Organic compound, mixture, composition, organic light-emitting device and display panel

Abstract

The invention discloses an organic compound, a mixture, a composition, an organic light-emitting device and a display panel. The organic compound has a structure as shown in a general formula (1) or a general formula (2). According to the invention, a group which enables the overall conjugacy of the compound to be higher is introduced into the boron-nitrogen compound, so that the material performance is improved, the luminous efficiency of the organic light-emitting device is improved, and the service life of the organic light-emitting device is prolonged.

Description

Technical Field

[0001] This application relates to the field of display, specifically to an organic compound, mixture, composition, organic light-emitting device, and display panel. Background Technology

[0002] Currently, organic light-emitting diodes (OLEDs) typically consist of an anode, a cathode, and an organic layer between them. The organic material in the organic layer converts electrical energy into light energy, thus achieving organic electroluminescence. To improve the luminous efficiency and lifespan of OLEDs, the organic layer is often multi-layered, with each layer containing different organic materials. Specifically, the organic layer mainly includes a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied between the anode and cathode of the OLED, holes are injected into the organic layer by the anode, and electrons are injected into the organic layer by the cathode. The injected holes and electrons meet to form excitons, which emit light when they transition back to the ground state, thus realizing the light emission of the OLED. OLEDs possess characteristics such as self-luminescence, high brightness, high efficiency, low voltage driving, wide viewing angle, high contrast, and high response, therefore, OLEDs have broad application prospects.

[0003] To improve the luminous efficiency of organic electroluminescent devices (OLEDs), various luminescent material systems based on fluorescence and phosphorescence have been developed. Among these, OLEDs using fluorescent materials exhibit high reliability; however, under electrical excitation, the internal electroluminescence quantum efficiency is limited to below 25% due to the 1:3 branching ratio of singlet to triplet excited states of the exciton. In contrast, OLEDs using phosphorescent materials can achieve almost 100% internal electroluminescence quantum efficiency. However, phosphorescent materials typically use iridium- and platinum-containing metal complexes, which are expensive and complex to synthesize. Furthermore, phosphorescent OLEDs suffer from a roll-off effect, where the luminous efficiency decreases rapidly with increasing current or brightness, limiting their application at high brightness levels.

[0004] To overcome the aforementioned problems, current luminescent materials are typically based on various combinations of organic compounds, such as composite excited-state materials and thermally activated delayed fluorescence (TADF) materials, attempting to achieve high efficiency comparable to phosphorescent organic electroluminescent devices by utilizing reverse internal conversion. However, the performance improvement of traditional TADF-containing organic compounds is limited in terms of both efficiency and lifetime, making it difficult to improve the luminous efficiency and lifetime of organic electroluminescent devices using TADF-containing organic compounds.

[0005] Therefore, there is an urgent need for an organic compound for organic light-emitting devices to solve the above-mentioned technical problems. Summary of the Invention

[0006] The embodiments of this application provide an organic compound, mixture, composition, organic light-emitting device, and display panel, which can improve the luminous efficiency and lifespan of the organic light-emitting device.

[0007] Embodiments of this application provide an organic compound having a structure as shown in general formula (1) or general formula (2):

[0008]

[0009] Ar1 has the structure represented by equation (X-1) or equation (X-2):

[0010]

[0011] Ar2 and Ar3 have the structures represented by any of equations (A-1) to (A-5):

[0012]

[0013] Ar2 has fusion sites on two adjacent carbon atoms in the same benzene ring, while Ar3 has linkage sites on carbon atoms in any benzene ring.

[0014] n0 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14;

[0015] n1 is selected from 0, 1, 2, or 3;

[0016] n2 is selected from 0, 1, 2, 3, 4 or 5;

[0017] n3 is selected from 0 or 1;

[0018] R0, R1, R2, and R3 are selected from -H, -D, straight-chain alkyl groups with 1 to 20 carbon atoms, straight-chain alkoxy groups with 1 to 20 carbon atoms, straight-chain thioalkoxy groups with 1 to 20 carbon atoms, branched alkyl groups with 3 to 20 carbon atoms, cyclic alkyl groups with 3 to 20 carbon atoms, branched alkoxy groups with 3 to 20 carbon atoms, cyclic alkoxy groups with 3 to 20 carbon atoms, branched thioalkoxy groups with 3 to 20 carbon atoms, cyclic thioalkoxy groups with 3 to 20 carbon atoms, silyl groups, ketone groups with 1 to 20 carbon atoms, and groups with a carbon number of 1 to 20. Alkoxycarbonyl groups with 2 to 20 carbon atoms, aryloxycarbonyl groups with 7 to 20 carbon atoms, alkenyl groups with 1 to 20 carbon atoms, -CN, carbamoyl, halocarbamoyl, formyl, isocyanate, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, -CF3, -Cl, -Br, -F, substituted or unsubstituted aromatic groups with 6 to 30 ring atoms, substituted or unsubstituted heteroaromatic groups with 5 to 30 ring atoms, substituted or unsubstituted aryloxy groups with 6 to 30 ring atoms, and substituted or unsubstituted heteroaromatic groups with 5 to 30 ring atoms;

[0019] When n0 is greater than or equal to 2, two adjacent R0s may or may not form a cycle; when n1 is greater than or equal to 2, two adjacent R1s may or may not form a cycle; when n2 is greater than or equal to 2, two adjacent R2s may or may not form a cycle.

[0020] In one embodiment of this application, the organic compound has a structure as shown in any of general formulas (2-1) to (2-23):

[0021]

[0022]

[0023]

[0024]

[0025] n 01 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9;

[0026] In the structure shown in general formula (2), Ar1 and diarylamine are located on the same side of the organic compound.

[0027] In one embodiment of this application, R0, R1, R2 and R3 are selected from -H, -D, straight-chain alkyl with 1 to 10 carbon atoms, branched alkyl with 3 to 10 carbon atoms, and cyclic alkyl with 3 to 10 carbon atoms.

[0028] In one embodiment of this application, R0, R1, R2 and R3 are selected from straight-chain alkyl groups with -H, -D, 1 to 4 carbon atoms, and branched alkyl groups with 3 to 5 carbon atoms.

[0029] In one embodiment of this application, the organic compound is selected from compounds represented by Formulas 1 to 244:

[0030]

[0031]

[0032]

[0033]

[0034]

[0035]

[0036]

[0037]

[0038]

[0039] In accordance with the above-mentioned objectives of this application, embodiments of this application also provide a mixture comprising the organic compound and at least one organic functional material, wherein the organic functional material is selected from hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, luminescent materials, host materials, or organic dyes.

[0040] In accordance with the above-mentioned objectives of this application, embodiments of this application also provide a composition comprising the organic compound and at least one organic solvent, or the composition comprising the mixture and at least one of the organic solvents.

[0041] In accordance with the above-mentioned objectives of this application, embodiments of this application also provide an organic light-emitting device, the organic light-emitting device comprising:

[0042] First electrode;

[0043] The second electrode is disposed opposite to the first electrode; and

[0044] An organic functional layer is located between the first electrode and the second electrode;

[0045] The material of the organic functional layer includes one or more of the organic compounds, or the material of the organic functional layer includes the mixture, or the material of the organic functional layer includes the composition.

[0046] In one embodiment of this application, the organic functional layer includes at least a light-emitting layer, the light-emitting layer includes a host material and a guest material, the guest material includes one or more of the organic compounds, and the host material includes fused aromatic derivatives or heteroaromatic compounds.

[0047] In accordance with the above objectives of this application, embodiments of this application also provide a display panel, the display panel including the organic light-emitting device.

[0048] This application improves material properties, increases the luminous efficiency of organic light-emitting devices, and extends the lifespan of organic light-emitting devices by introducing groups that increase the overall conjugation of the boron nitrogen compound. Furthermore, in the structure shown in general formula (2), the diarylamine and Ar1 are located on the same side of the organic compound, and in the structure shown in general formula (1), the diarylamine and Ar2 are located on the same side of the organic compound. Ar1 is selected from tert-butylphenylthiophene or tert-butylbenzene, and Ar2 is selected from biphenyl-type groups. As a result, the steric hindrance of Ar2 is less than that of Ar1. Therefore, the steric hindrance on the side with Ar1 in the structure shown in general formula (2) is greater than that on the side with Ar2 in the structure shown in general formula (1), which can effectively improve the device performance of organic light-emitting devices with organic compounds shown in general formula (2). Attached Figure Description

[0049] Figure 1 The proton NMR spectrum of organic compound M220 provided for embodiments of this application;

[0050] Figure 2 A schematic diagram of a structure of an organic light-emitting device provided for an embodiment of this application;

[0051] Figure 3 This is a schematic diagram of another structure of an organic light-emitting device provided for an embodiment of this application. Detailed Implementation

[0052] The technical solutions in the embodiments of this application will be described below with reference to the accompanying drawings. Furthermore, it should be understood that the specific embodiments described herein are for illustrative and explanatory purposes only and are not intended to limit this application. In this application, unless otherwise stated, directional terms such as "upper" and "lower" generally refer to the upper and lower positions of the device in its actual use or working state, specifically the drawing directions in the accompanying drawings; while "inner" and "outer" refer to the outline of the device. In this application, "optionally," "optionally," and "optional" mean that they are optional, that is, selected from either "with" or "without" parallel solutions. If multiple "optional" statements appear in a technical solution, unless otherwise specified and without contradiction or mutual constraint, each "optional" statement is independent. In this application, the technical features described in an open-ended manner include both closed-ended technical solutions composed of the listed features and open-ended technical solutions containing the listed features.

[0053] In this application, aromatic groups, aromatic families, and aromatic ring systems have the same meaning and can be used interchangeably.

[0054] In this application, heteroaromatic groups, heteroaromatic families, and heteroaromatic ring systems have the same meaning and can be used interchangeably.

[0055] In this application, "substitution" means that the hydrogen atom in the substituent is replaced by the substituent.

[0056] In this application, when the same substituent appears multiple times, it can be independently selected from different groups. If the general formula contains multiple R, then R can be independently selected from different groups.

[0057] In this application, "substituted or unsubstituted" means that the defined group may or may not be substituted. When the defined group is substituted, it should be understood that the defined group can be substituted by one or more substituents R, wherein R is selected from, but is not limited to: deuterium, cyano, isocyano, nitro or halogen, alkyl containing 1-20 carbon 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, carbonyl, alkoxycarbonyl, aryloxycarbonyl, carbamoyl, halocarbamoyl, formyl, isocyanate group, thiocyanate group, isothiocyanate group, hydroxyl, trifluoromethyl, and the above groups may also be further substituted by substituents acceptable in the art; it is understood that R' and R" in -NR'R" are each independently selected from, but not limited to: H, deuterium atom The group R is selected from, but is not limited to, deuterium, cyano, isocyano, nitro or halogen, alkyl containing 1-10 carbon atoms, heterocyclic group containing 3-20 ring atoms, aromatic group containing 6-20 ring atoms, and heteroaromatic group containing 5-20 ring atoms. Preferably, R is selected from, but is not limited to, deuterium, cyano, isocyano, nitro or halogen, alkyl containing 1-10 carbon atoms, heterocyclic group containing 3-10 ring atoms, aromatic group containing 6-20 ring atoms, heteroaromatic group containing 5-20 ring atoms, silyl, carbonyl, alkoxycarbonyl, aryloxycarbonyl, carbamoyl, haloformyl, formyl, isocyanate group, thiocyanate group, isothiocyanate group, hydroxyl, trifluoromethyl, and the above groups may be further substituted with substituents acceptable in the art.

[0058] In this application, "ring atom number" refers to the number of atoms in the ring itself of a structural compound obtained by atomic bonding to form a ring (e.g., monocyclic compound, fused ring compound, cross-linked 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 "ring atom number" described below unless otherwise specified. For example, the benzene ring has 6 ring atoms, the naphthalene ring has 10 ring atoms, and the thiophene group has 5 ring atoms.

[0059] In this application, "aryl or aromatic group" refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removing one hydrogen atom. It can be a monocyclic aryl, a fused-ring aryl, or a polycyclic aryl, and for polycyclic rings, at least one of them is an aromatic ring system. For example, "substituted or unsubstituted aryl having 6 to 40 ring atoms" means an aryl containing 6 to 40 ring atoms, preferably a substituted or unsubstituted aryl having 6 to 30 ring atoms, more preferably a substituted or unsubstituted aryl having 6 to 18 ring atoms, and particularly preferably a substituted or unsubstituted aryl having 6 to 14 ring atoms, and optionally further substituted on the aryl group; suitable examples include, but are not limited to: phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, fluoranyl, triphenylene, pyrene, perylene, tetraphenyl, fluorenyl, dinaphthylphenyl, acenaphthyl and their derivatives. It is understandable 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 acenaphthene, fluorene, or 9,9-diarylfluorene, triarylamine, and diaryl ether systems should also be included in the definition of aryl.

