis result: theoretical values: C, 86.733; H, 5.581; B, 2.143; N, 5.543 (%) ; experimental values: C, 86.742; H, 5.591; B, 2.152; N, 5.555 (%).

[0221] Synthesis of Compound D48 in Synthesis Example 37

[0222]

[0223] The synthesis method of this compound is similar to that of Example 8, and the target compound D48 (HPLC analysis purity: 99.04%) was obtained as a dark red solid. MALDI-TOF-MS result: molecular ion peak: 950.2847; elemental analysis result: theoretical values: C, 84.642; H, 3.823; B, 2.272; N, 5.891; S, 3.371 (%) ; experimental values: C, 84.645; H, 3.831; B, 2.285; N, 5.903; S, 3.384 (%).

[0224] Synthesis of Compound D55 in Synthesis Example 38

[0225]

[0226] The synthesis method of this compound is similar to that of Example 8, and the target compound D55 (HPLC analysis purity: 99.77%) was obtained as a dark red solid. MALDI-TOF-MS result: molecular ion peak: 1006.3439; elemental analysis result: theoretical values: C, 88.281; H, 4.002; B, 2.151; N, 5.572 (%) ; experimental values: C, 88.295; H, 4.01; B, 2.16; N, 5.578 (%).

[0227] Synthesis of Compound E1 in Synthesis Example 39

[0228]

[0229] The synthesis method of this compound is similar to that of Example 1, and the target compound E1 (HPLC analysis purity: 99.22%) was obtained as a dark red solid. MALDI-TOF-MS result: molecular ion peak: 931.3079; elemental analysis result: theoretical values: C, 86.383; H, 3.792; B, 2.321; N, 7.523 (%) ; experimental values: C, 86.39; H, 3.8; B, 2.328; N, 7.53 (%).

[0230] Synthesis of Compound E4 in Synthesis Example 40

[0231]

[0232] The synthesis method of this compound is similar to that of Example 1, and the target compound E4 (HPLC analysis purity: 99.55%) was obtained as a dark red solid. MALDI-TOF-MS result: molecular ion peak: 1131.5583; elemental analysis result: theoretical values: C, 85.943; H, 5.973; B, 1.912; N, 6.193 (%) ; experimental values: C, 85.948; H, 5.984; B, 1.919; N, 6.201 (%).

[0233] Synthesis Example 41 Synthesis of Compound E7

[0234]

[0235] The synthesis method of this compound is similar to that of Example 1, and the target compound E7 (purity by HPLC analysis: 99.31%) is obtained, which is a dark red solid. MALDI-TOF-MS result: molecular ion peak: 993.4174; elemental analysis result: theoretical values: C, 85.813; H, 4.973; B, 2.183; N, 7.053 (%) ; experimental values: C, 85.823; H, 4.975; B, 2.195; N, 7.058 (%).

[0236] Synthesis Example 42 Synthesis of Compound E16

[0237]

[0238] The synthesis method of this compound is similar to that of Example 1, and the target compound E16 (purity by HPLC analysis: 99.36%) is obtained, which is a dark red solid. MALDI-TOF-MS result: molecular ion peak: 1033.3548; elemental analysis result: theoretical values: C, 87.143; H, 4.001; B, 2.092; N, 6.772 (%) ; experimental values: C, 87.15; H, 4.011; B, 2.095; N, 6.776 (%).

[0239] Synthesis Example 43 Synthesis of Compound E22

[0240]

[0241] The synthesis method of this compound is similar to that of Example 1, and the target compound E22 (purity by HPLC analysis: 99.79%) is obtained, which is a dark red solid. MALDI-TOF-MS result: molecular ion peak: 1046.3501; elemental analysis result: theoretical values: C, 86.052; H, 3.851; B, 2.071; N, 8.033 (%) ; experimental values: C, 86.059; H, 3.857; B, 2.077; N, 8.039 (%).

[0242] Synthesis Example 44 Synthesis of Compound E26

[0243]

[0244] The synthesis method of this compound is similar to that of Example 1, and the target compound E26 (HPLC analysis purity: 99.76%) is obtained, which is a dark red solid. MALDI-TOF-MS result: molecular ion peak: 997.3548; elemental analysis result: theoretical values: C, 86.671; H, 4.143; B, 2.171; N, 7.023 (%) ; experimental values: C, 86.685; H, 4.154; B, 2.176; N, 7.026 (%).

