A light-emitting material, applications thereof, and an organic electroluminescent device comprising the same

Abstract

The present application relates to the technical field of organic electroluminescence, in particular to an organic compound and application thereof, and an organic electroluminescence device containing the compound. The compound has the structure shown in formula (1) as follows, wherein X 1 and X 2 are independently NR1, O, S or Se, ring A and ring B are independently selected from one of substituted or unsubstituted C6-C60 aromatic ring, substituted or unsubstituted C3-C60 heteroaromatic ring, R 12 , R 13 are independently selected from cyano, benzonitrile, halogen-substituted C1-C20 straight chain or branched alkyl, substituted or unsubstituted nitrogen-containing heteroaryl and other electron-withdrawing groups. The OLED device prepared by using the compound has low starting voltage, high luminous efficiency and better service life.

Description

Technical Field

[0001] This invention relates to the field of organic electroluminescence technology, and in particular to a novel organic compound and its applications, as well as an organic electroluminescence device containing the compound. Background Technology

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

[0003] As OLED technology continues to advance in both lighting and display fields, research into its core materials is receiving increasing attention. This is because a high-efficiency, long-life OLED device is typically the result of an optimized combination of device structure and various organic materials. This presents chemists with both significant opportunities and challenges in designing and developing functionalized materials with diverse structures. Common functionalized organic materials include: hole injection materials, hole transport materials, hole blocking materials, electron injection materials, electron transport materials, electron blocking materials, as well as luminescent host materials and luminescent guest materials (dyes), etc.

[0004] To fabricate OLED devices with lower driving voltages, better luminous efficiency, and longer lifespans, and to continuously improve the performance of OLED devices, it is necessary not only to innovate the structure and fabrication process of OLED devices, but also to continuously research and innovate the optoelectronic functional materials in OLED devices to prepare functional materials with higher performance. Based on this, the OLED materials community has been committed to developing new organic electroluminescent materials to achieve devices with low start-up voltages, high luminous efficiency, and better lifespans.

[0005] MR-TADF materials possess advantages such as high color purity and high luminous efficiency, attracting widespread attention from the scientific and industrial communities. However, due to their intrinsically long delayed fluorescence lifetime, their electroluminescent devices suffer from severe efficiency roll-off and poor stability, significantly limiting the further application of MR-TADF materials in high-resolution displays, full-color displays, and white light illumination. Summary of the Invention

[0006] To solve the above-mentioned technical problems, the present invention provides an organic compound, the specific general formula of which is shown in formula (1) below:

[0007]

[0008] In formula (1): X 1 and X 2 Each R1 is independently NR1, O, S or Se, and each R1 is independently connected to an adjacent ring A or ring B to form a ring or not connected to a ring. When connected to a ring, it is bonded to an adjacent benzene ring through -O-, -S-, -CR2R3- or a single bond.

[0009] R1 is selected from substituted or unsubstituted C6-C30 aryl groups, and R2 and R3 are each independently selected from one of substituted or unsubstituted C1-C10 alkyl groups, substituted or unsubstituted C6-C30 aryl groups, and substituted or unsubstituted C5-C30 heteroaryl groups.

[0010] Ring A and ring B are each independently selected from one of substituted or unsubstituted C6-C60 aromatic rings or substituted or unsubstituted C3-C60 heteroaromatic rings;

[0011] The substituents in ring A and ring B are each independently selected from deuterium, halogen, cyano, nitro, hydroxyl, amino, unsubstituted or R'-substituted C2-C10 alkenyl, unsubstituted or R'-substituted C1-C20 straight-chain or branched alkyl, unsubstituted or R'-substituted C3-C20 cycloalkyl, unsubstituted or R'-substituted C1-C20 alkoxy, unsubstituted or R'-substituted C1-C20 alkylsilyl, unsubstituted or R'-substituted C1-C20 alkylamino, unsubstituted or R'-substituted C6-C30 arylamino, unsubstituted or R'-substituted C3-C30 heteroarylamino, and unsubstituted or R'-substituted C6-C The R' is selected from one of the following: 30 aryloxy, unsubstituted or R'-substituted C3-C30 heteroaryloxy, unsubstituted or R'-substituted C6-C60 aryl, or unsubstituted or R'-substituted C3-C60 heteroaryl, wherein the R' is selected from one of the following: halogen, cyano, C2-C10 alkenyl, C1-C20 straight-chain or branched alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl.

[0012] R 12 R 13 Each group is independently selected from one of the following: hydrogen, cyano, benzonitrile, halogen-substituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted nitrogen-containing heteroaryl, or substituted or unsubstituted groups, and R12 R 13 Not both hydrogen:

[0013]

[0014] R 11 It is selected from one of hydrogen, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, and substituted or unsubstituted C6-C60 aryl;

[0015] The R1, R2, R3, R 11 R 12 R 13 The substituents described herein are each independently selected from one of halogens, C1-C10 straight-chain or branched alkyl groups, C3-C10 cycloalkyl groups, and C6-C30 aryl groups.

[0016] Furthermore, in the general formula of the present invention, ring A and ring B each independently have the structure shown in formula (a):

[0017]

[0018] In equation (a), Y 11 Y 12 Y 13 Y 14 Each R4 is independently selected from CR4 or N, and each R4 is independently selected from hydrogen, deuterium, halogen, cyano, unsubstituted or R'-substituted C1-C20 straight-chain or branched alkyl, unsubstituted or R'-substituted C3-C20 cycloalkyl, unsubstituted or R'-substituted C1-C20 alkoxy, unsubstituted or R'-substituted C1-C20 alkylamino, unsubstituted or R'-substituted C6-C30 arylamino, unsubstituted or R'-substituted C3-C30 heteroarylamino, unsubstituted or R'-substituted C6-C30 aryloxy, unsubstituted or R'-substituted C3 -C30 heteroaryloxy, unsubstituted or R'-substituted C6-C60 aryl, unsubstituted or R'-substituted C3-C60 heteroaryl, wherein R' is selected from halogen, cyano, C1-C20 straight-chain or branched alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl.

[0019] Furthermore, in the general formula of the present invention, when the X 1 and X 2When R1 is independently NR1, R1 is selected from substituted or unsubstituted phenyl groups; and when R1 is independently cyclically bonded to adjacent ring A or ring B via a -CR2R3- bond, R2 and R3 are independently methyl or phenyl groups. Further, in the general formula of the present invention,

[0020] Furthermore, in the general formula of the present invention, the Y 11 Y 12 Y 13 Y 14 Each of the R4 groups is independently selected from CR4, and each of the R4 groups is independently selected from one or a combination of two of the following: hydrogen, deuterium, halogen, cyano, C1-C20 straight-chain or branched alkyl, C6-C60 aryl, and C3-C60 heteroaryl.

[0021] More preferably, R4 is independently selected from hydrogen, deuterium, 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, pyrene, peryl, fluoranyl, tetraphenyl, pentaphenyl, benzo[a]pyrene, biphenyl, amphylphenyl, terphenyl, triphenyl, tetraphenyl, fluorene, spirodifluorene, dihydrogen phenanthrene, 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, naphzimidazoleyl, phenanthrenemidazoleyl, pyridiniumimazoleyl, pyraziniumimazoleyl, quin Oxalinimidazolyl, oxazolyl, benzoxoxazolyl, naphthoxazolyl, 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, benzocarbalinyl, phenanthrolinel, 1,2,3-triazolyl, 1,2,4-triazolyl, benzoxazolyl The following are selected from the following groups: triazolyl, 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, indazinyl, benzothiadiazolyl, 9,9-dimethylacridyl, halobenzene, cyanobenzene, trifluoromethylbenzene, etc., or combinations thereof;

[0022] More preferably, each of the R4 groups is independently selected from hydrogen, methyl, tert-butyl, phenyl, and pyridyl.

[0023] Furthermore, in the general formula of the present invention, the R 12 R 13Each group is independently selected from one of the following groups: hydrogen, cyano, benzonitrile, halogen-substituted C1-C5 straight-chain alkyl, substituted or unsubstituted pyridyl, substituted or unsubstituted triazine, or substituted or unsubstituted of the following groups, and R 12 R 13 Not both hydrogen:

[0024]

[0025] More preferably, the R 12 R 13 Each group is independently selected from hydrogen, cyano, benzonitrile, trifluoromethyl, or one of the following groups:

[0026]

[0027] Furthermore, in the general formula of the present invention, when the R 12 R 13 When both are selected from pyridyl or both are selected from phenyl-substituted triazine, R 11 It is hydrogen or related to R 12 R 13 same;

[0028] When the R 12 With R 13 When one of the groups is selected from the following groups, the other is hydrogen, and R 11 For hydrogen:

[0029]

[0030] In this invention, the "substituted or unsubstituted" group can replace one substituent or multiple substituents. When there are multiple substituents, they can be selected from different substituents. In this invention, when the same expression is used, they all have the same meaning, and the selection range of substituents is as shown above and will not be repeated one by one.

[0031] 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.

[0032] In this specification, the way a ring structure is represented by "—" indicates that the connection point is located at any position on the ring structure where bonding can occur.

[0033] In this specification, "each independently" means that when there are multiple subjects, they may be the same or different from each other.

[0034] In this invention, unless otherwise specified, the description of chemical elements generally includes the concept of their isotopes. For example, the description of "hydrogen (H)" includes its isotopes. 1H (protium or H), 2 The concept of H (deuterium or D); carbon (C) includes... 12 C 13 C, etc., will not be elaborated further.

[0035] In this invention, heteroatoms generally refer to atoms or groups of atoms selected from N, O, S, P, Si and Se, preferably selected from N, O and S.

[0036] Examples of halogens in this specification include fluorine, chlorine, bromine, and iodine.

[0037] In this invention, unless otherwise specified, aryl and heteroaryl groups include both monocyclic and fused-ring types.