[0060] In this application, "heteroaryl or heteroaromatic group" refers to an aryl group in which at least one carbon atom is replaced by a non-carbon atom, which 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, and particularly preferably a substituted or unsubstituted heteroaryl group having 6 to 14 ring atoms. The heteroaryl group may optionally be further substituted, and suitable examples include, but are not limited to, thiophene, furanyl, pyrrole, imidazolyl, diazolyl, triazolyl, imidazolyl, pyridyl, bipyridyl, and pyrimidine. Triazinyl, acridineyl, pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridinylpyrimidinyl, pyridinylpyrazinyl, benzothiopheneyl, benzofuranyl, indolyl, pyrroloimidazolyl, pyrrolopyrrolyl, thienopyrrolyl, thienopyrrolyl, furanolyl, furanolyl, thienofuranyl, benzoisoxazolyl, benzoisothiazolyl, benzoimidazolyl, o-diazonyl, phenanthridineyl, primidyl, quinazolinoneyl, dibenzothiopheneyl, dibenzofuranyl, carbazoleyl and their derivatives.

[0061] In this application, "alkyl" can mean straight-chain, branched, and / or cyclic alkyl. The number of carbon atoms in an alkyl group can be 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Phrases containing this term, such as "C 1-9"Alkyl" refers to an alkyl group containing 1 to 9 carbon atoms, and each time it appears, it can independently be a C1 alkyl, C2 alkyl, C3 alkyl, C4 alkyl, C5 alkyl, C6 alkyl, C7 alkyl, C8 alkyl, or C9 alkyl. Non-limiting examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, etc. tert-amyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl The compounds include 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-pentadecanyl, n-hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, n-hepta ...

[0062] In this application, the abbreviations for substituents are: n-n-, sec-sec-, i-iso-, t-tert-, o-ortho-, m-me-, p-para-, Me-methyl, Et-ethyl, Pr-propyl, Bu-butyl, Am-pentyl, Hx-hexyl, Cy-cyclohexyl.

[0063] In this application, "amino group" refers to an amine derivative having the structural feature of the formula -N(X)2, wherein each "X" is independently H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a 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)2, -NH(heterocyclic), -N(aryl)2, -NH(aryl), -N(alkyl)(aryl), -N(alkyl)(heterocyclic), -N(cycloalkyl)(heterocyclic), -N(aryl)(heteroaryl), -N(alkyl)(heteroaryl), etc.

[0064] In this application, unless otherwise defined, hydroxyl refers to -OH, carboxyl refers to -COOH, carbonyl refers to -C(=O)-, amino refers to -NH2, formyl refers to -C(=O)H, haloformyl refers to -C(=O)Z (where Z represents halogen), carbamoyl refers to -C(=O)NH2, isocyanate refers to -NCO, and isothiocyanate refers to -NCS.

[0065] In this application, the term "alkoxy" refers to a group with the structure "-O-alkyl", that is, an alkyl group as defined above that is attached 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 (-OC(CH3)3 or -OtBu).

[0066] In this application, the "*" connected to a single bond indicates a connection or fusion site.

[0067] In this application, when no linking site is specified in the group, it means that any linkable site in the group is selected as the linking site.

[0068] In this application, when no fusion site is specified in the group, it means that any fusionable site in the group is selected as the fusion site, preferably two or more sites in the adjacent position of the group are fusion sites.

[0069] In this application, when the same group contains multiple substituents with the same symbol, the substituents can be the same as or different from each other, for example... The six R's on the benzene ring can be the same or different from each other.

[0070] In this application, the single bonds connecting the substituents extend through the corresponding ring, indicating that the substituent can be attached to any position on the ring, for example... R is attached to any substituted site on the benzene ring; such as express Can be with A fused ring can be formed at any position on the benzene ring.

[0071] The terms cycloalkyl or cycloalkyl as used in this application have the same meaning and are interchangeable.

[0072] In this application, "adjacent groups" means that there are no substituted sites between two substituents.

[0073] In this application, "two adjacent R0, R1, or R2 forming a ring" means a ring system formed by connecting two adjacent R0, R1, or R2. The ring system can be selected from aliphatic hydrocarbon rings, aliphatic heterocycles, aromatic hydrocarbon rings, or aromatic heterocycles. Preferably, it can form...

[0074] Embodiments of this application provide an organic compound having a structure as shown in general formula (1) or general formula (2):

[0075]

[0076] Ar1 has the structure represented by equation (X-1) or equation (X-2):

[0077]

[0078] Ar2 and Ar3 have the structures represented by any of equations (A-1) to (A-5):

[0079]

[0080] Ar2 has fusion sites on two adjacent carbon atoms in the same benzene ring, while Ar3 has linkage sites on carbon atoms in any benzene ring.

[0081] n0 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14;

[0082] n1 is selected from 0, 1, 2, or 3;

[0083] n2 is selected from 0, 1, 2, 3, 4 or 5;

[0084] n3 is selected from 0 or 1;

[0085] R0, R1, R2, and R3 are selected from -H, -D, straight-chain alkyl groups with 1 to 20 carbon atoms, straight-chain alkoxy groups with 1 to 20 carbon atoms, straight-chain thioalkoxy groups with 1 to 20 carbon atoms, branched alkyl groups with 3 to 20 carbon atoms, cyclic alkyl groups with 3 to 20 carbon atoms, branched alkoxy groups with 3 to 20 carbon atoms, cyclic alkoxy groups with 3 to 20 carbon atoms, branched thioalkoxy groups with 3 to 20 carbon atoms, cyclic thioalkoxy groups with 3 to 20 carbon atoms, silyl groups, ketone groups with 1 to 20 carbon atoms, and groups with a carbon number of 1 to 20. Alkoxycarbonyl groups with 2 to 20 carbon atoms, aryloxycarbonyl groups with 7 to 20 carbon atoms, alkenyl groups with 1 to 20 carbon atoms, -CN, carbamoyl, halocarbamoyl, formyl, isocyanate, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, -CF3, -Cl, -Br, -F, substituted or unsubstituted aromatic groups with 6 to 30 ring atoms, substituted or unsubstituted heteroaromatic groups with 5 to 30 ring atoms, substituted or unsubstituted aryloxy groups with 6 to 30 ring atoms, and substituted or unsubstituted heteroaromatic groups with 5 to 30 ring atoms;

[0086] When n0 is greater than or equal to 2, two adjacent R0s may or may not form a cycle; when n1 is greater than or equal to 2, two adjacent R1s may or may not form a cycle; when n2 is greater than or equal to 2, two adjacent R2s may or may not form a cycle.

[0087] In the structure shown in general formula (2), Ar1 and diarylamine are located on the same side of the organic compound.

[0088] The embodiments of this application improve material properties, increase the luminous efficiency of organic light-emitting devices, and extend the lifespan of organic light-emitting devices by introducing groups that make the overall conjugation of the compound into the boron nitrogen compound. Furthermore, in the structure shown in general formula (2), the diarylamine and Ar1 are located on the same side of the organic compound, and in the structure shown in general formula (1), the diarylamine and Ar2 are located on the same side of the organic compound. Ar1 is selected from tert-butylphenylpropiophene or tert-butylbenzene, and Ar2 is selected from biphenyl-type groups. As a result, the steric hindrance of Ar2 is less than that of Ar1. Therefore, the steric hindrance on the side with Ar1 in the structure shown in general formula (2) is greater than that on the side with Ar2 in the structure shown in general formula (1), which can effectively improve the device performance of organic light-emitting devices with organic compounds shown in general formula (2).

[0089] In some embodiments, the organic compound has a structure as shown in any of general formulas (2-1) to (2-23):

[0090]

[0091]

[0092]

[0093]

[0094] n 01 Choose from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9.

[0095] In some embodiments, R0, R1, R2, and R3 are selected from -H, -D, straight-chain alkyl groups having 1 to 10 carbon atoms, branched alkyl groups having 3 to 10 carbon atoms, and cyclic alkyl groups having 3 to 10 carbon atoms.

[0096] In some embodiments, R0, R1, R2, and R3 are selected from -H, -D, straight-chain alkyl groups having 1 to 4 carbon atoms, and branched alkyl groups having 3 to 5 carbon atoms.

[0097] It should be noted that R0 can be the same group or a different group each time it appears. Similarly, R1 can be the same group or a different group each time it appears, R2 can be the same group or a different group each time it appears, and R3 can be the same group or a different group each time it appears. Furthermore, R0, R1, R2, and R3 can be the same group or a different group each time they appear.

[0098] The embodiments of this application, by introducing alkyl groups into the organic compound, can improve the solubility of the organic compound in processes such as inkjet printing, thereby enhancing the product quality of organic light-emitting devices using the organic compound.

[0099] In some embodiments, two adjacent R0s form a ring with each other; further, two adjacent R0s form a ring with each other to form a 6-membered aromatic ring or an aliphatic ring; even further, two adjacent R0s form a ring with each other to form In this context, * indicates a connection site.

[0100] In some embodiments, two adjacent R1s form a ring with each other; further, two adjacent R1s form a ring with each other to form a 6-membered aromatic ring or an aliphatic ring; even further, two adjacent R1s form a ring with each other to form In this context, * indicates a connection site.

[0101] In some embodiments, two adjacent R2s form a ring with each other; further, two adjacent R2s form a ring with each other to form a 6-membered aromatic ring or an aliphatic ring; even further, two adjacent R2s form a ring with each other to form In this context, * indicates a connection site.

[0102] In some embodiments, two adjacent R3s form a ring with each other; further, two adjacent R3s form a ring with each other to form a 6-membered aromatic ring or an aliphatic ring; even further, two adjacent R3s form a ring with each other to form In this context, * indicates a connection site.

[0103] In some embodiments, the organic compound may be a blue luminescent material.

[0104] In some embodiments, the organic compound is selected from compounds represented by Formulas 1 to 244:

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115] The boron-containing biphenyl organic compounds provided in the embodiments of this application introduce structures such as dibenzofuran, dibenzothiophene, carbazole, benzo5-membered ring, triphenylene and / or naphthalene into the boron-nitrogen compound, resulting in greater overall molecular conjugation and improving the luminous efficiency and lifespan of organic light-emitting devices using the organic compound. At the same time, the introduction of tetrahydronaphthalene and / or indene structures into the boron-nitrogen compound improves the solubility of the molecule in processes such as inkjet printing, making the compound easier to purify, thereby improving the purity of the organic compound and further extending the luminous efficiency and lifespan of organic light-emitting devices using the organic compound.

[0116] Furthermore, embodiments of this application also provide a method for preparing the organic compounds described in the above embodiments, and provide Examples 1 to 17 to detail the method for preparing the organic compounds.

[0117] Example 1

[0118] The synthetic route for organic compound M1 is as follows:

[0119]

[0120] Synthesis of intermediates 1-3:

[0121] Compound 1-1 (10 mmol), compound 1-2 (10 mmol), Pd(dba)2 (bis(dibenzylacetone)palladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted, washed with water, and separated. Organic phase column chromatography was performed to give intermediate 1-3 with a molar amount of 8.21 mmol and a yield of 82.1%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 1-3 was: MS(ASAP) = 337.

[0122] Synthesis of intermediates 1-5:

[0123] Compounds 1-3 (10 mmol), 1-4 (10 mmol), Pd(dba)2 (bis(dibenzylacetone)palladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted, washed with water, and separated. Organic phase column chromatography was performed to give intermediate 1-5 with a molar amount of 7.28 mmol and a yield of 72.8%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 1-5 was: MS(ASAP) = 481.

[0124] Synthesis of intermediates 1-7:

[0125] Intermediate 1-5 (10 mmol), compound 1-6 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-biscyclohexylphosphine-2',6'-dimethoxy-1,1'-diphenyl, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted, washed with water, and separated. Organic phase column chromatography was performed to give intermediate 1-7 with a molar amount of 5.45 mmol and a yield of 58.6%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate 1-7 was: MS(ASAP) = 594.

[0126] Synthesis of intermediates 1-9:

[0127] Intermediate 1-7 (10 mmol), compound 1-8 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-bicyclohexylphosphine-2',6'-dimethoxy-1,1'-diphenyl, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted, washed with water, and separated. Organic phase column chromatography was performed to obtain intermediate 1-9 with a molar amount of 6.11 mmol and a yield of 61.1%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate 1-9 was: MS(ASAP) = 760.

[0128] Synthesis of intermediates 1-11:

[0129] Intermediate 1-9 (10 mmol), intermediate 1-10 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-diphenyl, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted, washed with water, and separated. Organic phase column chromatography was performed to obtain intermediate 1-11 with a molar amount of 8.04 mmol, yield: 80.4%. Atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate 1-11: MS(ASAP) = 1005.

