Organic compounds, mixtures, compositions and organic electronic devices

Abstract

The present application discloses an organic compound and a mixture, a composition and an organic electronic device comprising the organic compound. The organic compound has a structure as shown in the general formula (1): The organic compound is used in an organic electronic device, in particular, as a light-emitting material in a light-emitting layer of an organic electronic device to improve the efficiency and life of the organic electronic device.

Description

Technical Field

[0001] The present application relates to the technical field of luminescent materials, and in particular to an organic compound, and a mixture, a composition and an organic electronic device comprising the organic compound. Background Art

[0002] Organic semiconductor materials are diverse in synthesis, relatively low in manufacturing cost, and have excellent optical and electrical properties. Organic light-emitting diodes (OLEDs) have broad development potential due to their wide viewing angle, fast response time, low operating voltage, and thin panel thickness in the application of optoelectronic devices (such as flat panel displays and lighting).

[0003] In order to improve the luminous efficiency of organic light-emitting diodes, various fluorescent and phosphorescent luminescent material systems have been developed. Among them, organic light-emitting diodes using fluorescent materials have the characteristics of high reliability, but their internal electroluminescence quantum efficiency will be limited to 25% under electrical excitation, because the branching ratio of the singlet excited state and triplet excited state of the exciton is 1:3. Organic light-emitting diodes using phosphorescent materials have achieved an internal electroluminescence quantum efficiency of almost 100%, but phosphorescent OLEDs will also produce a Roll-off effect, that is, the luminous efficiency decreases rapidly with the increase of current or brightness, which is particularly unfavorable for high-brightness applications.

[0004] So far, the traditional phosphorescent materials with practical use value are metal complexes containing iridium and platinum. However, such raw materials are rare and expensive, and the synthesis of metal complexes is complicated, resulting in high costs. In order to overcome the above problems, Adachi proposed the concept of reverse internal conversion, that is, using organic compounds instead of metal complexes as light-emitting materials, which can achieve high efficiency comparable to phosphorescent OLEDs. This concept has been realized through various material combinations, such as composite excited state materials, thermally excited delayed fluorescence (TADF) materials, etc.

[0005] However, the performance of traditional blue light TADF materials still has a certain gap compared with phosphorescent materials in terms of efficiency and lifespan. Summary of the invention

[0006] In view of this, the present application provides an organic compound as a new type of luminescent material, which is used in organic electronic devices to improve the problems of low luminescence efficiency and short life of organic electronic devices.

[0007] The technical solution of this application is as follows:

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

[0009]

[0010] in:

[0011] R1 and R2 are each independently selected from: -H, -D, linear alkyl having 1 to 20 C atoms, linear alkoxy having 1 to 20 C atoms, linear thioalkoxy having 1 to 20 C atoms, branched or cyclic alkyl having 3 to 20 C atoms, branched or cyclic alkoxy having 3 to 20 C atoms, branched or cyclic thioalkoxy having 3 to 20 C atoms, silyl, keto having 1 to 20 C atoms, alkoxycarbonyl having 2 to 20 C atoms, aryloxycarbonyl having 7 to 20 C atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, amine, -CF3, -Cl, -Br, -F, -I, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aromatic group having 6 to 30 ring atoms, substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, substituted or unsubstituted aryloxy group having 6 to 30 ring atoms, substituted or unsubstituted heteroaryloxy group having 5 to 30 ring atoms, or a combination of these groups;

[0012] M1 and M2 are independently selected from the structure represented by formula (A-1) or (A-2):

[0013]

[0014] Ar1, Ar2, Ar3, Ar4 are independently selected from: substituted or unsubstituted aromatic groups having 6 to 30 C atoms, or substituted or unsubstituted heteroaromatic groups having 5 to 30 ring atoms;

[0015] * indicates the attachment site.

[0016] Correspondingly, the present application also provides a mixture, comprising the above-mentioned organic compound and at least one organic functional material, wherein the organic functional material is selected from hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, luminescent guest materials, luminescent host materials or organic dyes.

[0017] Correspondingly, the present application also provides a composition, comprising the above organic compound or the above mixture, and at least one organic solvent.

[0018] Correspondingly, the present application also provides an organic electronic device, comprising at least one organic functional layer, wherein the organic functional layer comprises the above-mentioned organic compound or the above-mentioned mixture, or the organic functional layer is prepared from the above-mentioned composition.

[0019] Compared with the prior art, the organic compound of the present application has the following beneficial effects:

[0020] The organic compound described in the present application is connected to silicon through two boron nitrogen compounds, so that the overall molecular structure has better conjugation and planarity, thereby improving the rigidity and stability of the organic compound molecule, thereby achieving the purpose of extending the luminous efficiency and service life of the device. In addition, the boron-silicon-boron organic compound described in the present application can be used as a blue light guest material, and by cooperating with the host material, it can effectively improve the luminous efficiency and service life of the electroluminescent device. BRIEF DESCRIPTION OF THE DRAWINGS

[0021] In order to more clearly illustrate the technical solutions in the embodiments of the present application, the drawings required for use in the description of the embodiments will be briefly introduced below. Obviously, the drawings described below are only some embodiments of the present application. For those skilled in the art, other drawings can be obtained based on these drawings without paying any creative work.

[0022] Figure 1 It is a schematic diagram of the structure of an organic electronic device provided in an embodiment of the present application. DETAILED DESCRIPTION

[0023] The following will be combined with the drawings in the embodiments of the present application to clearly and completely describe the technical solutions in the embodiments of the present application. Obviously, the described embodiments are only part of the embodiments of the present application, not all of the embodiments. Based on the embodiments in the present application, all other embodiments obtained by those skilled in the art without creative work belong to the scope of protection of the present application. In addition, it should be understood that the specific implementation methods described herein are only used to illustrate and explain the present application, and are not used to limit the present application. In the present application, unless otherwise specified, the directional words such as "upper" and "lower" used generally refer to the upper and lower parts of the device in actual use or working state, specifically the drawing direction in the accompanying drawings. In addition, in the description of the present application, the term "including" means "including but not limited to", the term "multiple" means "two or more", and the term "and / or" includes any and all combinations of one or more related listed items. Various embodiments of the present application may exist in the form of a range; it should be understood that the description in the form of a range is only for convenience and simplicity, and should not be understood as a hard limit to the scope of the present application; therefore, it should be considered that the range description has specifically disclosed all possible sub-ranges and single values ​​within the range. For example, description of a range from 1 to 6 should be considered to have specifically disclosed sub-ranges, such as from 1 to 3, from 1 to 4, from 1 to 5, from 2 to 4, from 2 to 6, from 3 to 6, etc., as well as single numbers within the stated range, such as 1, 2, 3, 4, 5, and 6, regardless of the range. In addition, whenever a numerical range is indicated herein, it is meant to include any cited numeral (fractional or integral) within the stated range.

[0024] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as those generally understood by those skilled in the art of the present invention. The terms used herein in the specification of the present application are only for the purpose of describing specific embodiments and are not intended to limit the present invention. The term "and / or" used herein includes any and all combinations of one or more related listed items.

[0025] In this application, composition and printing ink, or ink have the same meaning and can be interchanged.

[0026] In the present application, aromatic group, aromatic series and aromatic ring system have the same meaning and can be interchanged.

[0027] In the present application, heteroaromatic group, heteroaromatic series and heteroaromatic ring system have the same meaning and can be interchanged.

[0028] In the present application, "substituted" means that a hydrogen atom in a substituted group is replaced by a substituent.

[0029] In the present application, when the same substituent appears multiple times, it can be independently selected from different groups. If the general formula contains multiple R, then R can be independently selected from different groups.

[0030] In the present application, "substituted or unsubstituted" means that the defined group may be substituted or unsubstituted. When the defined group is substituted, it should be understood that the defined group may be substituted by one or more substituents R, wherein R is selected from but not limited to: deuterium atom, cyano, isocyano, nitro or halogen, alkyl containing 1-20 C atoms, heterocyclic group containing 3-20 ring atoms, aromatic group containing 6-20 ring atoms, heteroaromatic group containing 5-20 ring atoms, -NR'R", silane, carbonyl, alkoxycarbonyl, aryloxycarbonyl, carbamoyl, haloformyl, formyl, isocyanate, thiocyanate, isothiocyanate, hydroxyl, trifluoromethyl, and the above groups may be further substituted by substituents acceptable in the art; it is understandable that R' and R" in -NR'R" are independently selected from but not limited to: H, deuterium atom ... Preferably, R is selected from but not limited to: deuterium atom, cyano group, isocyano group, nitro group or halogen, alkyl group containing 1-10 C atoms, heterocyclic group containing 3-20 ring atoms, aromatic group containing 6-20 ring atoms, heteroaromatic group containing 5-20 ring atoms, silane group, carbonyl group, alkoxycarbonyl group, aryloxycarbonyl group, carbamoyl group, haloformyl group, formyl group, isocyanate group, thiocyanate group, isothiocyanate group, hydroxyl group, trifluoromethyl group, and the above groups may be further substituted by substituents acceptable in the art.

[0031] In the present application, the "number of ring atoms" refers to the number of atoms in the atoms constituting the ring itself of a structural compound (e.g., a monocyclic compound, a condensed ring compound, a cross-linked compound, a carbocyclic compound, a heterocyclic compound) formed by atoms bonding to form a ring. When the ring is substituted by a substituent, the atoms contained in the substituent are not included in the ring atoms. The same is true for the "number of ring atoms" described below unless otherwise specified. For example, the number of ring atoms of a benzene ring is 6, the number of ring atoms of a naphthalene ring is 10, and the number of ring atoms of a thienyl group is 5.

[0032] "Aryl or aromatic group" refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removing a hydrogen atom, which may be a monocyclic aromatic group, a condensed aromatic group, or a polycyclic aromatic group. For a polycyclic ring, at least one is an aromatic ring system. For example, "substituted or unsubstituted aromatic group having 6 to 40 ring atoms" refers to an aromatic group containing 6 to 40 ring atoms, preferably a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, more preferably a substituted or unsubstituted aromatic group having 6 to 18 ring atoms, and particularly preferably a substituted or unsubstituted aromatic group having 6 to 14 ring atoms, and the aromatic group may be further substituted; suitable examples include, but are not limited to, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, fluoranthenyl, triphenylene, pyrenyl, perylene, naphthylene, fluorenyl, dinaphthylenyl, acenaphthene and derivatives thereof. It is understandable that multiple aromatic groups may also be interrupted by short non-aromatic units (e.g. <10% non-H atoms, such as C, N or O atoms), specifically acenaphthene, fluorene, or 9,9-diarylfluorene, triarylamine, diaryl ether systems should also be included in the definition of aromatic groups.

[0033] "Heteroaryl or heteroaromatic group" means that at least one carbon atom is replaced by a non-carbon atom on the basis of an aryl group, and the non-carbon atom can be an N atom, an O atom, an S atom, etc. For example, "substituted or unsubstituted heteroaryl having 5 to 40 ring atoms" means a heteroaryl having 5 to 40 ring atoms, preferably a substituted or unsubstituted heteroaryl having 6 to 30 ring atoms, more preferably a substituted or unsubstituted heteroaryl having 6 to 18 ring atoms, and particularly preferably a substituted or unsubstituted heteroaryl having 6 to 14 ring atoms, and the heteroaryl group is optionally further substituted, and suitable examples include but are not limited to: thienyl, furanyl, pyrrolyl, oxadiazolyl, triazolyl, imidazolyl, pyridyl, bipyridyl, pyrimidyl, Triazine, acridinyl, pyridazinyl, pyrazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, benzothiophenyl, benzofuranyl, indolyl, pyrroloimidazolyl, pyrrolopyrrolyl, thienopyrrolyl, thienothiphenyl, furopyrrolyl, furofuranyl, thienofuranyl, benzisoxazolyl, benzisothiazolyl, benzimidazolyl, o-naphthyl, phenanthridinyl, primary pyridyl, quinazolinone, dibenzothiophenyl, dibenzofuranyl, carbazolyl and derivatives thereof.

[0034] In the present application, "alkyl" may refer to a linear, branched and / or cyclic alkyl group. The carbon number of the alkyl group may be 1 to 50, 1 to 30, 1 to 20, 1 to 10 or 1 to 6. Phrases containing this term, such as "C 1-9"Alkyl" refers to an alkyl group containing 1 to 9 carbon atoms, and each occurrence may be independently C1 alkyl, C2 alkyl, C3 alkyl, C4 alkyl, C5 alkyl, C6 alkyl, C7 alkyl, C8 alkyl or C9 alkyl. Non-limiting examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl 2-Hexyldecyl, 2-octyldecyl, 2-undecyl, 2-ethyldecyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl, 2-undecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, 2-tridecyl, 2-tetradecyl, 2-pentadecyl, 2-hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, 2-heptadecyl, 2-octylhexadecyl, 2-octadecyl, 2-octadecyl, 2-nonadecyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexyleicosyl, 2-octyleicosyl, 2-heneicosyl, 2-heneicosyl, 2-heconicosyl, 2-docosyl, 2-tricosyl, 2-tetracosyl, 2-pentacosyl, 2-hexacosyl, 2-heptacosyl, 2-octacosyl, 2-nonacosyl, 2-triacontyl, etc.