[0038] In this invention, the substituted or unsubstituted C6-C60 aryl groups include monocyclic aryl groups and fused-ring aryl groups, preferably C6-C30 aryl groups, and more preferably C6-C20 aryl groups. A monocyclic aryl group refers to a molecule containing at least one phenyl group. When a molecule contains at least two phenyl groups, the phenyl groups are independent of each other and connected by a single bond, exemplarily such as phenyl, biphenyl, and terphenyl. Specifically, the biphenyl group includes 2-biphenyl, 3-biphenyl, and 4-biphenyl; the terphenyl group includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, meta-terphenyl-4-yl, meta-terphenyl-3-yl, and meta-terphenyl-2-yl. A fused-ring aryl group refers to a molecule containing at least two aromatic rings, where the aromatic rings are not independent of each other but share two adjacent carbon atoms fused together. Examples include: naphthyl, anthracene, phenanthrene, indene, fluorenyl, fluoranthyl, triphenylene, pyrene, perylene, etc. Naphthyl, 2-naphthyl, and their derivative groups, etc. The naphthyl includes 1-naphthyl or 2-naphthyl; the anthraceneyl is selected from 1-anthrayl, 2-anthrayl, and 9-anthrayl; the fluorenyl is selected from 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, and 9-fluorenyl; the pyrene is selected from 1-pyrene, 2-pyrene, and 4-pyrene; the 2-tetraphenyl is selected from 1-2 ... The fluorene derivative group is selected from 9,9-dimethylfluorenyl, 9,9-diethylfluorenyl, 9,9-dipropylfluorenyl, 9,9-dibutylfluorenyl, 9,9-dipentylfluorenyl, 9,9-dihexylfluorenyl, 9,9-diphenylfluorenyl, 9,9-dinaphthylfluorenyl, 9,9'-spirodifluorenyl, and benzo[a]fluorenyl.

[0039] The C3-C60 heteroaryl groups mentioned in this invention include monocyclic heteroaryl groups and fused-ring heteroaryl groups, preferably C3-C30 heteroaryl groups, more preferably C4-C20 heteroaryl groups, and even more preferably C5-C12 heteroaryl groups. A monocyclic heteroaryl group refers to a molecule containing at least one heteroaryl group. When a molecule contains one heteroaryl group and other groups (such as aryl, heteroaryl, alkyl, etc.), the heteroaryl group and the other groups are independent of each other and connected by a single bond. Examples of monocyclic heteroaryl groups include furanyl, thiophene, pyrrole, and pyridinyl. A fused-ring heteroaryl group refers to a molecule containing at least one aromatic heterocycle and an aromatic ring (aromatic heterocycle or aromatic ring), and the two are not independent of each other but share a group consisting of two adjacent atoms fused together. Examples of fused-ring heteroaryl groups include: benzofuranyl, benzothiophenyl, isobenzofuranyl, indolyl, dibenzofuranyl, dibenzothiophenyl, carbazoyl, acridineyl, isobenzofuranyl, isobenzothiophenyl, benzocarbazoyl, azircarbazoyl, phenothiazinyl, phenothiazinyl, 9-phenylcarbazoyl, 9-naphthylcarbazoyl, dibenzocarbazoyl, indolocarbazoyl, etc.

[0040] Specific examples of arylene groups in this invention can be exemplified by removing one hydrogen atom from the aforementioned aryl examples to obtain a divalent group. The number of carbon atoms in arylene groups includes, but is not limited to, C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, and C28. Specific examples of heteroarylene groups in this invention can be exemplified by removing one hydrogen atom from the aforementioned heteroaryl examples to obtain a divalent group.

[0041] The aryl group in this invention can be exemplified by the monovalent group composed of the above-mentioned aryl and heteroaryl groups and oxygen.

[0042] In this invention, arylamino represents a group formed by replacing the hydrogen on an amino group with one or two aryl groups, wherein the linking site of the arylamino can be linked to the aryl group in the arylamino or to the N group in the arylamino, and the exemplary number of carbons and specific groups of the aryl group in the arylamino are the same as described above.

[0043] Examples of C6-C30 arylamino groups mentioned in this invention include phenylamino, methylphenylamino, naphthylamino, anthraceneylamino, phenanthreneamino, and biphenylamino.

[0044] Examples of C3-C30 heteroaryl amino groups mentioned in this invention include pyridinyl amino, pyrimidinyl amino, and dibenzofuranyl amino.

[0045] Unless otherwise specified, the chain alkyl groups mentioned in this invention include straight-chain alkyl groups and branched-chain alkyl groups. Specifically, substituted or unsubstituted C1-C30 chain alkyl groups are preferably substituted or unsubstituted C1-C16 chain alkyl groups, and more preferably substituted or unsubstituted C1-C10 chain alkyl groups. Examples of substituted or unsubstituted C1-C10 chain alkyl groups include: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, neopentyl, n-hexyl, neohexyl, n-heptyl, n-octyl, 2-ethylhexyl, etc.

[0046] In this invention, the cycloalkyl group includes monocycloalkyl and polycycloalkyl; wherein, monocycloalkyl refers to an alkyl group containing a single ring structure; polycycloalkyl refers to a structure composed of two or more cycloalkyl groups sharing one or more carbon atoms on a ring; examples of C3-C20 cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, etc.

[0047] In this specification, the substituted or unsubstituted C1-C20 alkoxy group is preferably a substituted or unsubstituted C1-C10 alkoxy group. Examples of C1-C10 alkoxy groups include: methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, pentooxy, isopentoxy, hexoxy, heptoxy, octoxy, nonoxy, decoxy, undecoxy, dodecoxy, etc., among which methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy, sec-butoxy, isobutoxy, isopentoxy, and isopentoxy are preferred, and methoxy is more preferred.

[0048] In this specification, the substituted or unsubstituted C1-C20 silanes and the substituted or unsubstituted C1-C10 silanes are examples of silanes substituted with groups listed in the above C1-C10 silanes, specifically including: methylsilane, dimethylsilane, trimethylsilane, ethylsilane, diethylsilane, triethylsilane, tert-butyldimethylsilane, tert-butyldiphenylsilane, etc.

[0049] It should be noted that while the possible effects of each group / feature have been described separately for ease of explanation in this application, this does not mean that these groups / features act in isolation. In fact, the reason for achieving good performance is essentially the optimized combination of the entire molecule, the result of the synergistic effect between various groups, rather than the effect of a single group.

[0050] Furthermore, the compounds of general formula (1) of the present invention can preferably be the following specific structural compounds: M1-M1038, these compounds are only representative:

[0051]

[0052]

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[0100] The present invention also provides an organic electroluminescent device, comprising 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 comprises a compound shown in the above general formula.

[0101] Specifically, embodiments of the present invention provide 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, preferably, the light-emitting layer contains a compound of the general formula of the present invention shown above.

[0102] 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.

[0103] The specific reasons for the excellent performance of the compounds of the present invention as light-emitting layer materials in organic electroluminescent devices are not yet clear, but it is speculated that the reasons may be as follows:

[0104] In the general formula compounds of this invention, electron-withdrawing groups such as cyano, benzonitrile, trifluoromethyl, pyridine, and triazine are designed at the nitrogen atom para position of the central benzene ring in BN-type multiple resonance materials. Electron-withdrawing groups selected from the following specific structures are also designed:

[0105]

[0106] Introducing these acceptor groups does not significantly affect the frontier orbitals of the molecule; that is, while maintaining the multiple resonance characteristics, it ensures a reduction in the electron-donating ability of the nitrogen atom, thereby achieving a blue shift in the spectrum. Simultaneously, the acceptor groups introduced at the nitrogen atom para-position in the core structure of the compound of this invention also contribute to improving the stability of the molecular anion in the electrically excited state, thereby increasing device lifetime.

[0107] 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. Detailed Implementation

[0108] 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.

[0109] All the chemical reagents used in this invention, such as petroleum ether, tert-butylbenzene, ethyl acetate, sodium sulfate, toluene, dichloromethane, potassium carbonate, boron tribromide, N,N-diisopropylethylamine, and reaction intermediates, 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).

[0110] The synthesis method of the compound of the present invention is briefly described below (process (1)). First, the hydrogen atom between X1 and X2 is metallized at the ortho position using n-butyllithium or tert-butyllithium. Then, boron tribromide or the like is added to perform a lithium-boron or lithium-phosphorus metal exchange, followed by the addition of a Bronsted base such as N,N-diisopropylethylamine, thereby conducting a tandem borane-friedel-Crafts reaction to obtain the target compound.

[0111]

[0112] R 21 R 22 R 23 R 24 R 25 R 26 R 27 and R 28 Each group is independently selected from hydrogen, deuterium, or substituted or unsubstituted groups from the following: C6-C48 monocyclic aromatic hydrocarbons or fused-ring aromatic hydrocarbons, C3-C48 monocyclic heteroaromatic hydrocarbons or fused-ring heteroaromatic hydrocarbons, C6-C30 arylamino, C3-C30 heteroarylamino, C1-C36 alkyl, C1-C6 alkoxy, and R 21 To R 28 Not both are hydrogen, and R 21 To R 28 Two adjacent groups may bond together to form one of the following groups, substituted or unsubstituted: C1-C10 cycloalkanes, C6-C30 aromatics or C5-C30 heteroaromatics, wherein at least one hydrogen in the formed ring may be substituted by aryl, heteroaryl, diarylamino, diarylamino, arylhelelamino, alkyl, alkoxy or aryloxy, wherein at least one hydrogen in these may be substituted by aryl, heteroaryl or alkyl;

[0113] R 40 R 41 R 42Each of the following is independently selected from substituted C1-C30 alkyl, substituted C2-C10 alkenyl, substituted C2-C10 alkynyl, substituted C6-C48 monocyclic aromatic hydrocarbons, substituted C6-C48 fused-ring aromatic hydrocarbons, substituted or unsubstituted C3-C48 nitrogen-containing monocyclic heteroaromatic hydrocarbons, and substituted or unsubstituted C3-C48 nitrogen-containing fused-ring heteroaromatic hydrocarbons;

[0114] More specifically, the following provides methods for synthesizing representative compounds of the present invention.

[0115] Synthesis Examples

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

[0117]

[0118] Under a nitrogen atmosphere, a pentane solution of tert-butyllithium (8.01 mL, 1.60 M, 12.82 mmol) was slowly added to a 100 mL solution of tert-butylbenzene (5.00 g, 10.68 mmol) of M-1-1 at 0 °C. The temperature was then raised to 80 °C, 100 °C, and 120 °C, and reacted for 1 hour each time. After the reaction was completed, the temperature was lowered to -30 °C, and boron tribromide (4.02 g, 16.03 mmol) was slowly added. The mixture was stirred at room temperature for 0.5 hours. N,N-diisopropylethylamine (2.76 g, 21.37 mmol) was added at room temperature, and the reaction was continued at 145 °C for 6 hours before being stopped. The solvent was evaporated under vacuum, and the mixture was passed through a silica gel column (eluent: ethyl acetate: petroleum ether = 20:1) to give the target compound C-1 (0.71 g, 15% yield, HPLC purity 99.58%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 441.34 Elemental analysis results: Theoretical value: C, 84.37%; H, 3.65%; B, 2.45%; N, 9.52% Experimental values: C, 84.52%; H, 3.62%; B, 2.50%; N, 9.36% .

