Organic compounds, light-emitting elements and display panels

Abstract

This invention discloses an organic compound, a light-emitting element, and a display panel. The organic compound has a structure as shown in general formula (1). This invention improves the material properties, increases the luminous efficiency of the light-emitting element, and extends the service life of the light-emitting element by introducing groups into the boron nitrogen compound to make the compound more conjugated.

Description

Technical Field

[0001] This invention relates to the field of displays, and more specifically to an organic compound, a light-emitting element, and a display panel. Background Technology

[0002] Currently, organic light-emitting diodes (OLEDs) typically consist of a positive electrode, a negative electrode, 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 positive and negative electrodes of the OLED, holes are injected into the organic layer from the positive electrode, and electrons are injected into the organic layer from the negative electrode. 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, organic light-emitting devices 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 them, OLEDs using fluorescent materials have high reliability, but under electrical excitation, their internal electroluminescence quantum efficiency is limited to 25% due to the 1:3 branching ratio of singlet and triplet excited states of excitons. OLEDs using phosphorescent materials have achieved almost 100% internal electroluminescence quantum efficiency, but phosphorescent materials usually use metal complexes containing iridium and platinum, which are expensive and complex to synthesize. Furthermore, phosphorescent OLEDs also exhibit a roll-off effect, meaning that the luminous efficiency decreases rapidly with increasing current or brightness, limiting their application at high brightness levels.

[0004] To overcome the above problems, existing technologies typically involve 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 organic compounds with TADF is limited in terms of both efficiency and lifetime, making it difficult to improve the luminous efficiency and lifetime of organic electroluminescent devices using organic compounds with TADF.

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

[0006] This invention provides an organic compound, a light-emitting element, and a display panel, which can alleviate the technical problem that it is difficult to improve the luminous efficiency and lifespan of organic electroluminescent elements using organic compounds with TADF.

[0007] This invention provides an organic compound having a structure as shown in general formula (1):

[0008]

[0009] Wherein, any Ar1 is independently selected from the structure represented by any one of equations (A-1) to (A-5):

[0010]

[0011] Ar2 is selected from: -H, or any structure represented by equations (B-1) to (B-4):

[0012]

[0013] X is independently selected from O, S, N-CH3, N-Ph or C(CH3)2;

[0014] n0, n1, n2, and n5 are each independently selected from 0 to 11;

[0015] Each of R0, R1, R2 or R5 is independently selected from: -H, -D, straight-chain alkyl having 1 to 20 carbon atoms, branched alkyl having 3 to 20 carbon atoms, substituted or unsubstituted aromatic group having 6 to 30 cyclic atoms, and substituted or unsubstituted heteroaromatic group having 5 to 30 cyclic atoms.

[0016] 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; when n5 is greater than or equal to 2, two adjacent R5s may or may not form a cycle.

[0017] Preferably, the organic compound has a structure as shown in any one of general formulas (2-1) to (2-18):

[0018]

[0019]

[0020] Each of R3 or R4 is independently selected from: -H, -D, straight-chain alkyl having 1 to 20 carbon atoms, branched alkyl having 3 to 20 carbon atoms, substituted or unsubstituted aromatic group having 6 to 30 cyclic atoms, and substituted or unsubstituted heteroaromatic group having 5 to 30 cyclic atoms.

[0021] n3 and n4 are each independently selected from 0 to 11;

[0022] When n3 is greater than or equal to 2, two adjacent R3s may form a cycle or not; when n4 is greater than or equal to 2, two adjacent R4s may form a cycle or not.

[0023] Preferably, any one of R1, R2, R3, R4 or R5 is independently selected from -H, -D, straight-chain alkyl with 1 to 10 carbon atoms, or branched alkyl with 3 to 10 carbon atoms.

[0024] Preferably, any one of R1, R2, R3, R4 or R5 is independently selected from: -H, -D, straight-chain alkyl having 1 to 4 carbon atoms, or branched alkyl having 3 to 5 carbon atoms.

[0025] Preferably, the structure represented by formula (A-3) includes:

[0026]

[0027] The structure represented by equation (B-2) includes:

[0028] as well as At least one of them.

[0029] Preferably, the organic compound is selected from the following compounds:

[0030]

[0031]

[0032]

[0033]

[0034]

[0035]

[0036]

[0037]

[0038]

[0039]

[0040]

[0041]

[0042]

[0043]

[0044]

[0045]

[0046]

[0047]

[0048] The present invention also provides a light-emitting element, comprising: a pair of electrodes, including a first electrode and a second electrode;

[0049] An organic functional layer located between the first electrode and the second electrode;

[0050] The material of the organic functional layer includes one or more organic compounds as described in any of the preceding claims.

[0051] Preferably, 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 is one or more organic compounds as described in any of the preceding claims, and the host material includes fused aromatic derivatives or heteroaromatic compounds.

[0052] Preferably, the main material includes one or more of anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentane derivatives, phenanthrene compounds, fluoranthene compounds, carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, and pyrimidine derivatives.

[0053] The present invention also provides a display panel including a light-emitting element as described in any of the preceding claims.

[0054] This invention improves material properties, increases the luminous efficiency of light-emitting elements, and extends the lifespan of light-emitting elements by introducing groups into boron-nitrogen compounds that enhance the overall conjugation of the compounds. Attached Figure Description

[0055] To more clearly illustrate the technical solutions in the embodiments of the present invention, the accompanying drawings used in the description of the embodiments will be briefly introduced below. Obviously, the accompanying drawings described below are only some embodiments of the present invention. For those skilled in the art, other drawings can be obtained based on these drawings without creative effort.

[0056] Figure 1 This is a schematic diagram of the first structure of the light-emitting element provided in the embodiment of the present invention;

[0057] Figure 2 This is a schematic diagram of a second structure of the light-emitting element provided in an embodiment of the present invention;

[0058] Figure 3 This is the hydrogen nuclear magnetic resonance spectrum of organic compound M13 provided in the embodiments of the present invention. Detailed Implementation

[0059] The technical solutions of the embodiments of the present invention will be clearly and completely described below with reference to the accompanying drawings. Obviously, the described embodiments are only some embodiments of the present invention, and not all embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without creative effort are within the scope of protection of the present invention. In addition, it should be understood that the specific embodiments described herein are only for illustration and explanation of the present invention and are not intended to limit the present invention. In the present invention, unless otherwise stated, directional terms such as "upper" and "lower" generally refer to the upper and lower positions of the device in actual use or operation, specifically the drawing direction in the accompanying drawings; while "inner" and "outer" refer to the outline of the device. In the present invention, "optionally," "optionally," and "optional" mean that they are optional, that is, they are selected from either "with" or "without" in the parallel schemes. If multiple "optional" appear in a technical solution, unless otherwise specified, and there is no contradiction or mutual constraint relationship, each "optional" is independent. In the present invention, the technical features described in an open-ended manner include both closed technical solutions composed of the listed features and open technical solutions containing the listed features.