[0245] Synthesis of Compound E32 in Synthesis Example 45

[0246]

[0247] The synthesis method of this compound is similar to that of Example 8, and the target compound E32 (HPLC analysis purity: 99.03%) is obtained, which is a dark red solid. MALDI-TOF-MS result: molecular ion peak: 911.3392; elemental analysis result: theoretical values: C, 85.633; H, 4.312; B, 2.372; N, 7.681 (%) ; experimental values: C, 85.645; H, 4.322; B, 2.385; N, 7.694 (%).

[0248] Synthesis of Compound E42 in Synthesis Example 46

[0249]

[0250] The synthesis method of this compound is similar to that of Example 8, and the target compound E42 (HPLC analysis purity: 99.05%) is obtained, which is a dark red solid. MALDI-TOF-MS result: molecular ion peak: 897.2871; elemental analysis result: theoretical values: C, 84.303; H, 3.713; B, 2.412; N, 7.803; O, 1.781 (%) ; experimental values: C, 84.311; H, 3.716; B, 2.421; N, 7.805; O, 1.786 (%).

[0251] Synthesis of Compound E51 in Synthesis Example 47

[0252]

[0253] The synthesis method of this compound is similar to that of Example 8, and the target compound E51 (HPLC analysis purity: 99.25%) is obtained, which is a dark red solid. MALDI-TOF-MS result: molecular ion peak: 1265.4549; elemental analysis result: theoretical values: C, 86.331; H, 4.222; B, 1.712; N, 7.743 (%) ; experimental values: C, 86.338; H, 4.227; B, 1.715; N, 7.747 (%).

[0254] Synthesis of Compound E53 in Synthesis Example 48

[0255]

[0256] The synthesis method of this compound is similar to that of Example 8, and the target compound E53 (HPLC analysis purity: 99.24%) is obtained, which is a dark red solid. MALDI-TOF-MS result: molecular ion peak: 1085.3861; elemental analysis result: theoretical values: C, 87.381; H, 4.182; B, 1.993; N, 6.453 (%) ; experimental values: C, 87.386; H, 4.195; B, 2.002; N, 6.46 (%).

[0257] Synthesis of Compound E55 in Synthesis Example 49

[0258]

[0259] The synthesis method of this compound is similar to that of Example 8, and the target compound E55 (HPLC analysis purity: 99.14%) is obtained, which is a dark red solid. MALDI-TOF-MS result: molecular ion peak: 909.3235; elemental analysis result: theoretical values: C, 85.822; H, 4.101; B, 2.383; N, 7.701 (%) ; experimental values: C, 85.833; H, 4.105; B, 2.387; N, 7.705 (%).

[0260] Synthesis of Compound F2 in Synthesis Example 50

[0261]

[0262] The synthesis method of this compound is similar to that of Example 1, and the target compound F2 (HPLC analysis purity 99.52%) is obtained, which is a dark red solid. MALDI-TOF-MS result: molecular ion peak: 902.2847; elemental analysis result: theoretical values: C, 83.833; H, 4.021; B, 2.402; N, 6.213; S, 3.553 (%) ; experimental values: C, 83.844; H, 4.029; B, 2.406; N, 6.219; S, 3.558 (%).

[0263] Synthesis of Compound F8 in Synthesis Example 51

[0264]

[0265] The synthesis method of this compound is similar to that of Example 1, and the target compound F8 (HPLC analysis purity 99.44%) is obtained, which is a dark red solid. MALDI-TOF-MS result: molecular ion peak: 1098.5038; elemental analysis result: theoretical values: C, 84.151; H, 5.873; B, 1.973; N, 5.101; S, 2.921 (%) ; experimental values: C, 84.157; H, 5.878; B, 1.977; N, 5.112; S, 2.932 (%).