[0130] Synthesis of organic compound M1:

[0131] In a 250 mL three-necked flask, 10 mmol of intermediate 1-11 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a hexane solution of t-BuLi (tert-butyllithium) (21 mmol) was added dropwise. The temperature was raised to 60 °C and the reaction was carried out for 2 hours. The hexane solvent was then removed by vacuum distillation. The reaction solution was cooled again to -30 °C, and boron tribromide (21 mmol) was added. The mixture was stirred at room temperature for 0.5 hours, and then cooled to 0 °C. 42 mmol of boron tribromide was added... N,N-Diisopropylethylamine was added dropwise, and the mixture was heated to room temperature and stirred. The temperature was then increased to 120°C and stirred for 3 hours. The reaction solution was cooled to room temperature. Sodium carbonate aqueous solution was added and ethyl acetate was added to quench the reaction. The aqueous phase was extracted with ethyl acetate and the organic phases were combined. The solvent was removed by rotary evaporation to obtain the crude product. The crude product was purified by rapid silica gel column chromatography to obtain the pure product. The product was recrystallized from toluene and ethyl acetate to obtain a pale yellow solid powder, namely organic compound M1, with a yield of 47.3%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound M1 was: MS(ASAP) = 979.

[0132] Example 2

[0133] The synthetic route for organic compound M2 is as follows:

[0134]

[0135] Synthesis of intermediate 2-2:

[0136] Intermediate 1-5 (10 mmol), compound 2-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-biscyclohexylphosphine-2',6'-dimethoxy-1,1'-diphenyl, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted, washed with water, and separated. Organic phase column chromatography was performed to give intermediate 2-2 with a molar amount of 6.47 mmol and a yield of 64.7%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate 2-2 was: MS(ASAP) = 580.

[0137] Synthesis of intermediates 2-3:

[0138] Intermediate 2-2 (10 mmol), compound 1-8 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-bicyclohexylphosphine-2',6'-dimethoxy-1,1'-diphenyl, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted, washed with water, and separated. Organic phase column chromatography was performed to give intermediate 2-3 with a molar amount of 8.36 mmol and a yield of 83.6%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate 2-3 was: MS(ASAP) = 746.

[0139] Synthesis of intermediates 2-4:

[0140] Intermediate 2-3 (10 mmol) and intermediate 1-10 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (2 1 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The mixture was stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, followed by extraction and washing with water. The mixture was then separated by organic phase column chromatography and recrystallization to obtain intermediate 2-4 with a molar amount of 7.58 mmol and a yield of 75.8%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate 2-4 was MS(ASAP) = 991.

[0141] Synthesis of organic compound M2:

[0142] In a 250 mL three-necked flask, 10 mmol of intermediate 2-4 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a hexane solution of t-BuLi (tert-butyllithium) (21 mmol) was added dropwise. The temperature was raised to 60 °C and the reaction was carried out for 2 hours. The hexane solvent was then removed by vacuum distillation. The reaction solution was cooled again to -30 °C, and boron tribromide (21 mmol) was added. The mixture was stirred at room temperature for 0.5 hours, and then cooled to 0 °C. 42 mmol of boron tribromide was added... N,N-Diisopropylethylamine was added dropwise, and the mixture was heated to room temperature and stirred. The temperature was then increased to 120°C and stirred for 3 hours. The reaction solution was cooled to room temperature. Sodium carbonate aqueous solution was added and ethyl acetate was added to quench the reaction. The aqueous phase was extracted with ethyl acetate and the organic phases were combined. The solvent was removed by rotary evaporation to obtain the crude product. The crude product was purified by rapid silica gel column chromatography to obtain the pure product. The product was recrystallized from toluene and ethyl acetate to obtain a pale yellow solid powder, namely organic compound M2, with a yield of 46.8%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound M2 was: MS(ASAP) = 965.

[0143] Example 3

[0144] The synthetic route for organic compound M3 is as follows:

[0145]

[0146] Synthesis of intermediate 3-2:

[0147] Intermediate 1-5 (10 mmol), compound 3-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-biscyclohexylphosphine-2',6'-dimethoxy-1,1'-diphenyl, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted, washed with water, and separated. Organic phase column chromatography was performed to give intermediate 3-2 with a molar amount of 7.83 mmol and a yield of 78.3%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 3-2 was: MS(ASAP) = 566.

[0148] Synthesis of intermediate 3-3:

[0149] Intermediate 3-2 (10 mmol), compound 1-8 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-bicyclohexylphosphine-2',6'-dimethoxy-1,1'-diphenyl, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted, washed with water, and separated. Organic phase column chromatography was performed to obtain intermediate 3-3 with a molar amount of 8.51 mmol and a yield of 85.1%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 3-3 was: MS(ASAP) = 732.

[0150] Synthesis of intermediates 3-4:

[0151] Intermediate 3-3 (10 mmol) and intermediate 1-10 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (2 1 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The mixture was stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, followed by extraction, washing with water, and separation. Organic phase column chromatography and recrystallization were performed to obtain intermediate 3-4 with a molar amount of 5.97 mmol, yield: 59.7%. Atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate 3-4: MS(ASAP) = 977.

[0152] Synthesis of organic compound M3:

[0153] In a 250 mL three-necked flask, 10 mmol of intermediate 2-4 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a hexane solution of t-BuLi (tert-butyllithium) (21 mmol) was added dropwise. The temperature was raised to 60 °C and the reaction was carried out for 2 hours. The hexane solvent was then removed by vacuum distillation. The reaction solution was cooled again to -30 °C, and boron tribromide (21 mmol) was added. The mixture was stirred at room temperature for 0.5 hours, and then cooled to 0 °C. 42 mmol of boron tribromide was added... N,N-Diisopropylethylamine was added dropwise, and the mixture was heated to room temperature and stirred. The temperature was then increased to 120°C and stirred for 3 hours. The reaction solution was cooled to room temperature. Sodium carbonate aqueous solution was added and ethyl acetate was added to quench the reaction. The aqueous phase was extracted with ethyl acetate and the organic phases were combined. The solvent was removed by rotary evaporation to obtain the crude product. The crude product was purified by rapid silica gel column chromatography to obtain the pure product. The product was recrystallized from toluene and ethyl acetate to obtain a pale yellow solid powder, namely organic compound M3, with a yield of 40.6%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound M3 was: MS(ASAP) = 951.

[0154] Example 4

[0155] The synthetic route for organic compound M16 is as follows:

[0156]

[0157] Synthesis of intermediate 16-2:

[0158] Intermediate 16-1 (10 mmol) and intermediate 1-10 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (2 1 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The mixture was stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, followed by extraction and washing with water. The mixture was then separated by organic phase column chromatography and recrystallization to obtain intermediate 16-2 with a molar amount of 9.15 mmol, yield: 91.5%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 16-2 was: MS(ASAP) = 428.

[0159] Synthesis of intermediate 16-4:

[0160] Compound 16-2 (10 mmol), compound 16-3 (10 mmol), Pd(dba)2 (bis(dibenzylacetone)palladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted, washed with water, and separated. Organic phase column chromatography was performed to give intermediate 16-4 with a molar amount of 7.28 mmol and a yield of 72.8%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 16-4 was: MS(ASAP) = 560.

[0161] Synthesis of intermediate 16-5:

[0162] Compound 16-4 (10 mmol), compound 1-4 (10 mmol), Pd(dba)2 (bis(dibenzylacetone)palladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted, washed with water, and separated. Organic phase column chromatography was performed to give intermediate 16-5 with a molar amount of 6.76 mmol and a yield of 67.6%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 16-5 was: MS(ASAP) = 704.

[0163] Synthesis of intermediate 16-8:

[0164] Intermediate 16-6 (10 mmol), compound 16-7 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-diphenyl, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted, washed with water, and separated. Organic phase column chromatography was performed to obtain intermediate 16-8 with a molar amount of 5.42 mmol and a yield of 54.2%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 16-8 was: MS(ASAP) = 281.

[0165] Synthesis of intermediate 16-9:

[0166] Intermediate 16-8 (10 mmol), compound 1-2 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-bicyclohexylphosphine-2',6'-dimethoxy-1,1'-diphenyl, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted, washed with water, and separated. Organic phase column chromatography was performed to give intermediate 16-9 with a molar amount of 5.97 mmol and a yield of 59.7%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 16-9 was: MS(ASAP) = 469.

[0167] Synthesis of intermediate 16-10:

[0168] Intermediate 16-9 (10 mmol), intermediate 16-5 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-diphenyl, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 120 °C for 3 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, followed by extraction, washing with water, and separation. Organic phase column chromatography and recrystallization yielded intermediate 16-10 with a molar amount of 7.71 mmol, yield: 77.1%. Atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate 16-10: MS(ASAP) = 1137.

[0169] Synthesis of organic compound M16:

[0170] In a 250 mL three-necked flask, 10 mmol of intermediate 16-10 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a hexane solution of t-BuLi (tert-butyllithium) (21 mmol) was added dropwise. The temperature was raised to 60 °C and the reaction was carried out for 2 hours. The hexane solvent was then removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and boron tribromide (21 mmol) was added. The mixture was stirred at room temperature for 0.5 hours, and then cooled to 0 °C. 42 mmol of boron tribromide was added... N,N-Diisopropylethylamine was added dropwise, and the mixture was heated to room temperature and stirred. The temperature was then increased to 120°C and stirred for 3 hours. The reaction solution was cooled to room temperature. Sodium carbonate aqueous solution was added and ethyl acetate was added to quench the reaction. The aqueous phase was extracted with ethyl acetate and the organic phases were combined. The solvent was removed by rotary evaporation to obtain the crude product. The crude product was purified by rapid silica gel column chromatography to obtain the pure product. The product was recrystallized from toluene and ethyl acetate to obtain a pale yellow solid powder, namely organic compound M16, with a yield of 36.4%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound M16 was: MS(ASAP) = 1111.

[0171] Example 5

[0172] The synthetic route for organic compound M20 is as follows:

[0173]

[0174] Synthesis of intermediate 20-2:

[0175] Intermediate 16-6 (10 mmol), compound 20-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-biscyclohexylphosphine-2',6'-dimethoxy-1,1'-diphenyl, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted, washed with water, and separated. Organic phase column chromatography was performed to give intermediate 20-2 with a molar amount of 6.94 mmol and a yield of 69.4%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 20-2 was: MS(ASAP) = 281.

[0176] Synthesis of intermediate 20-3:

[0177] Intermediate 20-2 (10 mmol), compound 1-2 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-bicyclohexylphosphine-2',6'-dimethoxy-1,1'-diphenyl, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted, washed with water, and separated. Organic phase column chromatography was performed to obtain intermediate 20-3 with a molar amount of 6.33 mmol and a yield of 63.3%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 20-3 was: MS(ASAP) = 469.

[0178] Synthesis of intermediate 20-4:

[0179] Intermediate 20-3 (10 mmol), intermediate 16-5 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-diphenyl, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 120 °C for 3 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, followed by extraction, washing with water, and separation. Organic phase column chromatography and recrystallization yielded intermediate 20-4 with a molar amount of 5.71 mmol, yield: 57.1%. Atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate 20-4: MS(ASAP) = 1137.

[0180] Synthesis of organic compound M20:

[0181] In a 250 mL three-necked flask, 10 mmol of intermediate 20-4 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a hexane solution of t-BuLi (tert-butyllithium) (21 mmol) was added dropwise. The temperature was raised to 60 °C and the reaction was carried out for 2 hours. The hexane solvent was then removed by vacuum distillation. The reaction solution was cooled again to -30 °C, and boron tribromide (21 mmol) was added. The mixture was stirred at room temperature for 0.5 hours, and then cooled to 0 °C. 42 mmol of boron tribromide was added... N,N-Diisopropylethylamine was added dropwise, and the mixture was heated to room temperature and stirred. The temperature was then increased to 120°C and stirred for 3 hours. The reaction solution was cooled to room temperature. Sodium carbonate aqueous solution was added and ethyl acetate was added to quench the reaction. The aqueous phase was extracted with ethyl acetate and the organic phases were combined. The solvent was removed by rotary evaporation to obtain the crude product. The crude product was purified by rapid silica gel column chromatography to obtain the pure product. The product was recrystallized from toluene and ethyl acetate to obtain a pale yellow solid powder, namely organic compound M20, with a yield of 34.9%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound M20 was: MS(ASAP) = 1111.

[0182] Example 6

[0183] The synthetic route for organic compound M24 is as follows:

[0184]

[0185] Synthesis of intermediate 24-2:

[0186] Intermediate 16-6 (10 mmol), compound 24-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-biscyclohexylphosphine-2',6'-dimethoxy-1,1'-diphenyl, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted, washed with water, and separated. Organic phase column chromatography was performed to give intermediate 24-2 with a molar amount of 7.63 mmol and a yield of 76.3%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 24-2 was: MS(ASAP) = 281.