[0060] In this invention, aromatic groups, aromatic families, and aromatic ring systems have the same meaning and can be used interchangeably.

[0061] In this invention, heteroaromatic groups, heteroaromatic families, and heteroaromatic ring systems have the same meaning and can be used interchangeably.

[0062] In this invention, "substitution" means that the hydrogen atom in the substituent is replaced by the substituent.

[0063] In this invention, 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.

[0064] In this invention, "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 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 can be understood that R' and R" in -NR'R" are independently selected from, but not limited to: H, deuterium. 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.

[0065] In this invention, "ring atom number" refers to the number of atoms in the ring-forming structure of a compound (e.g., monocyclic compound, fused-ring compound, cross-linked compound, carbocyclic compound, heterocyclic compound) obtained by atomic bonding. 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.

[0066] In this invention, "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 ring is an aromatic ring system. For example, "substituted or unsubstituted aryl having 6 to 40 ring atoms" refers to 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, with optional further substitution 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.

[0067] In this invention, "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, O atom, 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.

[0068] In this invention, "alkyl" can refer to straight-chain, branched, and / or cyclic alkyl groups. 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 ...

[0069] In this invention, 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.

[0070] In this invention, "amino group" refers to an amine derivative having the structural feature of 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.

[0071] In this invention, 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.

[0072] In this invention, 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).

[0073] In this invention, the "*" connected to a single bond indicates a connection or fusion site.

[0074] In this invention, when no linking site is specified in the group, it means that any linkable site in the group is selected as the linking site.

[0075] In this invention, 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.

[0076] In this invention, 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.

[0077] In this invention, the single bond connecting the substituents extends 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.

[0078] According to the present invention, cycloalkyl or cycloalkyl means have the same meaning and can be used interchangeably.

[0079] In this invention, "adjacent groups" refers to two substituents that have no substituted sites between them.

[0080] In this invention, "two adjacent R1, R3, or R5 ringing together" means a ring system formed by connecting two adjacent 1, 3, or R5 rings. The ring system can be selected from aliphatic hydrocarbon rings, aliphatic heterocycles, aromatic hydrocarbon rings, or aromatic heterocycles. Preferably, it can form...

[0081] Currently, the performance of traditional organic compounds with TADF is limited in terms of both efficiency and lifespan, resulting in difficulties in improving the luminous efficiency and lifespan of organic electroluminescent elements.

[0082] This invention provides an organic compound having a structure as shown in general formula (1):

[0083]

[0084] Wherein, any Ar1 is independently selected from the structure represented by any one of equations (A-1) to (A-5):

[0085]

[0086] Ar2 is selected from: -H, or any structure represented by equations (B-1) to (B-4):

[0087]

[0088] X is independently selected from O, S, N-CH3, N-Ph or C(CH3)2;

[0089] Any one of R0, R1, R2, or R5 is independently selected from: -H, -D, a straight-chain alkyl group having 1 to 20 carbon atoms, a straight-chain alkoxy group having 1 to 20 carbon atoms, a straight-chain thioalkoxy group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, a cyclic alkyl group having 3 to 20 carbon atoms, a branched alkoxy group having 3 to 20 carbon atoms, a cyclic alkoxy group having 3 to 20 carbon atoms, a branched thioalkoxy group having 3 to 20 carbon atoms, a cyclic thioalkoxy group having 3 to 20 carbon atoms, a silyl group, or a ketone group having 1 to 20 carbon atoms. Alkoxycarbonyl groups having 2 to 20 carbon atoms, aryloxycarbonyl groups having 7 to 20 carbon atoms, alkenyl groups having 1 to 20 carbon atoms, -CN, carbamoyl, halocarbamoyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, -CF3, -Cl, -Br, -F, substituted or unsubstituted aromatic groups having 6 to 30 ring atoms, substituted or unsubstituted heteroaromatic groups having 5 to 30 ring atoms, substituted or unsubstituted aryloxy groups having 6 to 30 ring atoms, substituted or unsubstituted heteroaromatic groups having 5 to 30 ring atoms;

[0090] n0, n1, n2, and n5 are each independently selected from 0 to 11;

[0091] 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; when n5 is greater than or equal to 2, two adjacent R5s may or may not form a cycle.

[0092] This invention improves material properties, increases the luminous efficiency of light-emitting elements, and extends the luminous lifetime of light-emitting elements by introducing groups into boron-nitrogen compounds that increase the overall conjugation of the compounds.

[0093] In some embodiments, the organic compound has a structure as shown in any of general formulas (2-1) to (2-18):

[0094]

[0095]

[0096] Wherein, any one of R3 or R4 is independently selected from: -H, -D, a straight-chain alkyl group having 1 to 20 carbon atoms, a straight-chain alkoxy group having 1 to 20 carbon atoms, a straight-chain thioalkoxy group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, a cyclic alkyl group having 3 to 20 carbon atoms, a branched alkoxy group having 3 to 20 carbon atoms, a cyclic alkoxy group having 3 to 20 carbon atoms, a branched thioalkoxy group having 3 to 20 carbon atoms, a cyclic thioalkoxy group having 3 to 20 carbon atoms, a silyl group, a ketone group having 1 to 20 carbon atoms, Alkoxycarbonyl groups having 2 to 20 carbon atoms, aryloxycarbonyl groups having 7 to 20 carbon atoms, alkenyl groups having 1 to 20 carbon atoms, -CN, carbamoyl, halocarbamoyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, -CF3, -Cl, -Br, -F, substituted or unsubstituted aromatic groups having 6 to 30 ring atoms, substituted or unsubstituted heteroaromatic groups having 5 to 30 ring atoms, substituted or unsubstituted aryloxy groups having 6 to 30 ring atoms, substituted or unsubstituted heteroaromatic groups having 5 to 30 ring atoms;

[0097] n3 and n4 are each independently selected from 0 to 11;

[0098] When n3 is greater than or equal to 2, two adjacent R3s may form a cycle or not; when n4 is greater than or equal to 2, two adjacent R4s may form a cycle or not.

[0099] In some embodiments, Ph represents phenyl.

[0100] In the above embodiments, any R1, R2, R3, R4 or R5 is independently selected from -H, -D, straight-chain alkyl having 1 to 10 carbon atoms, branched alkyl having 3 to 10 carbon atoms, or cyclic alkyl having 3 to 10 carbon atoms.

[0101] Preferably, any one of R1, R2, R3, R4 or R5 is independently selected from: -H, -D, straight-chain alkyl having 1 to 4 carbon atoms, or branched alkyl having 3 to 5 carbon atoms.

[0102] More preferably, at least one of the substituents in R1, R2, R3, R4 and R5 is selected from a straight-chain alkyl group having 1 to 4 carbon atoms or a branched alkyl group having 3 to 5 carbon atoms.