[0119] Synthesis Example 2: Synthesis of Compound M-2

[0120]

[0121] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-2-1 The target compound M-2 (0.71 g, 15% yield, HPLC purity 99.58%) was a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 443.40 Elemental analysis results: Theoretical value: C, 83.99%; H, 4.09%; B, 2.44％；N,9.48％ Experimental values: C, 84.25%; H, 4.03%; B, 2.52%; N, 9.20% .

[0122] Synthesis Example 3: Synthesis of Compound M-4

[0123]

[0124] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-4-1 The target compound M-4 (0.71 g, 15% yield, HPLC purity 99.68%) was a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 445.38 Elemental analysis results: Theoretical value: C, 83.61%; H, 4.53%; B, 2.43％；N,9.44％ Experimental values: C, 83.68%; H, 4.50%; B, 2.38%; N, 9.44% .

[0125] Synthesis Example 4: Synthesis of Compound M-5

[0126]

[0127] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-5-1 The target compound M-5 (0.74 g, 15% yield, HPLC purity 99.68%) was a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 459.38 Elemental analysis results: Theoretical value: C, 81.06%; H, 3.95%; B, 2.35%; N, 9.15%; O, 3.48% Experimental values: C, 81.25%; H, 3.92%; B, 2.33%; N, 9.25%; O, 3.25％ .

[0128] Synthesis Example 5: Synthesis of Compound M-7

[0129]

[0130] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-7-1 The target compound M-7 (0.73 g, 15% yield, HPLC purity 99.58%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 457.35 Elemental analysis results: Theoretical value: C, 81.42%; H, 3.53%; B, 2.36%; N, 9.19%; O, 3.50% Experimental values: C, 81.48%; H, 3.55%; B, 2.35%; N, 9.15%; O, 3.47％ .

[0131] Synthesis Example 6: Synthesis of Compound M-9

[0132]

[0133] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-9-1 The target compound M-9 (0.76 g, 15% yield, HPLC purity 99.68%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 473.40 Elemental analysis results: Theoretical value: C, 78.67%; H, 3.41%; B, 2.28%; N, 8.88%; O, 6.76% Experimental values: C, 78.72%; H, 3.45%; B, 2.24%; N, 8.83%; O, 6.76％ .

[0134] Synthesis Example 7: Synthesis of Compound M-10

[0135]

[0136] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-10-1 The target compound M-10 (0.76 g, 15% yield, HPLC purity 99.68%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 475.45 Elemental analysis results: Theoretical value: C, 78.33%; H, 3.82%; B, 2.27%; N, 8.84%; S, 6.74% Experimental values: C, 78.42%; H, 3.75%; B, 2.24%; N, 8.83%; S, 6.85％ .

[0137] Synthesis Example 8: Synthesis of Compound M-12

[0138]

[0139] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-12-1 The target compound M-12 (0.76 g, 15% yield, HPLC purity 99.68%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 473.40 Elemental analysis results: Theoretical value: C, 78.66%; H, 3.41%; B, 2.28%; N, 8.88%; S, 6.77% Experimental values: C, 78.75%; H, 3.42%; B, 2.24%; N, 8.83%; S, 6.76％ .

[0140] Synthesis Example 9: Synthesis of Compound M-14

[0141]

[0142] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-14-1 The target compound M-14 (0.78 g, 15% yield, HPLC purity 99.58%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 485.43 Elemental analysis results: Theoretical value: C, 84.13%; H, 4.98%; B, 2.23％；N,8.66％ Experimental values: C, 84.18%; H, 4.95%; B, 2.22%; N, 8.65% .

[0143] Synthesis Example 10: Synthesis of Compound M-16

[0144]

[0145] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-16-1 The target compound M-16 (0.77 g, 15% yield, HPLC purity 99.58%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 483.41 Elemental analysis results: Theoretical value: C, 84.48%; H, 4.59%; B, 2.24％；N,8.69％ Experimental values: C, 84.53%; H, 4.55%; B, 2.22%; N, 8.70% .

[0146] Synthesis Example 11: Synthesis of Compound M-18

[0147]

[0148] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-18-1 The target compound M-18 (0.59 g, 15% yield, HPLC purity 99.68%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 368.22 Elemental analysis results: Theoretical value: C, 81.55%; H, 3.56%; B, 2.94%; N, 7.61%; O, 4.35% Experimental values: C, 81.60%; H, 3.59%; B, 2.91%; N, 7.62%; O, 4.28％ .

[0149] Synthesis Example 12: Synthesis of Compound M-21

[0150]

[0151] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substanceM-21-1 The target compound M-21 (0.59 g, 15% yield, HPLC purity 99.68%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 370.25 Elemental analysis results: Theoretical value: C, 81.11%; H, 4.08%; B, 2.92%; N, 7.57%; O, 4.32% Experimental values: C, 81.15%; H, 4.05%; B, 2.91%; N, 7.62%; O, 4.27％ .

[0152] Synthesis Example 13: Synthesis of Compound M-22

[0153]

[0154] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-22-1 The target compound M-22 (0.62 g, 15% yield, HPLC purity 99.58%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 384.23 Elemental analysis results: Theoretical value: C, 78.16%; H, 3.41%; B, 2.81%; N, 7.29%; O, 8.33% Experimental values: C, 78.22%; H, 3.38%; B, 2.83%; N, 7.28%; O, 8.29％ .

[0155] Synthesis Example 14: Synthesis of Compound M-24

[0156]

[0157] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-24-1 The target compound M-24 (0.64 g, 15% yield, HPLC purity 99.58%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 400.30 Elemental analysis results: Theoretical value: C, 75.02%; H, 3.27%; B, 2.70%; N, 7.00%; O, 4.00%; S, 8.01% Experimental values: C, 75.04%; H, 3.25%; B, 2.73%; N, 7.01％；O,7.97％ .

[0158] Synthesis Example 15: Synthesis of Compound M-26

[0159]

[0160] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-26-1The target compound M-26 (0.66 g, 15% yield, HPLC purity 99.58%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 410.32 Elemental analysis results: Theoretical value: C, 81.97%; H, 4.67%; B, 2.63%; N, 6.83%; O, 3.90% Experimental values: C,82.05%;H,4.70%;B,2.60%;N,6.79%;O, 3.86％ .

[0161] Synthesis Example 16: Synthesis of Compound M-28

[0162]

[0163] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-28-1 The target compound M-28 (0.47 g, 15% yield, HPLC purity 99.58%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 295.08 Elemental analysis results: Theoretical value: C,77.33%;H,3.42%;B, 3.66%;N,4.75%;O,10.84% Experimental values: C,77.40%;H,3.41%;B,3.63%;N,4.76%;O, 10.80％ .

[0164] Synthesis Example 17: Synthesis of Compound M-29

[0165]

[0166] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-29-1 The target compound M-29 (0.50 g, 15% yield, HPLC purity 99.68%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 311.06 Elemental analysis results: Theoretical value: C,73.34%;H,3.24%;B, 3.47%;N,4.50%;O,5.14%;S,10.30% Experimental values: C,73.40%;H,3.22%;B,3.45%;N, 4.53%;O,5.11%;S,10.29% .

[0167] Synthesis Example 18: Synthesis of Compound M-31

[0168]

[0169] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-31-1The target compound M-31 (0.58 g, 15% yield, HPLC purity 99.68%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 359.00 Elemental analysis results: Theoretical value: C,63.73%;H,2.82%;B, 3.00%2;N,3.91%;O,4.47%;Se,22.05% Experimental values: C,63.78%;H,2.80%;B,3.03%2;N, 3.87%;O,4.44%;Se,22.08% .

[0170] Synthesis Example 19: Synthesis of Compound M-33

[0171]

[0172] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-33-1 The target compound M-33 (0.52 g, 15% yield, HPLC purity 99.58%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 327.03 Elemental analysis results: Theoretical value: C,69.74%;H,3.08%;B, 3.30%;N,4.28%;S,19.60% Experimental values: C,69.75%;H,3.07%;B,3.32%;N,4.26%;S, 19.60％ .

[0173] Synthesis Example 20: Synthesis of Compound M-34

[0174]

[0175] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-34-1 The target compound M-34 (0.60 g, 15% yield, HPLC purity 99.68%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 374.98 Elemental analysis results: Theoretical value: C,61.00%;H,2.69%;B, 2.89%;N,3.74%;S,8.57%;Se,21.11% Experimental values: C,61.05%;H,2.64%;B,2.87%;N, 3.76%;S,8.54%;Se,21.14% .

[0176] Synthesis Example 21: Synthesis of Compound M-36

[0177]

[0178] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-36-1The target compound M-36 (0.67 g, 15% yield, HPLC purity 99.58%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 421.50 Elemental analysis results: Theoretical value: C,54.20%;H,2.39%;B, 2.57%;N,3.33%;Se,37.51% Experimental values: C,54.23%;H,2.36%;B,2.59%;N,3.32%;Se, 37.50％ .

[0179] Synthesis Example 22: Synthesis of Compound M-37

[0180]

[0181] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-37-1 The target compound M-37 (0.75 g, 15% yield, HPLC purity 99.68%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 466.50 Elemental analysis results: Theoretical value: C,82.42%;H,3.24%;B, 2.32％；N,12.02％ Experimental values: C,82.45%;H,3.22%;B,2.31%;N,12.02% .

[0182] Synthesis Example 23: Synthesis of Compound M-39

[0183]

[0184] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-39-1 The target compound M-39 (0.75 g, 15% yield, HPLC purity 99.58%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 470.17 Elemental analysis results: Theoretical value: C,81.72%;H,4.07%;B, 2.30％；N,11.91％ Experimental values: C,81.78%;H,4.09%;B,2.24%;N,11.89% .