[0035] In the present application, the substituent abbreviations correspond to: n-normal, sec-secondary, i-iso, t-tertiary, o-ortho, m-meta, p-para, Me methyl, Et ethyl, Pr propyl, Bu butyl, Am n-pentyl, Hx hexyl, Cy cyclohexyl.

[0036] In the present application, the silyl group may be represented by the chemical formula -Si(Y101)(Y102)(Y103), and Y101, Y102, and Y103 may each be hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, or a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. Examples of the silyl group include trialkylsilyl groups and triarylsilyl groups, and specific examples thereof include trimethylsilyl groups, triethylsilyl groups, tert-butyldimethylsilyl groups, vinyldimethylsilyl groups, propyldimethylsilyl groups, triphenylsilyl groups, diphenylsilyl groups, phenylsilyl groups, and the like, but examples are not limited thereto.

[0037] "Amine" refers to an amine derivative having the structural features of the formula -N(X)2, wherein each "X" is independently H, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclyl, etc. Non-limiting types of amines include -NH2, -N(alkyl), -NH(alkyl), -N(cycloalkyl), -NH(cycloalkyl), -N(heterocyclyl), -NH(heterocyclyl), -N(aryl), -NH(aryl), -N(alkyl)(aryl), -N(alkyl)(heterocyclyl), -N(cycloalkyl)(heterocyclyl), -N(aryl)(heteroaryl), -N(alkyl)(heteroaryl), etc.

[0038] In the present application, unless otherwise defined, hydroxyl refers to -OH, carboxyl refers to -COOH, carbonyl refers to -C(=O)-, amino refers to -NH2, formyl refers to -C(=O)H, haloformyl refers to -C(=O)Z (wherein Z represents halogen), carbamoyl refers to -C(=O)NH2, isocyanate refers to -NCO, and isothiocyanate refers to -NCS.

[0039] The term "alkoxy" refers to a group having a structure of "-O-alkyl", i.e., an alkyl group as defined above is connected to other groups via an oxygen atom. Phrases containing the term, suitable examples include, but are not limited to, methoxy (-O-CH or -OMe), ethoxy (-O-CHCH or -OEt) and tert-butoxy (-OC(CH) or -OtBu).

[0040] In this application, "*" connected to a single bond indicates a site of attachment or fusion;

[0041] In the present application, when a linking site is not specified in a group, it means that an optional linking site in the group can be used as a linking site;

[0042] In the present application, when the fusion site is not specified in the group, it means that any fusion site in the group can be used as the fusion site, and preferably two or more sites in the ortho position in the group are fusion sites;

[0043] In the present application, when a group contains multiple substituents with the same symbol, the substituents may be the same or different from each other, for example The six Rs on the benzene ring may be the same as or different from each other.

[0044] In the present application, the single bond to which the substituent is attached runs through the corresponding ring, indicating that the substituent can be attached to any position of the ring, for example In which R is connected to any substitutable position of the benzene ring, such as express Can be used with The above optional substitutable positions form a ring.

[0045] In the present application, "adjacent groups" means that there is no substitutable site between two substituents.

[0046] In the present application, "two adjacent Rs form a ring" means a ring system formed by two adjacent Rs connected to each other, and the ring system can be selected from aliphatic hydrocarbon rings, aliphatic heterocycles, aromatic hydrocarbon rings or aromatic heterocycles. Preferably, a substituted or unsubstituted aromatic group or heteroaromatic group with 5-10 ring atoms can be formed; more preferably, a substituted or unsubstituted aromatic group or heteroaromatic group with 6 ring atoms can be formed. Preferably,

[0047] The terms "combination thereof", "any combination thereof", "any combination thereof", "combination" and the like used in the present application include all suitable combinations of any two or more items in the listed groups.

[0048] In the present application, “further”, “furthermore”, “particularly”, etc. are used for descriptive purposes to indicate differences in content, but should not be construed as limiting the scope of protection of the present invention.

[0049] In this application, "optionally", "optional", and "optional" mean optional, that is, any one of the two parallel schemes of "yes" or "no". If there are multiple "options" in a technical solution, unless otherwise specified and there is no contradiction or mutual restriction, each "option" is independent.

[0050] In the present application, the technical features described in an open manner include closed technical solutions composed of the listed features, and also include open technical solutions containing the listed features.

[0051] An organic compound having a structure as shown in the general formula (1):

[0052]

[0053] in:

[0054] R1 and R2 are each independently selected from: -H, -D, linear alkyl having 1 to 20 C atoms, linear alkoxy having 1 to 20 C atoms, linear thioalkoxy having 1 to 20 C atoms, branched or cyclic alkyl having 3 to 20 C atoms, branched or cyclic alkoxy having 3 to 20 C atoms, branched or cyclic thioalkoxy having 3 to 20 C atoms, silyl, keto having 1 to 20 C atoms, alkoxycarbonyl having 2 to 20 C atoms, aryloxycarbonyl having 7 to 20 C atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, amine, -CF3, -Cl, -Br, -F, -I, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aromatic group having 6 to 30 ring atoms, substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, substituted or unsubstituted aryloxy group having 6 to 30 ring atoms, substituted or unsubstituted heteroaryloxy group having 5 to 30 ring atoms, or a combination of these groups;

[0055] M1 and M2 are independently selected from the structure represented by formula (A-1) or (A-2):

[0056]

[0057] Ar1, Ar2, Ar3, Ar4 are independently selected from: substituted or unsubstituted aromatic groups having 6 to 30 C atoms, or substituted or unsubstituted heteroaromatic groups having 5 to 30 ring atoms;

[0058] * indicates the attachment site.

[0059] In some embodiments, the structure of the organic compound is selected from any one of the structures shown in general formulas (2-1) to (2-4):

[0060]

[0061] In some embodiments, Ar1, Ar2, Ar3, and Ar4 are independently selected from: substituted or unsubstituted aromatic groups having 6 to 20 carbon atoms, or substituted or unsubstituted heteroaromatic groups having 5 to 20 ring atoms. Further, Ar1, Ar2, Ar3, and Ar4 are independently selected from: substituted or unsubstituted aromatic groups having 6 to 13 carbon atoms, or substituted or unsubstituted heteroaromatic groups having 5 to 13 ring atoms.

[0062] In a specific example, each time Ar1, Ar2, Ar3, and Ar4 appear, they are independently selected from any one or any combination of the structures shown in formula (B-1) to (B-6):

[0063]

[0064] in:

[0065] Each occurrence of X is independently selected from N or CR3;

[0066] Each occurrence of Y is independently selected from CR4R5, SiR4R5, NR6, PR6, C=O, S or O;

[0067] Each occurrence of R3, R4, R5, and R6 is independently selected from the group consisting of: -H, -D, straight-chain alkyl having 1 to 20 C atoms, straight-chain alkoxy having 1 to 20 C atoms, straight-chain thioalkoxy having 1 to 20 C atoms, branched or cyclic alkyl having 3 to 20 C atoms, branched or cyclic alkoxy having 3 to 20 C atoms, branched or cyclic thioalkoxy having 3 to 20 C atoms, silyl, keto having 1 to 20 C atoms, alkoxycarbonyl having 2 to 20 C atoms, , aryloxycarbonyl, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxy, nitro, amine, -CF3, -Cl, -Br, -F, substituted or unsubstituted aromatic groups having 6 to 20 C atoms, substituted or unsubstituted heteroaromatic groups having 5 to 20 ring atoms, substituted or unsubstituted aryloxy groups having 6 to 20 ring atoms, substituted or unsubstituted heteroaryloxy groups having 5 to 20 ring atoms, or combinations of these groups.

[0068] In some embodiments, each occurrence of Ar2 and Ar3 is independently selected from the following groups:

[0069]

[0070] Where: * indicates the fusion site.

[0071] In some embodiments, the structure represented by formula (A-1) is selected from one of the structures represented by formula (C-1) to (C-16):

[0072] In some embodiments, the structure represented by formula (A-2) is selected from one of the structures represented by formula (D-1) to (D-17):

[0073]

[0074]

[0075] In some embodiments, the structure of the organic compound is selected from any one of the structures shown in general formulas (3-1) to (3-14):

[0076]

[0077]

[0078] In one embodiment, each occurrence of Ar1 and Ar4 is independently selected from the following groups:

[0079]

[0080] Wherein: * indicates the connection site.

[0081] In one embodiment, X is independently selected from N or CR3 at each occurrence; R3 is independently selected from -H, -D, a linear alkyl group having 1 to 10 C atoms, a branched or cyclic alkyl group having 3 to 10 C atoms, a substituted or unsubstituted aromatic group having 6 to 10 C atoms, a substituted or unsubstituted heteroaromatic group having 5 to 10 ring atoms, or a combination of these groups; specifically, R3 is independently selected from -H, -D, methyl, Et, tBu, iPr, tAm, or phenyl at each occurrence, or a combination of these groups.

[0082] In one embodiment, each occurrence of Y is independently selected from NR6, S or O.

[0083] Each time R6 appears, it is independently selected from: -H, -D, a straight-chain alkyl group having 1 to 10 C atoms, a branched or cyclic alkyl group having 3 to 10 C atoms, a substituted or unsubstituted aromatic group having 6 to 10 C atoms, a substituted or unsubstituted heteroaromatic group having 5 to 10 ring atoms, or a combination of these groups; specifically, each time R6 appears, it is independently selected from: -H, -D, methyl, Et, tBu, iPr, tAm, or phenyl, or a combination of these groups.

[0084] In one embodiment, each occurrence of R1 and R2 is independently selected from: -H, -D, a straight-chain alkyl group having 1 to 10 C atoms, a branched or cyclic alkyl group having 3 to 10 C atoms, a substituted or unsubstituted aromatic group having 6 to 10 C atoms, a substituted or unsubstituted heteroaromatic group having 5 to 10 ring atoms, or a combination of these groups; specifically, each occurrence of R1 and R2 is independently selected from: -H, -D, methyl, Et, tBu, iPr, tAm, or phenyl, or a combination of these groups.

[0085] As an example, in some embodiments, the organic compound of the present application can be selected from but not limited to any one of the following structures:

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092] It can be understood that the H in the structural formula of the above organic compound can be further substituted.

[0093] In some embodiments, the organic compound of the present application can be used as an organic functional material in a functional layer of an organic electronic device, in particular, in a functional layer of an OLED device. The organic functional material can be, but is not limited to, a hole injection material (HIM), a hole transport material (HTM), an electron transport material (ETM), an electron injection material (EIM), an electron blocking material (EBM), a hole blocking material (HBM), a luminescent guest material (Emitter), a luminescent host material (Host Emitter) and an organic dye.

[0094] In some embodiments, the organic compound of the present application is used in a light-emitting layer. In at least one embodiment, the organic compound of the present application is used in a light-emitting layer as a guest material of the light-emitting layer.

[0095] In some embodiments, the organic compound of the present application is used as a blue light emitting material in a light emitting layer.

[0096] The present application further relates to a mixture, comprising at least one organic compound as described above and at least another organic functional material. The another organic functional material is selected from hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, luminescent guest materials (Emitter), luminescent host materials and organic dyes. Wherein, the luminophore is selected from singlet luminophores (fluorescent luminophores), triplet luminophores (phosphorescent luminophores) and organic thermally excited delayed fluorescence materials (TADF materials). Detailed descriptions of various organic functional materials are detailed in WO2010135519A1, US20090134784A1 and WO 2011110277A1, and the entire contents of these three patent documents are hereby incorporated herein by reference.

[0097] In one embodiment, the another organic functional material is selected from a host material; further, the another organic functional material is selected from a blue light host material.

[0098] The present application also relates to a composition comprising at least one organic compound or mixture as described above, and at least one organic solvent.

[0099] It will be appreciated that the composition may also be referred to as ink.

[0100] When used in the printing process, the viscosity and surface tension of the ink are important parameters. The surface tension parameters of the appropriate ink are suitable for a specific substrate and a specific printing method. In some embodiments, the surface tension of the ink according to the present application at working temperature or at 25°C ranges from 19 dyne / cm to 50 dyne / cm; better, 22 dyne / cm to 35 dyne / cm; and best, 25 dyne / cm to 33 dyne / cm. In some embodiments, the viscosity of the ink according to the present application at working temperature or at 25°C ranges from 1 cps to 100 cps; better, 1 cps to 50 cps; better, 1.5 cps to 20 cps; and best, 4.0 cps to 20 cps. The ink formulated in this way will be beneficial to inkjet printing.