[0103] Introducing alkyl groups into the organic compound can improve its solubility in processes such as inkjet printing, thereby enhancing the product quality of light-emitting elements that utilize the organic compound.

[0104] 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.

[0105] 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.

[0106] 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.

[0107] In some embodiments, two adjacent R4 rings form a ring with each other; further, two adjacent R4 rings form a 6-membered aromatic ring or an aliphatic ring; even further, two adjacent R4 rings form a ring with each other to form a ring. In this context, * indicates a connection site.

[0108] In some embodiments, two adjacent R5 rings form a ring with each other; further, two adjacent R5 rings form a 6-membered aromatic ring or an aliphatic ring; even further, two adjacent R5 rings form a ring with each other to form a ring. In this context, * indicates a connection site.

[0109] In some embodiments, when the structure represented by formula (A-3) exists in Ar1, the structure represented by formula (A-3) is preferably:

[0110] This is beneficial for improving the luminous efficiency and lifespan of light-emitting elements using the organic compounds.

[0111] In some embodiments, when the structure represented by equation (B-2) exists in Ar2, the structure represented by equation (B-2) is preferably:

[0112] as well as At least one of the organic compounds can help improve the luminous efficiency and lifespan of light-emitting elements using the organic compounds.

[0113] In some embodiments, the organic compound is a blue luminescent material.

[0114] In some embodiments, the organic compound is selected from the following compounds:

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132] The boron-containing biphenyl organic compounds provided in this invention 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 light-emitting element using the organic compound. Simultaneously, the introduction of tetrahydronaphthalene and / or indane structures into the boron-nitrogen compound improves the solubility of the molecule in inkjet printing and other processes, facilitating compound purification and thus increasing the purity of the organic compound M. This further extends the luminous efficiency and lifespan of the light-emitting element using the organic compound.

[0133] Please see Figure 1 as well as Figure 2 The present invention also provides a light-emitting element, the light-emitting element comprising: a pair of electrodes, including 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 as described above. The first electrode 101 may be an anode, and the second electrode 102 may be a cathode.

[0134] In some embodiments, the light-emitting element can be an organic light-emitting diode, an organic photovoltaic cell, an organic light-emitting cell, an organic field-effect transistor, an organic light-emitting field-effect transistor, an organic laser, an organic spintronic device, an organic sensor, and an organic plasmon emitting diode, etc., preferably an organic light-emitting diode, an organic light-emitting cell, or an organic light-emitting field-effect transistor.

[0135] In some embodiments, the light-emitting element can be applied to various electronic devices, such as display panels, lighting devices, and light sources.

[0136] 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 selected from one or more 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 WO2011110277A1. The entire contents of these three patent documents are hereby incorporated herein by reference.

[0137] The luminescent object material is selected from singlet luminescent materials (fluorescent materials), triplet luminescent materials (phosphorescent materials), and TADF materials.

[0138] 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.

[0139] 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.

[0140] In some embodiments, the organic functional layer 103 may include multiple layers. When the organic functional layer 103 is multilayered, the organic functional layer 103 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, a light-emitting layer 107, an electron blocking layer 106, an electron injection layer 109, an electron transport layer 108, or a hole blocking layer.

[0141] In some embodiments, the light-emitting element may be a blue light-emitting element, a green light-emitting element, or a red light-emitting element, and 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.

[0142] The light-emitting element has an emission wavelength between 300 and 1000 nm; further, the light-emitting element has an emission wavelength between 350 and 900 nm; even further, the light-emitting element has an emission wavelength between 400 and 800 nm; and still further, the light-emitting element has an emission wavelength within the wavelength range of blue light.

[0143] 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 light-emitting elements; when the host material is a blue light host material, the host material is preferably an anthracene-based organic compound.

[0144] 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 light-emitting element.

[0145] In some embodiments, the anode is a hole-injecting electrode, 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 light-emitting element of the present invention.

[0146] In some embodiments, the cathode is an electron-injecting electrode, 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 serving 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 in organic electronic devices may be used as cathode materials for the devices of this invention, 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, and ITO. 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.

[0147] 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.

[0148] 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.

[0149] 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.

[0150] 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.

[0151] 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.

[0152] In some embodiments, the light-emitting element 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 light-emitting element 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.

[0153] In some embodiments, the light-emitting element may be a solution-based light-emitting element, that is, at least one of the organic functional layers is prepared by a printing method (e.g., inkjet printing).

[0154] 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-type extrusion coating, etc. Preferably, gravure printing, inkjet printing, and other similar processes are used.

[0155] The composition may be a solution or a suspension, and may include a dispersed phase and a dispersant. The dispersed phase is one or more of the organic compounds described above, and the dispersant is used to disperse the dispersed phase.

[0156] In the composition, the mass fraction of the organic compound as described above 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%.

[0157] 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.

[0158] 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.

[0159] 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.

[0160] 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.

[0161] 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.

[0162] 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.

[0163] 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.

[0164] 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.

[0165] 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.

[0166] 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.

[0167] The exemplary preparation methods of the organic compounds provided by the present invention are shown in the following exemplary embodiments 1 to 17.

[0168] Example 1

[0169] Organic compound M1 Synthesis

[0170] The synthetic route for organic compound M1 is as follows:

[0171]

[0172] The specific synthetic steps of organic compound M1 are as follows:

[0173] Synthesis of intermediates 1-3:

[0174] 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 7.22 mmol and a yield of 72.2%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 1-3 was: MS(ASAP) = 313.

[0175] Synthesis of intermediates 1-5:

[0176] Intermediate 1-3 (10 mmol), compound 1-4 (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 give intermediate 1-5 with a molar amount of 6.18 mmol and a yield of 61.8%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate 1-5 was: MS(ASAP) = 370.

[0177] Synthesis of intermediates 1-7:

[0178] Intermediate 1-5 (10 mmol), compound 1-6 (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 give intermediate 1-7 with a molar amount of 5.89 mmol and a yield of 58.9%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate 1-7 was: MS(ASAP) = 490.

[0179] Synthesis of intermediates 1-9:

[0180] Intermediates 1-7 (10 mmol) and 1-8 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 ml: 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 1-9 with a molar amount of 6.11 mmol, yield: 61.1%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate 1-9 was: MS(ASAP) = 672.

[0181] Synthesis of organic compound M1:

[0182] In a 250 ml three-necked flask, 10 mmol of intermediate 1-9 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 the reaction mixture was cooled to 0 °C, and 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 41.5%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound M1 was: MS(ASAP) = 646.

[0183] Example 2

[0184] Organic compound M2 Synthesis

[0185] The synthetic route for organic compound M2 is as follows:

[0186]

[0187] The specific synthetic steps of organic compound M2 are as follows:

[0188] Synthesis of intermediate 2-2:

[0189] Compound 2-1 (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 2-2 with a molar amount of 8.17 mmol and a yield of 81.7%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 2-2 was: MS(ASAP) = 425.

