Organic compounds and mixtures, compositions, and organic electronic devices comprising the same

Abstract

The present invention discloses an organic compound with the following structure: The organic compound of the present invention is linked to dimethyl acridine through a silicon-containing group, making the molecular structure of the overall compound have better conjugation and planarity, improving the rigidity and stability of the material molecule. The introduction of diphenylsilicon further improves the solubility of the molecule, making the compound easier to purify, so that a compound with higher purity can be obtained. When used as a blue light emitting material in organic electronic devices, it can achieve the purpose of extending the luminous efficiency and service life of the device. In addition, the organic compound of the present invention can be used as a blue light guest material, and by cooperating with a suitable host material, it can improve the luminous efficiency and life of the electroluminescent device. Further, the present invention also discloses a mixture, a composition and an organic electronic device.

Description

Technical Field

[0001] The present invention relates to the technical field of organic 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] In flat panel display and lighting applications, organic light emitting diodes (OLEDs) have the advantages of low cost, light weight, low operating voltage, high brightness, color tunability, wide viewing angle, easy assembly and low energy consumption, making them the most promising display technology.

[0003] The principle of light emission of organic electronic devices is organic electroluminescence, which refers to the phenomenon of converting electrical energy into light energy using organic substances. Organic electroluminescent devices using organic electroluminescence usually have a positive electrode and a negative electrode and a functional layer containing organic matter between them. In order to improve the efficiency and life of organic electroluminescent elements, the functional layer has a multilayer structure, and each functional layer contains different organic substances. Specifically, it includes a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer or an electron injection layer. In an organic electroluminescent device, when a voltage is applied between the two electrodes, holes are injected into the organic layer from the positive electrode, and electrons are injected into the organic layer from the negative electrode. When the injected holes meet the electrons, excitons are formed, and light is emitted when the excitons transition back to the ground state. This organic electroluminescent element has the characteristics of self-luminescence, high brightness, high efficiency, low driving voltage, wide viewing angle, high contrast, and high responsiveness.

[0004] 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 is 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 have a major difficulty: the 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.

[0005] So far, the phosphorescent materials with practical use value are iridium and platinum complexes. Such raw materials are rare and expensive, and the synthesis of the complexes is complicated, so the cost is also quite high. In order to overcome the above problems, Adachi proposed the concept of reverse internal conversion, which can use organic compounds, that is, not use metal complexes, and achieve high efficiency comparable to phosphorescent OLEDs. This concept has been realized through various material combinations, such as: 1) using composite excited states; 2) using thermally excited delayed fluorescence (TADF) materials.

[0006] Traditional blue TADF materials have achieved good results in various performance aspects. However, compared with phosphorescent materials, there is still a certain gap in performance, whether in terms of efficiency or lifespan. Summary of the Invention

[0007] In view of this, the present invention provides an organic compound, aiming to provide new organic functional materials to improve the performance and lifespan of devices.

[0008] The present invention is achieved through the following technical solutions:

[0009] An organic compound having a structure represented by the general formula (1):

[0010]

[0011] Wherein:

[0012] X1, X2, and X3 are each independently selected from CR6 or N, and at least one of X1, X2, and X3 is selected from N;

[0013] Ar1, Ar2, and Ar3 are each independently selected from a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, or an alkyl group having 3 to 30 carbon atoms;

[0014] Each occurrence of R1, R2, R3, R4, R5, and R6 is independently selected from: -H, -D, a straight-chain alkyl group having 1 to 20 C atoms, a straight-chain alkoxy group having 1 to 20 C atoms, a straight-chain thioalkoxy group having 1 to 20 C atoms, a branched-chain alkyl group having 3 to 20 C atoms, a cyclic alkyl group having 3 to 20 C atoms, a branched-chain alkoxy group having 3 to 20 C atoms, a cyclic alkoxy group having 3 to 20 C atoms, a branched-chain thioalkoxy group having 3 to 20 C atoms, a cyclic thioalkoxy group having 3 to 20 C atoms, a silyl group, a ketone group having 1 to 20 C atoms, an alkoxycarbonyl group having 2 to 20 C atoms, an aryloxycarbonyl group having 7 to 20 C atoms, an alkenyl group having 1 to 20 C atoms, a carbamoyl group, a halocarbonyl group, a formyl group, a cyano group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, -CF3, -Cl, -Br, -F, a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaryloxy group having 5 to 30 ring atoms, or a combination of these groups;

[0015] m is selected from 1, 2, 3, or 4.

[0016] Correspondingly, the present invention further provides a mixture, comprising the above-mentioned organic compound and at least one organic functional material, and the organic functional material is selected from a hole injection material, a hole transport material, an electron transport material, an electron injection material, an electron blocking material, a hole blocking material, a light-emitting guest material, a light-emitting host material or an organic dye.

[0017] Correspondingly, the present invention further provides a composition, comprising the above-mentioned organic compound or the above-mentioned mixture, and at least one organic solvent.

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

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

[0020] The organic compound of the present invention has a D-A system, and a silicon-containing group is linked to dimethylacridine, so that the molecular structure of the whole compound has better conjugation and planarity, improving the rigidity and stability of the material molecule. The introduction of diarylsilicon (solubilizing group) further improves the solubility of the molecule and is more conducive to recrystallization, so that the compound is easier to purify, and thus a compound with higher purity can be obtained. When used as a blue light-emitting material in an organic electronic device, the compound with higher purity can improve the light-emitting efficiency and service life of the device. In addition, the organic compound of the present invention can be used as a blue light guest material, and by cooperating with a suitable host material, the light-emitting efficiency and service life of the electroluminescent device can be improved. BRIEF DESCRIPTION OF THE DRAWINGS

[0021] In order to more clearly illustrate the technical solutions in the embodiments of the present invention, the following will briefly introduce the drawings required for the description of the embodiments. Obviously, the following drawings are only some embodiments of the present invention, and those skilled in the art can also obtain other drawings without creative efforts based on these drawings.

[0022] Figure 1 It is a schematic diagram of the OLED device shown in Embodiment 1 of the device of the present invention;

[0023] Wherein 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. DETAILED DESCRIPTION OF THE EMBODIMENTS

[0024] The following will clearly and completely describe the technical solutions in the embodiments of the present invention in conjunction with the accompanying drawings in the embodiments of the present invention. Obviously, the described embodiments are only a part of the embodiments of the present invention, rather than all the embodiments. All other embodiments obtained by those skilled in the art based on the embodiments of the present invention without creative efforts belong to the scope of protection of the present invention. In addition, it should be understood that the specific implementation manners described herein are only used to illustrate and explain the present invention, and are not used to limit the present invention.

[0025] In the description of the present invention, the term "comprising" means "including but not limited to", and the term "a plurality of" means "two or more than two". The various embodiments of the present invention 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 brevity, and should not be construed as a rigid limitation on the scope of the present invention; therefore, it should be considered that the described range description has specifically disclosed all possible sub-ranges and single values within that range. For example, it should be considered that the range description from 1 to 6 has 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., and single numbers within the range, such as 1, 2, 3, 4, 5, and 6, regardless of the range. In addition, whenever a numerical range is indicated herein, it means including any cited number (fraction or integer) within the indicated range.

[0026] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by those of ordinary skill in the technical field to which the present invention belongs. The terms used in the description of the present invention in this specification are only for the purpose of describing specific embodiments, and are not intended to limit the present invention.

[0027] The terms "and / or", "or / and", and "and / or" used in the present invention include any one of two or more related listed items, and also include any and all combinations of the related listed items. The said any and all combinations include combinations of any two related listed items, any more related listed items, or all related listed items. It should be noted that when at least three items are connected by at least two conjunctions selected from "and / or", "or / and", and "and / or", it should be understood that in the present invention, this technical solution undoubtedly includes the technical solution connected by "logical AND", and also undoubtedly includes the technical solution connected by "logical OR". For example, "A and / or B" includes three parallel solutions: A, B, and A + B. Another example, the technical solution of "A, and / or, B, and / or, C, and / or, D" includes any one of A, B, C, and D (that is, the technical solution connected by "logical OR"), and also includes any and all combinations of A, B, C, and D, that is, it includes combinations of any two or any three of A, B, C, and D, and also includes the four-item combination of A, B, C, and D (that is, the technical solution connected by "logical AND").

[0028] In the present application, the composition and the printing ink, or the ink have the same meaning and can be interchanged.

[0029] In the present application, the aromatic group, the aromatic, and the aromatic ring system have the same meaning and can be interchanged.

[0030] In the present application, the heteroaromatic group, the heteroaromatic, and the heteroaromatic ring system have the same meaning and can be interchanged.

[0031] In the present application, "substituted" means that the hydrogen atom in the substituent is replaced by the substituent.

[0032] In the present invention, when the same substituent appears multiple times, it can be independently selected from different groups. For example, if the general formula contains multiple Rs, then the Rs can be independently selected from different groups.

[0033] In the present invention, "substituted or unsubstituted" means that the defined group may be substituted or may not be substituted. When the defined group is substituted, it should be understood that the defined group may be substituted by one or more substituents R, and the R is selected from, but not limited to: deuterium atom, cyano group, isocyano group, nitro group or halogen, alkyl group 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”, silyl group, carbonyl group, alkoxycarbonyl group, aryloxycarbonyl group, carbamoyl group, halocarbonyl group, formyl group, isocyanate group, thiocyanate group, isothiocyanate group, hydroxyl group, trifluoromethyl group, and the above groups may also be further substituted by substituents acceptable in the art; it is understandable that in -NR’R”, R’ and R” are each independently selected from, but not limited to: H, 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. 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 3-10 ring atoms, aromatic group containing 6-20 ring atoms, heteroaromatic group containing 5-20 ring atoms, silyl group, carbonyl group, alkoxycarbonyl group, aryloxycarbonyl group, carbamoyl group, halocarbonyl group, formyl group, isocyanate group, thiocyanate group, isothiocyanate group, hydroxyl group, trifluoromethyl group, and the above groups may also be further substituted by substituents acceptable in the art.

[0034] In the present invention, "number of ring atoms" means the number of atoms among the atoms constituting the ring itself of a structural compound obtained by bonding atoms into a ring (for example, monocyclic compound, fused ring compound, crosslinked compound, carbocyclic compound, heterocyclic compound). When the ring is substituted by a substituent, the atoms contained in the substituent are not included in the ring-forming atoms. The same applies to the "number of ring atoms" described below without special explanation. 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.