[0101] The organic solvent is selected from at least one of aromatic or heteroaromatic based solvents, ester based solvents, aromatic ketone based solvents, aromatic ether based solvents, aliphatic ketones, aliphatic ethers, alicyclic compounds, olefin compounds, borate ester compounds and phosphate ester compounds.

[0102] In at least one embodiment, in the composition, the organic solvent is selected from aromatic or heteroaromatic solvents.

[0103] The aromatic or heteroaromatic based solvent may be selected from, but not limited to, p-diisopropylbenzene, pentylbenzene, tetralin, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, dipentylbenzene, tripentylbenzene, pentyltoluene, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, 1,2,3,4-tetramethylbenzene, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, butylbenzene, dodecylbenzene, dihexylbenzene, dibutylbenzene, p-diisopropylbenzene, cyclohexylbenzene, benzylbutylbenzene, dimethylnaphthalene, 3-isopropyl At least one of biphenyl, p-methylisopropylbenzene, 1-methylnaphthalene, 1,2,4-trichlorobenzene, 4,4-difluorodiphenylmethane, 1,2-dimethoxy-4-(1-propenyl)benzene, diphenylmethane, 2-phenylpyridine, 3-phenylpyridine, N-methyldiphenylamine, 4-isopropylbiphenyl, α,α-dichlorodiphenylmethane, 4-(3-phenylpropyl)pyridine, benzyl benzoate, 1,1-bis(3,4-dimethylphenyl)ethane, 2-isopropylnaphthalene, quinoline, isoquinoline, methyl 2-furoate and ethyl 2-furoate.

[0104] The ester-based solvent may be selected from, but not limited to, alkyl octanoate, alkyl sebacate, alkyl stearate, alkyl benzoate, alkyl phenylacetate, alkyl cinnamate, alkyl oxalate, alkyl maleate, alkyl lactone, alkyl oleate, etc. At least one of octyl octanoate, diethyl sebacate, diallyl phthalate, and isononyl isononanoate is particularly preferred.

[0105] The aromatic ketone-based solvent may be selected from, but not limited to, 1-tetralone, 2-tetralone, 2-(phenylepoxy)tetralone, 6-(methoxy)tetralone, acetophenone, propiophenone, benzophenone, and derivatives thereof. As an example, the derivative may be selected from, but not limited to, at least one of 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylpropiophenone, 3-methylpropiophenone, and 2-methylpropiophenone.

[0106] The aromatic ether-based solvent may be selected from, but is not limited to, at least one of 3-phenoxytoluene, butoxybenzene, p-anisaldehyde dimethyl acetal, tetrahydro-2-phenoxy-2H-pyran, 1,2-dimethoxy-4-(1-propenyl)benzene, 1,4-benzodioxane, 1,3-dipropylbenzene, 2,5-dimethoxytoluene, 4-ethyl ethyl ether, 1,3-dipropoxybenzene, 1,2,4-trimethoxybenzene, 4-(1-propenyl)-1,2-dimethoxybenzene, 1,3-dimethoxybenzene, glycidyl phenyl ether, dibenzyl ether, 4-tert-butylanisole, trans-p-propenylanisole, 1,2-dimethoxybenzene, 1-methoxynaphthalene, diphenyl ether, 2-phenoxymethyl ether, 2-phenoxytetrahydrofuran, and ethyl-2-naphthyl ether.

[0107] The aliphatic ketone-based solvent can be selected from, but not limited to, 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2,5-hexanedione, 2,6,8-trimethyl-4-nonanone, fenchone, phorone, isophorone, di-n-amyl ketone, etc.; or an aliphatic ether, for example, at least one of amyl ether, hexyl ether, dioctyl ether, ethylene glycol dibutyl ether, diethylene glycol diethyl ether, diethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, triethylene glycol ethyl methyl ether, triethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether and tetraethylene glycol dimethyl ether.

[0108] It is understood that the organic solvent may be used alone or as a mixed solvent of two or more organic solvents.

[0109] In some embodiments, the composition of the present application includes at least one organic compound or mixture as described above, and at least one organic solvent, and may further include another organic solvent.

[0110] The other organic solvent can be selected from but not limited to at least one of methanol, ethanol, 2-methoxyethanol, dichloromethane, chloroform, chlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1,4-dioxane, acetone, methyl ethyl ketone, 1,2-dichloroethane, 3-phenoxytoluene, 1,1,1-trichloroethane, 1,1,2,2-tetrachloroethane, ethyl acetate, butyl acetate, dimethylformamide, dimethylacetamide, dimethyl sulfoxide (DMSO), tetralin, decalin and indene.

[0111] In some embodiments, organic solvents suitable for the present application are solvents having a Hansen solubility parameter within the following ranges:

[0112] δd (dispersion force) is in the range of 17.0 to 23.2 MPa1 / 2, especially in the range of 18.5 to 21.0 MPa1 / 2;

[0113] δp (polar force) is in the range of 0.2 to 12.5 MPa1 / 2, especially in the range of 2.0 to 6.0 MPa1 / 2;

[0114] δh (hydrogen bonding force) is in the range of 0.9 to 14.2 MPa1 / 2, especially in the range of 2.0 to 6.0 MPa1 / 2.

[0115] In some embodiments, according to the composition of the present application, the boiling point of the organic solvent should be considered when selecting. In at least some embodiments, the boiling point of the organic solvent is ≥150°C; preferably ≥180°C; preferably ≥200°C; more preferably ≥250°C; and most preferably ≥300°C. Boiling points within these ranges are beneficial for preventing nozzle clogging of the inkjet print head.

[0116] It will be appreciated that the organic solvent may be evaporated from the solvent system to form a film comprising the organic compound.

[0117] In some embodiments, the composition is a solution. In some other embodiments, the composition is a suspension. The solution or suspension may further include additives for adjusting viscosity, adjusting film-forming properties, improving adhesion, etc. The additives may be selected from but not limited to at least one of a surfactant compound, a lubricant, a wetting agent, a dispersant, a hydrophobic agent, and an adhesive.

[0118] In the composition, the content of the organic compound or the mixture is 0.01 to 10 wt %, preferably 0.1 to 5 wt %, more preferably 0.2 to 5 wt %, and most preferably 0.25 to 3 wt %.

[0119] The present application also relates to the use of the composition as a coating or printing ink in the preparation of an organic electronic device. In some embodiments, the composition is used to prepare an organic electronic device by a printing or coating preparation method. The printing or coating preparation method can be, but is not limited to, inkjet printing, gravure printing, spray printing, letterpress printing, screen printing, dip coating, spin coating, blade coating, roller printing, twist roller printing, lithography, flexographic printing, rotary printing, spray coating, brush coating, pad printing, slit extrusion coating, etc. Preferred are gravure printing, spray printing and inkjet printing.

[0120] The present application also relates to an application of the organic compound, mixture or composition as described above in an organic electronic device. The specific scheme is as follows:

[0121] An organic electronic device comprises at least one organic functional layer, wherein the organic functional layer comprises at least one organic compound or mixture as described above, or the organic functional layer is prepared from the above composition.

[0122] Furthermore, the organic electronic device comprises a cathode, an anode and at least one organic functional layer. The organic functional layer comprises at least one organic compound or mixture as described above, or the organic functional layer is prepared from the above composition.

[0123] The organic functional layer may be, but is not limited to, a hole injection layer (HIL), a hole transport layer (HTL), an emitting layer (EML), an electron blocking layer, an electron injection layer (EIL), an electron transport layer (ETL) or a hole blocking layer (HBL). In at least one embodiment, the organic functional layer is an emitting layer.

[0124] The organic electronic device may be, but is not limited to, an organic light emitting diode (OLED), an organic photovoltaic cell (OPV), an organic light emitting cell (OLEEC), an organic field effect transistor (OFET), an organic light emitting field effect transistor, an organic laser, an organic spin electronic device, an organic sensor, and an organic plasmon emitting diode (Organic Plasmon Emitting Diode). Particularly preferred are organic electroluminescent devices such as OLED and organic light emitting field effect transistor. Further particularly preferred are OLEDs.

[0125] In one embodiment, the organic electronic device includes a substrate and an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer and a cathode sequentially stacked on the substrate. The light-emitting layer contains at least one organic compound or mixture as described above, or the light-emitting layer is prepared from the composition as described above. It is understood that the structure of the organic electronic device is not limited thereto.

[0126] The substrate may be transparent or opaque. The substrate may be rigid or elastic. The substrate may be plastic, metal, semiconductor wafer or glass. The substrate preferably has a smooth surface, and substrates without surface defects are particularly ideal. In one embodiment, the substrate is flexible, and its material may be selected from but not limited to polymer films or plastics, and its glass transition temperature Tg is above 150°C, preferably above 200°C, more preferably above 250°C, and preferably above 300°C. Examples of suitable flexible substrates include polyethylene terephthalate (PET) and polyethylene glycol (2,6-naphthalene) (PEN).

[0127] The anode is an electrode for injecting holes, and the anode can easily inject holes into the hole injection layer, or the hole transport layer, or the light-emitting layer. The anode may include a conductive metal, a conductive metal oxide, or a conductive polymer. In one embodiment, the absolute value of the difference between the work function of the anode and the HOMO energy level or valence band energy level of the light-emitting body in the light-emitting layer or the p-type semiconductor material as the HIL or HTL or the electron blocking layer (EBL) is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. Examples of anode materials include but are not limited to: Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO, aluminum-doped zinc oxide (AZO), etc. Other suitable anode materials are known and can be easily selected for use by ordinary technicians in this field. The anode material can be deposited using any suitable technology, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), etc. In some embodiments, the anode is patterned. Patterned ITO conductive substrates are commercially available and can be used to prepare devices according to the present application. The cathode is an electrode that injects electrons, and the cathode can easily inject electrons into the electron injection layer, or the electron transport layer, or the light-emitting layer. The cathode may comprise a conductive metal or a conductive metal oxide. In one embodiment, the absolute value of the difference between the work function of the cathode and the LUMO energy level or conduction band energy level of the luminophore in the light-emitting layer or the n-type semiconductor material as the electron injection layer (EIL) or the electron transport layer (ETL) or the hole blocking layer (HBL) is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. In principle, all materials that can be used as cathodes of organic electronic devices may be used as cathode materials of the device of the present application. Examples of cathode materials include but are not limited to: Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloy, BaF2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO, etc. The cathode material may be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), and the like.

[0128] The hole injection layer is a layer for promoting the injection of holes from the anode to the light-emitting layer, and the hole injection material is a material that can skillfully receive holes injected from the positive electrode at a low voltage, and preferably, the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include metal porphyrins, oligothiophenes, organic materials based on arylamines, organic materials based on hexanitrile hexaazatriphenylene, organic materials based on quinacridone, organic materials based on perylene, anthraquinone, polyaniline-based and polythiophene-based conductive polymers, etc., but are not limited thereto.

[0129] The hole transport layer can be used to smoothly transport holes. The hole transport material known in the art for the hole transport layer is suitably a material with high hole mobility, which can receive holes transmitted from the anode or the hole injection layer and transfer the holes to the light-emitting layer. Specific examples thereof include organic materials based on arylamines, organic materials based on carbazoles, conductive polymers, block copolymers having both conjugated and non-conjugated parts, etc., but are not limited thereto.

[0130] The electron blocking layer may be disposed between the hole transport layer and the light emitting layer. As the electron blocking layer, a spiroindoloacridine-based compound or a material known in the art may be used.

[0131] The electron transport layer can be used to smoothly transport electrons. The electron transport material is suitably a material with high electron mobility, which can skillfully receive electrons injected from the negative electrode and transfer the electrons to the light-emitting layer. Specific examples thereof may include, but are not limited to, at least one of an Al complex of 8-hydroxyquinoline, a complex containing Alq3, an organic free radical compound, a hydroxyflavone-metal complex, 8-hydroxyquinoline lithium (Liq), and a benzimidazole-based compound.

[0132] The electron injection layer can be used to smoothly inject electrons. The electron injection material is preferably: having the ability to transport electrons, having the effect of injecting electrons from the negative electrode, and having an excellent effect of injecting electrons into the light-emitting layer or the light-emitting material, preventing the excitons generated by the light-emitting layer from moving to the hole injection layer, and also having an excellent ability to form a thin film. Specific examples thereof include fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, azole, diazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenyl methane, anthrone, etc. and derivatives thereof, metal complex compounds, nitrogen-containing 5-membered ring derivatives, etc., but are not limited thereto.

[0133] It is understood that the organic electronic device may further include a hole blocking layer between the light-emitting layer and the electron transport layer, the hole blocking layer being a layer that blocks holes from reaching the negative electrode, and may generally be formed under the same conditions as those of the hole injection layer. Specific examples thereof include diazole derivatives or triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, etc., but are not limited thereto.

[0134] The light emitting wavelength of the organic electronic device is between 300 and 1000 nm, preferably between 350 and 900 nm, and more preferably between 400 and 800 nm.