[0187] Synthesis of intermediate 24-3:

[0188] Intermediate 24-2 (10 mmol), compound 1-2 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-bicyclohexylphosphine-2',6'-dimethoxy-1,1'-diphenyl, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted, washed with water, and separated. Organic phase column chromatography was performed to obtain intermediate 24-3 with a molar amount of 6.55 mmol and a yield of 65.5%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 24-3 was: MS(ASAP) = 469.

[0189] Synthesis of intermediate 24-4:

[0190] Intermediate 24-3 (10 mmol), intermediate 16-5 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-diphenyl, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 120 °C for 3 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, followed by extraction, washing with water, and separation. Organic phase column chromatography and recrystallization yielded intermediate 24-4 with a molar amount of 5.64 mmol, yield: 56.4%. Atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate 24-4: MS(ASAP) = 1137.

[0191] Synthesis of organic compound M24:

[0192] In a 250 mL three-necked flask, 10 mmol of intermediate 24-4 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a hexane solution of t-BuLi (tert-butyllithium) (21 mmol) was added dropwise. The temperature was raised to 60 °C and the reaction was carried out for 2 hours. The hexane solvent was then removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and boron tribromide (21 mmol) was added. The mixture was stirred at room temperature for 0.5 hours, and then cooled to 0 °C. 42 mmol of boron tribromide was added... N,N-Diisopropylethylamine was added dropwise, and the mixture was heated to room temperature and stirred. The temperature was then increased to 120°C and stirred for 3 hours. The reaction solution was cooled to room temperature. Sodium carbonate aqueous solution was added and ethyl acetate was added to quench the reaction. The aqueous phase was extracted with ethyl acetate and the organic phases were combined. The solvent was removed by rotary evaporation to obtain the crude product. The crude product was purified by rapid silica gel column chromatography to obtain the pure product. The product was recrystallized from toluene and ethyl acetate to obtain a pale yellow solid powder, namely organic compound M24, with a yield of 30.3%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound M24 was: MS(ASAP) = 1111.

[0193] Example 7

[0194] The synthetic route for organic compound M25 is as follows:

[0195]

[0196] Synthesis of intermediate 25-1:

[0197] Intermediate 1-5 (10 mmol), compound 24-2 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-biscyclohexylphosphine-2',6'-dimethoxy-1,1'-diphenyl, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted, washed with water, and separated. Organic phase column chromatography was performed to obtain intermediate 25-1 with a molar amount of 8.47 mmol and a yield of 84.7%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 25-1 was: MS(ASAP) = 726.

[0198] Synthesis of intermediate 25-2:

[0199] Intermediate 25-1 (10 mmol), compound 1-8 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-bicyclohexylphosphine-2',6'-dimethoxy-1,1'-diphenyl, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted, washed with water, and separated. Organic phase column chromatography was performed to obtain intermediate 25-2 with a molar amount of 6.48 mmol and a yield of 64.8%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 25-2 was: MS(ASAP) = 892.

[0200] Synthesis of intermediate 25-3:

[0201] Intermediate 25-2 (10 mmol) and intermediate 1-10 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (2 1 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The mixture was stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, followed by extraction and washing with water. The mixture was then separated by organic phase column chromatography and recrystallization to obtain intermediate 25-3 with a molar amount of 7.79 mmol and a yield of 77.9%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 25-3 was MS(ASAP) = 1137.

[0202] Synthesis of organic compound M25:

[0203] In a 250 mL three-necked flask, 10 mmol of intermediate 25-3 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a hexane solution of t-BuLi (tert-butyllithium) (21 mmol) was added dropwise. The temperature was raised to 60 °C and the reaction was carried out for 2 hours. The hexane solvent was then removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and boron tribromide (21 mmol) was added. The mixture was stirred at room temperature for 0.5 hours, and then cooled to 0 °C. 42 mmol of boron tribromide was added... N,N-Diisopropylethylamine was added dropwise, and the mixture was heated to room temperature and stirred. The temperature was then increased to 120°C and stirred for 3 hours. The reaction solution was cooled to room temperature. Sodium carbonate aqueous solution was added and ethyl acetate was added to quench the reaction. The aqueous phase was extracted with ethyl acetate and the organic phases were combined. The solvent was removed by rotary evaporation to obtain the crude product. The crude product was purified by rapid silica gel column chromatography to obtain the pure product. The product was recrystallized from toluene and ethyl acetate to obtain a pale yellow solid powder, namely organic compound M25, with a yield of 46.1%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound M25 was: MS(ASAP) = 1111.

[0204] Example 8

[0205] The synthetic route for organic compound M26 is as follows:

[0206]

[0207] Synthesis of intermediate 26-1:

[0208] Intermediate 1-5 (10 mmol), compound 16-8 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-diphenyl, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted, washed with water, and separated. Organic phase column chromatography was performed to give intermediate 26-1 with a molar amount of 8.66 mmol and a yield of 86.6%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 26-1 was: MS(ASAP) = 726.

[0209] Synthesis of intermediate 26-2:

[0210] Intermediate 26-1 (10 mmol), compound 1-8 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-bicyclohexylphosphine-2',6'-dimethoxy-1,1'-diphenyl, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted, washed with water, and separated. Organic phase column chromatography was performed to obtain intermediate 26-2 with a molar amount of 6.09 mmol and a yield of 60.9%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 26-2 was: MS(ASAP) = 892.

[0211] Synthesis of intermediate 26-3:

[0212] Intermediate 26-2 (10 mmol) and intermediate 1-10 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (2 1 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The mixture was stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, followed by extraction and washing with water. The mixture was then separated by organic phase column chromatography and recrystallization to obtain intermediate 26-3 with a molar amount of 7.13 mmol and a yield of 71.3%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate 26-3 was MS(ASAP) = 1137.

[0213] Synthesis of organic compound M26:

[0214] In a 250 mL three-necked flask, 10 mmol of intermediate 26-3 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a hexane solution of t-BuLi (tert-butyllithium) (21 mmol) was added dropwise. The temperature was raised to 60 °C and the reaction was carried out for 2 hours. The hexane solvent was then removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and boron tribromide (21 mmol) was added. The mixture was stirred at room temperature for 0.5 hours, and then cooled to 0 °C. 42 mmol of boron tribromide was added... N,N-Diisopropylethylamine was added dropwise, and the mixture was heated to room temperature and stirred. The temperature was then increased to 120°C and stirred for 3 hours. The reaction solution was cooled to room temperature. Sodium carbonate aqueous solution was added and ethyl acetate was added to quench the reaction. The aqueous phase was extracted with ethyl acetate and the organic phases were combined. The solvent was removed by rotary evaporation to obtain the crude product. The crude product was purified by rapid silica gel column chromatography to obtain the pure product. The product was recrystallized from toluene and ethyl acetate to obtain a pale yellow solid powder, namely organic compound M26, with a yield of 32.5%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound M26 was: MS(ASAP) = 1111.

[0215] Example 9

[0216] The synthetic route for organic compound M96 is as follows:

[0217]

[0218] Synthesis of intermediate 96-3:

[0219] Intermediate 96-1 (20 mmol) and compound 96-2 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (2 1 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The mixture was stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted, washed with water, and separated. Organic phase column chromatography was performed to obtain intermediate 96-3 with a molar amount of 7.29 mmol and a yield of 72.9%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 96-3 was: MS(ASAP) = 357.

[0220] Synthesis of intermediate 96-4:

[0221] Intermediate 96-3 (10 mmol), compound 1-2 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-bicyclohexylphosphine-2',6'-dimethoxy-1,1'-diphenyl, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted, washed with water, and separated. Organic phase column chromatography was performed to obtain intermediate 96-4 with a molar amount of 6.12 mmol and a yield of 61.2%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 96-4 was: MS(ASAP) = 545.

[0222] Synthesis of intermediate 96-5:

[0223] Intermediate 96-4 (10 mmol), intermediate 16-5 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-diphenyl, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 120 °C for 3 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, followed by extraction, washing with water, and separation. Organic phase column chromatography and recrystallization yielded intermediate 96-5 with a molar amount of 5.29 mmol, yield: 52.9%. Atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate 96-5: MS(ASAP) = 1215.

[0224] Synthesis of organic compound M96:

[0225] In a 250 mL three-necked flask, 10 mmol of intermediate 96-5 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a hexane solution of t-BuLi (tert-butyllithium) (21 mmol) was added dropwise. The temperature was raised to 60 °C and the reaction was carried out for 2 hours. The hexane solvent was then removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and boron tribromide (21 mmol) was added. The mixture was stirred at room temperature for 0.5 hours, and then cooled to 0 °C. 42 mmol of boron tribromide was added... N,N-Diisopropylethylamine was added dropwise, and the mixture was heated to room temperature and stirred. The temperature was then increased to 120°C and stirred for 3 hours. The reaction solution was cooled to room temperature. Sodium carbonate aqueous solution was added and ethyl acetate was added to quench the reaction. The aqueous phase was extracted with ethyl acetate and the organic phases were combined. The solvent was removed by rotary evaporation to obtain the crude product. The crude product was purified by rapid silica gel column chromatography to obtain the pure product. The product was recrystallized from toluene and ethyl acetate to obtain a pale yellow solid powder, namely organic compound M96, with a yield of 41.1%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound M96 was: MS(ASAP) = 1187.

[0226] Example 10

[0227] The synthetic route for organic compound M100 is as follows:

[0228]

[0229] Synthesis of intermediate 100-2:

[0230] Intermediate 96-1 (20 mmol) and compound 100-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (2 1 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The mixture was stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted, washed with water, and separated. Organic phase column chromatography was performed to obtain intermediate 100-2 with a molar amount of 7.67 mmol and a yield of 76.7%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 100-2 was: MS(ASAP) = 357.

[0231] Synthesis of intermediate 100-3:

[0232] Intermediate 100-2 (10 mmol), compound 1-2 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-bicyclohexylphosphine-2',6'-dimethoxy-1,1'-diphenyl, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted, washed with water, and separated. Organic phase column chromatography was performed to obtain intermediate 100-3 with a molar amount of 6.59 mmol and a yield of 65.9%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 100-3 was: MS(ASAP) = 545.

[0233] Synthesis of intermediate 100-4:

[0234] Intermediate 100-3 (10 mmol), intermediate 16-5 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-diphenyl, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 120 °C for 3 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, followed by extraction, washing with water, and separation. Organic phase column chromatography and recrystallization yielded intermediate 100-4 with a molar amount of 6.33 mmol, yield: 63.3%. Atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate 100-4: MS(ASAP) = 1213.

[0235] Synthesis of organic compound M100:

[0236] In a 250 mL three-necked flask, 10 mmol of intermediate 100-4 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a hexane solution of t-BuLi (tert-butyllithium) (21 mmol) was added dropwise. The temperature was raised to 60 °C and the reaction was carried out for 2 hours. The hexane solvent was then removed by vacuum distillation. The reaction solution was cooled again to -30 °C, and boron tribromide (21 mmol) was added. The mixture was stirred at room temperature for 0.5 hours, and then cooled to 0 °C. 42 mmol of boron tribromide was added... N,N-Diisopropylethylamine was added dropwise, and the mixture was heated to room temperature and stirred. The temperature was then increased to 120°C and stirred for 3 hours. The reaction solution was cooled to room temperature. Sodium carbonate aqueous solution was added and ethyl acetate was added to quench the reaction. The aqueous phase was extracted with ethyl acetate and the organic phases were combined. The solvent was removed by rotary evaporation to obtain the crude product. The crude product was purified by rapid silica gel column chromatography to obtain the pure product. The product was recrystallized from toluene and ethyl acetate to obtain a pale yellow solid powder, namely organic compound M100, with a yield of 43.9%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound M100 was: MS(ASAP) = 1187.

[0237] Example 11

[0238] The synthetic route for organic compound M104 is as follows:

[0239]

[0240] Synthesis of intermediate 104-2:

[0241] Intermediate 96-1 (20 mmol) and compound 104-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (2 1 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The mixture was stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted, washed with water, and separated. Organic phase column chromatography was performed to obtain intermediate 104-2 with a molar amount of 7.11 mmol and a yield of 71.1%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 104-2 was: MS(ASAP) = 357.

[0242] Synthesis of intermediate 104-3:

[0243] Intermediate 104-2 (10 mmol), compound 1-2 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-diphenyl, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted, washed with water, and separated. Organic phase column chromatography was performed to obtain intermediate 104-3 with a molar amount of 5.71 mmol and a yield of 57.1%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate 104-3 was: MS(ASAP) = 545.

[0244] Synthesis of intermediate 104-4:

[0245] Intermediate 104-3 (10 mmol), intermediate 16-5 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-diphenyl, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 120 °C for 3 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, followed by extraction, washing with water, and separation. Organic phase column chromatography and recrystallization yielded intermediate 104-4 with a molar amount of 6.91 mmol, yield: 69.1%. Atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate 104-4: MS(ASAP) = 1213.