[0266] Synthesis of Compound F18 in Synthesis Example 52

[0267]

[0268] The synthesis method of this compound is similar to that of Example 1, and the target compound F18 (HPLC analysis purity 99.06%) is obtained, which is a dark red solid. MALDI-TOF-MS result: molecular ion peak: 996.3265; elemental analysis result: theoretical values: C, 83.142; H, 4.252; B, 2.171; N, 5.621; O, 1.612; S, 3.222 (%) ; experimental values: C, 83.151; H, 4.255; B, 2.185; N, 5.626; O, 1.621; S, 3.228 (%).

[0269] Synthesis of Compound F23 in Synthesis Example 53

[0270]

[0271] The synthesis method of this compound is similar to that of Example 1, and the target compound F23 (HPLC analysis purity 99.58%) is obtained, which is a dark red solid. MALDI-TOF-MS result: molecular ion peak: 973.3184; elemental analysis result: theoretical values: C, 85.113; H, 3.831; B, 2.222; N, 7.192; O, 1.642 (%) ; experimental values: C, 85.118; H, 3.844; B, 2.235; N, 7.199; O, 1.648 (%).

[0272] Synthesis of Compound F30 in Synthesis Example 54

[0273]

[0274] The synthesis method of this compound is similar to that of Example 8, and the target compound F30 (HPLC analysis purity 99.45%) is obtained, which is a dark red solid. MALDI-TOF-MS result: molecular ion peak: 922.4014; elemental analysis result: theoretical values: C, 84.611; H, 5.242; B, 2.341; N, 6.073; O, 1.731 (%) ; experimental values: C, 84.625; H, 5.247; B, 2.351; N, 6.076; O, 1.738 (%).

[0275] Synthesis of Compound F43 in Synthesis Example 55

[0276]

[0277] The synthesis method of this compound is similar to that of Example 8, and the target compound F43 (HPLC analysis purity 99.79%) is obtained, which is a dark red solid. MALDI-TOF-MS result: molecular ion peak: 988.3037; elemental analysis result: theoretical values: C, 81.383; H, 4.281; B, 2.192; N, 5.673; S, 6.483 (%) ; experimental values: C, 81.387; H, 4.289; B, 2.197; N, 5.679; S, 6.486 (%).

[0278] Synthesis of Compound F55 in Synthesis Example 56

[0279]

[0280] The synthesis method of this compound is similar to that of Example 8, and the target compound F55 (HPLC analysis purity 99.37%) is obtained, which is a dark red solid. MALDI-TOF-MS result: molecular ion peak: 988.3003; elemental analysis result: theoretical values: C, 85.031; H, 3.872; B, 2.193; N, 5.673; S, 3.241 (%) ; experimental values: C, 85.042; H, 3.881; B, 2.199; N, 5.682; S, 3.25 (%).

[0281] Synthesis of Compound A66 in Synthesis Example 57

[0282]

[0283] The synthesis method of this compound is similar to that of Example 1, and the target compound A66 (HPLC analysis purity 99.23%) is obtained, which is a dark red solid. MALDI-TOF-MS result: molecular ion peak: 1192.5787; elemental analysis result: theoretical values: C, 87.581; H, 5.911; B, 1.811; N, 4.702 (%) ; experimental values: C, 87.586; H, 5.925; B, 1.817; N, 4.714 (%).

[0284] Synthesis of Compound C61 in Synthesis Example 58

[0285]

[0286] The synthesis method of this compound is similar to that of Example 1, and the target compound C61 (HPLC analysis purity 99.77%) is obtained, which is a dark red solid. MALDI-TOF-MS result: molecular ion peak: 1130.4691; elemental analysis result: theoretical values: C, 88.143; H, 4.991; B, 1.913; N, 4.951 (%) ; experimental values: C, 88.149; H, 4.999; B, 1.925; N, 4.959 (%).

[0287] Synthesis of Compound D57 in Synthesis Example 59

[0288]

[0289] The synthesis method of this compound is similar to that of Example 1, and the target compound D57 (HPLC analysis purity 99.35%) is obtained, which is a dark red solid. MALDI-TOF-MS result: molecular ion peak: 1130.4691; elemental analysis result: theoretical values: C, 88.142; H, 4.992; B, 1.912; N, 4.952 (%) ; experimental values: C, 88.153; H, 5.004; B, 1.92; N, 4.96 (%).