[0190] Synthesis of intermediates 2-4:

[0191] Intermediate 2-2 (10 mmol), compound 2-3 (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 2-4 with a molar amount of 5.91 mmol and a yield of 59.1%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate 2-4 was: MS(ASAP) = 538.

[0192] Synthesis of intermediates 2-5:

[0193] Intermediate 2-4 (10 mmol), compound 1-6 (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 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 2-5 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 2-5 was: MS(ASAP) = 658.

[0194] Synthesis of intermediates 2-6:

[0195] Intermediates 2-5 (10 mmol) and 1-8 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 ml: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 yielded intermediate 2-6 with a molar amount of 6.57 mmol, yield: 65.7%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results for intermediate 2-6: MS(ASAP) = 840.

[0196] Synthesis of organic compound M2:

[0197] In a 250 mL three-necked flask, 10 mmol of intermediate 2-6 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 the reaction mixture was cooled to 0 °C, and 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 30.8%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound M2 was: MS(ASAP) = 814.

[0198] Example 3

[0199] Organic compound M3 Synthesis

[0200] The synthetic route for organic compound M3 is as follows:

[0201]

[0202] The specific synthetic steps of organic compound M3 are as follows:

[0203] Synthesis of intermediate 3-2:

[0204] Intermediate 2-4 (10 mmol), compound 3-1 (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 3-2 with a molar amount of 5.86 mmol and a yield of 58.6%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate 3-2 was: MS(ASAP) = 714.

[0205] Synthesis of intermediates 3-4:

[0206] Intermediate 3-2 (10 mmol) and intermediate 3-3 (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, separation, organic phase column chromatography, and recrystallization to obtain intermediate 3-4 with a molar amount of 5.41 mmol, yield: 54.1%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate 3-4 was: MS(ASAP) = 836.

[0207] Synthesis of organic compound M3:

[0208] In a 250 mL three-necked flask, 10 mmol of intermediate 3-4 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 the reaction mixture was 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 37.8%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound M3 was: MS(ASAP) = 810.

[0209] Example 4

[0210] Organic compound M4 Synthesis

[0211] The synthetic route for organic compound M4 is as follows:

[0212]

[0213] The specific synthetic steps of organic compound M4 are as follows:

[0214] Synthesis of intermediate 4-2:

[0215] Intermediate 3-2 (10 mmol) and intermediate 4-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 ml: 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 subjected to organic phase column chromatography and recrystallization to obtain intermediate 4-2 with a molar amount of 6.23 mmol and a yield of 62.3%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate 4-2 was MS(ASAP) = 836.

[0216] Synthesis of organic compound M4:

[0217] In a 250 mL three-necked flask, 10 mmol of intermediate 4-2 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 M4, with a yield of 42.9%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound M4 was: MS(ASAP) = 810.

[0218] Example 5

[0219] Organic compound M5 Synthesis

[0220] The synthetic route for organic compound M5 is as follows:

[0221]

[0222] The specific synthetic steps of organic compound M5 are as follows:

[0223] Synthesis of intermediate 5-2:

[0224] Compound 5-1 (10 mmol), compound 2-3 (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 5-2 with a molar amount of 8.09 mmol and a yield of 80.9%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 5-2 was: MS(ASAP) = 337.

[0225] Synthesis of intermediate 5-3:

[0226] Compound 5-2 (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 5-3 with a molar amount of 7.13 mmol and a yield of 71.3%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 5-3 was: MS(ASAP) = 481.

[0227] Synthesis of intermediate 5-5:

[0228] Intermediate 5-3 (10 mmol), compound 5-4 (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 5-5 with a molar amount of 5.29 mmol and a yield of 52.9%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 5-5 was: MS(ASAP) = 594.

[0229] Synthesis of intermediates 5-7:

[0230] Intermediate 5-5 (10 mmol), compound 5-6 (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 give intermediate 5-7 with a molar amount of 5.28 mmol and a yield of 52.8%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 5-7 was: MS(ASAP) = 714.

[0231] Synthesis of intermediates 5-8:

[0232] Intermediates 5-7 (10 mmol) and 1-8 (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 subjected to organic phase column chromatography and recrystallization to obtain intermediate 5-8 with a molar amount of 6.35 mmol and a yield of 63.5%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate 5-8 was MS(ASAP) = 896.

[0233] Synthesis of organic compound M5:

[0234] In a 250 ml three-necked flask, 10 mmol of intermediate 5-8 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 M5, with a yield of 28.4%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound M5 was: MS(ASAP) = 870.

[0235] Example 6

[0236] Organic compound M6 Synthesis

[0237] The synthetic route for organic compound M6 is as follows:

[0238]

[0239] The specific synthetic steps of organic compound M6 are as follows:

[0240] Synthesis of intermediate 6-2:

[0241] Compound 6-1 (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 6-2 with a molar amount of 8.54 mmol and a yield of 85.4%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate 6-2 was: MS(ASAP) = 225.

[0242] Synthesis of intermediate 6-3:

[0243] Compound 6-2 (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 6-3 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 6-3 was: MS(ASAP) = 369.

[0244] Synthesis of intermediate 6-4:

[0245] Intermediate 6-3 (10 mmol), compound 1-4 (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 give intermediate 6-4 with a molar amount of 5.33 mmol and a yield of 53.3%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate 6-4 was: MS(ASAP) = 426.

[0246] Synthesis of intermediate 6-5:

[0247] Intermediate 6-4 (10 mmol), compound 1-6 (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 give intermediate 6-5 with a molar amount of 6.48 mmol and a yield of 64.8%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate 6-5 was: MS(ASAP) = 546.

[0248] Synthesis of intermediates 6-7:

[0249] Intermediate 6-5 (10 mmol) and intermediate 6-6 (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 6-7 with a molar amount of 6.28 mmol, yield: 62.8%. Atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate 6-7: MS(ASAP) = 681.

[0250] Synthesis of organic compound M6:

[0251] In a 250 mL three-necked flask, 10 mmol of intermediate 6-7 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 M6, with a yield of 44.8%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound M6 was: MS(ASAP) = 655.

[0252] Example 7

[0253] Organic compound M7 Synthesis

[0254] The synthetic route for organic compound M7 is as follows:

[0255]

[0256] The specific synthetic steps of organic compound M7 are as follows:

[0257] Synthesis of intermediate 7-2:

[0258] Intermediates 6-5 (10 mmol) and 7-1 (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, 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 7-2 with a molar amount of 6.59 mmol, yield: 65.9%. Atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) results: MS(ASAP) = 684.