[0185] Synthesis Example 24: Synthesis of Compound M-52

[0186]

[0187] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-52-1The target compound M-52 (0.51 g, 15% yield, HPLC purity 99.68%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 320.51 Elemental analysis results: Theoretical value: C,75.04%;H,2.83%;B, 3.38%;N,8.75%;O,10.00% Experimental values: C,75.10%;H,2.81%;B,3.42%;N,8.71%;O, 9.96％ .

[0188] Synthesis Example 25: Synthesis of Compound M-79

[0189]

[0190] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-79-1 The target compound M-79 (0.78 g, 15% yield, HPLC purity 99.68%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 484.41 Elemental analysis results: Theoretical value: C,76.88%;H,3.33%;B, 2.23%;F,11.77%;N,5.78% Experimental values: C,76.93%;H,3.31%;B,2.25%;F,11.76%;N, 5.74％ .

[0191] Synthesis Example 26: Synthesis of Compound M-82

[0192]

[0193] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-82-1 The target compound M-82 (0.78 g, 15% yield, HPLC purity 99.58%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 488.40 Elemental analysis results: Theoretical value: C,76.25%;H,4.13%;B, 2.21%;F,11.67%;N,5.74% Experimental values: C,76.31%;H,4.16%;B,2.15%;F,11.65%;N, 5.73％ .

[0194] Synthesis Example 27: Synthesis of Compound M-106

[0195]

[0196] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-106-1The target compound M-106 (0.54 g, 15% yield, HPLC purity 99.68%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 338.21 Elemental analysis results: Theoretical value: C,67.50%;H,2.98%; B,3.20%;F,16.86%;O,9.46% Experimental values: C,67.55%;H,2.96%;B,3.23%;F,16.84%;O, 9.42％ .

[0197] Synthesis Example 28: Synthesis of Compound M-115

[0198]

[0199] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-115-1 The target compound M-115 (0.88 g, 15% yield, HPLC purity 99.58%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 552.40 Elemental analysis results: Theoretical value: C,69.59%;H,2.74%; B,1.96%;F,20.64%;N,5.07% Experimental values: C,69.66%;H,2.71%;B,1.98%;F,20.61%;N, 5.04％ .

[0200] Synthesis Example 29: Synthesis of Compound M-117

[0201]

[0202] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-117-1 The target compound M-117 (0.89 g, 15% yield, HPLC purity 99.68%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 556.41 Elemental analysis results: Theoretical value: C,69.09%;H,3.44%; B,1.94%;F,20.49%;N,5.04% Experimental values: C,69.14%;H,3.46%;B,1.91%;F,20.47%;N, 5.02％ .

[0203] Synthesis Example 30: Synthesis of Compound M-130

[0204]

[0205] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-130-1The target compound M-130 (0.65 g, 15% yield, HPLC purity 99.68%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 406.12 Elemental analysis results: Theoretical value: C,59.15%;H,2.23%; B,2.66%;F,28.07%;O,7.88% Experimental values: C,59.20%;H,2.25%;B,2.63%;F,28.04%;O, 7.87％ .

[0206] Synthesis Example 31: Synthesis of Compound M-157

[0207]

[0208] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-157-1 The target compound M-157 (0.79 g, 15% yield, HPLC purity 99.58%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 493.45 Elemental analysis results: Theoretical value: C,85.21%;H,4.09%; B,2.19%;N,8.52% Experimental values: C,85.28%;H,4.11%;B,2.14%;N,8.48% .

[0209] Synthesis Example 32: Synthesis of Compound M-160

[0210]

[0211] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-160-1 The target compound M-160 (0.80 g, 15% yield, HPLC purity 99.68%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 497.65 Elemental analysis results: Theoretical value: C,84.52%;H,4.86%; B,2.17%;N,8.45% Experimental values: C,84.61%;H,4.87%;B,2.12%;N,8.40% .

[0212] Synthesis Example 33: Synthesis of Compound M-184

[0213]

[0214] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-184-1The target compound M-184 (0.56 g, 15% yield, HPLC purity 99.68%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 347.20 Elemental analysis results: Theoretical value: C,79.57%;H,4.06%; B,3.11%;N,4.03%;O,9.22% Experimental values: C,79.61%;H,4.08%;B,3.09%;N,4.02%;O, 9.19％ .

[0215] Synthesis Example 34: Synthesis of Compound M-193

[0216]

[0217] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-193-1 The target compound M-193 (0.91 g, 15% yield, HPLC purity 99.58%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 570.61 Elemental analysis results: Theoretical value: C,84.22%;H,4.06%; B,1.89%;N,9.82% Experimental values: C,84.28%;H,4.08%;B,1.85%;N,9.78% .

[0218] Synthesis Example 35: Synthesis of Compound M-195

[0219]

[0220] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-195-1 The target compound M-195 (0.92 g, 15% yield, HPLC purity 99.68%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 574.49 Elemental analysis results: Theoretical value: C,83.63%;H,4.74%; B,1.88%;N,9.75% Experimental values: C,83.65%;H,4.76%;B,1.87%;N,9.72% .

[0221] Synthesis Example 36: Synthesis of Compound M-208

[0222]

[0223] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-208-1The target compound M-208 (0.68 g, 15% yield, HPLC purity 99.58%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 424.27 Elemental analysis results: Theoretical value: C,79.27%;H,4.04%; B,2.55%;N,6.60%;O,7.54% Experimental values: C,79.32%;H,4.03%;B,2.53%;N,6.59%;O, 7.53％ .

[0224] Synthesis Example 37: Synthesis of Compound M-235

[0225]

[0226] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-235-1 The target compound M-235 (0.79 g, 15% yield, HPLC purity 99.68%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 493.38 Elemental analysis results: Theoretical value: C,85.21%;H,4.09%; B,2.19%;N,8.52% Experimental values: C,85.25%;H,4.08%;B,2.18%;N,8.50% .

[0227] Synthesis Example 38: Synthesis of Compound M-238

[0228]

[0229] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-238-1 The target compound M-238 (0.80 g, 15% yield, HPLC purity 99.68%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 497.41 Elemental analysis results: Theoretical value: C,84.52%;H,4.86%; B,2.17%;N,8.45% Experimental values: C,84.57%;H,4.84%;B,2.16%;N,8.43% .

[0230] Synthesis Example 39: Synthesis of Compound M-262

[0231]

[0232] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-262-1The target compound M-262 (0.56 g, 15% yield, HPLC purity 99.68%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 347.22 Elemental analysis results: Theoretical value: C,79.57%;H,4.06%; B,3.11%;N,4.03%;O,9.22% Experimental values: C,79.60%;H,4.07%;B,3.10%;N,4.01%;O, 9.21％ .

[0233] Synthesis Example 40: Synthesis of Compound M-271

[0234]

[0235] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-271-1 The target compound M-271 (0.91 g, 15% yield, HPLC purity 99.68%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 570.56 Elemental analysis results: Theoretical value: C,84.22%;H,4.06%; B,1.89%;N,9.82% Experimental values: C,84.25%;H,4.05%;B,1.88%;N,9.81% .

[0236] Synthesis Example 41: Synthesis of Compound M-273

[0237]

[0238] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-273-1 The target compound M-273 (0.92 g, 15% yield, HPLC purity 99.68%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 574.53 Elemental analysis results: Theoretical value: C,83.63%;H,4.74%; B,1.88%;N,9.75% Experimental values: C,83.68%;H,4.72%;B,1.87%;N,9.73% .

[0239] Synthesis Example 42: Synthesis of Compound M-286

[0240]

[0241] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-286-1The target compound M-286 (0.68 g, 15% yield, HPLC purity 99.68%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 424.40 Elemental analysis results: Theoretical value: C,79.27%;H,4.04%; B,2.55%;N,6.60%;O,7.54% Experimental values: C,79.31%;H,4.03%;B,2.54%;N,6.59%;O, 7.53％ .

[0242] Synthesis Example 43: Synthesis of Compound M-313

[0243]

[0244] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-313-1 The target compound M-313 (0.79 g, 15% yield, HPLC purity 99.68%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 493.42 Elemental analysis results: Theoretical value: C,85.21%;H,4.09%; B,2.19%;N,8.52% Experimental values: C,85.25%;H,4.08%;B,2.18%;N,8.50% .

[0245] Synthesis Example 44: Synthesis of Compound M-316

[0246]

[0247] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-316-1 The target compound M-316 (0.80 g, 15% yield, HPLC purity 99.58%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 497.40 Elemental analysis results: Theoretical value: C,84.52%;H,4.86%; B,2.17%;N,8.45% Experimental values: C,84.55%;H,4.85%;B,2.17%;N,8.43% .

[0248] Synthesis Example 45: Synthesis of Compound M-340

[0249]

[0250] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-340-1The target compound M-340 (0.56 g, 15% yield, HPLC purity 99.68%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 347.18 Elemental analysis results: Theoretical value: C,79.57%;H,4.06%; B,3.11%;N,4.03%;O,9.22% Experimental values: C,79.61%;H,4.05%;B,3.10%;N,4.02%;O, 9.21％ .

[0251] Synthesis Example 46: Synthesis of Compound M-349

[0252]

[0253] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-349-1 The target compound M-349 (0.91 g, 15% yield, HPLC purity 99.68%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 570.40 Elemental analysis results: Theoretical value: C,84.22%;H,4.06%; B,1.89%;N,9.82% Experimental values: C,84.26%;H,4.04%;B,1.89%;N,9.80% .

[0254] Synthesis Example 47: Synthesis of Compound M-351

[0255]

[0256] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-351-1 The target compound M-351 (0.92 g, 15% yield, HPLC purity 99.58%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 574.51 Elemental analysis results: Theoretical value: C,83.63%;H,4.74%; B,1.88%;N,9.75% Experimental values: C,83.68%;H,4.72%;B,1.87%;N,9.73% .

[0257] Synthesis Example 48: Synthesis of Compound M-364

[0258]

[0259] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-364-1The target compound M-364 (0.68 g, 15% yield, HPLC purity 99.58%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 424.40 Elemental analysis results: Theoretical value: C,79.27%;H,4.04%; B,2.55%;N,6.60%;O,7.54% Experimental values: C,79.32%;H,4.03%;B,2.54%;N,6.59%;O, 7.52％ .

[0260] Synthesis Example 49: Synthesis of Compound M-391

[0261]

[0262] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-391-1 The target compound M-391 (1.04 g, 15% yield, HPLC purity 99.68%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 647.65 Elemental analysis results: Theoretical value: C,83.47%;H,4.05%; B,1.67%;N,10.82% Experimental values: C,83.52%;H,4.04%;B,1.66%;N,10.79% .