[0035] "Aryl or aromatic group" refers to an aromatic hydrocarbon group derived by removing one hydrogen atom from an aromatic ring compound, which can be a monocyclic aryl group, a fused-ring aryl group, or a polycyclic aryl group. For polycyclic ring systems, at least one is an aromatic ring system. For example, "substituted or unsubstituted aryl group having 6 to 40 ring atoms" refers to an aryl group containing 6 to 40 ring atoms, preferably a substituted or unsubstituted aryl group having 6 to 30 ring atoms, more preferably a substituted or unsubstituted aryl group having 6 to 18 ring atoms, particularly preferably a substituted or unsubstituted aryl group having 6 to 14 ring atoms, and the aryl group is optionally further substituted; suitable examples include but are not limited to: phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, fluoranthenyl, triphenylenyl, pyrenyl, perylenyl, tetracenyl, fluorenyl, binaphthylenyl, acenaphthylenyl, and their derivatives. It can be understood that multiple aryl groups can also be interrupted by short non-aromatic units (e.g., <10% non-H atoms such as C, N, or O atoms), specifically such as acenaphthene, fluorene, or 9,9-diarylfluorene, triarylamine, diaryl ether systems should also be included in the definition of aryl groups.

[0036] "Heteroaryl or heteroaromatic group" refers to a group in which at least one carbon atom in the aryl group is replaced by a non-carbon atom, and the non-carbon atom can be an N atom, an O atom, an S atom, etc. For example, "substituted or unsubstituted heteroaryl group having 5 to 40 ring atoms" refers to a heteroaryl group having 5 to 40 ring atoms, preferably a substituted or unsubstituted heteroaryl group having 6 to 30 ring atoms, more preferably a substituted or unsubstituted heteroaryl group having 6 to 18 ring atoms, particularly preferably a substituted or unsubstituted heteroaryl group having 6 to 14 ring atoms, and the heteroaryl group is optionally further substituted. Suitable examples include but are not limited to: thienyl, furyl, pyrrolyl, dioxolyl, triazolyl, imidazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, benzothienyl, benzofuryl, indolyl, pyrroloimidazolyl, pyrrolopyrrolyl, thienopyrrolyl, thienothienyl, furanopyrrolyl, furanofuryl, thienofuryl, benzisoxazolyl, benzisothiazolyl, benzimidazolyl, phthalazinyl, phenanthridinyl, perimidinyl, quinazolinone, dibenzothienyl, dibenzofuryl, carbazolyl, and their derivatives.

[0037] In the present invention, "alkyl" can represent a straight-chain, branched-chain, and / or cyclic alkyl group. The number of carbon atoms in the alkyl group can be 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Phrases containing this term, for example, "C 1-9"Alkyl" refers to an alkyl group containing 1 to 9 carbon atoms, and each occurrence can independently be a C1 alkyl group, C2 alkyl group, C3 alkyl group, C4 alkyl group, C5 alkyl group, C6 alkyl group, C7 alkyl group, C8 alkyl group, or C9 alkyl group. Non-limiting examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, t-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, t-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-t-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, t-octyl, 2-ethyloctyl, 2-butyl octyl, 2-hexyloctyl, 3,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl, n-undecyl, n-dodecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, 2-ethylhexadecyl, 2-butyhexadecyl, 2-hexyhexadecyl, 2-octyhexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-icosyl, 2-ethylicosyl, 2-butylicosyl, 2-hexyicosyl, 2-octyicosyl, n-henicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-nonacosyl, n-triacontyl, etc.

[0038] In the present invention 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.

[0039] In the present invention, a silyl group can be represented by the chemical formula -Si(Y101)(Y102)(Y103), and Y101, Y102, and Y103 can 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 silyl groups include trialkylsilyl and triarylsilyl, and specific examples thereof include trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc., but the examples are not limited thereto.

[0040] "Amino group" refers to derivatives of amines, having the structural feature of the formula -N(X)2, where each "X" is independently H, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclic group, etc. Non-limiting types of amino groups include -NH2, -N(alkyl)2, -NH(alkyl), -N(cycloalkyl)2, -NH(cycloalkyl), -N(heterocyclic group)2, -NH(heterocyclic group), -N(aryl)2, -NH(aryl), -N(alkyl)(aryl), -N(alkyl)(heterocyclic group), -N(cycloalkyl)(heterocyclic group), -N(aryl)(heteroaryl), -N(alkyl)(heteroaryl), etc.

[0041] In the present invention, unless otherwise specifically defined, hydroxyl group refers to -OH, carboxyl group refers to -COOH, carbonyl group refers to -C(=O)-, amino group refers to -NH2, formyl group refers to -C(=O)H, halocarbonyl group refers to -C(=O)Z (where Z represents a halogen), carbamoyl group refers to -C(=O)NH2, isocyanate group refers to -NCO, and isothiocyanate group refers to -NCS.

[0042] The term "alkoxy group" refers to a group having the structure "-O-alkyl", that is, the alkyl group as defined above is connected to other groups via an oxygen atom. Suitable examples of phrases containing this term include, but are not limited to: methoxy (-O-CH3 or -OMe), ethoxy (-O-CH2CH3 or -OEt), and tert-butoxy (-O-C(CH3)3 or -OtBu).

[0043] In the present invention, "*" connected to a single bond represents a connection or fusion site;

[0044] In the present invention, when the connection site is not specified in a group, it means that any optional connection site in the group can be used as the connection site;

[0045] In the present invention, when the fusion site is not specified in a group, it means that any optional fusion site in the group can be used as the fusion site, and preferably two or more sites adjacent to each other in the group are used as the fusion sites;

[0046] In the present invention, when a group contains multiple substituents with the same symbol, each substituent can be the same or different from each other. For example, The 6 Rs on the benzene ring can be the same or different from each other.

[0047] In the present invention, the single bond to which a substituent is attached passes through the corresponding ring, indicating that the substituent can be connected to any optional position of the ring. For example, In, R is connected to any substitutable site of the benzene ring, such as Indicates Can form a fused ring with Any optional substitutable position on.

[0048] In the present invention, "adjacent groups" mean that there is no substitutable site between two substituents.

[0049] In the present invention, "two adjacent Rs form a ring with each other" means a ring system formed by the connection of two adjacent Rs with each other, and the ring system may be selected from an aliphatic hydrocarbon ring, an aliphatic heterocyclic ring, an aromatic hydrocarbon ring or an aromatic heterocyclic ring. Preferably, an aromatic group or a heteroaromatic group with 5 - 10 ring atoms, which may be substituted or unsubstituted, can be formed; more preferably, an aromatic group or a heteroaromatic group with 6 ring atoms, which may be substituted or unsubstituted, is formed. Preferably,

[0050] In the present invention, "their combination", "any combination thereof", "any combination mode thereof", "combination", etc. include all suitable combination modes of any two or any two or more items in the listed groups.

[0051] In the present invention, "further", "even further", "especially", etc. are used for descriptive purposes, indicating differences in content, but should not be construed as limiting the scope of protection of the present invention.

[0052] In the present invention, "optionally", "optional", "option", mean that it may or may not be present, that is, it refers to any one of the two alternative options of "present" or "absent". If "optional" appears multiple times in a technical solution, without special instructions and without contradictions or mutual restrictions, each "optional" is independent of each other.

[0053] In the present invention, for the technical features described in an open-ended manner, it includes a closed technical solution composed of the listed features, and also includes an open-ended technical solution containing the listed features.

[0054] The present invention provides an organic compound having a structure represented by the general formula (1):

[0055]

[0056] Wherein:

[0057] X1, X2, and X3 are each independently selected from CR6 or N, and at least one of X1, X2, and X3 is selected from N;

[0058] Ar1, Ar2, and Ar3 are each independently selected from a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, or an alkyl group having 3 to 30 carbon atoms;

[0059] Each occurrence of R1, R2, R3, R4, R5, and R6 is independently selected from: -H, -D, a linear alkyl group having 1 to 20 C atoms, a linear alkoxy group having 1 to 20 C atoms, a linear thioalkoxy group having 1 to 20 C atoms, a branched alkyl group having 3 to 20 C atoms, a cyclic alkyl group having 3 to 20 C atoms, a branched alkoxy group having 3 to 20 C atoms, a cyclic alkoxy group having 3 to 20 C atoms, a branched thioalkoxy group having 3 to 20 C atoms, a cyclic thioalkoxy group having 3 to 20 C atoms, a silyl group, a keto group having 1 to 20 C atoms, an alkoxycarbonyl group having 2 to 20 C atoms, an aryloxycarbonyl group having 7 to 20 C atoms, an alkenyl group having 1 to 20 C atoms, a carbamoyl group, a halocarbonyl group, a formyl group, a cyano group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, -CF3, -Cl, -Br, -F, a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaryloxy group having 5 to 30 ring atoms, or a combination of these groups;

[0060] m is selected from 1, 2, 3, or 4.

[0061] It is understood that in the present invention, m represents the number of R5 groups attached to the benzene ring.

[0062] In one embodiment, the structure of the silicon-containing organic compound is shown by the general formula (2):

[0063]

[0064] In a specific embodiment, each occurrence of R1, R2, R3, R4, and R5 is independently selected from: -H, -D, a linear alkyl group having 1 to 10 C atoms, a branched alkyl group having 3 to 10 C atoms, a cyclic alkyl group having 3 to 10 C atoms, a silyl group, a cyano group, an isocyano group, a hydroxyl group, a nitro group, -CF3, -Cl, -Br, -F, a substituted or unsubstituted aromatic group having 6 to 20 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 20 ring atoms, or a combination of these groups.

[0065] 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 alkyl group having 3 to 10 C atoms, a cyclic alkyl group having 3 to 10 C atoms, a silyl group, a cyano group, an isocyano group, a hydroxyl group, a nitro group, -CF3, -Cl, -Br, -F, a substituted or unsubstituted aromatic group having 6 to 10 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 10 ring atoms, or a combination of these groups.

[0066] More specifically, each occurrence of R1 and R2 is independently selected from: -H, -D, 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, adamantyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, triazinyl, pyridyl, pyrimidinyl, imidazolyl, furyl, thienyl, benzofuryl, benzothienyl, indolyl, carbazolyl, dibenzothienyl, dibenzofuryl, phenyl-substituted carbazolyl, fluorenyl, fluorenyl substituted with an alkyl group having 1-10 C atoms.

[0067] Preferably, R1 and R2 are selected from the same group.