[0259] Synthesis of organic compound M7: 10 mmol of intermediate 7-2 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and a hexane solution of 21 mmol of t-BuLi (tert-butyllithium) was added dropwise. The temperature was raised to 60 °C and the reaction was carried out for 2 hours. The hexane solvent was 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 N,N-diisocyanate was added. Propylethylamine 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 M7, with a yield of 33.5%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound M7 was: MS(ASAP) = 658.

[0260] Example 8

[0261] Organic compound M8 Synthesis

[0262] The synthetic route for organic compound M8 is as follows:

[0263]

[0264] The specific synthetic steps of organic compound M8 are as follows:

[0265] Synthesis of intermediate 8-2:

[0266] Intermediates 1-7 (10 mmol) and 8-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 ml: 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, separation, organic phase column chromatography, and recrystallization to obtain intermediate 8-2 with a molar amount of 7.25 mmol and a yield of 72.5%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate 8-2 was MS(ASAP) = 672.

[0267] Synthesis of organic compound M8:

[0268] In a 250 mL three-necked flask, 10 mmol of intermediate 8-2 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 the reaction mixture was cooled to 0 °C, and 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 M8, with a yield of 29.4%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound M8 was: MS(ASAP) = 646.

[0269] Example 9

[0270] Organic compound M9 Synthesis

[0271] The synthetic route for organic compound M9 is as follows:

[0272]

[0273] The specific synthetic steps of organic compound M9 are as follows:

[0274] Synthesis of intermediate 9-1:

[0275] Compounds 1-5 (10 mmol), 5-6 (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 9-1 with a molar amount of 6.47 mmol and a yield of 64.7%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 9-1 was: MS(ASAP) = 490.

[0276] Synthesis of intermediate 9-3:

[0277] Intermediate 9-1 (10 mmol) and intermediate 9-2 (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, washing with water, separation, organic phase column chromatography, and recrystallization to obtain intermediate 9-3 with a molar amount of 5.73 mmol and a yield of 57.3%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate 9-3 was MS(ASAP) = 576.

[0278] Synthesis of organic compound M9: 10 mmol of intermediate 9-3 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask. Under a N2 atmosphere, the mixture was cooled to -30 °C, and a hexane solution of 21 mmol of t-BuLi (tert-butyllithium) was added dropwise. The temperature was raised to 60 °C and the reaction was carried out for 2 hours. The hexane solvent was 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 N,N-diisocyanate was added. Propylethylamine 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 M9, with a yield of 30.9%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound M9 was: MS(ASAP) = 550.

[0279] Example 10

[0280] Organic compound M10 Synthesis

[0281] The synthetic route for organic compound M10 is as follows:

[0282]

[0283] The specific synthetic steps of organic compound M10 are as follows:

[0284] Synthesis of intermediate 10-2:

[0285] Intermediate 9-1 (10 mmol) and intermediate 10-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 ml: 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 10-2 with a molar amount of 5.27 mmol, yield: 52.7%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate 10-2 was: MS(ASAP) = 562.

[0286] Synthesis of organic compound M10:

[0287] In a 250 mL three-necked flask, 10 mmol of intermediate 10⁻² 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 M10, with a yield of 35.5%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound M10 was: MS(ASAP) = 536.

[0288] Example 11

[0289] Organic compound M11 Synthesis

[0290] The synthetic route for organic compound M11 is as follows:

[0291]

[0292] The specific synthetic steps of organic compound M11 are as follows:

[0293] Synthesis of intermediate 11-2:

[0294] Compound 11-1 (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 11-2 with a molar amount of 7.43 mmol and a yield of 74.3%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 11-2 was: MS(ASAP) = 453.

[0295] Synthesis of intermediate 11-4:

[0296] Intermediate 11-2 (10 mmol), compound 11-3 (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 11-4 with a molar amount of 5.37 mmol and a yield of 53.7%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate 11-4 was: MS(ASAP) = 580.

[0297] Synthesis of intermediate 11-6:

[0298] Intermediate 11-4 (10 mmol), compound 11-5 (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 give intermediate 11-6 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 11-6 was: MS(ASAP) = 770.

[0299] Synthesis of intermediate 11-7:

[0300] Intermediates 11-6 (10 mmol) and 7-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 ml: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 yielded intermediate 11-7 with a molar amount of 6.28 mmol, yield: 62.8%. Atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result for intermediate 11-7: MS(ASAP) = 908.

[0301] Synthesis of organic compound M11:

[0302] In a 250 mL three-necked flask, 10 mmol of intermediate 11-7 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 M11, with a yield of 36.9%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound M11 was: MS(ASAP) = 882.

[0303] Example 12

[0304] Organic compound M12 Synthesis

[0305] The synthetic route for organic compound M12 is as follows:

[0306]

[0307] The specific synthetic steps of organic compound M12 are as follows:

[0308] Synthesis of intermediate 12-2:

[0309] Intermediate 11-6 (10 mmol) and intermediate 12-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 ml: 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 12-2 with a molar amount of 7.15 mmol and a yield of 71.5%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 12-2 was MS(ASAP) = 908.

[0310] Synthesis of organic compound M12:

[0311] In a 250 mL three-necked flask, 10 mmol of intermediate 12-2 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 M12, with a yield of 40.8%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound M12 was: MS(ASAP) = 882.

[0312] Example 13

[0313] Organic compound M13 Synthesis

[0314] The synthetic route for organic compound M13 is as follows:

[0315]

[0316] The specific synthetic steps of organic compound M13 are as follows:

[0317] Synthesis of intermediate 13-1:

[0318] Intermediate 3-2 (10 mmol) and intermediate 1-8 (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 13-1 with a molar amount of 7.55 mmol and a yield of 75.5%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 13-1 was MS(ASAP) = 896.

[0319] Synthesis of organic compound M13:

[0320] In a 250 mL three-necked flask, 10 mmol of intermediate 13-1 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 used 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 M13, with a yield of 31.4%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result for organic compound M13 was: MS(ASAP) = 870. Please refer to [link to relevant documentation]. Figure 3 The 1H NMR spectrum of organic compound M13 also indicates its formation.

[0321] Example 14

[0322] Organic compound M14 Synthesis

[0323] The synthetic route for organic compound M14 is as follows:

[0324]

[0325] The specific synthetic steps of organic compound M14 are as follows:

[0326] Synthesis of intermediate 14-3:

[0327] Intermediate 14-1 (10 mmol) and intermediate 14-2 (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 14-3 with a molar amount of 7.32 mmol and a yield of 73.2%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of intermediate 14-3 was MS(ASAP) = 273.

[0328] Synthesis of intermediate 14-5:

[0329] Compound 14-3 (10 mmol), compound 14-4 (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 14-5 with a molar amount of 7.17 mmol and a yield of 71.7%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 14-5 was: MS(ASAP) = 363.

