Organic compound, organic light-emitting device and display panel

Abstract

The invention relates to an organic compound, an organic light-emitting device and a display panel, the structural formula of the organic compound is # imgabs0 #. When the organic compound provided by the invention is applied to the organic light-emitting device, the light-emitting efficiency of the device can be improved, and the service life of the device can be prolonged.

Description

Technical Field

[0001] The present application relates to the field of display, and in particular to an organic compound, an organic light-emitting device and a display panel. Background Art

[0002] Currently, organic electroluminescent elements, such as organic light-emitting diodes (OLEDs), typically have an anode, a cathode, and an organic layer located between the two. The organic material in the organic layer converts electrical energy into light energy, thereby achieving organic electroluminescence. To improve the luminous efficiency and service life of organic electroluminescent elements, the organic layer is often multi-layered, and the organic material in each layer is different. Specifically, the organic layer mainly includes a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. When a voltage is applied between the anode and cathode of the organic electroluminescent element, the anode injects holes into the organic layer, and the cathode injects electrons into the organic layer. The injected holes and electrons meet to form excitons, and when the excitons transition back to the ground state, light is emitted, thereby achieving the light emission of the organic electroluminescent element. Organic electroluminescent elements have the characteristics of autonomous luminescence, high brightness, high efficiency, low voltage drive, wide viewing angle, high contrast, and high response. Therefore, organic electroluminescent devices have broad application prospects.

[0003] In order to improve the luminous efficiency of organic electroluminescent elements, various luminescent material systems based on fluorescence and phosphorescence have been developed. Among them, organic electroluminescent elements using fluorescent materials have the characteristics of high reliability, but under electrical excitation, due to the branching ratio of the singlet excited state and the triplet excited state of the exciton is 1:3, the internal electroluminescent quantum efficiency will be limited to less than 25%, while organic electroluminescent elements using phosphorescent materials can achieve almost 100% internal electroluminescent quantum efficiency. However, phosphorescent materials usually use metal complexes containing iridium and platinum, the raw materials are expensive and the synthesis is complex, and phosphorescent organic electroluminescent elements will also produce an efficiency roll-off effect, that is, the luminous efficiency decreases rapidly with the increase of current or brightness, which limits its application under high brightness.

[0004] To overcome these issues, existing technologies typically employ various material combinations based on organic compounds, such as composite excited-state materials and thermally activated delayed fluorescence (TADF) materials, attempting to utilize reverse internal conversion to achieve high efficiencies comparable to those of phosphorescent organic electroluminescent devices. However, conventional organic compounds with TADF have limited performance improvements in terms of both efficiency and lifespan, making it difficult to improve the luminous efficiency and lifespan of organic electroluminescent devices using organic compounds with TADF. Summary of the Invention

[0005] Embodiments of the present application provide an organic compound, an organic light-emitting device, and a display panel. When the organic compound is applied to an organic light-emitting device, the luminous efficiency and service life of the device can be improved.

[0006] In order to achieve the above object, according to the first aspect of the present application, an organic compound is provided, the structural formula of the organic compound is shown in formula (1):

[0007]

[0008] wherein Ar1 and Ar2 are selected from the structure represented by any one of formula (B-1) to formula (B-16):

[0009]

[0010] W1 is selected from CR6R7, SiR6R7, O, S, S=O or SO2;

[0011] R1 to R7 are selected from H, D, an alkyl group having 1 to 20 carbon atoms, a silicon group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a thioalkoxy group having 1 to 20 carbon atoms, a silyl group, a trimethylsilyl group, a triphenylsilyl group, a keto group having 1 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, an aryloxycarbonyl group having 7 to 20 carbon atoms, an alkene group having 1 to 20 carbon atoms, CN , carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, CF3, Cl, Br, F, a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring atoms, and a substituted or unsubstituted heteroaryloxy group having 5 to 30 ring atoms;

[0012] n1 is any integer selected from 0 to 4;

[0013] n2 is any integer selected from 0 to 7;

[0014] n3 is any integer selected from 0 to 9;

[0015] n4 is selected from any integer between 0 and 11;

[0016] n5 is any integer selected from 0 to 10;

[0017] n6 is selected from any integer between 0 and 8;

[0018] n7 is any integer selected from 0 to 4;

[0019] n8 is any integer selected from 0 to 6;

[0020] n9 is any integer selected from 0 to 5;

[0021] n10 is any integer selected from 0 to 9.

[0022] In a second aspect of the present application, an organic light-emitting device is provided, comprising:

[0023] a first electrode;

[0024] a second electrode, disposed opposite to the first electrode;

[0025] The organic functional layer is provided between the first electrode and the second electrode, and the material of the organic functional layer includes at least one of the above-mentioned organic compounds.

[0026] In a third aspect of the present application, a display panel is provided, comprising the organic light-emitting device described above.

[0027] In the organic compound, organic light-emitting device and display panel of the present application, by introducing a double hexamembered spirofluorene and a steric hindering group that makes the overall conjugation of the organic compound greater into the boron nitrogen compound, the molecular planar structure of the organic compound can be increased, thereby enhancing the solubility of the organic compound in the solvent, making the organic compound easy to purify, thereby improving the purity of the organic compound and improving the material properties; when the organic compound is applied to the organic light-emitting device, it is beneficial to improve the luminous efficiency of the organic light-emitting device and help to extend the service life of the organic light-emitting device. At the same time, the absolute value of the highest occupied molecular orbital (HOMO) energy level, the absolute value of the lowest unoccupied molecular orbital (LUMO) energy level, the lowest triplet excited state (T1) energy level and the lowest singlet excited state (S1) energy level of the organic compound of the present application are all low, and the chemical stability is increased, so that when the organic compound is applied to the organic light-emitting device, the service life of the device can be further extended.

[0028] Other features and advantages of the present application will be described in detail in the subsequent detailed description. BRIEF DESCRIPTION OF THE DRAWINGS

[0029] To more clearly illustrate the technical solutions in the embodiments of the present application, the following briefly introduces the drawings required for describing the embodiments. Obviously, the drawings described below are only some embodiments of the present application. Those skilled in the art can also derive other drawings based on these drawings without inventive effort.

[0030] In order to more completely understand the present application and its beneficial effects, the following description will be given in conjunction with the accompanying drawings, wherein the same drawing numbers represent the same parts in the following description.

[0031] Figure 1 A schematic structural diagram of an organic light-emitting device provided in one embodiment of the present application;

[0032] Figure 2 A schematic structural diagram of an organic light-emitting device provided in another embodiment of the present application;

[0033] Figure 100, organic light-emitting device; 10, substrate; 20, first electrode; 30, hole injection layer; 40, hole transport layer; 50, electron blocking layer; 60, light-emitting layer; 70, electron transport layer; 80, electron injection layer; 90, second electrode. DETAILED DESCRIPTION

[0034] The technical solutions in the embodiments of the present application will be described clearly and completely below in conjunction with the drawings in the embodiments of the present application.

[0035] In this application, composition, printing ink and ink have the same meaning and can be used interchangeably.

[0036] In the present application, aromatic group, aromatic series and aromatic ring system have the same meaning and can be used interchangeably.

[0037] In the present application, heteroaromatic group, heteroaromatic group and heteroaromatic ring system have the same meaning and can be used interchangeably.

[0038] In the present application, "substituted" means that the hydrogen atom in the substituted group is replaced by a substituent. "Substituted or unsubstituted" means that the defined group may be substituted or not. When the defined group is substituted, it should be understood that it is optionally substituted by a group acceptable in the art, including but not limited to an alkyl group with 1 to 30 carbon atoms, a heterocyclic group with 3 to 20 ring atoms, an aryl group with 5 to 20 ring atoms, a heteroaryl group with 5 to 20 ring atoms, a silanyl group, a carbonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a carbamoyl group, a haloformyl group, a formyl group, -NRR', a cyano group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a trifluoromethyl group, a nitro group or a halogen group, and the above groups may also be further substituted by The domain can accept substituents; it is understandable that R and R' in -NRR' are substituted by groups acceptable in the art, including but not limited to H, alkyl groups with 1 to 6 carbon atoms, cycloalkyl groups with 3 to 8 ring atoms, heterocyclic groups with 3 to 8 ring atoms, aryl groups with 5 to 20 ring atoms or heteroaryl groups with 5 to 10 ring atoms, and the above groups can be further substituted by one or more of the following groups: alkyl groups with 1 to 6 carbon atoms, cycloalkyl groups with 3 to 8 ring atoms, heterocyclic groups with 3 to 8 ring atoms, halogen, hydroxyl, nitro or amino.

[0039] In this application, when the same substituent appears multiple times, it can be independently selected from different groups. 1 , then R 1 Can be independently selected from different groups. For example, when the 6 carbon atoms on the benzene ring are all 1 When bonding, the six R 1 They may be the same or different from each other. Also, the number of substituents satisfies the substitution rules, for example The o in represents the number of substituents, and o can be selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, The o in can be selected from 0, 1, 2, 3, 4, 5 or 6.

[0040] In this application, the "number of ring atoms" refers to the number of atoms in the atoms that constitute the ring itself of a structural compound (e.g., a monocyclic compound, a condensed ring compound, a cross-linked compound, a carbocyclic compound, a heterocyclic compound) formed by atoms bonded together to form a ring. When the ring is substituted with a substituent, the atoms contained in the substituent are not included in the ring atoms. The "number of ring atoms" described below is also the same unless otherwise specified. For example, the number of ring atoms of a benzene ring is 6, the number of ring atoms of a naphthalene ring is 10, and the number of ring atoms of a thienyl group is 5.

[0041] In the present application, an aromatic ring system or aromatic group refers to a hydrocarbon group containing at least one aromatic ring, including monocyclic groups and polycyclic ring systems. A heteroaromatic ring system or heteroaromatic group refers to a hydrocarbon group (containing heteroatoms) containing at least one heteroaromatic ring, including monocyclic groups and polycyclic ring systems. The heteroatoms are preferably selected from Si, N, P, O, S and / or Ge, particularly preferably from Si, N, P, O and / or S. These polycyclic rings can have two or more rings, in which two carbon atoms are shared by two adjacent rings, i.e., fused rings. At least one of these polycyclic ring species is aromatic or heteroaromatic. In the present application, an aromatic group or heteroaromatic group includes not only a system of aromatic or heteroaromatic groups, but also, wherein multiple aromatic or heteroaromatic groups may be interrupted by short non-aromatic units (<10% non-H atoms, preferably less than 5% non-H atoms, such as C, N or O atoms). Therefore, systems such as 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamine, and diaryl ether are also considered as aromatic groups in this application.

[0042] Specifically, examples of the aromatic group include benzene, naphthalene, anthracene, phenanthrene, perylene, tetracene, pyrene, benzopyrene, triphenylene, naphthracene, fluorene, and derivatives thereof.

[0043] Specifically, examples of heteroaromatic groups include furan, benzofuran, thiophene, benzothiophene, pyrrole, pyrazole, triazole, imidazole, oxazole, oxadiazole, thiazole, tetrazole, indole, carbazole, pyrroloimidazole, pyrrolopyrrole, thienopyrrole, thienothiophene, furopyrrole, furofuran, thienofuran, benzisoxazole, benzisothiazole, benzimidazole, pyridine, pyrazine, pyridazine, pyrimidine, triazine, quinoline, isoquinoline, o-naphthylidene, quinoxaline, phenanthridine, primary idine, quinazoline, quinazolinone and derivatives thereof.

[0044] In the present application, "alkyl" may refer to a linear, branched and / or cyclic alkyl group. The number of carbon atoms in the alkyl group may be 1 to 50, 1 to 30, 1 to 20, 1 to 10 or 1 to 6. Non-limiting examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, 3,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyl decyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexyleicosyl, 2-octyleicosyl, n-heneicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-nonacosyl, n-triacontyl, and the like.

