An organic compound and use thereof

Abstract

The present application relates to an organic compound, and also relates to an organic electroluminescent device using the same. The organic compound of the present application has a structure as shown in formula (1). The compound of the present application has the characteristics of high luminescent efficiency, narrow light spectrum emission and high stability, and the organic electroluminescent device using the compound of the present application has higher external quantum efficiency and longer device life.

Description

Technical Field

[0001] This invention relates to an organic compound, and more particularly to a compound that can be used in organic electroluminescent devices, and also to organic electroluminescent devices employing the organic compound. Background Technology

[0002] As OLED technology continues to advance in both lighting and display fields, research into its core materials is receiving increasing attention. This is because a high-efficiency, long-lifespan OLED device is typically the result of optimized device structure and the combination of various organic materials. To fabricate OLED devices with lower driving voltages, better luminous efficiency, and longer lifespans, and to continuously improve OLED device performance, innovation in OLED device structure and manufacturing processes is necessary, along with ongoing research and innovation in the optoelectronic functional materials used in OLED devices to develop higher-performance functional materials. Based on this, the OLED materials community has been dedicated to developing new organic electroluminescent materials to achieve devices with low start-up voltages, high luminous efficiency, and superior lifespans.

[0003] In the selection of OLED light-emitting materials, singlet-state luminescent fluorescent materials have good lifetimes and low prices, but low efficiency; triplet-state luminescent phosphorescent materials have high efficiency, but are expensive, and the lifetime problem of blue light-emitting materials has not yet been solved. Adachi of Kyushu University in Japan proposed a new class of organic light-emitting materials, namely thermally activated delayed fluorescence (TADF) materials. This type of material utilizes donor-acceptor separation to obtain a smaller singlet-triplet bandgap (ΔE). ST (<0.3eV), thus enabling triplet excitons to be converted into singlet excitons for emission via reverse intersystem crossing (RISC), thereby achieving an internal quantum efficiency of 100%.

[0004] Existing technologies employ the "multiple resonance-induced thermally activated delayed fluorescence (MR-TADF)" strategy for designing novel compound structures. Patent applications CN107851724, CN108431984, and CN110407858, for example, have designed polycyclic aromatic compounds formed by linking multiple aromatic rings with boron, nitrogen, or oxygen atoms, thus constructing a unique rigid molecular system containing boron (B) and nitrogen (N) atoms. Compared to donor-acceptor type TADF compounds, MR-TADF molecules possess both high radiative transition rates and narrow half-maximum widths (WHMs). However, currently, BN-type MR molecules mostly emit light in the sky-blue to green region, with WHMs mostly around 30 nm, which fails to meet the requirements of the next-generation ultra-high-definition video standard BT.2020. Summary of the Invention

[0005] In one aspect, the present invention provides an organic compound having the structure shown in formula (1):

[0006]

[0007] Cycles Ar1, Ar2, Ar3, Ar4, and Ar5 are each independently selected from aromatic rings of C6 to C60 or heteroaromatic rings of C3 to C60;

[0008] Ring Ar3 and ring Ar4 are not connected, or they are connected by a single CC key, or by O, S or Se, or by CR7R8 or NR9;

[0009] Ring Ar1 and ring Ar2 are not connected, or are connected by a single CC key, or by O, S or Se, or by CR7R8 or NR9;

[0010] W represents C, CH, or CR. 10 ;

[0011] X1 represents a single bond, O, S, Se, or CR. 11 R 12 Si R 13 R 14 or NR 15 m is 0 or 1;

[0012] R1, R2, R3, R4, R5 and R6 are each independently selected from one of the following: hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C2-C30 aliphatic chain hydrocarbon amino, substituted or unsubstituted C4-C30 cyclic aliphatic chain hydrocarbon amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C60 arylboryl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl;

[0013] n1, n2, n3, n4, and n5 are each independently selected from integers between 0 and 10;

[0014] When n1, n2, n3, n4, and n5 are each an integer greater than 1, the corresponding multiple R1s, multiple R2s, multiple R3s, multiple R4s, and multiple R5s are either the same or different, and the multiple R1s are either not connected or connected in a cycle, the multiple R2s are either not connected or connected in a cycle, the multiple R3s are either not connected or connected in a cycle, the multiple R4s are either not connected or connected in a cycle, and the multiple R5s are either not connected or connected in a cycle.

[0015] R7, R8, R9 and R 10 Each is independently selected from one of the following: deuterium, halogen, cyano, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C2-C30 aliphatic chain hydrocarbon amino, substituted or unsubstituted C4-C30 cyclic aliphatic chain hydrocarbon amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl.

[0016] R 11 R 12 R 13 R 14 and R 15 Each of the following is independently selected from one of the following: substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C2-C30 aliphatic chain hydrocarbon amino, substituted or unsubstituted C4-C30 cyclic aliphatic chain hydrocarbon amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl.

[0017] When the above R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 R 12 R 13 R 14 and R 15 When each of the above substituents is present independently, each substituent is independently selected from one or a combination of two of the following: halogen, cyano, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C10 alkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryl, C6-C30 aryl, substituted or unsubstituted C6-C60 arylboryl, and C3-C30 heteroaryl.

[0018] Furthermore, in equation (1), n1, n2, n3 and n4 are each independently selected from integers from 1 to 5;

[0019] The R7, R8, R9 and R 10Each of the following is independently selected from deuterium, halogen, cyano, C1-C6 chain alkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl; preferably, R7 is selected from deuterium, halogen, cyano, and substituted or unsubstituted benzene ring; the R 11 R 12 R 13 R 14 and R 15 Each is independently selected from one of the following: substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl.

[0020] Preferably, R7, R8, R9 and R 10 Each is independently selected from one of deuterium, halogen, cyano, C1-C6 chain alkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl; the R 11 R 12 R 13 R 14 and R 15 Each is independently selected from one of the following: C1-C6 chain alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 arylamino, or substituted or unsubstituted C3-C30 heteroaryl;

[0021] More preferably, R7, R8, R9 and R 10 Each is independently selected from any one of deuterium, C1-C4 chain alkyl groups, substituted or unsubstituted benzene rings, naphthalene rings, and anthracene rings; the R 11 R 12 R 13 R 14 and R 15 Each is independently selected from any one of C1 to C4 chain alkyl groups, substituted or unsubstituted benzene rings, naphthalene rings, and anthracene rings;

[0022] Most preferably, R7, R8, R9 and R 10 Each is independently a substituted or unsubstituted benzene ring; the R 11 R 12 R 13 R 14 and R 15 Each is an independently substituted or unsubstituted benzene ring.

[0023] Furthermore, in formula (1), preferably, ring Ar1, ring Ar2, ring Ar3, ring Ar4 and ring Ar5 are each independently selected from one of benzene ring, naphthalene ring, anthracene ring, fluorene ring, furan or thiophene.

[0024] Furthermore, the organic compounds of the present invention are preferably structures shown in any one of the following structural formulas (1-1), (1-2), (1-3), (1-4), (1-5), (1-6), (1-7), or (1-8):

[0025]

[0026]

[0027] In equations (1-1) to (1-8), R1-R6, R 10 -R 15 The definitions of Ar1-Ar5 and n1-n5 are the same as those in equation (1).

[0028] Further preferably, each of the rings Ar1, Ar2, Ar3, Ar4, and Ar5 is independently selected from an aromatic ring of C6 to C60 or a heteroaromatic ring of C3 to C30; even more preferably, each of the rings Ar1, Ar2, Ar3, Ar4, and Ar5 is independently selected from any one of a benzene ring, a naphthyl ring, anthracene ring, a fluorene ring, a furan, a benzofuran, a dibenzofuran, an indole, a benzoindole, a carbazole, an indole-carbazole, a benzothiophene, a dibenzothiophene, or a thiophene; more preferably, each of the rings Ar1, Ar2, Ar3, Ar4, and Ar5 is independently selected from any one of a benzene ring, a naphthyl ring, a dibenzofuran, a carbazole, or a dibenzothiophene. Most preferably, each of the rings Ar1, Ar2, Ar3, Ar4, and Ar5 is independently selected from a benzene ring.

[0029] Furthermore, R1, R2, R3, R4, R5, and R6 are each independently selected from the following substituent 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, cyano, halogen, phenyl, naphthyl, anthracene, benzo[a]anthrayl, phenanthrene, benzo[a]phenanthrene, pyrene, pyryl, peryl, fluoranyl, tetraphenyl, pentaphenyl, benzo[a]pyrene, biphenyl, amphyl, terphenyl, triphenyl, triphenyl. Tetraphenyl, fluorenyl, spirodifluorenyl, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis or trans indofluorenyl, trimerinyl, isotrimericininyl, spirotrimericininyl, spiroisotrimericininyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrroleyl, isoindoleyl, carbazoleyl, indocarbazoleyl, pyridyl, quinolinyl, isoquinolinyl, acridineyl, phenanthridineyl, benzo-5,6-quinolinyl, benzo-6,7-quinolinyl, benzo-7,8-quinolinyl, pyrazolyl, indazoleyl, imidazoleyl, benzimidazoleyl, naphthiazoleyl, phenanthreneimidazoleyl, pyridinimidazoleyl, pyrazine Imidazolyl, quinoxaloimidazolyl, oxazolyl, benzoxoxazolyl, naphthoxazolyl, anthraxoxazolyl, phenanthoxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxaloyl, 1,5-diazaanthrayl, 2,7-diazapyrene, 2,3-diazapyrene, 1,6-diazapyrene, 1,8-diazapyrene, 4,5-diazapyrene, 4,5,9,10-tetraazaperyl, pyrazinyl, phenazinyl, phenthiazinyl, naphridinyl, azacarbazolyl, benzocarbazolyl, phenanthrolinel, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl One of the following: 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,3-triazinyl, tetrazolyl, 1,2,4,5-tetraazinyl, 1,2,3,4-tetraazinyl, 1,2,3,5-tetraazinyl, purinyl, pteridyl, inazinyl, benzothiadiazolyl, diphenylboryl, dimilboryl, dipentafluorophenylboryl, di(2,4,6-triisopropylphenyl)boryl, or a combination of the above two groups.