[0330] Synthesis of intermediate 14-7:

[0331] Compounds 14-5 (10 mmol), 14-6 (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 14-7 with a molar amount of 6.58 mmol and a yield of 65.8%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 14-7 was: MS(ASAP) = 595.

[0332] Synthesis of intermediate 14-9:

[0333] Compound 14-7 (10 mmol), compound 14-8 (20 mmol), Pd(dba)2 (bis(dibenzylacetone)palladium, 0.2 mmol), TTBP (tri-tert-butylphosphine, 0.4 mmol), and sodium tert-butoxide (60 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 14-9 with a molar amount of 5.47 mmol and a yield of 54.7%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 14-9 was: MS(ASAP) = 829.

[0334] Synthesis of organic compound M14:

[0335] Prepare a dry 100 mL Schlenk flask, set up the reaction apparatus, evacuate, and purge with nitrogen. Keep nitrogen flowing in the reaction flask, add 10 mmol of intermediate 14-9 and 20 mL of toluene, evacuate and purge with nitrogen three times, and heat to 120 °C. Slowly add 20 mmol of boron triiodide to the reaction flask, tighten the cap, and react for 12 h. Extract with DCM, evaporate the solvent, and then use column chromatography (eluent: PE) to obtain a yellow-green solid, namely organic compound M14, with a yield of 45.9%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound M14 is: MS(ASAP) = 837.

[0336] Example 15

[0337] Organic compound M15 Synthesis

[0338] The synthetic route for organic compound M15 is as follows:

[0339]

[0340] The specific synthetic steps of organic compound M15 are as follows:

[0341] Synthesis of intermediate 15-3:

[0342] Intermediate 15-1 (10 mmol) and intermediate 15-2 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 ml: 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 15-3 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 15-3 was MS(ASAP) = 375.

[0343] Synthesis of intermediate 15-5:

[0344] Compound 15-3 (10 mmol), compound 15-4 (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 15-5 with a molar amount of 7.03 mmol and a yield of 70.3%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 15-5 was: MS(ASAP) = 521.

[0345] Synthesis of intermediate 15-6:

[0346] Compound 15-5 (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 15-6 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 15-6 was: MS(ASAP) = 665.

[0347] Synthesis of intermediate 15-8:

[0348] Compound 15-6 (10 mmol), compound 15-7 (10 mmol), Pd(dba)2 (bis(dibenzylacetone)palladium, 0.2 mmol), TTBP (tri-tert-butylphosphine, 0.4 mmol), and sodium tert-butoxide (60 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 15-8 with a molar amount of 5.03 mmol and a yield of 50.3%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 15-8 was: MS(ASAP) = 834.

[0349] Synthesis of intermediate 15-9:

[0350] Compound 15-8 (10 mmol), compound 15-4 (10 mmol), Pd(dba)2 (bis(dibenzylacetone)palladium, 0.2 mmol), TTBP (tri-tert-butylphosphine, 0.4 mmol), and sodium tert-butoxide (60 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 15-9 with a molar amount of 4.89 mmol and a yield of 48.9%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 15-9 was: MS(ASAP) = 980.

[0351] Synthesis of organic compound M15:

[0352] In a 250 ml three-necked flask, 10 mmol of intermediate 15-9 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 M15, with a yield of 33.7%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound M15 was: MS(ASAP) = 954.

[0353] Example 16

[0354] Organic compound M16 Synthesis

[0355] The synthetic route for organic compound M16 is as follows:

[0356]

[0357] The specific synthetic steps of organic compound M16 are as follows:

[0358] Synthesis of intermediate 16-2:

[0359] Compound 15-6 (10 mmol), compound 16-1 (10 mmol), Pd(dba)2 (bis(dibenzylacetone)palladium, 0.2 mmol), TTBP (tri-tert-butylphosphine, 0.4 mmol), and sodium tert-butoxide (60 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 16-2 with a molar amount of 6.27 mmol and a yield of 62.7%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 16-2 was: MS(ASAP) = 792.

[0360] Synthesis of intermediate 16-3:

[0361] Compound 16-2 (10 mmol), compound 15-4 (10 mmol), Pd(dba)2 (bis(dibenzylacetone)palladium, 0.2 mmol), TTBP (tri-tert-butylphosphine, 0.4 mmol), and sodium tert-butoxide (60 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 16-3 with a molar amount of 4.33 mmol and a yield of 43.3%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 16-3 was: MS(ASAP) = 938.

[0362] Synthesis of organic compound M16:

[0363] In a 250 mL three-necked flask, 10 mmol of intermediate 16-3 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 M16, with a yield of 38.9%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound M16 was: MS(ASAP) = 912.

[0364] Example 17

[0365] Organic compound M17 Synthesis

[0366] The synthetic route for organic compound M17 is as follows:

[0367]

[0368] The specific synthetic steps of organic compound M17 are as follows:

[0369] Synthesis of intermediate 17-2:

[0370] Compound 15-8 (10 mmol), compound 17-1 (10 mmol), Pd(dba)2 (bis(dibenzylacetone)palladium, 0.2 mmol), TTBP (tri-tert-butylphosphine, 0.4 mmol), and sodium tert-butoxide (60 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 17-2 with a molar amount of 5.78 mmol and a yield of 57.8%. The atmospheric pressure solid-phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 17-2 was: MS(ASAP) = 1022.

[0371] Synthesis of organic compound M17:

[0372] In a 250 mL three-necked flask, 10 mmol of intermediate 17-2 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 M17, with a yield of 41.5%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound M17 was: MS(ASAP) = 996.

[0373] Example 18

[0374] The boron-containing biphenyl organic compound M18 in this embodiment The synthetic route is as follows:

[0375]

[0376] Synthesis of intermediate 18-2:

[0377] Compound 15-6 (10 mmol), compound 18-1 (10 mmol), Pd(dba)2 (bis(dibenzylacetone)palladium, 0.2 mmol), TTBP (tri-tert-butylphosphine, 0.4 mmol), and sodium tert-butoxide (60 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 18-2 with a molar amount of 6.39 mmol, a yield of 63.9%, and MS (ASAP) = 772.

[0378] Synthesis of intermediate 18-3:

[0379] Compound 18-2 (10 mmol), compound 15-4 (10 mmol), Pd(dba)2 (bis(dibenzylacetone)palladium, 0.2 mmol), TTBP (tri-tert-butylphosphine, 0.4 mmol), and sodium tert-butoxide (60 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 18-3 with a molar amount of 5.26 mmol, a yield of 52.6%, and MS (ASAP) = 918.