[0045] In the present application, "alkoxy" may mean a linear, branched and / or cyclic alkoxy group.

[0046] In the present application, "thioalkoxy" may represent a linear, branched and / or thioalkoxy group.

[0047] In the present application, "*" connected to a single bond indicates a linking site or a fusion site.

[0048] In the present application, when a linking site is not specified in a group, it means that an optional linking site in the group can be used as the linking site.

[0049] In the present application, when no fusion site is specified in a group, it means that any fusion site in the group can be used as the fusion site, and preferably two or more sites in the ortho position in the group are fusion sites.

[0050] In the present application, the single bond to which the substituent is connected runs through the corresponding ring, indicating that the substituent can be connected to any position of the ring. For example, In the formula, R is connected to any substitutable position of the benzene ring. express Can be used with The benzene rings are optionally fused to form a ring, preferably adjacent C atoms on the benzene rings.

[0051] In this application, the lowest triplet excited state energy level ET1, the highest occupied molecular orbital (HOMO) energy level, and the lowest unoccupied molecular orbital (LUMO) energy level play a key role in the energy level structure of organic materials. The following is an introduction to the determination of these energy levels.

[0052] HOMO and LUMO energy levels can be measured using the photoelectric effect, such as XPS (X-ray photoelectron spectroscopy) and UPS (ultraviolet photoelectron spectroscopy), or cyclic voltammetry (CV). Recently, quantum chemical methods, such as density functional theory (DFT), have also become effective methods for calculating molecular orbital energy levels.

[0053] The triplet energy level ET1 of an organic material can be measured by low-temperature time-resolved luminescence spectroscopy or calculated by quantum simulation (e.g., time-dependent DFT). For example, it can be calculated using the commercial software Gaussian09W (Gaussian Inc.). For specific simulation methods, see WO2011141110 or the methods described in the Examples below.

[0054] It should be noted that the absolute values ​​of HOMO, LUMO, and ET1 depend on the measurement or calculation method used, and even different HOMO / LUMO values ​​can be given for the same method and different evaluation methods. Therefore, reasonable and meaningful comparisons should be made using the same measurement method and the same evaluation method. In the description of the embodiments of this application, the values ​​of HOMO, LUMO, and ET1 are obtained based on time-dependent DFT simulations, but this does not affect the application of other measurement or calculation methods.

[0055] Existing organic compounds containing TADF have the disadvantages of poor luminous efficiency and service life when used in organic light-emitting devices.

[0056] In order to solve the above technical problems, the first aspect of the embodiments of the present application provides an organic compound, the structural formula of the organic compound is shown in formula (1):

[0057]

[0058] wherein Ar1 and Ar2 are selected from the structure represented by any one of formula (B-1) to formula (B-16):

[0059]

[0060] W1 is selected from CR6R7, SiR6R7, O, S, S=O or SO2;

[0061] R1 to R7 are selected from H, D, an alkyl group having 1 to 20 carbon atoms, a silicon group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a thioalkoxy group having 1 to 20 carbon atoms, a silyl group, a trimethylsilyl group, a triphenylsilyl group, a keto group having 1 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, an aryloxycarbonyl group having 7 to 20 carbon atoms, an alkene group having 1 to 20 carbon atoms, CN , carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, CF3, Cl, Br, F, a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring atoms, and a substituted or unsubstituted heteroaryloxy group having 5 to 30 ring atoms;

[0062] n1 is any integer selected from 0 to 4;

[0063] n2 is any integer selected from 0 to 7;

[0064] n3 is any integer selected from 0 to 9;

[0065] n4 is selected from any integer between 0 and 11;

[0066] n5 is any integer selected from 0 to 10;

[0067] n6 is selected from any integer between 0 and 8;

[0068] n7 is any integer selected from 0 to 4;

[0069] n8 is any integer selected from 0 to 6;

[0070] n9 is any integer selected from 0 to 5;

[0071] n10 is any integer selected from 0 to 9.

[0072] In the embodiment of the present application, n1 can be 0, 1, 2, 3, 4; n2 can be 0, 1, 2, 3, 4, 5, 6, 7; n3 can be 0, 1, 2, 3, 4, 5, 6, 7, 8, 9; n4 can be 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11; n5 can be 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10; n6 can be 0, 1, 2, 3, 4, 5, 6, 7, 8; n7 can be 0, 1, 2, 3, 4; n8 can be 0, 1, 2, 3, 4, 5, 6; n9 can be 0, 1, 2, 3, 4, 5; n10 can be 0, 1, 2, 3, 4, 5, 6, 7, 8, 9.

[0073] In some embodiments, R1 to R4 are selected from one or more of H, D, and an alkyl group having 1 to 14 carbon atoms.

[0074] In some embodiments, R5 is selected from a combination of one or more of H, D, and an alkyl group having 1 to 10 carbon atoms.

[0075] By introducing an alkyl group into the organic compound, the solubility of the organic compound in processes such as inkjet printing is improved, and the product quality of the organic light-emitting device using the organic compound is improved.

[0076] In some embodiments, R5 is selected from any of the following structures:

[0077]

[0078] V is selected from CR8 or N;

[0079] W2 is selected from NR9, CR9R 10 、SiR9R 10 , O, S, S=O or SO2;

[0080] R8-R 10 a combination of one or more selected from H, D, an alkyl group having 1 to 20 C atoms, an alkoxy group having 1 to 20 C atoms, a thioalkoxy group having 1 to 20 C atoms, a silyl group, a keto group having 1 to 20 C atoms, an alkoxycarbonyl group having 2 to 20 C atoms, an aryloxycarbonyl group having 7 to 20 C atoms, a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, an amine group, CF3, Cl, Br, F, I, a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, a substituted or unsubstituted aryloxy group having 5 to 60 ring atoms, and a substituted or unsubstituted heteroaryloxy group having 5 to 60 ring atoms;

[0081] In some embodiments, Ar1 and Ar2 are selected from any of the following structures:

[0082]

[0083] R5 is selected from one or more combinations of H, D, trimethylsilyl group, benzene ring or F.

[0084] In some preferred embodiments, R5 is selected from one or both of D and trimethylsilyl groups.

[0085] The research team of this application discovered through experiments that by further introducing D and trimethylsilyl groups into the steric groups in the compound, the service life of the equipment will be further increased.

[0086] In some embodiments, the organic compound is any one of the following compounds:

[0087]

[0088]

[0089]

[0090]

[0091]

[0092] It is understood that the organic compounds of the embodiments of the present application can be selected from the above compounds but are not limited to the above compounds.

[0093] The organic compounds provided in the embodiments of the present application can be used as organic functional materials in the organic functional layer of electronic devices, in particular in the organic functional layer of OLED devices. The materials of the organic functional layer can be divided into hole injection materials (HIM), hole transport materials (HTM), electron transmission materials (ETM), electron injection materials (EIM), electron blocking materials (EBM), hole blocking materials (HBM), luminescent materials (EM), host materials and guest materials (such as organic dyes).

[0094] In some embodiments, the organic compound provided by the embodiments of the present application can be used as a light-emitting material in a light-emitting layer of a light-emitting device.

[0095] In a specific embodiment, the organic compound provided in the embodiments of the present application can be used as a guest material in the light-emitting layer of a light-emitting device.

[0096] Furthermore, the organic compound provided in the embodiments of the present application can be used as a green light guest material in the light-emitting layer of a light-emitting device.

[0097] In the organic compounds, organic light-emitting devices, and display panels of the present application, by introducing a double hexamethylene spirofluorene and a steric hindering group into the boron-nitrogen compound to increase the overall conjugation of the organic compound, the molecular planar structure of the organic compound can be increased, thereby enhancing the solubility of the organic compound in the solvent, making the organic compound easier to purify, thereby increasing the purity of the organic compound and improving the material properties; when the organic compound is used in an organic light-emitting device, it is beneficial to improve the luminous efficiency of the organic light-emitting device and help extend the service life of the organic light-emitting device. At the same time, the absolute value of the HOMO energy level, the absolute value of the LUMO energy level, the T1 energy level, and the S1 energy level of the organic compound of the present application are all low, and the chemical stability is increased, so that when the organic compound is used in an organic light-emitting device, the service life of the device can be further extended.

[0098] An embodiment of the present application also provides a mixture, which includes at least one of the above-mentioned organic compounds and an organic functional material, wherein the organic functional material is selected from a combination of one or more hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, luminescent materials, host materials or organic dyes.

[0099] In some embodiments, the organic functional material includes a host material.

[0100] In some embodiments, the organic functional material is selected from a combination of one or more of a hole injection material, a hole transport material, an electron transport material, a hole blocking material, a light-emitting host material, and an organic dye, and the mass ratio of the organic compound to the organic functional material is 1:99 to 1:2.3, preferably 1:99 to 1:9. For example, the mass ratio of the organic compound to the organic functional material is 1:99, 1:90, 1:85, 1:80, 1:75, 1:65, 1:50, 1:45, 1:40, 1:25, 1:19, 1:10, 1:5, or 1:2.3.

[0101] In some embodiments, the organic functional material is a light-emitting material, and the mass ratio of the organic compound to the organic functional material is 99:1 to 2.3:1. For example, the mass ratio of the organic compound to the organic functional material is 99:1, 90:1, 85:1, 80:1, 75:1, 65:1, 50:1, 45:1, 40:1, 25:1, 19:1, 10:1, 5:1, or 2.3:1.

[0102] In some embodiments, the organic functional material is a light-emitting material, and the mass ratio of the organic compound to the organic functional material is 99:1 to 9:1.

[0103] In some embodiments, the light-emitting material is selected from a singlet light emitter (fluorescent light emitter), a triplet light emitter (phosphorescent light emitter), and a TADF material.

[0104] In the examples of the present application, detailed descriptions of various organic functional materials are given in WO2010135519A1, US20090134784A1 and WO 2011110277A1, and the entire contents of these three patent documents are hereby incorporated herein by reference.

[0105] An embodiment of the present application also provides a composition, which includes at least one of the above-mentioned organic compounds or the above-mentioned mixture.

[0106] In the embodiments of the present application, the composition is a solution or a suspension.

[0107] In some embodiments, the composition includes a dispersant and a dispersant, the dispersant includes at least one of the above-mentioned organic compound or the above-mentioned mixture and a first organic solvent, and the dispersant is used to disperse the dispersant.

[0108] In some embodiments, the mass fraction of the organic compound in the composition is 0.3% to 30%. For example, the mass fraction of the organic compound is 0.3%, 0.5%, 0.8%, 1.0%, 1.5%, 3%, 5%, 10%, 12%, 15%, 18%, 20%, 23%, 25%, 28% or 30%.

[0109] In some embodiments, in the composition, the mass fraction of the above organic compound is preferably 0.5% to 20%, more preferably 0.5% to 15%, further preferably 0.5% to 10%, and most preferably 1% to 5%.

[0110] In the embodiments of the present application, the composition can be an ink for a printing process. The viscosity and surface tension of the ink are important parameters. The surface tension parameters of the appropriate ink are suitable for a specific substrate and a specific printing method. In some embodiments, the surface tension of the composition at operating temperature or at 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 advantageous for application in an inkjet printing process. In some embodiments, the viscosity of the composition at operating temperature or at 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 advantageous for application in an inkjet printing process.

[0111] 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 range is preferably 18.5 to 21.0 MPa 1 / 2 range; δp (polar force) is 0.2~12.5MPa 1 / 2 The range is preferably 2.0 to 6.0 MPa 1 / 2 range; δh (hydrogen bond force) is 0.9~14.2MPa 1 / 2 The range is preferably 2.0 to 6.0 MPa 1 / 2 range.