[0030] The R7, R8, R9 and R 10Each of the following substituents is independently selected: 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, cyano, halogen, phenyl, naphthyl, anthracene, benzo[a]anthrayl, phenanthryl, benzo[a]phenanthryl, pyrene, pyryl, peryl, fluoranyl, tetraphenyl, pentaphenyl, benzo[a]pyrene, biphenyl, amphyl, terphenyl, triphenyl, tetraphenyl, fluorene, spirophenyl Difluorenyl, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis or trans indofluorenyl, trimerinyl, isotrimericininyl, spirotrimericininyl, spiroisotrimericininyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thiopheneyl, benzothiopheneyl, isobenzothiopheneyl, dibenzothiopheneyl, pyrroleyl, isoindoleyl, carbazoleyl, indocarbazoleyl, pyridyl, quinolinyl, isoquinolinyl, acridineyl, phenanthridineyl, benzo-5,6-quinolinyl, benzo-6,7-quinolinyl, benzo-7,8-quinolinyl, pyrazolyl, indazoleyl, imidazoleyl, benzimidazoleyl, naphthizimidazoleyl, phenanthridine Imidazolyl, pyrazinimizolyl, quinoxalinimizolyl, oxazolyl, benzoxoxazolyl, naphthoxoxazolyl, anthraquinoxazolyl, phenanthoxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazaanthrayl, 2,7-diazapyrene, 2,3-diazapyrene, 1,6-diazapyrene, 1,8-diazapyrene, 4,5-diazapyrene, 4,5,9,10-tetraazaperyl, pyrazinyl, phenazinyl, phenthiazinyl, naphridinyl, azacarbazolyl, benzocarbazolyl, phenanthrolinel, 1, 2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,3-triazinyl, tetrazolyl, 1,2,4,5-tetraazinyl, 1,2,3,4-tetraazinyl, 1,2,3,5-tetraazinyl, purinyl, pteridyl, indazyl, benzothiadiazolyl, or a combination thereof;

[0031] The R mentioned 11 R 12 R 13 R 14 and R 15Each of the following substituents is independently selected: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, phenyl, naphthyl, anthracene, benzo[a]anthrayl, phenanthrene, benzo[a]phenanthrene, pyrene, pyryl, peryl, fluoranyl, tetraphenyl, pentaphenyl, benzo[a]pyrene, biphenyl, amphyl, terphenyl, triphenyl, tetraphenyl, fluorenyl, spirodifluorenyl. Dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis or trans indofluorenyl, trimerinyl, isotrimerininyl, spirotrimerininyl, spiroisotrimerininyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thiopheneyl, benzothiopheneyl, isobenzothiopheneyl, dibenzothiopheneyl, pyrroleyl, isoindoleyl, carbazoleyl, indocarbazoleyl, pyridinyl, quinolinyl, isoquinolinyl, acridineyl, phenanthridineyl, benzo-5,6-quinolinyl, benzo-6,7-quinolinyl, benzo-7,8-quinolinyl, pyrazolyl, indazoleyl, imidazoleyl, benzimidazoleyl, naphthiazoleyl, phenanthridineimidazole, pyridinazole , pyrazinibimidazolyl, quinoxalinibimidazolyl, oxazolyl, benzoxoxazolyl, naphthoxoxazolyl, anthraquinoxazolyl, phenanthoxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridinyl, benzopyridinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazaanthrayl, 2,7-diazapyrene, 2,3-diazapyrene, 1,6-diazapyrene, 1,8-diazapyrene, 4,5-diazapyrene, 4,5,9,10-tetraazaperyl, pyrazinyl, phenazinyl, phenthiazinyl, naphridinyl, azacarbazolyl, benzocarbazolyl, phenanthrolinel, 1,2, One of 3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,3-triazinyl, tetrazolyl, 1,2,4,5-tetraazinyl, 1,2,3,4-tetraazinyl, 1,2,3,5-tetraazinyl, purine, pteridine, indazyl, benzothiadiazolyl, or a combination of the above two groups.

[0032] More preferably, R1, R2, R3, R4, R5, and R6 are independently represented as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, trifluoromethyl, pentafluoroethyl, cyano, halogen, phenyl, naphthyl, anthracene, fluorenyl, spirodifluorenyl, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis- or trans-indofluorenyl, furanyl, benzofuranyl, thiophene, benzothiophene, pyrroleyl, isoyindolyl, carboxyl, etc. One of the following groups: azole, indocarbazolyl, pyridinyl, quinolinyl, isoquinolinyl, acridineyl, phenanthridineyl, pyrazolyl, indazoleyl, imidazolyl, benzimidazolyl-1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, 1,3,5-triazinyl, diphenylboryl, dimilboryl, dipentafluorophenylboryl, di(2,4,6-triisopropylphenyl)boryl, or a combination of the above two groups;

[0033] The R7, R8, R9 and R 10 Each of the following substituents is independently selected: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, trifluoromethyl, pentafluoroethyl, cyano, halogen, phenyl, naphthyl, anthracene, fluorenyl, spirodifluorenyl, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis or trans indofluorenyl, furanyl, benzofuranyl, thienyl, benzothienyl, pyrroleyl, isoyindolyl, carbazoleyl, indocarbazoleyl, pyridine One of the following groups: yl, quinolinyl, isoquinolinyl, acridineyl, phenanthridineyl, pyrazolyl, indazoleyl, imidazolyl, benzimidazolyl-1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, 1,3,5-triazinyl, diphenylboryl, dimilboryl, dipentafluorophenylboryl, di(2,4,6-triisopropylphenyl)boryl, or a combination thereof;

[0034] R 11 R 12 R 13 R 14 and R 15Each of the following substituents is independently selected: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, trifluoromethyl, pentafluoroethyl, cyano, halogen, phenyl, naphthyl, anthracene, fluorenyl, spirodifluorenyl, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis or trans indofluorenyl, furanyl, benzofuranyl, thienyl, benzothienyl, pyrroleyl, isoyindolyl, carbazoleyl, indocarbazoleyl, pyridine One of the following groups: yl, quinolinyl, isoquinolinyl, acridineyl, phenanthridineyl, pyrazolyl, indazoleyl, imidazoleyl, benzimidazolyl-1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, 1,3,5-triazinyl, diphenylboryl, dimilboryl, dipentafluorophenylboryl, di(2,4,6-triisopropylphenyl)boryl, or a combination of the above two groups.

[0035] Most preferably, R1, R2, R3, R4, R5 and R6 are each independently represented as one of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, trifluoromethyl, pentafluoroethyl, cyano, halogen, phenyl, naphthyl, anthracene, fluorenyl, spirodifluorenyl, carbazole, 1,3,5-triazinyl, diphenylboryl, dimilboryl, dipentafluorophenylboryl, di(2,4,6-triisopropylphenyl)boryl, or a combination of the above two groups;

[0036] The R7, R8, R9 and R 10 Each of the following substituents is independently selected from one of the following: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyano, phenyl, naphthyl, anthracene, fluorenyl, spirodifluorenyl, or a combination of two of the above groups.

[0037] The R 11 R 12 R 13 R 14 and R 15 Each of the following substituents is independently selected from one of the following: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, phenyl, naphthyl, anthracene, fluorenyl, spirodifluorenyl, or a combination of two of the above groups.

[0038] In this specification, the term "substituted or unsubstituted" can refer to a group that replaces one or more substituents. When there are multiple substituents, they can be selected from different substituents. In this invention, the same expression means the same thing, and the range of substituents to be selected is as shown above and will not be repeated here.

[0039] In this specification, the expression Ca to Cb represents that the group has a to b carbon atoms. Unless otherwise specified, the number of carbon atoms generally does not include the number of carbon atoms of the substituents.

[0040] In this specification, "each independently" means that when there are multiple subjects, they may be the same or different from each other.

[0041] Examples of halogens in this specification include fluorine, chlorine, bromine, and iodine.

[0042] Unless otherwise specified in this specification, aryl and heteroaryl groups include both monocyclic and fused-ring types. Monocyclic aryl refers to a molecule containing one or at least two phenyl groups. When the molecule contains at least two phenyl groups, the phenyl groups are independent of each other and connected by single bonds, such as phenyl, diphenyl, and terphenyl. Fused-ring aryl refers to a molecule containing at least two benzene rings, but the benzene rings are not independent of each other; instead, they are fused together by sharing ring edges, such as naphthyl and anthracene. Monocyclic heteroaryl refers to a molecule containing at least one heteroaryl group. When the molecule contains one heteroaryl group and other groups (such as aryl, heteroaryl, alkyl, etc.), the heteroaryl group and other groups are independent of each other and connected by single bonds, such as pyridine, furan, and thiophene. Fused-ring heteroaryl refers to a molecule formed by the fusion of at least one phenyl group and at least one heteroaryl group, or by the fusion of at least two heteroaryl rings, such as quinoline, isoquinoline, benzofuran, dibenzofuran, benzothiophene, and dibenzothiophene.

[0043] In this specification, the C6-C60 aryl group is preferably a C6-C30 aryl group, and the aryl group is preferably composed of phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthryl, indene, fluorenyl and their derivatives, fluoranthyl, triphenylene, pyrene, perylene, etc. The group is selected from the group consisting of 1-triphenyl-4-yl, 3-triphenyl-3-yl, 2-triphenyl-2-yl, 4-triphenyl-3-yl, 3-triphenyl-4-yl, 3-triphenyl-3-yl, and 3-triphenyl-2-yl; the naphthyl group includes 1-naphthyl or 2-naphthyl; the anthracene group is selected from the group consisting of 1-anthrayl, 2-anthrayl, and 9-anthrayl. The fluorenyl group is selected from the group consisting of 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, and 9-fluorenyl; the fluorenyl derivative is selected from the group consisting of 9,9'-dimethylfluorenyl, 9,9'-spirodifluorenyl, and benzo[a]fluorenyl; the pyrene group is selected from the group consisting of 1-pyrene, 2-pyrene, and 4-pyrene; the tetraphenyl group is selected from the group consisting of 1-tetraphenyl, 2-tetraphenyl, and 9-tetraphenyl.

[0044] In this specification, the C3-C60 heteroaryl group is preferably a C4-C30 heteroaryl group, and the heteroaryl group is preferably furanyl, thiophene, pyrrole, benzofuranyl, benzothiophene, isobenzofuranyl, indolyl, dibenzofuranyl, dibenzothiophene, carbazole, and their derivatives. The carbazole derivative is preferably 9-phenylcarbazole, 9-naphthylcarbazole, benzocarbazole, dibenzocarbazole, or indolocarbazole.

[0045] In this specification, aryloxy groups can be exemplified by the monovalent groups formed by the above-mentioned aryl and heteroaryl groups and oxygen.

[0046] In this specification, alkoxy groups can be exemplified by the aforementioned chain alkyl groups or monovalent groups composed of cycloalkyl groups and oxygen.

[0047] Examples of C6-C60 arylamine groups mentioned in this specification include: phenylamine, methylphenylamine, naphthylamine, anthraceneamine, phenanthreneamine, biphenylamine, etc.

[0048] Examples of C6-C60 heteroaryl amino groups mentioned in this specification include pyridinylamino, pyrimidinylamino, and dibenzofuranylamino.

[0049] Furthermore, the compounds of general formula (1) of the present invention may preferably be compounds with the following specific structures: A-1 to A-192, B-1 to B-57, C-1 to C-57, D-1 to D-57, E-1 to E-57, F-1 to F-51, G-1 to G-57, H-1 to H-57, these compounds are only representative:

[0050]

[0051]

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[0082]

[0083]

[0084] The structural features of this type of compound are as follows: In the parent structure of formula (1), the compound of this invention introduces at least one boron atom at the meta position of the boron atom in the central benzene ring, in the commonly used nitrogen-boron-nitrogen structure in the prior art. On the one hand, the different donor-acceptor properties of boron and nitrogen atoms cause a significant blue shift in the emitted light color. On the other hand, the newly added boron atom locks in the donor on one side, forming a planar rigid framework structure with the central benzene ring, which can reduce the relaxation degree of the excited state structure, thereby giving the target molecule both high luminescence efficiency, high color purity, and high stability. When a carbon atom, silicon atom, nitrogen atom, oxygen atom, sulfur atom, or selenium atom is introduced at the other meta position of the boron atom in the central benzene ring, on the one hand, the different electronegativity of these atoms is used to adjust the emitted light color. On the other hand, the donor on the other side is further locked in, so that the donors on both sides and the central benzene ring form a planar rigid framework structure, further reducing the relaxation degree of the excited state structure, thereby improving the luminescence efficiency, color purity, and stability of the target molecule. Compared with existing BN dye molecules, the target molecule has a significantly narrower half-width (14-20 nm) and a longer lifetime in organic optoelectronic devices.

[0085] In addition, the preparation process of the compounds of the present invention is simple and easy to implement, the raw materials are readily available, and it is suitable for mass production scale-up.

[0086] A second aspect of the invention also protects the use of compounds shown in any of the above general formulas (1), (1-1) to (1-8) as functional materials in organic electronic devices, including: organic electroluminescent devices, optical sensors, solar cells, lighting elements, organic thin-film transistors, organic field-effect transistors, organic thin-film solar cells, information tags, electronic artificial skin sheets, sheet-type scanners or electronic paper, preferably organic electroluminescent devices.