[0380] Synthesis of organic compound M18: 10 mmol of intermediate 18-3 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and t-BuLi (tert-butyllithium, 21 mmol) n-hexane solution was added dropwise. The temperature was raised to 60 °C and the reaction was carried out for 2 hours. The n-hexane solvent was removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and 21 mmol of boron tribromide solution was added. The mixture was heated to room temperature and stirred for 0.5 hours. Finally, the reaction mixture was cooled to 0 °C. 42 mmol of N,N-diisopropylethylamine was added. After the addition was complete, the mixture was heated to room temperature and stirred. Then, the temperature was raised 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 M18, with a yield of 32.7% and MS (ASAP) = 892.

[0381] Example 19

[0382] Organic compound M19 in this embodiment The synthetic route is as follows:

[0383]

[0384] Synthesis of intermediate 19-2:

[0385] Compound 15-6 (10 mmol), compound 19-1 (10 mmol), Pd(dba)2 (bis(dibenzylacetone)palladium, 0.2 mmol), TTBP (tri-tert-butylphosphine, 0.4 mmol), and sodium tert-butoxide (60 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 19-2 with a molar amount of 7.59 mmol, a yield of 75.9%, and MS (ASAP) = 776.

[0386] Synthesis of intermediate 19-3:

[0387] Compound 19-2 (10 mmol), compound 15-4 (10 mmol), Pd(dba)2 (bis(dibenzylacetone)palladium, 0.2 mmol), TTBP (tri-tert-butylphosphine, 0.4 mmol), and sodium tert-butoxide (60 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 19-3 with a molar amount of 6.57 mmol, a yield of 65.7%, and MS (ASAP) = 922.

[0388] Synthesis of organic compound M19: 10 mmol of intermediate 19-3 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and t-BuLi (tert-butyllithium, 21 mmol) n-hexane solution was added dropwise. The temperature was raised to 60 °C and the reaction was carried out for 2 hours. The n-hexane solvent was removed by vacuum distillation. The reaction solution was cooled again to -30 °C, and 21 mmol of boron tribromide solution was added. The mixture was heated to room temperature and stirred for 0.5 hours. Finally, the reaction solution was cooled to 0 °C. 42 mmol of N,N-diisopropylethylamine was added. After the addition was complete, the mixture was heated to room temperature and stirred. Then, the temperature was raised 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 M19, with a yield of 45.3% and MS (ASAP) = 896.

[0389] Example 20

[0390] The organic compound M20 in this embodiment The synthetic route is as follows:

[0391]

[0392] Synthesis of intermediate 20-2:

[0393] Compound 15-6 (10 mmol), compound 20-1 (10 mmol), Pd(dba)2 (bis(dibenzylacetone)palladium, 0.2 mmol), TTBP (tri-tert-butylphosphine, 0.4 mmol), and sodium tert-butoxide (60 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 20-2 with a molar amount of 7.12 mmol, a yield of 71.2%, and MS (ASAP) = 762.

[0394] Synthesis of intermediate 20-3:

[0395] Compound 20-2 (10 mmol), compound 15-4 (10 mmol), Pd(dba)2 (bis(dibenzylacetone)palladium, 0.2 mmol), TTBP (tri-tert-butylphosphine, 0.4 mmol), and sodium tert-butoxide (60 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 20-3 with a molar amount of 5.48 mmol and a yield of 54.8%. MS (ASAP) = 908.

[0396] Synthesis of organic compound M20:

[0397] In a 250 mL three-necked flask, 10 mmol of intermediate 19-3 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and t-BuLi (tert-butyllithium, 21 mmol) n-hexane solution was added dropwise. The temperature was raised to 60 °C and the reaction was carried out for 2 hours. The n-hexane solvent was then removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and 21 mmol of boron tribromide solution was added. The mixture was then heated to room temperature and stirred for 0.5 hours. Finally, the reaction mixture was cooled to 0 °C, and 42 mmol of boron tribromide solution 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 47.9% and MS (ASAP) = 882.

[0398] Comparative Example 1

[0399] Comparative compound 1 was used as a comparative example in Examples 1 to 17 above. The structural formula of comparative compound 1 is as follows:

[0400]

[0401] As shown in Table 1, 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 M17 obtained in Examples 1 to 17 and comparative compound 1 in Comparative Example 1 can be obtained by quantum computing. 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 / SpinSinglet). 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 / SpinSinglet). The HOMO and LUMO levels are calculated according to the calibration formula below, while the S1 and T1 levels are used directly.

[0402] HOMO(eV)=((HOMO(G)×27.212)-0.9899) / 1.1206

[0403] LUMO(eV)=((LUMO(G)×27.212)-2.0041) / 1.385

[0404] Among them, HOMO, LUMO, T1 and S1 are direct calculation results of Gaussian09W, and the unit is Hartree.

[0405] Table 1: Calculation results of HOMO, LUMO, S1, and T1 energy levels for organic compounds M1 to M17 and comparative compound 1

[0406]

[0407]

[0408] As shown in Table 1, the T1 and S1 energy levels of organic compounds M1 to M20 provided in Examples 1 to 20 of the present invention are all higher than those of comparative compound 1. This indicates that, compared with comparative compound 1, the blue light emitted by organic compounds M1 to M20 is more biased towards deep blue, which is beneficial for obtaining better color coordinates for blue light-emitting elements using organic compounds M1 to M20 as guest materials in the light-emitting layer.

[0409] An exemplary manufacturing process for the light-emitting element provided by the present invention is shown in the following exemplary embodiment 21.

[0410] Example 21

[0411] In the light-emitting element provided in this embodiment, ITO (indium tin oxide) is used as the anode, and PEDOT (polyethylene dioxythiophene, Clevios) is used as the cathode. TM Al4083 was used as the material for the hole injection layer, PVK (Sigma Aldrich, average Mn 25,000-50,000) was used as the material for the hole transport layer, BH-1 to BH-3 were used as the host materials in the light-emitting layer of the corresponding light-emitting element, organic compounds M1 to M20 in Examples 1 to 20 and comparative compound 1 in Comparative Example 1 were used as guest materials in the light-emitting layer of the corresponding light-emitting element, ET and Liq (lithium 8-hydroxyquinoline) were used as the materials for the electron transport layer, and Al was used as the cathode. The specific preparation steps are as follows:

[0412] a. Cleaning of ITO anode: Clean the ITO conductive glass with chloroform, acetone and / or isopropanol, and then perform ultraviolet ozone treatment.

[0413] b. Formation of the hole injection layer: Spin-coating the hole injection layer material PEDOT (polyethylene dioxythiophene, Clevios) onto the ITO anode. TM AI4083), and was treated on a hot plate at 180°C for 10 minutes, with a hole injection layer thickness of 40nm;

[0414] c. Formation of hole transport layer: Spin-coat a toluene solution of PVK (Sigma Aldrich, Mn25,000-50,000) with a concentration of 5 mg / ml onto the hole injection layer, and then treat it on a hot plate at 180°C for 60 minutes. The thickness of the hole transport layer is 20 nm.