[0246] Synthesis of organic compound M104:

[0247] In a 250 mL three-necked flask, 10 mmol of intermediate 104-4 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a hexane solution of t-BuLi (tert-butyllithium) (21 mmol) was added dropwise. The temperature was raised to 60 °C and the reaction was carried out for 2 hours. The hexane solvent was then removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and boron tribromide (21 mmol) was added. The mixture was stirred at room temperature for 0.5 hours, and then cooled to 0 °C. 42 mmol of boron tribromide was added... N,N-Diisopropylethylamine was added dropwise, and the mixture was heated to room temperature and stirred. The temperature was then increased to 120°C and stirred for 3 hours. The reaction solution was cooled to room temperature. Sodium carbonate aqueous solution was added and ethyl acetate was added to quench the reaction. The aqueous phase was extracted with ethyl acetate and the organic phases were combined. The solvent was removed by rotary evaporation to obtain the crude product. The crude product was purified by rapid silica gel column chromatography to obtain the pure product. The product was recrystallized from toluene and ethyl acetate to obtain a pale yellow solid powder, namely organic compound M104, with a yield of 41.8%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound M104 was: MS(ASAP) = 1187.

[0248] Example 12

[0249] The synthetic route for organic compound M122 is as follows:

[0250]

[0251] Synthesis of intermediate 122-2:

[0252] Intermediate 1-5 (10 mmol), compound 122-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-biscyclohexylphosphine-2',6'-dimethoxy-1,1'-diphenyl, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted, washed with water, and separated. Organic phase column chromatography was performed to obtain intermediate 122-2 with a molar amount of 8.36 mmol and a yield of 83.6%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 122-2 was: MS(ASAP) = 690.

[0253] Synthesis of intermediate 122-3:

[0254] Intermediate 122-2 (10 mmol), compound 1-8 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-bicyclohexylphosphine-2',6'-dimethoxy-1,1'-diphenyl, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted, washed with water, and separated. Organic phase column chromatography was performed to obtain intermediate 122-3 with a molar amount of 54.9 mmol and a yield of 54.9%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate 122-3 was: MS(ASAP) = 856.

[0255] Synthesis of intermediate 122-4:

[0256] Intermediate 122-3 (10 mmol) and intermediate 1-10 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (2 1 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The mixture was stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, followed by extraction and washing with water. The mixture was then separated by organic phase column chromatography and recrystallization to obtain intermediate 122-4 with a molar amount of 6.86 mmol, yield: 68.6%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate 122-4 was: MS(ASAP) = 1101.

[0257] Synthesis of organic compound M122:

[0258] In a 250 mL three-necked flask, 10 mmol of intermediate 122-4 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a hexane solution of t-BuLi (tert-butyllithium) (21 mmol) was added dropwise. The temperature was raised to 60 °C and the reaction was carried out for 2 hours. The hexane solvent was then removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and boron tribromide (21 mmol) was added. The mixture was stirred at room temperature for 0.5 hours, and then cooled to 0 °C. 42 mmol of boron tribromide was added... N,N-Diisopropylethylamine was added dropwise, and the mixture was heated to room temperature and stirred. The temperature was then increased to 120°C and stirred for 3 hours. The reaction solution was cooled to room temperature. Sodium carbonate aqueous solution was added and ethyl acetate was added to quench the reaction. The aqueous phase was extracted with ethyl acetate and the organic phases were combined. The solvent was removed by rotary evaporation to obtain the crude product. The crude product was purified by rapid silica gel column chromatography to obtain the pure product. The product was recrystallized from toluene and ethyl acetate to obtain a pale yellow solid powder, namely organic compound M124, with a yield of 38.5%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound M124 was: MS(ASAP) = 1075.

[0259] Example 13

[0260] The synthetic route for organic compound M136 is as follows:

[0261]

[0262] Synthesis of intermediate 136-2:

[0263] Intermediate 24-3 (10 mmol), intermediate 136-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-diphenyl, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 120 °C for 3 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, followed by extraction, washing with water, and separation. Organic phase column chromatography and recrystallization yielded intermediate 136-2 with a molar amount of 6.58 mmol, yield: 65.8%. Atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate 136-2: MS(ASAP) = 691.

[0264] Synthesis of intermediate 136-3:

[0265] Intermediate 136-2 (10 mmol), compound 16-4 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-biscyclohexylphosphine-2',6'-dimethoxy-1,1'-diphenyl, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted, washed with water, and separated. Organic phase column chromatography was performed to obtain intermediate 136-3 with a molar amount of 7.36 mmol and a yield of 73.6%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 136-3 was: MS(ASAP) = 1171.

[0266] Synthesis of intermediate 136-5:

[0267] Intermediate 136-3 (10 mmol), compound 136-4 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-diphenyl, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted, washed with water, and separated. Organic phase column chromatography was performed to obtain intermediate 136-5 with a molar amount of 5.87 mmol and a yield of 58.7%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 136-5 was: MS(ASAP) = 1304.

[0268] Synthesis of organic compound M136:

[0269] In a 250 mL three-necked flask, 10 mmol of intermediate 136-5 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a hexane solution of t-BuLi (tert-butyllithium) (21 mmol) was added dropwise. The temperature was raised to 60 °C and the reaction was carried out for 2 hours. The hexane solvent was then removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and boron tribromide (21 mmol) was added. The mixture was stirred at room temperature for 0.5 hours, and then cooled to 0 °C. 42 mmol of boron tribromide was added... N,N-Diisopropylethylamine was added dropwise, and the mixture was heated to room temperature and stirred. The temperature was then increased to 120°C and stirred for 3 hours. The reaction solution was cooled to room temperature. Sodium carbonate aqueous solution was added and ethyl acetate was added to quench the reaction. The aqueous phase was extracted with ethyl acetate and the organic phases were combined. The solvent was removed by rotary evaporation to obtain the crude product. The crude product was purified by rapid silica gel column chromatography to obtain the pure product. The product was recrystallized from toluene and ethyl acetate to obtain a pale yellow solid powder, namely organic compound M136, with a yield of 27.6%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound M136 was: MS(ASAP) = 1278.

[0270] Example 14

[0271] The synthetic route for organic compound M150 is as follows:

[0272]

[0273] Synthesis of intermediate 150-2:

[0274] Intermediate 150-1 (10 mmol) and intermediate 1-10 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (2 1 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The mixture was stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, followed by extraction and washing with water. The mixture was then separated by organic phase column chromatography and recrystallization to obtain intermediate 150-2 with a molar amount of 7.33 mmol, yield: 73.3%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 150-2 was: MS(ASAP) = 375.

[0275] Synthesis of intermediate 150-3:

[0276] Compound 150-2 (10 mmol), compound 1-2 (10 mmol), Pd(dba)2 (bis(dibenzylacetone)palladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted, washed with water, and separated. Organic phase column chromatography was performed to give intermediate 150-3 with a molar amount of 8.11 mmol and a yield of 81.1%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 150-3 was: MS(ASAP) = 563.

[0277] Synthesis of intermediate 150-4:

[0278] Compound 150-3 (10 mmol), compound 1-4 (10 mmol), Pd(dba)2 (bis(dibenzylacetone)palladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted, washed with water, and separated. Organic phase column chromatography was performed to give intermediate 150-4 with a molar amount of 6.81 mmol and a yield of 68.1%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 150-4 was: MS(ASAP) = 707.

[0279] Synthesis of intermediate 150-5:

[0280] Intermediate 150-4 (10 mmol), compound 1-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-biscyclohexylphosphine-2',6'-dimethoxy-1,1'-diphenyl, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted, washed with water, and separated. Organic phase column chromatography was performed to obtain intermediate 150-5 with a molar amount of 7.36 mmol and a yield of 73.6%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 150-5 was: MS(ASAP) = 820.

[0281] Synthesis of intermediate 150-7:

[0282] Intermediate 150-5 (10 mmol), compound 150-6 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-bicyclohexylphosphine-2',6'-dimethoxy-1,1'-diphenyl, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted, washed with water, and separated. Organic phase column chromatography was performed to obtain intermediate 150-7 with a molar amount of 5.11 mmol and a yield of 51.1%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 150-7 was: MS(ASAP) = 1137.

[0283] Synthesis of organic compound M150:

[0284] In a 250 mL three-necked flask, 10 mmol of intermediate 150-7 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a hexane solution of t-BuLi (tert-butyllithium) (21 mmol) was added dropwise. The temperature was raised to 60 °C and the reaction was carried out for 2 hours. The hexane solvent was then removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and boron tribromide (21 mmol) was added. The mixture was stirred at room temperature for 0.5 hours, and then cooled to 0 °C. 42 mmol of boron tribromide was added... N,N-Diisopropylethylamine was added dropwise, and the mixture was heated to room temperature and stirred. The temperature was then increased to 120°C and stirred for 3 hours. The reaction solution was cooled to room temperature. Sodium carbonate aqueous solution was added and ethyl acetate was added to quench the reaction. The aqueous phase was extracted with ethyl acetate and the organic phases were combined. The solvent was removed by rotary evaporation to obtain the crude product. The crude product was purified by rapid silica gel column chromatography to obtain the pure product. The product was recrystallized from toluene and ethyl acetate to obtain a pale yellow solid powder, namely organic compound M150, with a yield of 33.8%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound M150 was: MS(ASAP) = 1111.

[0285] Example 15

[0286] The synthetic route for organic compound M177 is as follows:

[0287]

[0288] Synthesis of intermediate 177-3:

[0289] Intermediate 177-1 (10 mmol) and intermediate 177-2 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (2 1 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The mixture was stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, followed by extraction and washing with water. The mixture was then separated by organic phase column chromatography and recrystallization to obtain intermediate 177-3 with a molar amount of 7.19 mmol and a yield of 71.9%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 177-3 was MS(ASAP) = 413.

[0290] Synthesis of intermediate 177-4:

[0291] Compound 177-3 (10 mmol), compound 16-5 (10 mmol), Pd(dba)2 (bis(dibenzylacetone)palladium, 0.1 mmol), TTBP (tri-tert-butylphosphine, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted, washed with water, and separated. Organic phase column chromatography was performed to give intermediate 177-4 with a molar amount of 8.37 mmol and a yield of 83.7%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 177-4 was: MS(ASAP) = 1081.

[0292] Synthesis of intermediate 177-6:

[0293] Intermediate 177-4 (10 mmol), intermediate 177-5 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-diphenyl, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 120 °C for 3 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, followed by extraction, washing with water, and separation. Organic phase column chromatography and recrystallization yielded intermediate 177-6 with a molar amount of 8.21 mmol, yield: 82.1%. Atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate 177-6: MS(ASAP) = 1213.

[0294] Synthesis of organic compound M177:

[0295] In a 250 mL three-necked flask, 10 mmol of intermediate 177-6 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a hexane solution of t-BuLi (tert-butyllithium) (21 mmol) was added dropwise. The temperature was raised to 60 °C and the reaction was carried out for 2 hours. The hexane solvent was then removed by vacuum distillation. The reaction solution was cooled again to -30 °C, and boron tribromide (21 mmol) was added. The mixture was stirred at room temperature for 0.5 hours, and then cooled to 0 °C. 42 mmol of boron tribromide was added... N,N-Diisopropylethylamine was added dropwise, and the mixture was heated to room temperature and stirred. The temperature was then increased to 120°C and stirred for 3 hours. The reaction solution was cooled to room temperature. Sodium carbonate aqueous solution was added and ethyl acetate was added to quench the reaction. The aqueous phase was extracted with ethyl acetate and the organic phases were combined. The solvent was removed by rotary evaporation to obtain the crude product. The crude product was purified by rapid silica gel column chromatography to obtain the pure product. The product was recrystallized from toluene and ethyl acetate to obtain a pale yellow solid powder, namely organic compound M177, with a yield of 27.8%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound M177 was: MS(ASAP) = 1187.

[0296] Example 16

[0297] The synthetic route for organic compound M219 is as follows:

[0298]

[0299] Synthesis of intermediate 219-3:

[0300] Intermediate 219-1 (10 mmol) and intermediate 219-2 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (2 1 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The mixture was stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, followed by extraction and washing with water. The mixture was then separated by organic phase column chromatography and recrystallization to obtain intermediate 219-3 with a molar amount of 7.87 mmol and a yield of 78.7%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 219-3 was MS(ASAP) = 230.

[0301] Synthesis of intermediate 219-4:

[0302] Intermediate 219-3 (20 mmol), compound 1-2 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-biscyclohexylphosphine-2',6'-dimethoxy-1,1'-diphenyl, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted, washed with water, and separated. Organic phase column chromatography was performed to obtain intermediate 219-4 with a molar amount of 5.77 mmol and a yield of 57.7%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate 219-4 was: MS(ASAP) = 418.