[0135] In one embodiment, the organic electronic device described in the present application is a solution-type organic electronic device, and one or more functional layers thereof are prepared by printing; further, the solution-type organic electronic device is a solution-type OLED.

[0136] The present invention also relates to the application of the organic electronic device according to the present invention in various electronic devices, which may be, but are not limited to, display devices, lighting devices, light sources, sensors, and the like.

[0137] The present application also relates to an electronic device comprising the organic electronic device, which may be, but is not limited to, a display device, a lighting device, a light source, a sensor, and the like.

[0138] The present application is described in detail below through specific embodiments. The following embodiments are only partial embodiments of the present application and are not limitations of the present application. Specific embodiments

[0140] Example 1

[0141] The synthetic route of organic compound 1 in this example is as follows:

[0142]

[0143] Synthesis of intermediate 1-3:

[0144] Under nitrogen atmosphere, in a dry three-necked flask, 20 mmol of compound 1-1, 10 mmol of compound 1-2, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine and 1.38 g of potassium carbonate were added respectively, and 150 ml of toluene was added to dissolve it, and the reaction solution was heated to 80°C until it refluxed. The reaction was reacted for 12 hours. When the reaction was complete, water was added to quench the reaction, and the organic phase was extracted with dichloromethane (DCM). The organic phases washed multiple times were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated to dryness to obtain a crude product, which was purified by flash column chromatography to obtain intermediate 1-3 with a molar weight of 8.73 mmol and a yield of 87.3%. MS (ASAP) = 446.5.

[0145] Synthesis of intermediate 1-4:

[0146] Add 10mmol intermediate 1-3 and 100ml dry tert-butylbenzene to a 250ml three-necked flask, cool to -30°C in a N2 atmosphere, and add (30.6mmol) t-BuLi n-hexane solution dropwise. Raise the temperature to 60°C, react for 2 hours, and remove the n-hexane solvent under reduced pressure. Cool the reaction solution to -30°C again, add 10.5mmol boron tribromide solution, stir at room temperature for 0.5 hours, then cool the reaction solution to 0°C, add 21mmol N, N-diisopropylethylamine, wait for the addition to be completed, heat to room temperature and stir, then continue to heat to 120°C and stir for 3 hours, and cool the reaction solution to room temperature. Add sodium carbonate aqueous solution and ethyl acetate to quench the reaction. Extract the aqueous phase with ethyl acetate and combine the organic phases, evaporate the solvent to obtain a crude product, and purify with a rapid silica gel column to obtain a pure product. Recrystallization with toluene and ethyl acetate gave intermediate 1-4 with a molar weight of 7.83 mmol, a reaction yield of 78.3%, and MS (ASAP) = 420.3.

[0147] Synthesis of intermediate 1-5:

[0148] Under nitrogen atmosphere, in a dry three-necked flask, 10 mmol of intermediate 1-4 and 5 mmol of liquid bromine were added respectively, and 150 ml of concentrated sulfuric acid was added to dissolve them, and the reaction solution was heated to 80°C until refluxed. The reaction was reacted for 12 hours. When the reaction was complete, water was added to quench the reaction. At the same time, the organic phase was extracted with dichloromethane for multiple times, and the organic phases washed multiple times were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated to dryness to obtain a crude product, which was purified by flash column chromatography to obtain intermediate 1-5 with a molar weight of 9.02 mmol and a yield of 90.2%. MS (ASAP) = 498.4.

[0149] Synthesis of organic compound 1:

[0150] Prepare a dry 500mL three-necked flask, set up the reaction device, evacuate and pass nitrogen; keep nitrogen flowing in the reaction flask, weigh 20mmol of intermediate 1-5, add THF (tetrahydrofuran, 250ml), evacuate and pass nitrogen for three cycles, and cool to -78°C; slowly drop 20mmol of n-butyl lithium solution into the reaction flask, react at -78°C for 30min, and quickly add 10mmol of dimethoxydiphenylsilane (compound 1-6). Let the reaction system slowly rise to room temperature and react for 12h. Add water, extract with DCM, spin dry the solvent, and use column chromatography (eluent is PE) to obtain a yellow-green solid, i.e., organic compound 1, with a yield of 43.4%, MS (ASAP) = 1020.6.

[0151] Example 2

[0152] The synthetic route of organic compound 2 in this example is as follows:

[0153]

[0154] Synthesis of intermediate 2-2:

[0155] Under nitrogen atmosphere, in a dry three-necked flask, 20 mmol of compound 1-1 and 10 mmol of compound 2-1, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine and 1.38 g of potassium carbonate were added respectively, and 150 ml of toluene was added to dissolve it, and the reaction solution was heated to 80°C until it refluxed. The reaction was reacted for 12 hours. When the reaction was complete, water was added to quench the reaction, and the organic phase was extracted with dichloromethane for multiple times. The organic phases washed multiple times were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated to dryness to obtain a crude product, which was purified by flash column chromatography to obtain intermediate 2-2 with a molar weight of 8.33 mmol and a yield of 83.3%. MS (ASAP) = 524.5.

[0156] Synthesis of intermediate 2-3:

[0157] Add 10mmol intermediate 2-2 and 100ml dry tert-butylbenzene to a 250ml three-necked flask, cool to -30°C in a N2 atmosphere, and add (10mmol) n-BuLi n-hexane solution dropwise. Raise the temperature to 60°C, react for 2 hours, and remove the n-hexane solvent under reduced pressure. Cool the reaction solution to -30°C again, add 10.5mmol boron tribromide solution, stir at room temperature for 0.5 hours, then cool the reaction solution to 0°C, add 21mmol N, N-diisopropylethylamine, wait for the addition to be completed, heat to room temperature and stir, then continue to heat to 120°C and stir for 3 hours, and cool the reaction solution to room temperature. Add sodium carbonate aqueous solution and ethyl acetate to quench the reaction. Extract the aqueous phase with ethyl acetate and combine the organic phases, evaporate the solvent to obtain a crude product, and purify with a rapid silica gel column to obtain a pure product. Recrystallization with toluene and ethyl acetate gave intermediate 2-3 with a molar weight of 7.53 mmol, a reaction yield of 75.3%, and MS (ASAP) = 454.3.

[0158] Synthesis of intermediate 2-5:

[0159] Under nitrogen atmosphere, in a dry three-necked flask, 10 mmol of intermediate 2-3 and 10 mmol of compound 2-4 were added to a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (tetrakis(triphenylphosphine)palladium, 0.1 mmol) and potassium carbonate (30 mmol) were added. Stir at 100°C for 6 h under nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the separated liquid was extracted and washed with water. The organic phase was collected, dried, concentrated under reduced pressure, column chromatographed and recrystallized to obtain intermediate 2-5, with a molar weight of 8.21 mmol, a yield of 82.1%, and MS (ASAP) = 530.3.

[0160] Synthesis of intermediate 2-6:

[0161] Prepare a dry 500mL three-necked flask, set up the reaction device, evacuate and pass nitrogen; keep nitrogen flowing in the reaction flask, weigh 10mmol of intermediate 2-5, add THF (250ml), evacuate and pass nitrogen for three cycles, and cool to -78°C; slowly drop 10mmol of tert-butyl lithium solution into the reaction flask, react at -78°C for 30min, and quickly add 10mmol of dimethoxydiphenylsilane (compound 1-6). Let the reaction system slowly rise to room temperature and react for 12h. Add water, extract with DCM, spin dry the solvent, and purify with rapid column chromatography to obtain intermediate 2-6, with a molar weight of 7.45mmol, a yield of 74.5%, and MS (ASAP) = 708.5.

[0162] Synthesis of organic compound 2:

[0163] Prepare a dry 500mL three-necked flask, set up the reaction device, evacuate and pass nitrogen; keep nitrogen flowing in the reaction flask, weigh 10mmol of intermediate 1-5, add THF (250ml), evacuate and pass nitrogen for three cycles, and cool to -78°C; slowly drop 10mmol of n-butyl lithium solution into the reaction flask, react at -78°C for 30min, and quickly add 10mmol of intermediate 2-6. Let the reaction system slowly rise to room temperature and react for 12h. Add water, extract with DCM, spin dry the solvent, and use column chromatography (eluent is PE) to obtain a yellow-green solid, that is, organic compound 2, with a yield of 37.3%, MS (ASAP) = 1096.7.

[0164] Example 3

[0165] The synthetic route of organic compound 3 in this example is as follows:

[0166]

[0167] Synthesis of organic compound 3:

[0168] Prepare a dry 500mL three-necked flask, set up the reaction device, evacuate and pass nitrogen; keep nitrogen flowing in the reaction flask, weigh 20mmol of intermediate 2-5, add THF (250ml), evacuate and pass nitrogen for three cycles, and cool to -78°C; slowly drop 10mmol of tert-butyl lithium solution into the reaction flask, react at -78°C for 30min, and quickly add 10mmol of dimethoxydiphenylsilane (compound 1-6). Let the reaction system slowly rise to room temperature and react for 12h. Add water, extract with DCM, spin dry the solvent, and use column chromatography (eluent is PE) to obtain a yellow-green solid, i.e., organic compound 3, with a yield of 32.4%, MS (ASAP) = 1172.6.

[0169] Example 4

[0170] The synthetic route of organic compound 4 in this example is as follows:

[0171]

[0172] Synthesis of intermediate 4-2:

[0173] Under nitrogen atmosphere, in a dry three-necked flask, 10 mmol of intermediate 2-3 and 10 mmol of compound 4-1 were added to a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. Stir at 100°C for 6 h under nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was collected, dried, concentrated under reduced pressure, column chromatographed and recrystallized to obtain intermediate 4-2, with a molar weight of 7.89 mmol, a yield of 78.9%, and MS (ASAP) = 530.4.

[0174] Synthesis of organic compound 4:

[0175] Prepare a dry 500mL three-necked flask, set up the reaction device, evacuate and pass nitrogen; keep nitrogen flowing in the reaction flask, weigh 20mmol of intermediate 4-2, add THF (250ml), evacuate and pass nitrogen for three cycles, and cool to -78°C; slowly drop 10mmol of tert-butyl lithium solution into the reaction flask, react at -78°C for 30min, and quickly add 10mmol of dimethoxydiphenylsilane (compound 1-6). Let the reaction system slowly rise to room temperature and react for 12h. Add water, extract with DCM, spin dry the solvent, and use column chromatography (eluent is PE) to obtain a yellow-green solid, i.e., organic compound 4, with a yield of 39.4%, MS (ASAP) = 1172.7.

[0176] Example 5

[0177] The synthetic route of organic compound 5 in this example is as follows:

[0178]

[0179] Synthesis of intermediate 5-1:

[0180] Under nitrogen atmosphere, in a dry three-necked flask, 10 mmol of compound 1-1 and 10 mmol of compound 1-2, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine and 1.38 g of potassium carbonate were added respectively, and 150 ml of toluene was added to dissolve it, and the reaction solution was heated to 80°C until it refluxed. The reaction was reacted for 12 hours. When the reaction was complete, water was added to quench the reaction. At the same time, the organic phase was extracted with dichloromethane for multiple times, and the organic phases washed multiple times were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated to dryness to obtain a crude product, which was purified by flash column chromatography to obtain intermediate 5-1 with a molar weight of 8.26 mmol and a yield of 82.6%. MS (ASAP) = 313.2.

[0181] Synthesis of intermediate 5-3:

[0182] Under nitrogen atmosphere, in a dry three-necked flask, 10 mmol of intermediate 5-1 and 10 mmol of compound 5-2, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine and 1.38 g of potassium carbonate were added, 150 ml of toluene was added to dissolve it, and the reaction solution was heated to 80°C to reflux. The reaction was allowed to proceed for 12 hours. When the reaction was complete, water was added to quench the reaction. At the same time, the organic phase was extracted with dichloromethane for multiple times. The organic phases washed multiple times were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated to dryness to obtain a crude product, which was purified by flash column chromatography to obtain intermediate 5-3 with a molar weight of 8.93 mmol and a yield of 89.3%. MS (ASAP) = 488.5.

[0183] Synthesis of intermediate 5-4:

[0184] Add 10mmol intermediate 5-3 and 100ml dry tert-butylbenzene to a 250ml three-necked flask, cool to -30°C in a N2 atmosphere, and add (30.6mmol) t-BuLi n-hexane solution dropwise. Raise the temperature to 60°C, react for 2 hours, and remove the n-hexane solvent under reduced pressure. Cool the reaction solution to -30°C again, add 10.5mmol boron tribromide solution, stir at room temperature for 0.5 hours, then cool the reaction solution to 0°C, add 21mmol N, N-diisopropylethylamine, wait for the addition to be completed, heat to room temperature and stir, then continue to heat to 120°C and stir for 3 hours, and cool the reaction solution to room temperature. Add sodium carbonate aqueous solution and ethyl acetate to quench the reaction. Extract the aqueous phase with ethyl acetate and combine the organic phases, evaporate the solvent, and obtain a crude product, which is purified by a rapid silica gel column to obtain a pure product. Recrystallization with toluene and ethyl acetate gave intermediate 5-4 with a molar weight of 4.97 mmol, a reaction yield of 49.7%, and MS (ASAP) = 462.5.