[0068] In one embodiment, R3 and R4 are independently selected from: -H, -D, a straight-chain alkyl group having 1 to 10 C atoms, a branched alkyl group having 3 to 10 C atoms, a cyclic alkyl group having 3 to 10 C atoms, a substituted or unsubstituted aromatic group having 6 to 10 ring atoms, a substituted or unsubstituted heteroaromatic group having 6 to 10 ring atoms, or a combination of these groups.

[0069] Furthermore, R3 and R4 are independently selected from: -H, -D, a straight-chain alkyl group having 1 to 4 C atoms, a branched alkyl group having 3 to 6 C atoms, a cyclic alkyl group having 3 to 6 C atoms, a substituted or unsubstituted aromatic group having 6 to 10 ring atoms, a substituted or unsubstituted heteroaromatic group having 6 to 10 ring atoms, or a combination of these groups.

[0070] In one embodiment, R3 and R4 are independently selected from: -H, -D, methyl, ethyl, tert-butyl, cyclohexyl, phenyl, pyridyl, pyrimidinyl or naphthyl, or a combination of these groups.

[0071] In one specific embodiment, both R3 and R4 are selected from methyl or phenyl.

[0072] In one embodiment, each occurrence of R5 is independently selected from: -D, a straight-chain alkyl group having 1 to 8 C atoms, a branched-chain alkyl group having 3 to 8 C atoms, a cyclic alkyl group having 3 to 8 C atoms, a silyl group, a cyano group, an isocyano group, a hydroxyl group, a nitro group, -CF3, -Cl, -Br, -F, a phenyl group, a biphenyl group, a pyridyl group, a pyrimidinyl group, or a triazinyl group.

[0073] In one embodiment, X1, X2, and X3 are selected from N or CH.

[0074] In one example, Ar1, Ar2, and Ar3 are each independently selected from a substituted or unsubstituted aromatic group having 6 to 25 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 25 ring atoms.

[0075] In a specific example, each occurrence of Ar1, Ar2, and Ar3 is independently selected from the following groups:

[0076]

[0077] Wherein:

[0078] Each occurrence of X4 is independently selected from CR7 or N;

[0079] Y1 is independently selected from CR8R9, NR 10 , SiR8R9, O, S, Se, S═O, S(═O)2, or PR 10 ;

[0080] R7, R8, R9, R 10 Each occurrence is independently selected from: -H, -D, a straight-chain alkyl group having 1 to 20 C atoms, a straight-chain alkoxy group having 1 to 20 C atoms, a straight-chain thioalkoxy group having 1 to 20 C atoms, a branched or cyclic alkyl group having 3 to 20 C atoms, a branched or cyclic alkoxy group having 3 to 20 C atoms, a branched or cyclic thioalkoxy group having 3 to 20 C atoms, a silyl group, a keto group having 1 to 20 C atoms, an alkoxycarbonyl group having 2 to 20 C atoms, an aryloxycarbonyl group having 7 to 20 C atoms, a cyano group, a carbamoyl group, a halocarbonyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, -CF3, -Cl, -Br, -F, -I, a substituted or unsubstituted aromatic group or heteroaromatic group having 5 to 20 ring atoms, an aryloxy or heteroaryloxy group having 5 to 20 ring atoms, or a combination of these groups.

[0081] It is understood that when X4 is a connection site, X4 is selected from C; when Y1 is a connection site, Y1 is selected from N.

[0082] More specifically, each occurrence of Ar1, Ar2, and Ar3 is independently selected from the following groups:

[0083]

[0084] Where: * represents the connection site.

[0085] In a specific example, R7, R8, R9, and R 10 Each occurrence 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 cyano group, a nitro group, -CF3, -Cl, -Br, -F, -I, a substituted or unsubstituted aromatic group or heteroaromatic group having 6 to 10 ring atoms.

[0086] More specifically, each occurrence of Ar1, Ar2, and Ar3 is independently selected from the following groups:

[0087]

[0088] * represents the connection site.

[0089] In a certain embodiment, Ar3 is selected from Furthermore, Ar3 is selected from In one embodiment, R7 is selected from: -H, -D, a straight-chain alkyl group having 1 to 4 C atoms, a branched or cyclic alkyl group having 3 to 6 C atoms; furthermore, R7 is selected from: -H, -D, methyl, isopropyl, tert-butyl, or phenyl.

[0090] In a specific example, the organic compound of the present invention is a thermally activated delayed fluorescence material.

[0091] Specifically, the organic compound according to the present invention is selected from the following structures but is not limited thereto:

[0092]

[0093]

[0094]

[0095]

[0096] The organic compound of the present invention has a D-A system (i.e., an electron-withdrawing and electron-donating system), and a silicon-containing group is connected to dimethylacridine, which makes the molecular structure of the overall organic compound have better conjugation and planarity, improves the rigidity and stability of the material molecules. As a solubilizing group, diarylsilicon further improves the solubility of the molecule and makes it easier to recrystallize, so that the compound is easier to purify, and thus a compound with higher purity can be obtained. When used as a blue light-emitting material in organic electronic devices, the compound with higher purity can reduce the content of impurities and also reduce the adverse effects of impurities on the device performance and lifespan, thereby improving the light-emitting efficiency and lifespan of the device. In addition, the organic compound of the present invention can be used as a blue light guest material, and by cooperating with a suitable host material, it can improve the light-emitting efficiency and lifespan of the electroluminescent device.

[0097] The organic compound according to the invention can be used as a functional material in organic electronic devices, especially in OLED devices. Organic functional materials can be divided into hole injection materials (HIM), hole transport materials (HTM), electron transport materials (ETM), electron injection materials (EIM), electron blocking materials (EBM), hole blocking materials (HBM), light-emitting guest materials (Emitter), light-emitting host materials (Host) and organic dyes. In a specific example, the organic compound according to the invention is used in the light-emitting layer; preferably, it can be used as the light-emitting guest material of the light-emitting layer in the light-emitting layer.

[0098] In a specific example, the organic compound according to the invention is used as a blue light-emitting material in the light-emitting layer.

[0099] The present invention also provides a mixture, which comprises the above-mentioned organic compound and at least one organic functional material, and 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, light-emitting guest materials, light-emitting host materials or organic dyes. For example, various organic functional materials are described in detail in WO2010135519A1, US20090134784A1 and WO2011110277A1, and the entire contents of these 3 patent documents are hereby incorporated herein by reference.

[0100] The light-emitting guest material is selected from singlet emitters (fluorescent emitters), triplet emitters (phosphorescent emitters) and organic thermally activated delayed fluorescence materials (TADF materials).

[0101] In a specific example, the other organic functional material is selected from the host material; further, the other organic functional material is selected from the blue host material. The weight percentage of the organic compound described in the present invention in the mixture is greater than 0 and less than or equal to 25 wt%, preferably greater than 0 and less than or equal to 15 wt%, and more preferably greater than 0 and less than or equal to 5 wt%.

[0102] The present invention also provides a composition, which comprises the above-mentioned organic compound or the above-mentioned mixture, and at least one organic solvent.

[0103] The at least one organic solvent can be selected from aromatic or heteroaromatic, esters, aromatic ketones or aromatic ethers, aliphatic ketones or aliphatic ethers, alicyclic or olefinic compounds, borate esters or phosphate esters. That is, the solvent contained in the composition of the present invention can be any one of the above-mentioned organic solvents, or a mixed solvent of two or more of them. In a preferred embodiment, the at least one organic solvent contained in the composition of the present invention is selected from aromatic or heteroaromatic solvents.

[0104] Specifically, the aromatic or heteroaromatic-based solvents include but are not limited to: p-diisopropylbenzene, pentylbenzene, tetralin, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylcumene, dipentylbenzene, tripentylbenzene, amyltoluene, 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-isopropylbiphenyl, p-methylcumene, 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, ethyl 2-furoate, etc.

[0105] The ester-based solvents include but are not limited to: alkyl octanoates, alkyl sebacates, alkyl stearates, alkyl benzoates, alkyl phenylacetates, alkyl cinnamates, alkyl oxalates, alkyl maleates, alkanolactones, alkyl oleates, etc. Octyl octanoate, diethyl sebacate, diallyl phthalate, isononyl isononanoate, etc. are particularly preferred.

[0106] Aromatic ketone-based solvents include but are not limited to: 1-tetralone, 2-tetralone, 2-(phenyloxiranyl)tetralone, 6-(methoxy)tetralone, acetophenone, propiophenone, or benzophenone and its derivatives; such as 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylpropiophenone, 3-methylpropiophenone, 2-methylpropiophenone, etc.

[0107] Aromatic ether-based solvents include but are not limited to: 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-ethylbenzyl 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, ethyl-2-naphthyl ether, etc.

[0108] Aliphatic ketone-based solvents include but are 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-pentyl ketone, etc.; aliphatic ether-based solvents include but are not limited to: pentyl 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, tetraethylene glycol dimethyl ether, etc.

[0109] It is understandable that the solvent can be used alone or as a mixture of two or more organic solvents.

[0110] In some embodiments, the composition of the present invention comprises at least one organic compound or mixture as described above, and at least one organic solvent, and may further comprise another organic solvent.

[0111] Another organic solvent includes but is 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, tetralin, decalin, indene.

[0112] In some preferred embodiments, the organic solvents suitable for the present invention are solvents with Hansen solubility parameters in the following ranges:

[0113] δd (dispersion force) is in the range of 17.0 - 23.2 MPa 1 / 2 and especially in the range of 18.5 - 21.0 MPa 1 / 2 ;

[0114] δp (polar force) is in the range of 0.2 - 12.5 MPa 1 / 2 and especially in the range of 2.0 - 6.0 MPa 1 / 2 ;

[0115] δh (hydrogen bonding force) is in the range of 0.9 - 14.2 MPa 1 / 2 and especially in the range of 2.0 - 6.0 MPa 1 / 2 ;

[0116] In some embodiments, for the composition according to the present invention, the boiling point of the organic solvent needs to be considered when selecting it. In at least some embodiments, the boiling point of the organic solvent is ≥150 °C; preferably ≥180 °C; more preferably ≥200 °C; even more preferably ≥250 °C; most preferably ≥275 °C or ≥300 °C. Boiling points within these ranges are beneficial for preventing nozzle blockage of the inkjet printing head.

[0117] It can be understood that the organic solvent can evaporate from the composition system to form a thin film containing the organic compound of the present invention.

[0118] In some embodiments, the composition is a solution. In other embodiments, the composition is a suspension.