[0290] Synthesis of Compound E57 in Synthesis Example 60

[0291]

[0292] The synthesis method of this compound is similar to that of Example 1, and the target compound E57 (HPLC analysis purity 99.3%) is obtained, which is a dark red solid. MALDI-TOF-MS result: molecular ion peak: 1169.48; elemental analysis result: theoretical values: C, 87.263; H, 4.911; B, 1.852; N, 5.991 (%) ; experimental values: C, 87.268; H, 4.921; B, 1.863; N, 5.995 (%).

[0293] Synthesis of Compound A70 in Synthesis Example 61

[0294]

[0295] The synthesis method of this compound is similar to that of Example 1, and the target compound A70 (HPLC analysis purity 99.16%) is obtained, which is a dark red solid. MALDI-TOF-MS result: molecular ion peak: 794.2562; elemental analysis result: theoretical values: C, 83.151; H, 3.552; B, 2.721; N, 10.582 (%) ; experimental values: C, 83.155; H, 3.555; B, 2.732; N, 10.578 (%).

[0296] Synthesis of Compound C67 in Synthesis Example 62

[0297]

[0298] The synthesis method of this compound is similar to that of Example 1, and the target compound C67 (HPLC analysis purity 99.04%) is obtained, which is a dark red solid. MALDI-TOF-MS result: molecular ion peak: 844.2718; elemental analysis result: theoretical values: C, 83.912; H, 3.581; B, 2.562; N, 9.951 (%) ; experimental values: C, 83.921; H, 3.578; B, 2.576; N, 9.985 (%).

[0299] Synthesis Example 63 Synthesis of Compound D61

[0300]

[0301] The synthesis method of this compound is similar to that of Example 1, and the target compound D61 (purity by HPLC analysis: 99.11%) was obtained as a dark red solid. MALDI-TOF-MS result: molecular ion peak: 843.2766; elemental analysis result: theoretical values: C, 85.423; H, 3.710; B, 2.565; N, 8.301 (%) ; experimental values: C, 85.433; H, 3.707; B, 2.566; N, 8.310 (%).

[0302] Synthesis Example 64 Synthesis of Compound E57

[0303]

[0304] The synthesis method of this compound is similar to that of Example 1, and the target compound E64 (purity by HPLC analysis: 99.25%) was obtained as a dark red solid. MALDI-TOF-MS result: molecular ion peak: 883.2827; elemental analysis result: theoretical values: C, 82.922; H, 3.534; B, 2.445; N, 11.101 (%) ; experimental values: C, 82.932; H, 3.534; B, 2.455; N, 11.105 (%).

[0305] Device Example

[0306] Next, 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.

[0307] 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.

[0308] The material of the anode 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 material of the cathode 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 between them.

[0309] 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 of a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL).

[0310] 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.

[0311] The light-emitting layer includes light-emitting dyes (i.e., dopants) 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.

[0312] 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 of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0313] Specifically, the preparation method of the organic electroluminescent device of the present invention includes the following steps:

[0314] 1. Ultrasonically treat the glass plate coated with the anode material in a commercial cleaning agent, rinse it in deionized water, ultrasonically remove oil 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;

[0315] 2. Place the glass plate with the anode in a vacuum chamber, evacuate to 1×10-5~9×10-3 Pa, and vacuum-evaporate 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;

[0316] 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.

[0317] 4. An electron blocking layer is vacuum-evaporated on the hole transport layer, and the evaporation rate is 0.1 - 0.5 nm / s.

[0318] 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 the method of co-evaporation from multiple sources, the evaporation rate of the host material, the evaporation rate of the sensitizer material, and the evaporation rate of the dye are adjusted to make the dye reach a preset doping ratio.

[0319] 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.

[0320] 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.

[0321] 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.

[0322] 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 television, a digital camera, a mobile phone, a tablet computer, etc. The advantages of the display device compared with the prior art are the same as those of the above organic electroluminescent device, and will not be elaborated here.

[0323] The organic electroluminescent device of the present invention is further introduced below through specific embodiments.