[0185] Synthesis of intermediate 5-5:

[0186] Under nitrogen atmosphere, in a dry three-necked flask, 10 mmol of intermediate 5-4 and 5 mmol of liquid bromine were added respectively, and 150 ml of concentrated sulfuric acid was added to dissolve them, and the mixture was heated to 80°C until the reaction solution refluxed. The reaction was allowed to proceed for 12 hours. When the reaction was complete, water was added to quench the reaction. At the same time, the organic phase was extracted with dichloromethane for multiple times, and the organic phases washed multiple times were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated to dryness to obtain a crude product, which was purified by flash column chromatography to obtain intermediate 5-5 with a molar weight of 8.87 mmol and a yield of 88.7%. MS (ASAP) = 540.3.

[0187] Synthesis of organic compound 5:

[0188] Prepare a dry 500mL three-necked flask, set up the reaction device, evacuate and pass nitrogen; keep nitrogen flowing in the reaction flask, weigh 20mmol of intermediate 5-5, add THF (250ml), evacuate and pass nitrogen for three cycles, and cool to -78°C; slowly drop 20mmol of n-butyl lithium solution into the reaction flask, react at -78°C for 30min, and quickly add 10mmol of compound 5-6. Let the reaction system slowly warm to room temperature and react for 12h. Add water, extract with DCM, spin dry the solvent, and use column chromatography (eluent is PE) to obtain a yellow-green solid, i.e., organic compound 5, with a yield of 38.7% and MS (ASAP) = 1132.7.

[0189] Example 6

[0190] The synthetic route of organic compound 6 in this example is as follows:

[0191]

[0192] Synthesis of intermediate 6-1:

[0193] Under nitrogen atmosphere, in a dry three-necked flask, 20 mmol of compound 5-2 and 10 mmol of compound 2-1, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine and 1.38 g of potassium carbonate were added, 150 ml of toluene was added to dissolve it, and the reaction solution was heated to 80°C to reflux. The reaction was allowed to proceed for 12 hours. When the reaction was complete, water was added to quench the reaction. At the same time, the organic phase was extracted with dichloromethane for multiple times. The organic phases washed multiple times were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated to dryness to obtain a crude product, which was purified by flash column chromatography to obtain intermediate 6-1 with a molar weight of 7.57 mmol and a yield of 75.7%. MS (ASAP) = 608.3.

[0194] Synthesis of intermediate 6-2:

[0195] Add 10mmol intermediate 6-1 and 100ml dry tert-butylbenzene to a 250ml three-necked flask, cool to -30℃ in N2 atmosphere, and add (10mmol) n-BuLi n-hexane solution dropwise. Raise the temperature to 60℃, react for 2 hours, and remove the n-hexane solvent under reduced pressure. Cool the reaction solution to -30℃ again, add 10.5mmol boron tribromide solution, stir at room temperature for 0.5 hours, then cool the reaction solution to 0℃, add 21mmol N,N-diisopropylethylamine, wait for the addition to be completed, heat to room temperature and stir, then continue to heat to 120℃ and stir for 3 hours, and cool the reaction solution to room temperature. Add sodium carbonate aqueous solution and ethyl acetate to quench the reaction. Extract the aqueous phase with ethyl acetate and combine the organic phases, evaporate the solvent to obtain a crude product, and purify with a rapid silica gel column to obtain a pure product. Recrystallization with toluene and ethyl acetate gave intermediate 6-2 with a molar weight of 7.22 mmol, a reaction yield of 72.2%, and MS (ASAP) = 538.4.

[0196] Synthesis of intermediate 6-3:

[0197] Under nitrogen atmosphere, in a dry three-necked flask, 10 mmol of intermediate 6-2 and 10 mmol of compound 2-4 were added to a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. Stir at 100°C for 6 h under nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the separated liquid was extracted and washed with water. The organic phase was collected, dried, concentrated under reduced pressure, column chromatographed and recrystallized to obtain intermediate 6-3, with a molar weight of 6.91 mmol, a yield of 69.1%, and MS (ASAP) = 614.4.

[0198] Synthesis of organic compound 6:

[0199] Prepare a dry 500mL three-necked flask, set up the reaction device, evacuate and pass nitrogen; keep nitrogen flowing in the reaction flask, weigh 20mmol of intermediate 6-3, add THF (250ml), evacuate and pass nitrogen for three cycles, and cool to -78°C; slowly drop 10mmol of n-butyl lithium solution into the reaction flask, react at -78°C for 30min, and quickly add 10mmol of intermediate 6-4. Let the reaction system slowly rise to room temperature and react for 12h. Add water, extract with DCM, spin dry the solvent, and use column chromatography (eluent is PE) to obtain a yellow-green solid, i.e., organic compound 6, with a yield of 30.8%, MS (ASAP) = 1452.3.

[0200] Example 7

[0201] The synthetic route of organic compound 7 in this example is as follows:

[0202]

[0203] Synthesis of intermediate 7-1:

[0204] Under nitrogen atmosphere, in a dry three-necked flask, 10 mmol of intermediate 6-2 and 10 mmol of compound 4-1 were added to a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. Stir at 100°C for 6 h under nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was collected, dried, concentrated under reduced pressure, column chromatographed and recrystallized to obtain intermediate 7-1, with a molar weight of 7.35 mmol, a yield of 73.5%, and MS (ASAP) = 614.5.

[0205] Synthesis of organic compound 7:

[0206] Prepare a dry 500mL three-necked flask, set up the reaction device, evacuate and pass nitrogen; keep nitrogen flowing in the reaction flask, weigh 20mmol of intermediate 7-1, add THF (250ml), evacuate and pass nitrogen for three cycles, and cool to -78°C; slowly drop 10mmol of tert-butyl lithium solution into the reaction flask, react at -78°C for 30min, and quickly add 10mmol of compound 5-6. Let the reaction system slowly warm to room temperature and react for 12h. Add water, extract with DCM, spin dry the solvent, and use column chromatography (eluent is PE) to obtain a yellow-green solid, that is, organic compound 7, with a yield of 29.6%, MS (ASAP) = 1368.8.

[0207] Example 8

[0208] The synthetic route of organic compound 8 in this example is as follows:

[0209]

[0210] Synthesis of intermediate 8-2:

[0211] Prepare a dry 500mL three-necked flask, set up the reaction device, evacuate and pass nitrogen; keep nitrogen flowing in the reaction flask, weigh 10mmol of intermediate 6-3, add THF (250ml), evacuate and pass nitrogen for three cycles, and cool to -78°C; slowly drop 10mmol of tert-butyl lithium solution into the reaction flask, react at -78°C for 30min, and quickly add 10mmol of compound 8-1. Let the reaction system slowly warm to room temperature and react for 12h. Add water, extract with DCM, spin dry the solvent, and purify by rapid column chromatography to obtain intermediate 8-2, with a molar weight of 7.11mmol, a yield of 71.1%, and MS (ASAP) = 820.5.

[0212] Synthesis of organic compound 8:

[0213] Prepare a dry 500mL three-necked flask, set up the reaction device, evacuate and pass nitrogen; keep nitrogen flowing in the reaction flask, weigh 10mmol of intermediate 5-5, add THF (250ml), evacuate and pass nitrogen for three cycles, and cool to -78°C; slowly drop 10mmol of n-butyl lithium solution into the reaction flask, react at -78°C for 30min, and quickly add 10mmol of intermediate 8-2. Let the reaction system slowly warm to room temperature and react for 12h. Add water, extract with DCM, spin dry the solvent, and use column chromatography (eluent is PE) to obtain a yellow-green solid, i.e., organic compound 8, with a yield of 25.7% and MS (ASAP) = 1250.8.

[0214] Example 9

[0215] The synthetic route of organic compound 9 in this example is as follows:

[0216]

[0217] Synthesis of intermediate 9-3:

[0218] Under nitrogen atmosphere, in a dry three-necked flask, 10 mmol of compound 9-1 and 10 mmol of compound 9-2, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine and 1.38 g of potassium carbonate were added respectively, and 150 ml of toluene was added to dissolve it, and the reaction solution was heated to 80°C until it refluxed. The reaction was allowed to react for 12 hours. When the reaction was complete, water was added to quench the reaction. At the same time, the organic phase was extracted with dichloromethane for multiple times, and the organic phases washed multiple times were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated to dryness to obtain a crude product, which was purified by flash column chromatography to obtain intermediate 9-3 with a molar weight of 8.98 mmol and a yield of 89.8%. MS (ASAP) = 239.4.

[0219] Synthesis of intermediate 9-4:

[0220] Under nitrogen atmosphere, in a dry three-necked flask, 20 mmol of intermediate 9-3 and 10 mmol of compound 1-2, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine and 1.38 g of potassium carbonate were added respectively, and 150 ml of toluene was added to dissolve it, and the reaction solution was heated to 80°C to reflux, and reacted for 12 hours. When the reaction was complete, water was added to quench the reaction, and the organic phase was extracted with dichloromethane for multiple times. The organic phases washed multiple times were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated to dryness to obtain a crude product, which was purified by flash column chromatography to obtain intermediate 9-4 with a molar weight of 8.17 mmol and a yield of 81.7%. MS (ASAP) = 586.3.

[0221] Synthesis of intermediate 9-5:

[0222] Add 10mmol intermediate 9-4 and 100ml dry tert-butylbenzene to a 250ml three-necked flask, cool to -30℃ in N2 atmosphere, and add (30.6mmol) t-BuLi n-hexane solution dropwise. Raise the temperature to 60℃, react for 2 hours, and remove the n-hexane solvent under reduced pressure. Cool the reaction solution to -30℃ again, add 10.5mmol boron tribromide solution, stir at room temperature for 0.5 hours, then cool the reaction solution to 0℃, add 21mmol N,N-diisopropylethylamine, wait for the addition to be completed, heat to room temperature and stir, then continue to heat to 120℃ and stir for 3 hours, and cool the reaction solution to room temperature. Add sodium carbonate aqueous solution and ethyl acetate to quench the reaction. Extract the aqueous phase with ethyl acetate and combine the organic phases, evaporate the solvent to obtain a crude product, and purify with a rapid silica gel column to obtain a pure product. Recrystallization with toluene and ethyl acetate gave intermediate 9-5 with a molar weight of 7.54 mmol, a reaction yield of 75.4%, and MS (ASAP) = 560.4.

[0223] Synthesis of intermediate 9-6:

[0224] Under nitrogen atmosphere, in a dry three-necked flask, 10 mmol of intermediate 9-5 and 5 mmol of liquid bromine were added respectively, and 150 ml of concentrated sulfuric acid was added to dissolve them, and the reaction solution was heated to 80°C until refluxed. The reaction was allowed to proceed for 12 hours. When the reaction was complete, water was added to quench the reaction. At the same time, the organic phase was extracted with dichloromethane for multiple times, and the organic phases washed multiple times were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated to dryness to obtain a crude product, which was purified by flash column chromatography to obtain intermediate 9-6 with a molar weight of 8.29 mmol and a yield of 82.9%. MS (ASAP) = 638.4.

[0225] Synthesis of intermediate 9-7:

[0226] Prepare a dry 500mL three-necked flask, set up the reaction device, evacuate and pass nitrogen; keep nitrogen flowing in the reaction flask, weigh 10mmol of intermediate 9-6, add THF (250ml), evacuate and pass nitrogen for three cycles, and cool to -78°C; slowly drop 10mmol of tert-butyl lithium solution into the reaction flask, react at -78°C for 30min, and quickly add 10mmol of compound 8-1. Let the reaction system slowly warm to room temperature and react for 12h. Add water, extract with DCM, spin dry the solvent, and purify by rapid column chromatography to obtain intermediate 9-7, with a molar weight of 7.84mmol, a yield of 78.4%, and MS (ASAP) = 800.4.

[0227] Synthesis of organic compound 9:

[0228] Prepare a dry 500mL three-necked flask, set up the reaction device, evacuate and pass nitrogen; keep nitrogen flowing in the reaction flask, weigh 10mmol of intermediate 1-5, add THF (250ml), evacuate and pass nitrogen for three cycles, and cool to -78°C; slowly drop 10mmol of n-butyl lithium solution into the reaction flask, react at -78°C for 30min, and quickly add 10mmol of intermediate 9-7. Let the reaction system slowly warm to room temperature and react for 12h. Add water, extract with DCM, spin dry the solvent, and use column chromatography (eluent is PE) to obtain a yellow-green solid, i.e., organic compound 9, with a yield of 33.9% and MS (ASAP) = 1188.6.