[0303] Synthesis of intermediate 219-5:

[0304] Intermediate 219-4 (10 mmol), compound 1-4 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-bicyclohexylphosphine-2',6'-dimethoxy-1,1'-diphenyl, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under a nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted, washed with water, and separated. Organic phase column chromatography was performed to give intermediate 219-5 with a molar amount of 6.78 mmol and a yield of 67.8%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 219-5 was: MS(ASAP) = 562.

[0305] Synthesis of intermediate 219-7:

[0306] Intermediate 219-5 (10 mmol), intermediate 219-6 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-diphenyl, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 120 °C for 3 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, followed by extraction, washing with water, and separation. Organic phase column chromatography and recrystallization yielded intermediate 219-7 with a molar amount of 8.13 mmol, yield: 81.3%. Atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate 219-7: MS(ASAP) = 669.

[0307] Synthesis of intermediate 219-9:

[0308] Intermediate 219-7 (10 mmol), intermediate 219-8 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-diphenyl, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 120 °C for 3 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, followed by extraction, washing with water, and separation. Organic phase column chromatography and recrystallization yielded intermediate 219-9 with a molar amount of 8.38 mmol, yield: 83.8%. Atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate 219-9: MS(ASAP) = 938.

[0309] Synthesis of organic compound M219:

[0310] In a 250 mL three-necked flask, 10 mmol of intermediate 219-9 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a hexane solution of t-BuLi (tert-butyllithium) (21 mmol) was added dropwise. The temperature was raised to 60 °C and the reaction was carried out for 2 hours. The hexane solvent was then removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and boron tribromide (21 mmol) was added. The mixture was stirred at room temperature for 0.5 hours, and then cooled to 0 °C. 42 mmol of boron tribromide was added... N,N-Diisopropylethylamine was added dropwise, and the mixture was heated to room temperature and stirred. The temperature was then increased to 120°C and stirred for 3 hours. The reaction solution was cooled to room temperature. Sodium carbonate aqueous solution was added and ethyl acetate was added to quench the reaction. The aqueous phase was extracted with ethyl acetate and the organic phases were combined. The solvent was removed by rotary evaporation to obtain the crude product. The crude product was purified by rapid silica gel column chromatography to obtain the pure product. The product was recrystallized from toluene and ethyl acetate to obtain a pale yellow solid powder, namely organic compound M219, with a yield of 43.2%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound M219 was: MS(ASAP) = 912.

[0311] Example 17

[0312] The synthetic route for organic compound M220 is as follows:

[0313]

[0314] Synthesis of intermediate 220-2:

[0315] Intermediate 220-1 (10 mmol), compound 1-2 (10 mmol), Pd2(dba)3 (0.1 mmol), S-Phos (2-bicyclohexylphosphine-2',6'-dimethoxy-1,1'-diphenyl, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 100 °C for 6 h under nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted, washed with water, and separated. Organic phase column chromatography was performed to obtain intermediate 220-2 with a molar amount of 8.31 mmol and a yield of 83.1%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 220-2 was: MS(ASAP) = 357.

[0316] Synthesis of intermediate 220-3:

[0317] Intermediate 220-2 (10 mmol), intermediate 1-4 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-diphenyl, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 120 °C for 3 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, followed by extraction, washing with water, and separation. Organic phase column chromatography and recrystallization yielded intermediate 220-3 with a molar amount of 7.35 mmol, yield: 73.5%. Atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate 220-3: MS(ASAP) = 501.

[0318] Synthesis of intermediate 220-4:

[0319] Intermediate 220-3 (10 mmol), intermediate 1-1 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-diphenyl, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 120 °C for 3 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, followed by extraction, washing with water, and separation. Organic phase column chromatography and recrystallization yielded intermediate 220-4 with a molar amount of 7.88 mmol, yield: 78.8%. Atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate 220-4: MS(ASAP) = 614.

[0320] Synthesis of intermediate 220-6:

[0321] Intermediate 220-4 (10 mmol), intermediate 220-5 (10 mmol), Pd-132 (bis(di-tert-butyl-4-dimethylaminophenylphosphine)palladium chloride, 0.1 mmol), S-Phos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-diphenyl, 0.2 mmol), and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred at 120 °C for 3 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, followed by extraction, washing with water, and separation. Organic phase column chromatography and recrystallization yielded intermediate 220-6 with a molar amount of 7.17 mmol, yield: 71.7%. Atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate 220-6: MS(ASAP) = 969.

[0322] Synthesis of organic compound M220:

[0323] In a 250 mL three-necked flask, 10 mmol of intermediate 220-6 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a hexane solution of t-BuLi (tert-butyllithium) (21 mmol) was added dropwise. The temperature was raised to 60 °C and the reaction was carried out for 2 hours. The hexane solvent was then removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and boron tribromide (21 mmol) was added. The mixture was stirred at room temperature for 0.5 hours, and then cooled to 0 °C. 42 mmol of boron tribromide was added... N,N-Diisopropylethylamine was added dropwise, and the mixture was heated to room temperature and stirred. The temperature was then increased to 120°C and stirred for 3 hours. The reaction solution was cooled to room temperature. Sodium carbonate aqueous solution was added and ethyl acetate was added to quench the reaction. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The solvent was removed by rotary evaporation to obtain the crude product, which was then purified by rapid silica gel column chromatography to obtain the pure product. Recrystallization from toluene and ethyl acetate yielded a pale yellow solid powder, namely organic compound M220, with a yield of 41.2%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of organic compound M220 was: MS(ASAP) = 943. The proton NMR spectrum of organic compound M220 is shown below. Figure 1 As shown, 1 HNMR(400MHz, CDCl3)δ8.57(s,1H),7.97-7.78(m,4H),7.72(s,1H),7.65-7.57(m,3H),7.43(dd,J=34.4,12.1Hz,8H),7.3 1(d,J=7.3Hz,1H),6.80(d,J=8.1Hz,5H),6.56(d,J=8.2Hz,5H),6.39(dd,J=33.9,8.3Hz,2H),1.50(s,9H),1.10(s,27H).

[0324] The embodiments of this application also provide a mixture comprising the organic compound described in the above embodiments and at least one organic functional material; in some embodiments, when the mixture provided in the embodiments of this application is used in an organic light-emitting device, 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 materials, host materials, or organic dyes.

[0325] In addition, embodiments of this application also provide a composition comprising the organic compound described in the above embodiments and at least one organic solvent, or the composition comprising the mixture described in the above embodiments and at least one organic solvent.

[0326] In some embodiments, the composition may be a solution or a suspension, and the composition may include a dispersed phase and a dispersant. The dispersed phase is one or more organic compounds as described above and at least one organic solvent, or the dispersed phase is a mixture as described above, and the dispersant is used to disperse the dispersed phase.

[0327] In the composition, the mass fraction of the organic compound as described in the above examples can be from 0.3% to 30%, preferably from 0.5% to 20%, more preferably from 0.5% to 15%, further preferably from 0.5% to 10%, and most preferably from 1% to 5%.

[0328] When the composition is used in a printing process, the composition can be an ink. The viscosity and surface tension of the ink are important parameters. Suitable surface tension parameters of the ink are suitable for specific substrates and specific printing methods. In some embodiments, the surface tension of the ink at the operating temperature or 25°C ranges from 19 dyne / cm to 50 dyne / cm; preferably from 22 dyne / cm to 35 dyne / cm; more preferably from 25 dyne / cm to 33 dyne / cm, which is beneficial for application in inkjet printing processes. In some embodiments, the viscosity of the ink at the operating temperature or 25°C ranges from 1 cps to 100 cps; preferably from 1 cps to 50 cps; more preferably from 1.5 cps to 20 cps; and most preferably from 4.0 cps to 20 cps, which is beneficial for application in inkjet printing processes.

[0329] In some embodiments, the Hansen solubility parameter of the dispersant is within the following range: the δd (dispersion force) of the dispersant is between 17.0 and 23.2 MPa. 1 / 2 The preferred range is 18.5–21.0 MPa. 1 / 2 The range; δp (polar force) is 0.2–12.5 MPa. 1 / 2 The preferred range is 2.0–6.0 MPa. 1 / 2 The range; δh (hydrogen bond force) is in the range of 0.9–14.2 MPa. 1 / 2 The preferred range is 2.0–6.0 MPa. 1 / 2 The range.

[0330] In some embodiments, the dispersant has a boiling point greater than or equal to 150°C; preferably greater than or equal to 180°C; even more preferably greater than or equal to 200°C; more preferably greater than or equal to 250°C; further preferably greater than or equal to 275°C; and most preferably greater than or equal to 300°C. A boiling point of at least 150°C is beneficial in preventing nozzle clogging of the inkjet printhead during inkjet printing, and a higher boiling point is more conducive to preventing clogging.

[0331] The dispersant may include at least one organic solvent, which can evaporate from the solvent system to form a thin film containing the functional material. The organic solvent may include at least one first organic solvent, which may be selected from aromatic or heteroaromatic compounds. Specifically, the first organic solvent may be selected from p-diisopropylbenzene, pentamene, tetrahydronaphthalene, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, dipentene, tripentene, pentamethylene, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, 1,2,3,4-tetramethylbenzene, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, butyric acid, dodecylbenzene, dihexylbenzene, dibutylbenzene, p-diisopropylbenzene, cyclohexylbenzene, benzylbutylbenzene, dimethylnaphthalene, 3-isopropylbenzene... Biphenyl, p-methylisopropylbenzene, 1-methylnaphthalene, 1,2,4-trichlorobenzene, 4,4-difluorodiphenylmethane, 1,2-dimethoxy-4-(1-propenyl)benzene, diphenylmethane, 2-phenylpyridine, 3-phenylpyridine, N-methyldiphenylamine, 4-isopropylbiphenyl, α,α-dichlorodiphenylmethane, 4-(3-phenylpropyl)pyridine, benzyl benzoate, 1,1-bis(3,4-dimethylphenyl)ethane, 2-isopropylnaphthalene, quinoline, isoquinoline, methyl 2-furanate, ethyl 2-furanate, etc.

[0332] The first organic solvent may be selected from aromatic ketone solvents. Specifically, the first organic solvent may be selected from 1-tetrahydronaphthone, 2-tetrahydronaphthone, 2-(phenylepoxy)tetrahydronaphthone, 6-(methoxy)tetrahydronaphthone, acetophenone, phenylacetone, benzophenone and their derivatives, such as 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylphenylacetone, 3-methylphenylacetone, 2-methylphenylacetone, etc.

[0333] The first organic solvent may be selected from aromatic ether solvents. Specifically, the first organic solvent may be selected from 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-ethylbenzene, 1,3-dipropoxybenzene, 1,2,4-trimethoxybenzene, 4-(1-propenyl)-1,2-dimethoxybenzene, 1,3-dimethoxybenzene, glycidylphenyl 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.

[0334] The first organic solvent may be selected from aliphatic ketones. Specifically, the first organic solvent may be selected from aliphatic ketones, such as 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2,5-hexanedione, 2,6,8-trimethyl-4-nonanone, frankinc, phorone, isophorone, di-n-pentyl ketone, etc.; or aliphatic ethers, such as pentanyl ether, hexane 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.

[0335] The first organic solvent can be selected from organic ester solvents. Specifically, the first solvent can be selected from alkyl octanoate, alkyl sebacate, alkyl stearate, alkyl benzoate, alkyl phenylacetate, alkyl cinnamate, alkyl oxalate, alkyl maleate, alkyl lactone, alkyl oleate, etc. Octyl octanoate, diethyl sebacate, diallyl phthalate, isononyl isononanoate, etc. are particularly preferred.

[0336] The organic solvent may further include a second organic solvent, which may be selected from one or more solvents such as methanol, ethanol, 2-methoxyethanol, dichloromethane, trichloromethane, 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, tetrahydronaphthalene, naphthane, and indene.

[0337] In addition to the dispersed phase and the dispersant, the composition may also include one or more components such as surfactants, lubricants, wetting agents, dispersants, hydrophobic agents, adhesives, etc., for adjusting viscosity, film-forming properties, improving adhesion, etc.

[0338] Please refer to Figure 2 The embodiments of this application also provide an organic light-emitting device 100, which includes: a first electrode 101 and a second electrode 102; an organic functional layer 103 located between the first electrode 101 and the second electrode 102; wherein the material of the organic functional layer 103 includes one or more organic compounds described in the above embodiments, or the material of the organic functional layer 103 includes a mixture described in the above embodiments, or the material of the organic functional layer 103 includes a composition described in the above embodiments.

[0339] In some embodiments, the first electrode 101 may be an anode, and the second electrode 102 may be a cathode.

[0340] In some embodiments, the organic light-emitting device 100 can be used as an organic light-emitting diode, organic photovoltaic cell, organic light-emitting cell, organic field-effect transistor, organic light-emitting field-effect transistor, organic laser, organic spintronic device, organic sensor, and organic plasmon emitting diode, etc., preferably an organic light-emitting diode, organic light-emitting cell, or organic light-emitting field-effect transistor.