[0112] In some embodiments, the boiling point of the dispersant is greater than or equal to 150°C, preferably greater than or equal to 180°C, 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 dispersant with a boiling point of at least 150°C is beneficial for preventing nozzle clogging of the inkjet print head during inkjet printing, and a higher boiling point is more beneficial for preventing clogging.

[0113] In an embodiment of the present application, the dispersant includes a second organic solvent, and the second organic solvent can be evaporated from the solvent system to form a film containing a functional material. The second organic solvent can be selected from aromatic or heteroaromatic. Specifically, the second organic solvent can be selected from p-diisopropylbenzene, pentylbenzene, tetralin, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, dipentylbenzene, tripentylbenzene, pentyltoluene, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, 1,2,3,4-tetramethylbenzene, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, butylbenzene, dodecylbenzene, dihexylbenzene, dibutylbenzene, p-diisopropylbenzene, cyclohexylbenzene, benzylbutylbenzene, dimethylnaphthalene, 3-isopropylbiphenyl, Benzene, p-methylisopropylbenzene, 1-methylnaphthalene, 1,2,4-trichlorobenzene, 4,4-difluorodiphenylmethane, 1,2-dimethoxy-4-(1-propenyl)benzene, diphenylmethane, 2-phenylpyridine, 3-phenylpyridine, N-methyldiphenylamine, 4-isopropylbiphenyl, α,α-dichlorodiphenylmethane, 4-(3-phenylpropyl)pyridine, benzyl benzoate, 1,1-bis(3,4-dimethylphenyl)ethane, 2-isopropylnaphthalene, quinoline, isoquinoline, methyl 2-furoate, ethyl 2-furoate, etc.

[0114] The second organic solvent can also be selected from aromatic ketone solvents. Specifically, the second organic solvent can be selected from 1-tetralone, 2-tetralone, 2-(phenylepoxy)tetralone, 6-(methoxy)tetralone, acetophenone, propiophenone, benzophenone, and their derivatives, such as 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylpropiophenone, 3-methylpropiophenone, 2-methylpropiophenone, etc.

[0115] The second organic solvent can also be selected from aromatic ether solvents. Specifically, the second organic solvent can 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-ethyl acetate, 1,3-dipropoxybenzene, 1,2,4-trimethoxybenzene, 4-(1-propenyl)-1,2-dimethoxybenzene, 1,3-dimethoxybenzene, glycidyl phenyl ether, dibenzyl ether, 4-tert-butylanisole, trans-p-propenylanisole, 1,2-dimethoxybenzene, 1-methoxynaphthalene, diphenyl ether, 2-phenoxymethyl ether, 2-phenoxytetrahydrofuran, ethyl-2-naphthyl ether, etc.

[0116] The second organic solvent can also be selected from aliphatic ketones, such as 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2,5-hexanedione, 2,6,8-trimethyl-4-nonanone, fenchone, phorone, isophorone, di-n-amyl ketone, etc.; or aliphatic ethers, such as amyl ether, hexyl ether, dioctyl ether, ethylene glycol dibutyl ether, diethylene glycol diethyl ether, diethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, triethylene glycol ethyl methyl ether, triethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, etc.

[0117] The second organic solvent can also be selected from organic ester solvents. Specifically, the second organic 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.

[0118] The second organic solvent can also be selected from one or more solvents such as methanol, ethanol, 2-methoxyethanol, dichloromethane, chloroform, chlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1,4-dioxane, acetone, methyl ethyl ketone, 1,2-dichloroethane, 3-phenoxytoluene, 1,1,1-trichloroethane, 1,1,2,2-tetrachloroethane, ethyl acetate, butyl acetate, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, tetralin, decalin, and indene.

[0119] In addition to the dispersant and the dispersant, the composition may also include one or more components such as surfactants, lubricants, wetting agents, hydrophobic agents, adhesives, etc., for adjusting viscosity, film-forming properties, improving adhesion, etc.

[0120] See also Figures 1 and 2 The present invention also provides an organic light emitting device 100, which includes a first electrode 20 and a second electrode 90 disposed opposite to each other, and an organic functional layer disposed between the first electrode 20 and the second electrode 90. The material of the organic functional layer includes the above-mentioned organic compound or mixture, or the organic functional layer is prepared from the above-mentioned composition.

[0121] In the embodiment of the present application, the organic light-emitting device 100 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 emission diode, etc., preferably an organic light-emitting diode, an organic light-emitting cell, and an organic light-emitting field-effect transistor.

[0122] In the embodiment of the present application, the organic light-emitting device 100 can be applied to a variety of electronic devices, such as display panels, lighting equipment, light sources, etc.

[0123] It can be understood that the organic functional layer can be a single layer or multiple layers. When the organic functional layer is a single layer, it includes the above mixture.

[0124] In some embodiments, the organic functional layer includes a light emitting layer 60 .

[0125] In some embodiments, the organic functional layer further includes a hole injection layer 30 , a hole transport layer 40 , an electron blocking layer 50 , an electron injection layer 80 , an electron transport layer 70 or a hole blocking layer.

[0126] In some embodiments, the organic light-emitting device 100 is a green organic light-emitting device or a red organic light-emitting device.

[0127] In some embodiments, the light emitting wavelength of the organic light emitting device 100 is between 300 and 1000 nm; further, the light emitting wavelength of the organic light emitting device 100 is between 350 and 900 nm; further, the light emitting wavelength of the organic light emitting device 100 is between 400 and 800 nm; further, the light emitting wavelength of the organic light emitting device 100 is within the wavelength range of green light.

[0128] In some embodiments, the light emitting layer 60 includes a host material and a guest material, and the guest material includes at least one of the above-mentioned organic compounds.

[0129] In some embodiments, the organic compound is a green light-emitting material.

[0130] In some embodiments, the host material includes a combination of one or more of a fused aromatic derivative or a heteroaromatic compound.

[0131] In some embodiments, the host material includes at least one of anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, triazine derivatives, and pyrimidine derivatives. Preferably, the host material is a green light host material used in a green organic light-emitting device; when the host material is a green light host material, the host material is preferably an anthracene organic compound.

[0132] In some embodiments, the host material includes any one of the following compounds:

[0133]

[0134] In some embodiments, the mass ratio of the host material to the guest material is 99:1 to 2.3:1, 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 2.3:1, which helps to inhibit crystallization of the light-emitting layer and concentration quenching caused by high concentrations of the guest material, thereby improving the luminous efficiency of the organic light-emitting device 100.

[0135] In some embodiments, the first electrode 20 is an anode and the second electrode 90 is a cathode.

[0136] In some embodiments, the anode is a hole-injecting electrode, and the anode can inject holes into the organic functional layer, such as the anode injecting holes into the hole injection layer 30, the hole transport layer 40, or the light-emitting layer 60. The anode may include at least one of a conductive metal, a conductive metal oxide, and a conductive polymer. Preferably, the absolute value of the difference between the work function of the anode and the HOMO energy level or valence band energy level of the p-type semiconductor material serving as the hole injection layer, or the HOMO energy level or valence band energy level of the p-type semiconductor material in the hole injection layer and the 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), etc., or other suitable and known anode materials, which can be easily selected and used by those of ordinary skill in the art. The anode material can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), etc. In some embodiments, the anode can be patterned, such as patterned ITO conductive substrates that are commercially available and can be used to prepare the organic light-emitting device 100 of the present application.

[0137] In some embodiments, the cathode is an electrode that injects electrons, and the cathode can inject electrons into the organic functional layer, such as the cathode injecting electrons into the electron injection layer 80, the electron transport layer 70 or the light-emitting layer 60. The cathode includes 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 energy level or conduction band energy level of the n-type semiconductor material serving as the electron injection layer, and the LUMO energy level or conduction band energy level of the n-type semiconductor material of the electron injection layer and the electron transport layer or the hole blocking layer is less than 0.5 eV, preferably less than 0.3 eV, and more preferably less than 0.2 eV. All materials that can be used as cathodes of organic electronic devices may be used as cathode materials of the device of the present application, and the materials of the cathode include but are not limited to at least one of Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloy, BaF2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO, etc. The cathode material may be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), and the like.

[0138] In some embodiments, the hole injection layer 30 is used to promote the injection of holes from the anode into the light-emitting layer, and the hole injection layer 30 includes a hole injection material, which is a material that can receive holes injected from the positive electrode at a low voltage, and preferably, the HOMO is between the work function of the material of the anode and the HOMO of the functional material of the film layer away from the anode (such as the hole transport material of the hole transport layer). The hole injection material includes but is not limited to at least one of metalloporphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, perylene-based organic material, anthraquinone, polyaniline-based and polythiophene-based conductive polymers, etc.

[0139] In some embodiments, the hole transport layer 40 can be used to transport holes to the light-emitting layer 60. The hole transport layer 40 includes a hole transport material that receives holes transported from the anode or the hole injection layer 30 and transfers the holes to the light-emitting layer 60. The hole transport material is a material known in the art having high hole mobility, and the hole transport material may include, but is not limited to, at least one of an arylamine-based organic material, a conductive polymer, a block copolymer having both a conjugated portion and a non-conjugated portion, and the like.

[0140] In some embodiments, the electron transport layer 70 is used to transport electrons. The electron transport layer 70 includes an electron transport material. The electron transport material receives electrons injected from the negative electrode and transfers the electrons to the light-emitting layer 60. The electron transport material is a material known in the art having high electron mobility. The electron transport material may include, but is not limited to, at least one of an Al complex of 8-hydroxyquinoline, a complex containing Alq3, an organic free radical compound, a hydroxyflavone-metal complex, 8-hydroxyquinoline lithium (LiQ), and a benzimidazole-based compound.

[0141] In some embodiments, the electron injection layer 80 is used to inject electrons. The electron injection layer 80 includes an electron injection material. The electron injection material preferably has the ability to transport electrons, has the effect of injecting electrons from the negative electrode, has an excellent effect of injecting electrons into the light-emitting layer or the light-emitting material, and has the ability to prevent excitons generated by the light-emitting layer 60 from moving to the hole injection layer 30, and also has an excellent ability to form a thin film. The electron injection material includes, but is not limited to, at least one of 8-hydroxyquinoline lithium (LiQ), fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, pyrazole, diazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenyl methane, anthrone, and derivatives thereof, metal complex compounds, and nitrogen-containing five-membered ring derivatives.

[0142] In some embodiments, the hole blocking layer is used to block holes from reaching the negative electrode and can generally be formed under the same conditions as the hole injection layer. The hole blocking layer includes a hole blocking material, which includes but is not limited to at least one of a diazole derivative or a triazole derivative, a phenanthroline derivative, BCP, an aluminum complex, and the like.

[0143] In some embodiments, see Figure 1 The organic light-emitting device 100 includes a substrate 10, a first electrode 20, a hole injection layer 30, a hole transport layer 40, an electron blocking layer 50, a light-emitting layer 60, an electron transport layer 70, an electron injection layer 80 and a second electrode 90, which are stacked in sequence.

[0144] In some embodiments, see Figure 2 The organic light-emitting device 100 includes a substrate 10, a first electrode 20, a hole injection layer 30, a hole transport layer 40, a light-emitting layer 60, an electron transport layer 70 and a second electrode 90 which are stacked in sequence.

[0145] In the embodiment of the present application, the substrate 10 may be a transparent substrate or an opaque substrate. When the substrate 10 is a transparent substrate, a transparent organic light-emitting device 100 may be manufactured. The substrate 10 may be a rigid substrate or a flexible substrate with elasticity. The material of the substrate 10 may include but is not limited to plastic, polymer, metal, semiconductor wafer or glass. Preferably, the substrate 10 includes at least one smooth surface for forming the anode on the surface. More preferably, the surface has no surface defects. Preferably, the material of the substrate 10 is a 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.