[0119] In the composition, the content of the organic compound or mixture can be 0.01 - 10 wt%, preferably 0.1 - 5 wt%, more preferably 0.2 - 5 wt%, and even more preferably 0.25 - 3 wt%.

[0120] The present invention also relates to the use of the composition as a coating or printing ink in the preparation of organic electronic devices. In some embodiments, the composition is used to prepare organic electronic devices by a preparation method of printing or coating. The preparation method of printing or coating can be, but is not limited to, inkjet printing, nozzle printing, letterpress printing, screen printing, gravure printing, dip coating, spin coating, blade coating, roller printing, reverse roller printing, lithographic printing, flexographic printing, rotary printing, spraying, brush coating, pad printing, slot die coating, etc. Preferred are gravure printing, nozzle printing, and inkjet printing.

[0121] The solution or suspension may additionally 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 surface-active compounds, lubricants, wetting agents, dispersants, water repellents, and adhesives. Different printing or coating methods may have different requirements for coatings or printing inks, and the concentration, viscosity, etc. of the solution or suspension may be adjusted accordingly to adapt to different printing or coating methods.

[0122] The present invention also provides an application of the above-mentioned organic compound, mixture, or composition in an organic electronic device. The technical solution is as follows:

[0123] An organic electronic device comprises the above-mentioned organic compound or mixture, or is prepared from the composition.

[0124] Furthermore, an organic electronic device comprises a first electrode, a second electrode, and one or more functional layers located between the first electrode and the second electrode, and the functional layer comprises the above-mentioned organic compound, mixture, or is prepared from the above composition. The functional layer is selected from a hole injection layer (HIL), a hole transport layer (HTL), a light-emitting layer (EML), an electron blocking layer (EBL), an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0125] The organic electronic device may be, but not limited to, an organic light-emitting diode (OLED device), an organic photovoltaic cell (OPV), an organic light-emitting electrochemical cell (OLEEC), an organic field-effect transistor (OFET), an organic light-emitting field-effect transistor, an organic laser, an organic spintronic device, an organic sensor, and an organic plasmon emitting diode, etc. The organic electronic device is preferably an organic electroluminescent device, such as an OLED or an organic light-emitting field-effect transistor.

[0126] The present invention relates to an organic electronic device, which comprises: a cathode, an anode, and at least one functional layer located between the cathode and the anode, and the at least one functional layer comprises the above-mentioned organic compound or mixture, or is prepared from the above composition.

[0127] The functional layer is selected from a hole injection layer (HIL), a hole transport layer (HTL), a light-emitting layer (EML), an electron blocking layer (EBL), an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL). Preferably, the at least one functional layer includes a light-emitting layer.

[0128] In a specific embodiment, the organic electronic device includes an anode, a light-emitting layer, and a cathode that are sequentially stacked. The material of the light-emitting layer contains the organic compound, mixture, or composition prepared from the above-mentioned materials as described above.

[0129] Furthermore, the material of the light-emitting layer includes a light-emitting host material and a light-emitting guest material. The light-emitting guest material is the organic compound, mixture as described above, and the light-emitting host material can be a host material known in the art for the light-emitting layer.

[0130] In one embodiment, the light-emitting host material is selected from anthracene-based organic compounds. The weight percentage of the light-emitting host material in the light-emitting layer is greater than or equal to 75 wt%, preferably greater than or equal to 85 wt%, more preferably greater than or equal to 95 wt%.

[0131] Furthermore, the organic electronic device further includes a substrate. The substrate can be located on the side of the anode away from the light-emitting layer or on the side of the cathode away from the light-emitting layer. The substrate can be opaque or transparent. It can be understood that when the substrate is transparent, the organic electronic device is a transparent light-emitting device. For example, see Bulovic et al., Nature 1996, 380, p29, and Gu et al., Appl. Phys. Lett. 1996, 68, p2606. The substrate can also be rigid or flexible. For example, the material of the substrate can be plastic, metal, semiconductor wafer, or glass. Preferably, the substrate has a smooth surface, and a substrate without surface defects is a particularly ideal choice. In a preferred embodiment, the substrate is a flexible substrate. The material of the flexible substrate can be a polymer film or plastic. The glass transition temperature Tg of the flexible substrate is above 150 °C, preferably exceeding 200 °C, more preferably exceeding 250 °C, and most preferably exceeding 300 °C. As an example, the material of the flexible substrate can be poly(ethylene terephthalate) (PET) or polyethylene glycol (2,6-naphthalene) (PEN).

[0132] Among them, the material of the anode can be an anode material known in the art for organic electronic devices, such as a conductive metal, a conductive metal oxide, or a conductive polymer. In some embodiments, the absolute value of the difference between the work function of the material of the anode and the HOMO energy level or valence band energy level of the light emitter in the light-emitting layer or the p-type semiconductor material serving as a hole injection layer, a hole transport layer, or an electron blocking layer is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. As an example, the material of the anode can be selected from, but not limited to, at least one of Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO, and aluminum-doped zinc oxide (AZO). Other suitable anode materials are known, and those of ordinary skill in the art can easily select and use them. The anode material can 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), etc. In certain embodiments, the anode is pattern-structured. Patterned ITO conductive substrates are commercially available and can be used to fabricate the devices according to the present invention.

[0133] The material of the cathode can be a cathode material known in the art for organic electronic devices, such as a conductive metal or a conductive metal oxide. In some embodiments, the absolute value of the difference between the work function of the material of the cathode and the LUMO energy level or conduction band energy level of the light emitter in the light-emitting layer or the n-type semiconductor material serving as an electron injection layer, an electron transport layer, or a hole blocking layer 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 the cathode of an OLED can potentially be used as the cathode material of the devices of the present invention. As an example, the material of the cathode can be selected from, but not limited to, at least one of Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloy, BaF2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, and ITO. The cathode material can 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), etc.

[0134] Furthermore, the organic electronic device can further include other functional layers, such as a hole injection layer (HIL), a hole transport layer (HTL), an electron blocking layer (EBL), an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL). The materials suitable for these functional layers are described in detail above and in WO2010135519A1, US20090134784A1, and WO2011110277A1. The entire contents of these three patent documents are hereby incorporated herein by reference.

[0135] The organic electronic device according to the present invention has a light emission wavelength between 300 and 1000 nm, preferably between 350 and 900 nm, and more preferably between 400 and 800 nm.

[0136] The present invention also relates to an electronic device comprising the organic electronic device. The present invention relates to the application of the organic electronic device in various electronic devices. The electronic device may be, but is not limited to, a display device, a lighting device, a light source, a sensor, etc. Specific embodiments

[0138] The present invention is described in detail below by specific examples, which are only partial examples of the present invention and are not intended to limit the present invention. The raw materials used in the following examples, unless otherwise specified, are all commercially available products.

[0139] Among them, some reagents are as follows: t-BuONa: sodium tert-butoxide; t-Bu3P: tri-tert-butylphosphine; Pd2(dba)3: tridibenzylideneacetone dipalladium; BuLi: n-butyllithium; THF: tetrahydrofuran; Toluene: toluene; DMF: N,N-dimethylformamide; DCM: dichloromethane; Pd(PPh3)4: tetrakis(triphenylphosphine)palladium; AcOK: potassium acetate.

[0140] Example 1

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

[0142]

[0143] Synthesis of intermediate 1-1: Weigh dimethylacridine (11.4 g, 54.6 mmol), bromobenzene (17 g, 109 mmol), Pd2(dba)3 (1.48 g, 1.6 mmol), t-Bu3P (0.39 g, 1.94 mmol), sodium tert-butoxide (15.5 g, 162 mmol) in a 500 mL three-necked flask, add 200 ml of toluene, replace nitrogen, react at 80 ° C for 12 h. Spin dry, wash with water, and column chromatography (eluent: PE) to obtain a white solid with a yield of 72%.

[0144] Synthesis of intermediate 1-2: Place intermediate 1-1 (12.11 g, 42.5 mmol) in a 500 ml two-necked bottle, add 200 ml of DMF until the solid is completely dissolved, weigh NBS (7.5 g, 42.5 mmol) and place it in a constant pressure dropping funnel, dissolve it in 100 ml of DMF, slowly add dropwise, and react at room temperature for 12 hours. Spin dry, wash with water, and column chromatography (eluent: PE) to obtain a white solid with a yield of 87%.

[0145] Synthesis of Intermediate 1-3: Prepare a dry 500 mL three-necked flask, set up the reaction apparatus, evacuate it, and introduce nitrogen; keep the nitrogen flowing in the reaction flask, weigh 1,4-dibromobenzene (10 g, 42.6 mmol), and add THF (250 ml), evacuate and introduce nitrogen in a cycle three times, cool down to -78 °C; slowly drip n-butyllithium solution (17.4 ml, 42.6 mmol) into the reaction flask, after reacting at -78 °C for 30 min, quickly add dimethoxydiphenylsilane (10.4 g, 42.6 mmol). Let the reaction system slowly rise to room temperature and react for 12 h. Add water, extract with DCM, after evaporating the solvent, obtain a colorless oily substance by column chromatography (eluent is PE), and the yield is 41%.

[0146] Synthesis of Intermediate 1-4: Prepare a dry 250 mL three-necked flask, set up the reaction apparatus, evacuate it, and introduce nitrogen; keep the nitrogen flowing in the reaction flask, weigh Intermediate 1-2 (3.3 g, 8.9 mmol), and add THF (100 ml), evacuate and introduce nitrogen in a cycle three times, cool down to -78 °C; slowly drip n-butyllithium solution (3.6 ml, 8.9 mmol) into the reaction flask, after reacting at -78 °C for 60 min, quickly add Intermediate 1-3 (3.3 g, 8.9 mmol). Let the reaction system slowly rise to room temperature and react for 12 h. Add water, extract with DCM, after evaporating the solvent, grind with PE to obtain a white solid. The yield is 58%.

[0147] Synthesis of Intermediate 1-5: Weigh Intermediate 1-4 (6.21 g, 10 mmol), (Bpin)2 (3.8 g, 15 mmol), AcOK (9.8 g, 100 mmol), Pd(dppf)Cl2 (0.74 g, 1.0 mmol), t-Bu3P (0.39 g, 1.94 mmol) into a 250 mL three-necked flask, add 100 ml of 1,4-dioxane, displace nitrogen, and react at 100 °C for 12 h. Evaporate to dryness, wash with water, and obtain a colorless oily substance by column chromatography (eluent is PE:DCM = 5:1), and the yield is 63%.