[0229] Example 10

[0230] The synthesis route of the organic compound 10 of this embodiment is as follows:

[0231]

[0232] Synthesis of intermediate 10-2:

[0233] Under nitrogen atmosphere, in a dry three-necked flask, 10 mmol of compound 9-1 and 10 mmol of compound 10-1, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine and 1.38 g of potassium carbonate were added respectively, and 150 ml of toluene was added to dissolve it, and the reaction solution was heated to 80°C until refluxed. The reaction was allowed to proceed for 12 hours. When the reaction was complete, water was added to quench the reaction. At the same time, the organic phase was extracted with dichloromethane for multiple times, the organic phases washed multiple times were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated to dryness to obtain a crude product, which was purified by flash column chromatography to obtain intermediate 10-2 with a molar weight of 8.33 mmol and a yield of 83.3%. MS (ASAP) = 239.2.

[0234] Synthesis of intermediate 10-3:

[0235] Under nitrogen atmosphere, in a dry three-necked flask, 20 mmol of intermediate 10-2 and 10 mmol of compound 2-1, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine and 1.38 g of potassium carbonate were added respectively, and 150 ml of toluene was added to dissolve it, and the reaction solution was heated to 80°C until refluxed. The reaction was reacted for 12 hours. When the reaction was complete, water was added to quench the reaction. At the same time, the organic phase was extracted with dichloromethane for multiple times, and the organic phases washed multiple times were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated to dryness to obtain a crude product, which was purified by flash column chromatography to obtain intermediate 10-3 with a molar weight of 7.86 mmol and a yield of 78.6%. MS (ASAP) = 664.5.

[0236] Synthesis of intermediate 10-4:

[0237] Add 10mmol intermediate 10-3 and 100ml dry tert-butylbenzene to a 250ml three-necked flask, cool to -30℃ in N2 atmosphere, and add (30.6mmol) n-BuLi n-hexane solution dropwise. Raise the temperature to 60℃, react for 2 hours, and remove the n-hexane solvent under reduced pressure. Cool the reaction solution to -30℃ again, add 10.5mmol boron tribromide solution, stir at room temperature for 0.5 hours, then cool the reaction solution to 0℃, add 21mmol N,N-diisopropylethylamine, wait for the addition to be completed, heat to room temperature and stir, then continue to heat to 120℃ and stir for 3 hours, and cool the reaction solution to room temperature. Add sodium carbonate aqueous solution and ethyl acetate to quench the reaction. Extract the aqueous phase with ethyl acetate and combine the organic phases, evaporate the solvent to obtain a crude product, and purify it with a rapid silica gel column to obtain a pure product. Recrystallization with toluene and ethyl acetate gave intermediate 10-4 with a molar weight of 5.69 mmol, a reaction yield of 56.9%, and MS (ASAP) = 594.3.

[0238] Synthesis of intermediate 10-5:

[0239] Under nitrogen atmosphere, in a dry three-necked flask, 10 mmol of intermediate 10-4 and 10 mmol of compound 2-4 were added to a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. Stir at 100°C for 6 h under nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was collected, dried, concentrated under reduced pressure, column chromatographed and recrystallized to obtain intermediate 10-5, with a molar weight of 8.46 mmol, a yield of 84.6%, and MS (ASAP) = 670.4.

[0240] Synthesis of intermediate 10-6:

[0241] Prepare a dry 500mL three-necked flask, set up the reaction device, evacuate and pass nitrogen; keep nitrogen flowing in the reaction flask, weigh 10mmol of intermediate 10-5, add THF (250ml), evacuate and pass nitrogen for three cycles, and cool to -78°C; slowly drop 10mmol of tert-butyl lithium solution into the reaction flask, react at -78°C for 30min, and quickly add 10mmol of compound 8-1. Let the reaction system slowly rise to room temperature and react for 12h. Add water, extract with DCM, spin dry the solvent, and purify by rapid column chromatography to obtain intermediate 10-6, with a molar weight of 6.84mmol, a yield of 68.4%, and MS (ASAP) = 876.5.

[0242] Synthesis of organic compound 10:

[0243] Prepare a dry 500mL three-necked flask, set up the reaction device, evacuate and pass nitrogen; keep nitrogen flowing in the reaction flask, weigh 10mmol of intermediate 1-5, add THF (250ml), evacuate and pass nitrogen for three cycles, and cool to -78°C; slowly drop 10mmol of n-butyl lithium solution into the reaction flask, react at -78°C for 30min, and quickly add 10mmol of intermediate 10-6. Let the reaction system slowly warm to room temperature and react for 12h. Add water, extract with DCM, spin dry the solvent, and use column chromatography (eluent is PE) to obtain a yellow-green solid, that is, organic compound 10, with a yield of 30.1%, MS (ASAP) = 1264.7.

[0244] Embodiment 11

[0245] The synthetic route of the organic compound 11 of this embodiment is as follows:

[0246]

[0247] Synthesis of organic compound 11:

[0248] Prepare a dry 500mL three-necked flask, set up the reaction device, evacuate and pass nitrogen; keep nitrogen flowing in the reaction flask, weigh 20mmol of intermediate 10-5, add THF (250ml), evacuate and pass nitrogen for three cycles, and cool to -78°C; slowly drop 10mmol of tert-butyl lithium solution into the reaction flask, react at -78°C for 30min, and quickly add 10mmol of compound 8-1. Let the reaction system slowly warm to room temperature and react for 12h. Add water, extract with DCM, spin dry the solvent, and use column chromatography (eluent is PE) to obtain a yellow-green solid, that is, organic compound 11, with a yield of 47.1%, MS (ASAP) = 1480.6.

[0249] Example 12

[0250] The synthetic route of the organic compound 12 of this embodiment is as follows:

[0251]

[0252] Synthesis of intermediate 12-1:

[0253] Under nitrogen atmosphere, in a dry three-necked flask, 10 mmol of intermediate 10-4 and 10 mmol of compound 4-1 were added to a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. Stir at 100°C for 6 h under nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was collected, dried, concentrated under reduced pressure, column chromatographed and recrystallized to obtain intermediate 12-1, with a molar weight of 7.66 mmol, a yield of 76.6%, and MS (ASAP) = 670.5.

[0254] Synthesis of organic compound 12:

[0255] Prepare a dry 500mL three-necked flask, set up the reaction device, evacuate and pass nitrogen; keep nitrogen flowing in the reaction flask, weigh 20mmol of intermediate 12-1, add THF (250ml), evacuate and pass nitrogen for three cycles, and cool to -78°C; slowly drop 10mmol of tert-butyl lithium solution into the reaction flask, react at -78°C for 30min, and quickly add 10mmol of compound 5-6. Let the reaction system slowly warm to room temperature and react for 12h. Add water, extract with DCM, spin dry the solvent, and use column chromatography (eluent is PE) to obtain a yellow-green solid, that is, organic compound 12, with a yield of 38.4%, MS (ASAP) = 1480.5.

[0256] Embodiment 13

[0257] The synthetic route of the organic compound 13 of this embodiment is as follows:

[0258]

[0259] Synthesis of intermediate 13-2:

[0260] Under nitrogen atmosphere, in a dry three-necked flask, 10 mmol of compound 9-1 and 10 mmol of compound 13-1, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine and 1.38 g of potassium carbonate were added respectively, and 150 ml of toluene was added to dissolve it, and the reaction solution was heated to 80°C until it refluxed. The reaction was allowed to react for 12 hours. When the reaction was complete, water was added to quench the reaction. At the same time, the organic phase was extracted with dichloromethane for multiple times, and the organic phases washed multiple times were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated to dryness to obtain a crude product, which was purified by flash column chromatography to obtain intermediate 13-2 with a molar weight of 8.35 mmol and a yield of 83.5%. MS (ASAP) = 315.5.

[0261] Synthesis of intermediate 13-3:

[0262] Under nitrogen atmosphere, in a dry three-necked flask, 20 mmol of intermediate 13-2 and 10 mmol of compound 2-1, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine and 1.38 g of potassium carbonate were added respectively, and 150 ml of toluene was added to dissolve it, and the reaction solution was heated to 80°C to reflux. The reaction was reacted for 12 hours. When the reaction was complete, water was added to quench the reaction. At the same time, the organic phase was extracted with dichloromethane for multiple times, and the organic phases washed multiple times were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated to dryness to obtain a crude product, which was purified by flash column chromatography to obtain intermediate 13-3 with a molar weight of 7.59 mmol and a yield of 75.9%. MS (ASAP) = 816.4.

[0263] Synthesis of intermediate 13-4:

[0264] Add 10mmol of intermediate 13-3 and 100ml of dried tert-butylbenzene to a 250ml three-necked flask, cool to -30°C in a N2 atmosphere, and add (30.6mmol) of n-BuLi n-hexane solution dropwise. Raise the temperature to 60°C, react for 2 hours, and remove the n-hexane solvent under reduced pressure. Cool the reaction solution to -30°C again, add 10.5mmol of boron tribromide solution, stir at room temperature for 0.5 hours, then cool the reaction solution to 0°C, add 21mmol of N,N-diisopropylethylamine, wait for the addition to be completed, heat to room temperature and stir, then continue to heat to 120°C and stir for 3 hours, and cool the reaction solution to room temperature. Add sodium carbonate aqueous solution and ethyl acetate to quench the reaction. Extract the aqueous phase with ethyl acetate and combine the organic phases, evaporate the solvent to obtain a crude product, and purify it with a rapid silica gel column to obtain a pure product. Recrystallization with toluene and ethyl acetate gave intermediate 13-4 with a molar weight of 7.27 mmol, a reaction yield of 72.7%, and MS (ASAP) = 746.5.

[0265] Synthesis of intermediate 13-5:

[0266] Under nitrogen atmosphere, in a dry three-necked flask, 10 mmol of intermediate 13-4 and 10 mmol of compound 2-4 were added to a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. Stir at 100°C for 6 h under nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was collected, dried, concentrated under reduced pressure, column chromatographed and recrystallized to obtain intermediate 13-5, with a molar weight of 8.39 mmol, a yield of 83.9%, and MS (ASAP) = 822.6.

[0267] Synthesis of organic compound 13:

[0268] Prepare a dry 500mL three-necked flask, set up the reaction device, evacuate and pass nitrogen; keep nitrogen flowing in the reaction flask, weigh 20mmol of intermediate 13-5, add THF (250ml), evacuate and pass nitrogen for three cycles, and cool to -78°C; slowly drop 10mmol of tert-butyl lithium solution into the reaction flask, react at -78°C for 30min, and quickly add compound 8-110mmol. Let the reaction system slowly warm to room temperature and react for 12h. Add water, extract with DCM, spin dry the solvent, and use column chromatography (eluent is PE) to obtain a yellow-green solid, that is, organic compound 13, with a yield of 42.7%, MS (ASAP) = 1784.3.

[0269] Embodiment 14

[0270] The synthetic route of the organic compound 14 of this embodiment is as follows:

[0271]

[0272] Synthesis of intermediate 14-2:

[0273] Under nitrogen atmosphere, in a dry three-necked flask, 20 mmol of compound 14-1 and 10 mmol of compound 2-1, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine and 1.38 g of potassium carbonate were added respectively, and 150 ml of toluene was added to dissolve it, and the reaction solution was heated to 80°C to reflux. The reaction was allowed to proceed for 12 hours. After the reaction was complete, water was added to quench the reaction. At the same time, the organic phase was extracted with dichloromethane for multiple times, the organic phases washed multiple times were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated to dryness to obtain a crude product, which was purified by flash column chromatography to obtain intermediate 14-2 with a molar weight of 7.33 mmol and a yield of 73.3%. MS (ASAP) = 624.3.

[0274] Synthesis of intermediate 14-3:

[0275] Add 10mmol of intermediate 14-2 and 100ml of dry tert-butylbenzene to a 250ml three-necked flask, cool to -30℃ in N2 atmosphere, and add (10mmol) n-BuLi n-hexane solution dropwise. Raise the temperature to 60℃, react for 2 hours, and remove the n-hexane solvent under reduced pressure. Cool the reaction solution to -30℃ again, add 10.5mmol of boron tribromide solution, stir at room temperature for 0.5 hours, then cool the reaction solution to 0℃, add 21mmol of N,N-diisopropylethylamine, wait for the addition to be completed, heat to room temperature and stir, then continue to heat to 120℃ and stir for 3 hours, and cool the reaction solution to room temperature. Add sodium carbonate aqueous solution and ethyl acetate to quench the reaction. Extract the aqueous phase with ethyl acetate and combine the organic phases, evaporate the solvent to obtain a crude product, and purify it with a rapid silica gel column to obtain a pure product. Recrystallization with toluene and ethyl acetate gave intermediate 14-3 with a molar weight of 7.51 mmol, a reaction yield of 75.1%, and MS (ASAP) = 554.8.

[0276] Synthesis of intermediate 14-4:

[0277] Under nitrogen atmosphere, in a dry three-necked flask, 10 mmol of intermediate 14-3 and 10 mmol of compound 2-4 were added to a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. Stir at 100°C for 6 h under nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was collected, dried, concentrated under reduced pressure, column chromatographed and recrystallized to obtain intermediate 14-4, with a molar weight of 6.32 mmol, a yield of 63.2%, and MS (ASAP) = 630.5.