[0263] Synthesis Example 50: Synthesis of Compound M-394

[0264]

[0265] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-394-1 The target compound M-394 (1.04 g, 15% yield, HPLC purity 99.68%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 651.62 Elemental analysis results: Theoretical value: C,82.95%;H,4.64%; B,1.66%;N,10.75% Experimental values: C,82.98%;H,4.63%;B,1.65%;N,10.74% .

[0266] Synthesis Example 51: Synthesis of Compound M-418

[0267]

[0268] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-418-1The target compound M-418 (0.80 g, 15% yield, HPLC purity 99.58%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 501.40 Elemental analysis results: Theoretical value: C,79.06%;H,4.02%; B,2.16%;N,8.38%;O,6.38% Experimental values: C,79.11%;H,4.01%;B,2.15%;N,8.36%;O, 6.37％ .

[0269] Synthesis Example 52: Synthesis of Compound M-427

[0270]

[0271] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-427-1 The target compound M-427 (1.41 g, 15% yield, HPLC purity 99.58%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 878.92 Elemental analysis results: Theoretical value: C,82.00%;H,4.01%; B,1.23%;N,12.75% Experimental values: C,82.06%;H,3.99%;B,1.22%;N,12.72% .

[0272] Synthesis Example 53: Synthesis of Compound M-429

[0273]

[0274] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-429-1 The target compound M-429 (1.41 g, 15% yield, HPLC purity 99.68%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 882.96 Elemental analysis results: Theoretical value: C,81.63%;H,4.45%; B,1.22%;N,12.69% Experimental values: C,81.67%;H,4.44%;B,1.21%;N,12.67% .

[0275] Synthesis Example 54: Synthesis of Compound M-442

[0276]

[0277] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-442-1The target compound M-442 (1.17 g, 15% yield, HPLC purity 99.58%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 732.68 Elemental analysis results: Theoretical value: C,78.70%;H,3.99%; B,1.48%;N,11.47%;O,4.37% Experimental values: C,78.76%;H,3.98%;B,1.47%;N,11.45%;O, 4.36％ .

[0278] Synthesis Example 55: Synthesis of Compound M-469

[0279]

[0280] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-2-1 The target compound M-2 (0.98 g, 15% yield, HPLC purity 99.68%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 610.48 Elemental analysis results: Theoretical value: C,84.60%;H,3.80%;B, 1.77%;N,4.59%;O,5.24% Experimental values: C,84.66%;H,3.79%;B,1.76%;N,4.57%;O, 5.22％ .

[0281] Synthesis Example 56: Synthesis of Compound M-472

[0282]

[0283] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-472-1 The target compound M-472 (0.98 g, 15% yield, HPLC purity 99.68%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 614.51 Elemental analysis results: Theoretical value: C,84.05%;H,4.43%; B,1.76%;N,4.56%;O,5.21% Experimental values: C,84.09%;H,4.42%;B,1.76%;N,4.55%;O, 5.19％ .

[0284] Synthesis Example 57: Synthesis of Compound M-496

[0285]

[0286] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-496-1The target compound M-496 (0.74 g, 15% yield, HPLC purity 99.68%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 464.40 Elemental analysis results: Theoretical value: C,80.20%;H,3.69%; B,2.33%;O,13.78% Experimental values: C,80.26%;H,3.67%;B,2.32%;O,13.75% .

[0287] Synthesis Example 58: Synthesis of Compound M-505

[0288]

[0289] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-505-1 The target compound M-505 (1.29 g, 15% yield, HPLC purity 99.68%) was a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 804.72 Elemental analysis results: Theoretical value: C,83.59%;H,3.63%; B,1.34%;N,3.48%;O,7.95% Experimental values: C,83.63%;H,3.62%;B,1.33%;N,3.47%;O, 7.94％ .

[0290] Synthesis Example 59: Synthesis of Compound M-507

[0291]

[0292] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-507-1 The target compound M-507 (1.30 g, 15% yield, HPLC purity 99.58%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 808.70 Elemental analysis results: Theoretical value: C,83.17%;H,4.11%; B,1.34%;N,3.46%;O,7.91% Experimental values: C,83.22%;H,4.09%;B,1.33%;N,3.46%;O, 7.89％ .

[0293] Synthesis Example 60: Synthesis of Compound M-520

[0294]

[0295] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-520-1The target compound M-520 (1.05 g, 15% yield, HPLC purity 99.68%) was a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 658.60 Elemental analysis results: Theoretical value: C,80.26%;H,3.52%; B,1.64%;O,14.58% Experimental values: C,80.29%;H,3.51%;B,1.64%;O,14.56% .

[0296] Synthesis Example 61: Synthesis of Compound M-526

[0297]

[0298] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-526-1 The target compound M-526 (0.98 g, 15% yield, HPLC purity 99.58%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 610.48 Elemental analysis results: Theoretical value: C,84.60%;H,3.80%; B,1.77%;N,4.59%;O,5.24% Experimental values: C,84.66%;H,3.78%;B,1.76%;N,4.58%;O, 5.22％ .

[0299] Synthesis Example 62: Synthesis of Compound M-529

[0300]

[0301] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-529-1 The target compound M-529 (0.98 g, 15% yield, HPLC purity 99.68%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 614.61 Elemental analysis results: Theoretical value: C,84.05%;H,4.43%; B,1.76%;N,4.56%;O,5.21% Experimental values: C,84.08%;H,4.44%;B,1.75%;N,4.55%;O, 5.19％ .

[0302] Synthesis Example 63: Synthesis of Compound M-553

[0303]

[0304] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-553-1The target compound M-553 (0.74 g, 15% yield, HPLC purity 99.68%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 464.40 Elemental analysis results: Theoretical value: C,80.20%;H,3.69%; B,2.33%;O,13.78% Experimental values: C,80.26%;H,3.68%;B,2.32%;O,13.74% .

[0305] Synthesis Example 64: Synthesis of Compound M-562

[0306]

[0307] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-562-1 The target compound M-562 (1.29 g, 15% yield, HPLC purity 99.58%) was a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 804.72 Elemental analysis results: Theoretical value: C,83.59%;H,3.63%; B,1.34%;N,3.48%;O,7.95% Experimental values: C,83.63%;H,3.62%;B,1.33%;N,3.48%;O, 7.93％ .

[0308] Synthesis Example 65: Synthesis of Compound M-564

[0309]

[0310] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-564-1 The target compound M-564 (1.30 g, 15% yield, HPLC purity 99.68%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 808.70 Elemental analysis results: Theoretical value: C,83.17%;H,4.11%; B,1.34%;N,3.46%;O,7.91% Experimental values: C,83.23%;H,4.10%;B,1.33%;N,3.45%;O, 7.88％ .

[0311] Synthesis Example 66: Synthesis of Compound M-577

[0312]

[0313] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-577-1The target compound M-577 (1.05 g, 15% yield, HPLC purity 99.58%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 658.61 Elemental analysis results: Theoretical value: C,80.26%;H,3.52%; B,1.64%;O,14.58% Experimental values: C,80.29%;H,3.51%;B,1.64%;O,14.56% .

[0314] Synthesis Example 67: Synthesis of Compound M-583

[0315]

[0316] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-583-1 The target compound M-583 (1.00 g, 15% yield, HPLC purity 99.68%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 626.68 Elemental analysis results: Theoretical value: C,82.43%;H,3.70%; B,1.73%;N,4.47%;O,2.55%;S,5.12% Experimental values: C,82.48%;H,3.69%;B,1.72%;N, 4.46%;O,2.54%;S,5.11% .

[0317] Synthesis Example 68: Synthesis of Compound M-586

[0318]

[0319] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-586-1 The target compound M-586 (1.01 g, 15% yield, HPLC purity 99.58%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 630.62 Elemental analysis results: Theoretical value: C,81.91%;H,4.32%; B,1.71%;N,4.44%;O,2.54%;S,5.08% Experimental values: C,81.96%;H,4.31%;B,1.70%;N, 4.43%;O,2.54%;S,5.06% .

[0320] Synthesis Example 69: Synthesis of Compound M-610

[0321]

[0322] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-610-1The target compound M-610 (0.77 g, 15% yield, HPLC purity 99.68%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 480.40 Elemental analysis results: Theoretical value: C,77.52%;H,3.57%; B,2.25%;O,9.99%;S,6.67% Experimental values: C,77.58%;H,3.56%;B,2.24%;O,9.96%;S, 6.66％ .

[0323] Synthesis Example 70: Synthesis of Compound M-619

[0324]

[0325] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-619-1 The target compound M-619 (1.34 g, 15% yield, HPLC purity 99.68%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 836.82 Elemental analysis results: Theoretical value: C,80.38%;H,3.49%; B,1.29%;N,3.35%;O,3.82%;S,7.66% Experimental values: C,80.42%;H,3.48%;B,1.29%;N, 3.34%;O,3.82%;S,7.64% .

[0326] Synthesis Example 71: Synthesis of Compound M-621

[0327]

[0328] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-621-1 The target compound M-621 (1.35 g, 15% yield, HPLC purity 99.58%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 840.85 Elemental analysis results: Theoretical value: C,80.00%;H,3.96%; B,1.29%;N,3.33%;O,3.81%;S,7.63% Experimental values: C,80.08%;H,3.95%;B,1.29%;N, 3.32%;O,3.79%;S,7.59% .

[0329] Synthesis Example 72: Synthesis of Compound M-634

[0330]

[0331] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-634-1The target compound M-634 (1.11 g, 15% yield, HPLC purity 99.58%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 690.62 Elemental analysis results: Theoretical value: C,76.53%;H,3.36%; B,1.57%;O,9.27%;S,9.28% Experimental values: C,76.58%;H,3.35%;B,1.57%;O,9.24%;S, 9.27％ .

[0332] Synthesis Example 73: Synthesis of Compound M-640

[0333]

[0334] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-640-1 The target compound M-640 (1.00 g, 15% yield, HPLC purity 99.68%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 626.61 Elemental analysis results: Theoretical value: C,82.43%;H,3.70%; B,1.73%;N,4.47%;O,2.55%;S,5.12% Experimental values: C,82.48%;H,3.68%;B,1.73%;N, 4.46%;O,2.55%;S,5.10% .