[0148] Synthesis of Compound 1: Weigh Intermediate 1-5 (6.21 g, 9.3 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (3.8 g, 14 mmol), K2CO3 (12.8 g, 93 mmol), Pd(PPh3)4 (1.1 g, 0.93 mmol) into a 250 mL three-necked flask, add 100 ml of toluene, 50 ml of ethanol, 50 ml of water, displace nitrogen, and react at 100 °C for 12 h. Evaporate to dryness, wash with water, and obtain a white solid by column chromatography (eluent is PE:DCM = 3:1), and the yield is 57%. MS(ASAP) = 774.7.

[0149] Example 2

[0150] The synthetic route of Compound 2 in this example is as follows:

[0151]

[0152] Synthesis of Intermediate 2-1: Prepare a dry 500 mL three-necked flask, set up the reaction apparatus, evacuate it, and purge with nitrogen; keep the nitrogen flowing in the reaction flask, weigh 1,3-dibromobenzene (10 g, 42.6 mmol), and add THF (250 ml), evacuate and purge with nitrogen three times, cool down to -78 °C; slowly drip n-butyllithium solution (17.4 ml, 42.6 mmol) into the reaction flask, after reacting at -78 °C for 30 min, quickly add dimethoxydiphenylsilane (10.4 g, 42.6 mmol). Let the reaction system slowly warm up to room temperature and react for 12 h. Add water, extract with DCM, after evaporating the solvent, obtain a colorless oil by column chromatography (the eluent is PE), and the yield is 35%.

[0153] Synthesis of Intermediate 2-2: Prepare a dry 250 mL three-necked flask, set up the reaction apparatus, evacuate it, and purge with nitrogen; keep the nitrogen flowing in the reaction flask, weigh 1-2 (3.3 g, 8.9 mmol), and add THF (100 ml), evacuate and purge with nitrogen three times, cool down to -78 °C; slowly drip n-butyllithium solution (3.6 ml, 8.9 mmol) into the reaction flask, after reacting at -78 °C for 60 min, quickly add Intermediate 2-1 (3.3 g, 8.9 mmol). Let the reaction system slowly warm up to room temperature and react for 12 h. Add water, extract with DCM, after evaporating the solvent, grind with PE to obtain a white solid. The yield is 57%.

[0154] Synthesis of Intermediate 2-3: Weigh Intermediate 2-2 (6.21 g, 10 mmol), (Bpin)2 (3.8 g, 15 mmol), AcOK (9.8 g, 100 mmol), Pd(dppf)Cl2 (0.74 g, 1.0 mmol), t-Bu3P (0.39 g, 1.94 mmol) into a 250 mL three-necked flask, add 100 ml of 1,4-dioxane, displace nitrogen, and react at 100 °C for 12 h. Evaporate to dryness, wash with water, and obtain a colorless oil by column chromatography (the eluent is PE:DCM = 5:1), and the yield is 73%.

[0155] Synthesis of Compound 2: Weigh intermediate 2-3 (6.24 g, 9.3 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (3.8 g, 14 mmol), K2CO3 (12.8 g, 93 mmol), and Pd(PPh3)4 (1.1 g, 0.93 mmol) into a 250 mL three-necked flask. Add 100 ml of toluene, 50 ml of ethanol, and 50 ml of water. Replace the nitrogen, and react at 100 °C for 12 h. Rotate to dryness, wash with water, and perform column chromatography (eluent: PE:DCM = 3:1) to obtain a white solid with a yield of 50%. MS (ASAP) = 774.8.

[0156] Example 3

[0157] The synthesis route of Compound 3 in this example is as follows:

[0158]

[0159] Synthesis of intermediate 3-3: Under a nitrogen atmosphere, add 20 mmol of intermediate 3-1 and 150 mL of anhydrous tetrahydrofuran solvent to a 500 mL two-necked flask, stir to dissolve, cool down to -78 °C, slowly add 60 mmol of n-butyllithium dropwise, maintain the temperature, and continue to stir and react for 2 hours. Transfer the reaction solution to a 100 mL anhydrous tetrahydrofuran solution containing 10 mmol of intermediate 3-2, stir and react at room temperature for 4 hours, quench with water, rotate and evaporate most of the solvent from the reaction solution, dissolve with dichloromethane and wash 3 times with water, collect the organic phase, and the yield is 78%.

[0160] Synthesis of intermediate 3-5: Weigh 10 mmol of intermediate 3-3, 10 mmol of intermediate 3-4, 0.1 mmol of Pd2(dba)3, 0.2 mmol of t-Bu3P, and 20 mmol of sodium tert-butoxide into a 500 mL three-necked flask. Add 200 ml of toluene, replace the nitrogen, and react at 80 °C for 12 h. Rotate to dryness, wash with water, and perform column chromatography (eluent: PE) to obtain a white solid with a yield of 71%.

[0161] Synthesis of intermediate 3-6: Place 10 mmol of intermediate 3-5 in a 500 ml two-necked flask, add 200 ml of DMF until the solid is completely dissolved. Weigh 10 mmol of NBS and place it in a constant pressure dropping funnel, dissolve it with 100 ml of DMF, slowly add it dropwise, and react at room temperature for 12 h. Rotate to dryness, wash with water, and perform column chromatography (eluent: PE) to obtain a white solid with a yield of 85%.

[0162] Synthesis of Intermediate 3-8: Prepare a dry 500 mL three-necked flask, set up the reaction apparatus, evacuate it, and purge with nitrogen; keep the nitrogen flowing in the reaction flask, weigh 10 mmol of Intermediate 3-6, add THF (250 mL), evacuate and purge with nitrogen three times, cool down to -78 °C; slowly add 20 mmol of n-butyllithium solution dropwise to the reaction flask, after reacting at -78 °C for 30 min, quickly add 10 mmol of Intermediate 3-7. Let the reaction system slowly warm up to room temperature and react for 12 h. Add water, extract with DCM, after rotary evaporation of the solvent, obtain a colorless oil by column chromatography (eluent is PE), with a yield of 42%.

[0163] Synthesis of Intermediate 3-10: Prepare a dry 500 mL three-necked flask, set up the reaction apparatus, evacuate it, and purge with nitrogen; keep the nitrogen flowing in the reaction flask, weigh 10 mmol of Intermediate 3-9, add THF (250 mL), evacuate and purge with nitrogen three times, cool down to -78 °C; slowly add 20 mmol of n-butyllithium solution dropwise to the reaction flask, after reacting at -78 °C for 30 min, quickly add 10 mmol of Intermediate 3-8. Let the reaction system slowly warm up to room temperature and react for 12 h. Add water, extract with DCM, after rotary evaporation of the solvent, obtain a colorless oil by column chromatography (eluent is PE), with a yield of 47%.

[0164] Synthesis of Compound 3: Add magnesium chips (50 mmol), 200 mL of THF and 5 iodine crystals into a dry and anhydrous two-necked flask, after purging with nitrogen three times, slowly add the THF solution of Intermediate 3-10 (10 mmol). After initiation, after the system returns to room temperature for 0.5 h, add the system solution dropwise into the THF solution of Intermediate 3-11 (10 mmol), and stir at room temperature. During the treatment, add water to quench the Grignard reagent. After the temperature stabilizes, then extract, wash and separate the liquid, collect the organic phase, and obtain Compound 3 through drying, concentration under reduced pressure, column chromatography and recrystallization, with a yield of 52%. MS (ASAP) = 977.6.

[0165] Example 4

[0166] The synthetic route of Compound 4 in this example is as follows:

[0167]

[0168] Synthesis of Intermediate 4-3: Weigh 10 mmol of Intermediate 4-1, 10 mmol of Intermediate 4-2, 0.1 mmol of Pd2(dba)3, 0.2 mmol of t-Bu3P, and 20 mmol of sodium tert-butoxide in a 500 mL three-necked flask, add 200 mL of toluene, displace nitrogen, and react at 80 °C for 12 h. Rotary evaporate, wash with water, and obtain a white solid by column chromatography (eluent is PE), with a yield of 65%.

[0169] Synthesis of Intermediate 4-4: Place 10 mmol of Intermediate 4-3 in a 500-ml two-necked flask, add 200 ml of DMF until all the solids are dissolved. Weigh 10 mmol of NBS and place it in a constant-pressure dropping funnel, dissolve it with 100 ml of DMF, and slowly add it dropwise. React at room temperature for 12 h. Rotavapor to dryness, wash with water, and perform column chromatography (eluent: PE) to obtain a white solid, with a yield of 79%.

[0170] Synthesis of Intermediate 4-6: Prepare a dry 500-mL three-necked flask, set up the reaction apparatus, evacuate, and purge with nitrogen. Keep the nitrogen flowing in the reaction flask. Weigh 10 mmol of Intermediate 4-4 and add THF (250 ml). Evacuate and purge with nitrogen three times, and cool to -78 °C. Slowly add 20 mmol of n-butyllithium solution dropwise to the reaction flask. After reacting at -78 °C for 30 min, quickly add 10 mmol of Intermediate 4-5. Let the reaction system slowly warm up to room temperature and react for 12 h. Add water, extract with DCM. After rotary evaporation of the solvent, perform column chromatography (eluent: PE) to obtain a colorless oil, with a yield of 47%.

[0171] Synthesis of Intermediate 4-7: Prepare a dry 500-mL three-necked flask, set up the reaction apparatus, evacuate, and purge with nitrogen. Keep the nitrogen flowing in the reaction flask. Weigh 10 mmol of Intermediate 3-9 and add THF (250 ml). Evacuate and purge with nitrogen three times, and cool to -78 °C. Slowly add 20 mmol of n-butyllithium solution dropwise to the reaction flask. After reacting at -78 °C for 30 min, quickly add 10 mmol of Intermediate 4-6. Let the reaction system slowly warm up to room temperature and react for 12 h. Add water, extract with DCM. After rotary evaporation of the solvent, perform column chromatography (eluent: PE) to obtain a colorless oil, with a yield of 41%.

[0172] Synthesis of Compound 4: Add magnesium chips (50 mmol), 200 ml of THF, and 5 iodine crystals to a dry and anhydrous two-necked flask. After purging with nitrogen three times, slowly add a THF solution of 10 mmol of Intermediate 4-7 dropwise. After initiation, wait for 0.5 h until the system returns to room temperature, then add the system solution dropwise to a THF solution of 10 mmol of Intermediate 4-8 and stir at room temperature. During the treatment, add water to quench the Grignard reagent. After the temperature stabilizes, then extract, wash, and separate the layers. Collect the organic phase, and obtain Compound 4 through drying, concentration under reduced pressure, column chromatography, and recrystallization, with a yield of 64%. MS (ASAP) = 1001.8.