[0341] In some embodiments, the organic light-emitting device 100 can be applied to a variety of electronic devices, such as display panels, lighting devices, and light sources.

[0342] In some embodiments, the organic functional layer 103 may be a single layer. In this case, the organic functional layer 103 is a mixture layer, which includes a first compound and a second compound. The first compound is selected from one or more organic compounds as described above, and the second compound is an organic functional material. Specifically, the second organic compound may be selected from one or more of hole injection materials, hole transport materials, electron transport materials, hole blocking materials, light-emitting guest materials, light-emitting host materials, and organic dyes. For detailed descriptions of the various organic functional materials included in the organic functional layer 103, please refer to WO2010135519A1, US20090134784A1, and WO 2011110277A1. The entire contents of these three patent documents are hereby incorporated herein by reference.

[0343] The luminescent object material is selected from singlet luminescent materials (fluorescent materials), triplet luminescent materials (phosphorescent materials), and TADF materials.

[0344] When the second compound is selected from one or more of hole injection materials, hole transport materials, electron transport materials, hole blocking materials, light-emitting host materials, and organic dyes, the mass ratio of the first compound to the second compound is 1:99 to 30:70, preferably 1:99 to 10:90.

[0345] When the second compound is a luminescent guest material, the mass ratio of the first compound to the second compound is 99:1 to 70:30, preferably 99:1 to 90:10.

[0346] In some embodiments, the organic functional layer 103 may include multiple layers. When the organic functional layer 103 is multilayered, it includes at least a light-emitting layer 107; preferably, the organic functional layer 103 includes a hole injection layer 104, a hole transport layer 105, an electron blocking layer 106, a light-emitting layer 107, an electron transport layer 108, and an electron injection layer 109 sequentially disposed on the first electrode 101; in other embodiments of this application, the organic light-emitting device may further include a hole blocking layer disposed between the light-emitting layer 107 and the electron transport layer 108.

[0347] In some embodiments, the organic light-emitting device 100 may be a blue organic light-emitting device, a green organic light-emitting device, or a red organic light-emitting device. The light-emitting layer 107 may include a host material and a guest material. The guest material may be one or more organic compounds as described above, and the host material may include fused aromatic derivatives or heteroaromatic compounds.

[0348] The emission wavelength of the organic light-emitting device 100 is between 300 and 1000 nm; further, the emission wavelength of the organic light-emitting device 100 is between 350 and 900 nm; even further, the emission wavelength of the organic light-emitting device 100 is between 400 and 800 nm; and still further, the emission wavelength of the organic light-emitting device 100 is within the wavelength range of blue light.

[0349] In some embodiments, the host material includes at least one selected from anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentane derivatives, phenanthrene compounds, fluoranthene compounds, carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, and pyrimidine derivatives. Preferably, the host material is a blue light host material used in blue organic light-emitting devices; when the host material is a blue light host material, the host material is preferably an anthracene-based organic compound.

[0350] In some embodiments, the mass ratio of the host material to the guest material is 99:1 to 70:30, such as 90:10, 85:15, 80:20, 75:25, etc.; preferably 99:1 to 90:10, such as 97:3, 96:4, 95:5, 93:7, 92:8, etc. The guest material is dispersed in the host material, and the mass ratio of the host material to the guest material is 99:1 to 70:30, which helps to suppress the crystallization of the light-emitting layer 107 and suppress the concentration quenching caused by the high concentration of the guest material, thereby improving the luminous efficiency of the organic light-emitting device 100.

[0351] In some embodiments, the anode is an electrode for injecting holes, and the anode can inject holes into the organic functional layer 103, such as by injecting holes into the hole injection layer, the hole transport layer, or the light-emitting layer. The anode may include at least one of a conductive metal, a conductive metal oxide, or a conductive polymer. Preferably, the absolute value of the difference between the work function of the anode and the HOMO (Highest Occupied Molecular Orbital) level or valence band level of the light-emitting material in the light-emitting layer or the p-type semiconductor material in the hole injection layer, hole transport layer, or electron blocking layer is less than 0.5 eV, preferably less than 0.3 eV, and more preferably less than 0.2 eV. The material of the anode includes, but is not limited to, at least one of Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO (Indium Tin Oxide), aluminum-doped zinc oxide (AZO), or other suitable and known anode materials, which can be readily selected and used by those skilled in the art. The anode material can be deposited using any suitable technique, such as suitable physical vapor deposition methods, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), etc. In some embodiments, the anode can be patterned, for example, patterned ITO conductive substrates are commercially available and can be used to fabricate the organic light-emitting device 100 of this application.

[0352] In some embodiments, the cathode is an electrode for injecting electrons, and the cathode can inject electrons into the organic functional layer, such as injecting electrons into the electron injection layer, electron transport layer, or light-emitting layer. The cathode may include at least one of a conductive metal or a conductive metal oxide. Preferably, the absolute value of the difference between the work function of the cathode and the LUMO (Lowest Unoccupied Molecular Orbital) level or conduction band level of the light-emitting material in the light-emitting layer or the n-type semiconductor material that serves as the electron injection layer, electron transport layer, or hole blocking layer is less than 0.5 eV, preferably less than 0.3 eV, and more preferably less than 0.2 eV. All materials that can be used as cathodes of organic electronic devices may be used as cathode materials for the device of this application, including 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, ITO, etc. The cathode material can be deposited using any suitable technique, such as suitable physical vapor deposition methods, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), etc.

[0353] In some embodiments, the hole injection layer 104 facilitates hole injection from the anode to the light-emitting layer 107, and the hole injection layer 104 includes a hole injection material that can receive holes injected from the positive electrode at low voltage. Preferably, the highest occupied molecular orbital (HOMO) of the hole injection material lies between the work function of the anode material and the HOMO of the functional material of the film layer on the side away from the anode (e.g., the hole transport material of the hole transport layer). The hole injection material includes, but is not limited to, at least one of metalloporphyrins, oligothiophenes, arylamine-based organic materials, hexanitrile hexaazabenzophenanthrene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinones, polyaniline-based conductive polymers, and polythiophene-based conductive polymers.

[0354] In some embodiments, the hole transport layer 105 can be used to transport holes to the light-emitting layer 107. The hole transport layer 105 includes a hole transport material that receives holes transported from the anode or the hole injection layer and transfers the holes to the light-emitting layer. The hole transport material is a material with high hole mobility known in the art, and may include, but is not limited to, at least one of arylamine-based organic materials, conductive polymers, and block copolymers having both conjugated and non-conjugated portions.

[0355] In some embodiments, the electron transport layer 108 is used to transport electrons. The electron transport layer 108 includes an electron transport material that receives electrons injected from the negative electrode and transfers the electrons to the light-emitting layer 107. The electron transport material is a material with high electron mobility known in the art, and may include, but is not limited to, at least one of: Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic radical compounds, hydroxyflavonoid-metal complexes, lithium 8-hydroxyquinoline (LiQ), and benzimidazole-based compounds.

[0356] In some embodiments, the electron injection layer 109 is used for injecting electrons. The electron injection layer 109 includes an electron injection material, which preferably has the ability to transport electrons, the effect of injecting electrons from the negative electrode, and the excellent effect of injecting electrons into the light-emitting layer 107 or the light-emitting material. It also has the ability to prevent excitons generated by the light-emitting layer 107 from migrating to the hole injection layer and has excellent thin film formation capabilities. The electron injection material includes, but is not limited to, at least one of lithium 8-hydroxyquinoline (LiQ), fluorenone, anthraquinone dimethane, biphenylquinone, thiamethane dioxide, azoles, diazoles, triazoles, imidazoles, perylenetetracarboxylic acid, fluorenemethane, anthrone, and their derivatives, metal complex compounds, and nitrogen-containing 5-membered ring derivatives.

[0357] In some embodiments, the hole blocking layer is used to block holes from reaching the negative electrode, and can typically be formed under the same conditions as the hole injection layer 104. The hole blocking layer includes a hole blocking material, which includes, but is not limited to, at least one of diazole or triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, etc.

[0358] In some embodiments, please refer to Figure 2 The organic light-emitting device 100 further includes a substrate 110, wherein the first electrode 101, the hole injection layer 104, the hole transport layer 105, the electron blocking layer 106, the light-emitting layer 107, the electron transport layer 108, the electron injection layer 109, and the second electrode 102 are sequentially stacked on the substrate 110. The substrate 110 can be a transparent substrate or an opaque substrate. When the substrate 110 is a transparent substrate, a transparent organic light-emitting device 100 can be fabricated. The substrate 110 can be a rigid substrate or a flexible substrate with elasticity. The material of the substrate 110 can include, but is not limited to, plastics, polymers, metals, semiconductor wafers, or glass. Preferably, the substrate 110 includes at least one smooth surface for forming the anode on the surface. More preferably, the surface is free of surface defects. Preferably, the substrate 110 is made of polymer film or plastic, including but not limited to polyethylene terephthalate (PET material) and polyethylene glycol (2,6-naphthalene) (PEN material). The glass transition temperature of the substrate 110 is greater than or equal to 150°C, preferably greater than or equal to 200°C, more preferably greater than or equal to 250°C, and most preferably greater than or equal to 300°C.

[0359] In some embodiments, the organic light-emitting device 100 may be a solution-type organic light-emitting device, that is, at least one of the organic functional layers is prepared by a printing method (e.g., inkjet printing).

[0360] In some embodiments, the mixture layer or the light-emitting layer can be formed by a printing or coating process of the composition. Printing or coating processes include inkjet printing, nozzle printing, letterpress printing, screen printing, dip coating, spin coating, knife coating, roller printing, torsional roller printing, offset printing, flexographic printing, rotary printing, spraying, brushing, pad printing, slot extrusion coating, etc. Preferably, gravure printing, inkjet printing, and other similar processes are used.

[0361] Continuing on the above, the boron-containing biphenyl organic compounds provided in the embodiments of this application introduce structures such as dibenzofuran, dibenzothiophene, carbazole, benzo5-membered ring, triphenylene and / or naphthalene into the boron-nitrogen compound, resulting in greater overall molecular conjugation and improving the luminous efficiency and lifespan of the organic light-emitting devices using the organic compound. Simultaneously, the introduction of tetrahydronaphthalene and / or indene structures into the boron-nitrogen compound improves the solubility of the molecule in processes such as inkjet printing, facilitating compound purification and thus increasing the purity of the organic compound, thereby further extending the luminous efficiency and lifespan of the organic light-emitting devices using the organic compound.

[0362] Furthermore, the embodiments of this application calculate the HOMO, LUMO, S1, and T1 energy levels of the organic compounds shown in Examples 1 to 17 above and the comparative compound 1 in Comparative Example 1 to verify the performance of the organic compounds provided by the embodiments of this application.

[0363] The structural formula of comparative compound 1 in Comparative Example 1 is:

[0364]

[0365] Quantum computing can be used to obtain the HOMO (Highest Occupied Molecular Orbital), LUMO (Lowest Unoccupied Molecular Orbital), T1 (first excited triplet state), and S1 (first excited singlet state) energy levels of compounds M1 to M220 obtained in Examples 1 to 17, as well as the comparative compound 1 in Comparative Example 1. Specifically, using TD-DFT (Time-dependent Density Functional Theory) via Gaussian09W (Gaussian Inc.), and with specific simulation methods as described in WO2011141110, the molecular geometry is first optimized using the semi-empirical method “Ground State / Semi-empirical / Default Spin / AM1” (Charge 0 / Spin Singlet). Then, the energy structure of the organic molecule is calculated using TD-DFT (Time-dependent Density Functional Theory) to obtain “TD-SCF / DFT / Default Spin / B3PW91” and the basis set “6-31G(d)” (Charge 0 / Spin Singlet). The HOMO and LUMO levels are calculated according to the calibration formula below, while the S1 and T1 levels are used directly.

[0366] HOMO(eV)=((HOMO(G)×27.212)-0.9899) / 1.1206

[0367] LUMO(eV)=((LUMO(G)×27.212)-2.0041) / 1.385

[0368] Among them, HOMO, LUMO, T1 and S1 are direct calculation results of Gaussian 09W, and the unit is Hartree.

[0369] Based on the above, the calculation results are shown in Table 1 below.

[0370] Table 1 Energy Level Data Table

[0371]

[0372]

[0373] As shown in Table 1, the T1 and S1 energy levels of organic compounds M1 to M220 provided in Examples 1 to 17 of this application are all higher than those of comparative compound 1. This indicates that the blue light emitted by organic compounds M1 to M220 is more deep blue than that emitted by comparative compound 1, which is beneficial for obtaining better color coordinates in blue organic light-emitting devices using the organic compounds provided in the embodiments of this application as guest materials in the light-emitting layer.

[0374] Further, please refer to Figure 3 The embodiments of this application provide, as follows: Figure 3 The exemplary fabrication steps of the organic light-emitting device 200 shown are illustrated in Exemplary Example 1 below.