[0335] Synthesis Example 74: Synthesis of Compound M-643

[0336]

[0337] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-643-1 The target compound M-643 (1.01 g, 15% yield, HPLC purity 99.68%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 630.62 Elemental analysis results: Theoretical value: C,81.91%;H,4.32%; B,1.71%;N,4.44%;O,2.54%;S,5.08% Experimental values: C,81.97%;H,4.31%;B,1.71%;N, 4.42%;O,2.54%;S,5.05% .

[0338] Synthesis Example 75: Synthesis of Compound M-667

[0339]

[0340] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-667-1The target compound M-667 (0.77 g, 15% yield, HPLC purity 99.68%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 480.40 Elemental analysis results: Theoretical value: C,77.52%;H,3.57%; B,2.25%;O,9.99%;S,6.67% Experimental values: C,77.58%;H,3.56%;B,2.25%;O,9.96%;S, 6.65％ .

[0341] Synthesis Example 76: Synthesis of Compound M-676

[0342]

[0343] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-676-1 The target compound M-676 (1.34 g, 15% yield, HPLC purity 99.68%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 836.83 Elemental analysis results: Theoretical value: C,80.38%;H,3.49%; B,1.29%;N,3.35%;O,3.82%;S,7.66% Experimental values: C,80.43%;H,3.48%;B,1.29%;N, 3.34%;O,3.81%;S,7.64% .

[0344] Synthesis Example 77: Synthesis of Compound M-678

[0345]

[0346] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-678-1 The target compound M-678 (1.35 g, 15% yield, HPLC purity 99.68%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 840.91 Elemental analysis results: Theoretical value: C,80.00%;H,3.96%; B,1.29%;N,3.33%;O,3.81%;S,7.63% Experimental values: C,80.08%;H,3.94%;B,1.29%;N, 3.31%;O,3.80%;S,7.60% .

[0347] Synthesis Example 78: Synthesis of Compound M-691

[0348]

[0349] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-691-1The target compound M-691 (1.11 g, 15% yield, HPLC purity 99.58%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 690.61 Elemental analysis results: Theoretical value: C,76.53%;H,3.36%; B,1.57%;O,9.27%;S,9.28% Experimental values: C,76.58%;H,3.36%;B,1.57%;O,9.25%;S, 9.25％ .

[0350] Synthesis Example 79: Synthesis of Compound M-697

[0351]

[0352] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-697-1 The target compound M-697 (1.08 g, 15% yield, HPLC purity 99.68%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 673.40 Elemental analysis results: Theoretical value: C,76.69%;H,3.44%; B,1.61%;N,4.16%;O,2.38%;Se,11.73% Experimental values: C,76.74%;H,3.42%;B,1.61%;N, 4.16%;O,2.38%;Se,11.70% .

[0353] Synthesis Example 80: Synthesis of Compound M-700

[0354]

[0355] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-700-1 The target compound M-700 (1.09 g, 15% yield, HPLC purity 99.68%) was a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 677.52 Elemental analysis results: Theoretical value: C,76.23%;H,4.02%; B,1.60%;N,4.14%;O,2.36%;Se,11.66% Experimental values: C,76.29%;H,4.01%;B,1.60%;N, 4.12%;O,2.36%;Se,11.63% .

[0356] Synthesis Example 81: Synthesis of Compound M-724

[0357]

[0358] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-724-1The target compound M-724 (0.84 g, 15% yield, HPLC purity 99.68%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 527.41 Elemental analysis results: Theoretical value: C, 70.62%; H, 3.25%; B,2.05%;O,9.10%;Se,14.98% Experimental values: C, 70.68%; H, 3.25%; B, 2.05%; O, 9.07%; Se, 14.95％ .

[0359] Synthesis Example 82: Synthesis of Compound M-733

[0360]

[0361] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-733-1 The target compound M-733 (1.49 g, 15% yield, HPLC purity 99.68%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 930.68 Elemental analysis results: Theoretical value: C, 72.28%; H, 3.14%; B,1.16%;N,3.01%;O,3.44%;Se,16.97% Experimental values: C,72.35%;H,3.12%;B,1.16%;N, 3.01%;O,3.42%;Se,16.94% .

[0362] Synthesis Example 83: Synthesis of Compound M-735

[0363]

[0364] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-735-1 The target compound M-735 (1.50 g, 15% yield, HPLC purity 99.68%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 934.72 Elemental analysis results: Theoretical value: C, 71.96%; H, 3.56%; B,1.16%;N,3.00%;O,3.42%;Se,16.90% Experimental values: C,71.90%;H,3.57%;B,1.17%;N, 3.00%;O,3.42%;Se,16.94% .

[0365] Synthesis Example 84: Synthesis of Compound M-748

[0366]

[0367] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-748-1The target compound M-748 (1.26 g, 15% yield, HPLC purity 99.58%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 784.40 Elemental analysis results: Theoretical value: C, 67.37%; H, 2.96%; B,1.38%;O,8.16%;Se,20.14% Experimental values: C, 67.39%; H, 2.99%; B, 1.38%; O, 8.15%; Se, 20.10％ .

[0368] Synthesis Example 85: Synthesis of Compound M-754

[0369]

[0370] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-754-1 The target compound M-754 (1.08 g, 15% yield, HPLC purity 99.68%) was a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 673.40 Elemental analysis results: Theoretical value: C, 76.69%; H, 3.44%; B,1.61%;N,4.16%;O,2.38%;Se,11.73% Experimental values: C,76.65%;H,3.44%;B,1.61%;N, 4.17%;O,2.38%;Se,11.76% .

[0371] Synthesis Example 86: Synthesis of Compound M-757

[0372]

[0373] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-757-1 The target compound M-757 (1.09 g, 16% yield, HPLC purity 99.68%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 677.40 Elemental analysis results: Theoretical value: C, 76.23%; H, 4.02%; B,1.60%;N,4.14%;O,2.36%;Se,11.66% Experimental values: C,76.29%;H,4.01%;B,1.60%;N, 4.12%;O,2.36%;Se,11.63% .

[0374] Synthesis Example 87: Synthesis of Compound M-781

[0375]

[0376] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-781-1The target compound M-781 (0.84 g, 15% yield, HPLC purity 99.68%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 527.40 Elemental analysis results: Theoretical value: C, 70.62%; H, 3.25%; B,2.05%;O,9.10%;Se,14.98% Experimental values: C, 70.66%; H, 3.25%; B, 2.05%; O, 9.08%; Se, 14.96％ .

[0377] Synthesis Example 88: Synthesis of Compound M-790

[0378]

[0379] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-790-1 The target compound M-790 (1.49 g, 16% yield, HPLC purity 99.68%) was a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 930.67 Elemental analysis results: Theoretical value: C, 72.28%; H, 3.14%; B,1.16%;N,3.01%;O,3.44%;Se,16.97% Experimental values: C,72.33%;H,3.14%;B,1.16%;N, 3.01%;O,3.42%;Se,16.94% .

[0380] Synthesis Example 89: Synthesis of Compound M-792

[0381]

[0382] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-792-1 The target compound M-792 (1.50 g, 15% yield, HPLC purity 99.68%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 934.70 Elemental analysis results: Theoretical value: C, 71.96%; H, 3.56%; B,1.16%;N,3.00%;O,3.42%;Se,16.90% Experimental values: C,72.02%;H,3.54%;B,1.16%;N, 3.00%;O,3.41%;Se,16.87% .

[0383] Synthesis Example 90: Synthesis of Compound M-805

[0384]

[0385] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-805-1The target compound M-805 (1.26 g, 15% yield, HPLC purity 99.58%) was a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 784.40 Elemental analysis results: Theoretical value: C, 67.37%; H, 2.96%; B,1.38%;O,8.16%;Se,20.14% Experimental values: C, 67.42%; H, 2.96%; B, 1.38%; O, 8.14%; Se, 20.11％ .

[0386] Synthesis Example 91: Synthesis of Compound M-811

[0387]

[0388] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-811-1 The target compound M-811 (0.96 g, 15% yield, HPLC purity 99.68%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 596.56 Elemental analysis results: Theoretical value: C, 86.58%; H, 4.22%; B,1.81%;N,4.70%;O,2.68% Experimental values: C,86.62%;H,4.22%;B,1.81%;N,4.70%;O, 2.68％ .

[0389] Synthesis Example 92: Synthesis of Compound M-814

[0390]

[0391] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-814-1 The target compound M-814 (0.96 g, 15% yield, HPLC purity 99.68%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 600.53 Elemental analysis results: Theoretical value: C,86.00%;H,4.87%; B,1.80%;N,4.66%;O,2.66% Experimental values: C,86.08%;H,4.85%;B,1.80%;N,4.63%;O, 2.63％ .

[0392] Synthesis Example 93: Synthesis of Compound M-838

[0393]

[0394] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-838-1The target compound M-838 (0.72 g, 15% yield, HPLC purity 99.58%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 450.40 Elemental analysis results: Theoretical value: C,82.69%;H,4.25%; B,2.40%;O,10.66% Experimental values: C,82.72%;H,4.24%;B,2.40%;O,10.64% .

[0395] Synthesis Example 94: Synthesis of Compound M-847

[0396]

[0397] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-847-1 The target compound M-847 (1.24 g, 15% yield, HPLC purity 99.68%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 776.72 Elemental analysis results: Theoretical value: C,86.60%;H,4.28%; B,1.39%;N,3.61%;O,4.12% Experimental values: C,86.65%;H,4.26%;B,1.39%;N,3.60%;O, 4.10％ .

[0398] Synthesis Example 95: Synthesis of Compound M-849

[0399]

[0400] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-849-1 The target compound M-849 (1.25 g, 15% yield, HPLC purity 99.68%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 780.70 Elemental analysis results: Theoretical value: C,86.15%;H,4.78%; B,1.38%;N,3.59%;O,4.10% Experimental values: C,86.19%;H,4.77%;B,1.38%;N,3.58%;O, 4.09％ .

[0401] Synthesis Example 96: Synthesis of Compound M-862

[0402]

[0403] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-862-1The target compound M-862 (1.01 g, 15% yield, HPLC purity 99.68%) was a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 630.58 Elemental analysis results: Theoretical value: C,83.82%;H,4.32%; B,1.71%;O,10.15% Experimental values: C,83.88%;H,4.30%;B,1.71%;O,10.11% .