[0087] Thirdly, the present invention also provides an organic electroluminescent device, including a substrate, including a first electrode, a second electrode, and one or more organic layers inserted between the first electrode and the second electrode, wherein the organic layer contains a compound represented by any of the above general formulas (1), (1-1) to (1-8).

[0088] Specifically, one embodiment of the present invention provides an organic electroluminescent device, including a substrate, and an anode layer, a plurality of light-emitting functional layers and a cathode layer sequentially formed on the substrate; the light-emitting functional layers include a hole injection layer, a hole transport layer, a light-emitting layer and an electron transport layer, wherein the hole injection layer is formed on the anode layer, the hole transport layer is formed on the hole injection layer, the cathode layer is formed on the electron transport layer, and the light-emitting layer is located between the hole transport layer and the electron transport layer; wherein the light-emitting layer contains a compound of the general formula of the present invention shown in formula (1) above.

[0089] OLED devices prepared using the compounds of this invention have low start-up voltage, high luminous efficiency, and better lifespan, which can meet the current requirements of panel manufacturers for high-performance materials. Detailed Implementation

[0090] The specific preparation methods of the above-mentioned new compounds of the present invention will be described in detail below using several synthetic examples, but the preparation methods of the present invention are not limited to these synthetic examples.

[0091] All the chemical reagents used in this invention, such as petroleum ether, ethyl acetate, sodium sulfate, toluene, tetrahydrofuran, dichloromethane, acetic acid, and potassium carbonate, were purchased from Shanghai Titan Technology Co., Ltd. and Xilong Chemical Co., Ltd. The mass spectrometer used to determine the following compounds was a ZAB-HS type mass spectrometer (manufactured by Micromass, UK).

[0092] The synthesis method of the compounds of the present invention will be briefly described below.

[0093] Synthesis Examples

[0094] Representative synthetic pathways:

[0095]

[0096] More specifically, the following provides methods for synthesizing representative compounds of the present invention.

[0097] Synthesis Examples

[0098] Synthesis Example 1:

[0099] Synthesis of compound A1

[0100]

[0101] Under a nitrogen atmosphere, a pentane solution of n-butyllithium (24 mL, 2.50 M, 60 mmol) was slowly added to a tert-butylbenzene (150 mL) solution of a Br-substituted precursor (8.49 g, 15 mmol) at 0 °C, and the mixture was then heated to 25 °C and reacted for 1 hour. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (15.04 g, 60 mmol) was slowly added. The mixture was then heated to 60 °C and stirred for another 2 hours. N,N-diisopropylethylamine (15.52 g, 120 mmol) was added at room temperature, and the reaction was continued at 130 °C for 12 hours. A solution of phenyl magnesium bromide in tetrahydrofuran (60 mL, 1.0 M, 60 mmol) was added at room temperature, and the reaction was stopped after 6 hours. The solvent was then evaporated under vacuum, and the solution was passed through a silica gel column (eluent: dichloromethane: petroleum ether = 1:10) to give the target compound A-1 (2.86 g, 36% yield, HPLC purity 99%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 544.23. Elemental analysis results: Theoretical values: C, 86.07; H, 4.82; B, 3.97; N, 5.15; Experimental values: C, 86.05; H, 4.81; B, 3.98; N, 5.17.

[0102] Synthesis Example 2:

[0103] Synthesis of compound A-4

[0104]

[0105] Under a nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of a Br-substituted precursor (15 mmol) at 0 °C, and the mixture was then heated to 25 °C and reacted for 1 hour. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (60 mmol) was slowly added. The mixture was then heated to 60 °C and stirred for another 2 hours. N,N-diisopropylethylamine (120 mmol) was added at room temperature, and the reaction was continued at 130 °C for 12 hours. A tetrahydrofuran solution (60 mmol) of phenylmagnesium bromide was added at room temperature, and the reaction was stopped after 6 hours. The solvent was then evaporated under vacuum, and the solution was passed through a silica gel column (eluent: dichloromethane: petroleum ether = 1:10) to give the target compound A-4 (32% yield, HPLC purity 99%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 768.48. Elemental analysis results: Theoretical values: C, 85.94; H, 7.61; B, 2.81; N, 3.64; Experimental values: C, 85.92; H, 7.62; B, 2.82; N, 3.64.

[0106] Synthesis Example 3:

[0107] Synthesis of compound A8

[0108]

[0109] Under a nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of a Br-substituted precursor (15 mmol) at 0 °C, and the mixture was then heated to 25 °C and reacted for 1 hour. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (60 mmol) was slowly added. The mixture was then heated to 60 °C and stirred for another 2 hours. N,N-diisopropylethylamine (120 mmol) was added at room temperature, and the reaction was continued at 130 °C for 12 hours. A tetrahydrofuran solution (60 mmol) of phenylmagnesium bromide was added at room temperature, and the reaction was stopped after 6 hours. The solvent was then evaporated under vacuum, and the solution was passed through a silica gel column (eluent: dichloromethane: petroleum ether = 1:10) to give the target compound A-8 (33% yield, HPLC purity 99%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1072.60 Elemental analysis results: Theoretical values: C, 88.42; H, 6.95; B, 2.01; N, 2.61; Experimental values: C, 88.44; H, 6.96; B, 2.00; N, 2.50.

[0110] Synthesis Example 4:

[0111] Synthesis of compound A10

[0112]

[0113] Under a nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of a Br-substituted precursor (15 mmol) at 0 °C, and the mixture was then heated to 25 °C and reacted for 1 hour. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (60 mmol) was slowly added. The mixture was then heated to 60 °C and stirred for another 2 hours. N,N-diisopropylethylamine (120 mmol) was added at room temperature, and the reaction was continued at 130 °C for 12 hours. A tetrahydrofuran solution (60 mmol) of phenylmagnesium bromide was added at room temperature, and the reaction was stopped after 6 hours. The solvent was then evaporated under vacuum, and the solution was passed through a silica gel column (eluent: dichloromethane: petroleum ether = 1:10) to give the target compound A-10 (23% yield, HPLC purity 99%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1212.52 Elemental analysis results: Theoretical values: C, 86.14; H, 5.15; B, 1.78; N, 6.93; Experimental values: C, 86.13; H, 5.13; B, 1.79; N, 6.95.

[0114] Synthesis Example 5:

[0115] Synthesis of compound A-13

[0116]

[0117] Under a nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of a Br-substituted precursor (15 mmol) at 0 °C, and the mixture was then heated to 25 °C and reacted for 1 hour. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (60 mmol) was slowly added. The mixture was then heated to 60 °C and stirred for another 2 hours. N,N-diisopropylethylamine (120 mmol) was added at room temperature, and the reaction was continued at 130 °C for 12 hours. A tetrahydrofuran solution (60 mmol) of phenylmagnesium bromide was added at room temperature, and the reaction was stopped after 6 hours. The solvent was then evaporated under vacuum, and the solution was passed through a silica gel column (eluent: dichloromethane: petroleum ether = 1:10) to give the target compound A-8 (34% yield, HPLC purity 99%) as an orange-yellow solid. MALDI-TOF-MS results: Molecular ion peak: 744.29 Elemental analysis results: Theoretical values: C, 88.73; H, 4.60; B, 2.90; N, 3.76; Experimental values: 88.72; H, 4.61; B, 2.92; N, 3.74.

[0118] Synthesis Example 6:

[0119] Synthesis of compound A-17

[0120]

[0121] Under a nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of a Br-substituted precursor (15 mmol) at 0 °C, and the mixture was then heated to 25 °C and reacted for 1 hour. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (60 mmol) was slowly added. The mixture was then heated to 60 °C and stirred for another 2 hours. N,N-diisopropylethylamine (120 mmol) was added at room temperature, and the reaction was continued at 130 °C for 12 hours. A tetrahydrofuran solution (60 mmol) of phenylmagnesium bromide was added at room temperature, and the reaction was stopped after 6 hours. The solvent was then evaporated under vacuum, and the solution was passed through a silica gel column (eluent: dichloromethane: petroleum ether = 1:10) to give the target compound A-17 (34% yield, HPLC purity 99%) as an orange-yellow solid. MALDI-TOF-MS results: Molecular ion peak: 772.51. Elemental analysis results: Theoretical values: C, 85.49; H, 8.09; B, 2.80; N, 3.63; Experimental values: C, 85.46; H, 8.11; B, 2.79; N, 3.63.

[0122] Synthesis Example 7:

[0123] Synthesis of compound A-21

[0124]

[0125] Under a nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of a Br-substituted precursor (15 mmol) at 0 °C, and the mixture was then heated to 25 °C and reacted for 1 hour. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (60 mmol) was slowly added. The mixture was then heated to 60 °C and stirred for another 2 hours. N,N-diisopropylethylamine (120 mmol) was added at room temperature, and the reaction was continued at 130 °C for 12 hours. A tetrahydrofuran solution (60 mmol) of phenylmagnesium bromide was added at room temperature, and the reaction was stopped after 6 hours. The solvent was then evaporated under vacuum, and the solution was passed through a silica gel column (eluent: dichloromethane: petroleum ether = 1:10) to give the target compound A-21 (20% yield, HPLC purity 99%) as an orange-yellow solid. MALDI-TOF-MS results: Molecular ion peak: 874.34. Elemental analysis results: Theoretical values: C, 86.51; H, 4.61; B, 2.47; N, 6.41; Experimental values: C, 86.50; H, 4.63; B, 2.46; N, 6.42.

[0126] Synthesis Example 8:

[0127] Synthesis of compound A-24

[0128]

[0129] Under a nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of a Br-substituted precursor (15 mmol) at 0 °C, and the mixture was then heated to 25 °C and reacted for 1 hour. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (60 mmol) was slowly added. The mixture was then heated to 60 °C and stirred for another 2 hours. N,N-diisopropylethylamine (120 mmol) was added at room temperature, and the reaction was continued at 130 °C for 12 hours. A tetrahydrofuran solution (60 mmol) of phenylmagnesium bromide was added at room temperature, and the reaction was stopped after 6 hours. The solvent was then evaporated under vacuum, and the solution was passed through a silica gel column (eluent: dichloromethane: petroleum ether = 1:10) to give the target compound A-24 (22% yield, HPLC purity 99%) as an orange-yellow solid. MALDI-TOF-MS results: Molecular ion peak: 874.34. Elemental analysis results: Theoretical values: C, 86.51; H, 4.61; B, 2.47; N, 6.41; Experimental values: C, 86.52; H, 4.61; B, 2.47; N, 6.40.

[0130] Synthesis Example 9:

[0131] Synthesis of compound A-44

[0132]

[0133] Under a nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of a Br-substituted precursor (15 mmol) at 0 °C, and the mixture was then heated to 25 °C and reacted for 1 hour. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (60 mmol) was slowly added. The mixture was then heated to 60 °C and stirred for another 2 hours. N,N-diisopropylethylamine (120 mmol) was added at room temperature, and the reaction was continued at 130 °C for 12 hours. A tetrahydrofuran solution (60 mmol) of phenylmagnesium bromide was added at room temperature, and the reaction was stopped after 6 hours. The solvent was then evaporated under vacuum, and the solution was passed through a silica gel column (eluent: dichloromethane: petroleum ether = 1:10) to give the target compound A-44 (25% yield, HPLC purity 99%) as an orange-yellow solid. MALDI-TOF-MS results: Molecular ion peak: 874.34 Elemental analysis results: Theoretical values: C, 86.51; H, 4.61; B, 2.47; N, 6.41; Experimental values: C, 86.51; H, 4.62; B, 2.48; N, 6.39.