[0324] Embodiments 1 - 64 of the present invention are organic electroluminescent devices prepared using the compounds of the present invention, and Comparative Examples 1 - 3 are parallel comparison devices prepared using prior art compounds P1, P2, and P3 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:

[0325] Table 1:

[0326]

[0327]

[0328]

[0329]

[0330] Among them, the anode material is ITO; the hole injection layer material is HI, with a general total thickness of 5 - 30 nm, and is designed to be 5 nm in the embodiments of the present invention; the hole transport layer material is HT, with a total thickness generally of 5 - 100 nm, and is designed to be 35 nm in the embodiments of the present invention; the electron blocking layer material is EBL, with a total thickness generally of 5 - 20 nm, and is designed to be 20 nm in the embodiments of the present invention, including EBL-1 and EBL-2, where EBL-1 is 10 nm and EBL-2 is 10 nm; the Host organic light-emitting layer is a wide-bandgap host material, and the thickness of the organic light-emitting layer is generally 1 - 100 nm, and is designed to be 30 nm in the embodiments of the present invention; the hole blocking layer material is HBL, with a total thickness generally of 5 - 20 nm, and is designed to be 10 nm in the embodiments of the present invention; the electron transport layer material is ET, with a thickness generally of 5 - 100 nm, and is designed to be 25 nm in the embodiments of the present invention; the electron injection layer and cathode materials are selected as LiF (0.5 nm) and metallic aluminum (150 nm). The structural formulas of various organic materials used in the above-mentioned respective embodiments are as follows:

[0331]

[0332]

[0333] The device performances prepared in Examples 1 - 64 and Comparative Examples 1 - 3 of the present invention are shown in Table 2 below:

[0334] Table 2:

[0335]

[0336]

[0337]

[0338] Compared with Comparative Example 1, a spiro atom is introduced on one side of the N-B-N structure in the mother nucleus of the compound in the present invention, connecting the two benzene rings on both sides, eliminating the repulsion between the original hydrogen atoms, significantly enhancing the rigidity of the molecule, significantly narrowing the full width at half maximum (FWHM is 20 - 30 nm), and improving the luminescence efficiency (PLQY > 90%). Compared with Comparative Example 2, the compound in the present invention adopts a single B-atom MR core, controlling the light color at about 625 nm, showing a pure red light emission. Compared with Comparative Example 3, the compound in the present invention adopts a spirofluorene structure, connecting diphenyl by a ring, protecting the easily broken phenyl through ring formation, and significantly improving the stability in the device. The compound in the present invention has the following characteristics: due to the spatial structure of the tetrahedron of the spiro atom, the introduction of the spiro atom forms two orthogonal planes at the spiro atom, significantly increasing the intermolecular distance, reducing the intermolecular interaction force, and being able to reduce the interaction between the host and the dye and between dyes in the device, thereby significantly improving the luminescence efficiency and the lifetime of the device, meeting the application standards. Moreover, the lifetimes of different spiro atom fragments in the device are different. Using an indolocarbazole group fused with a B-N atom-doped naphthalene ring or anthracene ring can not only expand the π-conjugation of the whole molecule, shifting the light color to a pure red light emission with a standard of 620 - 630 nm, but also, due to the introduction of B-N atoms, further localize the HOMO and LUMO on the atoms, further enhancing the MR effect, significantly inhibiting the structural relaxation between the ground state and the excited state, further narrowing the full width at half maximum of the emission, and achieving an ultra-narrowband pure red light emission.

[0339] The above experimental data show that after the organic electroluminescent device prepared by applying the novel MR-TADF material provided by the present invention, while achieving good performance of high color purity and high luminescence efficiency of the device, it also realizes a low efficiency roll-off of the electroluminescent device and has an extremely long device lifetime, demonstrating the great advantage of the molecular structure in the present invention in improving the device efficiency and stability. Given its excellent efficiency, color purity and stability, the above compounds should have good application prospects.

[0340] 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.