[0173] Example 5

[0174] The synthesis route of Compound 5 in this example is as follows:

[0175]

[0176] Synthesis of Compound 5: In a dry and anhydrous two-necked flask, add magnesium shavings (50 mmol), 200 ml of THF, and 5 grains of I2. After purging with nitrogen three times, slowly dropwise add a THF solution of 10 mmol of Intermediate 1-4. After initiation, when the system returns to room temperature for 0.5 h, dropwise add the system solution to a THF solution of 10 mmol of Intermediate 5-1, and stir at room temperature. During the treatment, add water to quench the Grignard reagent. After the temperature stabilizes, then extract and wash with water and separate the liquid phases. Collect the organic phase, and obtain Compound 5 through drying, concentration under reduced pressure, column chromatography, and recrystallization. Yield: 77%. MS (ASAP) = 954.7.

[0177] Example 6

[0178] The synthetic route of Compound 6 in this example is as follows:

[0179]

[0180] Synthesis of Compound 6: In a dry and anhydrous two-necked flask, add magnesium shavings (50 mmol), 200 ml of THF, and 5 grains of I2. After purging with nitrogen three times, slowly dropwise add a THF solution of 10 mmol of Intermediate 1-4. After initiation, when the system returns to room temperature for 0.5 h, dropwise add the system solution to a THF solution of 10 mmol of Intermediate 6-1, and stir at room temperature. During the treatment, add water to quench the Grignard reagent. After the temperature stabilizes, then extract and wash with water and separate the liquid phases. Collect the organic phase, and obtain Compound 6 through drying, concentration under reduced pressure, column chromatography, and recrystallization. Yield: 81%. MS (ASAP) = 966.8.

[0181] Example 7

[0182] The synthetic route of 7 in this example is as follows:

[0183]

[0184] Synthesis of Intermediate 7-2: Under a nitrogen atmosphere, add 20 mmol of Intermediate 7-1 and 150 mL of anhydrous tetrahydrofuran solvent to a 500 mL two-necked flask, stir to dissolve, cool down to -78 °C, slowly dropwise add 60 mmol of n-butyllithium, maintain the temperature, and continue to stir and react for 2 hours. Transfer the reaction solution to a 100 mL anhydrous tetrahydrofuran solution containing 10 mmol of Intermediate 3-2, and stir and react at room temperature for 4 hours. Add water to quench, rotary evaporate most of the solvent from the reaction solution, dissolve with dichloromethane and wash 3 times with water, collect the organic phase, and the yield is 71%.

[0185] Synthesis of Intermediate 7-3: Weigh 10 mmol of Intermediate 7-2, 10 mmol of Intermediate 3-1, 0.1 mmol of Pd2(dba)3, 0.2 mmol of t-Bu3P, and 20 mmol of sodium tert-butoxide into a 500 mL three-necked flask. Add 200 ml of toluene, displace nitrogen, and react at 80 °C for 12 h. Rotavapor to dryness, wash with water, and perform column chromatography (eluent: PE) to obtain a white solid with a yield of 81%.

[0186] Synthesis of Intermediate 7-4: Place 10 mmol of Intermediate 7-3 in a 500 ml two-necked flask, add 200 ml of DMF until the solid completely dissolves. Weigh 10 mmol of NBS into a constant pressure dropping funnel, dissolve it with 100 ml of DMF, slowly add dropwise, and react at room temperature for 12 h. Rotavapor to dryness, wash with water, and perform column chromatography (eluent: PE) to obtain a white solid with a yield of 87%.

[0187] Synthesis of Intermediate 7-5: Prepare a dry 500 mL three-necked flask, set up the reaction apparatus, evacuate, and introduce nitrogen; keep the nitrogen flowing in the reaction flask. Weigh 10 mmol of Intermediate 7-4 and add THF (250 ml), evacuate and introduce nitrogen three times in a cycle, cool down to -78 °C; slowly add dropwise 20 mmol of n-butyllithium solution to the reaction flask, react at -78 °C for 30 min, and then quickly add 10 mmol of Intermediate 4-5. Let the reaction system slowly warm up to room temperature and react for 12 h. Add water, extract with DCM, rotavapor the solvent, and perform column chromatography (eluent: PE) to obtain a colorless oil with a yield of 37%.

[0188] Synthesis of Intermediate 7-6: Prepare a dry 500 mL three-necked flask, set up the reaction apparatus, evacuate, and introduce nitrogen; keep the nitrogen flowing in the reaction flask. Weigh 10 mmol of Intermediate 3-9 and add THF (250 ml), evacuate and introduce nitrogen three times in a cycle, cool down to -78 °C; slowly add dropwise 20 mmol of n-butyllithium solution to the reaction flask, react at -78 °C for 30 min, and then quickly add 10 mmol of Intermediate 7-5. Let the reaction system slowly warm up to room temperature and react for 12 h. Add water, extract with DCM, rotavapor the solvent, and perform column chromatography (eluent: PE) to obtain a colorless oil with a yield of 59%.

[0189] Synthesis of Compound 7: Add magnesium shavings (50 mmol), 200 ml of THF and 5 grains of I2 into a dry and anhydrous two-necked flask. After purging with nitrogen three times, slowly add a THF solution of intermediate 7-7 (10 mmol). After initiation, when the system returns to room temperature for 0.5 h, add the system solution dropwise into a THF solution of intermediate 7-6 (10 mmol), and stir at room temperature. During the treatment, add water to quench the Grignard reagent. After the temperature stabilizes, extract, wash and separate the liquid, collect the organic phase, and obtain Compound 7 through drying, concentration under reduced pressure, column chromatography and recrystallization. Yield: 67%. MS (ASAP) = 948.9.

[0190] Example 8

[0191] The synthetic route of Compound 8 in this example is as follows:

[0192]

[0193] Synthesis of Intermediate 8-2: Under a nitrogen atmosphere, add 20 mmol of Intermediate 8-1 and 150 mL of anhydrous tetrahydrofuran solvent into a 500 mL two-necked flask, stir to dissolve, cool down to -78 °C, slowly add 60 mmol of n-butyllithium, maintain the temperature, and continue stirring and reacting for 2 hours. Transfer the reaction solution to a 100 mL anhydrous tetrahydrofuran solution containing 10 mmol of Intermediate 3-2, and stir and react at room temperature for 4 hours. Add water to quench, rotary evaporate most of the solvent from the reaction solution, dissolve with dichloromethane and wash 3 times, collect the organic phase, and the yield is 74%.

[0194] Synthesis of Intermediate 8-4: Weigh 10 mmol of Intermediate 8-2, 10 mmol of Intermediate 8-3, 0.1 mmol of Pd2(dba)3, 0.2 mmol of t-Bu3P, and 20 mmol of sodium tert-butoxide into a 500 mL three-necked flask, add 200 ml of toluene, displace nitrogen, and react at 80 °C for 12 h. Spin dry, wash with water, and perform column chromatography (the eluent is PE) to obtain a white solid. Yield: 76%.

[0195] Synthesis of Intermediate 8-5: Place 10 mmol of Intermediate 8-4 in a 500 ml two-necked flask, add 200 ml of DMF until the solid is completely dissolved. Weigh 10 mmol of NBS and place it in a constant pressure dropping funnel, dissolve it with 100 ml of DMF, slowly add it dropwise, and react at room temperature for 12 h. Spin dry, wash with water, and perform column chromatography (the eluent is PE) to obtain a white solid. Yield: 86%.

[0196] Synthesis of Intermediate 8-6: Prepare a dry 500 mL three-necked flask, set up the reaction apparatus, evacuate it, and introduce nitrogen; keep the nitrogen flowing in the reaction flask, weigh 10 mmol of Intermediate 8-5, and add THF (250 mL). Evacuate and introduce nitrogen three times in a cycle, cool down to -78 °C; slowly add 20 mmol of n-butyllithium solution dropwise to the reaction flask. After reacting at -78 °C for 30 min, quickly add 10 mmol of Intermediate 4-5. Let the reaction system slowly warm up to room temperature and react for 12 h. Add water, extract with DCM, and after rotary evaporation of the solvent, obtain a colorless oily substance by column chromatography (the eluent is PE), with a yield of 51%.

[0197] Synthesis of Intermediate 8-7: Prepare a dry 500 mL three-necked flask, set up the reaction apparatus, evacuate it, and introduce nitrogen; keep the nitrogen flowing in the reaction flask, weigh 10 mmol of Intermediate 3-9, and add THF (250 mL). Evacuate and introduce nitrogen three times in a cycle, cool down to -78 °C; slowly add 20 mmol of n-butyllithium solution dropwise to the reaction flask. After reacting at -78 °C for 30 min, quickly add 10 mmol of Intermediate 8-6. Let the reaction system slowly warm up to room temperature and react for 12 h. Add water, extract with DCM, and after rotary evaporation of the solvent, obtain a colorless oily substance by column chromatography (the eluent is PE), with a yield of 61%.

[0198] Synthesis of Compound 8: Add magnesium chips (50 mmol), 200 mL of THF, and 5 iodine crystals to a dry and anhydrous two-necked flask. After purging with nitrogen three times, slowly add the THF solution of Intermediate 8-8 (10 mmol). After initiation, after the system returns to room temperature for 0.5 h, add the solution of the system dropwise to the THF solution of Intermediate 8-7 (10 mmol), and stir at room temperature. During the treatment, add water to quench the Grignard reagent. After the temperature stabilizes, then extract, wash, and separate the liquid. Collect the organic phase, and obtain Compound 8 through drying, concentration under reduced pressure, column chromatography, and recrystallization, with a yield of 65%. MS (ASAP) = 928.7.

[0199] Example 9

[0200] The synthesis route of Compound 9 in this example is as follows:

[0201]

[0202] Synthesis of Intermediate 9-1: Weigh 10 mmol of Intermediate 3-3, 10 mmol of Intermediate 3-1, 0.1 mmol of Pd2(dba)3, 0.2 mmol of t-Bu3P, and 20 mmol of sodium tert-butoxide into a 500 mL three-necked flask, add 200 mL of toluene, displace nitrogen, and react at 80 °C for 12 h. Rotary evaporate, wash with water, and obtain a white solid by column chromatography (the eluent is PE), with a yield of 67%.