[0146] In the embodiment of the present application, the organic light-emitting device 100 may be a solution-type organic light-emitting device, that is, at least one of the organic functional layers is prepared by printing (eg, inkjet printing).

[0147] The organic light-emitting device of the present application comprises an organic compound represented by the general formula (1). The organic compound represented by the general formula (1) can increase the molecular planar structure of the organic compound by introducing a double hexagonal spirofluorene and a steric hindering group into a boron-nitrogen compound, thereby enhancing the solubility of the organic compound in a solvent, making the organic compound easier to purify, thereby increasing the purity of the organic compound and improving material properties. When the organic compound is used in an organic light-emitting device, it is beneficial to improve the luminous efficiency of the organic light-emitting device and help extend the service life of the organic light-emitting device. At the same time, the absolute value of the HOMO energy level, the absolute value of the LUMO energy level, the T1 energy level, and the S1 energy level of the organic compound represented by the general formula (1) are all low, and the chemical stability is increased, so that when the organic compound is used in an organic light-emitting device, the service life of the device can be further extended.

[0148] Moreover, the inventors discovered that when the invention is applied to organic light-emitting devices, the color coordinates are further optimized, which can further deepen the green light color, and is very beneficial for its later application in high-end displays.

[0149] An embodiment of the present application further provides a display panel, which includes the above-mentioned organic light-emitting device.

[0150] In some embodiments, the display panel further includes an array substrate located on one side of the organic light-emitting device and an encapsulation layer located on a side of the organic light-emitting device 100 away from the array substrate and covering the organic light-emitting device.

[0151] In some embodiments, the display panel further includes a polarizer layer located on the side of the encapsulation layer away from the organic light-emitting device, and a cover layer located on the side of the polarizer layer away from the organic light-emitting device. The polarizer layer can be replaced with a color filter layer, which can include multiple color resists and a black matrix located on both sides of the color resists.

[0152] It is understandable that the embodiments of the present application may further include other components, and the types and specific structures of the other components are not limited.

[0153] The display panel provided by the present application has the above-mentioned organic light-emitting device. The organic compound represented by the general formula (1) can increase the molecular planar structure of the organic compound by introducing a double hexagonal spirofluorene and a steric hindering group into the boron nitrogen compound to increase the overall conjugation of the organic compound, thereby enhancing the solubility of the organic compound in the solvent, making the organic compound easy to purify, thereby improving the purity of the organic compound and improving the material properties; when the organic compound is applied to the organic light-emitting device, it is beneficial to improve the luminous efficiency of the organic light-emitting device and help to extend the service life of the organic light-emitting device. At the same time, the absolute value of the HOMO energy level, the absolute value of the LUMO) energy level, the T1 energy level and the S1 energy level of the organic compound represented by the general formula (1) are all low, and the chemical stability is increased, so that when the organic compound is applied to the organic light-emitting device, the service life of the device can be further extended, thereby improving the display effect and service life of the display panel. Since the color coordinates of the organic light-emitting device are further optimized, the green light color can be further deepened, which is very beneficial for the later display panel to be applied to high-end displays.

[0154] The present application will be described below in conjunction with preferred embodiments, but the present application is not limited to the following embodiments. It should be understood that the attached claims summarize the scope of the present application. Under the guidance of the inventive concept of the present application, those skilled in the art should realize that certain changes made to the various embodiments of the present application will be covered by the spirit and scope of the claims of the present application. Specific embodiments

[0156] (1) Synthesis of organic compounds

[0157] Example 1 Synthesis of Organic Compound M1

[0158] The synthetic route of organic compound M1 is as follows:

[0159]

[0160] Synthesis of intermediate 1-3:

[0161] Compound 1-1 (10 mmol), compound 1-2 (20 mmol), and cesium carbonate (100 mmol) were dissolved in DMF, heated to 140° C. under a nitrogen atmosphere, and stirred for 6 h. After the reaction solution was cooled, the solvent was removed by rotary evaporation, and the mixture was extracted and washed with water. The organic phase was subjected to column chromatography to obtain intermediate 1-3. The molar weight of intermediate 1-3 was 8.37 mmol, and the yield was 83.7%. The atmospheric pressure solid phase analytical probe mass spectrometry (ASAP-MS) result of intermediate 1-3 was: MS (ASAP) = 788.

[0162] Synthesis of intermediate 1-6:

[0163] Compound 1-4 (10 mmol) and compound 1-5 (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; under a nitrogen atmosphere, the mixture was heated to 100°C and stirred for 6 h; after the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the mixture was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 1-6. The molar weight of intermediate 1-6 was 7.17 mmol, the yield was 71.7%, and MS (ASAP) = 261.

[0164] Synthesis of intermediate 1-7:

[0165] In a two-necked flask, under nitrogen atmosphere, the intermediate 1-3 (10 mmol) was dissolved in 20 ml of dry tetrahydrofuran, cooled to -78 ° C, and a pentane solution of n-butyl lithium (1M, 12 ml) was added and reacted at this temperature for 1 hour; the intermediate 1-6 (20 mmol) was dissolved in 40 ml of dry tetrahydrofuran cooled to -78 ° C in advance, and then the solution was slowly injected into the solution of the intermediate 1-9 at -78 ° C, slowly warmed to room temperature, and reacted for 12 hours; after the reaction, a small amount of methanol was added to quench the reaction. The reaction mixture was quenched, the solvent was evaporated under reduced pressure, 100 ml of glacial acetic acid and 10 ml of concentrated hydrochloric acid were added, and the temperature was raised to reflux; after reacting for 2 hours, the mixture was neutralized with a saturated aqueous sodium carbonate solution, the liquid was extracted with dichloromethane, and the organic phase was collected. The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated, and the compound was separated by silica gel column using a 5:1 volume ratio of petroleum ether and dichloromethane solution as a developing solvent to obtain intermediate 1-7. The molar weight of intermediate 1-7 was 7.59 mmol, the yield was 75.9%, and MS (ASAP) = 1118.

[0166] Synthesis of intermediate 1-8:

[0167] Intermediate 1-7 (10 mmol) was dissolved in 80 mL of DMF, 10 mmol of NBS was dissolved in 73 mL of DMF solvent, and then N-bromosuccinimide (NBS) solution was added dropwise to the substrate solution at a rate of 3-5 drops per second with stirring. The reaction was stopped at room temperature after the addition was completed. 30 mL of water was added dropwise to the reaction solution, and the liquid was extracted with dichloromethane and the organic phase was collected. The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated, and the organic phase was subjected to column chromatography and recrystallization to obtain intermediate 1-8. The molar weight of intermediate 1-8 was 7.17 mmol, the yield was 71.7%, and MS (ASAP) = 1196.

[0168] Synthesis of organic compound M1:

[0169] A 250 ml three-necked flask was charged with 10 mmol of intermediate 1-8 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30°C in a N2 atmosphere. A n-hexane solution of tert-butyllithium (t-BuLi) (21 mmol) was added dropwise. The temperature was raised to 60°C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was then evaporated under reduced pressure. The reaction solution was cooled to -30°C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0°C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and then the temperature was further raised to 120°C with stirring for 3 hours. The reaction solution was cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M1. The yield of organic compound M1 was 43.8%, and MS (ASAP) = 1126.

[0170] Example 2 Synthesis of Organic Compound M2

[0171] The synthetic route of organic compound M2 is as follows:

[0172]

[0173] Synthesis of intermediate 2-2:

[0174] Compound 1-4 (10 mmol) and compound 2-1 (10 mmol) were dissolved in a mixture 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 heated to 100°C under a nitrogen atmosphere and stirred for 6 h. After cooling, the solvent was mostly removed by rotary evaporation, and the mixture was then extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 2-2 with a molar weight of 7.43 mmol, a yield of 74.3%, and MS (ASAP) = 313.

[0175] Synthesis of intermediate 2-3:

[0176] In a two-necked flask, under a nitrogen atmosphere, intermediate 1-3 (10 mmol) was dissolved in 20 ml of dry tetrahydrofuran, cooled to -78°C, and a pentane solution of n-butyllithium (1 M, 12 ml) was added. The mixture was reacted at this temperature for 1 hour. Intermediate 2-2 (20 mmol) was dissolved in 40 ml of dry tetrahydrofuran, previously cooled to -78°C. This solution was then slowly injected into the solution of intermediate 2-2 at -78°C. The mixture was slowly warmed to room temperature and allowed to react for 12 hours. After the reaction was completed, a small amount of methanol was added to quench the reaction. The solvent was evaporated under reduced pressure, 100 ml of glacial acetic acid and 10 ml of concentrated hydrochloric acid were added, and the mixture was then heated to reflux. After reacting for 2 hours, the mixture was neutralized with a saturated aqueous sodium carbonate solution, and the liquid was extracted with dichloromethane and the organic phase was collected. The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated, and the compound was separated by silica gel column using a 5:1 volume ratio of petroleum ether and dichloromethane solution as a developing solvent to obtain intermediate 2-3 with a molar weight of 8.63 mmol and a yield of 86.3%. MS (ASAP) = 1222.

[0177] Synthesis of intermediate 2-4:

[0178] Intermediate 2-3 (10 mmol) was dissolved in 80 mL of DMF, and 10 mmol of NBS was dissolved in 73 mL of DMF. The NBS solution was then added dropwise to the substrate solution at a rate of 3-5 drops per second with stirring. The reaction was stopped at room temperature after the addition was complete. 30 mL of water was added dropwise to the reaction solution, and the mixture was extracted with dichloromethane. The organic phase was collected and dried over anhydrous sodium sulfate, filtered, concentrated, and recrystallized by column chromatography to obtain Intermediate 2-4 with a molar weight of 7.61 mmol and a yield of 76.1%. MS (ASAP) = 1300.

[0179] Synthesis of organic compound M2:

[0180] 10 mmol of intermediate 2-4 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 ° C in a N2 atmosphere, and a n-hexane solution of t-BuLi (21 mmol) was added dropwise. The temperature was raised to 60 ° C and the reaction was carried out for 2 hours. The n-hexane solvent was evaporated under reduced pressure. The reaction solution was cooled to -30 ° C again, boron tribromide (21 mmol) was added, and the temperature was raised to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0 ° C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and then the temperature was further raised to 120°C with stirring for 3 hours. The reaction solution was cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M2, with a yield of 49.3% and MS (ASAP) = 1230.

[0181] Example 3 Synthesis of Organic Compound M3

[0182] The synthetic route of organic compound M3 is as follows:

[0183]

[0184] Synthesis of intermediate 3-2:

[0185] Compound 1-4 (10 mmol) and compound 3-1 (10 mmol) were dissolved in a mixture 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 heated to 100°C under a nitrogen atmosphere and stirred for 6 h. After cooling, the solvent was mostly removed by rotary evaporation, and the mixture was then extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to afford intermediate 3-2 with a molar weight of 8.15 mmol and a yield of 81.5%. MS (ASAP) = 365.

[0186] Synthesis of intermediate 3-3:

[0187] In a two-necked flask under nitrogen, intermediate 1-3 (10 mmol) was dissolved in 20 ml of dry tetrahydrofuran, cooled to -78°C, and a pentane solution of n-butyllithium (1 M, 12 ml) was added. The mixture was reacted at this temperature for 1 hour. Intermediate 3-2 (20 mmol) was dissolved in 40 ml of dry tetrahydrofuran, previously cooled to -78°C. This solution was then slowly injected into the solution of intermediate 3-2 at -78°C. The mixture was slowly warmed to room temperature and allowed to react for 12 hours. After the reaction was completed, a small amount of methanol was added to quench the reaction. The solvent was evaporated under reduced pressure, 100 ml of glacial acetic acid and 10 ml of concentrated hydrochloric acid were added, and the mixture was then heated to reflux. After reacting for 2 hours, the mixture was neutralized with a saturated aqueous sodium carbonate solution, and the liquid was extracted with dichloromethane and the organic phase was collected. The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated, and the compound was separated by silica gel column using a 5:1 volume ratio of petroleum ether and dichloromethane solution as a developing solvent to obtain intermediate 3-3 with a molar weight of 7.83 mmol and a yield of 78.3%. MS (ASAP) = 1326.