[0134] Synthesis Example 10:

[0135] Synthesis of compound A-55

[0136]

[0137] Under a nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of a Br-substituted precursor (15 mmol) at 0 °C, and the mixture was then heated to 25 °C and reacted for 1 hour. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (60 mmol) was slowly added. The mixture was then heated to 60 °C and stirred for another 2 hours. N,N-diisopropylethylamine (120 mmol) was added at room temperature, and the reaction was continued at 130 °C for 12 hours. A tetrahydrofuran solution (60 mmol) of phenylmagnesium bromide was added at room temperature, and the reaction was stopped after 6 hours. The solvent was then evaporated under vacuum, and the solution was passed through a silica gel column (eluent: dichloromethane: petroleum ether = 1:10) to give the target compound A-55 (40% yield, HPLC purity 99%) as an orange-yellow solid. MALDI-TOF-MS results: Molecular ion peak: 872.35 Elemental analysis results: Theoretical values: C, 89.46; H, 4.85; B, 2.48; N, 3.21; Experimental values: C, 89.48; H, 4.86; B, 2.47; N, 3.19.

[0138] Synthesis Example 11:

[0139] Synthesis of compound A-65

[0140]

[0141] Under a nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of a Br-substituted precursor (15 mmol) at 0 °C, and the mixture was then heated to 25 °C and reacted for 1 hour. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (60 mmol) was slowly added. The mixture was then heated to 60 °C and stirred for another 2 hours. N,N-diisopropylethylamine (120 mmol) was added at room temperature, and the reaction was continued at 130 °C for 12 hours. A tetrahydrofuran solution (60 mmol) of phenylmagnesium bromide was added at room temperature, and the reaction was stopped after 6 hours. The solvent was then evaporated under vacuum, and the solution was passed through a silica gel column (eluent: dichloromethane: petroleum ether = 1:10) to give the target compound A-65 (36% yield, HPLC purity 99%) as an orange-yellow solid. MALDI-TOF-MS results: Molecular ion peak: 696.29 Elemental analysis results: Theoretical values: C, 87.95; H, 4.92; B, 3.10; N, 4.02; Experimental values: C, 87.96; H, 4.95; B, 3.09; N, 4.00.

[0142] Synthesis Example 12:

[0143] Synthesis of compound A-70

[0144]

[0145] Under a nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of a Br-substituted precursor (15 mmol) at 0 °C, and the mixture was then heated to 25 °C and reacted for 1 hour. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (60 mmol) was slowly added. The mixture was then heated to 60 °C and stirred for another 2 hours. N,N-diisopropylethylamine (120 mmol) was added at room temperature, and the reaction was continued at 130 °C for 12 hours. A tetrahydrofuran solution (60 mmol) of phenylmagnesium bromide was added at room temperature, and the reaction was stopped after 6 hours. The solvent was then evaporated under vacuum, and the solution was passed through a silica gel column (eluent: dichloromethane: petroleum ether = 1:10) to give the target compound A-70 (33% yield, HPLC purity 99%) as an orange-yellow solid. MALDI-TOF-MS results: Molecular ion peak: 782.49 Elemental analysis results: Theoretical values: C, 85.93; H, 7.73; B, 2.76; N, 3.58; Experimental values: C, 85.93; H, 7.75; B, 2.77; N, 3.55.

[0146] Synthesis Example 13:

[0147] Synthesis of compound A-80

[0148]

[0149] Under a nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of a Br-substituted precursor (15 mmol) at 0 °C, and the mixture was then heated to 25 °C and reacted for 1 hour. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (60 mmol) was slowly added. The mixture was then heated to 60 °C and stirred for another 2 hours. N,N-diisopropylethylamine (120 mmol) was added at room temperature, and the reaction was continued at 130 °C for 12 hours. A tetrahydrofuran solution (60 mmol) of phenylmagnesium bromide was added at room temperature, and the reaction was stopped after 6 hours. The solvent was then evaporated under vacuum, and the solution was passed through a silica gel column (eluent: dichloromethane: petroleum ether = 1:10) to give the target compound A-80 (33% yield, HPLC purity 99%) as an orange-yellow solid. MALDI-TOF-MS results: Molecular ion peak: 576.22. Elemental analysis results: Theoretical values: C, 81.29; H, 4.55; B, 3.75; N, 4.86; Experimental values: C, 81.29; H, 4.56; B, 3.73; N, 4.88.

[0150] Synthesis Example 14:

[0151] Synthesis of compound A-81

[0152]

[0153] Under a nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of a Br-substituted precursor (15 mmol) at 0 °C, and the mixture was then heated to 25 °C and reacted for 1 hour. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (60 mmol) was slowly added. The mixture was then heated to 60 °C and stirred for another 2 hours. N,N-diisopropylethylamine (120 mmol) was added at room temperature, and the reaction was continued at 130 °C for 12 hours. A tetrahydrofuran solution (60 mmol) of phenylmagnesium bromide was added at room temperature, and the reaction was stopped after 6 hours. The solvent was then evaporated under vacuum, and the solution was passed through a silica gel column (eluent: dichloromethane: petroleum ether = 1:10) to give the target compound A-81 (26% yield, HPLC purity 99%) as an orange-yellow solid. MALDI-TOF-MS results: Molecular ion peak: 608.17. Elemental analysis results: Theoretical values: C, 76.99; H, 4.31; B, 3.55; N, 4.60; S, 10.54; Experimental values: C, 76.97; H, 4.30; B, 3.56; N, 4.58; S, 10.58.

[0154] Synthesis Example 15:

[0155] Synthesis of compound A-82

[0156]

[0157] Under a nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of a Br-substituted precursor (15 mmol) at 0 °C, and the mixture was then heated to 25 °C and reacted for 1 hour. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (60 mmol) was slowly added. The mixture was then heated to 60 °C and stirred for another 2 hours. N,N-diisopropylethylamine (120 mmol) was added at room temperature, and the reaction was continued at 130 °C for 12 hours. A tetrahydrofuran solution (60 mmol) of phenylmagnesium bromide was added at room temperature, and the reaction was stopped after 6 hours. The solvent was then evaporated under vacuum, and the solution was passed through a silica gel column (eluent: dichloromethane: petroleum ether = 1:10) to give the target compound A-82 (22% yield, HPLC purity 99%) as an orange-yellow solid. MALDI-TOF-MS results: Molecular ion peak: 702.19 Elemental analysis results: Theoretical values: C, 66.71; H, 3.73; B, 3.08; N, 3.99; Se, 22.49; Experimental values: C, 66.74; H, 3.71; B, 3.09; N, 3.98; Se, 22.52.

[0158] Synthesis Example 16:

[0159] Synthesis of compound A-85

[0160]

[0161] Under a nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of a Br-substituted precursor (15 mmol) at 0 °C, and the mixture was then heated to 25 °C and reacted for 1 hour. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (60 mmol) was slowly added. The mixture was then heated to 60 °C and stirred for another 2 hours. N,N-diisopropylethylamine (120 mmol) was added at room temperature, and the reaction was continued at 130 °C for 12 hours. A tetrahydrofuran solution (60 mmol) of phenylmagnesium bromide was added at room temperature, and the reaction was stopped after 6 hours. The solvent was then evaporated under vacuum, and the solution was passed through a silica gel column (eluent: dichloromethane: petroleum ether = 1:10) to give the target compound A-85 (31% yield, HPLC purity 99%) as an orange-yellow solid. MALDI-TOF-MS results: Molecular ion peak: 908.34. Elemental analysis results: Theoretical values: C, 83.26; H, 5.10; B, 2.38; N, 3.08; Si, 6.18; Experimental values: C, 83.27; H, 5.11; B, 2.37; N, 3.09; Si, 6.16.

[0162] Synthesis Example 17:

[0163] Synthesis of compound A-87

[0164]

[0165] Under a nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of a Br-substituted precursor (15 mmol) at 0 °C, and the mixture was then heated to 25 °C and reacted for 1 hour. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (60 mmol) was slowly added. The mixture was then heated to 60 °C and stirred for another 2 hours. N,N-diisopropylethylamine (120 mmol) was added at room temperature, and the reaction was continued at 130 °C for 12 hours. A tetrahydrofuran solution (60 mmol) of phenylmagnesium bromide was added at room temperature, and the reaction was stopped after 6 hours. The solvent was then evaporated under vacuum, and the solution was passed through a silica gel column (eluent: dichloromethane: petroleum ether = 1:10) to give the target compound A-87 (30% yield, HPLC purity 99%) as an orange solid. MALDI-TOF-MS results: Molecular ion peak: 560.22 Elemental analysis results: Theoretical values: C, 83.61; H, 4.68; B, 3.86; N, 5.00; Experimental values: C, 83.60; H, 4.66; B, 3.87; N, 5.02.

[0166] Synthesis Example 18:

[0167] Synthesis of compound A-94

[0168]

[0169] Under a nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of a Br-substituted precursor (15 mmol) at 0 °C, and the mixture was then heated to 25 °C and reacted for 1 hour. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (60 mmol) was slowly added. The mixture was then heated to 60 °C and stirred for another 2 hours. N,N-diisopropylethylamine (120 mmol) was added at room temperature, and the reaction was continued at 130 °C for 12 hours. A tetrahydrofuran solution (60 mmol) of phenylmagnesium bromide was added at room temperature, and the reaction was stopped after 6 hours. The solvent was then evaporated under vacuum, and the solution was passed through a silica gel column (eluent: dichloromethane: petroleum ether = 1:10) to give the target compound A-87 (30% yield, HPLC purity 99%) as an orange-yellow solid. MALDI-TOF-MS results: Molecular ion peak: 724.27 Elemental analysis results: Theoretical values: C, 84.54; H, 4.73; B, 2.98; N, 3.87; Si, 3.88; Experimental values: C, 84.53; H, 4.75; B, 2.97; N, 3.88; Si, 3.89.

[0170] Synthesis Example 19:

[0171] Synthesis of compound A-155

[0172]

[0173] Under a nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of a Br-substituted precursor (15 mmol) at 0 °C, and the mixture was then heated to 25 °C and reacted for 1 hour. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (60 mmol) was slowly added. The mixture was then heated to 60 °C and stirred for another 2 hours. N,N-diisopropylethylamine (120 mmol) was added at room temperature, and the reaction was continued at 130 °C for 12 hours. A tetrahydrofuran solution (60 mmol) of phenylmagnesium bromide was added at room temperature, and the reaction was stopped after 6 hours. The solvent was then evaporated under vacuum, and the solution was passed through a silica gel column (eluent: dichloromethane: petroleum ether = 1:10) to give the target compound A-155 (31% yield, HPLC purity 99%) as an orange-yellow solid. MALDI-TOF-MS results: Molecular ion peak: 650.22. Elemental analysis results: Theoretical values: C, 83.10; H, 4.34; B, 3.32; N, 4.31; S, 4.93; Experimental values: C, 83.08; H, 4.35; B, 3.30; N, 4.321; S, 4.95.

[0174] Synthesis Example 20:

[0175] Synthesis of compound A-179

[0176]

[0177] Under a nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of a Br-substituted precursor (15 mmol) at 0 °C, and the mixture was then heated to 25 °C and reacted for 1 hour. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (60 mmol) was slowly added. The mixture was then heated to 60 °C and stirred for another 2 hours. N,N-diisopropylethylamine (120 mmol) was added at room temperature, and the reaction was continued at 130 °C for 12 hours. A tetrahydrofuran solution (60 mmol) of phenylmagnesium bromide was added at room temperature, and the reaction was stopped after 6 hours. The solvent was then evaporated under vacuum, and the solution was passed through a silica gel column (eluent: dichloromethane: petroleum ether = 1:10) to give the target compound A-179 (32% yield, HPLC purity 99%) as an orange-yellow solid. MALDI-TOF-MS results: Molecular ion peak: 821.41. Elemental analysis results: Theoretical values: C, 86.24; H, 6.01; B, 2.63; N, 5.11; Experimental values: C, 86.27; H, 6.00; B, 2.62; N, 5.11.