[0278] Synthesis of organic compound 14:

[0279] Prepare a dry 500mL three-necked flask, set up the reaction device, evacuate and pass nitrogen; keep nitrogen flowing in the reaction flask, weigh 20mmol of intermediate 14-4, add THF (250ml), evacuate and pass nitrogen for three cycles, and cool to -78°C; slowly drop 10mmol of n-butyl lithium solution into the reaction flask, react at -78°C for 30min, and quickly add 10mmol of compound 6-4. Let the reaction system slowly warm to room temperature and react for 12h. Add water, extract with DCM, spin dry the solvent, and use column chromatography (eluent is PE) to obtain a yellow-green solid, that is, organic compound 14, with a yield of 35.9% and MS (ASAP) = 1484.8.

[0280] Embodiment 15

[0281] The synthetic route of the organic compound 15 of this embodiment is as follows:

[0282]

[0283] Synthesis of intermediate 15-2:

[0284] Under nitrogen atmosphere, in a dry three-necked flask, 10 mmol of compound 15-1 and 10 mmol of compound 9-1, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine and 1.38 g of potassium carbonate were added respectively, and 150 ml of toluene was added to dissolve it, and the reaction solution was heated to 80°C to reflux. The reaction was allowed to proceed for 12 hours. When the reaction was complete, water was added to quench the reaction. At the same time, the organic phase was extracted with dichloromethane for multiple times, the organic phases washed multiple times were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated to dryness to obtain a crude product, which was purified by flash column chromatography to obtain intermediate 15-2 with a molar weight of 8.11 mmol and a yield of 81.1%. MS (ASAP) = 225.3.

[0285] Synthesis of intermediate 15-3:

[0286] Under nitrogen atmosphere, in a dry three-necked flask, 10 mmol of intermediate 15-2 and 10 mmol of compound 1-2, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine and 1.38 g of potassium carbonate were added respectively, and 150 ml of toluene was added to dissolve it, and the reaction solution was heated to 80°C to reflux. The reaction was reacted for 12 hours. When the reaction was complete, water was added to quench the reaction. At the same time, the organic phase was extracted with dichloromethane for multiple times, and the organic phases washed multiple times were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated to dryness to obtain a crude product, which was purified by flash column chromatography to obtain intermediate 15-3 with a molar weight of 7.59 mmol and a yield of 75.9%. MS (ASAP) = 369.4.

[0287] Synthesis of intermediate 15-4:

[0288] Under nitrogen atmosphere, in a dry three-necked flask, 10 mmol of intermediate 15-3 and 10 mmol of compound 1-1, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine and 1.38 g of potassium carbonate were added respectively, and 150 ml of toluene was added to dissolve it, and the reaction solution was heated to 80°C to reflux. The reaction was reacted for 12 hours. When the reaction was complete, water was added to quench the reaction. At the same time, the organic phase was extracted with dichloromethane for multiple times, and the organic phases washed multiple times were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated to dryness to obtain a crude product, which was purified by flash column chromatography to obtain intermediate 15-4 with a molar weight of 8.35 mmol and a yield of 83.5%. MS (ASAP) = 502.5.

[0289] Synthesis of intermediate 15-5:

[0290] Add 10 mmol of intermediate 15-4 and 100 ml of dry tert-butylbenzene to a 250 ml three-necked flask, cool to -30 ° C in a N2 atmosphere, and add (30.6 mmol) of t-BuLi n-hexane solution dropwise. Raise the temperature to 60 ° C, react for 2 hours, and remove the n-hexane solvent under reduced pressure. Cool the reaction solution to -30 ° C again, add 10.5 mmol of boron tribromide solution, stir at room temperature for 0.5 hours, then cool the reaction solution to 0 ° C, add 21 mmol of N, N-diisopropylethylamine, wait for the addition to be completed, heat to room temperature and stir, then continue to heat to 120 ° C and stir for 3 hours, and cool the reaction solution to room temperature. Add sodium carbonate aqueous solution and ethyl acetate to quench the reaction. Extract the aqueous phase with ethyl acetate and combine the organic phases, evaporate the solvent, and obtain a crude product, which is purified by a rapid silica gel column to obtain a pure product. Recrystallization with toluene and ethyl acetate gave intermediate 15-5 with a molar weight of 4.33 mmol, a reaction yield of 43.3%, and MS (ASAP) = 476.5.

[0291] Synthesis of intermediate 15-6:

[0292] Under nitrogen atmosphere, in a dry three-necked flask, 10 mmol of intermediate 15-5 and 5 mmol of liquid bromine were added respectively, and 150 ml of concentrated sulfuric acid was added to dissolve them. The mixture was heated to 80°C until the reaction solution refluxed and reacted for 12 hours. When the reaction was complete, water was added to quench the reaction. At the same time, the organic phase was extracted with dichloromethane for multiple times, the organic phases washed multiple times were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated to dryness to obtain a crude product, which was purified by flash column chromatography to obtain intermediate 15-6 with a molar weight of 8.55 mmol and a yield of 85.5%. MS (ASAP) = 554.2.

[0293] Synthesis of intermediate 15-7:

[0294] Prepare a dry 500mL three-necked flask, set up the reaction device, evacuate and pass nitrogen; keep nitrogen flowing in the reaction flask, weigh 10mmol of intermediate 15-6, add THF (250ml), evacuate and pass nitrogen for three cycles, and cool to -78°C; slowly drop 20mmol of n-butyl lithium solution into the reaction flask, react at -78°C for 30min, and quickly add 10mmol of compound 8-1. Let the reaction system slowly warm to room temperature and react for 12h. Add water, extract with DCM, spin dry the solvent, and use column chromatography (eluent is PE) to obtain intermediate 15-7, with a molar weight of 4.89mmol, a reaction yield of 48.9%, and MS (ASAP) = 716.4.

[0295] Synthesis of organic compound 15:

[0296] Prepare a dry 500mL three-necked flask, set up the reaction device, evacuate and pass nitrogen; keep nitrogen flowing in the reaction flask, weigh 20mmol of intermediate 1-5, add THF (250ml), evacuate and pass nitrogen for three cycles, and cool to -78°C; slowly drop 20mmol of n-butyl lithium solution into the reaction flask, react at -78°C for 30min, and quickly add 10mmol of intermediate 15-7. Let the reaction system slowly warm to room temperature and react for 12h. Add water, extract with DCM, spin dry the solvent, and use column chromatography (eluent is PE) to obtain a yellow-green solid, i.e., organic compound 15, with a yield of 32.5%, MS (ASAP) = 1104.6.

[0297] Example 16

[0298] The synthetic route of organic compound 16 in this example is as follows:

[0299]

[0300] Synthesis of intermediate 16-2:

[0301] Under nitrogen atmosphere, in a dry three-necked flask, 10 mmol of compound 16-1 and 10 mmol of compound 9-1, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine and 1.38 g of potassium carbonate were added respectively, and 150 ml of toluene was added to dissolve it, and the reaction solution was heated to 80°C until it refluxed. The reaction was reacted for 12 hours. When the reaction was complete, water was added to quench the reaction. At the same time, the organic phase was extracted with dichloromethane for multiple times, and the organic phases washed multiple times were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated to dryness to obtain a crude product, which was purified by flash column chromatography to obtain intermediate 16-2 with a molar weight of 8.34 mmol and a yield of 83.4%. MS (ASAP) = 225.5.

[0302] Synthesis of intermediate 16-3:

[0303] Under nitrogen atmosphere, in a dry three-necked flask, 10 mmol of intermediate 16-2 and 10 mmol of compound 1-2, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine and 1.38 g of potassium carbonate were added respectively, and 150 ml of toluene was added to dissolve it, and the reaction solution was heated to 80°C to reflux. The reaction was reacted for 12 hours. When the reaction was complete, water was added to quench the reaction. At the same time, the organic phase was extracted with dichloromethane for multiple times, and the organic phases washed multiple times were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated to dryness to obtain a crude product, which was purified by flash column chromatography to obtain intermediate 16-3 with a molar weight of 7.17 mmol and a yield of 71.7%. MS (ASAP) = 369.1.

[0304] Synthesis of intermediate 16-4:

[0305] Under nitrogen atmosphere, in a dry three-necked flask, 10 mmol of intermediate 16-3 and 10 mmol of compound 1-1, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine and 1.38 g of potassium carbonate were added respectively, and 150 ml of toluene was added to dissolve it, and the reaction solution was heated to 80°C to reflux. The reaction was reacted for 12 hours. When the reaction was complete, water was added to quench the reaction. At the same time, the organic phase was extracted with dichloromethane for multiple times, and the organic phases washed multiple times were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated to dryness to obtain a crude product, which was purified by flash column chromatography to obtain intermediate 16-4 with a molar weight of 7.29 mmol and a yield of 72.9%. MS (ASAP) = 502.7.

[0306] Synthesis of intermediate 16-5:

[0307] Add 10 mmol of intermediate 16-4 and 100 ml of dry tert-butylbenzene to a 250 ml three-necked flask, cool to -30 ° C in a N2 atmosphere, and add (30.6 mmol) of t-BuLi n-hexane solution dropwise. Raise the temperature to 60 ° C, react for 2 hours, and remove the n-hexane solvent under reduced pressure. Cool the reaction solution to -30 ° C again, add 10.5 mmol of boron tribromide solution, stir at room temperature for 0.5 hours, then cool the reaction solution to 0 ° C, add 21 mmol of N, N-diisopropylethylamine, and after the addition is complete, heat to room temperature and stir, then continue to heat to 120 ° C and stir for 3 hours, and cool the reaction solution to room temperature. Add sodium carbonate aqueous solution and ethyl acetate to quench the reaction. Extract the aqueous phase with ethyl acetate and combine the organic phases, evaporate the solvent, and obtain a crude product, which is purified by a rapid silica gel column to obtain a pure product. Recrystallization with toluene and ethyl acetate gave intermediate 16-5 with a molar weight of 4.26 mmol, a reaction yield of 42.6%, and MS (ASAP) = 476.1.

[0308] Synthesis of intermediate 16-6:

[0309] Under nitrogen atmosphere, in a dry three-necked flask, 10 mmol of intermediate 16-5 and 5 mmol of liquid bromine were added respectively, and 150 ml of concentrated sulfuric acid was added to dissolve them. The mixture was heated to 80°C until the reaction solution refluxed and reacted for 12 hours. When the reaction was complete, water was added to quench the reaction. At the same time, the organic phase was extracted with dichloromethane for multiple times, the organic phases washed multiple times were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated to dryness to obtain a crude product, which was purified by flash column chromatography to obtain intermediate 16-6 with a molar weight of 8.07 mmol and a yield of 80.7%. MS (ASAP) = 554.6.

[0310] Synthesis of intermediate 16-7:

[0311] Prepare a dry 500mL three-necked flask, set up the reaction device, evacuate and pass nitrogen; keep nitrogen flowing in the reaction flask, weigh 10mmol of intermediate 16-6, add THF (250ml), evacuate and pass nitrogen for three cycles, and cool to -78°C; slowly drop 20mmol of n-butyl lithium solution into the reaction flask, react at -78°C for 30min, and quickly add 10mmol of compound 8-1. Let the reaction system slowly warm to room temperature and react for 12h. Add water, extract with DCM, spin dry the solvent, and use column chromatography (eluent is PE) to obtain intermediate 16-7, with a molar weight of 3.84mmol, a reaction yield of 38.4%, and MS (ASAP) = 716.5.

[0312] Synthesis of organic compound 16:

[0313] Prepare a dry 500mL three-necked flask, set up the reaction device, evacuate and pass nitrogen; keep nitrogen flowing in the reaction flask, weigh 20mmol of intermediate 1-5, add THF (250ml), evacuate and pass nitrogen for three cycles, and cool to -78°C; slowly drop 20mmol of n-butyl lithium solution into the reaction flask, react at -78°C for 30min, and quickly add 10mmol of intermediate 16-7. Let the reaction system slowly warm to room temperature and react for 12h. Add water, extract with DCM, spin dry the solvent, and use column chromatography (eluent is PE) to obtain a yellow-green solid, i.e., organic compound 16, with a yield of 29.5%, MS (ASAP) = 1104.8.

[0314] Embodiment 17

[0315] The synthetic route of organic compound 17 in this example is as follows:

[0316]

[0317] Synthesis of intermediate 17-2:

[0318] Under nitrogen atmosphere, in a dry three-necked flask, 10 mmol of compound 17-1 and 10 mmol of compound 9-1, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine and 1.38 g of potassium carbonate were added respectively, and 150 ml of toluene was added to dissolve it, and the reaction solution was heated to 80°C to reflux. The reaction was allowed to proceed for 12 hours. When the reaction was complete, water was added to quench the reaction. At the same time, the organic phase was extracted with dichloromethane for multiple times, the organic phases washed multiple times were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated to dryness to obtain a crude product, which was purified by flash column chromatography to obtain intermediate 17-2 with a molar weight of 8.16 mmol and a yield of 81.6%. MS (ASAP) = 259.4.