[0188] Synthesis of intermediate 3-4:

[0189] Intermediate 3-3 (10 mmol) was dissolved in 80 mL of DMF, and 10 mmol of NBS was dissolved in 73 mL of DMF. The NBS solution was then added dropwise to the substrate solution at a rate of 3-5 drops per second with stirring. The reaction was stopped at room temperature after the addition was complete. 30 mL of water was added dropwise to the reaction solution, and the mixture was extracted with dichloromethane. The organic phase was collected and dried over anhydrous sodium sulfate, filtered, concentrated, and recrystallized by column chromatography to obtain Intermediate 3-4. The molar weight was 7.09 mmol, the yield was 70.9%, and the MS (ASAP) value was 1404.

[0190] Synthesis of organic compound M3:

[0191] 10 mmol of intermediate 3-4 and 100 ml of dry tert-butylbenzene were added to a 250 ml three-necked flask, cooled to -30 ° C in a N2 atmosphere, and a n-hexane solution of t-BuLi (21 mmol) was added dropwise. The temperature was raised to 60 ° C and the reaction was carried out for 2 hours. The n-hexane solvent was evaporated under reduced pressure. The reaction solution was cooled to -30 ° C again, boron tribromide (21 mmol) was added, and the temperature was raised to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0 ° C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and then the temperature was further raised to 120°C with stirring for 3 hours. The reaction solution was cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M3, with a yield of 43.8% and MS (ASAP) = 1334.

[0192] Example 4 Synthesis of Organic Compound M4

[0193] The synthetic route of organic compound M4 is as follows:

[0194]

[0195] Synthesis of intermediate 4-2:

[0196] Compound 1-4 (10 mmol) and compound 4-1 (10 mmol) were dissolved in a mixture 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 heated to 100°C under a nitrogen atmosphere and stirred for 6 h. After cooling, the solvent was mostly removed by rotary evaporation, and the mixture was then extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to afford intermediate 4-2 with a molar weight of 7.46 mmol and a yield of 74.6%. MS (ASAP) = 332.

[0197] Synthesis of intermediate 4-3:

[0198] In a two-necked flask under nitrogen, intermediate 1-3 (10 mmol) was dissolved in 20 ml of dry tetrahydrofuran, cooled to -78°C, and a pentane solution of n-butyllithium (1 M, 12 ml) was added. The mixture was reacted at this temperature for 1 hour. Intermediate 4-2 (20 mmol) was dissolved in 40 ml of dry tetrahydrofuran, previously cooled to -78°C. This solution was then slowly injected into the solution of intermediate 4-2 at -78°C. The mixture was slowly warmed to room temperature and allowed to react for 12 hours. After the reaction was completed, a small amount of methanol was added to quench the reaction. The solvent was evaporated under reduced pressure, 100 ml of glacial acetic acid and 10 ml of concentrated hydrochloric acid were added, and the mixture was then heated to reflux. After reacting for 2 hours, the mixture was neutralized with a saturated aqueous sodium carbonate solution, and the liquid was extracted with dichloromethane and the organic phase was collected. The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated, and the compound was separated by silica gel column using a 5:1 volume ratio of petroleum ether and dichloromethane solution as the developing solvent to obtain intermediate 4-3 with a molar weight of 7.83 mmol and a yield of 78.3%. MS (ASAP) = 1260.

[0199] Synthesis of intermediate 4-4:

[0200] Intermediate 4-3 (10 mmol) was dissolved in 80 mL of DMF, and 10 mmol of NBS was dissolved in 73 mL of DMF. The NBS solution was then added dropwise to the substrate solution at a rate of 3-5 drops per second with stirring. The reaction was stopped at room temperature after the addition was complete. 30 mL of water was added dropwise to the reaction solution, and the mixture was extracted with dichloromethane. The organic phase was collected and dried over anhydrous sodium sulfate, filtered, concentrated, and recrystallized by column chromatography to obtain Intermediate 4-4 with a molar weight of 6.73 mmol and a yield of 67.3%. MS (ASAP) = 1338.

[0201] Synthesis of organic compound M4:

[0202] A 250 ml three-necked flask was charged with 10 mmol of intermediate 4-4 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30 ° C in a N2 atmosphere. A n-hexane solution of t-BuLi (21 mmol) was added dropwise. The temperature was raised to 60 ° C and the reaction was continued for 2 hours. The n-hexane solvent was evaporated under reduced pressure. The reaction solution was cooled to -30 ° C again, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0 ° C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and then the temperature was further raised to 120°C with stirring for 3 hours. The reaction solution was cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M4, with a yield of 41.2% and MS (ASAP) = 1268.

[0203] Example 5 Synthesis of Organic Compound M5

[0204] The synthetic route of organic compound M5 is as follows:

[0205]

[0206] Synthesis of intermediate 5-2:

[0207] Compound 1-4 (10 mmol) and compound 5-1 (10 mmol) were dissolved in a mixture 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 under a nitrogen atmosphere for 6 h. After cooling, the solvent was mostly removed by rotary evaporation, and the resulting mixture was extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to afford intermediate 5-2 with a molar weight of 7.11 mmol and a yield of 71.1%. MS (ASAP) = 332.

[0208] Synthesis of intermediate 5-3:

[0209] In a two-necked flask under nitrogen, Intermediate 1-3 (10 mmol) was dissolved in 20 ml of dry tetrahydrofuran, cooled to -78°C, and a pentane solution of n-butyllithium (1 M, 12 ml) was added. The mixture was reacted at this temperature for 1 hour. Intermediate 5-2 (20 mmol) was dissolved in 40 ml of dry tetrahydrofuran, previously cooled to -78°C. This solution was then slowly injected into the solution of Intermediate 5-2 at -78°C. The mixture was slowly warmed to room temperature and allowed to react for 12 hours. After the reaction was completed, a small amount of methanol was added to quench the reaction. The solvent was evaporated under reduced pressure, 100 ml of glacial acetic acid and 10 ml of concentrated hydrochloric acid were added, and the mixture was then heated to reflux. After reacting for 2 hours, the mixture was neutralized with a saturated aqueous sodium carbonate solution. The liquid was extracted with dichloromethane and the organic phase was collected. The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated, and the compound was separated by silica gel column using a 5:1 volume ratio of petroleum ether and dichloromethane solution as the developing solvent to obtain intermediate 5-3 with a molar weight of 7.25 mmol and a yield of 72.5%. MS (ASAP) = 1260.

[0210] Synthesis of intermediate 5-4:

[0211] Intermediate 5-3 (10 mmol) was dissolved in 80 mL of DMF, and 10 mmol of NBS was dissolved in 73 mL of DMF. The NBS solution was then added dropwise to the substrate solution at a rate of 3-5 drops per second with stirring. The reaction was stopped at room temperature after the addition was complete. 30 mL of water was added dropwise to the reaction solution, and the mixture was extracted with dichloromethane. The organic phase was collected and dried over anhydrous sodium sulfate, filtered, concentrated, and recrystallized by column chromatography to obtain Intermediate 5-4. The molar weight was 6.19 mmol, the yield was 61.9%, and the MS (ASAP) value was 1338.

[0212] Synthesis of organic compound M5:

[0213] A 250 ml three-necked flask was charged with 10 mmol of intermediate 5-4 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30 ° C in a N2 atmosphere. A n-hexane solution of t-BuLi (21 mmol) was added dropwise. The temperature was raised to 60 ° C and the reaction was continued for 2 hours. The n-hexane solvent was evaporated under reduced pressure. The reaction solution was cooled to -30 ° C again, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0 ° C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and then the temperature was further raised to 120°C with stirring for 3 hours. The reaction solution was cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M5, with a yield of 36.8% and MS (ASAP) = 1268.

[0214] Example 6

[0215] The synthetic route of organic compound M6 is as follows:

[0216]

[0217] Synthesis of intermediate 6-2:

[0218] Compound 1-4 (10 mmol) and compound 6-1 (10 mmol) were dissolved in a mixture 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 under a nitrogen atmosphere for 6 h. After cooling, the solvent was mostly removed by rotary evaporation, and the resulting mixture was extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to afford intermediate 6-2 with a molar weight of 7.53 mmol and a yield of 75.3%. MS (ASAP) = 332.

[0219] Synthesis of intermediate 6-3:

[0220] In a two-necked flask under nitrogen, Intermediate 1-3 (10 mmol) was dissolved in 20 ml of dry tetrahydrofuran, cooled to -78°C, and a pentane solution of n-butyllithium (1 M, 12 ml) was added. The mixture was reacted at this temperature for 1 hour. Intermediate 6-2 (20 mmol) was dissolved in 40 ml of dry tetrahydrofuran, previously cooled to -78°C. This solution was then slowly injected into the solution of Intermediate 6-2 at -78°C. The mixture was slowly warmed to room temperature and allowed to react for 12 hours. After the reaction was completed, a small amount of methanol was added to quench the reaction. The solvent was evaporated under reduced pressure, 100 ml of glacial acetic acid and 10 ml of concentrated hydrochloric acid were added, and the mixture was then heated to reflux. After reacting for 2 hours, the mixture was neutralized with a saturated aqueous sodium carbonate solution, and the liquid was extracted with dichloromethane and the organic phase was collected. The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated, and the compound was separated by silica gel column using a 5:1 volume ratio of petroleum ether and dichloromethane solution as the developing solvent to obtain intermediate 6-3 with a molar weight of 6.48 mmol and a yield of 64.8%. MS (ASAP) = 1260.

[0221] Synthesis of intermediate 6-4:

[0222] Intermediate 6-3 (10 mmol) was dissolved in 80 mL of DMF, and 10 mmol of NBS was dissolved in 73 mL of DMF. The NBS solution was then added dropwise to the substrate solution at a rate of 3-5 drops per second with stirring. The reaction was stopped at room temperature after the addition was complete. 30 mL of water was added dropwise to the reaction solution, and the mixture was extracted with dichloromethane. The organic phase was collected and dried over anhydrous sodium sulfate, filtered, concentrated, and recrystallized by column chromatography to obtain Intermediate 6-4. The molar weight was 5.61 mmol, the yield was 56.1%, and the MS (ASAP) value was 1338.

[0223] Synthesis of organic compound M6:

[0224] A 250 ml three-necked flask was charged with 10 mmol of intermediate 6-4 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30 ° C in a N2 atmosphere. A n-hexane solution of t-BuLi (21 mmol) was added dropwise. The temperature was raised to 60 ° C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was evaporated under reduced pressure. The reaction solution was cooled to -30 ° C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0 ° C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and then the temperature was further raised to 120°C with stirring for 3 hours. The reaction solution was cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M6, with a yield of 32.3% and MS (ASAP) = 1268.

[0225] Example 7 Synthesis of Organic Compound M7

[0226] The synthetic route of organic compound M7 is as follows:

[0227]

[0228]

[0229] Synthesis of intermediate 7-2:

[0230] Compound 1-4 (10 mmol) and compound 7-1 (10 mmol) were dissolved in a mixture 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 under a nitrogen atmosphere for 6 h. After cooling, the solvent was mostly removed by rotary evaporation, and the resulting mixture was extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to afford intermediate 7-2 with a molar weight of 6.28 mmol and a yield of 62.8%. MS (ASAP) = 274.