[0178] Synthesis Example 21:

[0179] Synthesis of compound A-180

[0180]

[0181] Under a nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of a Br-substituted precursor (15 mmol) at 0 °C, and the mixture was then heated to 25 °C and reacted for 1 hour. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (60 mmol) was slowly added. The mixture was then heated to 60 °C and stirred for another 2 hours. N,N-diisopropylethylamine (120 mmol) was added at room temperature, and the reaction was continued at 130 °C for 12 hours. A tetrahydrofuran solution (60 mmol) of phenylmagnesium bromide was added at room temperature, and the reaction was stopped after 6 hours. The solvent was then evaporated under vacuum, and the solution was passed through a silica gel column (eluent: dichloromethane: petroleum ether = 1:10) to give the target compound A-180 (34% yield, HPLC purity 99%) as an orange-yellow solid. MALDI-TOF-MS results: Molecular ion peak: 821.41. Elemental analysis results: Theoretical values: C, 86.24; H, 6.01; B, 2.63; N, 5.11; Experimental values: C, 86.26; H, 6.05; B, 2.59; N, 5.10.

[0182] Synthesis Example 22:

[0183] Synthesis of compound A-181

[0184]

[0185] Under a nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of a Br-substituted precursor (15 mmol) at 0 °C, and the mixture was then heated to 25 °C and reacted for 1 hour. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (60 mmol) was slowly added. The mixture was then heated to 60 °C and stirred for another 2 hours. N,N-diisopropylethylamine (120 mmol) was added at room temperature, and the reaction was continued at 130 °C for 12 hours. A tetrahydrofuran solution (60 mmol) of phenylmagnesium bromide was added at room temperature, and the reaction was stopped after 6 hours. The solvent was then evaporated under vacuum, and the solution was passed through a silica gel column (eluent: dichloromethane: petroleum ether = 1:10) to obtain the target compound A-181 (30% yield, HPLC purity 99%) as an orange-yellow solid. MALDI-TOF-MS results: Molecular ion peak: 821.41. Elemental analysis results: Theoretical values: C, 86.24; H, 6.01; B, 2.63; N, 5.11; Experimental values: C, 86.26; H, 6.05; B, 2.60; N, 5.09.

[0186] Synthesis Example 23:

[0187] Synthesis of compound A-182

[0188]

[0189] Under a nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of a Br-substituted precursor (15 mmol) at 0 °C, and the mixture was then heated to 25 °C and reacted for 1 hour. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (60 mmol) was slowly added. The mixture was then heated to 60 °C and stirred for another 2 hours. N,N-diisopropylethylamine (120 mmol) was added at room temperature, and the reaction was continued at 130 °C for 12 hours. A tetrahydrofuran solution (60 mmol) of phenylmagnesium bromide was added at room temperature, and the reaction was stopped after 6 hours. The solvent was then evaporated under vacuum, and the solution was passed through a silica gel column (eluent: dichloromethane: petroleum ether = 1:10) to give the target compound A-182 (34% yield, HPLC purity 99%) as an orange-yellow solid. MALDI-TOF-MS results: Molecular ion peak: 821.41. Elemental analysis results: Theoretical values: C, 86.24; H, 6.01; B, 2.63; N, 5.11; Experimental values: C, 86.26; H, 6.02; B, 2.61; N, 5.11.

[0190] Synthesis Example 24:

[0191] Synthesis of compound A-183

[0192]

[0193] Under a nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of a Br-substituted precursor (15 mmol) at 0 °C, and the mixture was then heated to 25 °C and reacted for 1 hour. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (60 mmol) was slowly added. The mixture was then heated to 60 °C and stirred for another 2 hours. N,N-diisopropylethylamine (120 mmol) was added at room temperature, and the reaction was continued at 130 °C for 12 hours. A tetrahydrofuran solution (60 mmol) of phenylmagnesium bromide was added at room temperature, and the reaction was stopped after 6 hours. The solvent was then evaporated under vacuum, and the solution was passed through a silica gel column (eluent: dichloromethane: petroleum ether = 1:10) to give the target compound A-183 (34% yield, HPLC purity 99%) as an orange-yellow solid. MALDI-TOF-MS results: Molecular ion peak: 821.41. Elemental analysis results: Theoretical values: C, 86.24; H, 6.01; B, 2.63; N, 5.11; Experimental values: C, 86.27; H, 6.03; B, 2.60; N, 5.10.

[0194] Synthesis Example 25:

[0195] Synthesis of compound A-184

[0196]

[0197] Under a nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of a Br-substituted precursor (15 mmol) at 0 °C, and the mixture was then heated to 25 °C and reacted for 1 hour. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (60 mmol) was slowly added. The mixture was then heated to 60 °C and stirred for another 2 hours. N,N-diisopropylethylamine (120 mmol) was added at room temperature, and the reaction was continued at 130 °C for 12 hours. A tetrahydrofuran solution (60 mmol) of phenylmagnesium bromide was added at room temperature, and the reaction was stopped after 6 hours. The solvent was then evaporated under vacuum, and the solution was passed through a silica gel column (eluent: dichloromethane: petroleum ether = 1:10) to give the target compound A-184 (33% yield, HPLC purity 99%) as an orange-yellow solid. MALDI-TOF-MS results: Molecular ion peak: 821.41. Elemental analysis results: Theoretical values: C, 86.24; H, 6.01; B, 2.63; N, 5.11; Experimental values: C, 86.27; H, 6.00; B, 2.61; N, 5.12.

[0198] Synthesis Example 26:

[0199] Synthesis of compound A-185

[0200]

[0201] Under a nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of a Br-substituted precursor (15 mmol) at 0 °C, and the mixture was then heated to 25 °C and reacted for 1 hour. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (60 mmol) was slowly added. The mixture was then heated to 60 °C and stirred for another 2 hours. N,N-diisopropylethylamine (120 mmol) was added at room temperature, and the reaction was continued at 130 °C for 12 hours. A tetrahydrofuran solution (60 mmol) of phenylmagnesium bromide was added at room temperature, and the reaction was stopped after 6 hours. The solvent was then evaporated under vacuum, and the solution was passed through a silica gel column (eluent: dichloromethane: petroleum ether = 1:10) to give the target compound A-185 (32% yield, HPLC purity 99%) as an orange-yellow solid. MALDI-TOF-MS results: Molecular ion peak: 821.41. Elemental analysis results: Theoretical values: C, 86.24; H, 6.01; B, 2.63; N, 5.11; Experimental values: C, 86.27; H, 6.00; B, 2.60; N, 5.13.

[0202] Synthesis Example 27:

[0203] Synthesis of compound A-186

[0204]

[0205] Under a nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of a Br-substituted precursor (15 mmol) at 0 °C, and the mixture was then heated to 25 °C and reacted for 1 hour. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (60 mmol) was slowly added. The mixture was then heated to 60 °C and stirred for another 2 hours. N,N-diisopropylethylamine (120 mmol) was added at room temperature, and the reaction was continued at 130 °C for 12 hours. A tetrahydrofuran solution (60 mmol) of phenylmagnesium bromide was added at room temperature, and the reaction was stopped after 6 hours. The solvent was then evaporated under vacuum, and the solution was passed through a silica gel column (eluent: dichloromethane: petroleum ether = 1:10) to give the target compound A-186 (33% yield, HPLC purity 99%) as an orange-yellow solid. MALDI-TOF-MS results: Molecular ion peak: 821.41. Elemental analysis results: Theoretical values: C, 86.24; H, 6.01; B, 2.63; N, 5.11; Experimental values: C, 86.25; H, 6.01; B, 2.62; N, 5.12.

[0206] Synthesis Example 28:

[0207] Synthesis of compound B-4

[0208]

[0209] Under a nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of a Br-substituted precursor (15 mmol) at 0 °C, and the mixture was then heated to 25 °C and reacted for 1 hour. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (60 mmol) was slowly added. The mixture was then heated to 60 °C and stirred for another 2 hours. N,N-diisopropylethylamine (120 mmol) was added at room temperature, and the reaction was continued at 130 °C for 12 hours. A tetrahydrofuran solution (60 mmol) of phenylmagnesium bromide was added at room temperature, and the reaction was stopped after 6 hours. The solvent was then evaporated under vacuum, and the solution was passed through a silica gel column (eluent: dichloromethane: petroleum ether = 1:10) to give the target compound B-4 (36% yield, HPLC purity 99%) as an orange-yellow solid. MALDI-TOF-MS results: Molecular ion peak: 766.46. Elemental analysis results: Theoretical values: C, 86.16; H, 7.36; B, 2.82; N, 3.65; Experimental values: C, 86.17; H, 7.37; B, 2.81; N, 3.64.

[0210] Synthesis Example 29:

[0211] Synthesis of compound B-57

[0212]

[0213] Under a nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of a Br-substituted precursor (15 mmol) at 0 °C, and the mixture was then heated to 25 °C and reacted for 1 hour. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (60 mmol) was slowly added. The mixture was then heated to 60 °C and stirred for another 2 hours. N,N-diisopropylethylamine (120 mmol) was added at room temperature, and the reaction was continued at 130 °C for 12 hours. A tetrahydrofuran solution (60 mmol) of phenylmagnesium bromide was added at room temperature, and the reaction was stopped after 6 hours. The solvent was then evaporated under vacuum, and the solution was passed through a silica gel column (eluent: dichloromethane: petroleum ether = 1:10) to give the target compound B-57 (30% yield, HPLC purity 99%) as an orange-yellow solid. MALDI-TOF-MS results: Molecular ion peak: 707.27 Elemental analysis results: Theoretical values: C, 86.59; H, 4.42; B, 3.06; N, 5.94; Experimental values: C, 86.58; H, 4.40; B, 3.07; N, 5.95.

[0214] Synthesis Example 30:

[0215] Synthesis of compound C-4

[0216]

[0217] Under a nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of a Br-substituted precursor (15 mmol) at 0 °C, and the mixture was then heated to 25 °C and reacted for 1 hour. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (60 mmol) was slowly added. The mixture was then heated to 60 °C and stirred for another 2 hours. N,N-diisopropylethylamine (120 mmol) was added at room temperature, and the reaction was continued at 130 °C for 12 hours. A tetrahydrofuran solution (60 mmol) of phenylmagnesium bromide was added at room temperature, and the reaction was stopped after 6 hours. The solvent was then evaporated under vacuum, and the solution was passed through a silica gel column (eluent: dichloromethane: petroleum ether = 1:10) to give the target compound C-4 (36% yield, HPLC purity 99%) as an orange-yellow solid. MALDI-TOF-MS results: Molecular ion peak: 782.46. Elemental analysis results: Theoretical values: C, 84.40; H, 7.21; B, 2.76; N, 3.58; O, 2.04; Experimental values: C, 84.41; H, 7.22; B, 2.75; N, 3.58; O, 2.03.

[0218] Synthesis Example 31:

[0219] Synthesis of compound D-4

[0220]

[0221] Under a nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of a Br-substituted precursor (15 mmol) at 0 °C, and the mixture was then heated to 25 °C and reacted for 1 hour. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (60 mmol) was slowly added. The mixture was then heated to 60 °C and stirred for another 2 hours. N,N-diisopropylethylamine (120 mmol) was added at room temperature, and the reaction was continued at 130 °C for 12 hours. A tetrahydrofuran solution (60 mmol) of phenylmagnesium bromide was added at room temperature, and the reaction was stopped after 6 hours. The solvent was then evaporated under vacuum, and the solution was passed through a silica gel column (eluent: dichloromethane: petroleum ether = 1:10) to give the target compound D-4 (32% yield, HPLC purity 99%) as an orange-yellow solid. MALDI-TOF-MS results: Molecular ion peak: 798.44. Elemental analysis results: Theoretical values: C, 82.71; H, 7.07; B, 2.71; N, 3.51; S, 4.01; Experimental values: C, 82.73; H, 7.06; B, 2.70; N, 3.50; S, 4.02.