[0203] Synthesis of Intermediate 9-2: Place 10 mmol of Intermediate 9-1 in a 500-ml two-necked flask, add 200 ml of DMF until all the solids are dissolved. Weigh 10 mmol of NBS and place it in a constant-pressure dropping funnel, dissolve it with 100 ml of DMF, and slowly add it dropwise. React at room temperature for 12 h. Spin-dry, wash with water, and perform column chromatography (the eluent is PE) to obtain a white solid, with a yield of 83%.

[0204] Synthesis of Intermediate 9-3: Prepare a dry 500-mL three-necked flask, set up the reaction apparatus, evacuate, and purge with nitrogen; keep the nitrogen flowing in the reaction flask, weigh 10 mmol of Intermediate 9-2, and add THF (250 ml). Evacuate and purge with nitrogen three times, and cool to -78 °C; slowly add 20 mmol of n-butyllithium solution dropwise to the reaction flask. After reacting at -78 °C for 30 min, quickly add 10 mmol of Intermediate 4-5. Let the reaction system slowly warm up to room temperature and react for 12 h. Add water, extract with DCM. After spinning-drying the solvent, perform column chromatography (the eluent is PE) to obtain a colorless oil, with a yield of 57%.

[0205] Synthesis of Intermediate 9-4: Prepare a dry 500-mL three-necked flask, set up the reaction apparatus, evacuate, and purge with nitrogen; keep the nitrogen flowing in the reaction flask, weigh 10 mmol of Intermediate 3-9, and add THF (250 ml). Evacuate and purge with nitrogen three times, and cool to -78 °C; slowly add 20 mmol of n-butyllithium solution dropwise to the reaction flask. After reacting at -78 °C for 30 min, quickly add 10 mmol of Intermediate 9-3. Let the reaction system slowly warm up to room temperature and react for 12 h. Add water, extract with DCM. After spinning-drying the solvent, perform column chromatography (the eluent is PE) to obtain a colorless oil, with a yield of 56%.

[0206] Synthesis of Compound 9: Add magnesium shavings (50 mmol), 200 ml of THF, and 5 grains of I2 to a dry and water-free two-necked flask. After purging with nitrogen three times, slowly add the THF solution of Intermediate 9-4 (10 mmol). After initiation, wait for 0.5 h until the system returns to room temperature, then add the system solution dropwise to the THF solution of Intermediate 9-5 (10 mmol), and stir at room temperature. During the treatment, add water to quench the Grignard reagent. After the temperature stabilizes, then extract, wash, and separate the layers. Collect the organic phase, and obtain Compound 9 through drying, concentration under reduced pressure, column chromatography, and recrystallization. The yield is 51%. MS (ASAP) = 1010.7.

[0207] Example 10

[0208] The synthetic route of Compound 10 in this example is as follows:

[0209]

[0210] Synthesis of Compound 10: Add magnesium shavings (50 mmol), 200 ml of THF, and 5 grains of I2 into a dry and anhydrous two-necked flask. After purging with nitrogen three times, slowly drip the THF solution of intermediate 9 (410 mmol). After initiation, wait for the system to return to room temperature for 0.5 h, then drip the system solution into the THF solution of intermediate 10 (110 mmol), and stir at room temperature. During the treatment, add water to quench the Grignard reagent. After the temperature stabilizes, then extract, wash with water, separate the liquid, collect the organic phase, and obtain Compound 10 through drying, concentration under reduced pressure, column chromatography, and recrystallization. Yield: 65%. MS (ASAP) = 1074.9.

[0211] Example 11

[0212] The synthetic route of Compound 11 in this example is as follows:

[0213]

[0214] Synthesis of Intermediate 11-2: Prepare a dry 500 mL three-necked flask, set up the reaction apparatus, evacuate, and purge with nitrogen; keep nitrogen flowing in the reaction flask, weigh intermediate 1-2 (10 mmol), and add THF (250 ml), evacuate and purge with nitrogen three times, cool down to -78 °C; slowly drip 20 mmol of n-butyllithium solution into the reaction flask. After reacting at -78 °C for 30 min, quickly add intermediate 11-1 (10 mmol). Let the reaction system slowly rise to room temperature and react for 12 h. Add water, extract with DCM, and after evaporating the solvent, obtain a colorless oil by column chromatography (eluent: PE), with a yield of 52%.

[0215] Synthesis of Intermediate 11-3: Prepare a dry 500 mL three-necked flask, set up the reaction apparatus, evacuate, and purge with nitrogen; keep nitrogen flowing in the reaction flask, weigh intermediate 3-9 (10 mmol), and add THF (250 ml), evacuate and purge with nitrogen three times, cool down to -78 °C; slowly drip 20 mmol of n-butyllithium solution into the reaction flask. After reacting at -78 °C for 30 min, quickly add intermediate 11-2 (10 mmol). Let the reaction system slowly rise to room temperature and react for 12 h. Add water, extract with DCM, and after evaporating the solvent, obtain a colorless oil by column chromatography (eluent: PE), with a yield of 39%.

[0216] Synthesis of Compound 11: Add magnesium chips (50 mmol), 200 ml of THF and 5 grains of I2 into a dry two-necked flask. After purging with nitrogen three times, slowly dropwise add a THF solution of Intermediate 11-3 (10 mmol). After initiation, wait for the system to return to room temperature for 0.5 h, then dropwise add the system solution into a THF solution of Intermediate 11-4 (10 mmol), and stir at room temperature. During the treatment, add water to quench the Grignard reagent. After the temperature stabilizes, then extract, wash and separate the liquid. Collect the organic phase, and obtain Compound 11 through drying, concentration under reduced pressure, column chromatography and recrystallization. Yield: 58%. MS (ASAP) = 1012.7.

[0217] Example 12

[0218] The synthetic route of Compound 12 in this example is as follows:

[0219]

[0220] Synthesis of Intermediate 12-1: Prepare a dry 500 mL three-necked flask, set up the reaction device, evacuate and purge with nitrogen; keep nitrogen flowing in the reaction flask, weigh Intermediate 1-2 (10 mmol), and add THF (250 ml), evacuate and purge with nitrogen three times, cool down to -78 °C; slowly dropwise add 20 mmol of n-butyllithium solution to the reaction flask. After reacting at -78 °C for 30 min, quickly add Intermediate 4-5 (10 mmol). Let the reaction system slowly rise to room temperature and react for 12 h. Add water, extract with DCM, and after evaporating the solvent, obtain a colorless oil by column chromatography (eluent: PE), with a yield of 56%.

[0221] Synthesis of Intermediate 12-3: Prepare a dry 500 mL three-necked flask, set up the reaction device, evacuate and purge with nitrogen; keep nitrogen flowing in the reaction flask, weigh Intermediate 12-2 (10 mmol), and add THF (250 ml), evacuate and purge with nitrogen three times, cool down to -78 °C; slowly dropwise add 20 mmol of n-butyllithium solution to the reaction flask. After reacting at -78 °C for 30 min, quickly add Intermediate 12-1 (10 mmol). Let the reaction system slowly rise to room temperature and react for 12 h. Add water, extract with DCM, and after evaporating the solvent, obtain a colorless oil by column chromatography (eluent: PE), with a yield of 35%.

[0222] Synthesis of Compound 12: Add magnesium chips (50 mmol), 200 ml of THF, and 5 grains of I2 into a dry and anhydrous two-necked flask. After purging with nitrogen three times, slowly dropwise add a THF solution of Intermediate 12-3 (10 mmol). After initiation, when the system returns to room temperature for 0.5 h, drop the system solution into a THF solution of Intermediate 12-4 (10 mmol), and stir at room temperature. During the treatment, add water to quench the Grignard reagent. After the temperature stabilizes, then extract, wash with water, separate the layers, collect the organic phase, and obtain Compound 12 through drying, concentration under reduced pressure, column chromatography, and recrystallization. Yield: 68%. MS (ASAP) = 901.8.

[0223] Example 13

[0224] The synthetic route of Compound 13 in this example is as follows:

[0225]

[0226] Synthesis of Intermediate 13-2: Weigh Intermediate 4-1 (10 mmol), Intermediate 13-1 (10 mmol), Pd2(dba)3 (0.1 mmol), t-Bu3P (0.2 mmol), and sodium tert-butoxide (20 mmol) into a 500 mL three-necked flask, add 200 ml of toluene, displace nitrogen, and react at 80 °C for 12 h. Spin-dry, wash with water, and perform column chromatography (eluent: PE) to obtain a white solid. Yield: 73%.

[0227] Synthesis of Intermediate 13-3: Place Intermediate 13-2 (10 mmol) in a 500 ml two-necked flask, add 200 ml of DMF until the solid completely dissolves. Weigh NBS (10 mmol) and place it in a constant pressure dropping funnel, dissolve it with 100 ml of DMF, slowly dropwise add it, and react at room temperature for 12 h. Spin-dry, wash with water, and perform column chromatography (eluent: PE) to obtain a white solid. Yield: 76%.

[0228] Synthesis of Intermediate 13-4: Prepare a dry 500 mL three-necked flask, set up the reaction device, evacuate, and purge with nitrogen; keep the nitrogen flowing in the reaction flask, weigh Intermediate 13-3 (10 mmol), and add THF (250 ml), evacuate and purge with nitrogen three times, cool down to -78 °C; slowly dropwise add 20 mmol of n-butyllithium solution to the reaction flask, react at -78 °C for 30 min, and then quickly add Intermediate 4-5 (10 mmol). Let the reaction system slowly rise to room temperature and react for 12 h. Add water, extract with DCM, spin-dry the solvent, and then perform column chromatography (eluent: PE) to obtain a colorless oil. Yield: 39%.

[0229] Synthesis of Intermediate 13-5: Prepare a dry 500 mL three-necked flask, set up the reaction apparatus, evacuate it, and then introduce nitrogen; keep the nitrogen flowing in the reaction flask, weigh 10 mmol of Intermediate 3-9, add THF (250 mL), evacuate and introduce nitrogen three times in a cycle, and cool down to -78 °C; slowly drip 20 mmol of n-butyllithium solution into the reaction flask, after reacting at -78 °C for 30 min, quickly add 10 mmol of Intermediate 13-4. Let the reaction system slowly rise to room temperature and react for 12 h. Add water, extract with DCM, after rotary evaporation of the solvent, obtain a colorless oily substance by column chromatography (eluent: PE), with a yield of 50%.