[0231] Synthesis of intermediate 7-3:

[0232] In a two-necked flask under nitrogen, Intermediate 1-3 (10 mmol) was dissolved in 20 ml of dry tetrahydrofuran, cooled to -78°C, and a pentane solution of n-butyllithium (1 M, 12 ml) was added. The mixture was reacted at this temperature for 1 hour. Intermediate 7-2 (20 mmol) was dissolved in 40 ml of dry tetrahydrofuran, previously cooled to -78°C. This solution was then slowly injected into the solution of Intermediate 7-2 at -78°C. The mixture was slowly warmed to room temperature and allowed to react for 12 hours. After the reaction was completed, a small amount of methanol was added to quench the reaction. The solvent was evaporated under reduced pressure, 100 ml of glacial acetic acid and 10 ml of concentrated hydrochloric acid were added, and the mixture was then heated to reflux. After reacting for 2 hours, the mixture was neutralized with a saturated aqueous sodium carbonate solution, and the liquid was extracted with dichloromethane and the organic phase was collected. The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated, and the compound was separated by silica gel column using a 5:1 volume ratio of petroleum ether and dichloromethane solution as the developing solvent to obtain intermediate 7-3 with a molar weight of 7.04 mmol and a yield of 70.4%. MS (ASAP) = 1144.

[0233] Synthesis of intermediate 7-4:

[0234] Intermediate 7-3 (10 mmol) was dissolved in 80 mL of DMF, and 10 mmol of NBS was dissolved in 73 mL of DMF. The NBS solution was then added dropwise to the substrate solution at a rate of 3-5 drops per second with stirring. The reaction was stopped at room temperature after the addition was complete. 30 mL of water was added dropwise to the reaction solution, and the mixture was extracted with dichloromethane. The organic phase was collected and dried over anhydrous sodium sulfate, filtered, concentrated, and recrystallized by column chromatography to obtain Intermediate 7-4. The molar weight was 8.41 mmol, the yield was 84.1%, and the MS (ASAP) value was 1222.

[0235] Synthesis of organic compound M7:

[0236] A 250 ml three-necked flask was charged with 10 mmol of intermediate 7-4 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30 ° C in a N2 atmosphere. A n-hexane solution of t-BuLi (21 mmol) was added dropwise. The temperature was raised to 60 ° C and the reaction was continued for 2 hours. The n-hexane solvent was evaporated under reduced pressure. The reaction solution was cooled to -30 ° C again, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0 ° C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and then the temperature was further raised to 120°C with stirring for 3 hours. The reaction solution was cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M7, with a yield of 50.1% and MS (ASAP) = 1152.

[0237] Example 8

[0238] The synthetic route of organic compound M8 is as follows:

[0239]

[0240] Synthesis of intermediate 8-2:

[0241] Compound 1-4 (10 mmol) and compound 8-1 (10 mmol) were dissolved in a mixture 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 under a nitrogen atmosphere for 6 h. After cooling, the solvent was mostly removed by rotary evaporation, and the resulting mixture was extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to afford intermediate 8-2 with a molar weight of 7.86 mmol and a yield of 78.6%. MS (ASAP) = 328.

[0242] Synthesis of intermediate 8-3:

[0243] In a two-necked flask under nitrogen, Intermediate 1-3 (10 mmol) was dissolved in 20 ml of dry tetrahydrofuran, cooled to -78°C, and a pentane solution of n-butyllithium (1 M, 12 ml) was added. The mixture was reacted at this temperature for 1 hour. Intermediate 8-2 (20 mmol) was dissolved in 40 ml of dry tetrahydrofuran, previously cooled to -78°C. This solution was then slowly injected into the solution of Intermediate 8-2 at -78°C. The mixture was slowly warmed to room temperature and allowed to react for 12 hours. After the reaction was completed, a small amount of methanol was added to quench the reaction. The solvent was evaporated under reduced pressure, 100 ml of glacial acetic acid and 10 ml of concentrated hydrochloric acid were added, and the mixture was then heated to reflux. After reacting for 2 hours, the mixture was neutralized with a saturated aqueous sodium carbonate solution, and the liquid was extracted with dichloromethane and the organic phase was collected. The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated, and the compound was separated by silica gel column using a 5:1 volume ratio of petroleum ether and dichloromethane solution as the developing solvent to obtain intermediate 8-3 with a molar weight of 7.28 mmol and a yield of 72.8%. MS (ASAP) = 1252.

[0244] Synthesis of intermediate 8-4:

[0245] Intermediate 8-3 (10 mmol) was dissolved in 80 mL of DMF, and 10 mmol of NBS was dissolved in 73 mL of DMF. The NBS solution was then added dropwise to the substrate solution at a rate of 3-5 drops per second with stirring. The reaction was stopped at room temperature after the addition was complete. 30 mL of water was added dropwise to the reaction solution, and the mixture was extracted with dichloromethane. The organic phase was collected and dried over anhydrous sodium sulfate, filtered, concentrated, and recrystallized by column chromatography to obtain Intermediate 8-4. The molar weight was 8.05 mmol, the yield was 80.5%, and the MS (ASAP) value was 1330.

[0246] Synthesis of organic compound M8:

[0247] A 250 ml three-necked flask was charged with 10 mmol of intermediate 8-4 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30 ° C in a N2 atmosphere. A n-hexane solution of t-BuLi (21 mmol) was added dropwise. The temperature was raised to 60 ° C and the reaction was allowed to proceed for 2 hours. The n-hexane solvent was evaporated under reduced pressure. The reaction solution was cooled to -30 ° C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0 ° C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and then the temperature was further raised to 120°C with stirring for 3 hours. The reaction solution was cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M8, with a yield of 33.7% and MS (ASAP) = 1260.

[0248] Example 9 Synthesis of Organic Compound M9

[0249] The synthetic route of organic compound M9 is as follows:

[0250]

[0251] Synthesis of intermediate 9-2:

[0252] Compound 1-4 (10 mmol) and compound 9-1 (10 mmol) were dissolved in a mixture 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 under a nitrogen atmosphere for 6 h. After cooling, the solvent was mostly removed by rotary evaporation, and the resulting mixture was extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to afford intermediate 9-2 with a molar weight of 8.62 mmol and a yield of 86.2%. MS (ASAP) = 296.

[0253] Synthesis of intermediate 9-3:

[0254] In a two-necked flask under nitrogen, Intermediate 1-3 (10 mmol) was dissolved in 20 ml of dry tetrahydrofuran, cooled to -78°C, and a pentane solution of n-butyllithium (1 M, 12 ml) was added. The mixture was reacted at this temperature for 1 hour. Intermediate 9-2 (20 mmol) was dissolved in 40 ml of dry tetrahydrofuran, previously cooled to -78°C. This solution was then slowly injected into the solution of Intermediate 9-2 at -78°C. The mixture was slowly warmed to room temperature and allowed to react for 12 hours. After the reaction was completed, a small amount of methanol was added to quench the reaction. The solvent was evaporated under reduced pressure, 100 ml of glacial acetic acid and 10 ml of concentrated hydrochloric acid were added, and the mixture was then heated to reflux. After reacting for 2 hours, the mixture was neutralized with a saturated aqueous sodium carbonate solution, and the liquid was extracted with dichloromethane and the organic phase was collected. The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated, and the compound was separated by silica gel column using a 5:1 volume ratio of petroleum ether and dichloromethane solution as the developing solvent to obtain intermediate 9-3 with a molar weight of 6.35 mmol and a yield of 63.5%. MS (ASAP) = 1188.

[0255] Synthesis of intermediate 9-4:

[0256] Intermediate 9-3 (10 mmol) was dissolved in 80 mL of DMF, and 10 mmol of NBS was dissolved in 73 mL of DMF. The NBS solution was then added dropwise to the substrate solution at a rate of 3-5 drops per second with stirring. The reaction was stopped at room temperature after the addition was complete. 30 mL of water was added dropwise to the reaction solution, and the mixture was extracted with dichloromethane. The organic phase was collected and dried over anhydrous sodium sulfate, filtered, concentrated, and recrystallized by column chromatography to obtain Intermediate 9-4. The molar weight was 8.57 mmol, the yield was 85.7%, and the MS (ASAP) value was 1266.

[0257] Synthesis of organic compound M9:

[0258] A 250 ml three-necked flask was charged with 10 mmol of intermediate 9-4 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30 ° C in a N2 atmosphere. A n-hexane solution of t-BuLi (21 mmol) was added dropwise. The temperature was raised to 60 ° C and the reaction was continued for 2 hours. The n-hexane solvent was evaporated under reduced pressure. The reaction solution was cooled to -30 ° C again, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0 ° C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and then the temperature was further raised to 120°C with stirring for 3 hours. The reaction solution was cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M9, with a yield of 34.8% and MS (ASAP) = 1196.

[0259] Example 10

[0260] The synthetic route of organic compound M10 is as follows:

[0261]

[0262] Synthesis of intermediate 10-2:

[0263] Compound 1-4 (10 mmol) and compound 10-1 (10 mmol) were dissolved in a mixture of 1,4-dioxane and water (21 ml / 2 ml), and Pd(PPh3)4 (0.1) and potassium carbonate (30 mmol) were added. The mixture was stirred at 100°C for 6 h under a nitrogen atmosphere. After cooling, the solvent was mostly removed by rotary evaporation, and the resulting mixture was extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to afford intermediate 10-2 with a molar weight of 8.37 mmol and a yield of 83.7%. MS (ASAP) = 310.

[0264] Synthesis of intermediate 10-3:

[0265] In a two-necked flask under nitrogen, Intermediate 1-3 (10 mmol) was dissolved in 20 ml of dry tetrahydrofuran, cooled to -78°C, and a pentane solution of n-butyllithium (1 M, 12 ml) was added. The mixture was allowed to react at this temperature for 1 hour. Intermediate 10-2 (20 mmol) was dissolved in 40 ml of dry tetrahydrofuran, previously cooled to -78°C. This solution was then slowly injected into the solution of Intermediate 10-2 at -78°C. The mixture was slowly warmed to room temperature and allowed to react for 12 hours. After the reaction was completed, a small amount of methanol was added to quench the reaction. The solvent was evaporated under reduced pressure, 100 ml of glacial acetic acid and 10 ml of concentrated hydrochloric acid were added, and the mixture was then heated to reflux. After reacting for 2 hours, the mixture was neutralized with a saturated aqueous sodium carbonate solution, and the liquid was extracted with dichloromethane and the organic phase was collected. The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated, and the compound was separated by silica gel column using a 5:1 volume ratio of petroleum ether and dichloromethane solution as a developing solvent to obtain the intermediate 10-3 with a molar weight of 6.13 mmol and a yield of 61.3%. MS (ASAP) = 1216.

[0266] Synthesis of intermediate 10-4:

[0267] Intermediate 10-3 (10 mmol) was dissolved in 80 mL of DMF, and 10 mmol of NBS was dissolved in 73 mL of DMF. The NBS solution was then added dropwise to the substrate solution at a rate of 3-5 drops per second with stirring. The reaction was stopped at room temperature after the addition was complete. 30 mL of water was added dropwise to the reaction solution, and the mixture was extracted with dichloromethane. The organic phase was collected and dried over anhydrous sodium sulfate, filtered, concentrated, and recrystallized by column chromatography to obtain Intermediate 10-4. The molar weight was 8.17 mmol, the yield was 81.7%, and the MS (ASAP) value was 1294.