[0222] Synthesis Example 32:

[0223] Synthesis of compound E-4

[0224]

[0225] Under a nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of a Br-substituted precursor (15 mmol) at 0 °C, and the mixture was then heated to 25 °C and reacted for 1 hour. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (60 mmol) was slowly added. The mixture was then heated to 60 °C and stirred for another 2 hours. N,N-diisopropylethylamine (120 mmol) was added at room temperature, and the reaction was continued at 130 °C for 12 hours. A tetrahydrofuran solution (60 mmol) of phenylmagnesium bromide was added at room temperature, and the reaction was stopped after 6 hours. The solvent was then evaporated under vacuum, and the solution was passed through a silica gel column (eluent: dichloromethane: petroleum ether = 1:10) to give the target compound E-4 (33% yield, HPLC purity 99%) as an orange-yellow solid. MALDI-TOF-MS results: Molecular ion peak: 846.38. Elemental analysis results: Theoretical values: C, 78.12; H, 6.68; B, 2.56; N, 3.31; Se, 9.34; Experimental values: C, 78.11; H, 6.67; B, 2.55; N, 3.32; Se, 9.36.

[0226] Synthesis Example 33:

[0227] Synthesis of compound F-4

[0228]

[0229] Under a nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of a Br-substituted precursor (15 mmol) at 0 °C, and the mixture was then heated to 25 °C and reacted for 1 hour. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (60 mmol) was slowly added. The mixture was then heated to 60 °C and stirred for another 2 hours. N,N-diisopropylethylamine (120 mmol) was added at room temperature, and the reaction was continued at 130 °C for 12 hours. A tetrahydrofuran solution (60 mmol) of phenylmagnesium bromide was added at room temperature, and the reaction was stopped after 6 hours. The solvent was then evaporated under vacuum, and the solution was passed through a silica gel column (eluent: dichloromethane: petroleum ether = 1:10) to give the target compound F-4 (31% yield, HPLC purity 99%) as an orange-yellow solid. MALDI-TOF-MS results: Molecular ion peak: 857.51. Elemental analysis results: Theoretical values: C, 85.41; H, 7.17; B, 2.52; N, 4.90; Experimental values: C, 85.39; H, 7.18; B, 2.51; N, 4.92.

[0230] Synthesis Example 34:

[0231] Synthesis of compound G-4

[0232]

[0233] Under a nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of a Br-substituted precursor (15 mmol) at 0 °C, and the mixture was then heated to 25 °C and reacted for 1 hour. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (60 mmol) was slowly added. The mixture was then heated to 60 °C and stirred for another 2 hours. N,N-diisopropylethylamine (120 mmol) was added at room temperature, and the reaction was continued at 130 °C for 12 hours. A tetrahydrofuran solution (60 mmol) of phenylmagnesium bromide was added at room temperature, and the reaction was stopped after 6 hours. The solvent was then evaporated under vacuum, and the solution was passed through a silica gel column (eluent: dichloromethane: petroleum ether = 1:10) to give the target compound G-4 (37% yield, HPLC purity 99%) as an orange-yellow solid. MALDI-TOF-MS results: Molecular ion peak: 932.54. Elemental analysis results: Theoretical values: C, 87.55; H, 7.13; B, 2.32; N, 3.00; Experimental values: C, 87.55; H, 7.15; B, 2.31; N, 3.01.

[0234] Synthesis Example 35:

[0235] Synthesis of compound H-4

[0236]

[0237] Under a nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a tert-butylbenzene (150 mL) solution of a Br-substituted precursor (15 mmol) at 0 °C, and the mixture was then heated to 25 °C and reacted for 1 hour. After the reaction was complete, the temperature was lowered to -30 °C, and boron tribromide (60 mmol) was slowly added. The mixture was then heated to 60 °C and stirred for another 2 hours. N,N-diisopropylethylamine (120 mmol) was added at room temperature, and the reaction was continued at 130 °C for 12 hours. A tetrahydrofuran solution (60 mmol) of phenylmagnesium bromide was added at room temperature, and the reaction was stopped after 6 hours. The solvent was then evaporated under vacuum, and the solution was passed through a silica gel column (eluent: dichloromethane: petroleum ether = 1:10) to give the target compound H-4 (32% yield, HPLC purity 99%) as an orange-yellow solid. MALDI-TOF-MS results: Molecular ion peak: 948.52. Elemental analysis results: Theoretical values: C, 84.80; H, 7.01; B, 2.28; N, 2.95; Si, 2.96; Experimental values: C, 84.81; H, 7.00; B, 2.26; N, 2.96; Si, 2.97.

[0238] The photophysical properties of the representative fused-ring compounds prepared in the above-described synthetic examples of the present invention are shown in Table 1.

[0239] Table 1:

[0240]

[0241]

[0242]

[0243] Note: In Table 1, quantum efficiency is the ratio of the average number of photoelectrons generated per unit time to the number of incident photons at a specific wavelength. This is calculated by using compounds with a quantum efficiency of 10... -5 The sample was prepared by dissolving the compound in toluene at a concentration of mol / L, and then measured after deoxygenation under nitrogen. The instrument was an Edinburgh FLS1000 (UK). The half-width at half-maximum (WHM) is the width of the peak at half the peak height of the fluorescence spectrum at room temperature. It is calculated by drawing a straight line parallel to the base of the peak through the midpoint of the peak height, and finding the distance between the two points where this line intersects the peak. The fluorescence spectrum is obtained by measuring the compound at 10 mol / L concentrations. -5 The sample was prepared by dissolving it in toluene at a concentration of mol / L and then tested using a fluorescence spectrometer (Edinburg FLS1000 (UK)).

[0244] As can be seen from Table 1, the fused ring compounds in the embodiments provided by the present invention have high quantum efficiency (>85%), while the luminescent compounds provided by the present invention exhibit narrow half-width (<20nm).

[0245] The technical effects and advantages of the present invention will be demonstrated and verified by specifically applying the compounds of the present invention to organic electroluminescent devices and testing their actual performance.

[0246] An organic electroluminescent device includes a first electrode, a second electrode, and an organic material layer located between the two electrodes. This organic material layer can be further divided into multiple regions; for example, it may include a hole transport region, a light-emitting layer, and an electron transport region.

[0247] The anode material can be any combination of transparent conductive oxide materials such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), and zinc oxide (ZnO). The cathode material can be any combination of metals or alloys such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag).

[0248] The hole transport region is located between the anode and the light-emitting layer. The hole transport region can be a single-layer hole transport layer (HTL), including a single-layer hole transport layer containing only one compound and a single-layer hole transport layer containing multiple compounds. The hole transport region can also be a multilayer structure including at least one of a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL).

[0249] The material for the hole transport region can be selected from, but is not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylene oxide, polyaniline / dodecylbenzenesulfonic acid (Pani / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (Pani / CSA), polyaniline / poly(4-styrenesulfonate) (Pani / PSS), aromatic amine derivatives, etc.

[0250] The emissive layer includes luminescent dyes (i.e., dopants) that can emit different wavelengths of light, and may also include sensitizers and host materials. The emissive layer can be a monochromatic emissive layer emitting a single color such as red, green, or blue. Multiple monochromatic emissive layers of different colors can be arranged in a planar pattern according to pixel design, or they can be stacked together to form a colored emissive layer. When different colored emissive layers are stacked together, they can be separated from each other or connected to each other. The emissive layer can also be a single colored emissive layer that can simultaneously emit different colors such as red, green, and blue.

[0251] The electron transport region can be a single-layer electron transport layer (ETL), including a single-layer electron transport layer containing only one compound and a single-layer electron transport layer containing multiple compounds. The electron transport region can also be a multilayer structure including at least one of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0252] Specifically, the method for fabricating the organic electroluminescent device of the present invention includes the following steps:

[0253] 1. The glass plate coated with the anodic material is ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in a mixture of acetone and ethanol, baked in a clean environment until all moisture is removed, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam.

[0254] 2. Place the glass plate with the anode inside the vacuum chamber and evacuate to a vacuum level of 1×10⁻⁶. -5 ~8×10 -4 Pa, a hole injection layer is formed by vacuum evaporation of hole injection material on the above-mentioned anolyte film, with an evaporation rate of 0.1-0.5 nm / s;

[0255] 3. A hole transport layer is formed by vacuum evaporation of hole transport material on top of the hole injection layer, with an evaporation rate of 0.1-0.5 nm / s;

[0256] 4. An organic light-emitting layer of the device is vacuum-deposited on top of the hole transport layer. The organic light-emitting layer material includes a host material, a sensitizer, and a dye. The evaporation rate of the host material, the evaporation rate of the sensitizer material, and the evaporation rate of the dye are adjusted by using a multi-source co-evaporation method to make the dye reach a preset doping ratio.

[0257] 5. An electron transport layer is formed by vacuum evaporating the electron transport material of the device on top of the organic light-emitting layer, with an evaporation rate of 0.1-0.5 nm / s;

[0258] 6. On the electron transport layer, LiF is vacuum-deposited at 0.1-0.5 nm / s as the electron injection layer, and Al layer is vacuum-deposited at 0.5-1 nm / s as the cathode of the device.

[0259] This invention also provides a display device, which includes the organic electroluminescent device as described above. Specifically, the display device can be an OLED display or other display device, as well as any product or component with display function, such as a television, digital camera, mobile phone, or tablet computer, that includes the display device. The advantages of this display device over the prior art are the same as those of the organic electroluminescent device described above, and will not be repeated here.

[0260] The organic electroluminescent device of the present invention will be further described below through specific embodiments.

[0261] Device Example 1

[0262] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0263] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-1(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0264] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm (5 nm in this embodiment); the hole transport layer material is HT, with a total thickness of 5-500 nm (30 nm in this embodiment); the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, and A-1 is a dye with a doping concentration of 2 wt%. The thickness of the organic light-emitting layer is generally 1-200 nm (30 nm in this embodiment); the electron transport layer material is ET, with a thickness of 5-300 nm (30 nm in this embodiment); and the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0265] Device Example 2

[0266] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0267] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-4(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0268] In this embodiment, the anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm, and 5 nm in this embodiment; the hole transport layer material is HT, with a total thickness of 5-500 nm, and 30 nm in this embodiment; the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, and A-4 is a dye with a doping concentration of 2 wt%, with a thickness of 1-200 nm in this embodiment, and 30 nm in this embodiment; the electron transport layer material is ET, with a thickness of 5-300 nm, and 30 nm in this embodiment; the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0269] Device Example 3

[0270] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0271] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-8(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0272] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm (5 nm in this embodiment); the hole transport layer material is HT, with a total thickness of 5-500 nm (30 nm in this embodiment); the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, and A-8 is a dye with a doping concentration of 2 wt%. The thickness of the organic light-emitting layer is generally 1-200 nm (30 nm in this embodiment); the electron transport layer material is ET, with a thickness of 5-300 nm (30 nm in this embodiment); and the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0273] Device Example 4

[0274] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0275] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-10(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0276] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm, and 5 nm in this embodiment; the hole transport layer material is HT, with a total thickness of 5-500 nm, and 30 nm in this embodiment; the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, and A-10 is a dye with a doping concentration of 2 wt%, with a thickness of 1-200 nm, and 30 nm in this embodiment; the electron transport layer material is ET, with a thickness of 5-300 nm, and 30 nm in this embodiment; the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0277] Device Example 5