[0341] Obviously, the above embodiments are merely examples given for clear illustration and not limitations on the implementation manners. For those of ordinary skill in the art, other different forms of changes or variations can be made based on the above description. It is not necessary and impossible to list all the implementation manners here. And the obvious changes or variations derived therefrom still fall 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, and Ring I each independently represent a benzene ring, a naphthalene ring, or an anthracene ring; Ring D, Ring E, Ring F, and Ring G each independently represent one of a C5-C20 aromatic ring and a C4-C20 heteroaromatic ring; Ring Z and ring W each independently represent one of a C5-C20 aromatic ring and a C4-C20 nitrogen-containing heteroaromatic ring; X and Y are each independently selected from a single bond, O, CO, SO2, S, NR1, CR2R3 or SiR4R5; The R1, R2, R3, R4, and R5 are not connected to 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 R1, R2, R3, R4, and R5 are each independently selected from one of the following groups, which are unsubstituted or R'-substituted: C1-C36 chain alkyl, C3-C36 cycloalkyl, C6-C30 arylamino, C6-C60 aryl, C6-C60 aryloxy, and C5-C60 heteroaryl; m and n are each independently 0 or 1; R a 、R b 、R c 、R d 、R e 、R f 、R g 、R i 、R z 、R w Each independently represents a single substituent up to the maximum allowed number of substituent groups; R a 、R b 、R c 、R d 、R e 、R f 、R g 、R i 、R z 、R w Each independently connected to the connected ring structure by a single bond or fusion connection; The R c With R d Not connected or connected in a ring; R e With R f Not connected or connected in a ring; R g With R i Not connected or connected in a ring; R z 、R w They are not connected or connected in a loop; R a 、R b 、R c 、R d 、R e 、R f 、R g 、R i 、R z 、R w Each is independently selected from hydrogen, deuterium, halogen, carbonyl, carboxyl, nitro, cyano, amino, or one of the following groups which are unsubstituted or R'-substituted: C1-C36 chain alkyl, C3-C36 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkoxy, C1-C10 alkylsilyl, C2-C10 alkenyl, C6-C30 arylsilyl, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C60 aryl, C6-C60 aryloxy, C5-C60 heteroaryl; Two adjacent R's are not connected or connected to form a ring; R' is selected from any one or a combination of two of deuterium, halogen, cyano, amino, C2-C20 alkenyl, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 thioalkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C6-C60 aryl, and C3-C60 heteroaryl.

2. The organic compound according to claim 1, characterized in that Having a structure as shown in formula (2-1) or formula (2-2): Among them, ring D, ring E, ring F, ring G, R a 、R c 、R d 、R e 、R f 、R g 、R i 、R z 、R w The definitions of , m, and n are the same as those in formula (1); Ring Z and ring W each independently represent one of a C6-C12 aromatic ring and a C6-C12 nitrogen-containing heteroaromatic ring; X is selected from a single bond, O, CO, SO2, S, NR1, CR2R3 or SiR4R5; Y is selected from a single bond, NR1 or CR2R3; and when X is a single bond, Y is selected from CO, SO2, S, NR1, CR2R3 or SiR4R5; Preferably, when X is a single bond, Y is selected from NR1 or CR2R3; More preferably, m is 0 or 1, X is selected from a single bond, NR1 or CR2R3; n is 1, Y is selected from a single bond; More preferably, ring D, ring E, ring F, and ring G each independently represent a C5-C12 aromatic ring or a C4-C10 heteroaromatic ring; and ring Z and ring W each independently represent a benzene ring, a naphthalene ring, an anthracene ring, a pyridine ring, a pyrazine ring, or a pyridazine ring.

3. The organic compound according to claim 1 or 2, characterized in that In formula (1), formula (2-1), and formula (2-2), the ring D, ring E, ring F, and ring G are each independently a structure represented by formula (a) or formula (b), and the dotted lines represent the fusion positions of the following groups in formula (1), formula (2), and formula (2-2): In formula (a), U 1 、U 2 、U 3 、U 4 Each independently selected from CR 1 or N, two adjacent R 1 They are not connected or connected to form a ring through chemical bonds; R 1 each independently selected from one of hydrogen, deuterium, cyano, halogen, amino, unsubstituted or R"-substituted C1-C20 chain 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, and unsubstituted or R"-substituted C3-C60 heteroaryl; In formula (b), X 1 Selected from O, S, NR 2 or CR 3 R 4 ; R 2 、R 3 、R 4 Not connected to adjacent groups or connected to form a ring through chemical bonds; R 3 With R 4 They are not connected or connected in a loop; R 2 、R 3 、R 4 Each is independently selected from one of unsubstituted or R"-substituted C1-C20 chain alkyl, unsubstituted or R"-substituted C3-C20 cycloalkyl, unsubstituted or R"-substituted C6-C60 aryl, and unsubstituted or R"-substituted C3-C60 heteroaryl; R" is selected from any one or a combination of two of deuterium, halogen, cyano, amino, C2-C20 alkenyl, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 thioalkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C6-C60 aryl, and C3-C60 heteroaryl.