[0268] Synthesis of organic compound M10:

[0269] A 250 ml three-necked flask was charged with 10 mmol of intermediate 10-4 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30 ° C in a N2 atmosphere. A n-hexane solution of t-BuLi (21 mmol) was added dropwise. The temperature was raised to 60 ° C and the reaction was continued for 2 hours. The n-hexane solvent was evaporated under reduced pressure. The reaction solution was cooled to -30 ° C again, boron tribromide (21 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0 ° C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and then the temperature was further raised to 120°C with stirring for 3 hours. The reaction solution was cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M10, with a yield of 32.5% and MS (ASAP) = 1224.

[0270] Example 11

[0271] The synthetic route of organic compound M11 is as follows:

[0272]

[0273]

[0274] Synthesis of intermediate 11-2:

[0275] Compound 1-4 (10 mmol) and compound 11-1 (10 mmol) were dissolved in a mixture 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 under a nitrogen atmosphere for 6 h. After cooling, the solvent was mostly removed by rotary evaporation, followed by extraction and water washing. The organic phase was purified by column chromatography and recrystallization to afford intermediate 11-2 with a molar weight of 6.33 mmol and a yield of 63.3%. MS (ASAP) = 419.

[0276] Synthesis of intermediate 11-3:

[0277] In a two-necked flask under nitrogen, Intermediate 1-3 (10 mmol) was dissolved in 20 ml of dry tetrahydrofuran, cooled to -78°C, and a pentane solution of n-butyllithium (1 M, 12 ml) was added. The mixture was allowed to react at this temperature for 1 hour. Intermediate 11-2 (20 mmol) was dissolved in 40 ml of dry tetrahydrofuran, previously cooled to -78°C. This solution was then slowly injected into the solution of Intermediate 11-2 at -78°C. The mixture was slowly warmed to room temperature and allowed to react for 12 hours. After the reaction was completed, a small amount of methanol was added to quench the reaction. The solvent was evaporated under reduced pressure, 100 ml of glacial acetic acid and 10 ml of concentrated hydrochloric acid were added, and the mixture was then heated to reflux. After reacting for 2 hours, the mixture was neutralized with saturated aqueous sodium carbonate solution, extracted with dichloromethane, and the organic phase was collected. The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated, and the compound was separated by silica gel column using a 5:1 volume ratio of petroleum ether and dichloromethane solution as the developing solvent to obtain intermediate 11-3 with a molar weight of 5.47 mmol and a yield of 54.7%. MS (ASAP) = 1434.

[0278] Synthesis of intermediate 11-4:

[0279] Intermediate 11-3 (10 mmol) was dissolved in 80 mL of DMF, and 10 mmol of NBS was dissolved in 73 mL of DMF. The NBS solution was then added dropwise to the substrate solution at a rate of 3-5 drops per second with stirring. The reaction was stopped at room temperature after the addition was complete. 30 mL of water was added dropwise to the reaction solution, and the mixture was extracted with dichloromethane. The organic phase was collected and dried over anhydrous sodium sulfate, filtered, concentrated, and recrystallized by column chromatography to obtain Intermediate 11-4, with a molar weight of 7.26 mmol and a yield of 72.6%. MS (ASAP) = 1512.

[0280] Synthesis of organic compound M11:

[0281] A 250 ml three-necked flask was charged with 10 mmol of intermediate 11-4 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30 °C in a N2 atmosphere. A n-hexane solution of t-BuLi (21 mmol) was added dropwise. The temperature was raised to 60 °C and the reaction was continued for 2 hours. The n-hexane solvent was evaporated under reduced pressure. The reaction solution was cooled to -30 °C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0 °C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and then the temperature was further raised to 120°C with stirring for 3 hours. The reaction solution was then cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M11, with a yield of 24.9% and MS (ASAP) = 1442.

[0282] Example 12 Synthesis of Organic Compound M12

[0283] The synthetic route of organic compound M12 is as follows:

[0284]

[0285] Synthesis of intermediate 12-2:

[0286] Compound 1-4 (10 mmol) and compound 12-1 (10 mmol) were dissolved in a mixture of 1,4-dioxane and water (21 ml / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium tert-butoxide (30 mmol) were added. The mixture was stirred at 100°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was mostly removed by rotary evaporation, and the resulting mixture was extracted and washed with water. The organic phase was purified by column chromatography and recrystallized to afford intermediate 12-2 with a molar weight of 6.05 mmol and a yield of 60.5%. MS (ASAP) = 345.

[0287] Synthesis of intermediate 12-3:

[0288] In a two-necked flask under nitrogen, Intermediate 1-3 (10 mmol) was dissolved in 20 ml of dry tetrahydrofuran, cooled to -78°C, and a pentane solution of n-butyllithium (1 M, 12 ml) was added. The mixture was reacted at this temperature for 1 hour. Intermediate 12-2 (20 mmol) was dissolved in 40 ml of dry tetrahydrofuran, previously cooled to -78°C. This solution was then slowly injected into the solution of Intermediate 12-2 at -78°C. The mixture was slowly warmed to room temperature and allowed to react for 12 hours. After the reaction was completed, a small amount of methanol was added to quench the reaction. The solvent was evaporated under reduced pressure, 100 ml of glacial acetic acid and 10 ml of concentrated hydrochloric acid were added, and the mixture was then heated to reflux. After 2 hours of reaction, the mixture was neutralized with saturated aqueous sodium carbonate solution, and the liquid was extracted with dichloromethane, and the organic phase was collected. The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated, and the compound was separated by silica gel column using a 5:1 volume ratio of petroleum ether and dichloromethane solution as the developing solvent to obtain intermediate 12-3 with a molar weight of 5.17 mmol and a yield of 51.7%. MS (ASAP) = 1286.

[0289] Synthesis of intermediate 12-4:

[0290] Intermediate 12-3 (10 mmol) was dissolved in 80 mL of DMF, and 10 mmol of NBS was dissolved in 73 mL of DMF. The NBS solution was then added dropwise to the substrate solution at a rate of 3-5 drops per second with stirring. The reaction was stopped at room temperature after the addition was complete. 30 mL of water was added dropwise to the reaction solution, and the mixture was extracted with dichloromethane. The organic phase was collected and dried over anhydrous sodium sulfate, filtered, concentrated, and recrystallized by column chromatography to obtain Intermediate 12-4, with a molar weight of 6.74 mmol and a yield of 67.4%. MS (ASAP) = 1364.

[0291] Synthesis of organic compound M12:

[0292] A 250 ml three-necked flask was charged with 10 mmol of intermediate 12-4 and 100 ml of dry tert-butylbenzene. The mixture was cooled to -30 °C in a N2 atmosphere. A n-hexane solution of t-BuLi (21 mmol) was added dropwise. The temperature was raised to 60 °C and the reaction was continued for 2 hours. The n-hexane solvent was evaporated under reduced pressure. The reaction solution was cooled to -30 °C again, and boron tribromide (21 mmol) was added. The mixture was heated to room temperature and stirred for 0.5 hours. The reaction solution was then cooled to 0 °C and 42 mmol of After the addition of N,N-diisopropylethylamine was complete, the temperature was raised to room temperature with stirring, and then the temperature was further raised to 120°C with stirring for 3 hours. The reaction solution was cooled to room temperature; an aqueous sodium carbonate solution and ethyl acetate were added to quench the reaction; the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and the solvent was removed by rotary evaporation to obtain a crude product, which was then purified using a flash silica gel column to obtain a pure product; the product was recrystallized from toluene and ethyl acetate to obtain a light yellow solid powder, i.e., organic compound M12, with a yield of 22.1% and MS (ASAP) = 1294.

[0293] Comparative Example 1

[0294] Comparative compound 1 (the synthesis method is described in Toward a BT.2020 green emitter through a combined multiple resonance effect and multi-lock strategy | Nature Communications) was used as a comparative example for the above Examples 1 to 12. The structural formula of the organic compound Ref-1 is shown below:

[0295]

[0296] The HOMO energy level, LUMO energy level, T1 energy level, and S1 energy level of compounds M1 to M12 obtained in Examples 1 to 12 and comparative compound 1 in Comparative Example 1 can be obtained by quantum calculation. Specifically, TD-DFT (time-dependent density functional theory) was used with Gaussian09W (Gaussian Inc.). The specific simulation method can be found in WO2011141110. The molecular geometry was 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 was calculated using TD-DFT (time-dependent density functional theory) and "TD-SCF / DFT / Default Spin / B3PW91" with the basis set "6-31G(d)" (Charge 0 / Spin Singlet). The HOMO and LUMO energy levels were calculated according to the following calibration formula, and the S1 and T1 levels were used directly.

[0297] HOMO(eV)=((HOMO(G)×27.212)-0.9899) / 1.1206;

[0298] LUMO(eV)=((LUMO(G)×27.212)-2.0041) / 1.385;

[0299] Wherein, HOMO, LUMO, T1, and S1 are the direct calculation results of Gaussian 09W, and the unit is Hartree. The calculation results of the HOMO energy level, LUMO energy level, T1 energy level, and S1 energy level of compounds M1 to M12 obtained in Examples 1 to 12 and comparative compound 1 in Comparative Example 1 are shown in Table 1.

[0300] Table 1: Calculation results of HOMO, LUMO, S1 energy level and T1 energy level of organic compounds M1 to M12 and comparative compound 1

[0301] Compound HOMO[eV] LUMO[eV] T1[eV] S1[eV] Example 1 Organic compound M1 -5.13 -2.81 1.86 2.21 Example 2 Organic compound M2 -5.04 -2.82 1.88 2.23 Example 3 Organic Compound M3 -5.11 -2.77 1.79 2.31 Example 4 Organic Compound M4 -5.15 -2.79 1.81 2.22 Example 5 Organic Compound M5 -5.03 -2.75 1.81 2.25 Example 6 Organic Compound M6 -5.01 -2.73 1.85 2.24 Example 7 Organic Compound M7 -5.06 -2.71 1.81 2.25 Example 8 Organic Compound M8 -5.02 -2.79 1.83 2.24 Example 9 Organic Compound M9 -5.04 -2.80 1.78 2.31 Example 10 Organic Compound M10 -5.11 -2.75 1.79 2.19 Example 11 Organic Compound M11 -5.18 -2.72 1.80 2.22 Example 12 Organic Compound M12 -5.19 -2.72 1.80 2.22 Comparative Example 1 Comparative compound Ref-1 -5.25 -2.89 1.91 2.45

[0302] As can be seen from Table 1, the organic compounds M1 to M12 provided in Examples 1 to 12 of the present application have added Ar1 and Ar2 steric hindering groups compared to the comparative compound Ref-1 provided in Comparative Example 1. It can be seen that after the steric hindering groups are added, the absolute values ​​of the HOMO energy levels of the organic compounds shown in Examples 1 to 12 are significantly reduced, which makes it easier to inject holes when the organic compounds provided in Examples 1 to 12 are used in organic light-emitting devices; therefore, compared with the comparative compound Ref-1 provided in Comparative Example 1, the organic compounds provided in Examples 1 to 12 of the present application can achieve effective hole injection at a lower voltage, thereby improving the luminous brightness of the organic light-emitting device. Due to the increased brightness, the green light emission visually appears deeper.

[0303] Furthermore, the organic compounds provided in Examples 1 to 12 exhibit significantly lower T1 values ​​compared to the comparative compound Ref-1 provided in Comparative Example 1. This results in lower excited-state energy, a lower probability of non-radiative transitions when heated, and improved thermal stability. Under high-temperature or long-term operating conditions, the material maintains stable luminescence performance, extending its lifespan, thereby reducing replacement costs and improving operational efficiency. Furthermore, the organic compounds provided in Examples 1 to 12 exhibit significantly lower S1 values ​​compared to the comparative compound Ref-1 provided in Comparative Example 1. Because the excited-state energy is lower, the structural changes in the molecule in the excited state are relatively minor, making it less likely for chemical bonds within the molecule to break or rearrange. This makes the material more stable during luminescence, reducing the degradation of luminescence performance or material aging caused by changes in the molecular structure and extending its service life.