[0278] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0279] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-13(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0280] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm (5 nm in this embodiment); the hole transport layer material is HT, with a total thickness of 5-500 nm (30 nm in this embodiment); the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, and A-13 is a dye with a doping concentration of 2 wt%. The thickness of the organic light-emitting layer is generally 1-200 nm (30 nm in this embodiment); the electron transport layer material is ET, with a thickness of 5-300 nm (30 nm in this embodiment); and the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0281] Device Example 6

[0282] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0283] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-17(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0284] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm (5 nm in this embodiment); the hole transport layer material is HT, with a total thickness of 5-500 nm (30 nm in this embodiment); the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, and A-17 is a dye with a doping concentration of 2 wt%. The thickness of the organic light-emitting layer is generally 1-200 nm (30 nm in this embodiment); the electron transport layer material is ET, with a thickness of 5-300 nm (30 nm in this embodiment); and the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0285] Device Example 7

[0286] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0287] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-21(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0288] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm, and 5 nm in this embodiment; the hole transport layer material is HT, with a total thickness of 5-500 nm, and 30 nm in this embodiment; the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, and A-21 is a dye with a doping concentration of 2 wt%, with a thickness of 1-200 nm, and 30 nm in this embodiment; the electron transport layer material is ET, with a thickness of 5-300 nm, and 30 nm in this embodiment; the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0289] Device Example 8

[0290] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0291] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-24(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0292] In this embodiment, the anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm, and 5 nm in this embodiment; the hole transport layer material is HT, with a total thickness of 5-500 nm, and 30 nm in this embodiment; the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, and A-24 is a dye with a doping concentration of 2 wt%, with a thickness of 1-200 nm in this embodiment, and 30 nm in this embodiment; the electron transport layer material is ET, with a thickness of 5-300 nm, and 30 nm in this embodiment; the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0293] Device Example 9

[0294] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0295] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-44(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0296] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm, and 5 nm in this embodiment; the hole transport layer material is HT, with a total thickness of 5-500 nm, and 30 nm in this embodiment; the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, and A-44 is a dye with a doping concentration of 2 wt%, with a thickness of 1-200 nm, and 30 nm in this embodiment; the electron transport layer material is ET, with a thickness of 5-300 nm, and 30 nm in this embodiment; the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0297] Device Example 10

[0298] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0299] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-55(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0300] In this embodiment, the anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm, and 5 nm in this embodiment; the hole transport layer material is HT, with a total thickness of 5-500 nm, and 30 nm in this embodiment; the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, and A-55 is a dye with a doping concentration of 2 wt%, with a thickness of 1-200 nm in this embodiment, and 30 nm in this embodiment; the electron transport layer material is ET, with a thickness of 5-300 nm, and 30 nm in this embodiment; the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0301] Device Example 11

[0302] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0303] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-65(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0304] In this embodiment, the anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm, and 5 nm in this embodiment; the hole transport layer material is HT, with a total thickness of 5-500 nm, and 30 nm in this embodiment; the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, and A-65 is a dye with a doping concentration of 2 wt%, with a thickness of 1-200 nm in this embodiment, and 30 nm in this embodiment; the electron transport layer material is ET, with a thickness of 5-300 nm, and 30 nm in this embodiment; the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0305] Device Example 12

[0306] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0307] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-70(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0308] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm (5 nm in this embodiment); the hole transport layer material is HT, with a total thickness of 5-500 nm (30 nm in this embodiment); the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, and A-70 is a dye with a doping concentration of 2 wt%. The thickness of the organic light-emitting layer is generally 1-200 nm (30 nm in this embodiment); the electron transport layer material is ET, with a thickness of 5-300 nm (30 nm in this embodiment); and the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0309] Device Example 13

[0310] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0311] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-80(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0312] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm (5 nm in this embodiment); the hole transport layer material is HT, with a total thickness of 5-500 nm (30 nm in this embodiment); the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, and A-80 is a dye with a doping concentration of 2 wt%. The thickness of the organic light-emitting layer is generally 1-200 nm (30 nm in this embodiment); the electron transport layer material is ET, with a thickness of 5-300 nm (30 nm in this embodiment); and the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0313] Device Example 14

[0314] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0315] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-81(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0316] In this embodiment, the anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm, and 5 nm in this embodiment; the hole transport layer material is HT, with a total thickness of 5-500 nm, and 30 nm in this embodiment; the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, and A-81 is a dye with a doping concentration of 2 wt%, with a thickness of 1-200 nm in this embodiment, and 30 nm in this embodiment; the electron transport layer material is ET, with a thickness of 5-300 nm, and 30 nm in this embodiment; the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0317] Device Example 15

[0318] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0319] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-82(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0320] In this embodiment, the anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm, and 5 nm in this embodiment; the hole transport layer material is HT, with a total thickness of 5-500 nm, and 30 nm in this embodiment; the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, and A-82 is a dye with a doping concentration of 2 wt%, with a thickness of 1-200 nm in this embodiment, and 30 nm in this embodiment; the electron transport layer material is ET, with a thickness of 5-300 nm, and 30 nm in this embodiment; the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0321] Device Example 16

[0322] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0323] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-85(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0324] In this embodiment, the anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm, and 5 nm in this embodiment; the hole transport layer material is HT, with a total thickness of 5-500 nm, and 30 nm in this embodiment; the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, and A-85 is a dye with a doping concentration of 2 wt%, with a thickness of 1-200 nm in this embodiment, and 30 nm in this embodiment; the electron transport layer material is ET, with a thickness of 5-300 nm, and 30 nm in this embodiment; the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0325] Device Example 17

[0326] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0327] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-87(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0328] In this embodiment, the anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm, and 5 nm in this embodiment; the hole transport layer material is HT, with a total thickness of 5-500 nm, and 30 nm in this embodiment; the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, and A-87 is a dye with a doping concentration of 2 wt%, with a thickness of 1-200 nm in this embodiment, and 30 nm in this embodiment; the electron transport layer material is ET, with a thickness of 5-300 nm, and 30 nm in this embodiment; the electron injection layer and cathode materials are LiF (0.5 nm) and metallic aluminum (150 nm).

[0329] Device Example 18

[0330] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0331] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-94(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0332] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm, and 5 nm in this embodiment; the hole transport layer material is HT, with a total thickness of 5-500 nm, and 30 nm in this embodiment; the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, and A-94 is a dye with a doping concentration of 2 wt%, with a thickness of 1-200 nm, and 30 nm in this embodiment; the electron transport layer material is ET, with a thickness of 5-300 nm, and 30 nm in this embodiment; the electron injection layer and cathode materials are LiF (0.5 nm) and metallic aluminum (150 nm).

[0333] Device Example 19

[0334] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0335] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-155(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0336] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm (5 nm in this embodiment); the hole transport layer material is HT, with a total thickness of 5-500 nm (30 nm in this embodiment); the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, and A-155 is a dye with a doping concentration of 2 wt%. The thickness of the organic light-emitting layer is generally 1-200 nm (30 nm in this embodiment); the electron transport layer material is ET, with a thickness of 5-300 nm (30 nm in this embodiment); and the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0337] Device Example 20

[0338] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0339] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-179(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0340] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm (5 nm in this embodiment); the hole transport layer material is HT, with a total thickness of 5-500 nm (30 nm in this embodiment); the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, and A-179 is a dye with a doping concentration of 2 wt%. The thickness of the organic light-emitting layer is generally 1-200 nm (30 nm in this embodiment); the electron transport layer material is ET, with a thickness of 5-300 nm (30 nm in this embodiment); and the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0341] Device Example 21

[0342] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0343] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-180(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0344] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm (5 nm in this embodiment); the hole transport layer material is HT, with a total thickness of 5-500 nm (30 nm in this embodiment); the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, and A-180 is a dye with a doping concentration of 2 wt%. The thickness of the organic light-emitting layer is generally 1-200 nm (30 nm in this embodiment); the electron transport layer material is ET, with a thickness of 5-300 nm (30 nm in this embodiment); and the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0345] Device Example 22

[0346] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0347] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-181(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0348] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm, and 5 nm in this embodiment; the hole transport layer material is HT, with a total thickness of 5-500 nm, and 30 nm in this embodiment; the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, A-181 is a dye with a doping concentration of 2 wt%, and the thickness of the organic light-emitting layer is generally 1-200 nm, and 30 nm in this embodiment; the electron transport layer material is ET, with a thickness of 5-300 nm, and 30 nm in this embodiment; the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0349] Device Example 23

[0350] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0351] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-182(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0352] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm (5 nm in this embodiment); the hole transport layer material is HT, with a total thickness of 5-500 nm (30 nm in this embodiment); the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, and A-182 is a dye with a doping concentration of 2 wt%. The thickness of the organic light-emitting layer is generally 1-200 nm (30 nm in this embodiment); the electron transport layer material is ET, with a thickness of 5-300 nm (30 nm in this embodiment); and the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0353] Device Example 24

[0354] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0355] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-183(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0356] In this embodiment, the anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm, and 5 nm in this embodiment; the hole transport layer material is HT, with a total thickness of 5-500 nm, and 30 nm in this embodiment; the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, and A-183 is a dye with a doping concentration of 2 wt%, with a thickness of 1-200 nm in this embodiment, and 30 nm in this embodiment; the electron transport layer material is ET, with a thickness of 5-300 nm, and 30 nm in this embodiment; the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0357] Device Example 25

[0358] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0359] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-184(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0360] In this embodiment, the anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm, and 5 nm in this embodiment; the hole transport layer material is HT, with a total thickness of 5-500 nm, and 30 nm in this embodiment; the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, and A-184 is a dye with a doping concentration of 2 wt%, with a thickness of 1-200 nm in this embodiment, and 30 nm in this embodiment; the electron transport layer material is ET, with a thickness of 5-300 nm, and 30 nm in this embodiment; the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0361] Device Example 26

[0362] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0363] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-185(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0364] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm (5 nm in this embodiment); the hole transport layer material is HT, with a total thickness of 5-500 nm (30 nm in this embodiment); the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, and A-185 is a dye with a doping concentration of 2 wt%. The thickness of the organic light-emitting layer is generally 1-200 nm (30 nm in this embodiment); the electron transport layer material is ET, with a thickness of 5-300 nm (30 nm in this embodiment); and the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0365] Device Example 27

[0366] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0367] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%A-186(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0368] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm (5 nm in this embodiment); the hole transport layer material is HT, with a total thickness of 5-500 nm (30 nm in this embodiment); the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, and A-186 is a dye with a doping concentration of 2 wt%. The thickness of the organic light-emitting layer is generally 1-200 nm (30 nm in this embodiment); the electron transport layer material is ET, with a thickness of 5-300 nm (30 nm in this embodiment); and the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0369] Device Example 28

[0370] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0371] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%B-4(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0372] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm, and 5 nm in this embodiment; the hole transport layer material is HT, with a total thickness of 5-500 nm, and 30 nm in this embodiment; the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, B-4 is a dye with a doping concentration of 2 wt%, and the thickness of the organic light-emitting layer is generally 1-200 nm, and 30 nm in this embodiment; the electron transport layer material is ET, with a thickness of 5-300 nm, and 30 nm in this embodiment; the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0373] Device Example 29

[0374] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0375] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%B-57(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0376] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm (5 nm in this embodiment); the hole transport layer material is HT, with a total thickness of 5-500 nm (30 nm in this embodiment); the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, B-57 is a dye with a doping concentration of 2 wt%, and the thickness of the organic light-emitting layer is generally 1-200 nm (30 nm in this embodiment); the electron transport layer material is ET, with a thickness of 5-300 nm (30 nm in this embodiment); the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0377] Device Example 30

[0378] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0379] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%C-4(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0380] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm (5 nm in this embodiment); the hole transport layer material is HT, with a total thickness of 5-500 nm (30 nm in this embodiment); the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, C-4 is a dye with a doping concentration of 2 wt%, and the thickness of the organic light-emitting layer is generally 1-200 nm (30 nm in this embodiment); the electron transport layer material is ET, with a thickness of 5-300 nm (30 nm in this embodiment); the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0381] Device Example 31

[0382] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0383] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%D-4(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0384] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm (5 nm in this embodiment); the hole transport layer material is HT, with a total thickness of 5-500 nm (30 nm in this embodiment); the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, D-4 is a dye with a doping concentration of 2 wt%, and the thickness of the organic light-emitting layer is generally 1-200 nm (30 nm in this embodiment); the electron transport layer material is ET, with a thickness of 5-300 nm (30 nm in this embodiment); the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0385] Device Example 32

[0386] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0387] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%E-4(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0388] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm, and 5 nm in this embodiment; the hole transport layer material is HT, with a total thickness of 5-500 nm, and 30 nm in this embodiment; the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is the sensitizer with a doping concentration of 20 wt%, E-4 is the dye with a doping concentration of 2 wt%, and the thickness of the organic light-emitting layer is generally 1-200 nm, and 30 nm in this embodiment; the electron transport layer material is ET, with a thickness of 5-300 nm, and 30 nm in this embodiment; the electron injection layer and cathode materials are LiF (0.5 nm) and metallic aluminum (150 nm).