[0404] Synthesis Example 97: Synthesis of Compound M-868

[0405]

[0406] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-868-1 The target compound M-868 (0.96 g, 15% yield, HPLC purity 99.68%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 596.50 Elemental analysis results: Theoretical value: C,86.58%;H,4.22%; B,1.81%;N,4.70%;O,2.68% Experimental values: C,86.62%;H,4.21%;B,1.81%;N,4.68%;O, 2.67％ .

[0407] Synthesis Example 98: Synthesis of Compound M-871

[0408]

[0409] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M- 871-1. The target compound M-871 (0.96 g, 15% yield, HPLC purity 99.58%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 600.56 Elemental analysis results: Theoretical value: C,86.00%;H,4.87%; B,1.80%;N,4.66%;O,2.66% Experimental values: C,86.08%;H,4.85%;B,1.80%;N,4.63%;O, 2.63％ .

[0410] Synthesis Example 99: Synthesis of Compound M-895

[0411]

[0412] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-895-1The target compound M-895 (0.72 g, 15% yield, HPLC purity 99.68%) was a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 450.30 Elemental analysis results: Theoretical value: C,82.69%;H,4.25%; B,2.40%;O,10.66% Experimental values: C,82.73%;H,4.23%;B,2.40%;O,10.64% .

[0413] Synthesis Example 100: Synthesis of Compound M-904

[0414]

[0415] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-904-1 The target compound M-904 (1.24 g, 15% yield, HPLC purity 99.68%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 776.70 Elemental analysis results: Theoretical value: C,86.60%;H,4.28%; B,1.39%;N,3.61%;O,4.12% Experimental values: C,86.66%;H,4.25%;B,1.39%;N,3.61%;O, 4.09％ ;

[0416] Synthesis Example 101: Synthesis of Compound M-906

[0417]

[0418] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M- 906-1. The target compound M-906 (1.25 g, 15% yield, HPLC purity 99.68%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 780.75 Elemental analysis results: Theoretical value: C,86.15%;H,4.78%; B,1.38%;N,3.59%;O,4.10% Experimental values: C,86.14%;H,4.79%;B,1.38%;N,3.58%;O, 4.11％ .

[0419] Synthesis Example 102: Synthesis of Compound M-907

[0420]

[0421] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-919-1The target compound M-919 (1.01 g, 15% yield, HPLC purity 99.68%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 630.56 Elemental analysis results: Theoretical value: C,83.82%;H,4.32%; B,1.71%;O,10.15% Experimental values: C,83.81%;H,4.33%;B,1.71%;O,10.15% .

[0422] Synthesis Example 103: Synthesis of Compound M-908

[0423]

[0424] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-925-1 The target compound M-925 (1.01 g, 15% yield, HPLC purity 99.68%) was a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 632.54 Elemental analysis results: Theoretical value: C,79.75%;H,3.98%; B,1.71%;N,4.43%;O,5.06%;S,5.07% Experimental values: C,79.78%;H,3.98%;B,1.72%;N, 4.43%;O,5.04%;S,5.05% .

[0425] Synthesis Example 104: Synthesis of Compound M-928

[0426]

[0427] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-928-1 The target compound M-928 (1.02 g, 15% yield, HPLC purity 99.68%) was a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 636.62 Elemental analysis results: Theoretical value: C,79.25%;H,4.59%; B,1.70%;N,4.40%;O,5.03%;S,5.04% Experimental values: C,79.29%;H,4.58%;B,1.70%;N, 4.40%;O,5.01%;S,5.03% .

[0428] Synthesis Example 105: Synthesis of Compound M-952

[0429]

[0430] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-952-1The target compound M-952 (0.78 g, 15% yield, HPLC purity 99.68%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 486.40 Elemental analysis results: Theoretical value: C,74.09%;H,3.94%; B,2.22%;O,13.16%;S,6.59% Experimental values: C,74.08%;H,3.95%;B,2.22%;O,13.13%;S, 6.62％ .

[0431] Synthesis Example 106: Synthesis of Compound M-961

[0432]

[0433] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-961-1 The target compound M-961 (1.36 g, 15% yield, HPLC purity 99.68%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 848.80 Elemental analysis results: Theoretical value: C,76.41%;H,3.92%; B,1.27%;N,3.30%;O,7.54%;S,7.55% Experimental values: C,76.40%;H,3.92%;B,1.27%;N, 3.31%;O,7.53%;S,7.56% .

[0434] Synthesis Example 107: Synthesis of Compound M-963

[0435]

[0436] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-963-1 The target compound M-963 (1.37 g, 15% yield, HPLC purity 99.58%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 852.85 Elemental analysis results: Theoretical value: C,76.05%;H,4.37%; B,1.27%;N,3.28%;O,7.50%;S,7.52% Experimental values: C,76.08%;H,4.37%;B,1.27%;N, 3.28%;O,7.49%;S,7.50% .

[0437] Synthesis Example 108: Synthesis of Compound M-975

[0438]

[0439] This embodiment is basically the same as the synthesis embodiment 1, except that: in this example, it is necessary to... M-1-1 Converted to equal amounts of substance M-975-1The target compound M-975 (1.13 g, 15% yield, HPLC purity 99.68%) was a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 702.60 Elemental analysis results: Theoretical value: C,71.80%;H,3.87%; B,1.54%;O,13.66%;S,9.13% Experimental values: C,71.85%;H,3.87%;B,1.54%;O,13.63%;S, 9.11％ .

[0440] 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.

[0441] 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.

[0442] 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).

[0443] 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).

[0444] 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.

[0445] The emissive layer includes luminescent dyes (i.e., dopants) that can emit different wavelengths of light, and may also include a host material. The emissive layer can be a monochromatic emissive layer emitting a single color such as red, green, or blue. Multiple monochromatic emissive layers of different colors can be arranged in a planar pattern according to pixel design, or they can be stacked together to form a colored emissive layer. When different colored emissive layers are stacked together, they can be separated from each other or connected to each other. The emissive layer can also be a single colored emissive layer that can simultaneously emit different colors such as red, green, and blue.

[0446] 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).

[0447] The fabrication process of the organic electroluminescent device of the present invention is described as follows: an anode 2, a hole transport layer 3, an organic light-emitting layer 4, an electron transport layer 5, and a cathode 6 are sequentially deposited on a substrate 1, and then encapsulated. Specifically, the organic light-emitting layer 4 is formed by co-deposition of a wide-bandgap material source, an electron donor-type material source, an electron acceptor-type material source, and a resonant TADF material source.

[0448] Specifically, the method for fabricating the organic electroluminescent device of the present invention includes the following steps:

[0449] 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.

[0450] 2. Place the glass plate with the anode inside the vacuum chamber and evacuate to a vacuum level of 1×10⁻⁶. -5 ~9×10 -3 Pa, a hole injection layer is vacuum-deposited on the above-mentioned anodic layer film at a deposition rate of 0.1-0.5 nm / s;

[0451] 3. A hole transport layer is vacuum-deposited on top of the hole injection layer at a deposition rate of 0.1-0.5 nm / s.

[0452] 4. The light-emitting layer of the device is vacuum-deposited on the hole transport layer. The light-emitting layer includes the host material and TADF 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 the preset doping ratio.

[0453] 5. The electron transport layer material of the device is vacuum-deposited on top of the organic light-emitting layer at a deposition rate of 0.1-0.5 nm / s;

[0454] 6. A LiF layer is vacuum-deposited at 0.1-0.5 nm / s as the electron injection layer on the electron transport layer, and an Al layer is vacuum-deposited at 0.5-1 nm / s as the cathode of the device.

[0455] 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.

[0456] The organic electroluminescent device of the present invention will be further described below through specific embodiments.

[0457] Example 1

[0458] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0459] ITO / HI(10nm) / HT(30nm) / Host:3wt%:M-1(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0460] In this embodiment, the anode is ITO; the hole injection layer is made of HI, with a total thickness of 5-30 nm, and 10 nm in this embodiment; the hole transport layer is made of HI, with a total thickness of 5-500 nm, and 40 nm in this embodiment; the host is the main material of the wide bandgap organic light-emitting layer, M-1 is a dye with a doping concentration of 3 wt%, and the thickness of the organic light-emitting layer is generally 1-200 nm, and 30 nm in this embodiment; the electron transport layer is made of ET, with a thickness of 5-300 nm, and 30 nm in this embodiment; the electron injection layer and cathode materials are selected as LiF (0.5 nm) and aluminum (150 nm).

[0461] Example 2

[0462] The preparation method is the same as in Example 1, except that the wide-bandgap host material used in the light-emitting layer is replaced with a TADF-type host TD. The specific device structure is as follows:

[0463] ITO / HI(10nm) / HT(30nm) / TD:3wt%:M-1(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0464] Example 3

[0465] The preparation method is the same as in Example 1, except that the dye is replaced by M-4 instead of M-1. The specific device structure is as follows:

[0466] ITO / HI(10nm) / HT(30nm) / Host:3wt%:M-4(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0467] Example 4

[0468] The preparation method is the same as in Example 2, except that the dye is replaced by M-4 instead of M-1. The specific device structure is as follows:

[0469] ITO / HI(10nm) / HT(30nm) / TD:3wt%:M-4(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0470] Example 5

[0471] The preparation method is the same as in Example 1, except that the dye is replaced by M-37 instead of M-1. The specific device structure is as follows:

[0472] ITO / HI(10nm) / HT(30nm) / Host:3wt%:M-37(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0473] Example 6

[0474] The preparation method is the same as in Example 2, except that the dye is replaced by M-37 instead of M-1. The specific device structure is as follows:

[0475] ITO / HI(10nm) / HT(30nm) / TD:3wt%:M-37(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0476] Example 7

[0477] The preparation method is the same as in Example 1, except that the dye is replaced by M-39 instead of M-1. The specific device structure is as follows:

[0478] ITO / HI(10nm) / HT(30nm) / Host:3wt%:M-39(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0479] Example 8

[0480] The preparation method is the same as in Example 2, except that the dye is replaced by M-39 instead of M-1. The specific device structure is as follows:

[0481] ITO / HI(10nm) / HT(30nm) / TD:3wt%:M-39(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0482] Example 9

[0483] The preparation method is the same as in Example 1, except that the dye is replaced by M-79 instead of M-1. The specific device structure is as follows:

[0484] ITO / HI(10nm) / HT(30nm) / Host:3wt%:M-79(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0485] Example 10