4. The organic compound according to claim 3, characterized in that In formula (a), U 1 、U 2 、U 3 、U 4 Each independently selected from CR 1 , R 1 Each is independently selected from hydrogen, deuterium, cyano, halogen or a combination of one or two of the following substituents: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, phenyl, naphthyl, anthracenyl, benzanthryl, phenanthrenyl, triphenylenyl, pyrenyl, chrysene, peryl, fluoranthenyl, tetraphenylene, pentacene, benzopyrenyl, biphenyl, phenylene, terphenylene, triphenylene, tetraphenylene, fluorenyl , spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis- or trans-indenofluorenyl, trimerized indenyl, isotrimerized indenyl, spirotrimerized indenyl, spiroistrimerized indenyl, furyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridinyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo-5,6-quinolyl, benzo-6,7-quinolyl, benzo-7,8-quinolyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, Quinoxalinoimidazolyl, oxazolyl, benzoxazolyl, naphthoxazolyl, anthrazolyl, phenanthroxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazaanthryl, 2,7-diazapyrenyl, 2,3-diazapyrenyl, 1,6-diazapyrenyl, 1,8-diazapyrenyl, 4,5-diazapyrenyl, 4,5,9,10-tetraazaperyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarbolinyl, 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, pyrrole, piperidine, methoxy, or silyl; In formula (b), R 2 、R 3 、R 4 Each independently selected from one or two of the following substituents: halogen, cyano, 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, anthracenyl, benzanthryl, phenanthryl, triphenylenyl, pyrenyl, chrysene, peryl, fluoranthenyl, tetraphenyl, pentacene, biphenyl, phenylene, terphenyl, triphenylene, quaterphenyl, fluorenyl, spirobifluorenyl, furanyl, benzofuranyl, dibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, Pyridyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo-5,6-quinolyl, benzo-6,7-quinolyl, benzo-7,8-quinolyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, oxazolyl, benzoxazolyl, naphthoxazolyl, anthrazolyl, phenanthroxazolyl, 1,2-thiazolyl, 1,3-thiazolyl , benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, triazinyl, benzothiadiazolyl, 9,9-dimethylacridinyl, triarylamine, adamantane, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl, tetrahydropyrrole, piperidine, methoxy.

5. The organic compound according to claim 1 or 2, characterized in that The ring Z and the ring W are both benzene rings; or one of the ring Z and the ring W is a naphthalene ring and the other is a benzene ring; or one of the ring Z and the ring W is a pyridine ring and the other is a benzene ring; or one of the ring Z and the ring W is a naphthalene ring and the other is a pyridine ring; or both the ring Z and the ring W are pyridine rings; R z 、R w They are not connected or connected in a loop; The ring D, ring E, ring F, and ring G each independently represent a C6-C12 aromatic ring; preferably, the ring D, ring E, ring F, and ring G each independently are selected from any one of a benzene ring, a naphthalene ring, and a fluorene ring; The R z 、R w Each is independently selected from hydrogen, deuterium, halogen, cyano, amino, or one of the following groups which are unsubstituted or R'-substituted: C1-C6 chain alkyl, C3-C6 cycloalkyl, C1-C6 alkoxy, C1-C6 thioalkoxy, C1-C10 alkylsilyl, C2-C6 alkenyl, C6-C30 arylsilyl, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryl, C6-C30 aryloxy, C5-C30 heteroaryl; R' is selected from any one of deuterium, halogen, cyano, amino, C2-C10 alkenyl, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C6-C60 aryl, and C3-C60 heteroaryl; Preferably, the R z 、R w Each is independently selected from hydrogen, deuterium or a combination of one or two of the following substituents: cyano, halogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, 2-methylbutyl, trifluoromethyl, pentafluoroethyl, vinyl, propenyl, phenyl, naphthyl, anthracenyl, biphenyl, terphenyl, fluorenyl, spirobifluorenyl, carbazolyl, pyridyl, quinolyl, acridinyl, phenazinyl, phenothiazinyl, azacarbazolyl, phenanthroline, 1,3,5-triazinyl, 9,9-dimethylacridinyl, triarylamine, adamantane, fluorophenyl, methylphenyl, trimethylphenyl, tert-butylphenyl, cyanophenyl, tetrahydropyrrole, trimethylsilyl, triphenylsilyl, piperidine or methoxy.