[0230] Synthesis of Compound 13: Add magnesium chips (50 mmol), 200 mL of THF and 5 grains of I2 into a dry and water-free two-necked flask, after replacing the gas with nitrogen three times, slowly drip the THF solution of 10 mmol of Intermediate 13-5. After initiation, after the system returns to room temperature for 0.5 h, drip the system solution into the THF solution of 10 mmol of Intermediate 13-6, and stir at room temperature. During the treatment, add water to quench the Grignard reagent. After the temperature stabilizes, then extract, wash and separate the liquid, collect the organic phase, and obtain Compound 13 through drying, concentration under reduced pressure, column chromatography and recrystallization, with a yield of 72%. MS (ASAP) = 990.6.

[0231] Example 14

[0232] The synthetic route of Compound 14 in this example is as follows:

[0233]

[0234] Synthesis of Intermediate 14-2: Weigh 10 mmol of Intermediate 4-1, 10 mmol of Intermediate 14-1, 0.1 mmol of Pd2(dba)3, 0.2 mmol of t-Bu3P, and 20 mmol of sodium tert-butoxide into a 500 mL three-necked flask, add 200 mL of toluene, displace nitrogen, and react at 80 °C for 12 h. Rotary evaporate, wash with water, and obtain a white solid by column chromatography (eluent: PE), with a yield of 61%.

[0235] Synthesis of Intermediate 14-3: Place 10 mmol of Intermediate 14-2 in a 500 mL two-necked flask, add 200 mL of DMF until all the solid is dissolved, weigh 10 mmol of NBS and place it in a constant pressure dropping funnel, dissolve it with 100 mL of DMF, slowly drip it, and react at room temperature for 12 h. Rotary evaporate, wash with water, and obtain a white solid by column chromatography (eluent: PE), with a yield of 77%.

[0236] Synthesis of Intermediate 14-5: Prepare a dry 500 mL three-necked flask, set up the reaction apparatus, evacuate it, and then introduce nitrogen; keep the nitrogen flowing in the reaction flask, weigh 10 mmol of Intermediate 14-3, add THF (250 mL), evacuate and introduce nitrogen in a cycle three times, and cool down to -78 °C; slowly add 20 mmol of n-butyllithium solution dropwise to the reaction flask, react at -78 °C for 30 min, and then quickly add 10 mmol of Intermediate 14-4. Let the reaction system slowly warm up to room temperature and react for 12 h. Add water, extract with DCM, spin-dry the solvent, and then obtain a colorless oily substance by column chromatography (the eluent is PE), with a yield of 49%.

[0237] Synthesis of Intermediate 14-6: Prepare a dry 500 mL three-necked flask, set up the reaction apparatus, evacuate it, and then introduce nitrogen; keep the nitrogen flowing in the reaction flask, weigh 10 mmol of Intermediate 3-9, add THF (250 mL), evacuate and introduce nitrogen in a cycle three times, and cool down to -78 °C; slowly add 20 mmol of n-butyllithium solution dropwise to the reaction flask, react at -78 °C for 30 min, and then quickly add 10 mmol of Intermediate 14-5. Let the reaction system slowly warm up to room temperature and react for 12 h. Add water, extract with DCM, spin-dry the solvent, and then obtain a colorless oily substance by column chromatography (the eluent is PE), with a yield of 57%.

[0238] Synthesis of Compound 14: Add magnesium chips (50 mmol), 200 mL of THF, and 5 iodine crystals to a dry and anhydrous two-necked flask. After purging with nitrogen three times, slowly add a THF solution of 10 mmol of Intermediate 14-6 dropwise. After initiation, wait for the system to return to room temperature for 0.5 h, and then drop the system solution into a THF solution of 10 mmol of Intermediate 3-11, and stir at room temperature. During the treatment, add water to quench the Grignard reagent. After the temperature stabilizes, then extract, wash, and separate the layers, collect the organic phase, and obtain Compound 14 through drying, concentration under reduced pressure, column chromatography, and recrystallization, with a yield of 55%. MS (ASAP) = 902.7.

[0239] The preparation process of the OLED device including the above compounds will be described in detail through specific examples below. The structure of the OLED device is: anode substrate / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / cathode. The schematic diagram of the OLED device is as Figure 1 shown, where 10 is the substrate, 20 is the anode, 30 is the hole injection layer, 40 is the hole transport layer, 50 is the light-emitting layer, 60 is the electron transport layer, and 70 is the cathode.

[0240] The preparation steps of OLED-1 are as follows:

[0241] a. Cleaning of the anode substrate: The ITO conductive glass substrate was cleaned using chloroform, ketone, and isopropyl alcohol, and then subjected to ultraviolet ozone plasma treatment;

[0242] b. Preparation of the functional layer: The ITO conductive glass substrate was transferred into a vacuum vapor deposition apparatus. Under high vacuum (1×10-6 mbar), resistance heating evaporation was used. HATCN was evaporated to form a 10-nm hole injection layer, and then HT was evaporated to obtain a 60-nm hole transport layer. The host material (BH) and the blue light guest material (Compound 1) were co-evaporated at a mass ratio of 97:3 to form a 25-nm light-emitting layer. Then, ET and Liq were placed in different evaporation units and co-deposited at a ratio of 50% by weight each to form a 30-nm electron transport layer on the light-emitting layer. Subsequently, 1 nm of LiQ was deposited on the electron transport layer as the electron injection layer, and finally, metal Al was deposited on the electron injection layer to form a cathode with a thickness of 100 nm;

[0243] c. Encapsulation: The device was encapsulated with an ultraviolet-curable resin in a nitrogen glove box.

[0244] The preparation schemes of the devices OLED-2 to OLED-18 in the examples and the devices OLED-Ref1 and OLED-Ref2 in the comparative examples were the same as those of OLED-1, except that the blue light guest material (i.e., the light-emitting material) in the example OLED-1 was replaced with the corresponding Compounds 2-14 and Ref-1 and Ref-2 in Table 1. Among them, Ref-1 and Ref-2 are known blue light guest materials.

[0245] HATCN, HT, BH, ET, Liq, Ref-1, and Ref-2 that may be involved in the OLED preparation process have the following structures and are all commercially available or prepared by known synthetic methods. For details, see the references in the prior art and will not be elaborated here. Among them, HATCN is used as the hole injection layer material, HT is used as the hole transport material, the mixed material of ET and Liq (mixed at a weight ratio of 1:1) is used as the electron transport material, and BH is used as the light-emitting host material of the light-emitting layer.

[0246]

[0247] The current-voltage (J-V) characteristics of each OLED device were characterized by a characterization device, and important parameters such as luminous efficiency, lifetime, and external quantum efficiency were recorded simultaneously. The results are shown in Table 1 below. Among them, the luminous efficiency is the relative value obtained when the current density is 10 mA / cm 2 The luminous efficiency and lifetime are both relative values with respect to the luminous efficiency and lifetime of the device OLED-Ref2.

[0248] Table 1

[0249]

[0250] As shown in Table 1, the devices OLED-1 to OLED-14 in the examples are blue light devices prepared by using Compounds 1-14 as the guest materials in the light-emitting layer. The guest materials of the devices OLED-Ref1 and OLED-Ref2 in the comparative examples are Ref-1 and Ref-2 respectively. Compared with OLED-Ref1 and OLED-Ref2, OLED-1 to OLED-18 have better luminous efficiency and longer lifespan. The organic compound of the present invention has a D-A system, which is connected to dimethylacridine through a silicon-containing group, making the molecular structure of the overall compound have better conjugation and planarity, improving the rigidity and stability of the material molecules. The effect of connecting the silicon group to the para-position benzene ring of the nitrogen of dimethylacridine is better than directly connecting it to the benzene ring on the nitrogen of dimethylacridine. This is because the former silicon group and dimethylacridine are in the same plane, while the latter is not. Therefore, the planarity of the former is better than that of the latter, and the performance is also better than that of the latter (compared with Ref-1); the introduction of diarylsilicon (solubilizing group) further improves the solubility of the molecule and is more conducive to recrystallization, so that the compound is easier to purify, and thus a compound with higher purity can be obtained. When used as a blue light-emitting material in an organic electronic device, a compound with higher purity can improve the luminous efficiency and service life of the device (compared with Ref-2). When used as a blue light-emitting material in an organic electronic device, it can achieve the purpose of extending the luminous efficiency and service life of the device. In addition, the organic compound of the present invention can be used as a blue light guest material, and by cooperating with a suitable host material, it can improve the luminous efficiency and lifespan of the electroluminescent device.

[0251] The above has introduced in detail the organic compounds, mixtures, compositions and organic electronic devices provided by the embodiments of the present invention. Specific examples are used in this article to elaborate on the principles and implementation manners of the present invention. The description of the above embodiments is only used to help understand the method and its core idea of the present invention; at the same time, for those skilled in the art, according to the idea of the present invention, there will be changes in the specific implementation manners and application scopes. In summary, the content of this specification should not be construed as a limitation to the present invention.

Claims

1. An organic compound, characterized in that, It has a structure shown in the general formula (1): Wherein: X1, X2, and X3 are each independently selected from CR6 or N, and at least one of X1, X2, and X3 is selected from N; Each occurrence of Ar1, Ar2, and Ar3 is independently selected from the following groups: Wherein: Each occurrence of X4 is independently selected from CR7 or N; Y1 is independently selected from CR8R9 or O; Each occurrence of R7 is independently selected from: -H, pyridyl, phenyl, tert-butyl, phenanthryl, naphthyl; R8 and R9 are selected from methyl; R1 and R2 are independently selected from: -H, methyl, tert-butyl; R3 and R4 are independently selected from: methyl, ethyl, tert-butyl, phenyl; R5 is selected from -H; R6 is selected from -H; m is selected from 1, 2, 3, or 4; * represents the connection site.

2. The organic compound according to claim 1, characterized in that, Each occurrence of Ar1, Ar2, and Ar3 is independently selected from the following groups: * represents the connection site.

3. An organic compound, characterized in that, The organic compound is selected from any one of the following structures:

4. A mixture, characterized in that, The mixture includes the organic compound according to any one of claims 1-3 and at least one organic functional material, and the organic functional material is selected from hole injection material, hole transport material, electron transport material, electron injection material, electron blocking material, hole blocking material, light-emitting guest material, light-emitting host material, or organic dye.

5. A composition, characterized in that, The composition includes the organic compound according to any one of claims 1-3 or the mixture according to claim 4, and at least one organic solvent.

6. An organic electronic device includes at least one functional layer, characterized in that, The functional layer contains the organic compound according to any one of claims 1-3, or the mixture according to claim 4, or the functional layer is prepared from the composition according to claim 5.

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