[0389] Device Example 33

[0390] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0391] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%F-4(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0392] In this embodiment, the anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm, and 5 nm in this embodiment; the hole transport layer material is HT, with a total thickness of 5-500 nm, and 30 nm in this embodiment; the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, F-4 is a dye with a doping concentration of 2 wt%, and the thickness of the organic light-emitting layer is generally 1-200 nm, and 30 nm in this embodiment; the electron transport layer material is ET, with a thickness of 5-300 nm, and 30 nm in this embodiment; the electron injection layer and cathode materials are LiF (0.5 nm) and metallic aluminum (150 nm).

[0393] Device Example 34

[0394] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0395] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%G-4(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0396] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm (5 nm in this embodiment); the hole transport layer material is HT, with a total thickness of 5-500 nm (30 nm in this embodiment); the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, G-4 is a dye with a doping concentration of 2 wt%, and the thickness of the organic light-emitting layer is generally 1-200 nm (30 nm in this embodiment); the electron transport layer material is ET, with a thickness of 5-300 nm (30 nm in this embodiment); the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0397] Device Example 35

[0398] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0399] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%H-4(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0400] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm, and 5 nm in this embodiment; the hole transport layer material is HT, with a total thickness of 5-500 nm, and 30 nm in this embodiment; the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, H-4 is a dye with a doping concentration of 2 wt%, and the thickness of the organic light-emitting layer is generally 1-200 nm, and 30 nm in this embodiment; the electron transport layer material is ET, with a thickness of 5-300 nm, and 30 nm in this embodiment; the electron injection layer and cathode materials are LiF (0.5 nm) and metallic aluminum (150 nm).

[0401] Comparative Device Example 1

[0402] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0403] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%C1(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0404] In this embodiment, the anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm, and 5 nm in this embodiment; the hole transport layer material is HT, with a total thickness of 5-500 nm, and 30 nm in this embodiment; the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, and Cl is a dye with a doping concentration of 2 wt%, with a thickness of 1-200 nm in this embodiment, and 30 nm in this embodiment; the electron transport layer material is ET, with a thickness of 5-300 nm, and 30 nm in this embodiment; the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0405] Comparative Device Example 2

[0406] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0407] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%C2(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0408] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm, and 5 nm in this embodiment; the hole transport layer material is HT, with a total thickness of 5-500 nm, and 30 nm in this embodiment; the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, C2 is a dye with a doping concentration of 2 wt%, and the thickness of the organic light-emitting layer is generally 1-200 nm, and 30 nm in this embodiment; the electron transport layer material is ET, with a thickness of 5-300 nm, and 30 nm in this embodiment; the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0409] Comparative Device Example 3

[0410] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0411] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%C3(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0412] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm, and 5 nm in this embodiment; the hole transport layer material is HT, with a total thickness of 5-500 nm, and 30 nm in this embodiment; the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, C3 is a dye with a doping concentration of 2 wt%, and the thickness of the organic light-emitting layer is generally 1-200 nm, and 30 nm in this embodiment; the electron transport layer material is ET, with a thickness of 5-300 nm, and 30 nm in this embodiment; the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0413] Comparative Device Example 4

[0414] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0415] ITO / HI(5nm) / HT(30nm) / Host:20wt%Sensitizer:2wt%C4(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0416] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm (5 nm in this embodiment); the hole transport layer material is HT, with a total thickness of 5-500 nm (30 nm in this embodiment); the host is the main material of the wide bandgap organic light-emitting layer, the sensitizer is a sensitizer with a doping concentration of 20 wt%, C4 is a dye with a doping concentration of 2 wt%, and the thickness of the organic light-emitting layer is generally 1-200 nm (30 nm in this embodiment); the electron transport layer material is ET, with a thickness of 5-300 nm (30 nm in this embodiment); the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0417] The structural formulas of the various organic materials used in the above embodiments are as follows:

[0418]

[0419]

[0420]

[0421] The C1-C4 compounds mentioned above as comparative compounds are compounds in the prior art. Their synthesis methods can be found in patent applications CN107851724, CN108431984, CN110407858, CN110776509, etc., and will not be repeated here.

[0422] The performance of the organic electroluminescent devices prepared in the above embodiments and comparative examples is shown in Table 2 below.

[0423] Table 2:

[0424]

[0425]

[0426]

[0427] With respect to Examples 1-35 and Comparative Examples 1-4, assuming other materials remain the same in the organic electroluminescent device structure, the compounds of this invention exhibit a narrower electroluminescence spectrum. Furthermore, compared to the multiple resonance TADF dyes with nitrogen-boron-nitrogen structures in the comparative examples, the devices prepared with the compounds provided by this invention have higher external quantum efficiency and longer lifetime. This is because the compounds of this invention, by introducing newly added boron atoms to lock the donor on one side, form a planar rigid framework structure with the central benzene ring, which reduces the relaxation degree of the excited state structure, thereby enabling the target molecule to possess both high luminescence efficiency, narrow spectral emission, and high stability.

[0428] The experimental data above show that the organic material of the present invention, as the light-emitting object of organic electroluminescent devices, is a high-performance organic light-emitting functional material and is expected to be promoted for commercial application.

[0429] Although the invention has been described in conjunction with embodiments, the invention is not limited to the above embodiments. It should be understood that various modifications and improvements can be made by those skilled in the art under the guidance of the inventive concept, and the appended claims summarize the scope of the invention.

[0430] Obviously, the above embodiments are merely examples for clear illustration and are not intended to limit the implementation. Those skilled in the art will recognize that other variations or modifications can be made based on the above description, and any obvious variations or modifications derived therefrom are still within the scope of protection of this invention.

Claims

1. An organic compound having a structure as shown in formula (1) : wherein: each of ring Ar 1, ring Ar 2, ring Ar 3, ring Ar 4 and ring Ar 5 is independently selected from a benzene ring, a naphthalene ring or a carbazolyl group; ring Ar 3 and ring Ar 4 are connected by a C-C single bond, O, S, Se or CR 7R 8; ring Ar 1 and ring Ar 2 are connected by a C-C single bond, O, S, Se or CR 7R 8; W is C or CH; each of R 1, R 2, R 3, R 4, R 5 and R 6 is independently selected from one of hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C 1-C 30 chain alkyl group, a substituted or unsubstituted C 3-C 20 cyclic alkyl group, a substituted or unsubstituted C 7-C 30 aralkyl group, a substituted or unsubstituted C 1-C 30 alkoxy group, a substituted or unsubstituted C 2-C 30 aliphatic chain amine group, a substituted or unsubstituted C 4-C 30 cyclic aliphatic chain amine group, a substituted or unsubstituted C 6-C 30 aryl amine group, a substituted or unsubstituted C 3-C 30 heteroaryl amine group, a substituted or unsubstituted C 6-C 30 aryloxy group, a substituted or unsubstituted C 6-C 60 aryl boron group, a substituted or unsubstituted C 6-C 60 aryl group, and a substituted or unsubstituted C 3-C 60 heteroaryl group; each of n 1, n 2, n 3, n 4 and n 5 is independently selected from an integer of 1-5; when each of n 1, n 2, n 3, n 4 and n 5 is an integer greater than 1, each of the corresponding multiple R 1, multiple R 2, multiple R 3, multiple R 4 and multiple R 5 is the same or different, and the multiple R 1 is not connected or connected into a ring, the multiple R 2 is not connected or connected into a ring, the multiple R 3 is not connected or connected into a ring, the multiple R 4 is not connected or connected into a ring, and the multiple R 5 is not connected or connected into a ring. 3.The organic compound according to claim 1 or 2, having a structure as shown in any one of the following formulae (1-2), (1-3), (1-4), (1-5), (1-6), (1-7) or (1-8) : (1-2) (1-3) (1-4) (1-5) (1-6) (1-7) (1-8) 4.The organic compound according to claim 1, wherein each of the ring Ar 1, ring Ar 2, ring Ar 3, ring Ar 4 and ring Ar 5 is independently a benzene ring. 5.The organic compound according to any one of claims 1-4, wherein each of R 1, R 2, R 3, R 4, R 5 and R 6 is independently one of a methyl group, an ethyl group, a n-propyl group, an i-propyl group, a n-butyl group, an i-butyl group, a sec-butyl group, a t-butyl group, a trifluoromethyl group, a pentafluoroethyl group, a cyano group, a halogen, a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, a spirobifluorenyl group, a carbazolyl group, a 1, 3, 5-triazinyl group, a diphenyl boron group, a dimethyl boron group, a dipentafluorophenyl boron group, a di (2, 4, 6-triisopropylphenyl) boron group, or a combination of two of the above groups. 6.An organic compound selected from the following specific structural compounds: ​ X1is a single bond, O, S, Se, CR 11 R 12 , Si R 13 R 14 or NR 15 ; m is 0 or 1 ; ​ ​ ​ R7, R8are each independently selected from one of C1-C4 chain alkyl, benzene ring; R 11 , R 12 , R 13 , R 14 and R 15 are each independently selected from one of C1-C4 chain alkyl, benzene ring; When the above R1, R2, R3, R4, R5, R6, R7, R8, R 11 , R 12 , R 13 , R 14 and R 15 each independently have a substituent, the substituent is each independently selected from one or a combination of two of halogen, cyano, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C10 alkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C6-C30 aryl, substituted or unsubstituted C6-C60 arylboron, C3-C30 heteroaryl.

2. The organic compound according to claim 1, in formula (1), each of R7, R8 is independently a phenyl ring; each of R 11 , R 12 , R 13 , R 14 and R 15 is independently a phenyl ring. ​ wherein R1-R6, R 11 -R 15 , Ar1-Ar5 and n1-n5 are each defined as in formula (1). ​ ​ ​ 7. Use of a compound according to any one of claims 1 to 6 as a functional material in an organic electronic device, including an organic electroluminescent device, an optical sensor, a solar cell, a lighting element, an organic thin-film transistor, an organic field-effect transistor, an information tag, an electronic artificial skin sheet, a sheet-type scanner or an electronic paper; the compound is used as a light-emitting layer material in an organic electroluminescent device.

8. An organic electroluminescent device comprising a first electrode, a second electrode and one or more light-emitting functional layers interposed between the first and second electrodes, wherein the light-emitting functional layers contain a compound according to any one of claims 1 to 6.

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