[0319] Synthesis of intermediate 17-3:

[0320] Under nitrogen atmosphere, in a dry three-necked flask, 10 mmol of intermediate 17-2 and 10 mmol of compound 1-2, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine and 1.38 g of potassium carbonate were added respectively, and 150 ml of toluene was added to dissolve it, and the reaction solution was heated to 80°C to reflux. The reaction was reacted for 12 hours. When the reaction was complete, water was added to quench the reaction. At the same time, the organic phase was extracted with dichloromethane for multiple times, and the organic phases washed for multiple times were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated to dryness to obtain a crude product, which was purified by flash column chromatography to obtain intermediate 17-3 with a molar weight of 7.53 mmol and a yield of 75.3%. MS (ASAP) = 403.4.

[0321] Synthesis of intermediate 17-4:

[0322] Under nitrogen atmosphere, in a dry three-necked flask, 10 mmol of intermediate 17-3 and 10 mmol of compound 1-1, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine and 1.38 g of potassium carbonate were added respectively, and 150 ml of toluene was added to dissolve it, and the reaction solution was heated to 80°C to reflux. The reaction was reacted for 12 hours. When the reaction was complete, water was added to quench the reaction. At the same time, the organic phase was extracted with dichloromethane for multiple times, and the organic phases washed multiple times were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated to dryness to obtain a crude product, which was purified by flash column chromatography to obtain intermediate 17-4 with a molar weight of 6.42 mmol and a yield of 64.2%. MS (ASAP) = 536.5.

[0323] Synthesis of intermediate 17-5:

[0324] Add 10 mmol of intermediate 17-4 and 100 ml of dry tert-butylbenzene to a 250 ml three-necked flask, cool to -30 ° C in a N2 atmosphere, and add (30.6 mmol) of t-BuLi n-hexane solution dropwise. Raise the temperature to 60 ° C, react for 2 hours, and remove the n-hexane solvent under reduced pressure. Cool the reaction solution to -30 ° C again, add 10.5 mmol of boron tribromide solution, stir at room temperature for 0.5 hours, then cool the reaction solution to 0 ° C, add 21 mmol of N, N-diisopropylethylamine, wait for the addition to be completed, heat to room temperature and stir, then continue to heat to 120 ° C and stir for 3 hours, and cool the reaction solution to room temperature. Add sodium carbonate aqueous solution and ethyl acetate to quench the reaction. Extract the aqueous phase with ethyl acetate and combine the organic phases, evaporate the solvent, and obtain a crude product, which is purified by a rapid silica gel column to obtain a pure product. Recrystallization with toluene and ethyl acetate gave intermediate 17-5 with a molar weight of 4.28 mmol, a reaction yield of 42.8%, and MS (ASAP) = 510.5.

[0325] Synthesis of intermediate 17-6:

[0326] Under nitrogen atmosphere, in a dry three-necked flask, 10 mmol of intermediate 17-5 and 5 mmol of liquid bromine were added respectively, and 150 ml of concentrated sulfuric acid was added to dissolve it, and the reaction solution was heated to 80°C until refluxed. The reaction was reacted for 12 hours. When the reaction was complete, water was added to quench the reaction. At the same time, the organic phase was extracted with dichloromethane for multiple times, and the organic phases washed multiple times were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated to dryness to obtain a crude product, which was purified by flash column chromatography to obtain intermediate 17-6 with a molar weight of 8.59 mmol and a yield of 85.9%. MS (ASAP) = 588.2.

[0327] Synthesis of intermediate 17-7:

[0328] Prepare a dry 500mL three-necked flask, set up the reaction device, evacuate and pass nitrogen; keep nitrogen flowing in the reaction flask, weigh 10mmol of intermediate 17-6, add THF (250ml), evacuate and pass nitrogen for three cycles, and cool to -78°C; slowly drop 20mmol of n-butyl lithium solution into the reaction flask, react at -78°C for 30min, and quickly add 10mmol of compound 8-1. Let the reaction system slowly warm to room temperature and react for 12h. Add water, extract with DCM, spin dry the solvent, and use column chromatography (eluent is PE) to obtain intermediate 17-7, with a molar weight of 4.37mmol, a reaction yield of 43.7%, and MS (ASAP) = 750.4.

[0329] Synthesis of organic compound 17:

[0330] Prepare a dry 500mL three-necked flask, set up the reaction device, evacuate and pass nitrogen; keep nitrogen flowing in the reaction flask, weigh 20mmol of intermediate 1-5, add THF (250ml), evacuate and pass nitrogen for three cycles, and cool to -78°C; slowly drop 20mmol of n-butyl lithium solution into the reaction flask, react at -78°C for 30min, and quickly add 10mmol of intermediate 17-7. Let the reaction system slowly warm to room temperature and react for 12h. Add water, extract with DCM, spin dry the solvent, and use column chromatography (eluent is PE) to obtain a yellow-green solid, i.e., organic compound 17, with a yield of 33.6% and MS (ASAP) = 1138.4.

[0331] Comparative Example

[0332] The organic compound of this comparative example is BD-Ref1, and its chemical structure is as follows:

[0333]

[0334] Preparation of OLED devices

[0335] In the blue OLED device of this embodiment, ITO is used as the anode, PEDOT (polyethylene dioxythiophene, Clevios TM AI4083) is used as a hole injection layer material, PVK (Sigma Aldrich, average Mn 25,000-50,000) is used as a hole transport material, BH is used as a host material of the light-emitting material, the organic compounds of Examples 1-17 and BD-Ref1 in the comparative example are used as guest materials of the light-emitting material, ET and Liq (8-hydroxyquinoline lithium) are used as electron transport materials, Al is used as a cathode, and the device structure is ITO / PEDOT / PVK / BH: organic compound / ET:Liq / Al.

[0336] The schematic diagram of OLED device is shown in Figure 1 As shown, 10 is a substrate, 20 is an anode, 30 is a hole injection layer, 40 is a hole transport layer, 50 is a light emitting layer, 60 is an electron transport layer, and 70 is a cathode.

[0337] The chemical structural formulas of BH, ET and Liq are as follows:

[0338]

[0339] The above-mentioned BH, ET, Liq, and BD-Ref1 are all commercially available, or their synthesis methods are all prior art.

[0340] The preparation process of an OLED device using the above materials is described in detail below through specific examples.

[0341] Device Example 1

[0342] The method for preparing an OLED device in this embodiment comprises the following steps:

[0343] a. Cleaning of ITO (indium tin oxide) anode layer: Use chloroform, acetone and / or isopropyl alcohol to clean the ITO conductive glass, and then perform UV ozone treatment;

[0344] b. Forming a hole injection layer: Spin-coat the hole injection layer material PEDOT (polyethylene dioxythiophene, Clevios TM AI4083), and treated on a hot plate at 180°C for 10 minutes, the thickness of the hole injection layer was 40 nm;

[0345] c. Forming a hole transport layer: Spin-coat a toluene solution of PVK (Sigma Aldrich, average Mn 25,000-50,000) with a concentration of 5 mg / ml on the hole injection layer, and then treat on a hot plate at 180° C. for 60 minutes. The thickness of the hole transport layer is 20 nm.

[0346] d. Forming a light-emitting layer: In a nitrogen glove box, spin-coat the light-emitting layer material on the hole transport layer, and then treat it on a hot plate at 140° C. for 10 minutes. The main material of the light-emitting layer material is BH, the guest material is the organic compound 1 of Example 1 of the present application, the solvent is methyl benzoate solution, the mass ratio of the main material to the guest material is 95:5, the concentration of the light-emitting layer material is 15 mg / ml, and the thickness of the light-emitting layer is 40 nm.

[0347] e. Forming the electron transport layer: In a vacuum chamber, above the light-emitting layer, ET and Liq are placed in different evaporation units and heated in a high vacuum (1×10 -6 mbar) to co-deposit ET and Liq at a weight ratio of 50:50 to form an electron transport layer with a thickness of 20 nm;

[0348] f. Forming a cathode layer: depositing Al on the electron transport layer to obtain an Al cathode with a thickness of 100 nm;

[0349] g. Packaging: The device was packaged with ultraviolet curing resin in a nitrogen glove box to obtain the device OLED-1.

[0350] Device Examples 2-17

[0351] It is basically the same as the device example 1, except that the guest materials of the light-emitting layers of OLED-1 to OLED-17 of the device examples 2-17 are respectively selected from the organic compounds of examples 2-17.

[0352] Device Comparison

[0353] It is basically the same as the device example 1, except that the guest material of the light-emitting layer of the device comparative example OLED-BD-Ref1 is the organic compound BD-Ref1.

[0354] Performance testing and results

[0355] The current-voltage (JV) characteristics of devices OLED-1 to OLED-17 and OLED-BD-Ref1 were tested using characterization equipment, and important parameters such as CIE color coordinates (x, y), voltage @ 1 knits [V], luminous efficiency and life LT95 @ 1000 nits were recorded. Among them, the luminous efficiency is the current density of 10mA / cm 2The relative value obtained when the device is powered on; the lifespan LT95@1000nits refers to the time it takes for the device's brightness to drop from an initial brightness of 1000nits to 95% of the initial brightness under a constant current. The test results are shown in Table 1 below.

[0356] Table 1:

[0357]

[0358] From Table 1 we can see that:

[0359] The blue light devices OLED-1 to OLED-17 prepared by the organic compounds of Examples 1-17 of the present application have better luminous efficiency and lifespan than the device OLED-Ref1 prepared by the compounds of the comparative example. Among them, compared with the blue light device prepared by using the organic compound BD-Ref1 of the comparative example as the guest material in the light-emitting layer, the lifespan of the blue light device prepared by using the organic compounds 1 to 17 of Examples 1-17 as the guest material in the light-emitting layer is generally increased by 50-77%.

[0360] The double borosilicate system introduced into the organic compound of the present application increases the Td temperature (decomposition temperature) of the organic compound, making it easier to sublimate, and can effectively improve the purity of the organic compound, thereby improving and extending the luminous efficiency and service life of the device. In addition, the introduced double borosilicate system can significantly increase the molecular weight of the organic compound relative to the comparative organic compound BD-Ref1.

[0361] The organic compound of the present application is connected to silicon via two boron nitrogen compounds, so that the overall molecular structure has better conjugation and planarity, thereby improving the rigidity and stability of the organic compound molecules, thereby achieving the purpose of extending the luminous efficiency and service life of the device.

[0362] The organic compounds, mixtures, compositions and organic electronic devices provided in the embodiments of the present application are introduced in detail above. Specific examples are used herein to illustrate the principles and implementation methods of the present application. The description of the above embodiments is only used to help understand the method of the present application and its core idea. At the same time, for technicians in this field, according to the ideas of the present application, there will be changes in the specific implementation methods and application scopes. In summary, the content of this specification should not be understood as limiting the present application.

Claims

1. An organic compound, characterized in that It has a structure as shown in the general formula (1): in: Each occurrence of R1 and R2 is independently selected from: -H, tert-butyl; M1 and M2 are independently selected from the structure represented by formula (A-1) or (A-2): Ar1 and Ar4 are independently selected from the group Ar2 and Ar3 are each independently selected from any one of the following groups: X is selected from CR3; Y is selected from S or O; Each occurrence of R3 is independently selected from: -H, methyl, tert-butyl or isopropyl; * indicates the attachment site; The structure of the organic compound is selected from any one of the structures shown in general formulae (2-1) to (2-4):

2. The organic compound according to claim 1, characterized in that The structure represented by formula (A-1) is selected from any one of the structures represented by formula (C-1), (C-5), (C-6), (C-9) and (C-16): and / or The structure represented by formula (A-2) is selected from any one of the structures represented by formula (D-1), (D-2), (D-12) and (D-16):

3. The organic compound according to claim 1, characterized in that The structure of the organic compound is selected from any one of the structures shown in general formulae (3-1) to (3-5), general formula (3-7), and general formulae (3-10) to (3-13):

4. The organic compound according to claim 1, characterized in that The organic compound is selected from the following structures:

5. A mixture, characterized in that: The mixture comprises the organic compound according to any one of claims 1 to 4 and at least one organic functional material, wherein the organic functional material is selected from hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, luminescent guest materials, luminescent host materials or organic dyes.

6. A composition, characterized in that: The composition comprises the organic compound according to any one of claims 1 to 4 or the mixture according to claim 5, and at least one organic solvent.

7. An organic electronic device comprising at least one organic functional layer, characterized in that: The organic functional layer comprises the organic compound according to any one of claims 1 to 4, or the mixture according to claim 5, or the organic functional layer is prepared from the composition according to claim 6.

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