6. The organic compound according to any one of claims 1 to 5, characterized in that The R a 、R b 、R c 、R d 、R e 、R f 、R g 、R i Each is independently selected from hydrogen, deuterium, halogen, cyano, amino, or one of the following groups which are unsubstituted or R'-substituted: C1-C6 chain 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; R' is selected from any one of deuterium, halogen, cyano, amino, C2-C10 alkenyl, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C6-C60 aryl, and C3-C60 heteroaryl; Preferably, the R a 、R b 、R c 、R d 、R e 、R f 、R g 、R i Each is independently selected from hydrogen, deuterium or a combination of one or two of the following substituents: halogen, cyano, 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, anthracenyl, benzanthryl, phenanthryl, triphenylenyl, pyrene, chrysene, peryl, fluoranthene, tetracene, pentacene, biphenyl, phenylene, terphenyl, triphenylene, quaterphenyl, fluorenyl, spirobifluorenyl, furanyl, benzofuranyl, dibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl oxazolyl, pyridinyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo-5,6-quinolyl, benzo-6,7-quinolyl, benzo-7,8-quinolyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, oxazolyl, benzoxazolyl, naphthoxazolyl, anthrazolyl, phenanthroxazolyl, 1,2-thiazolyl, 1,3-thiazolyl oxazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, triazinyl, benzothiadiazolyl, 9,9-dimethylacridinyl, triarylamine, adamantane, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl, tetrahydropyrrole, piperidine, methoxy; The R1, R2, R3, R4, and R5 are each independently selected from one or a combination of two of the following substituents: halogen, cyano, 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, anthracenyl, benzanthryl, phenanthryl, triphenylenyl, pyrene, chrysene, peryl, fluoranthenyl, tetraphenyl, pentacene, biphenyl, phenylene, terphenyl, triphenylene, quaternaryl, fluorenyl, spirobifluorenyl, furanyl, benzofuranyl, dibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazole yl, indenocarbazolyl, pyridyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo-5,6-quinolyl, benzo-6,7-quinolyl, benzo-7,8-quinolyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, oxazolyl, benzoxazolyl, naphthoxazolyl, anthrazolyl, phenanthroxazolyl, 1,2-thiazolyl, 1,3 -thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, triazinyl, benzothiadiazolyl, 9,9-dimethylacridinyl, triarylamine, adamantane, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl, tetrahydropyrrole, piperidine, methoxy.

7. The organic compound according to claim 1, characterized in that Selected from the following specific structural compounds:

8. Use of the compound according to any one of claims 1 to 7 as a functional material in an organic electronic device, wherein the organic electronic device is an organic electroluminescent device, an optical sensor, a solar cell, an organic thin film transistor or an organic field effect transistor; Furthermore, the compound is used as a light-emitting layer material in an organic electroluminescent device, specifically as a light-emitting material in the light-emitting layer.

9. An organic electroluminescent device comprising a first electrode, a second electrode, and one or more light-emitting functional layers interposed between the first electrode and the second electrode, wherein the light-emitting functional layer contains the compound according to any one of claims 1 to 7; Furthermore, the light-emitting functional layer includes a hole transport region, a light-emitting layer, and an electron transport region, wherein 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 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 to 7.

10. A display device comprising the organic electroluminescent device according to claim 9.

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