[0486] The preparation method is the same as in Example 2, except that the dye is replaced by M-79 instead of M-1. The specific device structure is as follows:

[0487] ITO / HI(10nm) / HT(30nm) / TD:3wt%:M-79(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0488] Example 11

[0489] The preparation method is the same as in Example 1, except that the dye is replaced by M-82 instead of M-1. The specific device structure is as follows:

[0490] ITO / HI(10nm) / HT(30nm) / Host:3wt%:M-82(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0491] Example 12

[0492] The preparation method is the same as in Example 2, except that the dye is replaced by M-82 instead of M-1. The specific device structure is as follows:

[0493] ITO / HI(10nm) / HT(30nm) / TD:3wt%:M-82(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0494] Example 13

[0495] The preparation method is the same as in Example 1, except that the dye is replaced by M-157 instead of M-1. The specific device structure is as follows:

[0496] ITO / HI(10nm) / HT(30nm) / Host:3wt%:M-157(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0497] Example 14

[0498] The preparation method is the same as in Example 2, except that the dye is replaced by M-157. The specific device structure is as follows:

[0499] ITO / HI(10nm) / HT(30nm) / TD:3wt%:M-157(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0500] Example 15

[0501] The preparation method is the same as in Example 1, except that the dye is replaced by M-160 instead of M-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / Host: 3wt%: M-160 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0502] Example 16

[0503] The preparation method is the same as in Example 2, except that the dye is replaced by M-160 instead of M-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / TD:3wt%:M-160 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0504] Example 17

[0505] The preparation method is the same as in Example 1, except that the dye is replaced by M-193 instead of M-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / Host: 3wt%: M-193 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0506] Example 18

[0507] The preparation method is the same as in Example 2, except that the dye is replaced by M-193 instead of M-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / TD:3wt%:M-193 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0508] Example 19

[0509] The preparation method is the same as in Example 1, except that the dye is replaced by M-195 instead of M-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / Host: 3wt%: M-195 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0510] Example 20

[0511] The preparation method is the same as in Example 2, except that the dye is replaced by M-195 instead of M-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / TD:3wt%:M-195 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0512] Example 21

[0513] The preparation method is the same as in Example 1, except that the dye is replaced by M-391 instead of M-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / Host: 3wt%: M-391 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0514] Example 22

[0515] The preparation method is the same as in Example 2, except that the dye is replaced by M-391 instead of M-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / TD:3wt%:M-391 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0516] Example 23

[0517] The preparation method is the same as in Example 1, except that the dye is replaced by M-394 instead of M-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / Host: 3wt%: M-394 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0518] Example 24

[0519] The preparation method is the same as in Example 2, except that the dye is replaced by M-394 instead of M-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / TD:3wt%:M-394 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0520] Example 25

[0521] The preparation method is the same as in Example 1, except that the dye is replaced by M-427 instead of M-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / Host: 3wt%: M-427 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0522] Example 26

[0523] The preparation method is the same as in Example 2, except that the dye is replaced by M-427 instead of M-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / TD:3wt%:M-427 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0524] Example 27

[0525] The preparation method is the same as in Example 1, except that the dye is replaced by M-429 instead of M-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / Host: 3wt%: M-429 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0526] Example 28

[0527] The preparation method is the same as in Example 2, except that the dye is replaced by M-429 instead of M-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / TD:3wt%:M-429 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0528] Example 29

[0529] The preparation method is the same as in Example 1, except that the dye is replaced by M-469 instead of M-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / Host: 3wt%: M-469 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0530] Example 30

[0531] The preparation method is the same as in Example 2, except that the dye is replaced by M-469 instead of M-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / TD:3wt%:M-469 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0532] Example 31

[0533] The preparation method is the same as in Example 1, except that the dye is replaced by M-472 instead of M-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / Host: 3wt%: M-472 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0534] Example 32

[0535] The preparation method is the same as in Example 2, except that the dye is replaced by M-472. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / TD:3wt%:M-472 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0536] Example 33

[0537] The preparation method is the same as in Example 1, except that the dye is replaced by M-505 instead of M-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / Host: 3wt%: M-472 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0538] Example 34

[0539] The preparation method is the same as in Example 2, except that the dye is replaced by M-505 instead of M-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / TD:3wt%:M-2 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0540] Example 35

[0541] The preparation method is the same as in Example 1, except that the dye is replaced by M-507 instead of M-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / Host: 3wt%: M-507 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0542] Example 36

[0543] The preparation method is the same as in Example 2, except that the dye is replaced by M-507 instead of M-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / TD:3wt%:M-507 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0544] Example 37

[0545] The preparation method is the same as in Example 1, except that the dye is replaced by M-583 instead of M-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / Host: 3wt%: M-583 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0546] Example 38

[0547] The preparation method is the same as in Example 2, except that the dye is replaced by M-583 instead of M-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / TD:3wt%:M-583 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0548] Example 39

[0549] The preparation method is the same as in Example 1, except that the dye is replaced by M-586 instead of M-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / Host: 3wt%: M-586 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0550] Example 40

[0551] The preparation method is the same as in Example 2, except that the dye is replaced by M-586 instead of M-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / TD:3wt%:M-586 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0552] Example 41

[0553] The preparation method is the same as in Example 1, except that the dye is replaced by M-697 instead of M-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / Host: 3wt%: M-697 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0554] Example 42

[0555] The preparation method is the same as in Example 2, except that the dye is replaced by M-697 instead of M-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / TD:3wt%:M-697 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0556] Example 43

[0557] The preparation method is the same as in Example 1, except that the dye is replaced by M-700 instead of M-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / Host: 3wt%: M-700 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0558] Example 44

[0559] The preparation method is the same as in Example 2, except that the dye is replaced by M-700 instead of M-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / TD:3wt%:M-700 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0560] Example 45

[0561] The preparation method is the same as in Example 1, except that the dye is replaced by M-811 instead of M-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / Host: 3wt%: M-811 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0562] Example 46

[0563] The preparation method is the same as in Example 2, except that the dye is replaced by M-811 instead of M-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / TD:3wt%:M-811 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0564] Example 47

[0565] The preparation method is the same as in Example 1, except that the dye is replaced by M-814 instead of M-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / Host: 3wt%: M-814 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0566] Example 48

[0567] The preparation method is the same as in Example 2, except that the dye is replaced by M-814 instead of M-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / TD:3wt%:M-814 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0568] Example 49

[0569] The preparation method is the same as in Example 1, except that the dye is replaced by M-925 instead of M-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / Host: 3wt%: M-925 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0570] Example 50

[0571] The preparation method is the same as in Example 2, except that the dye is replaced by M-925 instead of M-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / TD:3wt%:M-925 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0572] Example 51

[0573] The preparation method is the same as in Example 1, except that the dye is replaced by M-928 instead of M-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / Host: 3wt%: M-928 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0574] Example 52

[0575] The preparation method is the same as in Example 2, except that the dye is replaced by M-928 instead of M-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / TD:3wt%:M-928 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0576] Comparative Device Example 1

[0577] The preparation method is the same as in Example 1, except that the dye is replaced by P-1 instead of M-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / Host: 3wt%: P-1 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0578] Comparative Device Example 2

[0579] The preparation method is the same as in Example 2, except that the dye is replaced by P-1 instead of M-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / TD:3wt%:P-1 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0580] Comparative Device Example 3

[0581] The preparation method is the same as in Example 1, except that the dye is replaced by P-2 instead of M-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / Host: 3wt%: P-2 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0582] Comparative Device Example 4

[0583] The preparation method is the same as in Example 2, except that the dye is replaced by P-2 instead of M-1. The specific device structure is as follows: ITO / HI (10nm) / HT (30nm) / TD:3wt%:P-2 (30nm) / ET (30nm) / LiF (0.5nm) / Al (150nm)

[0584] The structural formulas of the various organic materials used in the above embodiments are as follows:

[0585]

[0586]

[0587] The specific performance data of the organic electroluminescent devices D1 to D60 and devices DD1 to DD6 prepared in the above-described device embodiments are detailed in Table 1 below:

[0588] Table 1:

[0589]

[0590]

[0591]

[0592] The experimental data above show that the novel MR-TADF material provided by this invention has high color purity and high luminous efficiency. When it is prepared and applied to organic electroluminescent devices, it achieves blue light emission under electroluminescence conditions. It is a high-performance organic light-emitting functional material and is expected to be promoted for commercial application.

[0593] 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.

[0594] Obviously, the above embodiments are merely illustrative examples for clear explanation 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. It is neither necessary nor possible to exhaustively list all possible implementations here. However, obvious variations or modifications derived therefrom are still within the scope of protection of this invention.

Claims

1. A compound of general formula having the structure shown in formula (1): In formula (1): X 1 and X 2 Each is independently designated as NR1, and each R1 is independently connected to an adjacent ring A or ring B to form a ring or not connected to form a ring. When connected to form a ring, it is bonded to an adjacent benzene ring through a single bond. R1 is selected from phenyl; Ring A and ring B are each independently selected from the benzene ring; R 12 R 13 Each group is independently selected from hydrogen, benzonitrile, trifluoromethyl, or one of the following groups, and R 12 R 13 Not both hydrogen: Furthermore, when the R 12 R 13 When both are selected from pyridyl or both are selected from phenyl-substituted triazine, R 11 It is hydrogen or related to R 12 R 13 same; When the R 12 With R 13 When one of the groups is selected from the following groups, and the other is hydrogen, R 11 For hydrogen: 。 2. A compound selected from the structures shown below: 。 3. The application of the compound according to claim 1 or 2, wherein the application is as a functional material in an organic electronic device, the organic electronic device being selected from organic electroluminescent devices, optical sensors, solar cells, lighting elements, organic thin-film transistors, organic field-effect transistors, information tags, electronic artificial skin sheets, sheet-type scanners, or electronic paper; The compound is used as a light-emitting layer material in organic electroluminescent devices, and as a light-emitting dye in the light-emitting layer.

4. An organic electroluminescent device, comprising a first electrode, a second electrode, and one or more light-emitting functional layers inserted between the first electrode and the second electrode, wherein the light-emitting functional layer comprises an electron blocking layer and at least one of a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer, and the light-emitting layer contains the compound of claim 1 or 2.

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