[0375] Example 1

[0376] In the organic light-emitting device provided in this embodiment, ITO (indium tin oxide) is used as the anode 202, and PEDOT (polyethylene dioxythiophene, Clevios) is used. TM Al4083 was used as the material for hole injection layer 203, PVK (Sigma Aldrich, average Mn 25,000-50,000) was used as the material for hole transport layer 204, BH-1 to BH-3 were used as the host materials in the light-emitting layer 205 of the corresponding organic light-emitting device 200, organic compounds M1 to M220 in Examples 1 to 58 and comparative compound 1 in Comparative Example 1 were used as guest materials in the light-emitting layer 205 of the corresponding organic light-emitting device 200, ET and Liq (lithium 8-hydroxyquinoline) were used as the materials for electron transport layer 206, and Al was used as cathode 207. The specific preparation steps are as follows:

[0377] a. Cleaning of ITO anode 202: Clean the ITO conductive glass with chloroform, acetone and / or isopropanol, and then perform ultraviolet ozone treatment. The conductive glass includes a substrate 201 and an anode 202 formed on the substrate 201.

[0378] b. Forming the hole injection layer 203: Spin-coating the hole injection layer 203 with PEDOT (polyethylene dioxythiophene, Clevios) material onto the ITO anode 202. TM AI4083), and was treated on a hot plate at 180°C for 10 minutes, with a hole injection layer thickness of 40nm;

[0379] c. Forming hole transport layer 204: Spin-coating a toluene solution of PVK (Sigma Aldrich, Mn 25,000-50,000) with a concentration of 5 mg / ml onto hole injection layer 203, and then treating it on a hot plate at 180°C for 60 minutes. The thickness of hole transport layer 204 is 20 nm.

[0380] d. Forming the light-emitting layer 205: In a nitrogen glove box, spin-coat the light-emitting layer material onto the hole transport layer 204, and then treat it on a hot plate at 140°C for 10 minutes. The host material in the light-emitting layer 205 of different organic light-emitting devices 200 corresponds to BH-1, BH-2 or BH-3, respectively. The guest material in the light-emitting layer 205 of different organic light-emitting devices 200 corresponds to one of organic compounds M1 to M220, respectively. The solvent is methyl benzoate solution. The mass ratio of host material to guest material is 95:5. The concentration of the material in the light-emitting layer 205 is 15 mg / ml. The thickness of the final light-emitting layer 205 is 40 nm.

[0381] e. Forming an electron transport layer 206: In a vacuum chamber, above the light-emitting layer 205, ET and Liq are placed in different evaporation units, and ET and Liq are co-deposited in a weight ratio of 50:50 under a high vacuum (1×10-6 mbar) environment to form an electron transport layer 206 with a thickness of 20 nm.

[0382] f. Forming the cathode layer 207: Al is deposited on the electron transport layer 206 to obtain an Al cathode 207 with a thickness of 100 nm.

[0383] g. Packaging: The device is encapsulated in a nitrogen glove box using UV-cured resin.

[0384] Specifically, in this embodiment, organic light-emitting devices 1 to 21 and comparative elements 1 to 3 are obtained through the above steps. The guest materials used in organic light-emitting devices 1 to 17 are organic compounds M1 to M220, respectively, and the host material used in organic light-emitting devices 1 to 17 is BH-1; the guest materials used in organic light-emitting devices 18 and 20 are organic compounds M2, and the host materials used in organic light-emitting devices 18 and 20 are BH-2 and BH-3, respectively; the guest materials used in organic light-emitting devices 19 and 21 are organic compounds M3, and the host materials used in organic light-emitting devices 19 and 21 are BH-2 and BH-3, respectively; the guest material used in comparative elements 1 to 3 is comparative compound 1, and the host materials used in comparative elements 1 to 3 are BH-1, BH-2, and BH-3, respectively.

[0385] Specifically, the chemical structural formulas of BH-1, BH-2, BH-3, ET, and Liq are as follows:

[0386]

[0387] In the embodiments of this application, the current-voltage (JV) characteristics of organic light-emitting devices 1 to 21 and contrast elements 1 to 3 were tested, and the CIE color coordinates (x, y), driving voltage at 1 knits brightness (voltage@1 knits[V]), luminous efficiency (CE@1 knits[cd / A]) at a current density of 10 mA / cm2, and the time taken for the brightness to decrease from the initial brightness of 1 knits to 90% of the initial brightness (LT90@1 knits[h]) were obtained for each organic light-emitting device and contrast element. The specific results are shown in Table 2.

[0388] Table 2 Performance data of organic light-emitting devices

[0389]

[0390]

[0391] As shown in Table 2, the organic light-emitting devices 1 to 21 obtained by using guest materials M1 to M220 in the light-emitting layer in the embodiments of this application have superior color coordinates compared to the contrast elements 1 to 3. Furthermore, the luminous efficiency of organic light-emitting devices 1 to 21 is all between 5.7 and 6.6 cd / A, indicating that the luminous efficiency is much higher than that of contrast elements 1 to 3. Moreover, the time taken for the brightness of organic light-emitting devices 1 to 20 to decrease from an initial brightness of 1 knits to 90% of the initial brightness is all within the range of 131 to 179 hours, which is an improvement of 50% to 100% compared to the time taken for the brightness of contrast elements 1 to 3 to decrease from an initial brightness of 1 knits to 90% of the initial brightness, indicating that organic light-emitting devices 1 to 21 have a significantly improved lifetime.

[0392] Meanwhile, compared with Comparative Example 1, the organic compounds M1 to M220 provided in the embodiments of this application have better overall molecular solubility and are easier to purify by introducing biphenyl rings and diarylamine rings, thereby improving the purity of the compounds and thus improving the efficiency and lifespan of the organic light-emitting devices made therefrom.

[0393] Furthermore, the luminous efficiency of organic light-emitting devices 4, 5, 6, 13, 14, and 17 are all in the range of 6.2–6.6 cd / A, and their lifetimes are all around 170 hours. This is because, compared with the guest materials in other organic light-emitting devices, the overall molecular conjugation is greater. The aromatic amine combination of benzothiophene and biphenyl has a significantly better improved lifetime efficiency than the combination of benzothiophene and benzene. In addition, the number of solubilizing groups is greater, which improves the solubility of the guest material and further improves the luminous efficiency and lifetime of the organic light-emitting devices.

[0394] Furthermore, in the structure shown in general formula (2), the diarylamine and Ar1 are located on the same side of the organic compound. In the structure shown in general formula (1), the diarylamine and Ar2 are located on the same side of the organic compound. Ar1 is selected from tert-butylphenylthiophene or tert-butylbenzene, and Ar2 is selected from biphenyl-type groups. As a result, the steric hindrance of Ar2 is less than that of Ar1. Therefore, the steric hindrance on the side with Ar1 in the structure shown in general formula (2) is greater than that on the side with Ar2 in the structure shown in general formula (1). This can effectively improve the device performance of the organic light-emitting device with the organic compound shown in general formula (2). For example, the device performance of Example 14 in Table 2 is the best.

[0395] In summary, the organic light-emitting devices disclosed in the embodiments of this application improve material properties, increase luminous efficiency, and extend lifespan by using boron nitrogen compounds and introducing biphenyl, benzothiophene, and diarylamine groups into the boron nitrogen compounds to enhance the overall conjugation of the compounds.

[0396] Embodiments of this application also disclose a display panel, which includes the organic light-emitting device described in the above embodiments.

[0397] In some embodiments, the display panel further includes an array substrate located on one side of the organic light-emitting device (OLED), and an encapsulation layer located on the side of the OLED away from the array substrate and covering the OLED. The display panel also includes a polarizer layer located on the side of the encapsulation layer away from the OLED and a cover plate layer located on the side of the polarizer layer away from the OLED. The polarizer layer may be replaced by a color filter layer, which may include a plurality of color resists and black matrices located on both sides of the color resists.

[0398] The display panel disclosed in the embodiments of this application uses an organic light-emitting device containing boron nitrogen compounds, and introduces groups into the boron nitrogen compounds to enhance the overall conjugation of the compound, thereby enhancing the conjugation effect of the material applied to the organic light-emitting device, improving the material performance, increasing the luminous efficiency of the display panel, and extending the service life of the display panel.

[0399] In the above embodiments, the descriptions of each embodiment have different focuses. For parts not described in detail in a certain embodiment, please refer to the relevant descriptions in other embodiments.

[0400] The above provides a detailed description of an organic compound, mixture, composition, organic light-emitting device, and display panel provided in the embodiments of this application. Specific examples have been used to illustrate the principles and implementation methods of this application. The descriptions of the above embodiments are only for the purpose of helping to understand the technical solutions and core ideas of this application. Those skilled in the art should understand that modifications can still be made to the technical solutions described in the foregoing embodiments, or equivalent substitutions can be made to some of the technical features. These modifications or substitutions do not cause the essence of the corresponding technical solutions to deviate from the scope of the technical solutions of the embodiments of this application.

Claims

1. An organic compound, characterized in that, The organic compound has a structure as shown in general formula (1) or general formula (2): Ar1 has the structure represented by equation (X-1) or equation (X-2): Ar2 and Ar3 have the structures represented by any of equations (A-1) to (A-5): Ar2 has fusion sites on two adjacent carbon atoms in the same benzene ring, while Ar3 has linkage sites on carbon atoms in any benzene ring. n0 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14; n1 is selected from 0, 1, 2 or 3; n2 is selected from 0, 1, 2, 3, 4 or 5; n3 is selected from 0 or 1; R0, R1, R2, and R3 are selected from -H, -D, straight-chain alkyl groups with 1 to 20 carbon atoms, straight-chain alkoxy groups with 1 to 20 carbon atoms, straight-chain thioalkoxy groups with 1 to 20 carbon atoms, branched alkyl groups with 3 to 20 carbon atoms, cyclic alkyl groups with 3 to 20 carbon atoms, branched alkoxy groups with 3 to 20 carbon atoms, cyclic alkoxy groups with 3 to 20 carbon atoms, branched thioalkoxy groups with 3 to 20 carbon atoms, cyclic thioalkoxy groups with 3 to 20 carbon atoms, silyl groups, ketone groups with 1 to 20 carbon atoms, and groups with a carbon number of 1 to 20. Alkoxycarbonyl groups with 2 to 20 carbon atoms, aryloxycarbonyl groups with 7 to 20 carbon atoms, alkenyl groups with 1 to 20 carbon atoms, -CN, carbamoyl, halocarbamoyl, formyl, isocyanate, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, -CF3, -Cl, -Br, -F, substituted or unsubstituted aromatic groups with 6 to 30 ring atoms, substituted or unsubstituted heteroaromatic groups with 5 to 30 ring atoms, substituted or unsubstituted aryloxy groups with 6 to 30 ring atoms, and substituted or unsubstituted heteroaromatic groups with 5 to 30 ring atoms; When n0 is greater than or equal to 2, two adjacent R0s may or may not form a cycle; when n1 is greater than or equal to 2, two adjacent R1s may or may not form a cycle; when n2 is greater than or equal to 2, two adjacent R2s may or may not form a cycle.

2. The organic compound according to claim 1, characterized in that, The organic compound has a structure as shown in any of general formulas (2-1) to (2-23): n 01 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; In the structure shown in general formula (2), Ar1 and diarylamine are located on the same side of the organic compound.

3. The organic compound according to claim 1 or 2, characterized in that, R0, R1, R2 and R3 are selected from -H, -D, straight-chain alkyl with 1 to 10 carbon atoms, branched alkyl with 3 to 10 carbon atoms, and cyclic alkyl with 3 to 10 carbon atoms.

4. The organic compound according to claim 1 or 2, characterized in that, R0, R1, R2 and R3 are selected from straight-chain alkyl groups with -H, -D, 1 to 4 carbon atoms, and branched alkyl groups with 3 to 5 carbon atoms.

5. The organic compound according to claim 1, characterized in that, The organic compound is selected from the compounds shown in Formulas 1 to 244:

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

7. A composition, characterized in that, The composition comprises an organic compound as described in any one of claims 1 to 5 and at least one organic solvent, or the composition comprises a mixture as described in claim 6 and at least one of the organic solvents.

8. An organic light-emitting device, characterized in that, include: First electrode; The second electrode is disposed opposite to the first electrode; as well as An organic functional layer is located between the first electrode and the second electrode; The material of the organic functional layer includes one or more organic compounds as described in any one of claims 1 to 5, or the material of the organic functional layer includes the mixture described in claim 6, or the material of the organic functional layer includes the composition described in claim 7.

9. The organic light-emitting device according to claim 8, characterized in that, The organic functional layer includes at least a light-emitting layer, which includes a host material and a guest material. The guest material includes one or more of the organic compounds, and the host material includes fused aromatic derivatives or heteroaromatic compounds.

10. A display panel, characterized in that, The display panel includes the organic light-emitting device as described in claim 8 or 9.

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