[0304] At the same time, compared with the reference compound Ref-1, due to the decrease in T1 energy level and S1 energy level, especially the S1 value dropped to about 2.3, corresponding to the green light emission wavelength of about 530nm, the green light emitted by the organic compounds M1 to M12 is more inclined to dark green, which is theoretically beneficial for green organic light-emitting devices using organic compounds M1 to M12 as guest materials in the light-emitting layer to obtain better color coordinates.

[0305] (2) Application Examples

[0306] The compounds involved in this application example are as follows:

[0307]

[0308] Exemplary embodiment 1

[0309] Example 1 provides a manufacturing process of an organic light emitting device. Figure 2 The structure shown.

[0310] In the organic light-emitting device provided in this embodiment, ITO (indium tin oxide) is used as the anode, PEDOT (polyethylene dioxythiophene, Clevios TM AI4083) is used as a material for the hole injection layer, PVK (poly(9-vinylcarbazole, Sigma Aldrich, average Mn 25,000-50,000) is used as a material for the hole transport layer, GH-P and GH-N (whose structural formulas are shown below) are used as host materials in the light-emitting layer of the corresponding organic light-emitting device, the organic compound M1 in Example 1 is used as a guest material in the light-emitting layer of the corresponding organic light-emitting device, ET and Liq (lithium 8-hydroxyquinoline) are used as materials for the electron transport layer, and Al is used as a cathode. The specific preparation steps are as follows:

[0311] a. Cleaning of ITO anode: Use chloroform, acetone and / or isopropyl alcohol to clean the ITO conductive glass, and then perform UV ozone treatment;

[0312] b. Forming a hole injection layer: Spin-coating the hole injection layer material PEDOT (polyethylenedioxythiophene, Clevios TM AI4083) and treated on a hot plate at 180°C for 10 minutes. The thickness of the hole injection layer was 40 nm.

[0313] c. Forming a hole transport layer: A 5 mg / ml toluene solution of PVK (Sigma Aldrich, Mn 25,000-50,000) was spin-coated on the hole injection layer and then heated on a hot plate at 180°C for 60 minutes. The thickness of the hole transport layer was 20 nm.

[0314] d. Forming a light-emitting layer: In a nitrogen glove box, spin-coating a light-emitting layer material on the hole transport layer, followed by treatment on a hot plate at 140° C. for 10 minutes. The host materials in the light-emitting layer of the organic light-emitting device are GH-P and GH-N, and the guest materials in the light-emitting layers of different organic light-emitting devices correspond to one of organic compounds M1 to M12, respectively. The solvent is methyl benzoate solution. The mass ratio of GH-P, GH-N, and the guest material is 42.5:52.5:5. The concentration of the light-emitting layer material is 15 mg / ml. The thickness of the finally formed light-emitting layer is 40 nm.

[0315] e. Forming the electron transport layer: In a vacuum chamber, ET and Liq are placed in different evaporation units above the light-emitting layer and heated in a high vacuum (1×10 -6 ET and Liq were co-deposited at a weight ratio of 50:50 under a 20 mbar (mbar) environment to form an electron transport layer with a thickness of 20 nm;

[0316] f. Forming a cathode layer: depositing Al on the electron transport layer to obtain an Al cathode with a thickness of 100 nm;

[0317] g. Packaging: The device was encapsulated with UV-curable resin in a nitrogen glove box.

[0318] Exemplary Embodiments 2 to 12

[0319] Exemplary embodiments 2 to 12 respectively provide steps for manufacturing an organic light-emitting device. The structure and manufacturing steps thereof are similar to those of exemplary embodiment 1, except that the guest material is replaced by the guest material shown in Table 2.

[0320] Comparative Example

[0321] Comparative Example A manufacturing process of a comparative element 1 is provided. The structure and manufacturing process of the comparative element 1 are similar to those of the exemplary embodiment 1, except that the guest material is replaced with the comparative compound Ref-2.

[0322] In this application, the organic light-emitting devices provided in exemplary embodiments 1 to 12 and the comparative element 1 provided in the comparative embodiment were tested for current-voltage (JV) characteristics, and the CIE color coordinates (x, y), the driving voltage at 1 knits brightness (voltage @ 1 knits [V]), and the current density of 10 mA / cm 2 The luminous efficiency (CE@1knits[cd / A]) obtained when the luminance is 1knits is 200 nm and the time taken for the luminance to drop from the initial luminance of 1knits to 95% of the initial luminance (LT90@1knits[h]) is shown in Table 2.

[0323] In the examples of the present application, the color coordinates and current efficiency were tested using an IVL test system model FS-5500GA4, and the instrument life was tested using a D3000-256CH instrument.

[0324] Table 2 Performance test results of the organic light emitting elements of the exemplary embodiment and the comparative example

[0325]

[0326] As can be seen from Table 2, the organic light-emitting devices provided by exemplary embodiments 1 to 12 of the present application use organic compounds M1 to M12 as guest materials in their light-emitting layers, compared to comparative element 1. It can be seen that the x value of the color coordinates of the organic light-emitting elements of comparative exemplary embodiments 1 to 12 decreases to around 0.24, while the y value increases to around 0.7. For green light emission, the color coordinates presented by the embodiments of the present application are closer to the color coordinates of dark green, and are therefore more excellent.

[0327] Secondly, the luminous efficiency of the organic light-emitting devices provided in Examples 1 to 12 is all between 170 and 185 cd / A, indicating that the luminous efficiency is much higher than that of the comparative element 1, indicating that the organic compounds M1 to M12 in the examples of the present application can improve the luminous efficiency of the organic light-emitting devices after being applied to the organic light-emitting devices.

[0328] Moreover, the time taken for the brightness of the organic light-emitting devices provided in Examples 1 to 12 to decrease from the initial brightness of 1 knits to 95% of the initial brightness is all within the range of 760 to 790 h. Compared with the time taken for the brightness of the comparative elements 1 to 3 to decrease from the initial brightness of 1 knits to 95% of the initial brightness, the improvement is about 150%, indicating that the organic compounds M1 to M12 in the examples of the present application can improve the service life of the organic light-emitting devices after being applied to the organic light-emitting devices.

[0329] Furthermore, the applicant discovered in experiments that by introducing D or trimethylsilyl groups into Ar1 and Ar2, the luminous efficiency of the organic light-emitting device can be further improved to 180-185 cd / A.

[0330] In summary, the present application provides an organic compound represented by the general formula (1). The organic compound represented by the general formula (1) can increase the molecular planar structure of the organic compound by introducing a double hexagonal spirofluorene and a steric hindering group into a boron-nitrogen compound to increase the overall conjugation of the organic compound, thereby enhancing the solubility of the organic compound in the solvent, making the organic compound easy to purify, thereby increasing the purity of the organic compound and improving the material properties; when the organic compound is applied to an organic light-emitting device, it is beneficial to improve the luminous efficiency of the organic light-emitting device and help extend the service life of the organic light-emitting device. At the same time, the absolute value of the HOMO energy level, the absolute value of the LUMO energy level, the T1 energy level, and the S1 energy level of the organic compound represented by the general formula (1) are all low, and the chemical stability is increased, so that when the organic compound is applied to an organic light-emitting device, the service life of the device can be further extended.

[0331] In the description of this application, the terms "first" and "second" are used for descriptive purposes only and should not be understood to indicate or imply relative importance or implicitly specify the number of technical features indicated. Therefore, a feature defined as "first" or "second" may explicitly or implicitly include one or more features. In the description of this application, "plurality" means two or more, unless otherwise specifically defined.

[0332] In the above embodiments, the description of each embodiment has its own focus. For parts that are not described in detail in a certain embodiment, reference can be made to the relevant descriptions of other embodiments.

[0333] The embodiments, implementation methods and related technical features of the present application can be combined and replaced with each other without conflict.

[0334] The above are merely preferred embodiments of the present application and do not constitute any form of limitation to the present application. However, any simple modifications, equivalent changes, and modifications made to the above embodiments based on the technical essence of the present application without departing from the content of the technical solution of the present application are still within the scope of the technical solution of the present application.

Claims

1. An organic compound, characterized in that The structural formula of the organic compound is shown in formula (1): wherein Ar1 and Ar2 are selected from the structure represented by any one of formula (B-1) to formula (B-16): W1 is selected from CR6R7, SiR6R7, O, S, S=O or SO2; R1 to R7 are selected from H, D, an alkyl group having 1 to 20 carbon atoms, a silicon group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a thioalkoxy group having 1 to 20 carbon atoms, a silyl group, a trimethylsilyl group, a triphenylsilyl group, a keto group having 1 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, an aryloxycarbonyl group having 7 to 20 carbon atoms, an alkene group having 1 to 20 carbon atoms, CN , carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, CF3, Cl, Br, F, a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring atoms, and a substituted or unsubstituted heteroaryloxy group having 5 to 30 ring atoms; n1 is any integer selected from 0 to 4; n2 is any integer selected from 0 to 7; n3 is any integer selected from 0 to 9; n4 is selected from any integer between 0 and 11; n5 is any integer selected from 0 to 10; n6 is selected from any integer between 0 and 8; n7 is any integer selected from 0 to 4; n8 is any integer selected from 0 to 6; n9 is any integer selected from 0 to 5; n10 is any integer selected from 0 to 9.

2. The organic compound according to claim 1, characterized in that R1 to R4 are selected from one or more combinations of H, D, or an alkyl group having 1 to 14 carbon atoms; and / or R5 is selected from one or more combinations of H, D, or an alkyl group having 1 to 10 carbon atoms.

3. The organic compound according to claim 1, characterized in that The R5 is selected from any of the following structures: V is selected from CR8 or N; W2 is selected from NR9, CR9R 10 、SiR9R 10 , O, S, S=O or SO2; R8-R 10 a combination of one or more selected from H, D, an alkyl group having 1 to 20 C atoms, an alkoxy group having 1 to 20 C atoms, a thioalkoxy group having 1 to 20 C atoms, a silyl group, a keto group having 1 to 20 C atoms, an alkoxycarbonyl group having 2 to 20 C atoms, an aryloxycarbonyl group having 7 to 20 C atoms, a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, an amine group, CF3, Cl, Br, F, I, a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, a substituted or unsubstituted aryloxy group having 5 to 60 ring atoms, and a substituted or unsubstituted heteroaryloxy group having 5 to 60 ring atoms; 4. The organic compound according to claim 1, characterized in that Ar1 and Ar2 are selected from any of the following structures: R5 is selected from one or more combinations of H, D, trimethylsilyl group, benzene ring or F.

5. The organic compound according to claim 1, characterized in that The organic compound is any one of the following compounds:

6. An organic light-emitting device, characterized in that: The organic light emitting device comprises: a first electrode; a second electrode, disposed opposite to the first electrode; The organic functional layer is provided between the first electrode and the second electrode, and the material of the organic functional layer includes at least one organic compound according to any one of claims 1 to 5.

7. The organic light-emitting device according to claim 6, characterized in that: The organic functional layer includes a light-emitting layer. The light-emitting layer includes a host material and a guest material. The guest material includes at least one of the organic compounds.

8. The organic light-emitting device according to claim 7, characterized in that: The mass ratio of the host material to the guest material is in the range of 2.3:1 to 99:

1.

9. The organic light-emitting device according to claim 6, wherein: The organic compound is a green light-emitting material.

10. A display panel, characterized in that: The display panel includes the organic light-emitting device according to any one of claims 6 to 9.

Images