[0415] d. Formation of the luminescent layer: In a nitrogen glove box, spin-coat the luminescent layer material onto the hole transport layer, and then treat it on a hot plate at 140°C for 10 minutes. The host material in the luminescent layer of different luminescent elements corresponds to BH-1, BH-2, or BH-3, respectively. The guest material in the luminescent layer of different luminescent elements corresponds to one of the organic compounds M1 to M20, respectively. The solvent is methyl benzoate solution. The mass ratio of host material to guest material is 95:5. The concentration of the luminescent layer material is 15 mg / ml. The thickness of the final luminescent layer is 40 nm.

[0416] e. Formation of the electron transport layer: In a vacuum chamber, above the luminescent layer, ET and Liq are placed in different evaporation units under high vacuum (1×10⁻⁶). -6 In a millibar environment, ET and Liq were co-deposited at a weight ratio of 50:50 to form an electron transport layer with a thickness of 20 nm.

[0417] f. Formation of cathode layer: Al is deposited on top of the electron transport layer to obtain an Al cathode with a thickness of 100 nm;

[0418] g. Packaging: The device is encapsulated in a nitrogen glove box using UV-cured resin.

[0419] Specifically, in this embodiment, light-emitting elements 1 to 21 and comparison elements 1 to 3 are obtained through the above steps. The guest materials used for light-emitting elements 1 to 20 are organic compounds M1 to M20, respectively, and the host material used for light-emitting elements 1 to 20 is BH-1; the guest materials used for light-emitting elements 21 to 22 are organic compounds M4 and M5, respectively, and the host material used for light-emitting elements 18 to 19 is BH-2; the guest materials used for light-emitting elements 23 to 24 are organic compounds M4 and M5, respectively, and the host material used for light-emitting elements 23 to 24 is BH-3; the guest material used for comparison elements 1 to 3 is comparison compound 1, and the host materials used for comparison elements 1 to 3 are BH-1, BH-2, and BH-3, respectively.

[0420] Specifically, the chemical structural formulas of BH-1, BH-2, BH-3, ET, and Liq are as follows:

[0421]

[0422] In this embodiment, the current-voltage (JV) characteristics of light-emitting elements 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]), and current density of 10 mA / cm² were obtained for each light-emitting element and contrast element. 2 The luminous efficacy (CE@1knits[cd / A]) and the time taken for the brightness to decrease from the initial brightness of 1knits to 90% of the initial brightness (LT90@1knits[h]) are shown in Table 2.

[0423] Table 2: Performance data of light-emitting elements 1 to 21 and contrast elements 1 to 3

[0424]

[0425]

[0426] As shown in Table 2, the light-emitting elements 1 to 24 obtained by using guest materials 1 to 20 in the light-emitting layer of the present invention have superior color coordinates compared with the contrast elements 1 to 3. Furthermore, the luminous efficiency of light-emitting elements 1 to 24 is all between 5.7 and 6.5 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 light-emitting elements 1 to 24 to decrease from an initial brightness of 1 knits to 90% of the initial brightness is all in the range of 129 to 170 hours, which is 30% to 70% higher than 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 light-emitting elements 1 to 24 have a significantly improved lifespan.

[0427] Meanwhile, compared with Comparative Example 1, the organic compounds M1 to M20 have better overall molecular solubility and are easier to purify by introducing benzene rings and aromatic rings, thereby improving the purity of the compounds and thus improving the efficiency and lifespan of the light-emitting elements made from them.

[0428] Furthermore, the luminous efficiencies of light-emitting elements 2, 3, 4, 5, 13, 14, 15, 16, and 17 are all in the range of 6.2 to 6.5 cd / A, and their lifetimes are all around 160 hours. This is because, compared with the guest materials in other light-emitting elements, the overall molecular conjugation is greater, and the number of solubilizing groups is more, which improves the solubility of the guest materials and further improves the luminous efficiency and lifetime of the light-emitting elements.

[0429] The light-emitting element disclosed in this invention improves material properties, increases luminous efficiency, and extends lifespan by using a boron-nitrogen compound and introducing groups into the boron-nitrogen compound to increase the overall conjugation of the compound.

[0430] The present invention also discloses a display panel, which includes any of the light-emitting elements described above.

[0431] The display panel further includes an array substrate located on one side of the light-emitting element, and an encapsulation layer located on the side of the light-emitting element away from the array substrate and covering the light-emitting element. The display panel also includes a polarizer layer located on the side of the encapsulation layer away from the light-emitting element, and a cover plate layer located on the side of the polarizer layer away from the light-emitting element. The polarizer layer can be replaced by a color filter layer, which may include multiple color resists and black matrices located on both sides of the color resists.

[0432] The display panel disclosed in this invention uses a boron-nitrogen compound-containing light-emitting element and introduces groups into the boron-nitrogen compound to increase the overall conjugation of the compound, thereby enhancing the conjugation effect of the material applied to the light-emitting element, improving material performance, increasing the luminous efficiency of the display panel, and extending the service life of the display panel.

[0433] This invention discloses an organic compound, a light-emitting element, and a display panel. The organic compound has a structure as shown in general formula (1): According to general formula (1), the present invention improves the material properties, increases the luminous efficiency of the light-emitting element and extends the service life of the light-emitting element by introducing groups into the boron nitrogen compound to make the compound more conjugated as a whole.

[0434] The organic compound, light-emitting element, and display panel provided in the embodiments of the present invention have been described in detail above. Specific examples have been used to illustrate the principles and implementation methods of the present invention. The description of the above embodiments is only for the purpose of helping to understand the method and core ideas of the present invention. At the same time, for those skilled in the art, there will be changes in the specific implementation methods and application scope based on the ideas of the present invention. Therefore, the content of this specification should not be construed as a limitation of the present invention.

Claims

1. An organic compound, characterized in that, The organic compound has a structure as shown in general formula (2-9): ； Where X is selected from S; n1, n2, n3, n4, and n5 are each independently selected from any integer from 0 to 11; Any R1, R2, R3, R4 or R5 is independently selected from -H, tert-butyl or tert-pentyl. When n3 is greater than or equal to 2, two adjacent R3s may form a ring or not. When two adjacent R3s form a ring, they may form a five-membered aliphatic ring, a six-membered aromatic ring or a six-membered aliphatic ring.

2. The organic compound according to claim 1, characterized in that, The organic compound is selected from the following compounds: 。 3. A light-emitting element, characterized in that, include: A pair of electrodes, including a first electrode and a second electrode; An organic functional layer 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 2.

4. The light-emitting element according to claim 3, characterized in that, The organic functional layer includes at least a light-emitting layer, which comprises a host material and a guest material. The guest material is one or more organic compounds as described in any one of claims 1 to 2, and the host material is selected from fused aromatic or heteroaromatic compounds.

5. A display panel, characterized in that, Includes the light-emitting element as described in claim 3 or 4.

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